United States
                             Environmental Protection
                             Agency
   Hazardous Waste Engineering
   Research Laboratory
   Cincinnati, OH 45268
                             Research and Development    EPA/600/M-87/002    June 1987

                             ENVIRONMENTAL

                             RESEARCH    BRIEF
                      Evaluation of Innovative Technology for the
                  Treatment of Hazardous Aqueous Waste Streams
                                           S. Garry Howell
Introduction

Dilute aqueous wastes have been a treatment problem for
many years.  Even when the waste materials were readily
treatable,  the large  volumes of water  which had  to be
passed through a treatment system  slowed the process,
and required inordinately high capital investments. As  a
result, many such dilute wastes were dumped into streams,
or onto the ground  where they  eventually entered
groundwater supplies. These factors, and an anticipation of
the ban on landfilling of aqueous wastes prompted EPA to
initiate research;programs to concentrate, treat, or recover
organic or heavy metal pollutants from aqueous streams.

This  report summarizes the results of four of the the most
recent projects  initiated by  EPA in  the aqueous  waste
treatment area. We recognize that there is no one solution
applicable to the whole gamut of aqueous waste streams,
and that several approaches must be tried; consequently,
four projects were initiated:
• Concentration of wastes  by  absorbing the  water and
  excluding the solute using reversible gels;

• Concentration  by  reverse osmosis,  using newly
  developed composite membranes;

• Adsorption on "pristine lignin"; i.e., lignin derived from
  steam exploded wood, as opposed to  lignin produced by
  sulfate or sulfite pulping;

• Extraction of pollutants with supercritical carbon dioxide.

Purpose and Objectives
The  purpose of the study was to find economical and
effective ways to concentrate aqueous waste streams or to
remove pollutants from them,  yielding a relatively  pure
water, and a concentrated waste which could be disposed
of in an accepted manner.
The objectives were to determine which types of wastes
(inorganic, nonpolar or polar organic) could be treated by
one or more of  the four processes  chosen, obtain
throughput rates, compare  the  processes  to  existing
technologies,  and  finally, estimate capital and operating
costs if enough data were available.

Technologies Evaluated
Four technologies  were evaluated,  three  aimed  at
concentrating  or extracting the wastes, the fourth was a
novel adsorbent.

Reversible Gel Absorption
The feasibility of  using crosslinked polymer gels  in a
reversible process for extracting pure water from  aqueous
systems was investigated by Drs. Maier and Cussler of the
University of Minnesota (1). Two types of gels were studied,
pH sensitive and temperature sensitive, (so called  because
the reversibility of water absorption could be  caused by
raising pH in the former, or temperature in the latter).

Objectives
The general  objectives  of this  investigation  were  to
determine if either of those two types of gels, as described
below, could be adapted to preferentially absorb water from
a solution containing hazardous wastes, and if so, whether
this technology could be applied  to detoxify "real world"
hazardous waste streams.

Test Results

pH Sensitive Gels
The pH  sensitive gels  were made by copolymerizing
acrylamide monomer and N.N'-methylenebisacrylamide

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crosslinker in water, after which they were treated with 0.5
M sodium carbonate at 60°C for 24 hours to hydrolyze the
amide groups.  By varying the ratio  of acrylamide and
crosslinker. the swelling capacity of the  gel  may be
controlled;  the swelling  or water absorptive capacity is a
function of ionizable group concentration and constriction of
elasticity by crosslinks.
When water of pH 6 or above containing a dissolved solute
is in contact with a gel of this type, the gel will swell to 10
to 120 times its starting volume, depending on the percent
crosslinker, as  indicated in  Figure  1. The absorption of
water concentrates the solution, which may be drained off if
a batch process is used; in a packed  column, a continous
flow of concentrated solution would be produced. After the
gel has reached its maximum capacity, the water is simply
eluted by  acidifying  a  rinse  stream,  as indicated ih the
lower pH range of Figure 1. Concentration  of a number of
aqueous solutions or emulsions is illustrated in Table 1.
Note that all the solutes in Table 1 are  neutral or negatively
charged at the pH of  separation, and  that while larger
molecules  are  excluded, smaller ones are not excluded,
and pass into the interior of the gel particles.

Table  2 lists several  ionized, negatively charged solutes
along  with their molecular weight and potential charges.
Solutes are more efficiently concentrated if they are highly
dilute,  multiple charged, and have no  salt  present.
                                   Predictions based on  Donnan  equilibrium  theory confirm
                                   these observations fairly closely, as noted in the table.

                                   Temperature Sensitive Gels
                                   Earlier  work had  indicated  that modified  polyacrylamide
                                   gels exhibited  abrupt  changes in  volume  in response to
                                   small changes in  temperature. Utilizing this  phenomenon
                                   would allow concentration  of  wastes  with  much  lower
                                   energy  expenditure  than  conventional evaporation
                                   processes.
                                   Two types of these  gels  were  evaluated; one was a
                                   terpolymer of diethyl acrylamide and sodium methacrylate,
                                   with N.N'-methylenebisacrylamide  (MBA) as crosslinker;
                                   the second, a copolymer of N-isopropyl  acrylamide  with
                                   MBA crosslinker. The variation of  gel  volume  with
                                   temperature shown  in  Figure  2  indicates  that  the
                                   polyisopropyl acrylamide  will  lose its imbibed  water  at a
                                   lower temperature, but will hold about 25%  as much as the
                                   other copolymer.
                                   The temperature sensitive gels are not sensitive to pH. As
                                   illustrated  in Table 3, the pH sensitive gel decreases to  0.04
                                   of  its  starting  volume  as acid  is  added,  while   the
                                   temperature sensitive gel  is relatively unaffected. Low salt
                                   concentrations do not cause collapse of  the temperature
                                   sensitive gels; however, high concentrations will collapse
                                   the particles as shown  in Table 4.
 Figure 1.    Gel volume as a function of solution pH. (Source: Reference 1)

       140
       120   -
       100
  Relative
  Volume

        80
        60
         20
 •  2.0%
 O  3.5%
 •  5%
 D  70%
 A.  75%
 A  20%

Percent
Crosslinker
                                                                                    4ğ
                                              O
                                                       D  D
                                          DEO

                                           A
                     *  *
       ;•"#Ğ',
 D

A
                                               All
                                                      6

                                                     pH
                                                                                      10
                                                                                              11

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Table 1.
Concentration of Aqueous Solutions Using Hydrolyzed Polyacrlamide Gels (Source: Reference 1)
Solute
Polystyrene Latex
Polystyrene Latex
Silica
Bovine Serum Albumin
Hemoglobin
Polyethylene Glycol
Sucrose
Urea
Mol. Wt.
Daltons
-
--
-
66,000
64,500
3,000 - 3,700
342
60
Solute Size,
mm
990a
, 34.6a
5a
7.2b
6.2b
3.8°
0.84b
0.53b
Feed Cone.,
Wt.%
0.21
0.91
1.82
0.08
0.73
0.56
1.00
3.00
Raffinate Cone.,
wt.%
0.35
1.40
3.03
0.18
1.26
1.09
1.09
3.00
Percent
Efficiency
85
82
80
93
91
6
6
0
a Measured by electron microscopy.
b Estimated from the diffusion coefficient in water using the Stokes-Einstein equation.
 cReported by the manufacturer from light scattering measurements.
Table 2.     Separation of Charged Solutes with Hydrolyzed Polyacrlamide Gels3 (Source: Reference 1).
Monovalent Test
Solution
10-4 M NaCI
10-4 M Methyl Orange
10-4 M Brornocresol Green
2xlO-4 M Sodium salt of
pentachlorophenolb
10-4 M Methyl Orange
0.1 M NaCI
10-4 M Methyl Orange
Additional
NaCI
_
-
-
3 x 10-3 M
0.1 M
-
0.9 M
n
(expt)
97%
97%
94%
65%
55%
55%
14%
1
(Donnan)
>99%
>99%
>99%
69%
49%
50%
18%
Polyvalent Test
Solution

10-4 M Congo Red
1 0-4 M Trypan Blue
10-4 M Trypan Blue
10-4 M Trypan Blue
10-4 M Congo Red
10-4 M Trypan Blue
1 0-4 M Trypan Blue
10-4 M Trypan Blue
Additional
NaCI
--
--
0.05 M
0.1 M
0.1 M
0.1 M
0.2 M
0.3 M
0.9 M
Jl
(expt)

97%
96%
83&
73%
71%
69%
52%
34%
n
(Donnan)

>99%
>99%
>99%
97%
79%
92%
89%
36%
a Molecular weights and potential charges of the less familiar test solutes are as follows: methyl orange (327.-1); bromocresol green (720.-1);
  pentachlorophenol anion (265.-1); congo  red (697,-2); trypan blue (961,-4).
bThis experiment used a partially hydrolyzed polyacrylamide polymer synthesized with 5% crosslinks. The added electrolyte here is NaOH. All
  other experiments used the hydrolyzed P-6 gel.
 Conclusions and Recommendations
 A serious  but. not insurmountable deficiency of  both
 temperature arid pH sensitive  gels is  their inability to
 exclude smaller molecules such as urea  or methanol while
 imbibing water from a solution. The selectivity of removal
 might be enhanced if a  semipermeable  membrane similar
 to those used  for reverse osmosis  were grafted onto the
 exterior  of  the particles.  This  membrane  could  be
 composed of the same monomers as the interior, but with a
 higher ratio of crosslinker in the skin. The tighter molecular
 structure  would allow only smaller molecules or ions to
 enter into the body of the gel. Another possible approach
 would be to add formaldehyde to the particles suspended in
 water, which would bridge amide groups on the particle's
 surface.
 This  is  an area recommended for development. Such
 development would greatly broaden  the applicability of this
 technology to concentrate dilute solutions of heavy metal
 wastes,  and to organic separations  perhaps;  e.g., the
 separation  of ethanol and  water,  with  large savings in
 energy expenditure.
                                               Low  Pressure  Composite  Reverse   Osmosis
                                               Membranes

                                               Concentration of dilute hazardous organic pollutants  has
                                               been effectively accomplished by  Dr. D. Bhattacharyya of
                                               the  University  of  Kentucky  (2), using  FT-30 reverse
                                               osmosis (RO)  membranes developed by Film  Tech  Inc.
                                               Bhattacharyya's work confirms results reported  by  Lynch,
                                               et al in a I984 EPA report, but carries the study somewhat
                                               further. Reverse osmosis processes use pressure to  force a
                                               fluid through  a membrane  in  the opposite direction of
                                               normal osmotic flow  (solutions normally tend  to become
                                               dilute, a state that is the lowest energy state). RO has been
                                               used for several years to desalinate water, but  was limited
                                               in  application by  the narrow  pH and  temperature
                                               requirements of the cellulose acetate membranes available.
                                               The development of new membrane  materials  has  greatly
                                               broadened the applications  of RO. Composites of  two or
                                               more polymers combine mechanical strength, the ability to
                                               operate  over  a wider pH and temperature range, higher
                                               water flux, and greater rejection for most solutes. Using RO
                                               to  concentrate dilute  organic  aqueous wastes  greatly

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Figure 2.    Gel Swelling  vs. Temperature.  Swelling is reported as a volume  relative to that at high temperature.  The
            polyisopropylacrylamide  shown  on the left has  a sharp change of swelling  at  33°C.  The  copolymer of
            diethylacrylamide and  sodium methacrylate shown  at the right shows a  slower change, fastest around 55°C.
            However, the volume change of the more highly swollen copolymer is larger. (Source: Reference 1)
             12
                                       10
Temperature, °C

     30
                                                                     50
                                                                                    70
             10
    Relative
    Volume
                     Diethyl
                     Acrylamide/sodium
                     Methacyclate
                                 Polyisopropyl-
                                 Acrylamide
                                                                                               40
                                                                                               30
Relative
Volume
                                                                                               20
                24
                               28
                                              32  :            36
                                                 Temperature, °C
                                                                             40
                                                                                             44
improves  incineration  or other  treatments.  Typical
applications of RO in this area would be in concentration of
leachate from landfills and  contaminated groundwater,  or
aqueous wastes from chemical processing.

Objectives
The objective of this investigation  was  to determine the
applicability  of thin film composite membranes  to
concentrate the following types of organic compounds:
• Slightly   soluble organics  such  as  naphthalene,
  anthracene, phenanthrene, and trichlorobenzene; these
            organics were studied both as individual compounds and
            as mixtures.
           • lonizable organics, including  phenol, chlorophenols, and
            nitrophenols. These were studied as mixtures in order to
            determine  if membrane  performance  was affected by
            solute-solvent interactions.

           Broader objectives were  to  find  the  effect  of feed
           concentration, pH, system pressure, and recovery on solute
           rejection and water flux. The effects of these factors on
           membrane stability were also studied.

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Table 3.     Polyisopropylacrylamide Swelling vs. Added Acid
            and Salta (Source: Referencel)
Added Solution
0 mM HCI/g gel
0.04
0.11
0.14 ;
0.19
0.23
0.32
excess 0.05 M NaCI
0.10
1.00
excess 0,05 M CaCI?
Relativeb
Volume
1.00
1.00
0.96
0.93
0.89
0.93
0.92
1.00
0.96
0.22
0.98
Volume of pHb.c
Sensitive Gel
1.00
1.00
0.15
0.11
0.07
0.05
0.04
1.00
0.93
0.80

a All experiments are at 25 °C. The isopropylacrylamide gel was made
 with 1 % crosslinking.
b The relative volume is that in solution divided by that in water.
c The pH sensitive gel was a partially hydrolyzed polyacrylamide with
 5% crosslinking. Similar gels have been reported elsewhere.
Results and Discussion

The apparatus used in the study is shown in Figure 3. The
FT-30 membranes are made  up of three  layers:  a  0.05-
0.25 Jim  layer of aromatic polyamide, 50 u,m of porous
polysulfone. and a 125 um polyester  backing. Figure 4
illustrates the assembly into a batch test cell, using nitrogen
pressure  to drive  the  liquid through  the  membrane.
Separation of selected classes of priority  pollutants were
studied at 0.52-2.068  MPa (75-300  psig).  The batch cell
experiments focused on the individual species and mixtures
of several slightly soluble  PAH  compounds (naphthalene,
anthracene, phenanthrene) chlorophenols, nitrophenols,
phthalates, and chlorobenzene. A wide range  of pH values
were run on the chlorophenols and nitrophenols to establish
the rejection behavior of nonionized and ionized species.
Table 5  summarizes  the results  obtained  with  PAH
compounds. Note that permeate  fluxes were nearly  all in
the same range, and did not vary greatly from the permeate
flux of distilled water.

The rejection of chlorophenols is greatly affected by pH, as
shown in  Figure 4. This effect is  thought to be due to the
exertion  of a repulsive  electrostatic force between  the
membrane and the chlorophenols. Figure 4 also shows the
effect of additional chlorine atoms on the molecules, as the
rejection increases with increasing chlorine content.

Mass  balance  calculations were made  to determine  the
adsorption of chlorophenol solutes on the membrane. The
calculated concentrations at low pH (5.5) differ significantly
from  actual  concentrations  determined  by  TOG
determinations, indicating adsorption on  the membrane; if
pH is raised to  10.8,  adsorption is cut in half.  This
adsorption was further confirmed by running unstirred vs.
stirred samples. Permeate flux  dropped over 63% for
2,4,6-TCP  as  a  result  of a  phenomenon  called
concentration polarization.

Three chlorobenzene homologs were the last compounds
studied.  These  were  monochlorobenzene,   1,4-
dichlorobenzene, and  1,2,4-trichlorobenzene,  all  run  under
unstirred  conditions. As  might be expected, adsorption on
the membrane was  even worse than  with the nonionized
(low pH) chlorophenols  when  unstirred, with the dichloro
and trichloro compounds adsorbing more severely than the
monochlorobenzene. Rgure 5 compares   unstirred and
stirred monochlorobenzene. When stirred,  the permeate
flux remained high, decreasing only by about 2% during the
run, compared to the decrease in the unstirred flux.

Conclusions
Low pressure composite  membranes  offer an  efficient
method of concentrating certain dilute organic wastes. High
solute separations are achieved at  relatively low pressures
of 1-2 MPa (145-290  psi) over the broad  pH  range of 2-
12. The aromatic polyamide membrane tested  was Film
Tech's  FT-30 which showed excellent  stability over long
operating periods with respect to water flux and  permeate
quality.  Rejection  of ionizable  compounds  such  as
chlorophenols was 99 + % at pH  11, but only 77-89% at
pH 4.6; nitrophenols were slightly  less affected by low pH.
While some compounds, notably chlorobenzenes, adsorbed
on the membrane, permeate rejection actually increased at
the expense of a drop in permeate flux.

Extraction with Critical or Near Critical Fluids

While  many extractions  of organic  materials  are
accomplished with common solvents such  as hexane or
ethanol, a growing body of knowledge has developed  on
the use of  near critical  or supercritical  fluids (SCF)  as
extractants. Perhaps the best known  application of SCF is
the use of  SC carbon dioxide  to  decaffeinate  coffee,
replacing the trichloroethylene used previously.

When a liquid is heated in a closed pressure vessel with a
vapor space above it,  it will boil, but there will be a clearly
defined interface  between  the two phases. If heating is
continued, the  pressure  will rise, and  eventually  a
temperature will be reached where the interface disappears;
this is the critical point, above which a single phase having
unique properties exists. Table 6 lists the critical properties
for a number of compounds,  many of which have been
evaluated as solvents.
Using SCF as extraction solvents permits tailoring  the
solvent  properties by  varying  the  pressure  and/or
temperature above the critical point; this simple procedure
plus the wide choice of fluids available, gives considerable
control  over  an extraction process. Many variations of
solvent characteristics are available. As indicated in Table
6, a  nonpolar solvent such as ethylene with low critical
pressures and temperatures may be selected for a specific
task: an extremely polar solvent such as water may be even
more useful. An extreme example of  the  ability to vary
solvency is evidenced in the case of water, which has a
dielectric constant of 80 at room temperature. As  the
temperature is raised toward its critical  point, the dielectric
constant decreases to about 2, which is  very near the value
of nonpolar compounds such as hexane. Above the critical
point,  salts which were soluble  at lower temperatures
precipitate. Conversely, carbon dioxide  (dielectric constant
1.0 at 100 °C and 0.1 MPa) rises to about 1.6 at 5.07 MPa.
Although this is below  the critical pressure of  7.5 MPa,
carbon  dioxide has been used as  an extraction solvent in
this pressure region.

The projects summarized here are an extension of work
done on the regeneration of activated carbon by  extracting
                                                        5

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Tablo 4. Selectivity of Extractions Using Temperature Sensitive Gels (Source: Reference 1)
i
Polyisoproply- Copolymer of Diethylacrylamide
Solute Mol. WL acrylamide and Sodium Methacrylate

Urea
Sodium Pentachtorophenolate
Vitamin B12
Ovalbumin
Potyetheytene Oxide
Galatin
Blue Doxtran
Polystyrene Latex
Polyethylene Gtycol


267
1,355
45,000
600,000

2,000,000
400
3,400
8,000
18,500
19
2
18
32
97
96
98
9?'
950
10
30
56
80
43
3
51
15
84
89
97
99
96b
5
19
25
61
Copolymer of Diethylacrylamide
and Sodium Methacrylate
2a
2
-
7

92
96
96
96°
11
16
48 ,
a Percent of crosslinkage used in preparation.
b This latex has a diameter of 0.06 um.
0 This latex has a diameter of 1.2 jim.
Figure 3.     Batch membrane unit. (Source: Reference 2)

           Feed Solution Inlet

            Permeate
                                                                         0
                                                               Cell Volume:1900 cm3
                                                               Adjustable Shaft
                                                              , Magnetic Stirrer
                                                               (stirring speed: 600 RPM)
                                                                                                           N2

                                                                                                           Tank
                                                             Membrane Area =9.6 cm2

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Figure 4.    Effect of pH on rejections of chlorophenols at 2.068 mPa. (Source: Reference 2)
     100
      90
      80

 Solute
  Rejection
  (%)

      70
      60
      50
                                   AP = 2.068 MPa
                                   Feed: 22 mgll of each solute

                                 A Phenol
                                 Q 2-Chlorophenol
                                 O 2,4-Dichlophenol
                                 • 2,4,6-Trichlor.ophenol
          5.5
                                 6.5
       7.5
pH of Permeate Water
                                                                                8.5
                                                                                                        9.5
Table 5.     Summary of Batch Experimental Results with PAH Compounds.3 (Source: Reference 2)

 Feed                         	Feed pH    Permeate Flux, cm3/cm2 s    Recovery, percent
                                                Rejection, percent
Naphthalene (21 .4)
Naphthalene (2.22)
Antrhacene (0.12)
Phenanthrene (0.574)
Mixture of naphthalene (7.08)
anthracene (0.000999)
phenathrene (0.547)
Distilled water (averaged over 25 days)
6.5
5.5
6.3
6.2
5.5
7
9.45 x 10-4
8.63 x 10'4
9.08 x 10"4
8.92 x 10-"
10.25 x 10'4
11.00X10'4
79.3
82.9
84.2
83.5
82.8

98.01
97.99
> 99.10
> 99.96
88.37
94.14
99.24

a Ap = 1.72 MPa, stirred conditions.
with supercritical carbon dioxide reported by Di Filippi et al.
in 1980 (3). This summary covers  basic  work done at
Louisana State University (4) and the University of  Illinois
(5), and applied studies  on the  extraction  of steel  mill
sludges, pesticide wastes, and toxic water soluble organics
done by Critical Fluid Systems, Inc. (6).


Objectives

The objective of this investigation was to determine whether
critical  or  near critical carbon  dioxide could  be used to
extract  and/or  recover  toxic  organic compounds from
aqueous waste streams. A further objective, based on these
results, was to estimate the capital and operating costs of
an extraction system, and furnish a conceptual design.
          Results and Discussion
          Carbon dioxide is a  convenient  solvent; it is cheap,
          nontoxic, and has a relatively low critical point. On the other
          hand, when a more polar  compound  must be  extracted,
          carbon dioxide may not be very effective. Figure 6 shows
          the results of extraction of a  soil  which had a starting
          concentration of 1000 ug DDT/g soil. Extraction  was done at
          40°C and  10  MPa. Carbon  dioxide  alone  extracts  only
          about half of the DDT, and was only slightly improved by
          adding toluene,  a  nonpolar compound,  as a cosolvent.
          When  5  wt% methanol was  added, the  residual  was
          decreased to about 5% of its starting concentration. While
          this experiment was run on undried  soil, to which the  DDT
          might be quite strongly bound, cosolvents might be a better
          choice for extracting certain aqueous wastes.

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Figure 5.    Instantaneous permeate flux as a function of time for stirred and unstirred  experimental conditions. (Source:
            Reference 4)
   Instantaneous
   Permeate
   Flux (x 10-4)
                 14
                 12
10
                                                n .
                                  Stirred Conditions
                                  Unstirred Conditions
                                 AP = 2.068 mPa
                                 Feed = Chlorobenzene Mixture
                                       100
                                        200

                                  \   Time (Minutes)
                                                                            300
                                                                                               400
Table 6.     Critical  Properties for Selected Fluids (Source:
            Reference 3)                           i

                     Critical         Critical      Critical
                Temperature (To),    Pressure   Density (Pc),
 Fluid                  °C         (Pc), mPa	g/cm3
Penlane
Butane
Sotvont-12
Propane
Ethane
Ethyleno
Carbon Dioxide
Sulfur Dioxide
Ammonia
Water
296.7
152.0
112.0
96.9
32.3
9.9
31.1
157.6
132.4
374.3
3.4
3.8
4.1
4.3
4.9
5.2
7.5
8.0
11
22
0.232
0.228
0.558
0.220
0.203
Q.22J
0.468
0.525
0.235
0.326
Dry mill scale had previously been deoiled with SC carbon
dioxide (4). Since a large portion of mill scale is disposed of
in lagoons, an attempt was made to extract sludge from the
lagoons, recovering iron and a high heating  value oil. j The
sludge is 30 to 70%  solids, and contains  oil,  water,[iron
fines  and toxic and nontoxic  residues. Oil and grease
content varies between 6 and 30% by weight of the solids.
One plant can  produce up to 50,000 tons per year of this
sludge, and the pollution potential and economic losses are
substantial;  an effective  extraction method  would  allow
recycling the iron, and  reuse  of the oil as either fuel  or
lubricant.

Sludge extraction  was attempted with carbon dioxide in a
sieve tray extraction column, the only equipment available.
The dense  sludge was very difficult to handle,  plugging
lines, valves, and  eventually the sieve trays themselves.
Solvent  to  feed  ratios  and dilution were increase^  in
attempts to keep continous flow  and increase oil recovery,
but an oil reduction of 30% was the highest attained. To
handle  the  heavy  abrasive  sludge, a  complete  system
                                          redesign was needed. One design considered was a multi-
                                          stage mixer-settler operating at or above a 4-1 solvent  to
                                          sludge ratio. The economics  of such a system have not
                                          been studied, they may not justify recovery.
                                          Sludge from pesticide manufacturing was tested in a stirred
                                          laboratory reactor and later in the sieve tray pilot plant. The
                                          sludges  contained  water,  xylenes,  carbon  tetrachloride,
                                          solids, fines, salts, and other insolubles. The purpose of this
                                          test was to extract carbon tetrachloride and  the mixed
                                          xylenes from this waste.
                                          Distribution  coefficients determined  in  the  stirred  reactor
                                          indicated  an easy  separation, but  when  tested  in the
                                          continous flow  reactor with a  much  lower shear rate, four
                                          passes were required to attain an overall reduction  of 86%
                                          of the carbon tetrachloride. Results  with xylene extraction
                                          were even more anomalous;  the experimenters postulate
                                          that soaps and dispersants present  in the feed hindered
                                          extraction of the xylene from the aqueous phase.

                                          Extraction of Dissolved Polar Organic Compounds

                                          Carbon  dioxide  extraction  of  aqueous  solutions  of
                                          acrylonitrile and acetonitrile were much  more successful
                                          than any other tests. Much of this success was attributed to
                                          the fact that these solutions were clear with a single phase,
                                          thus the sieve  tray column could function properly; i.e.,  it
                                          could provide better contact between the extractant  and the
                                          aqueous feed.  Using a  solvent to  feed  ratio of  1.5-1
                                          required multiple passes;  i.e., the raffinate  from the first
                                          pass was used as feed for the next. A total  of five passes
                                          were used to get acetonitrile below the minimum detection
                                          limits. Acrylonitrile, as predicted from distribution coefficient
                                          data, was  much easier to extract;  only one pass  was
                                          required to remove it below the detection limit. The success
                                          of  these  runs  resulted  in their use  as a basis for  a
                                          conceptual plant design.
                                          A hypothetical wastewater extraction system was designed
                                          to process a stream  with  properties  and compositions  as
                                          shown in Table 7. The economical number of trays for the
                                          extraction was determined to be 30, using a tray efficiency

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Figure 6.     Extraction results. (Source: Reference 4)
                                                  60 - 1000 itg DDTlg soil
  0.6  r-
                                            O Pure  SC-C02
                                            • SC-CO2 with 5  wt% toluene
                                              SC-CO2 with 5  wt% methanol
  0.4   -


 Relative
 DDT
 Cone.
 (6/60)

  0.2  h-
                                       20
                                                 Time (Minutes)
                                                                        40
                                                                                                         60
of 0.44 and a solvent to feed ratio of 2-1. This system is
designed to reduce  a  waste stream having  1680  ppm
acetonitrile to less than 5 ppm,  a reduction of 99.7%. A
process flow diagram is shown in  Figure 7, where the waste
stream  is  contacted countercurrently  with  an upwardly
flowing  stream of carbon dioxide at 7.6 MPa (1100 psi). The
extract  stream has the recovered organics separated at
high pressure in  a distillation column, thus minimizing the
work  required to recompress the  carbon dioxide, whose
heat of vaporization is  furnished by the adiabatic heat of
compression of the recovered solvent.
Estimated annualized operating costs of a plant processing
20 gpm of an acrylonitrile/acetonitrile feed operating  8000
hours per year are given in Table 8. Processing cost would
be about $0.084/gal. with no credit for recovered product. If
the recovered products were purified, they would be worth
about  $100,000 total,  and  would  lower  the overall
processing cost appreciably.

Conclusions
Supercritical or  near critical extraction  of  organics  from
aqueous wastes  is applicable to certain  waste streams,
particularly  those having very toxic or valuable  solutes.
Aqueous wastes  with suspended solids and sludges  must
be handled  on   a  case-by-case  basis, with very  careful
consideration of the equipment  requirements,  and  an
awareness of construction costs.  As the art and science of
this  process  now  stands,  laboratory determinations of
partition coefficients  and other parameters must be  done
before any larger scale extractions are attempted.

Use of Pristine LJgnin to Treat Hazardous Waste
Conventional wood  pulping processes  are prodigous
chemical by-product producers.  In addition to the  lignin
extracted,  which  is not in its "pristine" form (in the  Kraft
process lignin is converted to thiolignin,  and  in  sulfite
processing, much  is  converted  to lignin sulfonates)
hemicellulose sugars are produced; these are oxidized to
saccharinic acids in the Kraft process. Much of the lignin,
saccharinic acids, and hexoses are presently  burned  as fuel
for other parts of the papermaking operation.  Some sources
have  stated that the fermentable hexoses alone  could
produce two to three times the amount of ethanol presently
produced in the U.S. (7).

Newer pulping  processes beginning to  be adopted  use
solvents such as ethanol to extract lignin from  the wood
chips, or explode chips by saturating them with steam in an
autoclave, then suddenly releasing the pressure. The lignin
thus produced is much nearer to its structure as it existed
in nature, and has been dubbed "pristine" lignin. A study of
the use of this material  to  adsorb  both  organic  and
inorganic compounds from aqueous media, and to compare
its performance to activated carbon, has been performed by
Dr. D. J. O'Neil at Georgia Institute of Technology's Georgia
Tech  Research Institute (8). Since lignin is  much cheaper
than activated carbon ($0.03-0.13/kg vs. $1.00 + ) it could
compete if it were only 1/10 as adsorptive,  and instead of
regenerating the adsorbent, it could, in many instances be
burned, as it has some fuel value.  If the same assumption
of efficacy is  applied  to  ion  exchange resins,  an even
greater cost advantage would be seen if pristine lignin were
used to remove heavy metals. A typical structure of lignin is
shown  in  Figure 8. The rich  organic functionality is
apparent,  with  many carboxylic acid, phenolic, quinone
groups and others available.

Objectives
The principal objective of this study was to demonstrate
that "pristine"  lignin could provide a low cost, yet effective

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Flguro 7.     Flow diagram of proposed extraction process.
                                                           Distillation
                                                           Column
                                                           Flash Drum
                                                                                              Extract
                                                                                           Waste
and flexible material for the treatment of various  aqueous
waste streams. To accomplish this, lignin was evaluated as
a physicochemical adsorbent of heavy metals and organic
compounds.  Other objectives included an  evaluation of
lignin's technical and cost effectiveness in comparison to
current treatment technologies such  as activated carbon
adsorption, as  well as a conceptual design  of a full-scale
treatment plant.

Results and Discussion
Adsorption studies reported here  used lignin derived from
tulip poplar, a  relatively common, fast growing tree of the
Southeastern U.S. Two types of lignin were extracted, the
first, a light brown  powder,  was obtained from  steam
exploded  wood  chips  using 95% ethanol. Addition of
benzene  in an attempt  to  change the character of the
extract produced a  gummy  precipitate upon drying.  The
fraction of lignin recovered averaged 7.5%, had an average
surface area of 30 square meters per gram, and an average
molecular weight of  1380. The second type  of extract was
made  with  dilute sodium  hydroxide, and  although an
average of 31.9% of the lignin was extracted, the surface
area was only about 0.1-0.3 square meters per gram,  but
the molecular weight was  2300. with a  much broader
distribution. The complex structure  and presence of many
different polar groups  presents  great  difficulties  in
elucidating the structure of lignin for, as was the case here,
the extraction method defines the product.

The adsorptive behavior of ethanol extracted lignin  was
studied  using  water  spiked  with  several  organic
"contaminants" and  results are presented in Table  9.
Although smooth curves of adsorption were obtained, there
does not appear to be any pattern of structure dependency
of the  adsorption  isotherms.  Rough estimates  of  the
capacity of the large particle size (30-40 mesh) lignin used
indicate that a smaller  particle size  adsorbent  should
remove about 5  g/kg of  the seven compound mixture in
Table 9, and about 0.3  g/kg of 2,4-D. Adsorption of  lead
and chromium compounds (the  investigator does  not
specify the species) is shown  in Figure 9. An adsorption
capacity of 1.3 g/kg of these metals is  estimated under the
conditions of this test. Speed of adsorption is much higher
when higher ratios  of  adsorbent to both organic  and
inorganic compounds was used,  suggesting that an
                                                       10

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Table?.    Properties  and  Composition  of  Acetonitrile/
           Acrylonitrile Waste Streams (Source: Reference
           6)

 Feed Rate, gpm                                 20
 Acetonitrile, ppm                               1680
 Acrylonitrile, ppm                              1200
 Dissolved Sulfates, weight %                        2.5
 Water, weight %                                 97.5
 Temperature,  °F                                 80
 Specific Gravity                                  1.0

 Characteristics of Recovered Organics
 Organics: Acetonitrile, Acrylonitrile, weight %          98.5
 Carbon Dioxide, weight %                          0.5
 Water, weight %                                  1.0
 Temperature,  °F                                100

 Characteristics of Wastewater Effluent
 Water, weight %                                 97.4
 Carbon Dioxide, weight %                         < 0.06
 Acrylonitrile, ppm                                < 2
 Acetonitrile, ppm                                 <2
 Sulfates, weight %                                2.5
 Temperature,  °F                                100
Tables.     Annualized  Operating  Costs  of  20-GPM
            Acetonitrile - Acrylonitrile Extraction Plant.
            (Source: Reference 6)
 Utilities
 Electricity (175 kWhr/hr @ $0.04/kW hr)
 Well Water (18 gpm @ $1.50/1,000 ga!)
 Steam (230 Ib/hr @ $10.00/1000 Ib)

 Solvent  Make-Up
 Carbon Dioxide (15 Ib/hr @ $100.00/2000 Ib)

 Labor
 1 Operator @ $13.00/hr

 Annual Processing Cost
  Annual
  Cost

 $56,000
  12,960
  18,400


   6,000


  104,000

$802,360*
 * Depreciation, overhead, and miscellaneous operating supplies of
   $605,000 included.
increase in surface area  would  be of great  benefit. A
comparison of the adsorptive capacity of ethanol vs. alkali
extracted lignin indicates that the latter might be as good or
better in capacity if the difference in particle size is taken
into  account.  The alkali  extracted lignin had much  larger
particles, partially accounting for its lower surface area per
gram. Another factor favoring alkali extracted lignin  is the
higher yields; more adsorbent may be obtained per pound
of wood. Tables 10 and 11 indicate that after an adjustment
for surface  area  is made, alkali lignin would be about as
good on organics, and better as a metal  adsorbent than
ethanol extracted lignin.

A comparison of the adsorption isotherms of alkali extracted
lignin   and  activated carbon,  based  on  Freundlich
parameters indicates that approximately 30 times as much
lignin  as  activated  carbon  is required  to  achieve a
comparable reduction in phenol in  a water  solution. A
comparable figure was obtained for naphthalene. A much
more favorable comparison of lignin vs. activated carbon is
obtained when:Freundlich  parameters for metal adsorption
are calculated (Figure  10). The ratio of lignin to carbon is
only about 4-1;  taking cost into  account,  lignin might be
the preferred adsorbent in this case.
Although data gathered in this report are very preliminary, a
conceptual design of a  one million gallon per day  water
treatment plant is shown in Figure 9. Efficient operation of
an adsorption plant of this type will depend on  developing
methods of controlling particle size and surface  area of the
lignin adsorbents.

Conclusions and Recommendations
Pristine lignin, particularly the alkali extracted variety, shows
some  promise  as a  low cost  adsorbent for aqueous
hazardous wastes.  This  preliminary  study indicates that
further work  must  be done to control  particle size and
expand surface area (expressed in square meters per gram)
before a firm conclusion can be  drawn. Evaluation of this
high surface-controlled  particle  size  material might yield
enough data  to allow the design of a pilot  size  test unit to
indicate the feasibility  and  cost of  a  full-size  water
purification plant based on this technology.

References
1. Maier,  W. J., and  Cussler,  E. L.  Dewatering of  Dilute
   Aqueous  Hazardous  Wastes  Using  Reversible Gel
   Absorption. EPA Contract  68-03-1957.
2. Bhattacharyya, D. et al. Concentration and Purification of
   Dilute Hazardous  Wastes  Using  Low  Pressure
   Composite Membranes. Cooperative  Agreement  CR
   911976.
3. DeFilippi, R. P. et al. Supercritical Fluid  Regeneration of
   Activated  Carbon for  Adsorption  of Pesticides, EPA
   600/2-80-054.
4. Knopf, C.  F. (Louisiana  State  University) Private
   communication.
5. Eckert,  C.  Ai  (University  of  Illinois)  Private
   communication.
6. Rice,  P.  N.  et  al. Supercritical  Extraction of Aqueous
   Hazardous Waste, EPA Contract  68-03-1956.
7. Mayerly,  R.  C.  ef  al. The Forest Refinery.  Chemtech.
   March  1981, page 186.
8. O'Neil, D. J.  et  al. Low Cost, High  Efficiency Pristine
   Lignin  for Hazardous  Waste  Treatment.  Cooperative
   Agreement CR  812223-01-0.
                                                         11

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 Figure 8. Typical tlgnin structure. (Copyright 1967 by John Wiley & Sons, Inc. Reprinted by permission of John Wiley & Sons,
         Inc. From Klrk-Othmer Encylcopedia of Chemical Technology, Anthony Standen, Executive Editor.)
                                                                                                              .0
H(CaH,A).0.
    CH.O
                                                                                               OCHa
                                                          12

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Table 9.
Concentrations of
Reference 8)
                              Model Compounds in the Supernatant After Adsorption on the Pristine Lignin (ppm).  (Source:
Time
Ohr
1 hr
2hr
4 hr
8 hr
1 day
2 days
4 days
4 daysc
Aniline
5.000
4.09
3.20
3.29
3.34
3.75
4.09
4.14
3.97
3.52
3.25
1.56
2.62
2.88
1.47
0.71
: 1.28
Phenol
5.000
2.62
2.56
2.73
2.50
2.56
2.66
2.48
2.22
1.94
2.38
2.26
2.16
1.77
2.16
2.05
2.06
Isophorone
1.560
1.66
1.37
1.29
1.41
1.39
1.49
1.38
1.61
1.31
1.23
1.22
1.06
1.16
1.02
0.68
0.81
Naphthalene
1.300
0.97
0.74
0.61
0.65
0.63
0.65
0.57
0.64
0.56
0.51
0.53
0.41
0.48
0.45
0.21
0.24
Pentachlo-
rophenol
1.540
0.70
0.70
0.54
0.52
0.49
0.49
BDt_a
BDL
BDL
BDL
BDL
BDL
BDL
BDL
BDL
BDL
Bis-(EtHex)
phthalate
1.560
0.33
0.36
0.29
0.23
0.22
0.23
0.14
0.14
0.18
BDL
BDL
BDL
BDL
BDL
BDL
2,4-D
1.250
.08
.27
.21
.28
.05
.28
0.74
1.03
0.67
-b
0.63
0.57
0.65
0.60
0.75
Trichloro
ethylene
2.500
1.97
1.55
1.54
1.52
1.93
1.52
0.36
1.78
1.63
1.73
1.97
1.94
1.45
0.54
1.26
       - Below detection limit.
 bSamples were lost.
 cLignin dose was 0.75 g for organic mixture, 0.5 g for 2,4-D, and metal kinetics study.
Table 10.     Test Results - Second Size Study (Organics). (Source: Reference 8)

           Concentrations of Model Compounds in the Supernatant After Adsorption on the Pristine Lignin (ppm)
                                                Equilibrium Time: 4 days
Liqnin
C0 Nominal
C0 Actual
ETOH Extract
30x40
40x60
60x100
NaOH Extract
60x100
Aniline
4.758
4-447
4.130
3.130
3.222
2.917
2.164
1.577
1.620
1.230
1.420
Phenol
5.337
4.346
4.298
4.346
4.036
4.209
4.357
3.340
3.832
3.987
4.099
Isophorone
2.043
1.985
2.002
1.467
1.500
0.969
1.003
1.434
1.340
1.695
1.587
Naphthalene
2.259
2.113
1.856
0.660
0.453
0.665
0.654
6.428
0.597
1.053
0.857
Pentachlo-
rophenol
2.610
1.833
2.123
0.360
—
__
0.488
0.665
Bis-(EtHex)
phthalate
4.031
2.790
3.500
1.263
1.349
1.514
1.143
0.774
0.854
2.392
2.184
Trichloro-
ethylene
3.336
2.583
2.604
2.058
1.847
1.333
1.398
1.577
1.520
1.348
1.477
 Note: Sample volumes of 100 ml were used (except for trichloro-ethylene: 120 ml).
                                                           13

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Figure 9. Conceptual design of a 1 MGD treatment plant. (Source: Reference 8)
                          Float Oil
                          to Incinerator
Sediment and Waste Adsorbent
        to Incinerator
         Course
         Basket
         Strainer
                                                                   Back
                                                                   Wash Water
                                                                   10 gpm/ft2
                                                                             ireate
                                                                             Effluent
                                                                             Storage
                                                                             Surge
                                                                         Sewer System
                                                                         (POTW) or Receiving
                                                                         Water
                                                           14

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Table 11.     Test Results - Initial and Second Size Studies.
             (Source: Reference 8)

     Adsorption of Lead and Chromium on Lignin, pom (4 days)

                                   Lead
Lignin
C0 Nominal
C0 Actual

Ethanol Extracted
30x40

40x60

60x100

NaOH Extracted
60x100

Lead
10
8
8

7.83
7.3
7.37
7.2
6.4
7.5

5.5
7
(duplicate)
10
11.3
11.02

7.5
8.00
6.5
8.50
6.50
6.45

2.50
2.00
Chromii
10
9.89
9.9

4.19
5.34
4.55
4.56
4.93
4.65

0.86
0.92
Figure 10.    Kinetic study of the adsorption of heavy metals on pristine lignin (Cr and Pb). (Source: Reference 8)

   Cone, (ppm)

   10   ••——Jl                                     Pristine Lignin (30/40 Mesh)
                                                      pH = 4.0
                                                      Temp.  = 19"C
                                                    • - Lead/0.25 g Lignin
                                                    D - Lead/0,50 g Lignin
                                                    • - Chromium/0.25 g Ugnin
                                                    O - ChmmiumlO.50 g Lignin
                                                         Time (Days)
                                                           15

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