&EPA
            United States
            Environmental Protection
            Agency
            Environmental Research
            Laboratory
            Athens GA 30605
I PA (300 3 /!) ORfi
August 1979
            Research and Development
Adsorption  of
Energy-Related
Organic Pollutants
             A Literature Review

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                               REPORTING

Research reports of the Office of Research and Development, U.S Environmental
Protection Agency, have been grouped into nine series. These nine broad cate-
gories were established to facilitate further development and  application of en-
vironmental  technology. Elimination of traditional  grouping  was  consciously
planned to foster technology transfer and a maximum interface in related fields
The nine series are:

      1    Environmental Health Effects Research
      2   Environmental Protection Technology
      3.   Ecological Research
      4   Environmental Monitoring
      5,   Socioeconomic Environmental Studies
      6   Scientific and Technical Assessment Reports (STAR)
      7   Interagency Energy-Environment Research and  Development
      8.   "Special" Reports
      9.   Miscellaneous Reports

This report has been assigned to the ECOLOGICAL RESEARCH series. This series
describes research on the effects of pollution on humans, plant and animal spe-
cies, and materials. Problems are assessed for their long- and short-term influ-
ences. Investigations include formation, transport, and pathway studies to deter-
mine the fate of pollutants and their effects. This work provides the technical basis
for setting standards to  minimize undesirable changes in living organisms in the
aquatic, terrestrial, and atmospheric environments.
Th'.--.. document is available to the public through the National Technical Informa-
tion Service, Springfield, Virginia 22161.

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                                            EPA-600/3-79-086
                                            August 1979
   ADSORPTION OF ENERGY-RELATED ORGANIC
     POLLUTANTS:  A LITERATURE REVIEW
                    by
      K. A. Reinbold, J. J. Hassett,
     J. C. Means, and W. L. Banwart
    Institute for Environmental Studies
                    and
           Department of Agronomy
University of Illinois at Urbana-Champaign
          Urbana, Illinois  61801
          Contract No. 68-03-2555
              Project Officer

              David S. Brown
      Environmental Processes Branch
     Environmental Research Laboratory
          Athens, Georgia  30605
     ENVIRONMENTAL RESEARCH LABORATORY
     OFFICE OF RESEARCH AND DEVELOPMENT
    U.S. ENVIRONMENTAL PROTECTION AGENCY
          ATHENS, GEORGIA  30605

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                                 DISCLAIMER
This report has been reviewed by the Environmental Research Laboratory, U.S.
Environmental Protection Agency, Athens, GA, and approved for publication.
Approval does not signify that the contents necessarily reflect the views and
policies of the U.S. Environmental Protection Agency, nor does mention of
trade names or commercial products constitute endorsement or recommendation
for use.
                                       11

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                                  FOREWORD

      Environmental protection efforts are increasingly directed towards
prevention of adverse health and ecological effects associated with specific
compounds of natural or human origin.  As part of this Laboratory's research
on the occurrence, movement, transformation, impact, and control of environ-
mental contaminants, the Environmental Processes Branch studies the.-micro-
biological, chemical, and physico-chemical processes that control the trans-
port, transformation, and impact of pollutants in soil and water.

      Efforts to achieve our national goal of energy independence will require
increasing use of our country's vast domestic  coal reserves.  The combustion
of coal or its conversion to a gaseous or liquid fuel, however, can release
numerous organic compounds that are potentially toxic, carcinogenic,  or muta-
genic.  This report reviews the literature on the adsorption of energy-related
organic pollutants and other compounds on sediments and soils.  Information
on the adsorption of these pollutants onto sediments is needed to predict
their movement and fate in aquatic systems so that potential environmental
problems can be anticipated.

                                       David W. Duttweiler
                                       Director
                                       Environmental Research Laboratory
                                       Athens, Georgia
                                     111

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                                  ABSTRACT
     This report is a literature review which was completed as the first
phase of a research project on sorption properties of sediments and energy-
related organic pollutants.  Adsorption of organic compounds in general is
discussed, and analytical methodology in soil thin-layer chromatography and
chemical analysis as applicable to measurement of sorption properties is
summarized.  The literature on the adsorption of energy-related organic
pollutants is reviewed.  Reported constants for the adsorption of organic
compounds on several adsorbents are tabulated, and factors which influence
the adsorption are discussed.

      This report was  submitted in partial fulfillment of Contract No. 68-
03-2555 by the University of Illinois Institute  for Environmental Studies
in cooperation with the Department of Agronomy under the sponsorship of the
U.S. Environmental Protection Agency.  This report covers the period of
July 1977 to April 1978, and work was completed  as of June 1979.
                                     IV

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                                  CONTENTS



    FOREWORD    iii

    ABSTRACT    iv

    FIGURE    vi

    TABLES    vi

    ACKNOWLEDGMENTS    vii

1.  INTRODUCTION    1

2.  SUMMARY AND CONCLUSIONS    8

3.  ADSORPTION OF ORGANIC COMPOUNDS    9

       The Solid-Solution Interface    9
       Adsorptive Forces    9
       Adsorption Isotherms    11

4.  ANALYTICAL PROCEDURES:  SOIL THIN-LAYER CHROMATOGRAPHY    18

5.  ANALYTICAL PROCEDURES:  CHEMICAL ANALYSIS    22

       Recovery of Organic Compounds from Environmental Samples    22
       Fractionation, Cleanup, and
          Separation of Organic Extract Components    23
       Quantitation of Trace Organic Compounds in Solvent Extracts    24

6.  REVIEW AND INTERPRETATION OF ADSORPTION DATA    30

       Factors Influencing Adsorption    30
       Interpretation of Tabulated Data    34

    BIBLIOGRAPHY    114

       Adsorption of Organic Compounds    114
       Analytical Procedures    134
       Compound Characteristics    153
       Occurrence and Distribution of Energy-related Organic Compounds     158

    APPENDIX:  FORMULAS OF ORGANIC COMPOUNDS    161
                                      v

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                                   FIGURE
 1.  Functional Group Model of Bituminous Coal
                                   TABLES
 1.  Organic Contaminants Present in Coal Tar
        from the Synthane Coal Conversion Process     3

 2.  Contaminants Present in Product Water
        from the Gasification of Illinois No. 6  Coal    4

 3.  Classes of Known or Suspected Carcinogenic  or Cocarcinogenic
        Compounds Associated with Processing and Utilization of Coal    5

 4.  Selected Energy-Related Organic Compounds    7

 5.  Kcw, Calculated Koc, Linear Kp and Measured Koc Values for Sorption of
        Pyrene, Dibenzothiophene and Acetophenone by Soils and Sediments    33

 6.  Adsorption Constants for Organic Compounds     36

 7.  Average Values of Adsorption Constants for  Organic  Pesticides    89

 8.  Relationship between Octanol/Water
        Partition and R  Values of Pesticides on a Soil    107

 9.  Leaching of Pesticides from a Soil    108

10.  Sorption Dependence on Sorbate Properties    109
                                    VI

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                              ACKNOWLEDGMENTS
     The authors gratefully acknowledge the assistance and coordination
provided by Dr. David Brown, Project Officer, of the EPA Environmental
Research Laboratory in Athens, Georgia.  Co-principal investigators for
the project under which this review was done were Dr. John J. Hassett,
associate professor of soils, and Dr. Jay C. Means, assistant research
chemist.

     The literature review presented in this report was conducted under the
direction of Dr. Keturah A. Reinbold, associate research biologist, with the
assistance of Ms. Dee Condon and Ms. Carol Wells, research assistants, in
conducting the literature search.  Information on soil thin-layer chroma-
tography was summarized by Dr. Wayne L. Banwart, assistant professor of soils.
Appreciation is expressed to Thomas Knecht, publications director of the
Institute for Environmental Studies, and Cindy Bohde, student editorial
assistant, for the technical editing of this report and to Jean Clarke,
Judith Jones, Trace Black, and Sharon Sparling for typing the report.
                                     vn

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1  INTRODUCTION


        Fossil  fuels are  a major  source  of  anthropogenic organic compounds  in
 the  environment.   Because supplies  of petroleum  and  natural gas are dwindling,
 it will be necessary to  utilize  increasing amounts of  coal to meet our energy
 needs in the  near future.  As  Figure 1  illustrates,  coal  is a complex organic
 chemical.   Either the combustion of coal or its  conversion to a gaseous or
 liquid fuel breaks the coal into numerous  simpler organic compounds, which
 then appear in process waste streams and may be  released  into the environ-
 ment.  These  coal fragments include a great variety  of polycyclic aromatics,
 heterocyclic-  and carbonyl-polycyclics, and aromatic amines, groups which  all
 contain known  or  suspected carcinogens, as well  as phenolics and long-chain
 aliphatic hydrocarbons (TRW Systems and Energy,  1976;  Sharkey et al., 1976).

        Coal conversion processes produce large volumes of gaseous and aqueous
 effluents (Magee, Bertrand, and  Jahnig, 1976).   Hundreds  of thousands of tons
 of gases containing volatile organics,  particulates, and  combustion gases  are
 released each day-  These emissions may disperse over  hundreds of miles, dis-
 tributing the  effluent materials in both terrestrial and  aquatic systems.
 With such large volumes  of effluents, even trace components are distributed
 in significant amounts—up to  hundreds  of  pounds per year.  Some of these
 materials are  potentially toxic, carcinogenic, or mutagenic.

        Aqueous effluents may be  released at a rate of  up  to 5 million gallons
 each day.   Also,  large volumes of aqueous  leachate from stockpiles of coal or
 solid wastes,  such as ash and  char, are produced.  The wastes from the vari-
 ous  steps of  the  coal conversion process contain a variety of organic materi-
 als.

        A number of organic products have been detected in the wastes from
 coal conversion pilot plants.  Forney et al.  (1974)  identified some of the
 major organic  compounds  in tars  produced by the  Synthane  coal gasification
 process (Table 1), and Schmidt,  Sharkey, and Friedel (1974) analyzed the
 process water  (Table 2).   TRW  Systems and  Energy (1976) listed several or-
 ganic compounds which are associated with  the processing  and utilization of
 coal and which are known or suspected carcinogenic or  cocarcinogenic com-
 pounds (Table  3).

        Clearly, large quantities of organic compounds  are introduced into
 aquatic systems,  either  directly in aqueous effluents  or  indirectly from gas-
 eous effluents.   The behavior  of these  compounds in  aquatic systems depends
 largely upon the  extent  to which they are  adsorbed on  suspended or  settled
 sediments.

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                                                         \    /   \
                                                     H    H    H   H
Figure 1.  Functional group model of bituminous coal (Wiser).

Source:  Wewerka, Williams, and Vanderborgh,  1976.

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                TABLE  1.   ORGANIC CONTAMINANTS PRESENT IN
            COAL  TAR FROM THE SYNTHANE COAL CONVERSION PROCESS
Volume (percent)
Illinois
Structural Type No . 6
Benzenes
Indenes
Indanes
Naphthalenes
Fluorenes
Acenaphthenes
3-ring aromatics
Phenyl naphthalenes
4-ring aromatics - peri
4-ring aromatics - cata
Phenols
Naphthols
Indanols
Acenaphthols
Phenanthrols
Diben zo f urans
Dibenzothiophenes
Benzonaphthothiophenes
N-hetero cycles
2.1
8.6
1.9
11.6
9.6
13.5
13.8
9.8
7.2
4.0
2.8
+
0.9
-
2.7
6.3
3.5
1.7
10.8
Lignite
4.1
1.5
3.5
19.0
7.2
12.0
10.5
3.5
3.5
1.4
13.7
9.7
1.7
2.5
-
5.2
1.0
-
3.8
Mon tana
S ubb i turn ino us
3.9
2.6
4.9
15.3
9.7
11.1
9.0
6.4
4.9
3.0
5.5
9.6
1.5
4.6
0.9
5.6
1.5
-
5.3
Pittsburg
Seam
1.9
6.1
2.1
16.5
10.7
15.8
14.8
7.6
7.6
4.1
3.0
+
0.7
2.0
-
4.7
2.4
-
8.8
Source:  Forney et al., 1974

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              TABLE 2.  CONTAMINANTS PRESENT IN PRODUCT WATER
                FROM THE GASIFICATION OF ILLINOIS NO. 6 COAL
 Compound
                                            Concentration (ppm)
 Phenols
 Cresols
 C  -phenols
 C  -phenols
 Dihydric phenols
 Benzofuranols
 Indanols
 Acetophenones
 Benzoic Acids
 Hydroxybenzaldehyde
 Naphthols
 Indenols
Benzofurans
 Dibenzofurans
Biphenols
Benzothiophenols
Pyridines
Quinolines
Indoles
                                               2,660 to 3,400
                                               2,610 to 2,840
                                                 560 to 1,170
                                                  70 to 150
                                                  60 to 300
                                                  70 to 120

                                                  60 to 210

                                                  40 to 210
                                                 110 to 160
                                                     90
                                                  10 to 30
                                                     10
                                                  20 to 40
                                                  60 to 110
                                                  60 to 580
                                                  10 to 20
                                                  20 to 70
 Source:   Schmidt,  Sharkey,  and Friedel, 1974.
                                 OBJECTIVES
        To  examine  the adsorption of energy-related organic compounds  in  the
environment,  a  research project was initiated  in the Institute  for Environ-
mental  Studies  at  the University of Illinois  at Urbana-Champaign.  The pro-
ject is  supported  by  the U.S.  Environmental Protection Agency under contract
number  68-03-2555.  This report presents  the  results  of the first phase of
the project,  the objective of  which was to review published literature on (1)
the adsorption  of  energy-related organic pollutants on sediments, (2)  the
theory of  adsorption,  and  (3)  analytical techniques pertinent to^adsorption
measurements.   Because the literature survey produced only a limited amount

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of information on the adsorption of energy- related organic compounds, a
variety of organic compounds were included in this review to provide a back-
ground of information.

                                  APPROACH

       The literature was searched by a combination of computer and manual
methods.  The 1970-77 volumes of Chemical Abstracts were searched using-the
computerized Bibliographic Retrieval Service System.  The key words used were
terms such as adsorption, desorption, and sediments accompanied by the names
of compound groups or of specific compounds which may be energy- re la ted or-
ganic pollutants, including all those listed in Table 4.  Earlier volumes of
Chemical Abstracts were searched manually, as were pertinent books, series of
Residue Reviews, current journals, and the 1977 Weekly Government Abstracts
from the National Technical Information Service.

       The computerized search produced more than 900 citations.  Copies of
approximately one-third of these references were obtained for review.  With
the addition of those acquired by manual searching, a total of 670 references
were obtained for review.  A bibliography is included at the end of this
report.

          TABLE 3.  CLASSES OF KNOWN OR SUSPECTED CARCINOGENIC
               OR COCARCINOGENIC COMPOUNDS ASSOCIATED WITH
                     PROCESSING AND UTILIZATION OF COAL
Compound Class
                          Representative  Compound
                                                           Structure
 Polynuclear  Aromatic  Hydrocarbons


 Anthracenes               9- , 10-dimethylanthracene
Chrysenes
 Benzanthracenes
Fluoranthenes
Cholanthrenes
                          chrysene
                         benzo (a) anthracene
                         benzo ( j ) f luoranthene
                          3 -methylcholanthrene

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                              TABLE 3,  continued
 Compound Class
                          Representative Compound
Structure
 Benzopyrenes
 Dibenzpyrenes
                        benzo(a)pyrene
                        dibenzo(a,h)pyrene
 Nitrogen-,  Sulfur-,  and Oxygen-Containing Polycyc'lic Compounds
 Mono-  and
 dibenzacridines
Benzocarbazoles
                         dibenz(a,h)acridine
                           7H-benzo (c , g) carbazole
 Benzathrones
 Aromatic Amines
                          7H-benz(d,e)anthracen-7-one
 Aminoazobenzenes
                         4-dimethylamincazobenzene
 Naphthylamines
                        a-naphthylamine
 Cocarcinogens and Promoting Agents
Phenols/naphthols        ot-naphthol
Long-chain  aliphatic
hydrocarbons              n-dodecane
Source:  TRW Systems and Energy, 1976.

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            TABLE 4.   SELECTED ENERGY-RELATED ORGANIC COMPOUNDS
Polynuclear Aromatics

Anthracene
Phenanthrene
Acenaphthene
Fluorene
Naphthacene
Chrysene
Pyrene
Triphenylene
Perylene
1,2-Benzopyrene
3,4-Benzopyrene
1,2-Benzanthracene
1,2,7,8-Dibenzanthracene
1,2,5,6-Dibenzanthracene
1,2,3,4-Dibenzanthracene
7,12-Dimet±iylbenzanthracene
3-Methylcholanthrene
S-Heterocyclics
2 ,3-Benzothiophene
Dibenzothiophene
N-Heterocyclics
Carbazole
Indole
Acridine
Pyridines
Pyrroles
Benzocarbazole
Dibenzocarbazole
Benzoquinoline
Phenolics
1-Naphthol
2-Naphthol
Acenaphthol
4-Indanol
4-Benzofuranol
4-Hydroxybenzothiophene
2,3,4-Trimethyl Phenol
Miscellaneous
Acetophenone
Anthraquinone
Benzidine
Benzophenone
                                 REFERENCES
 Forney,  A.  J., W.  P.  Haynes,  S.  J.  Gasior,  G. E. Johnson, and J. P. Strakey,
    Jr.   1974.  Analyses of Tars, Chars, Gases, and Water Found in Effluents
    from  the Synthane  Process.  Progress Report 76.  Bureau of Mines, U.S.
    Department of  the  Interior.

 Magee, E. M., R.  R. Bertrand, and C. E. Jahnig.  1976.  Environmental impact
    and R and D needs  in coal  conversion.  In Symposium Proceedings:  Environ-
    mental Aspects  of  Fuel Conversion Technology, III, pp. 395-403.  Report No.
    EPA-600/2-76-149.  Washington, D. C.:  Office of Research and Development,
    U. S. Environmental Protection Agency.

 Schmidt, C. E., A. G. Sharkey, Jr., and R.  A. Friedel.  1974.  Mass Spectre-
    metric Analysis of Product Water from Coal Gasification.  Technical
    Progress Report 86.  Bureau of Mines, U. S. Department of the Interior.

 Sharkey, A. G., J. L- Schultz, C. White, and'R. Lett.  1976.  Analysis of
    Organic Material in Coal, Coal Ash, Fly Ash, and Other Fuel and Emission
    Samples.  Report No. EPA-600/2-76-075.   Washington, D. C.:  Office of
    Research and Development, U. S. Environmental Protection Agency.
TRW Systems and Energy-  1976.
   Processes.  Oak Ridge, Tenn
   Administration.
   Carcinogens Relating to Coal Conversion
  :   U.  S.  Energy Research and Development
Wewerka, E. M., J. M. Williams, and N.E. Vanderborgh.  1976.  Contaminants in
   Coals and Coal Residues.  Report No. LA-UR 76-2197-  Los Alamos, N. M.:
   Los Alamos Scientific Laboratory.
                                      7

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2   SUMMARY  AND CONCLUSIONS


     We have  reviewed the literature on the adsorption of energy-related
organic pollutants and other organic compounds on sediments,  soils,  and other
selected adsorbents.  Adsorption constants reported in the literature for
organic compounds are compiled in Tables 6 and 7, and factors which influence
adsorption are discussed.

     Among the many factors which influence adsorption are several molecular
properties of compounds.  It has been shown that as chain length, molecular
volume, molecular weight, and carbon number increase, and as polarity de^
creases, adsorption of hydrophobic compounds increases.  These properties are
related to water solubility of the compound.  The adsorption of hydrophobic
compounds increases with decreasing water solubility, but for more polar
compounds adsorption increases with decreasing water solubility only within
a family of compounds.  Soil organic matter content influences adsorption and
has been shown to correlate with the partitioning of nonpolar organic com-
pounds between octanol and water.  This relationship makes possible the cal-
culation of Koc and Kp values when Kow is known.

     Little of the published information pertains specifically to the adsorp-
tion of energy-related organic pollutants onto sediments or soils.  Data are
available on  the adsorption of a few such compounds onto carbon, but those
results cannot be directly extrapolated to sediments or soils.  Investigation
of adsorption of these compounds on sediments is beginning, as in the lab-
oratory phase of this project.  Information on the adsorption of these
pollutants onto sediments is needed to predict their movement and fate in
aquatic systems.  To obtain sufficient information, further research is
necessary -

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3 ADSORPTION OF  ORGANIC COMPOUNDS

                                                                J.  J.  Hassett

                       THE SOLID-SOLUTION INTERFACE

       The adsorption or concentration of organic materials at the solid-
solution interface is of particular importance in natural waters.   Streams,
lakes, and rivers contain a variety of colloidal materials both in their
bottom sediments and dispersed  throughout the  aqueous phase.   These colloids
can actively sorb organic materials, removing them from solution or suspension,
and hence can have a marked effect on the chemical and physiological proper-
ties of the organic pollutants.

       The sediments in a natural body of water consist predominantly of
organic colloids (such as clay minerals and metal oxides, hydroxides,  and car-
bonates) , of organic colloids, and of living organisms.   The metal oxides and
hydroxides and the organic colloids may exist as discrete particles or as
coatings on other colloids such as the clay minerals.  A major source of these
inorganic colloids (and, to a certain extent, of the organic colloids)  is the
erosion of watershed soils .  The properties of the sediments can be quite
similar to those of the soils from which they are derived, or they may be sub-
stantially altered from the original soil, since the sediments may be subject
to physical sorting by the water and often to different chemical environments
(e.g., lower redox potentials).

       Adsorption at the solid-liquid interface results  when the forces of
attraction between the surface  (adsorbent) and the solute (adsorbate)  over-
come the forces of attraction between the solvent and the solute.   Hence, the
degree of adsorption depends on the relative strengths of the adsorbate-
adsorbent interactions and the solute-solvent interactions.  If the adsorbate-
adsorbent interactions dominate due to a strong adsorbate-adsorbent inter-
action or due to a weak solvent-solute interaction, adsorption will take
place and the adsorbing species will be primarily associated with the solid
phase.  The net interaction of the surface and the adsorbate may result from
a variety of chemical and electrical interactions (Stumm and Morgan, 1970;
Adamson, 1967).


                             ABSORPTIVE FORCES

       1.  Coulomb'ic attraction.  This force of attraction results when a
charged surface such as a clay mineral attracts an oppositely charged ion to
maintain electrical neutrality.  The force of attraction is given by
Coulomb's law:

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                 F =

 where q-i  is the  charge  density  of  the  surface, q2  is  the  charge of the adsorb-
 ing species,  D is the dielectric constant of  the solvent  and is a measure  of
 the shielding ofq^ from q2  by the  solvent, and X is the distance between the
 charges.   Sorption of inorganic cations by negatively charged  soil colloids in
 the process of cation exchange  is  one  example of coulombic attraction.  The
 sorption  of the  organic cations paraquat and  diquat by montmorillonite and
 kaolinite (Weber et al.,  1965)  is  also an example  of  coulombic attraction.
 In the case of paraquat and diquat sorption within the interlayer of montmor-
 illonite,  other  sorptive  forces add to the coulombic  attraction.

        2.   London-van der Waals dispersion forces  result  from  the oscillating
 electron  cloud  of one  atom rotating in phase with a  nonoverlapping oscil-
 lating electron  cloud of  another atom, producing a dipole-like attraction.
 The differential heats  of adsorption are of the order of  1 to  2 kcal mole
 for small  molecules and atoms.  For large molecules the heats  of adsorption
 may be much larger. Corkill et at.  (1966) gave the heats of adsorption of
 methane,  ethane,  pentane  and hexane on carbon black as being 3, 4.3, 9.2 and
 11.4 kcal  mole"-*-.

        3.   Orientation  energy results  from the attraction of a permanent di-
 pole for  another permanent  dipole.   The resulting  energy  of attraction is less
 than 2 kcal mole  "^.

        4.   Induction forces result from the attraction of an induced dipole
 for the inducing  species  which  can be  either  a permanent  dipole or a charged
 site or species.   This  force often adds to the adsorptive forces present in
 cases  of coulombic or orientation  energy attraction.  The energy of attraction
 is  less than  2 kcal mole  .

        5.   Hydrogen bonding occurs in  compounds such  as water  where electrons
 are unequally shared between the more  electronegative oxygen and hydrogen.
 This  arrangement  results  in a slight negative charge  on the oxygen atom and a
 slight positive  charge  on the hydrogen atoms, producing  (in the case of water)
 a dipole moment of 1.84 Debye units (Douglas  and McDaniel, 1965).  Hence,
 attraction  is possible  between  dissimilarly charged sites of the adsorbate
 and the adsorbent.  The energy  of  attraction  ranges from  2 to  10 kcal mole  .

       6.   Chemical forces  result  when the adsorbate-adsorbent bond approaches
an  ordinary chemical bond in strength  (»10 kcal mole"1) .  Chemical forces
extend over only very short ranges  and often  result in the nature  of the ad-
sorbate being  significantly different  in the  adsorbed state.  Such adsorption
is often termed chemisorption to distinguish  it from  the  less specific low-
energy physical sorption.   It is often difficult to distinguish between chemi-
cal  and physical  sorption because  a chemisorbed layer may have  physically
sorbed layers upon it.

       For  some solutes the attractive force  of the adsorbate for the solid
surface can play a  subordinate  role to the hydrophilic-hydrophobic balance  of
the solute with the solvent (Hance,  1967; Stumin and Morgan, 1970) .  ThlS type

                                     10

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of adsorption is of particular interest when considering the adsorption of
organic molecules that are concentrated at the solid-solution interface be-
cause of the hydrophobic nature of their hydrocarbon parts.  For this type of
adsorption the effect of the adsorbent on the interfacial tension or surface
free energy would appear to be an important consideration in explaining the
observed phenomena.  Conversely, some ions that show a strong affinity for the
solvent (for example, ones that are highly hydrated) may stay in solution even
if they are specifically attracted to the adsorbent.

       Traube observed a regularity in the lowering of surface tension by
members of three homologous series of esters, alcohols, and fatty acids
(Kipling, 1965) .  The rule derived from that study states, in essence, that
the tendency to adsorb organic compounds from aqueous solution increases with
increasing molecular weight for members of a homologous series.  Hence, ad-
sorptive energy increases systematically for each additional Ct^ group.

       Other general rules (Stumm and Morgan, 1970)  concerning the adsorption
of organics state that a polar adsorbent adsorbs the most polar constituent of
a nonpolar solution in preference to the least polar constituent (s) .   In con-
trast, a nonpolar surface adsorbs the nonpolar component preferentially from
a polar solution.

                            ADSORPTION ISOTHERMS

       Several mathematical expressions — some with a theoretical basis and
others entirely empirical in nature — have been employed to describe the re-
lationship between the amount adsorbed and the equilibrium solution concen-
tration.  Those equations that have a theoretical basis can (if the assump-
tions each is based upon are met) provide valuable information about  bonding
or adsorption energies (affinities) , adsorption maxima (capacities) ,  and in-
terfacial free energies.  The empirical equations provide a framework for pre-
dicting the distribution of adsorbate between the solid and aqueous phases.

Langmuir Adsorption Isotherm

       The Langmuir equation (1918) , originally developed to describe the ad-
sorption of a gas by a clean solid surface, has been used by numerous inves-
tigators to describe adsorption at the solid-liquid interface.  The equation
usually takes the following form (Veith and Sposito, 1977) :
where           x/m = amount of adsorbate adsorbed per unit mass of adsorbent
                  C = the equilibrium concentration of the adsorbate in
                      solution
                  K = a constant related to the bonding energy of the
                      adsorbate to the adsorbent
                  b = adsorption maximum or capacity factor

Correct use of the equation requires that two assumptions be met:
                                     11

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        1.  That  the  adsorbed ions be bound in a monolayer on a homogeneous
 surface with localized sites.
        2.  That  the  energy of adsorption be the same for each molecule of ad-
 sorbate regardless of the degree to which the monolayer is completed.

       Veith and Sposito  (1977) have shown that it is necessary not only to
 meet  the basic assumptions of the Langmuir equation but also to have an inde-
 pendent means of determining that the only process taking place is adsorption,
 since the Langmuir equation will also fit data obtained in situations where
 secondary precipitation is taking place.  Other investigators  (Stumm and
 Morgan, 1970; Kipling, 1965) have also cautioned that although a set of data
 may fit the equation, that fact is not of itself sufficient evidence that the
 assumptions have been met.

       The normal application of the Langmuir equation to adsorption data
 involves a least-squares fitting of the data to a linear form of equation 2.
 At least three linear forms of the Langmuir equation have been used in adsorp-
 tion studies:

                C/(x/m) = l/Kb=C/b                 (Eq. 3)

                 l/(x/m) = 1/b+l/KbC                (Eq. 4)

                 (x/m) = b-(x/m)/KC                 (Eq. 5)

       Equation 3 has been used extensively in adsorption studies involving
 soils.  A plot of C/(x/m)  against C for this equation should yield a straight
 line having a slope of 1/b and an intercept at I/Kb.  For equation 4 the plot
would be I/(x/m) against 1/C, yielding a slope of I/Kb and an intercept at
 1/b.  This type of plot is very similar to the double-reciprocal or Lineweaver-
Burk plot used in enzyme studies employing Michaelis-Menten kinetics.  For
 equation 5 (x/m) is plotted against  (x/m)/C, yielding a slope equal to 1/K
 and an intercept at b.  This plot is of the same form as the Eadie-Hofstee
plot (Hofstee, 1952; 1960) also employed in Michaelis-Menten kinetics.

       Dowd and Riggs (1965) compared the statistical fit and the predictabil-
 ity of the three linear forms of the Michaelis-Menten equation, which have the
same form as the Langmuir adsorption isotherm and its linear equations:

                    V   C
                     max s
                v =
                    K + C                           (Eq. 6)
                         s
                C /v = K /V   +C /V                 (Eq. 7)
                 s      m  max  s  max
                1/v = 1/V-  +K /V   C               (Eq- 8)
                 '     ' max  m  max s
                v = V   -K v/C
                     max  m   s
                                                   (Eq. 9)
                                     12

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where
                v    = the initial velocity of the reaction

                C    = the concentration of the substrate
                 s

                V    = the maximum initial velocity
                 max

                K    = the Michaelis constant
                 m

       They found that equation 7, which has the same form as equation 3, and
equation 9, which has the same form as equation 5, gave comparable predictions
of the two constants when the error in determining the dependent variable
(i.e., v or x/m) was small, although equation 9 would better show deviations
from linearity.  Equation 9 gave  the best results when the error associated
with determining the dependent variable was large.  These results are sup-
ported by Syers et al. (1973), who in a soil adsorption study compared the
form of the Langmuir equation given in equation 3 with that of equation 5.
Dowd and Riggs  (1965) concluded that the Lineweaver-Burk or double reciprocal
plot—equation  8, which has the same form as equation 4--should not be used
even if it fits the data well.

       Several  nonlinear forms of the Langmuir equation are used in adsorption
studies:

                6 = KC/(1+KC)                      (Eq.  10)

                (x/m) = bC/(K'+C)                   (Eq.  11)

Equation 10 is  the same as equation 2 except that adsorption is expressed in
terms of the percentage of the monolayer that is occupied by adsorbate mole-
cules.  This results in b, the monolayer capacity, having a value of 1 unit of
adsorption sites and disappearing from the adsorption equation.  Equation 11
reduces to equation 2 if K' is replaced with 1/K;  hence, K1  = 1/K.

Freundlich Adsorption Isotherm

       To describe adsorption from dilute solutions, Freundlich (1922) applied
the adsorption  isotherm:

                a = ac                             (Eq.  12)

or in its more  commonly used form:

                (x/m) = KC1//n                      (Eq.  13)
where
                              = the equilibrium concentration in the
                                solution after adsorption
                a or x/m      = the adsorption value
                                      13

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                 a, K, and 1/n = constants

 In studies of the adsorption of a variety of organic compounds on charcoals
 Freundlich found the adsorption exponent 1/n to vary between 0.1 and 0.5.

        The Freundlich adsorption equation is normally considered an empirical
 equation relating the amount adsorbed to the equilibrium adsorbate concentra-
 tion.  Kipling (1965) cites a derivation of the Freundlich equation by Henry
 (1922)  based on combining an expression for the free energy of a surface with
 the Gibbs equation.   The resulting equation defines the adsorption exponent in
 terms of the monolayer capacity and surface free energy:
                 (x/m)  =KC0-           (Eq.

 hence
                 1/n = (RT(x/m)m/(a0-0'i)             (Eq. 15)

 where
                 (x/m)m = the monolayer capacity

                     
-------
 Usually  K   > K ;  that is,  a given surface coverage  will be in equilibrium with
 a  greater  concentration of the  solute for an adsorption process  than for the
 desorption process.

       The Freundlich equation  is normally statistically fit to  adsorption
 data  in  its linear form:

                 log(x/m)  = logK + 1/n logC         (Eq.  19)

 A  plot of  log(x/m)  against logC yields a slope of 1/n and an intercept equal
 to logK.

       In  many studies the difference in adsorption of an organic material by
 several  soils has been correlated with the organic  carbon content of the adsor-
 bate.  When the adsorption constants  are put on an  organic carbon basis,  the
 differences in adsorption are often removed.
                 K   = K x -LUU                      (Eq. 20)
                  oc     %OC


 Gibbs  Adsorption Equation

        The  Gibbs equation,  originally  derived for  the  adsorption  at  the  liquid-
 liquid interface (Kipling,  1965)  has been  applied  to the  adsorption  of solutes
 from dilute solutions by solid surfaces  (Stumm and Morgan,  1970):


                   =  8y                             (Eq. 21)
                  is
                      U LJ •

                  y . =  y .+RTlna.                     (Eq. 22)
 hence,
1-4 _zi
|  i    RT
                                                    (Eq.  23)
                                T,P. ally's except y.
                                and y    constant
                                     H2°
 where

                  .  = the adsorption density of component
 ri
                  Y = the interfacial tension

                 ^2 = the chemical potential
                 a . = the activity of component i-
                  ^

The Gibbs equation defines adsorption in terms of the effect of a solute in
either increasing or decreasing interfacial tension.  The equation illustrates
that solutes which lower the interfacial tension tend to be concentrated at
the interface.  Many organic substances tend to lower the interfacial tension
and hence are accumulated at the interface.

                                      15

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                                 REFERENCES


 Adamson,  A.  W.   1967.  Physical Chemistry of Surfaces.  New York:  Wiley.

 Corkill,  J.  M.,  J.  F.  Goodman, and J. R. Tate.   1966.  Adsorption of  non-ionic
      surface-active agents  at  the graphon/solution  interface.  Trans. Far.
      Soc. pp. 535-44.

 Douglas,  B.  E.,  arid D. H. McDaniel.   1965.   Concepts and Models  of Inorganic
      Chemistry.   Waltham, Mass.:   Blaisdell Publishing Co.

 Dowd, J.  E., and D. S. Riggs.   1965.   A comparison  of estimates  of
      Michaelis-Menten kinetic  constants from various linear transformations.
      J.  Biol.  Chem. 240:863-69.

 Freundlich,  H.   1922.   Colloid and Capillary  Chemistry.   London:  Methion
      & Co.

 Hance, R. J.  1967.  Relationship  between partition data and the adsorption
      of some herbicides  by soils.   Nature  214:630-31.

 Henry, D. C.  1922.  A kinetic theory of adsorption.  Philos.  Mag.
      44:689-705.

 Hofstee,  B.  H. J.   1952.   On the evaluation of the  constants V  and K  in
      enzyme  reactions.  Science  116:329-31.                   m       m
       I
 Hofstee,  B.  H. J.   1960.   Nonlogarithmic linear titration curves.
      Science 131:39.

 Kipling,  J.  J.   1965.  Adsorption from Solutions of Non-electrolytes.
      New  York:   Academic Press.

 LaFleur,  K.  S.   1976.  Carbaryl desorption  and movement in soil  columns.
      Soil Sci.   121:212-16.

 Langmuir, I.  1918.  The  adsorption of gases  on plane  surfaces of  glass,
      mica and platinum.   J.  Amer. Chem.  Soc.   40:1361-1403.

 Stumm, W., and J. J. Morgan.   1970.   Aquatic  Chemistry.   New York:
      Wiley Interscience.

 Syers, J. K., M. G.  Browman, G. W. Smillie, and R.  B.  Corey.   1973.
      Phosphate sorption  by  soils evaluated  by  the Langmuir adsorption
      equation.   Soil Sci. Soc. Amer.  Proc.  37:358-63.

Veith, J. A., and G. Sposito.  1977.  On the use of  the Langmuir equation
      in the  interpretation  of  "adsorption" phenomena.  So^l Sci.  Soc.
     Amer. J. 41:697-702.
                                     16

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Weber, T. B., P. W. Perry, and R. P. Upchurch.  1965.  The influence of
     temperature and time on the adsorption of paraquat, diquat, 2,4-D and
     prometone by clays, charcoal, and an anion-exchange resin.  Soit So'L.
     Soc. Am.3 Proc. 29:678-88.
                                      17

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 4 ANALYTICAL METHODS:   SOIL THIN-LAYER CHROMATOGRAPHY

                                                                W. L. Banwart

        The  principle of thin-layer chromatography  (TLC) and evidence of its
 widespread  use  are presented by Stahl  (1965).  The basis of all chromato-
 graphic separations is similar in that a mobile phase passes over a station-
 ary  phase and thereby transports different substances with varying speeds in
 the  direction of  the flow.  Conventional TLC is a  form of elution chromato-
 graphy in which molecules of the test compounds are exchanged between the
 mobile and  stationary phase as a solvent carrying  the compounds migrates
 across a uniform  thin layer of stationary phase fixed to a glass plate.  The
 rate or relative  rate of movement of the test compounds is dependent on their
 physical properties and on experimental parameters.  The solvent employed may
 be water, an  organic solvent, or a mixture of solvents allowing movement of
 the  test compounds.

        The  mobility or migration distances of substances on the TLC chromato-
 grams can be  expressed in terms of their relative mobility, Rf  (Stahl, 1965),
          -  distance of spot center from .starting point
            distance of solvent from starting point.
 The  use of  relative mobilities provides reproducible- data, whereas absolute
 mobilities, which are defined simply as the distances of the spot centers from
 the  starting  point, may vary considerably with experimental conditions.

        Using  TLC  to study the mobility of compounds requires a method for doc-
 umenting the  substances' movement.  The final position of the compounds on
 the  chromatogram  can be made visible with dye indicators, fluorescence under
 ultraviolet light (Pullan, Howard, and Perry, 1966), a bioassay  (Helling,
 Kaufman,  and  Dieter, 1971), a spark-chamber  apparatus  (Pullan et al, 1966),
 a beta  camera (Snyder, 1970), and autoradiography  using X-ray film (Mangold,
 Kammereck,  and Malins, 1962).  In the last of these methods, chromatograms
 are  developed using ^c labeled test compounds; X-ray film is then exposed to
 the  chromatogram  for several days before development.  The developed films
make  it  possible  to observe visually the movement  of the test compounds and
 can  be  used for easy calculations of Rf values.  For quantitative measure-
ments,  radioactive compounds on TLC plates can be  counted directly by commer-
 cially  available  instruments such as strip scanners (Ravenhill and James,
1967) or  by zonal analysis where small successive segments  of the chromatogram
are  scraped from  the plate and radio-assayed by liquid scintillation  spectro-
metry  (Brown  and  Johnston, 1962).  Thin-layer chromatography  has been used as
a standard method for separating and identifying many  synthetic  and natural
organic  compounds  (Maier and Mangold, 1964;  Stahl and  Mangold, 1975),  includ-
ing polynuclear aromatic hydrocarbons (Zoccolillo and  Liberti, 1976;  Candeli
et al.,  1975).

                                    18

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       Soil thin-layer chromatography was introduced by Helling and Turner
(1968).  In soil TLC a uniform but relatively thin layer  (often less than
1 mm) of a soil-water slurry is spread on TLC plates and allowed to dry.  The
soil then serves as the stationary phase interacting with compounds carried
by the mobile phase.  Soil TLC has provided a much simpler and faster way of
determining compound mobilities in soil than the traditional leaching columns.
Helling and Turner  (1968) found that pesticide mobilities determined by soil
TLC correlated well with published data.  The mobility of substances on soil
TLC plates have been reported by Helling and Turner (1968) as frontal Rf
values where
          _ distance of frontal edge of spot or streak from starting point
            distance of solvent edge from starting point
Standard or reference compounds can be spotted on each plate to improve
reproducibility.

       Data obtained by soil TLC provide information of a nature somewhat
different from  that obtained with sorption isotherms or partition coeffi-
cients.  A compound on a soil TLC chromatogram may move as a compact band or
as a diffuse streak.  From the type of movement it is possible to draw con-
clusions about  the homogeneity of the soil material or of the compound itself.
It is also possible to obtain a relative measure of the distance compounds
might leach in  a soil system when finite amounts of water are applied.  Rj->
values have been used (Rhodes, Belasco, and Pease, 1970), where
          _ distance moved by bottom of spot
        k   distance traveled by solvent
to measure the  relative soil depth through which essentially all of a given
organic compound (pesticide) applied to a soil has leached.  Thus, soil TLC
provides some kinds of information that cannot be obtained strictly from
adsorption constants or partition coefficients.

       Data recalculated from Rhodes, Belasco, and Pease  (1970) showed simple
correlation coefficients of r = 0.95 between Freundlich K and frontal Rf
values for four agricultural chemicals applied to two soils.  Helling (1971c)
reported highly significant negative correlation coefficients for soil adsorp-
tion of nonionic herbicides and Rf values of the same or chemically similar
herbicides.  As determined by leaching experiments, the mobilities of six
organophosphorus insecticides (McCarty and King, 1966) , three acidic herbi-
cides (Hamaker, Goring and Youngson, 1966) and their five s_-triazine herbi-
cides (Harris, 1966) were inversely related to their adsorption by the soil.
Data by Hance  (1967), using two soils and 29 organic compounds, show corre-
lation coefficients ranging from 0.85 to 0.91 for the amount of compound
adsorbed by the soil and the Rf values for TLC using 40% aqueous ethanol as
a solvent.  Other workers (Martin and Synge, 1941; Stahl, 1965) have also
discussed the relationship between K and Rf values.  If a correlation between
Rf (mobility)  and K (adsorption isotherm) values for a given set of organic
compounds can be established, it should be possible to predict K values for
additional test compounds on a particular soil.

       The greatest use of soil TLC to date has been the study of pesticide
mobility in soils (Helling 1971a,b,c; Hance, 1967), but applying the tech-
nique to other mobile organic compounds should provide useful data.
                                      19

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                                  REFERENCES
  Brown, J. L., and J.  M. Johnston.   1962.   Radioassay of lipid components
       separated by thin-layer chromatography.   J.  Lipid Res.  3:480-81.

  Candeli, A.,  G.  Morozzi, A.  Paolacci,  and L.  Zoccolillo.   1975.  Analysis
       using thin-layer and gas-liquid chromatography of polycyclic aromatic
       hydrocarbons in  the exhaust products from a European car running on
       fuels containing a range of concentrations of these  hydrocarbons.
       Atmos.  Environ.  9:843-49.

 Hamaker, J. W., C. A.  I. Goring, and C. R. Youngson.  1966.  Sorption and
      leaching of 4-amino-3,5,6-trichloropicolinic acid in soils.  Advan. Chem
      Ser. 60:23-37.

 Hance, R. J.  1967.  Relationship between partition data and the adsorption
      of some herbicides by soils.  Nature  214:630-31.

 Harris, C. I.   1966.  Adsorption, movement, and phytotoxicity of monuron and
      s-triazine herbicides in soil.  Weeds 14:6-10.

 Helling, C. S.  1971a.  Pesticide mobility in soils.  I: Parameters of
      soil thin-layer chromatography.  Soil Sci. Soc. Amer. Pros. 35:732-37.

 Helling, C. S.  1971b.  Pesticide mobility in soils.  II:  Applications of
      soil thin-layer chromatography.  Soil Sci. Soc. Amer. Proc. 35:737-43.

 Helling, C. S.  1971c.  Pesticide mobility in soils.  Ill: Influence of
      soil properties.   Soil Sci. Soo. Amer. Proc.  35:743-48.

 Helling, C. S.,  and B. C. Turner.  1968.  Pesticide mobility:  Determination
      by soil thin-layer chromatography.  So-ience 162:562-63.

 Helling,  C. S.,  D.  D.  Kaufman, and  C. T. Dieter.  1971.  Algae bioassay
      detection of pesticide mobility in soils.  Weed Sci.  19:685-90.

 McCarty,  P.  L.,  and P. H. King.   1966.   The movement of pesticides in soils.
      Purdue Univ.  Eng.  Bull.,  Ext.  Ser. no. 121:156-71.

Maier,  R.,  and H.  K. Mangold.   1964.  Thin-layer chromatography.  Advan.
      Anal.  Chem.  and Instrum.  3:369-477.

Mangold, H.  K. , R.  Kammereck,  and D. C. Malins.   1962.   Thin-layer  chroma-
      tography  as  an analytical and  preparative tool in  lipid radiochemistry.
      Micro chemical  Journal Symposium Series  2:697-714.

Martin, A.  J.  P.,  and  R.  L. M.  Synge.   1941.   A  new  form of chromatography
      employing two  liquid phases.   I: A theory of chromatography.  n:
     Application  to the  micro-determination of the higher monoaminoacids in
     proteins.  Biochem.  J. 35:1358-68.

                                      20

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Pullan, B. R., R. Howard, and B. J. Perry.  1966.  Measuring radionuclide
     distribution with crossed-wire spark chambers.  Nucleonics 24:72-75.

Ravenhill, J. R., and A. T. James.  1967.  A simple sensitive radioactive
     scanner for thin-layer chroma tog rams .  J.  Chromatog.  26:89-100.

Rhodes, R. C., I. J. Belasco, and H. L. Pease.   1970.  Determination of
     mobility and adsorption of agrichemicals on soils.  J-  Agri-c.  Food
     Chem. 18:524-28.

Snyder, R.  1970.  Thin-layer radiochromatography and related procedures.
     In Progress in Thin-layer Chromatography and Related Methods,  ed.
     A. Niederwieser and G. Pataki, Vol. 1, pp. 52-73.  Ondon:  Ann Arbor-
     Humphrey Science Publishers.

Stahl. E., ed.  1965.  Thin-layer Chromatography.  New York:  Academic  Press.

Stahl, E., and H. K. Mangold.  1975.  Techniques of thin-layer chromatog-
     raphy-  In Chromatography.  3d ed., ed. E. Heftmann,  pp. 164-88.
     New York:  Van Nostrand Reinhold Company.

Zoccolillo, L. , and A. Liberti.  1976.  Determination of polycyclic hydro-
     carbons by channel thin-layer Chromatography.  J. Chromatog.  120:485-88.
                                      21

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 5  ANALYTICAL  PROCEDURES:   CHEMICAL  ANALYSIS

                                                                  J. C. Means

         The analysis of trace  organic  compounds  in water or bound to soil  and
 sediment samples is a complicated  task because of a number of  factors.  First,
 the water and soil or sediment may contain  a wide variety of organic compounds
 of different polarities,  molecular weights, and  structures.  Second, the af-
 finities of different types  of organic compounds for different soil-sediment
 types span a large range.  Third,  the  solubilities of organic  compounds in
 different solvents vary considerably.  Fourth, interactions between soil com-
 ponents and many types of organic  compounds are  poorly understood.

         In general, the process of analyzing trace organic components in water
 and soil or sediment samples may be divided into these tasks:

         1.  Quantitative  recovery  of the organic compound of interest

         2.  Separation of that compound from other types of organic compounds

         3.  Quantitation  of  the organic compound using spectroscopy, chromato-
             graphy,  and radioactivity  or a combination of techniques.

           RECOVERY OF ORGANIC  COMPOUNDS FROM ENVIRONMENTAL SAMPLES

         To accurately determine the amount of a  given organic  compound in  a
 water sample or  bound to  a soil or sediment sample, the compound must be
 quantitatively recovered  from  the  gross sample.  In the case of a soil or
 sediment sample,  recovery  is routinely accomplished by extracting the compound
 from  the soil in a Soxhlet apparatus.  Depending upon the variety of compounds
 which require analysis, a  single solvent, a series of solvents, or a mixture
 of  solvents  may  be required.   For  example, a cyclohexane or benzene extraction
 (Sawicki,  1964;  Hermann,  1974)  is  typically used to recover aliphatic and
 aromatic  hydrocarbons 'from sediments,  whereas a  benzene and methanol mixture
 may be  used  to remove a broad  spectrum of nonpolar and polar organics (Giger
 and Blumer,  1974;  Blumer  and Youngblood, 1976).  Acetone has been used to
 extract polar organics  and humic substances.*  Regardless of the extraction
 procedure  used,  it is always necessary to perform recovery studies using a
 reference  compound to verify that  the  expected extraction efficiencies  are
 achieved.

        Organic  compounds  may be quantatively recovered from water samples
 using one of three  techniques.  Compounds having low boiling points  and  low
or intermediate polarities may  be  stripped from  the water  by  passing a pure
*F. J. Stevenson, 1977:  personal communication.

                                      22

-------
inert gas through the sample and collecting it in a trap containing a gas
chromatographic column packing  (e.g., Tenax GC)  (Bellar and Lichtenberg, 1974;
Kuo et al., 1977) .  Soluble organic compounds may be recovered from water by a
series of extractions using single or mixed solvents.  In some analytical
schemes, the pH of the water may be altered (i.e., made basic, neutral, and
acidic) to achieve partial separation of compounds having ionizable functional
groups.   (U.S. EPA, 1977; Acheson et al., 1976; Chang, 1976; Webb et al.,
1973) .  A third technique, one which has been used very successfully, is to
collect organic compounds by sorption on purified activated carbon (Keith et
al., 1976) or on purified sorbant resins (e.g., XAD-2, 4, and 8) (Malcolm,
Thurman, and Aiken, 1977; Junk et. al.,  1974; Adams, Menzies, and Levins, 1977).
These techniques have the advantage that the organics contained in a very
large sample volume may be collected on a relatively small amount of resin.
However, the recovery efficiencies for  different types of organics adsorbed
from the water and subsequently desorbed from the resin vary significantly.
Therefore, the recovery of each compound of interest should be evaluated.
Another advantage of the resin sorption technique is that both polar and non-
polar organics may be sorbed to the resin and eluted for analysis.

        Once an extract has been prepared from either a solid or a water
sample, it is usually necessary to reduce the volume so as to bring the con-
centrations of the extracted components into a detectable (ppm)  analytical
range.  The best general technique available for this process is the use of a
Kuderna-Danish evaporator  (Webb et al., 1973;  U.S. EPA, 1977).  In some cases
air evaporation or evaporation under a  stream of nitrogen may be sufficient,
but several studies have shown that significant losses of extracted organics
may occur  (Chiba and Mosley, 1968; Goldberg, Delong, and Sinclair, 1973).
Similarly, rotary vacuum evaporation may be appropriate for certain compounds,
but losses of many extracted components may occur.  Extracts are typically
concentrated by a factor of 500 to 10,000, depending upon the origin of the
extract and the sensitivity of the analytical systems being used.  Here again,
it is advisable to test the recovery efficiency for the compound of interest
using the concentration .technique being considered.

    FRACTIONATION, CLEANUP, AND SEPARATION OF ORGANIC EXTRACT COMPONENTS

        Organic extracts of soil or sediments and of water,  particularly those
from industrial areas, may contain hundreds of components.  These multiple
components tend to complicate the accurate quantitation of individual constit-
uents.  Therefore, some steps may be needed to fractionate the extract prior
to analysis.  To some extent, fractionation begins with the selection of an
extracting solvent or sorption resin.   However, solvent selectivities are
rarely sufficient, especially when concentration factors are high.  Solvent-
solvent partitioning of the organics in an extract may be useful in crude
fractionations (e.g., separating polar  compounds from nonpolar compounds).

        Liquid chromatography and thin-layer chromatography (TLC) provide the
best selectivities in fractionating complex mixtures of organics.  For rela-
tively large extracts, separation on liquid chromatographic columns containing
such adsorbents as silica gel,  alumina,  or Florisil is the method of choice.
Excellent separations of complex mixtures from acidic, basic,  and neutral
fractions of coal wastes and cigarette-smoke condensates have been achieved

                                      23

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 using these three adsorbents (Swain,  Cooper, and Stedman, 1969;  Bell, Ireland,
 and Spears, 1969; Severson et al.,  1976).

         In the last few years,  a number of advances in liquid chromatographic
 column packings have provided investigators with a number of gel-permeation
 and adsorption materials which can  be extremely useful in fractionating and
 separating complex mixtures into subsamples which can be analyzed and quanti-
 tated.

         For relatively small samples, thin-layer chromatography can be used
 successfully to fractionate a complex mixture.   The same basic substrates men-
 tioned above for use in column chromatography are used for TLC separations.
 Careful selection of solvents and the use  of two-dimensional development can
 yield excellent purifications of individual components prior to quantitation.
 A large number of investigators have  employed TLC to purify compounds for stuiy
 or to fractionate extracts prior to quantitative analysis (Treiber, 1976;
 Grant and Meiris, 1977; Bender, 1968; White and Howard, 1967; Pierce and Katz,
 1975; Stanley, Bender, and Elbert,  1973; additional references are given in
 the analytical techniques section of  the bibliography at the end of this
 report) .

         QUANTITATION OF TRACE ORGANIC COMPOUNDS IN SOLVENT EXTRACTS

         The quantitation of individual components of a complex mixture after
 partial cleanup or fractionation may  generally be achieved using the tech-
 niques of spectroscopy, gas chromatography, liquid chromatography, or, in
 appropriate cases, liquid scintillation counting or combinations of the
 above techniques.

         Spectroscopic techniques, which are based on some characteristic
 absorption wavelength (in the UV, visible, or infrared spectrum) of the com-
 pound or  a derivative, vary in their  selectivity and sensitivity.  In cases
 where the  extracts contain relatively few  components, spectroscopic methods
 may be successfully used to quantitate a component without additional cleanup
 or separation.   In most cases,  however,  the spectroscopic techniques must be
 used  in combination with compatible separation systems (e.g., liquid chroma-
 tography or thin-layer chromatography).  A large body of literature exists on
 separations and quantitations of organic pollutants using the above techniques.
 Representative  reports are those of Caton, Matthews,  and Walters (1976); Kelly
 (1967); Willis  (1973);  Freudenthal  et al.  (1975); Jenkins and Baird (1975);
 Brocco, Cantuti,  and  Cartoni  (1970);  and IUPAC  Applied Chemistry Division
 (1974) .  Additional references  are  listed  in the  bibliography.

        One  spectroscopic technique which  offers a relatively high degree of
both  selectivity  and  sensitivity is the  use of  fluorescence  spectra of various
 compounds  or their fluorescent  derivatives (Woo et al .,  1978) .   These  tech-
niques are  particularly useful  when combined with liquid  chromatography  for
the analysis of many  coal-derived substances (Stroupe  et al.,  1977)  and pesti-
cides  (Mallet, Belliveau,  and Frei, 1975).   All of these spectroscopic  tech-
niques have  the advantage that  they are  not destructive to the sample being
analyzed and that the  column  packing  materials  and thin-layer  supports used


                                      24

-------
for separations prior to spectral analysis can cover an almost unlimited range
of molecular weights.

        Gas chromatography  (GC) is perhaps the most widely used technique for
the separation and quantitation of organic compounds.  Methods are available
for almost every class of organic pollutant including many energy-related com-
pounds.  Column packing materials are available for the separation of com-
pounds representing a broad spectrum of polarities and functional groups.  Al-
though fewer liquid phases are readily available, capillary columns have dem-
onstrated increasing utility for the separation of the highly complex mixtures
of organics typically found in environmental extracts.

        Gas chromatographic separations in general are better than those
offered by liquid chromatography, but the compounds which can be analyzed by
GC are limited to those having significant vapor pressures at temperatures
below 400 C.  In most cases, gas chromatographic analysis is destructive of
the sample.  A wide variety of GC detector systems are available.  The flame
ionization detector is the most common universal type.  A number of other
types of detectors demonstrate selectivities for specific types of compounds
(e.g., the electron capture detector for halogens, the thermionic detector
for nitrogen and phosphorus, and the flame photometric detector for sulfur
and phosphorus).  All of these detection systems may be used to quantitate
organic compounds with the use of appropriate internal standardization tech-
niques.  The literature contains a large amount of information on this general
topic.  Pertinent references are included in the bibliography.

        In the last decade, gas chromatography has been combined with mass
spectrometry, providing investigators with a very powerful analytical system
which can be used to both identify and quantitate organic compounds (John
and Nickless, 1977; Janini et al., 1976; Alford, 1977; Oswald, Albro, and
McKinney, 1974; O'Reilly and Murrmann, 1974; Lao, Thomas, and Monkman, 1975;
and McGuire, Alford, and Carter, 1973).

        In certain types of experiments, radiolabeled organic compounds may be
used successfully to follow the movement of trace organics in environmental
samples.  When labeled compounds are used, many types of samples may be ana-
lyzed directly without the need for extraction, concentration, or cleanup
procedures.  Care must be taken, however, to insure that the labeled compound
introduced into the experimental system is not degraded in such a way that the
radioactivity is lost or transferred to other compounds.  The sample is typi-
cally separated by (1) thin-layer chromatography followed by radioautography
or liquid scintillation counting or (2) by liquid chromatography followed by
liquid scintillation spectrometry.  Carbon -14 or tritium -3 labeled compounds
can be detected in liquid samples by liquid scintillation spectrometry on
aliquots of the samples.  If solid samples are to be analyzed, the radiola-
beled compound may be extracted and then analyzed as a liquid sample.  Solids
may also be analyzed directly by pyrolytic combustion of the solid and recov-
ery of the radioactivity as 14CO2 or 3H20.
                                      25

-------
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 Adams,  J.,  K.  Menzies,  and P.  Levins.   1977.   Selection and Evaluation of
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 Alford,  A.   1977.   Environmental applications of mass  spectrometry.  Bio-
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 Bell, J.  H., S.  Ireland,  and A.  W.  Spears.   1969.   Identification of  aromatic
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 Bellar,  T.  A.  and J.  J.  Lichtenberg.   1974.   Determining volatile organics
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 Bender,  D.  F.   1968.   Thin-layer chromatographic  separation and spectro-
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 Blumer,  M.,  and W.  W. Youngblood.   1976.   Poly cyclic. Aromatic  Hydrocarbons
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 Brocco,  D.,  V.  Cantuti,  and G. P. Cartoni.   1970.   Determination of poly-
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 Caton, R. D. Jr., J. B. Matthews, and E.  A. Walters.   1976. Development of
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 Chang, R. C.   1976.  Concentration  and Determination  of Trace  Organic
     Pollutants in  Water.   Ph.D. dissertation, Ames Laboratory,  Iowa  State
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Chiba, M. , and H. V. Mosley.   1968.  Studies of losses of  pesticides during
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Freudenthal, R. I., A. P. Leber, D.  Emmerling, and P. Clarke.   1975.   The
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     alterations in the pattern  of benzo[a]pyrene metabolism.   Chem.  - Biol.
     Interact.  11:449-58.
                                      26

-------
Giger, W.,and M. Blumer.   1974.  Polycyclic  aromatic  hydrocarbons  in  the
     environment:  Isolation  and characterization by  chromatography -  visible
     ultraviolet, and mass  spectrometry.  Anal.  Chem.  46:1663-71.

Goldberg, M. C., L. Delong, and M. Sinclair.   1973.   Extraction  and concen-
     tration of organic solutes from water.  Anal.  Chem.  45:89-93.

Grant, D. W., and R. B. Meiris.  1977.  Application  of thin-layer and  high-
     performance liquid chromatography to the  separation  of polycyclic  aro-
     matic hydrocarbons in  bituminous materials.  J.  Chromatogr. 142:339-51.

Hermann, T. S.  1974.  Development of Sampling Procedures for Polycyclic
     Organic Matter and Poly chlorinated BiphenyIs.  Washington,  D.C.:   Office
     of Research and Development, U. S. Environmental Protection Agency.

IUPAC Applied Chemistry Division.  1974.  Analytical  methods for use  in
     occupational hygiene:  Determination of benzo[a]pyrene and  benzo[fe]flu-
     oranthene in airborne  particulates  (chromatography and optical fluo-
     rescence) .  Pure Appl. Chem. 40:36.1-36.7.

Janini, G. M., G. M. Muschik, and W. L. Zielinski,  Jr.  1976.  N,N'-Bis[p-
     butoxybenzylidene]-a,a'-bi-p-toluidine:   thermally stable liquid crystal
     for unique gas-liquid  chromatography separation  of polycyclic aromatic
     hydrocarbons.  Anal. Chem. 48:809-13.

Jenkins, R. L., and R. B.  Baird.  1975. The determination of benzidine in waste
     waters.  Bull. Environ.  Contam. Toxicol.  13:436-42.

John, E. D., and G. Nickless.  1977.  Gas chromatographic method for the
     analysis of major polynuclear aromatics in particulate matter.
     J. Chromatogr. 138:399-412.

Junk, G. A., J. J. Richard, M. D. Grieser, D. Witiak,  J. L. Witiak, M. D.
     Arguello, R. Vick, H.  J. Suec, J. S. Fritz, and  G. V. Calder.  1974.
     Use of macroreticular  resins in the analysis of  water for trace organic
     contaminants.  J. Chromatogr.  99:745-62.

Keith, L. H., A. W. Garrison, F. R. Allen, M. H. Carter, T. L. Floyd, J. D.
     Pope, and A. D. Thurston, Jr.   1976.  Identification of organic com-
     pounds in drinking water from thirteen U. S. cities.  In Identification
     and Analysis of Organic Pollutants in Water, ed.  L. H. Keith.  Ann Arbor,
     Mich.:  Ann Arbor Science Publishers, Inc.

Kelly, J. A.  1967.  The Determination of Phenolic-type Compounds in Water
     by High-pressure Liquid Chromatography.  NTIS No. ORD-4254-15.  Ph.D.
     dissertation, Oklahoma State University.

Kuo, P. P. K., E. S. K.  Chian, J. H. Kim, and F. B. DeWalle.  1977.  Study of
     the gas stripping,  sorption, and thermal desorption procedures for pre-
     concentrating volatile polar organics from water samples for analysis by
     gas chromatography.  Anal.  Chem. 49:1023-29.
                                     27

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 Lao,  R.  C.,  R.  S.  Thomas,  and J.  L.  Monkman.   1975.   Computerized^gas chro-
      matographic-mass spectrometric  analysis  of polycyclic aromatic hydrocar-
      bons in environmental samples.   J.  Chromatrogr.  112:681-700.

 McGuire, J.  M.,  A.  L. Alford, and M.  H.  Carter.   1973.   Organic Pollutant
      Identification Utilizing Mass Spectrometry.   Report No.  EPA-R2-73-234.
      Corvallis,  Oregon:  National Environmental  Research Center, Office of
      Research and  Monitoring,  U.S. Environmental  Protection Agency.

 Malcolm, R.  L.,  E.  M. Thurman, and G.  R.  Aiken.   1977.   The concentration and
      fractionation of trace organic  solutes  from natural and  polluted waters
      using XAD-8,  methylmethacrylate resin.   In Proceedings of the llth Annual
      Conference  on Trace Substances  in Environmental  Health.   Columbia, Mo. :
      University  of Missouri.   In  press.

 Mallet,  V.  N., P.  E. Relliveau,  and R.  W.  Frei.   1975.   In situ fluorescence
      spectroscopy  of pesticides and  other organic pollutants.   Res.  Dev.
      59:51-90.

 O'Reilly, W.  F. , and R.  P.  Murrmann.   1974.   Identification of Soil Organics
      using a Gas Chromatographic/Mass  Spectrometric Method.   Washington,  D.c.:
      Directorate of Military  Engineering  and  Topography Office, Chief of
      Engineers,  U.  S. Army.

 Oswald,  E.  O., P.  W.'Albro,  and J. D.  McKinney.   1974.   Utilization of gas-
      liquid  chromatography coupled with  chemical ionization and electron
      impact  mass spectrometry for the  investigation of  potentially hazardous
      environmental  agents  and their  metabolites.   J.  Chromatogr. 98:363-448.

 Pierce,  R. C. , and  M.  Katz.   1975.   Determination of" atmospheric isomeric
      polycyclic arenes by  thin-layer chromatography and fluoresence spectro-
      photometry.  Anal.  Chem.  47:1743-48.

 Sawicki,  E.   1964.   The  separation and analysis  of polynuclear aromatic hydro-
      carbons present  in  the human environment.   Chem. Anal. 53:24-30.

 Severson, R. F. , M. E. Snook,  H.  C.  Higman, 0.  T.  Chortyk, and F.  J.  Akin.
      1976.   Isolation, identification, and quantitation of the polynuclear
      aromatic hydrocarbons  in tobacco  smoke.   In Carcinogenesis—A Comprehen-
      sive Survey., Vol. 1,  ed.  R.  Freundenthal and P.  W.  Jones, pp.  253-70.
      New York:  Raven Press.

Stanley, T. W., D.  F.  Bender,  and W. C. Elbert.   1973.   Quantitative  aspects
      of thin-layer chromatography in air  pollution measurements.   In  Quan-
      titative Thin Layer Chromatography,  ed.  J.  C. Touchstone,  pp.  305-22.
     New York:  Wiley  - Interscience.

Stroupe, R. C., P.  Tokousbalides,  R. B. Dickinson, Jr.,  E. L.  Wehry,  and
     G. Mamantov.  1977.  Low temperature fluorescence spectrometric deter-
     mination of polycyclic aromatic hydrocarbons  by matrix isolation.
     Anal. Chem.  49:701-5.
                                      28

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Swain, A. P., J. E. Cooper, and R. L. Stedman.  1969.  Large-scale fractiona-
     tion of cigarette smoke condensate for chemical and biologic investiga-
     tions.  Cancer Res, 29:579.

Treiber, L. R.  1976.  An extension of the programmed multiple development
      (PMD) technique.  J. Chromatogr. 124:69-72.

U. S. Environmental Protection Agency [u. S. EPA].  1977.  Sampling and
     Analysis Procedure for Screening of Industrial Effluents for Priority
     Pollutants.  Cincinnati, Ohio:  Environmental Monitoring and Support
     Laboratory, U. S. EPA.

Webb, R. G., A. W. Garrison, L. H. Keith, and J. M. McGuire.  1973.  Current
     Practice in GC-MS Analysis of Organics in Water.  NTIS No. PB-224-947.
     Southeast Environmental Research Laboratory, Athens, Ga.:  U. S. Envi-
     ronmental Protection Agency.

Woo, Ching S.,  A. P. D'Silva, V. A. Fassel, and G. J. Oestreich.  1978.
     Polynuclear aromatic hydrocarbons in coal—identification by their x-ray
     excited optical luminescence.  Environ. Sci. Technol. 12:173-74.

White, R. H., and J. W. Howard.  1967.  Thin-layer chromatography of poly-
     cyclic aromatic hydrocarbons.  J. Chromatogr. 29:108-14.

Willis, R. B.  1973.  High Pressure Liquid Chromatography of Phenols and
     Metal Ions.  U. S. Atomic Energy Commission.
                                     29

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 6   REVIEW  AND  INTERPRETATION OF  ADSORPTION  DATA

                                             K. A. Reinbold and J. J. Hassett

         A review of the literature revealed relatively few data on the adsorp-
 tion of energy-related organic pollutants by sediments or soils.  The summary
 presented here, therefore, covers literature on a variety of types of organic
 compounds, including pesticide data from references not covered by Farmer
 (1976).

         Some of the published reports included constants for the sorption of
 organic  compounds on various adsorbents.  These constants are tabulated at the
 end  of  this chapter.  However, many sources containing sorption data did not
 report  sorption constants.  The latter publications are included in the bibli-
 ography .

         Except in the case of pesticides, most of the adsorption constants
 reported for organics were derived using adsorbents other than sediments,
 soils, and clay minerals.  The most commonly used adsorbents were activated
 carbon or  ion exchange resins, which are often used for the removal of organ-
 ics  in water treatment processes.  Nylon and cellulose triacetate have also
 been  used.  The pesticide data, however, do pertain to sorption on sediments,
 soils, or  clay minerals.  The adsorption constants were determined in most
 cases by  fitting experimentally derived data to various forms of the Freund-
 lich or Langmuir adsorption equations.

                       FACTORS INFLUENCING ADSORPTION

       Adsorption is a process in which a solution component is concentrated
 at the solid-solution interface.  Adsorption results when the forces of at-
 traction  between the solution component and the surface, that is, the adsor-
 bate-adsorbent interaction, overcomes the forces of attraction between the
 solution  component and the solvent, that is, the solute-solvent interaction.
 There are  two general cases where the adsorbate-adsorbent interaction is
 greater  than the solute-solvent interaction and adsorption results.

       In  the first case there is a strong positive interaction between the
 surface and the adsorbate, and this interaction is strong enough to overcome
 even a fairly strong solute-solvent interaction.  In this case adsorption is
primarily related to the nature of the bonding between the adsorbate and the
 adsorbent.  The adsorption of organic cations such as paraquat by clay min-
 erals or polar organic molecules within the montmorillonitic interlayer are
 examples of this type of adsorption (Weber et al.3 1965) .  Reviews emphasizing
 the effect of adsorbate and adsorbent properties on adsorption have been writ-
 ten by MDrtland (1970), Adams(1973), Bailey and White (1970), and Weber (1972).
                                      30

-------
       In the second case, adsorption takes place not because of a strong
adsorbate-adsorbent interaction, but rather due to a weak solute-solvent in-
teraction.  In this case even a small positive adsorbate-adsorbent interaction
can overcome the solute-solvent interaction and result in adsorption.  The
degree of adsorption or partitioning of the adsorbing material between the
solid and aqueous phases is primarily determined by the suitability of the
aqueous phase as a solvent for the material.  The poorer the aqueous phase as
a solvent for the adsorbing species, the weaker the solute-solvent interaction
and the greater the adsorption.

       The adsorption of nonpolar aromatic hydrocarbons of low water solu-
bility by organic surfaces is an example of this type of adsorption (Karick-
hoff et al., 1979; Means et al., 1979).  This type of adsorption has been
called "hydrophobic adsorption" because of the emphasis on the weak solute-
solvent interaction in determining the degree of adsorption in aqueous systems
(Horvath and Melander, 1978)

       Hydrophobic or nonpolar adsorption can be considered an example of a
nonpolar organic compound  (adsorbate) partitioning between a polar aqueous
phase and a stationary organic phase (adsorbent).  In a soil or sediment sys-
tem the aqueous phase would be the soil solution or the interstitial water in
the sediment, while the organic phase would be the naturally occurring humic
materials.  Factors which either increase the affinity of the adsorbate for
the humic surfaces or decrease the affinity of the adsorbate (solute)  for the
solvent (water) would result in greater adsorption.

       Van der Waals forces have been identified as the main source of
adsorbate-adsorbent interactions between nonpolar compounds and nonpolar
organic surfaces  (Horvath and Melander, 1978).  The differential heats of
adsorption for van der Waals forces are of the order of 1 to 2 kcal mole
for small molecules; these forces may be much greater for larger molecules,
especially with an increase in the number of double and triple bonds (Bailey
and White, 1970) .  This 'is illustrated by the adsorption of methane, ethane,
pentane and hexane by carbon black.  These hydrocarbons gave differential
heats of adsorption of 3, 4.3, 9.2 and 11.4 kcal mole"1, respectively (Corkill
et at., 1966).  The differential heats of adsorption do not increase indef-
initely with increasing molecular size; eventually a point is reached where
increasing molecular size does not increase adsorption and may even decrease
adsorption due to steric hindrance.

       Many factors influence the solute-solvent interaction and hence in-
fluence adsorption.  Molecular properties such as chain length, molecular
volume, molecular weight, carbon number, and polarity have all been shown to
influence adsorption (Bailey and White, 1970; Gustafson and Paleos, 1971;
Lailach et al., 1968; Cummings et al., 1959; Bartell and Miller, 1924;
Kipling, 1965; Hansen and Craig, 1954; Parkash, 1974).  It has been demon-
strated that as chain length, molecular volume, molecular weight, and carbon
number increase, and as polarity decreases, the solute-solvent interaction
weakens and hydrophobic adsorption increases.  The effect of all of these
properties on the solute-solvent interaction is integrated into the water
solubility of the compound.
                                     31

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        The adsorption of hydrophobia compounds has been shown to increase with
 decreasing water solubility of the compound (Karickhoff et al . ,  1979; Means
 et al . , 1979) .  The adsorption of more polar compounds has also been shown to
 increase with decreasing water solubility, but only within a family of com-
 pounds (Bailey and White, 1970) .   Aqueous solubilities of organic compounds,
 while  useful in predicting adsorption, are often difficult to determine.  Some
 of the difficulties encountered include the approach of the water solubilities
 to analytical detection limits,  the formation of stable suspensions and the
 long equilibration times required to establish equilibrium.

        Lambert (1968)  discussed the similarity between the role  of soil or-
 ganic matter in the sorption of organic compounds and the role  of an organic
 solvent in a liquid-liquid extraction.  He observed that the partitioning of
 a nonpolar organic compound between the soil solution and soil organic matter
 was highly correlated with the partitioning of the compound between water and
 an organic solvent.  Karickhoff et al .  (1979)  reported, for sorption placed
 on an organic carbon basis (Koc) ,  a significant correlation between the sorp-
 tion of several aromatic hydrocarbons and the partitioning of the compounds
 between octanol and water (Kow) .

                 log Koc = 1.00 log Kow - 0.21      (Eq. 24)

        The linear partition coefficients (Kp)  for many compounds may be cal-
 culated from the following equation:

                 Kp = Cs/Cw                         (Eq. 25)
 where

                 Cs = the concentration of the compound in the solid phase  at
                      equilibrium

                 Cw = equilibrium  solution concentration of the compound

 When  the  individual linear partition  coefficients for the sorption of a hydro-
 phobic  organic  compound by a  variety  of different sediments and  soils are
 divided by  the  respective sediment or soil  organic carbon contents,  a unique
 constant Koc  is produced.

                      Kp x 100
                Koc = ~     —                     (E(3-  26)
This constant is  independent of  soil or  sediment  (adsorbent) properties and
is only dependent on the nature  of  the adsorbing  species  (Karickhoff et al . ,
1979; Means et al . , 1979).

       The relationship between  Koc values and Kow values for hydrophobic
compounds has several distinct merits.   First, Kow determinations are more
reliable than water solubility determinations, particularly for the highly
hydrophobic compounds.  Second,  once a compound's Kow value has been measured
or calculated, its Koc can be determined from equation 24.  Third, if the
organic carbon contents of the individual soils or sediments are known, then
their respective  Kp values for the adsorption of the compound can be cal-
culated.
                                     32

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       Table 5 gives an  example  of  linear Kp values,  measured Koc values and
Koc values calculated  from Kow values  for the sorption of three hydrophobic
compounds, pyrene, dibenzothiophene and acetophenone  by a variety of sediments.

TABLE 5.  Kow, CALCULATED Koc, LINEAR  Kp AND MEASURED Koc VALUES FOR SORPTION
      OF PYRENE, DIBENZOTHIOPHENE AND  ACETOPHENONE BY SOILS AND SEDIMENTS
Koc Sample
Compound Kow
Pyrene 124,000













Dibenzo- 24,000
thiophene












Aceto- 38.6
phenone












(calc'd) No.
76,400 B2
4
5
6
8
9
14
15
18
20
21
22
23
26
14,700 B2
4
5
6
8
9
14
15
18
20
21
22
23
26
23.8 B2
4
5
6
8
9
14
15
18
20
21
22
23
26
%OC
1.21
2.07
2.28
0.72
0.15
0.11
0.48
0.95
0.66
1.30
1.88
1.67
2.38
1.48
1.21
2.07
2.28
0.72
0.15
0.11
0.48
0.95
0.66
1.30
1.88
1.67
2.38
1.48
1.21
2.07
2.28
0.72
0.15
0.11
0.48
0.95
0.66
1.30
1.88
1.67
2.38
1.48
Kp
774
1098
1191
633
125
79
285
783
509
747
1159
811
1130
1023
117.5
180.6
167.1
60.8
9.4
5.8
49.7
179.9
65.1
101.4
276.0
176.3
388.6
134.5
0.44
0.89
0.56
0.68
0.07
0.09
0.12
0.27
0.30
0.29
0.85
0.53
0.68
0.66
Koc
(meas 'd)
63,991
53,019
52,250
87,847
83,333
71,818
59,271
82,453
77,182
57,469
61,628
48,557
47,487
69,108
9711
8725
7329
8444
6267
5273
10,354
18,937
9864
7800
14,681
10,557
16,328
9088
36
43
24
95
48
82
25
28
46
22
45
31
29
45
Average
Koc
63,400













11,230













38.6













                                      33

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        The range in Kp values for the adsorption of hydrophobia  compounds
 depends on the compound being adsorbed and the range in organic carbon contents
 found in the soils or sediments studied.   The upper limit for Koc values de-
 pends on the compound, but appears to be  around 2,000,000 due to present
 analytical chemistry limitations.  The lower limit for the validity of the
 Koc-Kow relationship has not yet been defined.   This limit will be reached
 when case 1 adsorption, i.e., a specific  strong adsorbate-adsorbent inter-
 action, is encountered.

        A relationship has been demonstrated for nonlinear Freundlich isotherms
 when the data are expressed on a molar basis instead of a mass basis (Osgerby,
 1970).   Molar Kd values may be calculated from mass Kd values by the following
 equation:

            Kd(Molar)  = Kd(Mass)  x Molecular weight            (Eq. 27)
                              Molecular weight

 Where Kd(Mass)  and 1/n are Freundlich constants and the molecular weight is
 that of the adsorbate.

                       INTERPRETATION  OF TABULATED DATA

         Various  combinations  of the influencing factors discussed above are
 necessary to explain  the adsorption data  obtained from the literature  and
 tabulated at the end  of this  chapter.   For  the  nonpesticide organics,  the  ad-
 sorbents used in most of the  studies  reviewed were  montmorillonite clay or
 carbon  rather than natural  sediments  or soils.   Thus,  rather  than a variety  of
 adsorbents with  a range of  characteristics,  two distinctly different types are
 represented:   an inorganic  clay mineral and an  organic.

         The  chemical  characteristics  of the adsorbate  account for much  of  the
 variation in  adsorption behavior shown in the tabulated data.  These effects
 were  best shown  in studies  of groups  of related compounds.  Linner and
 Gortner  (1935) studied the  adsorption of  31 organic acids on  carbon; the re-
 sults are  summarized  in Table 6.   Traube's  rule that adsorption from aqueous
 solutions  increases with molecular weight for a homologous series was  demon-
 strated  for fatty  acids  but not  for other acids.   The  branched chain had
 little effect on the maximum  adsorption of  the  acids,  but the double bond
 showed a  tendency  to  decrease adsorption.   The  introduction of polar groups—
 carboxyl, hydroxyl, or keto—caused decreased adsorption.   The decrease was
more  pronounced  as the number of carboxyl groups increased or as  a second
hydroxyl group was introduced.   The decrease  in adsorption  caused by the keto
group was dependent on the  length of  the  chain  and  the position of the  polar
group in the chain.

        For 52 structurally related N-phenylcarbamates, acetanilides, and
anilines from aqueous  2% ethanol  solutions,  the  inverse relationship between
solubility and adsorption accounted for 60  percent of the total variation  in
adsorption, shown by the data  in  Table  6  (Ward  and Upchurch, 1965).  All of
the compounds were adsorbed on nylon  and  cellulose triacetate.  Other than
solubility, the principal variable factor affecting adsorption was the  diff-
erence in the molecular  structures of  the compounds.  An investigation of

                                      34

-------
compounds having systematic variations in molecular structure shows which
sites in the molecule can be involved in adsorptive processes and how various
substituents may influence the extent of adsorption.  For those compounds,
differences in molecular structure caused differences in adsorption as a re-
sult of steric hindrance, tautomerism, chelation, and induction.  The results
suggest that the preferred adsorption mechanism of the amido compounds from
aqueous solution is via the adsorbate's imino hydrogen and the adsorbent's
carbonyl oxygen.  If neither of these is available, however, alternative
binding sites are utilized.

        As a means of establishing a g_uantitative relationship between soil
sorption equilibria and chemical structure, Lambert (1967) proposed the
following relationship between parachor of uncharged organic chemicals for
which no appreciable hydrogen bonding occurs and the soil sorption of those
chemicals :
                K  = alAu              (Eq. 25)

The relationship is based upon extrathermodynamic linear free energy approxi-
mations and uses of parachor as an approximate measure of the molar volume of
the chemical.  Distribution equilibria between soil and water for a number of
chemical homologs of two chemical classes, including anilines (see Table 6)
were used to establish the relationship.  The relationship emphasizes the im-
portance of using the partition or distribution coefficient, defined with re-
spect to organic matter, as the most representative index of soil sorption
equilibria.

        Hance  (1969) extended this relationship.  A factor given by (parachor-
45N) , where N  is the number of sites in a molecule which can participate in
the formation  of a hydrogen bond, was correlated with the logarithm of the
Freundlich K value for the adsorption of 29 aromatic herbicides.  Again, the
relationship is valid for soils in which organic matter is the dominant adsorb-
ing 'constituent.

        In the case of a few compounds, adsorption constants were determined
for more than  one adsorbent (Table 6) .  Where data were obtained on both a
clay mineral and a sediment, the adsorption was generally greater on the sedi-
ment.  Some data on sediments and soils, including those for benz.(a)pyrene,
pyrene, methoxychlor , and carbaryl, show a correlation between adsorption and
organic matter content (Table 6)  (Smith, Mabey, Bohonos, Holt, Lee, Chou, MilL
and Bomberger, 1976a; Karickhoff, Brown, and Scott, 1978; La Fleur, 1976a) .

        In addition to the adsorption constants for specific compounds and
adsorbents, additional pertinent data are tabulated here.  Adsorption con-
stants for a number of pesticides averaged over several soils are shown in
Table 7.  Also, Tables 8 and 9 show the inverse relationship between R
values obtained by soil thin-layer chromatographs and adsorption or adsorbate
characteristics .

(Note:   the references cited in this chapter are listed beginning on p. 110.)
                                      35

-------
                                       TABLE 6:   ADSORPTION CONSTANTS FOR ORGANIC COMPOUNDS
     Compound Name
                                                                                                             Ref.
en
Acids, Aliphatic

  acetic acid

      C2H402

    Compound properties^

      m.w. 60.05

      m.p. 16.604°C

      b.p. 117.9°C

      density 1.0492?°

      water sol °°
                                                 COMPOUNDS OTHER THAN PESTICIDES
                                           Adsorbent

                                             nordite
                                               (decolorizing
                                                  carbon)
Adsorption equation:  a= ?jj_ -
                                                                       0.462   0.266   1.736
                                                                  Adsorption equation:  a= aC
                                                                                              1/n
                                                                       a       1/n
                                                                       2.46    0.351
                                           Experimental Conditions:  1 gm of adsorbent and
                                             concentrations or reagents varying from 0.01
                                             to 0.25 molar.
                                                                                                                  Linner
                                                                                                                   and Gortner.
                                                 1935
       See notes at end of table

-------
                                                  TABLE 6:  Continued
Compound Name
                                                                       Ref.
  adipic acid


      C6H10°4
    Compound properties

      m.w. 146.14a

      m.p. 151°Ca

      b.p. 265°C at 100mma

      density 1.360jsa
      water sol 1.5
                   isfc
Adsorbent              Adsorption equation:  a=—j^—p
  nordite                   	
    (decolorizing
       carbon)              °e     °        B
                            2.347  1.886    1.245
                       Adsorption equation:  a=aC
                            a      1/n
                            1.79   0.163



Experimental Conditions:  same as for acetic acid.
                                                                       Linner
                                                                        and Gortner,

                                                                        1935
  butyric acid

      C4H8°2

    Compound properties0

      m.w. 88.12°C

      m.p. -4.26°C

      b.p. 163.53-C

      density 0.95775°

      water sol «•
Adsorbent

  nordite
     (decolorizing
        carbon)
                       Adsorption equation:  a= ?? c
                            aB     a        8
                            1.689  0.863    1.957



                       Adsorption equation:  a= oC1'"


                            a      1/n

                            2.46   0.177
Linner
 and Gortner,

 1935
                                     Experimental Conditions:  same as for acetic acid.

-------
                                                       TABLE 6:   Continued
     Compound Name
                                                                                                                 Ref.
       butyric acid

           C4H8°2
         Compound properties0
           m.w. 88.12
           m.p. -4.26°C
           b.p. 163.53°C
           density 0.95775°
           water sol  «°
Adsorbent
  activitated
    charcoal BIO
Adsorption equation:  y= a.x
                            x - range I
                            (mmol/dra )
                            0.08 - 7.18
                     a      b
                     0.878  0.4
Spahn  et  al.
 1974
CD
       n-butyric acid
Adsorbent
  XAD-2
    (amberlite resin)
                                                                 Adsorption equation:  — = zrr- + ^
                                                                 (Langmuir)
                                                                 K(25°C)
                                        b(25°C)
                                                                                         -3
                                                                 23.7 liter/mole  1.46X10   mole/g

                                                                 Enthalpy of adsorption:
                                                Gustafson
                                                 et  al.,
                                                 1968
                                                                 AH°= 2.303
                                                                 7X10~4 mole
                                                                 9X10 4 mole
                                      -AH°*
                                      4.1 kcal/mole

                                      2.4 kcal/mole
                                                                 1.2X10"3 mole  2.1 kcal/mole
     *AH decreases with increasing surface coverage, i.e. energetically
         preferred sites are utilized first.

-------
                                                  TABLE 6:  Continued
Compound Name
                                                                                                            Ref.
  caproic acid

      CH3(CH2)4C02H

    Compound properties

      m.w. 116.16a

      m.p. -2 to -1.5°Ca

      b.p. 205°Ca

      density 0.9274£°a

      water sol 0.4 gm/100 ml
Adsorbent

  nordite
    (decolorizing
       carbon)
Adsorption equation:  a=
                           _
     ago        6

     8.772  4.636    1.892



Adsorption equation:  a= a


     a      1/n

     3.03   0.175
                                                Linner
                                                 and Gortner,

                                                 1935
                                     Experimental Conditions:  same as for acetic acid.
  citraconic acid


      C5H6°4
    Compound properties

      m.w. 130.10a

      m.p. 91°Cfc

      density 1.617a

      water sol 238 cold
Adsorbent

  nordite
    (decolorizing
       carbon)
Adsorption equation:  a= °^_


     06     a        3
     1.356  1.014    1.337.
                       Adsorption equation:  a=


                            a      1/n

                            1.69   0.167
                                                Linner
                                                 and Gortner,

                                                 1935
                                     Experimental Conditions:  same as for acetic acid.

-------
                                                   TABLE 6:   Continued
Compound Name
                                                                       Ref.
  citric acid
      C6H8°7
    Compound properties

      m.w. 192.14a

      m.p. 153°C  (anhydrous)"2

      b.p. decompa

      density 1.542{ab

      water sol 133 cold gm/100 ml
Adsorbent

  nordite
    (decolorizing
       carbon)
                                                             Adsorption  equation:   a=  y^——
     aB     a        6
     1.444  2.757    0.524


Adsorption equation:  a= aC1//n


     a      1/n

     0.73   0.203
                                                Linner
                                                 and Gortner,

                                                 1935
                                     Experimental Conditions:   same  as  for  acetic  acid.
  dibromosuccinic acid

      C4H402BT2

    Compound properties

      m.w. 275.90

      m.p. 151-3°C
Adsorbent

  nordite
    (decolorizing
       carbon)
Adsorption equation:  a= °^
                            1.397  1.119
                                            1.248
                       Adsorption equation:  a= aC1/"
Linner
 and Gortner,

 1935
                                                                  a       1/n
                                                                  2.58   0.320
                                     Experimental Conditions:   same as for acetic acid.

-------
                                                  TABLE 6:  Continued
Compound Name
                                                                        Ref.
  formic acid

      HCO H

    Compound properties1'

      m.w. 46.03

      m.p. 8.4°C

      b.p. 100.7°C

      density 1.220^°

      water sol •>
Adsorbent

  nordite
    (decolorizing
       carbon)
Adsorption equation:  a=
agC
1+aC
     aB     a        B

     0.273  0.159    1.710



Adsorption equation:  a= aC1/"


     a      1/n

     2.47   0.435
Linner
 and Gortner,

 1935
                                     Experimental Conditions:  same as for acetic acid.
  fumaric acid

      C.H 0.
       444
    Compound properties

      m.w. 116.07fc

      m.p. 287°Cb

      b.p. 200 subl.fc
           165 subl.a
      density 1.6355ofc

      water sol 0.7025; 9.8looi
Adsorbent
  nordite
    (decolorizing
       carbon)
Adsorption equation:  a

     08     a        B
     7.097  5.798    1.224



Adsorption equation:  a= aC1//n


     a      1/n
     2.81   0.248
                       Linner
                        and Gortner,

                        1935
                                     Experimental Conditions:  same as for acetic acid.

-------
                                                  TABLE 6:  Continued
Compound Name
                                                                       Ref.
  glutaric acid


      C5H8°4

    Compound properties
      m.w. 132.lla

      m.p. 99°Ca

      b.p. 304 decomp.

      density 1.424i;5a

      water sol 642°a
Adsorbent

  nordite
     (decolorizing
       carbon)
Adsorption equation:  a=
                                                                 aB     a        B

                                                                 3.697  3.104    1.192
                       Adsorption equation:  a= aC


                            a      1/n

                            1.96   0.201
                                                  1/n
Linner
 and Gortner,

 1935
                                     Experimental Conditions:  same as for acetic acid.
  glyceric acid


      C3H6°4

    Compound properties'2

      m.w. 106.08

      b.p. disintegrates

      water sol «
Adsorbent

  nordite
    (decolorizing
       carbon)
                         a BC
Adsorption equation:  a= ,+
     06     a        B
     0.668  0.812    0.823



Adsorption equation:  a= aC1'"


     a      1/n

     1.29   0.267
Linner
 and Gortner,


 1935
                                     Experimental Conditions:  same as for acetic acid.

-------
                                                  TABLE  6:   Continued
Compound Name
                                                                                                             Ref .
  glycolic acid

      HOCH CO_H

    Compound propertiesc

      m.w. 76.05

      m.p. 80°C

      b.p. decomposes
Adsorbent

  nordite
     (decolorizing
       carbon)
                          n Rf
Adsorption equation:  a=  ,?



     aB     a         B

     0.239  0.249     0.958



Adsorption equation:  a=  aC-1-/11


     a      1/n

     1.54   0.390
Linner
 and Gortner,

 1935
                                     Experimental Conditions:   same  as  for  acetic  acid.
  glyoxylic acid


      C2H2°3
    Compound properties

      m.w. 74.04a

      m.p. 70-5°Ca
           (+l/2w)
           98 (anhydrous)

      water sol  very soluble
Adsorbent

  nordite
     (decolorizing
       carbon)
Adsorption equation:  a= °
     aB     a        6

     0.508  0.223    2.275



Adsorption equation:  a= aC


     a      1/n

     3.89   0.455
Linner
 and Gortner,

 1935
                                     Experimental Conditions:   same as  for  acetic  acid.

-------
                                                  TABLE  6:  Continued
Compound Name
                                                                                                            Ref -
isobutyric acid
(CH3) 2CHCO2H
Compound properties


nordite
carbon) a (3 a B
Linner
and Gortner,
1935
      m.w. 88.lf

      m.p. -46.1°Ca

      b.p. 153.7°Ca

      density 0.96815$°^  .949?°*

      water sol 20 20 gm/100 mlb
                            0.883  0.497    1.776
                       Adsorption equation:  a= aC


                            a.      1/n

                            2.36   0.273
                                                  ,1/n
                                     Experimental  Conditions:   same  as  for  acetic  acid.
  isovaleric acid
      C5H10°2

    Compound properties

      m.w. 102.13a

      m.p. -29.3°Ca

      b.p. 176.7°Ca

      density 0.9286$°a

      water sol 4.22oi
Adsorbent

  nordite
    (decolorizing
       carbon)
                                                            Adsorption  equation:   a=
                            1.630  0.902    1.807
Linner
 and Gortner,


 1935
                       Adsorption equation:  a= oC


                            o      1/n

                            2.51   0.227
                                                  ,1/n
                                     Experimental  Conditions:   same as for acetic acid.

-------
                                                   TABLE  6:   Continued
Compound Name
                                                                                                             Ref.
  itaconic acid
      C5H6°4
    Compound properties

      m.w. 130.10a

      m.p. 175°Ca

      b.p. decomposes

      density 1.632fc

      water sol 8.332oi
Adsorbent              Adsorption equation:   a= y£—

  nordite
     (decolorizing           	
       carbon)              a.&     a         0

                            1.167  0.904     1.291
                       Adsorption equation:  a=  ac1//n


                            a      1/n

                            1.54   0.148
                                                 Linner
                                                  and Gortner,

                                                  1935
                                     Experimental Conditions:   same  as  for  acetic  acid.
  lactic acid (DL)


      C3H6°3
    Compound properties

      m.w. 90.08a

      m.p. 18°Ca

      b.p. 122°Ca

      density 1.249 lsb

      water sol •»
Adsorbent

  nordite
     (decolorizing
       carbon)
Adsorption equation:  a= ° *••
                            0.437  0.415    1.054
                       Adsorption equation:  a= aC


                            a      1/n

                            1.66   0.335
                                                  1/n
Linner
 and Gortner,

 1935
                                     Experimental Conditions:   same  as  for  acetic  acid.

-------
                                                        TABLE 6:   Continued
Compound Name
                                                                                                                  Ref
CTi
           levulinic acid
            Compound properties
                         „
              m.w.  116.13

              m.p.  37.2 °Ca

              b.p.  246°C  slight decomp.a

              density 1.1335?oa? 1.1395j°fc

              water sol  very sol
Adsorbent

  nordite
    (decolorizing
      carbon)
                                                                   Adsorption equation:  a= y^*.,
                                                                                 2.990
                                                                                a
                                                                                2.289
                     8
                     1.307
                                                                   Adsorption equation:  a=ac  n
                                                                        a

                                                                        1.83
             1/n

             0.183
                                            Experimental conditions:  same as for acetic acid
                                                                                                                  Linner
                                                                                                                    and Gortner,
           maleic acid


              C4H4°4

            Compound properties

              m.w. 116.07a

              m.p. 139-140°Ca

              b.p. 135 decamp-^

              density 1.590?oi>a

              water sol 78.82S; 392.697-5fc
                                    Adsorbent

                                      nordite
                                         (decolorizing
                                           (carbon)
Adsorption equation :   a=

     06      a       B

     1.233   0.884   1.395
                                                                   Adsorption equation:  a=oC
                                                                        a       1/n
                                                                        1.90    0.203
                                                                     Linner
                                                                       and Gortner,

                                                                       1935
                                             Experimental conditions:   same as for acetic acid

-------
                                                 TABLE 6:   Continued
Compound Name
                                                                                                          Ref
malic acid (I)
C4H6°5
Compound properties
Adsorbent
nordite
(decolorizing
age

rvR n ft
Linner
and Gortner,
1935
     m.w. 134.09

     m.p. 100°C

     b.p. 140°C decomp.

     density 1.595

     water sol  very sol
  malonic acid
   Compound properties

     m.w. 104.06fc

     m.p. 135. 6°C subl.£

     b.p. decomp. at  140 °C

     density 1. 631,,1 sb;  1.619a

     water sol 61.1°0gm/100
               73.5 gm/100 ml
               92.650gm/100 ml
                                           carbon)
                                   0.531    0.574    0.927
                              Adsorption equation:   a=aC
                                                         1/n
                                   a      1/n

                                   1.28   0.252
                                    Exoerimental conditions:  same as for acetic acid
Adsorbent

  nordite
    (decolorizing
      carbon)
                                                                   Adsorption equation:   a=
                    agC
                    1+aC
aft      a       6

1.897   1.540   1.232
                              Adsorption equation: a=ctC  'n


                                   a       1/n

                                   3.88    0.410
Linner
  and Gortner,

  1935
                                     Experimental  conditions:   same as for acetic acid

-------
                                                      TABLE  6:   Continued
       Compound Name
                                                                                                                Ref
         mesaconic acid


            C5H6°4

          Compound properties

            m.w. 130.10a

            m.p. 204.5

            b.p. 250°C decomp.

            density 1.466$"g/ml^
            water sol 2.7 '
118'
             Adsorbent

               nordite
                 (decolorizing
                   carbon)
Adsorption equation :   a=
                                                                    ctBC
     aB      a       B

     2.706   1.886   1.435
Linner
  and Gortner,

  1935
Adsorption equation:  a=aC



     a       1/n

     1.80    0.133
                                                                     1/n
00
                                           Experimental conditions:   same as  for acetic acid
         methylsuccinic acid


            C5H8°4
          Compound properties

            m.w. 132.11

            m.p. 111°C

            b.p. decomp.

            density 1.410g/ml

            water sol 66.72 °
             Adsorbent

               nordite
                 (decolorizing
                   carbon)
Adsorption equation:  a=
                                                                    .
     ag      a       6

     0.664   0.608   1.092
                                           Adsorption equation:  a=aC



                                                a       1/n

                                                1.30    0.172
                                                                     1/n
Linner
  and Gortner,

  1935
                                           Experimental conditions:   same as  for acetic acid

-------
                                                 TABLE  6:   Continued
Compound Name
                                                                                                          Ref
  monobromosuccinic acid

     C4H504Br

   Compound properties
                fc
m.w. 197.00

m.p. 15

density 2.073

water sol 19
                  161°C

                  a
                               Adsorbent

                                 nordite
                                    (decolorizing
                                      carbon)
Adsorption equation:  a=
                         1+aC
     08      a       6
     0.934   0.643   1.451
                                                                   Adsorption equation:   a=ccC
                                                                        a       1/n

                                                                        1.82     0.195


                                    Experimental  conditions:   same  as  for acetic acid
  oxalic acid
     C2H2°4

   Compound properties

     m.w. 90.04a

     m.p. 189.5°Ca

     b.p. 157°C subl.a

     density 1.900i7<2

     water sol 19.515 gm/lOOml1
                               Adsorbent

                                 nordite
                                    (decolorizing
                                      carbon)
                                                                   Adsorotion eauation:  a=
                        Qt6C
                        1+aC
                                                                   0.440   0.332   1.325
                                                              Adsorption equation:  a=oC
                                                                                       1/n
               120'° gm/lOOml  (hydrated form)
                                                                   a       1/n

                                                                   3.62    0.551
Linner
  and Gortner,

  1935
Linner
  and Gortner,

  1935
                                    Experimental  conditions:   same as for acetic acid

-------
                                                  TABLE  6:  Continued
Compound Name
                                                                                                            Ref.
  propionic acid

      C3H6°2
    Compound properties
      m.w. 74.08
      m.p. -20.8°C
      b.p. 140.99'C
      density 0.993020
      water sol «°
Adsorbent
  nordite
     (decolorizing
       carbon)
Adsorption equation:  a= ?^

     06      a       3
     0.925   0.491   1.885
                       Adsorption equation:  a= aC
                                                   1/n
                            a       1/n
                            2.46    0.236
                                                Linner
                                                 and Gortner,
                                                 1935
                                     Experimental conditions:  same as for acetic acid.
  propionic acid
      C3H6°2
    Compound properties
      m.w.  74.08
      m.p.  -20.8°C
      b.p.  140.99'C
      density 0.993020
      water sol -
Adsorbents
  Activated
    charcoal BIO
Adsorption equation:  y= a-x
Adsorption constants:
                         x-range I
                         (mmol/dm )
                         0.1 - 8.3
                a     b	
               0.497  0.4
                                                Spahn
                                                 et  al.,
                                                 1974

-------
                                                   TABLE 6:   Continued
Compound Name
    Compound properties

      m.w. 88.06a

      m.p. 13.6°Ca
      b.p. 165°C slight decomp.

      density 1.2272?"

      water sol °°
       carbon)
                            a.6       a        B
                            0.979    0.585    1.674
                       Adsorption equation:   a=  ctC


                            a.        1/n

                            2.44     0.273
                                                                                       ,1/n
                                                                                                             Ref.
pyruvic acid
C3H4°3
Adsorbent
nordite
r* ft ("*
Adsorption equation: a= ]_+aC
Linner
and Gortner,
1935
                                     Experimental  Conditions:   same as for acetic acid.
  succinic acid

      C.H,0.
       464
    Compound properties

      m.w. 118.09

      m.p. 185°C

      b.p. 235°C dissint.

      density 1.564 I5  g/ml

      water sol 6.8 at 20°C
                121 at 100°C
Adsorbent
  nordite
     (decolorizing
       carbon)
Adsorption equation:  a= °

                            06      a        6

                            0.865   0.467    1.854
                       Adsorption equation:  a= aC
                                                   1/n
                            a.       1/n

                            2.44    0.273
Linner
 and Gortner,

 1935
                                     Experimental  Conditions:   same as  for acetic acid.

-------
                                                        TABLE 6:   Continued
        Compound Name
                                                                                                                 Ref
tartaric acid

   C.HC0
    466

 Compound properties

   m.w.  150.09^

   m.p.  100°C*

   density 1.697 ;  1.788a

   water sol 20.62ob; 9.23°
                                            Adsorbent

                                              nordite
                                                (decolorizing
                                                  carbon)
                                        185101
                              Adsorption equation:  a=    "
                                   aB      a       6
                                   0.322   0.468   0.687
                                                                          Adsorotion eauation:  a=aC
                                                                               a       1/n

                                                                               0.94    0.275
                                                                                                    1/n
                                  Linner
                                    and Gortner,

                                    1935
to
                                            Experimental conditions:   same as for acetic acid
         valeric acid
          Compound properties

            m.w.  102. 13a

            m.p.  -33.83°Ca

            b.p.  186.05°Ca

            density 0.939l5°a;  0.9425°*

            water sol 3.7gm/100ml
Adsorbent

  nordite
    (decolorizing
      carbon)
                                                                          Adsorption equation:  a= aC
                                                                                                     1/n
a       1/n

2.84    0.182
                              Adsorption equation:  a=
                                   a6      a        6

                                   1.878   0.872    2.154
                                  Linner
                                    and Gortner

                                    1935
                                            Experimental conditions:  same as for acetic acid

-------
                                                        TABLE 6:  Continued
Ui
U)
Compound Name
Acids, Aromatic
benzoic acid
Adsorbents Adsorption equation: —
C..H 0
762 Type BL -
Compound properties activated carbon orption constants:
(Pittsburgh ^
m.w. 122. 13a Chemical Co.)

m.p. 122.4°Ga Surface area Compound pjca
b.p. 249-C* 1000-1100 v /g benzoic acid 4.20
density 1.2659isi
-, n -.n^b -2,4-dichloro 2.76
water. sol 0.18* ,
n 0718°
u • *•• ' i,
2.27sb
-3-amino-2,5- 3.40
dichloro
(amiben)
-3-nitro-2,5- 3.23
dichloro

-2-methoxy-3,6- 1.94
dichloro
(dicamba)



= (TT§C)




pH of
so In.

3
7
11
3
7
11
3
7
11
3
7
11
3
7
11









a*

0.238
0.108
0.081
0.259
0.123
0.108
0.928
0.283
0.025
0.360
0.118
0.035
0.181
0.317
0.068









b

510
124
75
676
159
73
515
131
72
505
130
93
394
154
68
Ref

Ward and
Getzen,

1970



x/m
489
113
67
651
147
69
510
127
51
491
120
72
313
149
59
        *0nits:   a = liters/y mole

                 b = v moles/g
                 c = y moles/liter

                 — = p moles/g
                                            Experimental conditions:  100 ml aqueous acid solution:  lOmg  carbon

-------
                                                  TABLE 6:  Continued
Comoound Name
                                                                                                            Ref.
  benzole acid

      C7H6°2
    Compound properties
      m.w. 122.13°
      m.p. 122.4°ca
      b.p. 249°Cb
                    .,fc
      density 1.2659*
                    ufc
      water sol 0.18
                0.2718
                2.275
Adsorbent
  activated
    charcoal BIO
Adsorption equation:  y= a-x
                       Adsorption constant:
                         x-range I
                         (mmol/dm      a
                         0.1 - 6
                                       3.06   0.181
Spahn
 et  al.
 1974
  benzoic acid and
    substituted benzoic acids
      C7H6°2
Adsorbent
  charcoal,
    activated,
      200 mesh
Adsorption equation:
     log x/m = log k + 1/n log c
Hartman,
 Kern,
 Bobalek,
 1946
                                                                 1/n and log k Values
                                     Acids
                                     Benzoic
                                     o-Chlorobenzoic
                                     o-Aminobenzoic
                                     o-Hydroxybenzoic
                                     o-Toluic
                                     m-Toluic
                                     p-Toluic
                                                                                   log k
1/n
0.3680
0.4060
0.3693
0.3840
0.3879
0.3581
0.3696
20°
0.0613
0.2208
0.3472
0.2700
-0.0215
-0.0092
0.1351
30°
0.0265
0.1834
0.3031
0.2385
-0.0719
-0.0582
0.0762
40°
-0.1091
0.1303
0.2678
0.2091
-0.2510
-0.1791
-0.0324
50°
-0.2551
0.0936
0.2218
0.1844
-0.5232
-0.3732
-0.1886
                                                            Adsorption from benzene solutions.

-------
TABLE 6:  Continued
Compound Name
phenyl acetic acid
Adsorbent
C6H5CH2C02H Activated
Compound properties" charcoal
m.w. 136.16
m.p. 77°C
b.p. 265. 5°C
density 1.091J7; 1.228"
water sol slightly sol. BIO
LW
Lev 634
BD
Dl
D2
B2
LS- supra
Decaka 9
106/427/1
106/427/5
106/427/3






Adsorption equation:

y= a

b
• x


Ref .
Spahn
et al.,
1974
Adsorption constants:
x-range I
(mmol/dm )
0
0
0
0
0
0
0
0
0
0
0
0
.1 -
.05 -
.1 -
.1 -
.05 -
.1 -
.1 -
.1 -
.1 -
.1 -
1 —
1 —
10
12
8
22
7
8
11
7
8
7
6.5
8
a
2
1
0
1
1
1
1
1
1
1
1
2
.51

.84
.14
.93
.57

.75
.82
.53
.87
.08
b_
0.
0.
0.
0.
0.
0.
0.
0.
0.
0.
0.
0.
x-range II
(mmol/dm )
16
165
38
15
162
245
145
18
03
11
144
244
0

0




0

0
0
0
.001 - 0.1

.01 - 0.11




.001 - 0.31

.001 - 0.12
.001 - 0.11
.001 - 0.12
a 	 b
2.6 0.32

1.76 0.56




1.53 0.23

2.05 0.33
1.85 0.3
2.6 0.44

-------
                                                  TABLE 6:  Continued
Compound Name
Carboxylic acids, aromatic
Phenoxyacetic acid
Adsorbents Adsorption equation:
C H 0
883 Type BL -
Compound properties ^Pittsburgh"60" Adsorption constants:
m.w. 152.14 Chemical Co.)

oqo,-. Surface Area 9 Compound pka
p- 1000-1100 v /g
b.p. 285 °C slight decomp. Phenoxyacetic ^ ^

water sol 1.2 10
-4-chloro- 2.36
Ul
CTv
-2,4-dichloro- 3.31


-2,4,6-
trichloro- 3.35


2,4-dichloro- 3.92









x _ abC
Iff" (1+aC)



pH of
soln.

3
7
11
3
7
11
3
7
11

3
7
11
3
7
11




a*

0.423
0.229
0.209
0.362
0.101
0.115
0.279
0.112
0.070

0.672
0.095
0.073
0.431
0.125
0.100




b

446
105
64
575
198
145
629
223
154

676
239
144
645
235
59
Ref .

Ward and
Getzen,
1970


X
m

436
86
43
560
180
133
607
205
135

666
216
127
630
218
54
                                     Experimental Conditions:

                                       10 mg carbon.
100 ml aqueous acid solution:
Units:  a = liters/y mole

        b = v moles/g

        c = v moles/liter


       — = v. moles/g
        m

-------
                                                TABLE 6:  Continued
Compound Name
                                                                                                                  Ref.
  2,4-dichloro-
    phenylacetic acid
*Units:  a = liters/y mole
         b = y moles/g
         c = y moles/liter
         — = y moles/g
         m
                                  Adsorbents

                                    Type BL -
                                      activated carbon
                                      (Pittsburgh
                                        Chemical Co.)

                                    Surface area
                                      1000-1100 vVg
Adsorption equation:  — =/fi~r>
Adsorption constants:


Pjca

3.92
Hard and
 Getzen,

1970
pH of
so In.
3
7
11
a*
0.431
0.125
0.100
b
645
235
59
x/m
630
218
54
                                  Experimental conditions:  100 ml aqueous acid solution:  10 mg carbon

-------
                                                        TABLE 6:   Continued
un
CO
Compound Name
Alcohol
n-butyl alcohol Adsorbent
C4H9OH Graphite
Compound properties Blood Char.
m.w. 74.12G
m.p. -90°CC
b.p. 117-118°CC; 117.71°Cfo
density 0.810?°c
water sol 7.9 gm/100 ml


Ref .
Adsorption equation: — = —(l+N.v./N v ) Bartell,
m m b b a a Thomas,
„ , , . . and Fu,
N = mole fraction
v =
a =
b =
t°C
0
25
45
0
25
45
partial molar volume 1951
solvent
solute
AF°** AH0***
K* kcal/mole kcal/mole
63.3 -2.24 -0.16
61.6 -2.43 -1.47
52.7 -2.50
477 -3.34 -0.94
412 -3.54 -0.52
390 -3.76
     *Equilibriuin  constant K obtained from the limiting slope of
      the adsorption  isotherms at zero concentration
     **AF° = -RT  In K

                tT T   1
     ***AH° = R'  2 1
\m _

(2 X
                        In  K-
                           _ ~

                           K,

-------
                                                         TABLE  6:   Continued
Ul
Compound Name
Amides

acetanilide and derivatives,
adsorption from 2% ethanol
C0H0ON
8 9
Compound properties
m.w. 135.16
ra.p. 114°C

b.p. 305°C

density 1.21JJ
water sol 0.56325,- 3.580














Compound
ff-Ethylacetanilide
4 -Hydroxy acetanilide
Acetanilide

2-Chloroacetanilide
4-Aminoacetanilide
flf-n-Butylacetanilide
2-Nitroacetanilide
2 -Hydroxyacetani 1 ide
tf-Phenylacetanilide
4-Chloroacetanilide
3 , 4-Dichloroacetanilide
4-Nitroacetanilide
4-Bromoacetanilide
2 , 5-Dichloroacetanilide


Adsorption


solubility
(x 10" 4M)
2% ethanol
2320
1580
624

375
352
167
138
32
31
16
12
11
11
10


equation:



V
0.05
0.25
0.21

0.25
0.06
0.23
0.16
0.26
0.26
1.19
6.05
1.02
1.73
0.92
Ref .

(s> = Kcl/n
Ward and
1/n = 1 Upchurch,
1965
V*
0.20
0.13
0.32

0.47
0.05
0.89
0.72
0.15
1.59
2.64
6.83
2.18
3.30
1.59
                                            Method of analysis:   UV spectrophotometry with Beckman DO spectrophotometer
       * k,, = adsorption  on  nylon



      ** k  = adsorption  on  cellulose  triacetate

-------
                                                        TABLE 6:  Continued
(Ti
O
Compound Name
aniline and derivatives,
adsorption from 2% ethanol
C..H NH
D J ^
Compound properties Compound
m.w. 93.13a Aniline
m.p. -6.3°Ca 2-Methylaniline
4-Methylaniline
b.p. 184.13°Ca tf-Methylaniline
density 1.02173?°a 4-Chloroaniline
water sol 3.4^; 6.4^ 2-Chloroaniline
ff-Ethylaniline
2-Nitroaniline
N , ff-Dimethylaniline
2 , 3-Dichloroaniline
3 , 4-Dichloroaniline
2 , 5-Dichloroaniline
4-Nitroaniline
tf-n-Butylaniline
2-Nitro-4-chloroaniline
2 , 4-Dinitroaniline
N- Ben zylani line
N- Phenylanil ine

Adsorption
solubility
(x 104M)
2% ethanol
4450
1670
1240
560
520
450
250
103
95
85
52
49
38
16
9
5
4
3

equation;
V
0.07
0.10
0.05
0.24
0.68
0.55
0.32
0.91
0.52
3.45
4.32
3.78
1.10
1.42
3.70
1.94
3.46
16.50
Ref .
: (-) = KC1/n; Ward and
m Opchurch,
1/n = 1
1965
V*
0.27
0.44
0.50
0.92
3.31
1.94
1.10
2.84
2.12
7.20
10.20
11.20
3.40
6.55
7.80
5.65
19.48
24.00
                                         Method of analysis:  UV spectrophotometry with Beckman DU spectrophotometer.
           =  adsorption on nylon

           =  adsorption on cellulose triacetate

-------
                                                  TABLE  6_J	Continued
Compound Name
2
(di-R,) aniline
SD R R
11830 CH3 CH3
12639 C2H5 CH3
11831 C3H7 CH3
13207 C2H5 C2H5
12030 C3H? C2H5
12346 C3Hy C3H?
12400 CH-. iso-C,H.

Adsorption

Ripperdan
1% O.m
125
230
500
320
750
1170
222
Ref .
Lambert ,
equation: In K = aPAU*
1967
K values
soil Sacramento soil
5% O.m
145
193
520
269
702
-

*K  = equilibrium constant, estimated from adsorption data
 AU
ILL——,  P = parachor, P= density of the liquid, y = surface tension, M = molecular weight
  P
 difference in internal pressures of the solvent phases

-------
                                                        TABLE  6:   Continued
CT>
Compound Name
crystal violet
(gentian violet)
C25H30C1N3
Compound properties0
m.w. 408.06
water sol soluble
Amino acid
dl-tryptophan, from aqueous
urea solution
C11H12N2°2
Compound properties
m.w. 204.22
m.p. 283-5°C
water sol slightly sol cold
sol hot




Adsorbent
activated
charcoal


Adsorbent
carbon black
Urea
Concentration
H
0
0.11
1.01
3.05
5.03
7.07

Adsorption
BIO
Adsorption
x-range I
(mmol/dm
0.1 - 2
Adsorption
Ref .
Spahn
equation: y= a- x et al.
1974
constants:
a b
0.84 0.09
^_ Nogami, Nagai,
J.TDL
1968
1? AF AH AS fiSt ASS
10 J liter 10 J liter Real Kcal _ „
mole mole
1.63 1.70
1.60 1.70
1.54 1.08
1.28 0.615
1.18 0.472
0.92 0.397
mole mole - - - -
-4.45 0.22 15.4 0 15.4
-4.45 — 15.4 0.05 15.4
-4.18 — 14.5 0.38 14.9
-3.87 — 13.5 1.15 14.7
-3.70 — 12.9 1.68 14.6
-3.57 — 12.5 2.08 14.6
     AF = free energy change


     AS = entropy change


     AS  = AS + AS.
       s          *c


     AS.  = entropy change of the transfer of tryptophan  from

             aqueous solution to aqueous urea solution


     e.u. = entropy units

-------
                                                  TABLE 6:  Continued
Compound Name
                                                                                                            Ref .
Benzene
  benzene - adsorption from
    binary mixture

      C6H6
    Compound properties
      m.w. 78.11d
      density . 87901fc
      m.p. 5.5°Ce
      b.p. -80.1°Ce
      water sol 820 ppm at 22°C-'
        OCT/water part coeff 130s
    Solvent
    Ethylene dichloride
    Cyclohexane
    Carbon tetrachloride
                                     Adsorbent
                                                            Adsorption equation:
                                                               X1X2  =  1
                                                              n°AX/m
                                                             K
                           Graphon                18.5
                           Spheron 6               5
                           Coconut shell charcoal 19.9
                           Decolorizing charcoal  16.4
                           Decolorizing charcoal  16.1
                           Coconut shell charcoal 18.2
Area of
adsorbent
m2/g
119
57
677
596
374
350
(AH£ - AH°*
cal/g
0. 54
-
12.0
7.1
4 .0
3.8
                                                                                                  Zettlemoyer
                                                                                                   and Micale,
                                                                                                   1971
 K = exp-(
AHa
RT
                ASa,

-------
                                                   TABLE 6:   Continued
Compound Name
Carbamates
carbamate derivatives,
adsorption from 2% ethanol
RlNHCOOR2

Adsorption


equation :


x. _
1/n
solubility , t
Compound 2% ethanol ^1




















Ethyl-tf-methyl-ff-phenyl
Ethyl-ff-benzyl
Ethyl-ff-phenyl
Ethyl-ff-ethyl-ff-phenyl
Ethyl-ff-(2-nitrophenyl)
ff-Phenylglycine ethyl ester
Phenyl
Isopropyl-ff-phenyl
Ethyl-ff- (4-chlorophenyl)
Ethyl-ff-butyl-ff-phenyl
n-Butyl-ff-phenyl
Ethyl-ff-(4-nitrophenyl)
Ethyl-ff-benzyl-/V-phenyl
Ethyl-ff- ( 2 , 5-dichlorophenyl)
Ethyl -ff- (2 , 3-dichlorophenyl)
Ethyl-ff , ff-diphenyl
Isopropyl-ff- (2-methyl-5-
chlorophenyl)
Methyl-ff- (2 , 4-dichlorophenyl)
Isopropyl-ff- (3-chlorophenyl)
Isopropyl-ff- (3 , 4-dichlorophenyl)
172
121
96
78
71
64
28
16
9.6
8.5
8.5
5.7
2.9
2.6
2.5
1.7
1.6
0.72
0.50
0.32
0.22
0.49
1.03
0.25
0.90
0.16
0.40
1.16
5.70
0.80
2.20
3.65
1.85
4.00
3.65
1.02
3.37
15.10
9.00
23.00
Ref .
Ward and
KC1/" Upchurch,
= 1 1965
V*
1.42
2.03
3.68
1.83
3.25
0.83
0.58
4.95
14.70
6.75
9.62
8.75
12.65
19.40
27.90
9.10
14.00
—
8.45
—
                                      Method of  analysis:   UV spectrophotometry with Beckman DU spectrophotometer




 *kN  = (amount adsorbed/weight of nylon) / (C1//n)



**,  = (amount adsorbed/weight of cellulose triacetate)/(C /n)

-------
                                                   TABLE 6:   Continued
Compound Name
                                                           Ref.
  carbamate derivatives,
    adsorption from 2% ethanol
          Adsorption equation:  ^
                                                                                       KC

(1/n = 1)
Hard and
 Upchurch,

 1965
                                  Adsorbent
                                  Nylon
                                    (Zytel-101)
                                    (80 mesh)
Compound
Ethyl-ff-phenyl
Isopropyl-JV-phenyl
Ethyl-ff-methyl-JV-phenyl
Ethyl-/»-ethyl-»-benzyl
Ethyl-ff-benzyl-Af-phenyl
Ethyl-ff,»-diphenyl
Isopropy1-ff-(3-chlorophenyl)
Ethyl-ff-(2-nitrophenyl)
Ethyl-JV- (4-nitrophenyl)
Ethyl-ff-(2,3-dichlorophenyl)
10"C
1.03
1.16
0.22
0.25
1.33
0.66
9.00
0.75
3.65
3.70
26.5°C
1.03
1.16
0.22
0.25
1.85
1.02
9.00
0.90
3.70
3.70
50°C
1.03
1.16
0.22
0.25
1.85
1.02
9.00
0.90
3.70
3.70
                                 Method  of  analysis:   UV spectrophotometry with Beckman DU spectrophotometer.

-------
                                                       TABLE 6:   Continued
     Compound Name
                                                                                                                 Ref.
     Carbonyls

       acetophenone

           C,HCCOCH,
            65    3

         Compound properties

           m.w.  120.16h

           m.p.  20.5°Ch

           b.p.  202.0°Ch

           density 1.0281 at 20°C/4°C?I

           water sol   5.6xlO~3M at 25°C1
Adsorbent

  activated
    charcoal B 10
Adsorption equation:  y= a-x
                       Adsorption constants:
                       x-range I
                       (mmol/dm )
                       0.1 - 4
                                      3.46    0.155
Spahn
 et  al.,

 1974
CTi
     N-Heterocyclics

       benzo[f]quinoline

           C13H9N

         Compound  properties

           m.w.  179.22

           m.p.  93.5°C

           b.p.  350°C  (721  torr)
                202-5°C (8 torr)

           vapor pressure at 20°C (torr)

           water sol  ( pg ml"1)
                    76.112.2

     *TOC  - total organic  carbon

     **CEC  - cation exchange capacity
Adsorbent

  Coyote Creek
    sediment
                       Adsorption equation:  S  = K S  , n=l
                       TOC*
1.4
                                CEC*
         13.5
                   13131170
                                                Smith, Mabey,
                                                 Bohonos,  Holt,
                                                 Lee, Chou,
                                                 Bomberger, Mill,

                                                 1977

-------
                                                  TABLE 6:  Continued
Compound Name
                                                                                                            Ref.
  9H-carbazole

      C,H.HHC,H.
       b 4   64
    Compound properties

      m.w. 167.21

      m.p. 247-248°C

      water sol (1.0 pg/ml)
                       Adsorption equation:  Cg = KpCw
Adsorbent
Ca-montmorillonite     3.20±1.06

Coyote creek sediment  175 ±20.9
                                                Smith, Mabey,
                                                 Bohonos,  Holt,
                                                 Lee,  Chou,
                                                 Mi11,  Bomberger,

                                                 1977b
  7H-dibenzocarbazole (DBC)


      C10H6NHC10H6
    Compound properties

      m.w. 267.31

      m.p. 155-159°C

      water sol 2.4X10~7M
Adsorbent

Des Moines River
  sediment

Coyote Creek
  sediment

Searsville Lake
  sediment
  *TOC = total organic carbon

 **CEC = cation exchange capacity

***Based on analysis of the supernatant at equilibrium
                       Adsorption equation:  C  = KDCW
                       TOC*
0.8
1.9
                                                            5.0
                                CEC*
         10.5
         13.5
                                                                     34.5
                   32,600
                   18,500
                                                                               27,600
                                                Smi th,  Mabey,
                                                 Bohonos,  Holt,
                                                 Lee, Chou,
                                                 Mill,  Bomberger,

                                                 1977a

-------
                                                        TABLE 6:   Continued
      Compound Name
                                                                                                                 Ref.
        pyridine

            C5H5N

          Compound properties'^

            m.w. 79.10

            m.p.  42.0°C

            b.p. 115.3°C

            density .982 at 20°C

            water sol  -
Adsorbent

  activated
    charcoal B 10
Adsorption equation:  y= a-x



x-range I

|mmol/dm )       a       b

0.14 - 7.4     1.22    0.2
                                                                       Spahn
                                                                        et  al.

                                                                        1974
CD
        pyridine
                                                                 Adsorption  equation:
                      X = KCen, X = mg/g;

                      Ce = mg/1
                                                                       Baker and
                                                                        Luh,

                                                                        1971
Temp.
1°
24°
1°
24°
EM
2
2
2
2
K
0.03
0.01
0.12
0.06
n
1.01
1.03
1.04*
1.02
                                           Adsorbent
                                          Na-kaolinite
                                          Na-montmorillonite
                                          Method of  analysis:   liquid  scintillation  with  Packard  Tri-Carb  spectrometer
                                                                   4
     Note:  clay:  pyridine ratio was varied  from  12.15  to  6.25x10
                   for ratio  (12.15) effect of pH  was  studied:
                      max adsorption for Na-kaolinite  was found at pH  5.5;  pka  pyridine = 5.25
                      max adsorption for Na-montmorillonite was found  at  pH 4.0

     •discrepancy noted between data given Table 2 p.842 and regression equation  p.843, believe
      this correct value.

-------
                                                  TABLE 6:  Continued
Compound Name
                                                                                                            Ref.
  quinoline

      C9H7N

    Compound properties

      m.w. 129.15

      water sol 6.11 yg/ml

      pKb - 9.5*

      m.p. -14.5°C

      b.p. 161.9°C
                       Adsorption equation:
  _
p
                                    adsorbed ,ug in solution
Adsorbent
                       TOC

                       0.05
Ca-montmorillonite

Coyote Creek sediment  1.4
   CEC

   69

   13.5
  V



7.28+0.52

10.9±0.4
                                                  ml
                                     Experimental conditions:  quinoline concentrations 4 and 8 p.g/ml
                                         sediment concentrations 1000 to 3000 times that of quinoline.
                                                                                                     -1
Smith,
 Mabey,Bohonos,
 Holt, Lee,
 Chou, Mill,
 Bomberger,

 1976b
                                     Method of analysis:  0V spectrophotometry with Gary Model 11
                                         spectrophotometer.
      *Quinoline is calculated to be 97%, 24%, and 0.32% protonated
       at pH 3,  5,  and 7, respectively.

-------
                                                      TABLE 6:  Continued
      Compound Name
                                                                                                                 Ref.
-J
O
      S-Heterocyclics

        ben zo[b]thiophene


           C8H6S

         Compound properties

           m.p. 31.3°C

           b.p. 212.9°C

           water sol 127.3±2.5 at 20°C
Adsorbent
  Coyote Creek sediment
                              Adsorption equation:  S =K S ,  n=l
                              TOG     CEC      £

                              1.4     13.5    50±5
                                           Experimental conditions:  sediment loadings of 2000:1 and
                                             5000:1 sediment: BT by weight
                                         Smi th,  Mabey,
                                          Bohonos,  Holt,
                                          Lee,  Chou,
                                          Mill,  Bomberger,

                                          1976c
        dibenzothiophene

           C12H8S

         Compound properties

           m.w.  184.27

           m.p.  99-100°C

           b.p.  332-333°C

           water sol 1.11±0.09
                              Adsorption equation:  S =K S , n=l
Adsorbent
  Coyote Creek sediment
Toe

1.4
CEC

13.5
                                             1380±130
Smith,  Mabey,
 Bohonos,  Holt,
 Lee, Chou,
 Bomberger,  Mill,

 1977

-------
                                                TABLE  6:  Continued
Compound Name
Phenols
phenol
C6H5OH
Compound properties
m.w. 9411d
m.p. 40.9°Ce
b.p. 180°C/740mmk
density 1.072 g/ml2*
!•
Ref.
Adsorption equation: y=a- x Spahn
et al.,
Adsorbent
X- range I 1974
activated charcoal (mmol/dm3) a b
D XU
0.1-8 2.16 0.23
X-range II
(mmol/dm ) a b
0.001-0.06 3.6 0.39
     water-sol 84.12 mg/ml
Polynuclear aromatics

  benz[a]anthracene


     C18H12

   Compound properties

     m.w. 228.28

     m.p. 155-7°C

     b.p. (at 760 torr)
            435°C

     water sol at 27°C
Adsorbent

  Coyote Creek
    sediment
                              Adsorption equation:  s =K S ,  n=l
                                                     s  p w
TOC      CEC
K
_£_
1.4      13.5      26,200±1700
Smith,  Mabey,
 Bohonos,
 Holt,  Lee,
 Chou,  Bomber-
 ger. Mill,

 1977

-------
                                                 TABLE  6:   Continued
Compound Name
benzo[a]pyrene
C20H12
Compound properties
m.w. 252. 32a
m.p. 178°CZ
b.p. ^500°C
311°C at 10 torr
water sol 1.2±0.1 ng/ml
pyrene
C16H10
Compovind properties
m.w. 202 l
m.p. 150°CZ
b.p. 393°CS
density 1.1271a
water sol .135±.005 mg/lm
Oct water part coeff:
KOW=150,000

Ref
Adsorption equation: x=K C Smith, Mabey
P Bohonos ,
K Holt, Lee,
Total organic CEC _•, ^> _4 rhon Mill
Adsorbent carbon {%) meg. lOOg (xlO q) Bobber go r
Ca-montmorillonite 0.06 69.0 1.7+0.5
1976a
Des Moi-nes River 0.6 10.5 3.512.7
Coyote Creek 1.4 13.5 7.6+2.4
Searsville Pond 3.8 34.5 15.0+2.2
Groszek,
Adsorption equation: | = ^ + |^ ^^
q = heat evolved when the [cyclohex] is c
q° = total heat evolved when complete
Equilibrium constants:
Est. from the Est. from heat AF** AH
Adsorbent Langmuir isotherm* of ads. data Kj/mole Kj/mole
graphon 2200
oleophilic graphite 5930
"polar" graphite 2300
1750 18.7 23
4800 21.1 18
2340 18.9 26
                                     Method of analysis:   UV  spectrophotometry with Onicam SP 500
                                         spectrophotometer.
 *at 21°

**AF° = -RTlnK

-------
                                                  TABLE  6:  Continued
Compound Name
                                                                                                             Ref.
  pyrene

    Compound properties

      water sol (mole fractionXlO )=12

      Koctanol water=150,000

                                     Adsorbent
                                       Hickory Hill

                                         sand
                                         coarse silt
                                         medium silt
                                         fine silt
                                         clay

                                       Doe Run

                                         sand
                                         coarse silt
                                         medium silt
                                         fine silt
                                         clay

                                       Oconee River

                                         sand
                                         coarse silt
                                         medium silt
                                         fine silt
                                         clay
Adsorption equation:
                      X=K C;
                                                            % O.C.
0.13
3.27
1.98
1.34
1.20
0.086
2.78
2.34
2.89
3.29
0.57
2.92
1.99
2.26
Karickhoff,
 Brown, and
 Scott,

 1979
                  KOC(X10
                          5
42
3000
2500
1500
1400
9.4
2100
3000
3600
3800
68
3200
2300
2500
0
0
1
1
1
0
0
1
1
1
0
1
1
1
.32
.92
.3
.1
.2
.11
.76
.3
.2
.2
.12
.1
.2
.1
                                     Experimental conditions:  sorbent concentrations 400 mg/ml of suspension
                                         for sand, 20 mg/ml for coarse and medium silt, 10 mg/ml for fine silt
                                         and 1 mg/ml for clay.

                                     Method of analysis:  UV spectrophotometry with Perkin Elmer 356
                                         spectrophotometer.

-------
                                                   TABLE 6:  Continued
Compound Name
Quinone
alizarin
C14H8°4
Compound properties'2
m.w. 240.23
m.p. 289-90°C (cor)
Ref .
Adsorbent
activated Spahn
charcoal Adsorption equation: y= a- x et al.,
B 10
1974
Adsorption constants:
x-range I
(mmol/dm ) a b
0.1 - 8 1.39 0.095
      b.p. 430°C  (sub)



      water sol  slightly sol









Sulfonate



  sodium naphthalenesulfonate
                                                                                   C   1    C
                                     Adsorbent              Adsorption  equation:   — = zrr- + T-
                                         -                                          CJ   JS.D   D

                                       Amberlite XAD-2
                                                                    AH°*      AFu0** ASu"***

                                                  	       Kcal/mole   Kcal   Kcal



                                      25°C     319      4.58X10"5    -4.4       -5.7   +4.4



                                      Method  of  analysis:   UV spectrophotometry
                                                                                                             Gustafson

                                                                                                              et   al.,



                                                                                                              1968
  *AH° = 2.303 RT,T2   (LogK^-logK')
 **fiFu° = RTlnK; K=55.5K; K=e/(l-6)C;  e=fractional  surface coverage



***ASU° = (AH°-AFu°)/T

-------
                                                         TABLE 6:  Continued
-J
LH
Compound Name
Carbamates
carbaryl
tf-methyl-1-naphthylcar hamate
C12H11N°2
Compound properties^ Adsorbent

PESTICIDES
Desorption
Adsorption
pH %o.m
m.w. 201 Lakeland s 5.3 0.22
water sol 350 pmol/1 Norfolk Is 6.0 0.57
Norfolk scl 5.4 0.15
Cecil si 6.3 1.77
Cecil c 5.7 0.53
Okenee si 4.65 5.16
Method of analysis: UV spectrophi
Chlorinated hydrocarbons Ad
DDT
1, l'-(2, 2,2-trichloroethylidene)-
bis [4-chlorobenzene]
C14H9C15
Compound properties
Adsorbent
illite 2.
kaolinite 7.
montmorillonite 1-
Ref .
LaFleur,
Equation: K, = P /P
b s w 1976a
Equation : K, = P /P
M f s w
1/0.5 1/1 1/2 1/4 1/1
0.44 0.21 0.16 0.13
1.4 0.36 0.31 0.25
0.72 0.12 0.10 0.08
5.2 1.8 1.6 1.3 0.79
0.88 0.27 0.22 0.19
7.6 3.7 2.6 2.3
atometry .
faorption equation. x/m KL Huang and
Liao,
K 1/n 1970
72xlO~3 3.28
37xlO~6 5.08
10xlO~5 5.97
           m.w. 354.49
                                                       Method of analysis:  GC - electron  capture

-------
                                                        TABLE 6:  Continued
      Compound Name
                                                                       Ref .
        dieldrin
            1,2,3,4,10,10-hexachloro-
            6,7-epoxy-l,4,4a,5,6,7,8,8a-
            octahydro-endo-1,4-eio-5 , 8-
            dimethanonaphthalene

            C12H8C16°
          Compound properties
            m.w. 380.91
Adsorbent
illite
kaolinite
montmorillonite
                       Adsorption equation:  - = KG1'"
                                                                  9.45X10
                                                                  1.46X10
                                                                  1.05X10
-16
-21
-16
 8.82
11.63
 9.24
                                         Huang and
                                          Liao,
                                          1970
CTl
                                           Method of analysis:   GC-electron capture.
      heptachlor
            1,4,5,6,7,8,8-heptachloro-
            3a,4,7,7a-tetrahydro-4,7-
            methano-1S-indene
                                                                  Adsorption equation:     =
                                                                       Huang and
                                                                        Liao,
                                                                        1970
            C10H5C17
                                           Adsorbent
                                           illite
                                           kaolinite
                                           montmorillonite
                           K
                       1.09X10
                       5.00X10
                       1.48X10
-9
-6
-4
1/n
 6.07
 4.51
 3.52
                                           Method of analysis:   GC-electron capture.

-------
                                                        TABLE 6:  Continued
-O
-J
Compound Name
methoxychlor
C16H15C13°2
Compound properties0 Adsorbent





Ref .
Karickhof f ,
Adsorption equation: X = K C; KOC = K /OC Brown, and
p p Scott,
% O.C. Kp KOC(X10"5) 1979
m.w. 345.65 Hickory Hill
m.p. 78-78. 2°C or sand
86-88°C coarse
medium

silt
silt
insol. in water fine silt
clay
Doe Run
sand
coarse
medium



silt
silt
fine silt
clay

0.
3.
1.
1.
1.

0.
2.
2.
2.
3.
13
27
98
34
20

086
78
34
89
29

53
2600
1800
1400
1100

8.3
2200
1700
2300
2400

0.
0.
0.
1.
0.

0.
0.
0.
0.
0.

41
80
91
0
92

097
80
73
80
73
Oconee River
sand
coarse
medium

silt
silt
fine sand
clay

0.
2.
1.
2.
-
57
92
99
26
-
95
2500
2000
2100
—
0.
0.
1.
0.
-
17
86
0
93
-
                                           Experimental conditions:  sorbent concentrations 400 rag/ml of suspension
                                               for sand, 20 rag/ml for coarse and medium silt, 10 mg/ml for fine silt
                                               and 1 mg/ml for clay.

                                           Method of analysis:  UV spectrophotometry with Perkin Elmer 356
                                               spectrophotometer.

-------
                                                      TABLE 6:  Continued
Compound Name
mirex
C10C112
Compound properties
m.w. 546.0
m.p. 485 (decomp)
Ref
Adsorption equation: S = K S , n=l Smith, Mabey,
s P w Bohonos,
Holt, Lee,
Chou, Bomber'
Adsorbent TOC CEC K ger. Mill,
_E
Coyote Creek 1977
sediment 1.4 13.5 460,000 ± 110,000
            vapor pressure
              at 50°  torr
                6 x 10~6

            water sol at 22 °C

              (pg/ml)
                70±20
CD
       Organophosphates

         aminoparathion


            C10H16N°3PS
            0,0-diethyl 0-p-aminophenyl
            phosphorothioate

          Compound properties

            m.w. 261.3

            water sol 390.0  vg/ml
Adsorbents

  Na-montmorillonite*
  Ca-montmori1lonite *

  Fe-montmorillonite*
                            Adsorption equation:  x/m = KC
                                                           1/n
1/n

0.954
1.151
K

46.3

43.3
>99.9%
 adsorption
                                             Experimental  conditions:   450 mg  clay  in  30 ml  aqueous
                                               insecticide solution

                                             Method of analysis:  GC -  alkali  flame ionization  detector

       *Prepared from Wyoming bentonite, <2  vm fraction
                                           Bowman and
                                             Sans,

                                             1977

-------
                                                  TABLE 6:  Continued
Compound Name
                                                                                                             Ref.
  fenitrothion
      0,0-dimethyl 0- (3-methyl-4-
      nitrophenyl) phosphorothioate
                       Adsorption equation:
                                               = KC
                                                    "L'n
Bowman
 and Sans,
 1977
    Compound properties
      m.w. 277.2
      b.p. 118°C
      density 1.3227g5
      water sol 25.4  ug/ml
Adsorbent              1/n
Na-montmorillonite*    1.163
Ca-montmorillonite*    1.952
Fe-montmorillonite*    1.773
                                           K
                                           71.1
                                           64.0
                                          740.1
                                     Experimental conditions:  same as for aminoparathion.
                                     Method of analysis:  GC-alkali flame ionization detector.
  methyl parathion
      0,0-dimethyl 0-p-
      nitrophenyl phosphorothioate
                       Adsorption equation:   *- = KCe1//n
                                                                       Bowman
                                                                        and Sans,
                                                                        1977
    Compound properties
      m.w. 263.2
      m.p. 37-38°Cc
      density 1.3585°°
      water sol 45.0 yg/ml
Adsorbent              1/n
Na-Montmorillonite*    1.032
Ca-Montmorillonite*    1.663
Fe-Montmorillonite*    1.463
                                           K
                                           65.4
                                           56.3
                                          147.3
                50 ppm

*Prepared from Wyoming  bentonite  <2  pm  fraction.
Experimental conditions:  same as for aminoparathion.
Method of analysis:  GC-alkali flame ionization detector.

-------
                                                       TABLE  6:   Continued
      Compound Name
                                                                                                                 Ref .
CO
O
methyl parathion
    0,0-dimethyl 0-p-
    nitrophenyl phosphorothioate
         Compound properties
           m.w.  263.12
                                   Sediment
                                   Ca-montmorillonite
                                   Coyote Creek

                                   Searsville Pond
                                   Navarro River
                                   Des Moines River
                                   Oconee River
                                                                 Adsorption  equation:
                                                                      K
                                                                             substate  in  solution
                                                                                                   'n
                                                                       P

                                                                       n =  1.0
                                                                                ml  solution
                                                                  46.1
                                                                  50.6
                                                                  55.0
                                                                  60.3
                                                                  47.6
                                                                  41.6
                                                                  23.6
                             Smith,  Mabey,
                              Bohonos,  Holt,
                              Lee,  Mill,
                              Bomberger,
                              1976
95% confidence
    limit
    ±2.2
    ±4.5
    ±6.8
    ±3.5
    ±3. 2
    ±2.0
    ±1.3
                                          Experimental conditions:  methyl parathion  concentrations  at
                                                4 and  8 ug/ml.  Sediment  concentrations were  1000  to  2000
                                                times  as concentrated as  methyl parathion  at 8  yg/ml and
                                                1000 to 3000  times as concentrated  as  MP  at 4  pg/ml.

-------
                                                        TABLE 6:  Continued
       Compound Name
                                                                                                                      Ref
         parathion
CD
                                                                                                x/m = KC1'/nor
                                     Adsorption  equation:
                                        log  x/m = log  K  + 1/n log C
Adsorbent
Soil No.*
10
8
11
13
15
14
El
6.20
6
6
5
3
3
.25
.30
.20
.50
.30
Soil organic
matter, % CEC
0
1
2
5
8
24
.75
.62
.88
.52
.21
.62
18
26
42
19
21
28
.6
.6
.8
.2
.2
.9
Natural
K
7.
12.
38.
125
213
457
67
30
02
.90
.80
.10
Soils
1/n
1.04
1.
1.
1.
1.
1.
05
11
05
03
02
                                          Wahid  and
                                            Se th una than,
                                            1978
                                                                                                     Oxidized Soils
                                                                                                      K       1/n
                                                                                                      3.16
                                                                                                     10.72
Experimental conditions:  1 g soil in 10 ml aqueous parathion solution
Method of analysis:  liquid  scintillation
                                                                          1.33
                                                                          1.33
         amitrole
            3-amino-l,2,4-triazole

            C2H4N4
            pKa =4.14  (3-ATH+=H+ +3-AT)
          Compound properties
            water sol 28 g/100 ml (23°C)
           Adsorbent
           H sat. organic matter
           Al sat. organic matter
                                     Adsorption equation:
                     X = X bC/(l+t>C)
                          m
                                          Nearpass,
                                           1969
63 mM/lOOg
49 mM/lOOg
 b**
0.015
0.010
                                                Experimental conditions:   20:1 water to organic matter
                                                Method of analysis:   liquid scintillation
       *all soils  from  India
      ••calculated from figure  2

-------
                                                  TABLE 6:  Continued
Compound Name                                                                                               Ref.


8-Triazine

  cyanazine                                                                             ^,                  Majka and
                                                            Adsorption equation:  — = KC                     Lavy,
      2-[[4-chloro-6-(ethylamino)-                                                m
      s-triazin-2-yl]amino]-2-                                   Chromatography thin-layer (soil)            1977
      methylpropionitrile

                                     Adsorbents             pH   % o.m.   CEC   K     1/n    Rf
                                     	             —   	   	   	   	    	
                                     Monona silty clay loam 6.5   2.9     21.2  4.6   0.96   0.39
                                     (Typic Hapludoll)

                                     Valentine loamy fine   6.6   1.4     10.1  3.4   0.86   0.74
                                     sand
                                     (Typic Ustipsamment)


                                     Experimental conditions: 1 g soil with cyanazine added in
                                          0.2 ml methanol:  10 ml water.

                                     Method of analysis:   liquid scintillation with Packard 3320
                                          spectrometer.

-------
                                                         TABLE 6:   Continued
00
Compound Name
prometryne
2 , 4-bis (isoprcpylamino) -
6-methy Ithio- 1,3,5-
triazine
Compound properties

m.w.
water
20°
pKa =


241
sol 200 pM/1 at
C
4.05

Adsorbent

Lakeland s
Norfolk Is
Norfolk scl
Cecil si
Cecil c
Okenee si

5.3
6.0
5.4
6.3
5.7
4.65
%O.M

0.22
0.57
0.15
1.77
0.53
5.16
Desorption
CCC 1/0.5

3.0
6.5
28
15
18
19

1.5
2.1
5.7
7.9
3.7
19
Kb = -
1/1
0.86
1.5
3.4
4.0
2.3
12
Ps
w
1/2
0.74
1.2
2.6
3.2
1.7
9.0
1/4
0.67
1.0
2.3
2.8
1.6
7.0
Ref
LaFleur,
1976b
S?/_ , > K (calcf **
(Kcal/fnol) o
-4.1
-4.1
-3.6
-4.1
-3.3
-4.6
1060
990
420
1110
280
2340
                                             Method of analysis:  UV spectrophotometry
           *Cation combining capacity - methylene blue adsorption at pH5.

          **AG   = -RTlnk
              sp         o

         ***KQ = Pa/PwPa is PS adjusted to soil weight

-------
                                                        TABLE  6=   Continued
      Compound Name
                                                                       Ref.
      Urea
       diuron

             3-(3,4-dichlorophenyl)-1,1-
           dimethylurea

           C9H1()C12N20

         Compound properties0

           m.w. 233.10

           m.p. 158-159°C

           water sol  42 ppm  at  25°C
Adsorbents
Monona silty clay loam 6.5    2.9
(Typic Hapludoll)

Valentine loamy fine   6.6    1.4
sand
(Typic Ustipsamment)
                       Adsorption equation:  — = KC

                            Chromatography thin-layer (soil)


                       pH    % p.m.   CEC    K_     1/n    ^f

                                      21.2   14.3   0.77   0.18
                                      10.1
                                              6.5   0.74   0.39
                                                                       Majka and
                                                                        Lavy,


                                                                        1977
03
Experimental conditions:  same as for cyanazine.

Method of analysis:  liquid scintillation with Packard 3320
     spectrometer.
       fluometuron

            1,l-dimethyl-3-(o,a,a-
           trifluoro-m-tolyl)urea


           C10H11F3N2°
         Compound properties0

           m.w. 232.21

           m.p. 163-164°C

           water sol 80 ppm at  25°c
                            Chromatography thin-layer  (soil)
Adsorbent

Bethony silt loam

Hector loam

Eufaula sand
                                           Experimental  conditions:   10  g soil:   10 ml of 0.01 N CaCl
                                                solution containing  1,2,4,  or 8  ppm fluometuron.

                                           Method of  analysis:   liquid scintillation.
% o.m.
4.4
4.8
0.3
CEC
12.4
9.2
0.6
pH
6.3
6.3
6.7
Kf
0.57
0.65
0.98
                                                                       Chang and
                                                                        Stritzke,

                                                                        1977

-------
             TABLE 6:  Continued
Compound Name
tebuthiuron
S- [5- (1, l-dimethyl)ethyl] -1,3,4-
thiadiazol-2-yl-ff,A' ' -dimethylurea
Compound properties





Chromatography
Water solvent

water sol 2500 pg/ml Adsorbent
Bethony
Hector
Euf aula
silt loam
loam
sand

%
4
4
0

o.m.
.4
.8
.3

CEC
12.
9.
0.

4
2
6



Ref .
Chang and
Stritzke,
1977
thin-layer (soil)


E3_
6.3
6.
6.
3
7

Rf
0.
0.
0.

58
66
98
Experimental conditions:  10 gm of soil:  10 ml of 0.01 N
     CaCl., solutions containing 1,2,4, or 8 ppm tebuthiuron.


Method of analysis:  liquid scintillation.

-------
                                                        TABLE 6:  Continued
00
Compound Name
paraoxon

-------
                              NOTES,  TABLE 6


aWeast, R. C., S. M. Selby, J. W. Long, and I. Sunshine, eds.  1974.  CEC
     Handbook of Chemistry and Physics.  54th ed.  Cleveland, Ohio:  Chemical
     Rubber Company Press.

 Hodgman, C. D., R. C. Weast, R. S. Shankland, and S. M. Selby.  1961.
     Handbook of Chemistry and Physios.  43d ed.  Cleveland, Ohio:  Chemical
     Rubber Publishing Co.
o
 Windholz, M., S. Budavari, L. Y. Stroumtsos, and M. N. Fertig.  1976.
     The Merck Index.   9th ed.  Rahway, N. J.:  Merck & Co.

 Protivova, J., and J. Pospisil.  1974.  Antioxidants and stabilizers.  XLVII:
     Behavior of amine antioxidants and antiozonants and model compounds
     in gel permeation chromatography.  J. Chromatogr.  88:99-107.

eShults, w. D., ed.  1976.  Chemical and Biological Examination of Coal-
     derived Materials.  Oak Ridge, Tenn.:  Oak Ridge National Laboratory.
f
 Chiou, C. T., and V. H. Freed.  1977.  Partition coefficient and bioaccumu-
     lation of selected organic chemicals.  Environ. Sci.  Technol.  11:475-78.

^Karickhoff, S. W., D. S. Brown, and T. A. Scott.  1979.  Sorption of hydro-
     phobic pollutants on natural sediments.  Water Res. (in press).
h
 Dorigan, J., B. Fuller, and R. Duffy.  1976.  Chemistry, production and
     toxicity of chemicals A-C.  Appendix I in Preliminary Scoring of
     Selected Organic Air Pollutants.  Report No. EPA-450/3-77-008b.  Re-
     search Triangle Park, N. C. :  Strategies and Air Standards Division,
     Office of Air Quality Planning and Standards, U.S. Environmental
     Protection Agency-
fj
 Fendler, J. H., E. J. Fendler, G. A. Infante, P. Shih, and L, K. Patterson.
     1974.  Adsorption and proton magnetic resonance spectroscopic investi-
     gation of the environment of acetophenone and benzophenone in aqueous
     micellar solutions.  J. Am. Chem. Soc. 97:89-95.

 Dorigan, J., B. Fuller, and R. Duffy.  1976.  Chemistry, production and
     toxicity of chemicals 0-Z.  Appendix IV in Preliminary Scoring of
     Selected Organic Air Pollutants.  Report No. EPA-450/3-77-008b.  Re-
     search Triangle Park, N. C.:  Strategies and Air Standards Division,
     Office of Air Quality Planning and Standards, U.S. Environmental
     Protection Agency.
^
 Hansen, R. S., Y. Fu, and F. E. Bartell.  1949.  Multimolecular adsorption
     from binary liquid solutions.  J. Phys. Colloid Chem. 53:769-85.
                                      87

-------
Hangerbrauck, R.  P., D.  J.  Von Lehmden,  and J.  E.  Meeker.   1964.  Emissions
    of polynuclear hydrocarbons and other pollutants from heat-generation
    and incineration processes.  J.  Ai-P  Pollut.  Control Assoc.  14:267-78.

Mackay, D.,  and W. Y. Shiu.   1977.   Aqueous solubility of polynuclear
    aromatic hydrocarbons.   J.  Chem.  Eng.  Data  22:399-402.
                                    88

-------
                              TABLE  7:  AVERAGE VALUES  OF  ADSORPTION CONSTANTS FOR ORGANIC PESTICIDES
03
Compound Name
S-triazines
Average* Average* Soils
l/n±S% K±S% (No. )
simazine 0.820±3.48 6
6-chloro-ff, ff'-diethyl-l, 3, 5-
triazine-2, 4-diamine
m.w. 201. 66a
propazine 0.95±1.7 2.68±33.0 4
2-chloro-4,6-bis
Average** Average*** Soils
K,±S% K ±S% ,„ .
d oc (No.)
1.93+6.69 135+6.33 174
16.3±30 159±5.66 2

2.3717.06 160111.6 54
26.719.71 152+3.7 17
              ( i sopropy lamino ) - a- tr ia zine
              m.w. 229. 71a
         tHamaker, J. W., and J. M.  Thompson.   1972.   Adsorption.
             In Organic  Chemicals  in the  Soil  Environment,  Vol.  1,
             ed. C. A. I. Goring and J. W.  Hamaker,  pp.  51-143.
             New York:   Marcel Dekker,  Inc.
                C
           *K =
                  1/n
          **K, = ^s
         ***K
 ;   = X/m(pg/g of organic carbon) =    d(pg/g of  soil)
 oc              C                    %  organic carbon


Value given is average of K and ]f  adjusted for  organic  carbon

-------
                                                TABLE  7:  Continued
Compound Name
atrazine
6-chloro-ff-ethyl-ff ' -
Average* Average*
l/n±S% K±S%
0.772±8.65
0.709±10.7
Soils
(No.)
19
6
Average**
K,±S%
a
2.94±10.8
25.5±20.4
Average***
Koc±S%
17246.42
102+5.80
Soils
(No.)
79
24
     (1-methylethyl)-1,3,5-
     triazine-2,4-diamine
     j.w. 215.69'
prometone
    2,4-bis(isopropylamino)-
    6-methoxy-a-triazine


    C10H19N5°

    m.w. 225.30a
                                       0.81+2.1
                                                      3.65+26
                                                                            3.31±16.5
                                                    300+19.5

                                                    73.8±5.1
                                                   49

                                                   15
ametryne
    ff-ethyl-tf' - (1-methylethyl)
    -6- (methylthio) -1,3, 5-triazine-
    2, 4-diamine
                                     6.17+11.1

                                     167.4
                                     380+10.0

                                     802
                             33

                              1
     .w. 227. 33a
prometryne
    2,4-bis(isopropylamino)-6
    (methylthio)-s-triazine
    C10H19N5S
0.855±1.1

1.76
7.83+31

50.3
7.03±8.78

55.8±8.46
513+13.0

311+5.12
53

18
    m.w. 241.36C

-------
                                                        TABLE  7:   Continued
      Compound Name
H
            6-chloro-ff,ff-diethyl-
            S'-(1-methylethyl)-1,3,5-
            triazine-2,4-diamine


            C10H18C1N5

            m.w. 243.74°
        hydroxyatrazine


        G30026

            Norazine
            m.w. 201. 66a
                                               Average*
                                               l/n±S%
               Average*
               K±S%
Soils
(No.)
Average*
K+S%
 d 	

47.7
                                     51.5
0.702
               37.4
Average***    Soils
KQCtS%        (No.)

2571            1
                                                    888


                                                    81.8
      Ureas and Uracils
        Urea
                                               0.717
                                                              5.22
                                                                                                   14.3
          Compound properties

            density 1.32,J8

            m.w. 60.06

            m.p. 132. 7°C

-------
                                                TABLE 7:  Continued
Compound Name
fenuron
N , ff-dimethyl-tf' -phenylurea;
l,l-dimethyl-3-phenylurea
m.w. 164. 21a
methylurea
phenylurea
C H N 0
Average*
l/n±S%
0.953±0. 95
1.01±3.20

0.604±2.38
0.832+4.71
0.744+1.34
0.733±2.90
Average*
K±S%
0.554±20.6
6.22±35.3

1.73±26.3
12.5±48.3
1.80±14.8
21.7±52.9
Soils Average**
(No.) Kd±S%
3 0.781±17.0
3 1.01±3.2

3
3
3
3
Average*** Soils
Koc±S% (No.)
0.554+20.6 13
0.622±35.3 1

70.2±7.59
57.6±8.43
76.7±8.83
98.3±12.9
  Compound properties

    m.w. 136.15

    density 1.302


    m.p. 147°C

    b.p. 238°C



bromacil
0.58, 0.85
               0.08, 1.5
19, 123
    5-bromo-6- methyl- 3- (1-methylpropyl)-
    uracil
  Compound properties

    m.w. 261.11

    m.p. 157.5-160°C

-------
                                                        TABLE 7:  Continued
      Compound Name
U)
        terbacil
Average*
l/n±S%
0.50, 0.96
            5-chloro-3- (1, 1-dimethylethyl) -
            6-methyl-2,4 (lfl,3ff) -
            pyrimidinedione
             .w.  216. 6T2
        monuron
            N ' - (4-chlorophenyl) -N ,N-
            dimethylurea
          Compound properties
            m.w. 198.65
            m.p. 170. 5-171. 5°C
            water sol 230 ppm at 25°C
0.74
0.83
Average*
K±S%
0.15, 1.7
                                                                           Soils
                                                                           (No.)
                                                              5. 98
                                                              23.6
Average*
Kd±S%
                      2.17±18.9
                      33.3±22.3
Average***
K  ±S%
 oc
                                                                                                   37, 140
               83.1±22.9
               163±16.7
Soils
(No.)
 31
  6
        diuron
            3- ( 3 , 4-dichlorophenyl) -
            1 , 1-dimethylurea
0.818±6.45
0.707±5.10
              10      6.29±9.33
               3      196±39.2
               351±8.95
               902±31.9
 79
  4
          Compound properties
            m.w. 233.10
            water sol 42 ppm at 25°c

-------
                                                  TABLE 7:  Continued
Compound Name
  metobromuron

      3-(p-bromophenyl)-1-
      methoxy-1-methylurea


      C9HllBrN2°2

      m.w. 259.lla
                                         Average*

                                         l/n±S%
               Average*

               K±S%
             Soils

             (No.)
                                                                             Average*
                                                                             Kd±S%
Average***    Soils

              (No.).
Koc±S%
                                                                                             60±20
  chlorobromuron
                                                                                             217±20
  monolinuron

      3-(4-chlorophenyl)-1-
      methoxy-1-methylurea


      C9H11C1N2°2

      m.w.  214.650
0.810±0.302

0.832±2.33
9.24±9.75

43.0±48.5
                                                                             9.24±9.75

                                                                             43.0±48.5
195±38.9

198±8.67
neburon                                 0.956+2.51      27.9+53.4

    l-butyl-3-(3,4-dichlorophenyl)-
    1-methylurea


    C12H16C12N2°

    m.w. 275.18

linuron                                0.75, 0.75     45.2, 67.8

    a'- (3,4-dichlorophenyl)-
    ff-methoxy-Af-methylurea
                                                                                             787±6.89
                                                                              18.1±18.7

                                                                              147±77.2
                                                    840±20

                                                    653+13.4
                                                    26

                                                     3
   Compound properties

     m.w. 249.10

     m.p. 93-94°C

     water sol  75  ppm

-------
                                                TABLE 7:  Continued
Compound Name
Halogenated Hydrocarbons
ethylene dibromide
1 , 2-dibromoe thane
C2H4Br2
Average* Average* Soils Average** Average*** Soils
l/n±S% K±S% (No.) Kd±S% Koc±S% (NO-'

0.967, 0.970 0.408, 0.803 2 0.537±24.8 32.4±23.7 3
1.04 2.16 1 2.13±1.41 14.4±19.4 2

    m.w, 187.870
beta-BHC
    1,2,3,4,5,6-hexachlorocyclo-
    hexane
    C6H6C16

    m.w. 290.85C
lindane

    la,2a,36,4a,5a,66-
    hexachlorocyclohexane


    C6H6C16

  Compound properties

    m.w. 290.85

    m.p. 112.5°C

    insol. in water
                                       0.861
                                       0.950
                                                      148
                                                      456
0.841,080      45.7,  7.91     2

0.981          331           1
                                                                                           4254
                                                                                           3573
24.7±27.8      1342±15.3       6

321±6.10       1943+20.4       4

-------
                                                  TABLE 7;  Continued
Compound Name
                                         Ave rage *
                                         l/n±S%
  N-serve
      2-chloro-6- (trichloromethyl)-
      pyridine
Average*
K±S%
                                                                     Soils
                                                                     (No.)
Average*
Kd±S%
                      6.80+30.1
                      44.5
Average*
Koc±S%
                                                                                             271±11.5
                                                                                             238
Soils
(No.)
  9
  1
    Compound properties"
      m.w. 230.93
      m.p. 62.5-62.9°C
      b.p. 136-137. 5°C
  DDT
                                                                              1.3X105t
                                                                              LSTXIO*1
                                                                              1.063X105
                                     1.31X10
                                      3.55X10
                                                                                             2.29X10
Carbamates
  chloropropham                          1.00
      isopropyl-m-chlorocarbanilate      1.00
      m.w.  213.67a

  propham
      isopropyl  carbanilate
                                                        21
                                                        132
                      9.28±11.8
                                                                                             590±8.35
                                     51
                                                                                                            65
      m.w.  179.22°

-------
                                                        TABLE 7:  Continued
ID
Compound Name
Average*
l/n±S%
EPTC
S-ethyl dipropylcarbamothioate
m.w. 189. 32a
cycloate
S-ethyl cyclohexylethyl-
Average* Soils Average**
K±S% (No.) Kd±S%
5.96±24.6
52.6
7.32±25
66.6
Average*** Soils
Koc±S% (NO.)
283±18.9 3
109 1
345±17.4 3
222 1

            carbamothioate
            C11H21NOS
            m.w.  215.36°
        pebulate
            S-propyl butylethylthio-
            carbamate
14.5±20.1

109
719+21.4

363
            m.w.  203.:

-------
                                                       TABLE 7:  Continued
Compound Name
Phosphates
nellite
C H N 0 P
Average* Average* Soils Average**
l/n±S% K±S% (No.) Kd±S%

0.525+72.5
6.30, 6.02
Average***
Koc±S*

30.89±25.9
43.5, 33.2
Soils
(No.)

8
2



           m.w. 200.18
00
crotoxyphos

    (E)-1-phenylethyl-
    3-[(dimethoxyphosphinyl)oxy]•
    2-butenoate
                                                                                   6.09+15
                                                                                                  173+34
           C14H19°6P
           m.w.  314.28'
       ohorate
           0,0-diethyl s-l (ethylthio)
           methyl]  phosphorodithioate
                                              0.97+2.1
                                                             8.76±39
                                                                                                  3199+25
           m.w.  260. 38

-------
                                                  TABLE 7:   Continued
Compound Name
disulfoton
    0,0-diethyl S-[2-
   (ethylthlo)ethyl]
   phosphorodithioate

    C8H19°2PS3
  Compound properties"
    m.w. 274.41
    b.p. 1D8°C
    density 1.144g°
    insol. in water

methyl parathion
    0,0-dimethyl 0-(4-nitrophenyl)
    phosphorothioate

    C8H1()N05PS
  Compound properties
    m.w. 263.23
    m.p. 37-38°C
    density 1.358J;0
    water sol 50 ppm

parathion
    0,0-diethyl 0-(4-nitrophenyl)
    phosphorothioate
Average*
l/n±S%
0.930±2.38
Average*
K±S%
20.1±18.9
Soils
(No.)
 10
Average
Kd±S%
                                                                                           Average***     Soils
                                                                                                          (No.)
                                                                                             Koc±S%
                                                                                              2132±25
                                                                                                             16
                                         1.04
                                                         18.43±20
                                                                                             9799±41
                                          1.03±1.5
                                                         2.19±32
                                                                                             10454±38
      m.w. 291.26

-------
                                                        TABLE  7:  Continued
      Compound Name
                                               Average*       Average*     Soils    Average**      Average***     Soils

                                               l/n+S%         K±S%          (NO.)    Kd±S%          Kocf S%         (No.)
        ethion                                 0.945±2.5      28.5±15.9       4                      15435+39.3

            0, 0, 0',0'-tetraethyl 5,5'-
            methylenebisphosphorodithioate



            C9H22°4P2S4
Compound
                   properties'
           m.w.  384.48

,_,          m.p.  -12  to -13°C
o
o          density 1.220^°

           slightly  sol in water


        carbophenothion                        0.940±3.7      74.5+13        4                      45368±40.6


           5-[ [ ( 4-chlorophenyl ) thio ]met hyl ]
           (7,0-dlethyl
           Dhosohorodithioate

           C11H16C1°2PS3

         Compound  properties^

           m.w.  342.85

           b.p.  82°C

           density 1.27lgs

           insol.  in water

-------
                                                    TABLE 7:  Continued
 Compound Name
 Amino, Nitrophenyl  Sulfones
               NO?
    R2S02—/QV- N(R,)Z
               NO?
Average*
l/n±S%
                                                          Average*
                                                          K±S%
Soils
(No.)
Average*
Kd±S%
Average***    Soils
Koc±S%         (No.)
    nitralin
                                      50,  26
500, 520
                          CH3)
        4-(methylsulfonyl)-2,6-dinitro-
        ll, N-dipropylbenzenamine
       m.w.  345.38
SD11830
                                                                                12.5,  7.25      125,  145
SD12639
                                                                               23,  9.65
                                                    230,  193
SD13207
           C2H5;
                                                                               32,  13.5        320,  269
SD12030
        = C3H7;  R2  =  C2H5)
                                                                               75, 35.1
                                                    750,  702
SD12346
          C3H7;  R2
                                                                               117
                                                                                              1170
SD12400
        = CH3; R2 =
                                                                               22.2
                                                                                              222

-------
                                                        TABLE 7:   Continued
      Compound Name
     Carboxylic Acids
       dicamba
            3,6-dichloro-2-
            methoxybenzoic acid
           C8H6C12°3
           m.w. 221. 04
                                               Average*
                                               l/n±S%
Average*
K±S%
Soils
(No.)
Average*
Kd±S%
                                                                                    0.9
Average*
Koc±S%
Soils
(No.)
O      chloramben NH^  salt
           chloramben:  3-amino-2,5-
           dichlorobenzoic acid
                      0.320±30.4
                      4.1
                        15.4±37
                        17.4
           m.w. 206.03
       chloramben methyl ester
       MCPA
            (4-chloro-2-methylphenoxy)-
           acetic acid
                      3.5±35

                      0.420±37.4
                                     507+24
           m.w. 200.62

-------
                                                        TABLE 7:  Continued
      Compound Name
O
U)
                                               Average*
                                               l/n±S%
                                                      Average*
                                                      K±S%
Soils
(No.)
picloram
    4-amino-3,5,6-trichloro-
    2-pyridinecarboxylic acid

    C6H3°2C13N2
    m.w. 241.46
2,4-D
    (2,4-dichlorophenoxy)-
    acetic acid

    C8H6C12°3
    m.w. 221.04a
2,4,5-T
    (2,4,5-trichlorophenoxy)-
    acetic acid
Average*
Kd±S%
                                                                                    0.453±32.2
Average*
Koc±S%
                                                                                                   12.7±21.7
                                                                                    1.59+54.9
                                                                                    1.05+42.3
Soils
(No.)
 14
            m.w.  255.49'
        dichlofcenil
                                                              167
                                                                                    4.19+11.4
                                                                                                   164±3.57
                                                                                                                  16

-------
                                                  TABLE  7:  Continued
Compound Name
Acids
  linear alkyl

  sulfonates

  pentachlorophenol
      C,.HC1,0
       O   D
                        b
    Compound properties
      m.w. 266.35
      m.p. 190-191°C
      b.p. 309-310°C
      density 1.97852
      water sol. 8 rag/100 ml

  methane arsonate
    Compound properties b
      m.w. 139.96
      m.p. 161°C
      freely sol. in water
                                         Average*
                                         l/n±S%
Average*
K±S%
Soils
(No.)
Average*
Kd±S%
Average***
Koc±s%
         34.2±57.4      1222±10.2

         55.3           170

         8.96±20.38
                      12.4±38.9      770±19.1
Soils
(No.)
                                                          20(K
                                                              Qc)
                                                   10

-------
                                                  TABLE 7:  Continued
Compound Name
Miscellaneous
  silvex
      2 - ( 2 , 4 , 5-tr ichlorophenoxy )
      propionic acid
                                         Average*

                                         l/n±S%
               Average*
               K±S%
0.639, 0.987   42.1, 34.2

1.05           162
             Soils

             (No.)



               2

               1
Average*
Kd±S%
Average1

Koc±S%
               2786, 4682

               440
Soils

(No.)
    Compound properties

      m.w. 269.53

      m.p. 181. 6°C

      0.014% sol. in water at 25°C


  chlorthiamid

      2 , 6-dichlorobenzene
      carbothioamide
0.868±1.28
               4.72±8.13
                                                    107.2±6.42
  chloroneb

      1,4-dichloro-2,5-dimethoxy-
      benzene


      C8H8C12°2
      m.w. 207.06a
                                         1.3
                                                        20
                                                    1159
  paraquat
      1,1'-dimethyl-4,41-
      bipyridinium


      C12H14N2
0.566±19.6

0.360±13.3
353±97

5501+16.6
                                                                                             20152±65
      m.w.  186.26

-------
                               NOTES, TABLE 7
a
 Wiswesser,  W.J.,  ed.  1976.   Pesticide Index.  5th ed.  College Park, Mary-
     land:  The Entomological Society of America.



 Windholz, M.,  S.  Budavari,  L.Y.  Stroumtsos,  and M.N.  Fertig.  1976.  The

     Merck Index.   9th ed.   Rahway,  N.J.:  Merck and Co.
                                    106

-------
TABLE 8:  RELATIONSHIP BETWEEN OCTANOL/WATER PARTITION COEFFICIENT AND R  VALUES OF PESTICIDES
                                        ON A SOIL

Mobility Class

Immobile
Low
Intermediate
Mobile
Very Mobile



0.
0.
0.
0.


0
10
35
65
90

Rf
L.
- 0.09
-0.34
- 0.64
- 0.89
- 1.00
JL.
log P
>3.78
3.78-2.39
2.39-1.36
1.36-0.08
<0.08
Ref
"& 7t '
6
•*• Briggs,
>398 1973
398-74
74-29
29-4.5
<4.5
        * P = Octanol/water partition coefficient
       ** Q = Soil  organic matter/water partition coefficient

-------
                                           TABLE 9:  LEACHING OF PESTICIDES FROM A SOIL
                                  Compound Name
                                                                                                                   Ref .
                            Adsorbent = Hagerstown silty clay loam

                            %O.M = 2.41, %O.C = %O.M/1.724 = 1.40
                                                                                                                   Hamaker,
O
00
Pesticide

chloramben
2,4-D
propham
bromacil
monuron
simazine
propazine
dichlobenil
atrazine
chlorpropham
prometone
ametryne
diuron
prometryne
chloroxuron
paraquat
DDT
Rf (soil TLC)


    0.96
    0.69
    0.51
    0.69
     .48
     .45
     .41
     .22
     .47
     .18
    0.60
    0.44
    0.24
    0.25
    0.09
    0.00
    0.00
Mobility class

      5
      4
      3
      4
      3
      3
      3
      2
      3
      2
      3
      3
      2
      2
      1
      1
      1
 !°£*

     12.
     32
     51
     71
     83
    135
    152
    164
    172
    245
    300
    380
    485
    513
  4,986
 20,000
243,000
        *K   = adsorption coefficient on the basis of organic carbon

-------
                            TABLE 10:  SORPTION DEPENDENCE ON SORBATE PROPERTIES
Compound Name

Compound
pyrene
methoxychlor
naphthalene
2-methylnaphthalene
anthracene
9-methylanthracene
phenanthrene
tetracene
hexachlorobiphenyl
benzene

Water solubility
(mole fraction x
12
6.3
4460
3220
7.57
24.4
130
0.037
0.048
189,000
Compound Properties
-3 *
109 Koc(X1° >
84
80
1.3
8.5
26
65
23
650
1200
0.083
Ref.
, lr)-3. ** Karickhoff, Brown,
ow and Scott,
150 1979
120
2.3
13
35
117
37
800
2200
0.13
 *K   = partition coefficient based on organic carbon



**K   = octanol/water distribution coefficient
   ow

-------
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Parker, V. D.  1976.  Energetics of electrode reactions.  II:  The relation-
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     and solvation energies  of aromatic hydrocarbons.  J. Am. Chem. Soc.
     98:98-103.
                                     155

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Radding, S. B., D. H. Liu, H. L. Johnson, and T. Mill.  1977.  Review of  the
     Environmental Fate of Selected Chemicals.  NTIS no. PB-267-121.
     Washington D.C.:  Office of Toxic Substances, U.S. Environmental
     Protection Agency.

Radding, S. B., T. Mill,  C. W. Gould,  D.  H.  Liu, H. L. Johnson, D. C.
     Boiaberger, and c. v. Fojo.   1976.  The  Environmental Fate of Selected
     Polynuclear Aromatic Hydrocarbons.   NTIS no. PB-250-948.  Washington
     D.C.:  Office of Toxic Substances,  U.S. Environmental Protection Agency.

Rao, P. S., and E. Hayon.  1974.  Redox potentials of free radicals.  II:
     Pyrimidine bases.  J. Am. Chem.  Soc. 96:1295-1300.

Roychowdhury, P., and B. S. Basak.  1975.   The crystal structure of indole.
     Acta Crystallogr. B:1559-63.

Sagardia, F=, J. J. Rigau, A. Martinez-Lahoz, F. Fuentes, C. Lopez, and
     W. Flores.  1975.  Degradation of benzothiophene and related compounds
     by a soil pseudomonas in an oil-aqueous environment.  Appl.  Microbiol.
     29:722-25.

Schulman, S. G.  1973.  Correspondence of fluorescing states of naphthols
     and naphtholate anions and its effect on the calculation of pK  from
     spectral shifts.  Spectrosc. Lett.  6:197-202.

Schwarz, F. P., and S. F. Wasik.  1976.   Fluorescence measurements of benzene,
     naphthalene, anthracene, pyrene,  fluoranthene, and benzo(e)pyrene in
     water.  Anal. Chem.  48:524-28.

Seifert, B.  1977.  Stability of benzo(a)pyrene on silica gel plates for
     high-performance thin-layer chromatography.  J.  Chromatogr.  131:417-21.

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     molecules in clay complexes.  Clays Clay Miner.  26:385-91.

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     Ridge National Laboratory.

Slifkin,  M. A. , and A. O.  Al-Chalabi.   1975.   The absorption spectrum of the
     pyrene excimer in different solvents.  Chem. Phys. Lett. 3:198-200.

Suess,  M. J.  1972.  Aqueous solutions of 3,4-benzpyrene.  Water Res. 6:981-85

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                                     156

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U.S. Environmental Protection Agency.  1976.  Identification of Selected
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     Protection Agency.
                                     157

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                      OCCURRENCE AND DISTRIBUTION OF
                     ENERGY-RELATED ORGANIC COMPOUNDS

Andelman, J. B., and J. E. Snodgrass.  1974.  Incidence and significance of
     polynuclear aromatic hydrocarbons in the water environment.  In CRC
     Critical Reviews in Environmental Control, January 1974, 69-83.

Andelman, J. B., and M. J. Suess.  1970.  Polynuclear aromatic hydrocarbons
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     traffic and cancer incidence.  Environ. Sci.  Technol. 11:1082-84.

Blumer, M., and W. W. Ycungblood.  1975.  Polycyclic aromatic hydrocarbons
     in soils and recent sediments.  Science 188:53-55.

Borneff, J.  1974.  Polycyclic Aromatics in Surface and Ground Water.   NTIS
     No. PB-237-786-T.  Research Triangle Park, N. C.:   U. S. Environmental
     Protection Agency.

Cavagnaro, D. M., ed.  1977.  Poly chlorinated Biphenyls in the Environment:
     A Bibliography with Abstracts.  NTIS No. PS-770-792.  Springfield, Va.:
     National Technical Information Service.

Clemo, G. R.  1973.  Some aromatic basic constituents of coal soot.
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Clugston, D. M., A. E. George, D. S. Montgomery, G. T.  Smiley, and H.
     Sawatzky.  1976.  Sulfur compounds in oils from the western Canada
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     the Mining, Processing and Utilization of Coal:  Literature Survey—
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     Coal Research Bureau, West Virginia University

Dvorak, A. J., C. D. Brown,  E. H. Dettman, R. A. Hinchman, J. D. Jastrow,
     F. C. Kornegay, C. R. LaFrance, B. G. Lewis,  R. T.  Lundy, R. D. Olsen,
     J. I. Parker, E. D. Pentecost, J. L. Saquinsin, and W. S. Vinikour.
     1977.  The Environmental Effects of Using Coal for Generating
     Electricity.   NTIS No.  PB-267-237.  Division of Site Safety and
     Environmental Analysis, Office of Nuclear Reactor Regulation, U.  S.
     Nuclear Regulatory Commission.
                                    158

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Gammage, R. B.  1977.  I: Medical Surveillance.  II: Industrial experiences,
     personnel protection and monitoring.  In Proceedings of the 2d ORNL
     Workshop on Exposure to Polynuclear Aromatic Hydrocarbons in Coal Con-
     version Processes.  NTIS NO. CONF-770361.  Oak Ridge, Tenn.:   Oak Ridge
     National Laboratory.

Hangerbrauck, R. P., D. J. Von Lehmden, and J. E. Meeker.  1964.  Emissions
     of polynuclear hydrocarbons and other pollutants from heat-generation
     and incineration processes.  J. Air Pollut. Control Assoc. 14:267-78.

Harrison, R. M., R. Perry, and R. A. Wellings.  1975.  Polynuclear aromatic
     hydrocarbons in raw, potable and waste waters.  Water Res. 9:331-46.

Hayatsu, R., R. G. Scott, L. P. Moore, and M. H. Studier.  1975.  Aromatic
     units  in coal.  Nature 257:378-80.

Neely, W. B., D. R. Branson, and G. E. Blau.  1974.  Partition coefficient
     to measure bioconcentration potential of organic chemicals in fish.
     Environ. Soi. Technol. 8:1113-15.

Olsen, D.,  and J. L. Haynes.  1969.  Consumer Protection and Environmental
     Health Series:  Air Pollution Aspects of Organic Carcinogens.   NTIS
     No. PB-188-090.  Bethesda, Md.:  Litton Systems, Inc.

Palmer, H.  D., K. T. S. Tzou, and A. Swain.   (undated).  Transport of
     Chlorinated Hydrocarbons in Sediments of the Upper Chesapeake Bay.
     NTIS No. PB-255 688.  Washington, D. C.:  Office of Water Resources
     Research, U. S. Department of the Interior.

Ray, S. S., and F. G. Parker.  1977.  Characterization of Ash from Coal-
     fired Power Plants.  NTIS No. PB-265 374.  Research Triangle  Park,
     N. C.:  Industrial Environmental Research Laboratory, Office  of
     Research and Development, U. S. Environmental Protection Agency.

Schiller, J. E.  1977.  Nitrogen compounds in coal derived liquids.  Anal.
     Chem.  49:2292-94.

Shabad, L. M., Y. L. Cohan, A. P. Ilnitsky, A. Y. Khesina, N. P. Shcherbak,
     and G. A. Smirnov.  1971.  The carcinogenic hydrocarbon benzo(a)pyrene.
     J. Natl. Cancer Inst. 47:1179-91.

Shackelford, W. M., and L. H. Keith.  1976.  Frequency of Organic Compounds
     Identified in Water.  NTIS No. PB-267-470.  Athens, Ga.:  Environ-
     mental Research Laboratory, Office of Research and Development, U. S.
     Environmental Protection Agency.

Spangler, C., and N. de Nevers.  1975.  Benzo(a)pyrene and Trace Metals in
     Charleston, S. C.   NTIS No. PB-243-465.  Research Triangle Park, N. C.:
     Office of Air Quality Planning and Standards, Office of Air and Waste
     Management, U. S. Environmental Protection Agency.
                                    159

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TRW Energy Systems.   1976.   Carcinogens Relating to Coal Conversion Processes,
     NTIS No. FE-2213-1.   Oak Ridge, Tenn.:   U. S.  Energy Research and
     Development Administration Technical Information Center.

Van Meter, W. P., and R.  E.  Erickson.  1975.   Environmental Effects from
     Leaching of Coal Conversion By-Products.   Interim report for the
     period June - September 1975.   NTIS No.  FE-2019-1.   Missoula, Mont.:
     University of Montana.

Van Meter, W. P., and R.  E.  Erickson.  1975.   Environmental Effects from
     Leaching of Coal Conversion By-Products.   Interim report for the
     period October - December 1975.  NTIS  No. FE-2019-2.  Missoula, Mont.:
     University of Montana.

Van Meter, W. P., and R.  E.  Erickson.  1976.   Environmental, Effects from
     Leaching of Coal Conversion By-Products.   Interim report for January -
     March 1976.  NTIS No.  FE-2019-3.  Missoula,  Mont.:   University of
     Montana.

Wedgwood, P., and R. L. Cooper.   1954.   The  detection and determination
     of traces of polynuclear hydrocarbons  in industrial effluents and
     sewage.   Analyst 79:163-69.

Wewerka, E. N., J. M. Williams,  and N.  E. Vanderborgh.   1976.   Contaminants
     in Coals and Coal Residues.  Report No.  LA-UR-76-2197.  Los Alamos,
     N. M.:  Los Alamos Scientific  Laboratory.
                                   160

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APPENDIX:  FORMULAS OF ORGANIC COUMPOUNDS
                 COMPOUNDS OTHER THAN PESTICIDES
Acids,  Aliphatic

   acetic  acid

        CH COOH


   adipic  acid
   butyric acid

        CH3CH2CH2COOH


   caproic acid

        CH CH CH CH CH2COOH


   citraconic

        CH.CCOOH
          3 ii
          HCCOOH


   citric  acid

        CH COOH
        i  ^
     HOCCOOH
        I
        CH2COOH


   dibromosuccinic

        BrCHCOOH
          i
        BrCHCOOH
formic acid

     HCOOH


fumaric acid

     HOOCCH
        HCCOOH


glutaric acid
     HOOCCH CH CH COOH
           £*  J-*  £•
glyceric acid
          OH
          i
     HOCH2CHCOOH


glycolic acid

     HOCH COOH
glyoxylic acid

     HCOCOOH


isobutyric acid

     CH-,
     CH.
        ;CHCOOH
                               161

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isovaleric acid

     CH.,
         :CHCH~COOH
     CH-
itaconic acid

     CH =CCOOH

         CH2COOH
lactic acid

     COOH
     i
     CHOH
     I

     CH0
levulinic acid


     CH COCH CH COOH
       O    £•  Z,
maleic acid

     HCCOOH
      ll
     HCCOOH



malic acid

     HOCHCOOH
       i
       CH COOH



malonic acid

     HOOCCH2COOH



mesaconic acid

     CH.CCOOH
       3 ii
    HOOCCH



methylsuccinic acid


                 0
                 ii
     CH OOCCH CH COCH



monobromosuccinic

     HOOCCH2CHBrCOOH
  oxalic

       HOOCCOOH



  propionic acid

       CH3CH2COOH



  pyruvic acid

       CH3COCOOH



  succinic acid

       HOOCCH2CH2COOH


  tartaric acid

       COOH
       i
       CHOH
       i
       CHOH
       i
       COOH


  valeric acid


       CH3CH2CH2CH2COOH
Acids, Aromatic



  benzoic acid


        COOH
  phenylacetic acid
  phenoxyacetic acid
                              162

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Alcohol
  n-butyl  alcohol
       CH  CH  CH CH OH
         •~J £,   £,  £
Amines and  derivatives
  acetanilide
                                         Benzene
                                         Carbamate derivatives
                                                R-LNHCOOR2
                                         Carbonyl compounds
                                           acetophenone
             NHCOCH,
  aniline
  4-(R2  sulfonyl)-2,6-dinitro-N.N.
     (di-R-j) aniline
           o
                                         N-Heterocyclics
                                           benzo[f]quinoline
                                           9H  carbazole
                                           7-H dibenzocarbazole
  crystal violet
            N(CH3)2C1~
Amino Acid
  tryptophan
            CH2CH(NH2)COOH
                                            pyridine
                                           quinoline
                                163

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S-Heterocyclics
  benzo[b]thiophene
Quinone
  dibenzothiophene
Phenols
  phenol
                                   alizarin
                                 Sulfonate
                                   sodium napthalenesulfonate
Polynuclear aromatics
  ben z[a]anthracene
  benz[a]pyrene
  pyrene
                               164

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                               PESTICIDES
Carbamates
   carbaryl
         O-CO.NH-CH,
     CO
   cycloate
     C,H,-S-CO.N(C1H1)
                                 2,4-D
                                            Cl -    >-0-CH,-CO.OH
                                                a
                                         dicamba
                                               CO.OH
                                                 3-CH,
                                         dichlobenil
   EPTC
CH3CH2
  pebulate
                   CH CH  CH

                   CH2CH2CH3
                   OCH2CH-
                                             CN
                                         MCPA
                                                 O-CH.-CO.OH
                                               CH,
  propham
      o
   NH-CO.O-CH^CH,),
                                 picloram
                                     NH,
                                         ci -^N^\ CO.OH
Carboxylic Acids
  chloramben
              OH
         NH,
                                 2,4,5-T
                                  a-/~Vcwai1-co.oH
                                   cK
                                  165

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Halogenated  Hydrocarbons
  BHC
     a  a
     a  a
  DDT
           c-a,
       \=±3S/
  dieldrin
               a  a
  ethylene dibromide
  heptachlor
         a  a
      a
      a
         a
  lindane
         a
         Cl
  methoxychlor
    CH,C
  mi rex
    ac	c
                                          ac
                                       cic-
                                               ca
                                           -c-
                                           a
                                     n-serve
                                                  a
                                                  a
Organophosphates
  carbophenothion

    (C,H,-O),-PS.S-CH,-S -d  >• Cl

  crotoxyphos
       CH3°\
       CH  0 H i    ll  i
         J  0 CH3 0 C

  disulfoton
       CH3CH20
                                     ethion
            ca,
        CH3CH2Ox
          oCHoO II      HOCH9CH
             ^  S      S     2
                                166

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   fenitrothion
        (CH,-0),-PS.O-/}>-N01
                 \i—/
                   CH,
   methyl  parathion


        (CH,-O)J-PS.O—(7- NO,
                                     S-Triazines

                                       ametryne
                                               C,H,-NH
                                       amitrole
   riellite
   paraoxon
    (QH,-0)]-PO.O
   parathion
    (QH,),-PS.O
   phorate
   CH  CH 0

   CH3CH20
                      NHCH
                       SCH CH
Amino, Nitrophenyl Sulfones

  Nitralin
     NO,

!,-§- /~VN (CH, CH.CH,),
 5W
     NO,
                                       atrazine

                                           Cl Y^S- NH-CHHCH,),


                                           CaH,-NH




                                       cyanazine


                                           C,H,-NH-(f'NVN
                                                       i
                                                      Cl
                                            ipazine
                                                       NH-CH(CH,),
                                            norazine
                                            prometone

                                               (CH^-CH-hfH-
                                                         NH-CH^CHJ,
                                    167

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prometryne

   (CH,),-CH-NH -^ N*»i -S-CH,
           N^N
            NH-CH(CH,),
  propazine
               a
  simazine
           CI
Ureas  & Uracils
  bromacil
                                       fluometuron
                                                     C F,
                                       linuron
                                             ci
                                     methylurea

                                       H    O    CH,
                                         H
                                                   H
                                       metrobromuron
                                           Br-/~VNH-CO.N-0-CH,
                                             ^-=/      CH,
                                       monolinuron
                                                 NH-CO.N-CH,(O-CH,)
  diuron
      a
       a
                                       monuron
                                                 -NH-CO.N^CH,),
fenuron
      CH.

      CH
               H
          3  0
                                     neburon
                                            a
                                                ,-a
                                              •JH-CO.N(C.H,)-CH,
                                   168

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phenylurea
Miscellaneous
        H    O   H



                \
                 H
                                     chloroneb


                                            a
        fSpO-CH,

       .O-IS^J

         a
tebuthiuron
              >-N-CO-NH

         CH3  5 CH3  CH3
  chlorthiamid



          CS.NH,
terbacil
             •N-0
  paraquat
                                                             2CH.-SO,
urea
        H    O    H

         \   I  /
          N—C—N-
                                     silvex
            a



       a"\/~°"CH(CH)
i>CO.OH
                                           a
                                 169

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                                   TECHNICAL REPORT DATA
                            (Please read Instructions on the reverse before completing)
1  REPORT NO.
  EPA-600/3-7 9-086
                                                            3. RECIPIENT'S ACCESSIOI^NO.
4. TITLE AND SUBTITLE
 Adsorption of Energy-Related  Organic Pollutants:  A
 Literature Review
             5. REPORT DATE
              August 1979 issuing date
             6. PERFORMING ORGANIZATION CODE
7. AUTHOR(S)
 K.A. Reinbold,  J.J. Hassett,  J.C.  Means, and
 W.L. Banwart
                                                            8. PERFORMING ORGANIZATION REPORT NO.
9. PERFORMING ORGANIZATION NAME AND ADDRESS
 Institute for Environmental  Studies
 University  of Illinois at Urbana-Champaign
 Urbana,  Illinois  61801
             10. PROGRAM ELEMENT NO.
                1BB770
             11. CONTRACT/GRANT NO.

               68-03-2555
12. SPONSORING AGENCY NAME AND ADDRESS
 Environmental Research Laboratory—Athens, Ga,
 Office of  Research and Development
 U.S. Environmental Protection Agency
 Athens, Georgia  30605
             13 TYPE OF REPORT AND PERIOD COVERED
              Final, 7/77 to  4/78
             14. SPONSORING AGENCY CODE

               EPA/600/01
15. SUPPLEMENTARY NOTES
16. ABSTRACT
       This  report is a literature  review on sorption  properties of sediments and
 energy-related organic pollutants.   Adsorption of organic compounds in  general is
 discussed,  and analytical methodology in soil thin-layer chromatography and chemical
 analysis as applicable to measurement of sorption properties is summarized.  The
 literature  on  the adsorption of  energy-related organic  pollutants is reviewed.
 Reported constants for the adsorption of organic compounds on several adsorbents are
 tabulated,  and factors that influence adsorption are  discussed.
17.
                                KEY WORDS AND DOCUMENT ANALYSIS
                  DESCRIPTORS
                                              b.IDENTIFIERS/OPEN ENDED TERMS  C. COSATI Field/Group
    Adsorption
    Chemical analysis
    Coal
    Coal gasification
    Energy
    Organic compounds
    Sediments
                             68C
                             68D
                             99A
                             99D
13. DISTRIBUTION STATEMENT
 RELEASE TO PUBLIC
19. SECURITY CLASS (This Report)
    UNCLASSIFIED
21. NO. OF PAGES
    178
                                               20. SECURITY CLASS (This page)
                                                   UNCLASSIFIED
                                                                          22. PRICE
EPA Form 2220-1 (9-73)
                                             170
                                                                    •i U S. GOVERNMENT PRINTING OFFICE 1979 -657-060/5411

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