GCA-TR-75-32-G (7)
     ASSESSMENT OF CYCLOHEXANONE
 AS A POTENTIAL AIR POLLUTION PROBLEM
                VOLUME VII
               FINAL REPORT
            Contract No. 68-02-1337
              Task Order No. 8
                 Prepared For
        U.S. ENVIRONMENTAL PROTECTION AGENCY
              Research Triangle Park
              North Carolina 27711
                 January 1976
GCA TECHNOLOGY DIVISION «®A
           BEDFORD, MASSACHUSETTS 01730

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                                         CCA-TR-75-32-G(7)
    ASSESSMENT OF CYCL011EXANONE

AS A POTENTIAL AIR POLLUTION PROBLEM

             Volume VII
                 by

         Robert M. Patterson
          Mark I. Bornstein
            Eric Garshick
           GCA CORPORATION
       GCA/TECHNOLOGY DIVISION
       Bedford,  Massachusetts
             January  1976
         Contract No.  68-02-1337
            Task Order No.  8
          EPA Project Officer

             Michael Jones


            EPA Task Officer

             Justice Manning
  U.S.  ENVIRONMENTAL PROTECTION  AGENCY
         Research Triangle Park
          North Carolina 27711

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This report was furnished to the U.S. Environmental Protection Agency by the
GCA Corporation, GCA/Technology Division, Bedford, Massachusetts 01730, in
fulfillment of Contract No. 68-02-1337, Task Order No. 8.   The opinions,
findings, and conclusions expressed are those of the authors and not neces-
sarily those of the U.S. Environmental Protection Agency or of the cooperating
agencies.  Mention of company or product names is not to be considered as an
endorsement by the U.S. Environmental Protection Agency.

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                                ABSTRACT
This report is one of a series which assesses the potential  air  pollution
impacts of 14 industrial chemicals outside the work environment.  Topics
covered in each assessment include physical and chemical properties,
health and welfare effects, ambient concentrations and measurement meth-
ods, emission sources, and emission controls.  The chemicals investigated
in this report series are:
                               Acetylene
                               Methyl Alcohol
                               Ethylene Bichloride
                               Benzene
                               Acetone
                               Acrylonitrile
                               Cyclohexanone
                               Formaldehyde
                               Methyl Methacrylate
                               Ortho-Xylene
                               Maleic Anhydride
                               Dimethyl Terephthalate
                               Adipic Acid
                               Phthalic Anhydride.
Volume I
Volume II
Volume III
Volume IV
Volume V
Volume VI
Volume VII
Volume VIII
Volume IX
Volume X
Volume XI
Volume XII
Volume XIII
Volume XIV
                                  ill

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                               CONTENTS
                                                                  Page
Abstract                                                          m
List of Figures                                                   v
List of Tables                                                    v
Sections
I       Summary and Conclusions                                   1
II      Air Pollution Assessment Report                           3
            Physical and Chemical Properties                      3
            Health and Welfare Effects                            3
            Ambient Concentrations and Measurements               7
            Sources of Cyclohexanone Emissions                    9
            Cyclohexanone Emission Control Methods                11
III     References                                                16
Appendix
A       Cyclohexanone Manufacturers                               18
                               Iv

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                                FIGURE

Ko«>                                                               Page

1    Estimated Installed Cost of Cyclohexanone Storage
     Tanks (Equipment Costs Assumed to be the Same as
     Gasoline Storage Tanks)                                      15


                                TABLES

No»                                                               Page

1    Significant Properties of Cyclohexanone                      4

2    Acute Effect of Cyclohexanone on Animals                     6

3    Cyclohexanone Consumption - 1974                             10

4    Sources and Emission Estimates of Cyclohexanone   1974       10

5    Estimated Installed Costs of Adsorption Systems              12

6    Estimated Annual Operating Costs of Adsorption Systems       12

7    Estimated Installed Costs of Thermal and Catalytic
     Incinerators                                                 14

8    Estimated Annual Operating Costs of Thermal and
     Catalytic Incinerators                                       14

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                               SECTION I
                        SUMMARY AND CONCLUSIONS

Cyclohexanone is a colorless, slightly volatile liquid with an odor
similar to acetone and peppermint.  It is chemically stable and is
manufactured mainly by catalytic dehydration of cyclohexanol.  It is
used extensively in the production of nylon and adipic acid, and it is
also used as a solvent and degreaser.  Cyclohexanone is a strong irritant
and a narcotic agent at high concentrations, although concentrations
producing such effects are unlikely to occur due to the low volatility
of Cyclohexanone.  The occupational standard for an 8-hour time weighted
exposure is 50 ppm.

Simple diffusion modeling estimates place the likely maximum 1-hour
average ambient concentration at 1.3 ppm.  The maximum 24-hour average
ambient concentration might be expected to be about 1 ppm.

Approximately 850 million pounds of Cyclohexanone were produced at
10 plants in 1974, with about 43 percent of this being used to make capro-
lactum for nylon 6, and 52 percent to make adipic acid.  The remaining 5
percent was used as a solvent and as a degreasing agent.  Total production
is expected to increase at 10 percent per year for the next several years.
Emissions result mainly from solvent usage, production losses, and bulk
storage.  About 6 percent of total production is eventually lost to the
atmosphere.

Although emission controls specifically for Cyclohexanone are not
reported, two types of controls are used extensively by the chemical

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industry to control hydrocarbon emissions.  These are vapor recovery
and incineration.  Control by adsorption on activated charcoal is used
when recovery is economically desirable.  The primary advantage of in-
cineration is that low concentrations may be oxidized with only small
supplemental fuel requirements.  Fixed roof storage tanks can be con-
trolled by venting to an adsorber or to an incinerator, or they can be
converted to floating roof design.

Based on the results of the health effects research presented in this
reportj and the ambient concentration estimates, it appears that
cyclohexanone as an air pollutant does not pose a threat to the health
of the general population.  In addition, cyclohexanone does not appear
to pose other environmental insults which would warrant further inves-
tigation or restriction of its use at the present time.

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                               SECTION II
                     AIR POLLUTION ASSESSMENT REPORT

PHYSICAL AND CHEMICAL PROPERTIES

Cyclohexanone is a colorless to pale yellow, slightly volatile liquid
with a ketone-type odor similar to acetone and peppermint.  It is chem-
ically stable and not very flammable except at high temperatures.  The
main method of manufacture is by the catalytic dehydration of cyclohexanol.
Its most important use is as an intermediate in the manufacture of nylon 6,
and it is also used as a metal degreaser, a solvent and a thinner for
lacquers and synthetic resins.  It is found in paint removers, and it is
an excellent solvent for DDT, some organic phosphorous insecticides, and
                        1 2
other similar materials.  '   Significant characteristics of cyclohexanone
are listed in Table 1.

HEALTH AND WELFARE EFFECTS

Effects on Man

Acute Poisoning - Cyclohexanone is a strong irritant and a narcotic
agent.  Humans exposed for 3 to 5 minutes found 50 ppm irritating to the
                       3
eyes, nose, and throat.   Exposure to higher levels and human response
have not been documented in the literature, but animal studies indicate
that human exposure to elevated levels would cause narcosis, dizziness,
unconsciousness, and death due to respiratory failure.  Concentrations
producing such effects are unlikely to be encountered due to cyclo-
hexanone's low volatility, except when handled at high temperatures.

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           Table 1.  SIGNIFICANT PROPERTIES OF CYCLOHEXANONE
Synonyms:  anone, hexanon, hytrol o, ketohexamethylene, nadone, pimellc
           ketone, sextone
Chemical formula
Molecular weight
Boiling point
Melting point
Specific gravity
Vapor density
Vapor pressure
Solubility

Lower explosive limit
Ignition .temperature
Flash point
At 25°C and 760 mm Hg
                        H2C
                 CHr
                                         CH,
                                  C
                                  H,
98.14
155.6°C
-45°C
0.9478 at 20°/4°C
1.01 (air = 1)
5.2 mm Hg at 25°C
2.4 g/100 ml water at 31 C,  soluble in alcohols,
  ketones, esters, halogenated hydrocarbons.
  Partially soluble in benzene. '
1.1% by volume
420°C
43.6 C (closed cup)
                 2
1 ppm =4.01 mg/ra
        =0.25 ppm

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Its vapors have such strong warning properties at low concentrations
that the acute exposure necessary to cause severe poisoning will not be
tolerated voluntarily by humans.  Irritation of the eyes, nose, and throat
due to exposure at low concentrations is only temporary, with recovery
after removal of the vapor.

                                            2
Cyclohexanone has a low acute oral toxicity,  and absorption through
the skin will not be a problem unless there is excessive exposure..  It
is capable of defatting the skin, and exposure to high concentrations
may cause skin irritation.

Chronic Poisoning   Prolonged or repeated exposure will cause dermatitis.
It has been reported that no ill effects, except drowsiness, were observed
                                               2
in workers in daily contact with cyclohexanone.   No fatality or serious
poisoning has been reported in the literature.  Chronic exposure to con-
centrations able to produce delayed narcotic symptoms and death as shown
in animal studies are not likely to be encountered in humans due to human
sensory warning response at low levels.  A concentration of 25 ppm has
been estimated to be the highest concentration tolerable for an 8-hour
                             3
exposure with no ill effects,  but the United States occupational standard
for an 8-hour time weighted exposure average is 50 ppm.

Effects on Animals

Acute Poisoning - Studies done on animals illustrate the acute narcotic
action of cyclohexanone.  Table 2 summarizes available dose-response data
from various inhalation studies. ' '   Symptoms in guinea pigs prior to death
                                              i
were narcosis; lachrymation; excess salivation; depression of body tem-
perature, respiratory rate, and heart rate; and opacity of the cornea.
Recovery was slow, with some guinea pigs dying within 4 days.    A concen-
tration of 2,000 ppm inhaled over 4 hours is the lowest recorded concen-
tration able to cause death in susceptible rats.

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           Table  2.   ACUTE  EFFECT OF CYCLOIIEXANONE  ON ANIMALS
Animal
Rat
Guinea pig
Rat
Rat
Dose ,
ppm
8,000
4,000
4,000
2,000
Time,
hr
4
6
4
4
Response
Anesthesia and death
Narcosis; death to some
within 4 days
Narcosis; all survived
Narcosis; some deaths
Reference
6
1
6
7
Rabbits were killed by the absorption of 10.2 to 23.0 g/kg body weight
                               Q
through clipped uncovered skin.   Symptoms prior to death were marked
hypothermia, convulsions, and narcosis.  Pure cyclohexanone dropped
                                                              9
into the eyes of rabbits caused irritation and corneal injury.   Oral
                                                   Q
administration of 1600 mg/kg body weight to rabbits  resulted in narcosis
and death within a day.  An LD,.n value of 1620 mg/kg body weight has
                    7
been given for rats.
Chronic Poisoning - Monkeys and rabbits were exposed for 6 hours per day,
5 days per week, for 10 weeks to various concentrations of cyclohexanone.
At 190 ppm there were no detectable effects or abnormal behavior except
very slight liver and kidney injury.  At 309 ppm, there was slight eye
irritation.  At 773 ppm, salivation increased as did eye irritation.
Death occurred among animals exposed to 3082 ppm after 3 weeks of the
exposure periods.  Prior to death the animals became lethargic, showed
loss of coordination, secreted mucus, and entered a narcotic state.  No
hematological disorders could be linked to cyclohexanone exposure.
10
Effects on Vegetation
The effects of cyclohexanone on plants have not been documented in the
literature.  However, due to its properties as a solvent and as a

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defatting agent, it would act as an acute contact poison on plant parts,
especially the leaves.

Other Effects
Cyclohexanone can be used as a sole carbon source for growth by a species
of bacteria.    Due to its properties as a solvent, it could attack
and dissolve some rubbers and plastics.

AMBIENT CONCENTRATIONS AND MEASUREMENT

Ambient Concentration Estimates

Although cyclohexanone emissions are greatest from the solvent usage
source category, these sources tend to be small and geographically
scattered.  Production of cyclohexanone, however, occurs at a few loca-
tions for which the emissions characteristics can be fairly well defined,
and which as single point or area sources have a large emission density.

The largest installation for cyclohexanone production is located in a
town of about 1,800 population, and it has a capacity of about 240 mil-
lion Ib/yr.  Assuming a 1 percent loss, this converts to an emission
rate of:

(0.01 emission factor) (240 x 1Q6 Ib/yr) (453.6 g/lb)
                 3.1536 x 107 sec/yr

                                            = 34.5 g/sec of cyclohexanone.

Some assumptions must be made regarding this release to the atmosphere.
First of all, the emissions do not all come from one source location,
but rather from a number of locations within the plant where vapor leaks
to the atmosphere.  Thus, the emissions can be characterized as coming

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from an area source which will be taken to be 100 meters on a side.
Secondly, the emissions occur at different heights, and an average
emission height of 10 meters is assumed.

Ground level concentrations can then be estimated at locations downwind
                12
of the facility.    To do this a virtual point source of emission is
assumed upwind of the facility at a distance where the initial horizontal
dispersion coefficient equals the length of a side of the area divided by
4.3.  In this case:

                        a   = 100m/4.3 = 23.3m .
                         yo

Assuming neutral stability conditions (Pasquill-Gifford Stability Class D)
with overcast skies and light winds, the upwind distance of the virtual
point source is approximately 310 meters.  With consideration of the plant
boundary, it is reasonable to assume that the nearest receptor location
is thus about 500 meters from the virtual point source.  Finally, taking
2 m/sec as an average wind speed, the ground level concentration may be
calculated from:
                   X =
                       V7TC7  CT
                          y z
                             %.5         -U-LU-'2
or                 X =
                        (2)  TT  (36)  (18.5)

                     = 7.124 x 10"3 g/m3
for a 10-minute average concentration.  Over a period of an hour this
becomes (7.124 x io"3 g/m3) (0.72) = 5.129 x IO"3 g/m3 or 1.3 ppm 1-hour
average concentration.  Over a 24-hour period, the average concentration
might roughly be expected to be about 1.0 ppm.

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Measurement Techniques
Measuring cyclohexanone in air involves its adsorption on charcoal with
                                                          13
subsequent desorption and analysis by a gas chrotnatograph.
In this method a known volume of air is drawn through a charcoal tube
on which the organic vapors are adsorbed.  The tube is then transferred
to a small stoppered container where it is desorbed with carbon disulfide.
An aliquot of the desorbed sample is injected into a gas chromatograph.
The area of the resulting peak is determined and compared with areas
obtained from the injection of standards.  Concentrations in the range
of 2.5 to 125 ppm can be readily detected by this method.  Interferences
will result if the amount of water in the air is so great that condensa-
tion in the tube will affect the collection efficiency, and other inter-
ferences will result from compounds having similar retention times.
This technique is especially well suited for air pollution work, since
there is no requirement for special chemicals in the field.

SOURCES OF CYCLOHEXANONE EMISSIONS

Cyclohexanone Production and Consumption

The production of cyclohexanone in 1974 was approximately 850 million
pounds, and it is expected to increase at 10 percent per year for the
next several years.    Presently, about 43 percent of all cyclohexanone
is used to make caprolactam for nylon 6 and 52 percent is oxidized as
mixed oil (cyclohexanone and cyclohexanol) to make adipic acid.  The
remaining 5 percent is used as a solvent.  Nine companies at ten lo-
cations are producing both cyclohexanone and cyclohexanol.  The names
and locations of production facilities are given in Appendix A.

The consumption of cyclohexanone for final products is shown in
Table 3.

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            Table 3.   CYCLOHEXANONE  CONSUMPTION    197414'15
Product
Adipic acid
Caprolactam
Solvent
Million pounds
442
365.5
42.5
"1, Annual
growth
5.5
17.0
5.0
Cyclohexanone Sources and Emission Estimates

Primary sources of emissions of cyclohexanone result from solvent usage,
production losses, and bulk storage.  Total emissions from all categories
in 1974 are estimated to have been 51.3 million pounds as shown"in Table 4,
representing 6 percent of total production.
              Table 4.   SOURCES AND EMISSION ESTIMATES OF
                        CYCLOHEXANONE -  1974
                  Source
             Solvent usage
             Production losses
             Storage
                             Total
Million pounds
     42.5
      8.5
      0.3
     51.3
The major source of cyclohexanone emissions results from its use as a
solvent.  It  is used  in the manufacture of lacquers and crude rubber,
as a spot remover, and as a degreaser for leather.  Since 1967, sales
have increased due to its use as a solvent for coatings, especially as
a replacement for isophorone in vinyl solution coatings.  This replacement
is due mainly to avoid new solvent regulations, since cyclohexanone is
                                 10

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considered a nonreactive solvent.  However, a recent EPA report has
classified it as highly reactive.    Assuming that all cyclohexanone
used as a solvent will evaporate to the atmosphere, 42.5 million pounds
of cyclohexanone are emitted due to solvent usage.

The second major source of emissions occurs from the production of
cyclohexanone.  Most cyclohexanone and cyclohexanol is prepared as a
mixture by the catalytic oxidation of cyclohexane.  If only cyclo-
hexanone is desired, the cyclohexanone/cyclohexanol mixture can be
dehydrogenated with a zinc oxide catalyst to give an essentially pure
product.  Cyclohexanone may also be produced by the hydrogenation of
phenol using a palladium on carbon catalyst.  Palladium emissions may
result from the process operation and from the disposal of spent bed
material.

Since data are not available concerning emissions from these processes,
                                          17 18
based on other similar chemical processes,  '   it is estimated that
1 percent of production is emitted as cyclohexanone resulting in 8.5
million pounds of emissions.

The last major source of emissions results from bulk storage of cyclo-
hexanone.  Using emission factors in AP-42   and assuming all storage
tanks are fixed roof, emissions are 0.3 million pounds.

CYCLOHEXANONE EMISSION CONTROL METHODS

The literature does not report specific control equipment for cyclohexanone,
but it does report on control devices for other similar hydrocarbons.
Two types of control devices are presently used by the industry to con-
trol hydrocarbon emissions:  vapor recovery and incineration.  Both
systems have reported efficiencies of at least 95 percent.

Control of hydrocarbon emissions by adsorption on activated charcoal
is generally applied when recovery of adsorbed material is economically
                              11

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desirable.  Because  of  the heat generated  in adsorbing ketones, the tem-
perature  of the  bed  must  be  cooled by  adding moisture to the gas stream.
Adsorption is  generally used when concentrations of hydrocarbons are
                      19
greater than 2500  ppm.    Other applications are for the control of very
low concentration  hydrocarbons that  are  poisonous  to catalytic incinerators,
and for collection and  concentration of  low concentration emissions for
subsequent disposal by  incineration.   Cost data for the cases utilizing
adsorption are presented  in  Tables 5 and 6» The three cases presented are
adsorption with  solvent recovery, adsorption with  incineration, and ad-
sorption  with  incineration plus heat recovery.
      Table 5.  ESTIMATED INSTALLED COSTS8 OF ADSORPTION SYSTEMS
                                                                20
Adsorber capacity, SCFM
based on 25 percent lower
explosive limit
With solvent recovery, $
With thermal incineration/
no heat recovery, $
With thermal incineration/
primary heat recovery, $
1,000
74,000
89,500
101,500
10,000
162,300
202,000
255,000
20,000
280,000
344,000
431,000
 Costs updated to first quarter 1975.
                                             a                      20
   Table 6.  ESTIMATED ANNUAL OPERATING COSTS  OF ADSORPTION SYSTEMS
•Adsorber capacity, SCFM -
based on 25 percent lower
explosive limit
With solvent recovery, $/yr
With thermal incineration/
no heat recovery, $/yr
With thermal incineration/
primary heat recovery, $/yr
1,000
13,200
23,400
25,600
10,000
10,479b
64,300
82,000
20,000
37,200b
123,200
141,600
••J
 Costs updated to first quarter 1975.
b.
 Indicates a savings.
                                  12

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Control of cyclohexanone emissions by incineration or catalytic oxidation
involves direct oxidation of the combustible portion of the effluent, the
desired ultimate products being water and carbon dioxide.

The primary advantage of catalytic incineration is that extremely small
concentrations of organics can be oxidized with only small amounts of
supplemental fuel required.  The main disadvantages are the higher
capital cost and the fact that certain hydrocarbons may poison the
catalyst.  Cost data for thermal and catalytic incinerators with and
                                                      20
without heat recovery are presented in Tables 7 and 8.

Control of emissions from storage tanks will require the use of floating
roof tanks or venting the emissions to the previously mentioned "adsorber
or incinerator.  Emissions from fixed roof tanks can be vented to either
system without any major increase in cost.  If these systems are not
available, the fixed roof tanks should be switched to floating roof tanks
resulting in a 90 percent reduction of emissions.  Figure 1 provides esti-
                                              20
mated costs of various gasoline storage tanks.    These equipment cost
estimates can also be applied to cyclohexanone.  As can be seen, conversion
of fixed roof to floating roof tanks by installation of internal floating
covers is more economical than the installation of new pontoon floating
tanks.
                                 13

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           Table 7.  ESTIMATED INSTALLED COSTS  OF THERMAL
                     AND CATALYTIC INCINERATORS20
Incinerator capacity, SCFM -
based on 25 percent lower
explosive limit
Installed costs, $
Catalytic without heat recovery
Catalytic with primary heat
recovery
Catalytic with primary and
secondary heat recovery
Thermal without heat recovery
Thermal with primary heat
recovery
Thermal with primary and
secondary heat recovery
1,000

43,500
54,100
68,300
27,200
40,300
54,400
10,000

272,000
306,000
361,800
92,500
144,200
200,000
20,000

504,600
573,900
666,400
137,400
232,600
322,300
Costs updated to first quarter 1975,
       Table  8.   ESTIMATED ANNUAL OPERATING  COSTS   OF THERMAL
                  AND  CATALYTIC  INCINERATORS20
Incinerator capacity, SCFM -
based on 25 percent lower
explosive limit
Operating costs, $/yr
Catalytic without heat recovery
Catalytic with primary heat
recovery
Catalytic with primary and
secondary heat recovery
Thermal without heat recovery
Thermal with primary heat
recovery
Thermal with primary and
secondary heat recovery
1,000

16,200
16,400

19,300
12,000
11,500

14,400
10,000

102,800
78,500

108,700
54,300
36,300

50,800
20,000

195,000
177,900

203,700
96,700
59,200

84,500
Costs updated to first quarter 1975.
                                 14

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     500 -
      400
      300
   8
   "J  200
   _»
   <
      100
           T~l   I'  I   1   1—i  I   i—1   1   i
                 Told Coil Cono Roof Tank Converted
                 with Internal Floating Roof
                               i   1   1    1   I

                                     /
                 Pontoon Floating
                 Roof Tank
                                                 Cona Roof Tank
                               Internal  FIool  Cover en Existing Cone
                               Roof  Tank (Incremental Cost - Conversion)
                  I   I   t   I   1   I
                                        »
50              100
     CAPACITY, barrels
                                                      150
200
Figure  1.   Estimated  installed  cost of cyclohexanone storage tanks
            (equipment costs assumed to be  the same as gasoline
            storage  tanks)20
                                    15

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                              SECTION III

                              REFERENCES
 1.  American Industrial Hygiene Association.  Hygienic Guide Series:
     Cyclohexanone.  Amer Ind Hyg Assoc J.  26:630-34, 1965.

 2.  Rowe, V.K., M.A. Wolf.  Ketones.  In:  Industrial Hygiene and
     Toxicology, Patty, F.A. (ed.).  New York,"Interscience Publishers,
     Vol. II, 2nd edition,. 1963.  p. 176-68.

 3.  Nelson, K.W., J.F. Ege, Jr., M. Ross, L.E. Woodman,  and  L.  Silverman.
     Sensory Response to Certain Industrial Solvent Vapors.  J Ind Hyg
     Toxicol.  25:282-85, 1943.

 4.  The Toxic Substances List 1974 Edition.  HEW Publication No.  (NIOSH)
     74-134, p. 235.

 5.  NIOSH/OSHA Draft Technical Standards:  Cyclohexanone.   3 January 1975.

 6.  Smyth, 'J.F.  Improved Communication.  Hygienic Standards for  Daily
     Inhalation.  Am Ind Hyg Assoc Quart.  17:129-185, 1956.

 7.  Smith, H.F., C.P. Carpenter, C.S.  Weil, U.C. Pozzanij  J.A.  Striegel,
     and J.S. Nycum.  Range Finding Toxicity Data.   List  VII. Am  Ind
     Hyg Assoc J.  30:470-76, 1969.

 8.  Treori, J.F., W.E. Crutchfield, Jr.,  and K.V. Kitzmiller. The
     Physiological Response of Rabbits  to Cyclohexane, Methylcyclohexane,
     and Certain Derivatives of Those Compounds.   J Ind Hyg Toxicol.
     25:199-213, 1943.

 9.  Carpenter, C.P., H.F. Smyth, Jr.  Chemical Burns  of  the  Rabbit
     Cornia.  Amer J Opthalmol.  25:1363, 1946.

10.  Treon, J.F., W.E. Crutchfield, Jr.,  and K.V. Kitzmiller.  The Physio-
     logical Response to Animals to Cyclohexane,  Methylcyclohexane,  and
     Certain Derivatives of These Compounds.  J Ind Hyg Toxicol.   25:
     323-47, 1943.
                                 16

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11.  Murray, J.P., T.A. Scheikowski, and I.e.  MacRae.   Utilization of
     Cyclohexanone and Related Substances by a Nocardia Sp. Ant.  van
     Leeuwenhoek.  40:17-24, 1974.

12.  Turner, D.B.  Workbook of Atmospheric Dispersion  Estimates.
     U.S. Environmental Protection Agency.  Report Number  AP-26.
     January 1973.

13.  U.S. Department of Health, Education and Welfare  (NIOSH), Div. of
     Laboratories and Criteria Development.  May 1975.

14.  Chemical Economics Handbook.  Stanford Research Institute, June 1973,

15.  Chemical Profiles.  Schnell Publishing Co.  1966.

16.  U.S. EPA, Guideline on Use of Reactivity Criteria in  Control of
     Organic Emissions for Reduction of Atmospheric Oxidants.  Internal
     Draft.  August 13, 1975.

17.  Compilation of Air Pollutant Emission Factors. U.S.  Environmental
     Protection Agency.  Report Number AP-42.   April 1973.

18.  Survey Reports on Atmospheric Emissions from the  Petrochemical
     Industry.  Volume 1.  Report Number EPA-450/3-73-005a.  January
     1974.

19.  Laufer, J.  The Control of Solvent Vapor Emissions.   N.Y. State
     Department of Health.  January 1969.

20.  Hydrocarbon Pollutant Systems Study.  MSA Research Corp.  NTIS
     Publication No.  PB-219-073.  October 1972.
                                 17

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                              APPENDIX A
                      CYCLOHEXANONE MANUFACTURERS
Allied Chemical Corp.
Celanese Corp.
Dow Badische Co.
DuPont
El Paso Natural Gas Co.
Monsanto Co.
Monsanto Co.
Nipro
Rohm and Haas Co.
Union Carbide Corp.
Hopewell, Virginia
Bay City, Texas
Freeport, Texas
Belle, West Virginia
Odessa, Texas
Luling, Louisiana  I
Pensacola, Florida J
Augusta, Georgia
Louisville, Kentucky
Taft, Louisiana
       Total
Estimated capacity,
   million Ib/yr
        173
         50
        125
        240
         32
        250

         75
         20
         35
       1000
                                18

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