,J

Page! 1 of 4

ACETONITRILE

CASRN: 75-05-8

For other data, click on the Table of Contents

Chemical/Physical Properties :

Molecular Formula :

C2-H3-N

**PEER REVIEWED* *

Molecular Weight:

41 .0 5

[Budavari, S . (ed .) . The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals . Whitehouse

Station, NJ : Merck and Co ., Inc ., 1996 . 13]**PEER REVIEWED "

Color/Form:

Colorless, limpid liquid

[Lewis, R .J ., Sr (Ed .) . Hawley's Condensed Chemical. Dictionary . 13th ed . New York, NY : John Wiley & Sons,

Inc . 1997 . 9)**PEER REVIEWED* *

Odor:

Aromatic odor

[NIOSH . NIOSH Pocket Guide to Chemical Hazards . DHHS (NIOSH) Publication No . 97-140 . Washington, D .C .

U.S . Government Printing Office, 1997 . 4)**PEER REVIEWED* *

Ether-like odor

[Budavari, S . (ed .) . The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals . Whitehouse

Station, NJ: Merck and Co ., Inc ., 1996 . 13)**PEER FtEVIEWED* *

Taste :

BURNING SWEETISH TAST E

[National Fire Protection Association . Fire Protection Guide on Hazardous Materials . 9th ed . Boston, MA :

National Fire Protection Association, 1986 .,p . 49- :_0]**PEER REVIEWED* *

Boiling Point:

81 .6degC@760mmHg

[Budavari, S . (ed .) . The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals . Whitehouse

Station, NJ : Merck and Co ., Inc ., 1996 . 13]**PEER REVIEWED* *

Melting Point:

-45 deg C

[Budavari, S . (ed .) . The Merck Index - An Encyclope:dia of Chemicals, Drugs, and Biologicals . Whitehouse

Station, NJ: Merck and Co ., Inc ., 1996 . 13]**PEER REVIEWED* *

Corrosivity :

Liquid acetonitrile will attack some forms of plastics, rubber, and r,oatings.

[Mackison, F . W ., R . S . Stricoff, and L . J . Partridge, Jr . (eds .) . NIOSH/OSHA - Occupational Health

Guidelines for Chemical Hazards . DHHS(NIOSH) PublicationNo . 81-123 (3 VOLS) . Washington, DC : U .S .

Government Printing Office, Jan . 1981 . 2]**PEER REVIEWED* *

Critical Temperature & Pressure:

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Critical temperature = 272 .3 deg C; critical pressure = 47 .7 atm

[Riddick, J .A., W .B . Bunger, Sakano T .K . Techniques of Chemistry 4th ed ., Volume II . Organic Solvents .

New York, NY : John Wiley and Sons ., 1985 . 582]**PEER REVIEWED* *

Density/Specific Gravity:

SP GR: 0 .78745 @ 15 deg C/4 deg C

[Budavari, S . (ed .) . The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals . Whitehouse

Station, NJ: Merck and Co ., Inc ., 1996 . 13]**PEER REVIEWED* *

Dissociation Constants:

pKa = -4.30

[Perrin DD ; Dissociation Constants of Organic Bases in Aqueous Solution . IUPAC Chem Data Ser,

Buttersworth, London pp . 15 (1965)]**PEER REVIEWED* *

Heat of Combustion:

31 .03X10+6 J/kg @ 25 deg C

[Kirk-Othmer Encyclopedia of Chemical Technology . 4th ed . Volumes 1 : New York, NY . John Wiley and Sons,

1991-Present .,p . SUPP (1998) 442]**PEER REVIEWED* *

Heat of Vaporization :

72 .7X 10+4 J/kg @ 80 deg C

[Kirk-Othmer Encyclopedia of Chemical Technology . 4th ed . Volumes 1 : New York, NY . John Wiley and Sons,

1991-Present .,p . SUPP (1998) 4423**PEER REVIEWED* *

Octanol/Water Partition Coefficient :

log Kow= -0 .34

[Hansch, C ., Leo, A ., D . Hoekman . Exploring QSAR - Hydrophobic, Electronic, and Steric Constants .

Washington, DC : American Chemical Society ., 1995 . 4]**PEER REVIEWED* *

Solubilities:

Miscible with methanol, methyl acetate, acetone, ethyl acetate, ether, acetamide solutions, chloroform, carbon tetrachloride, ethylene

chloride, and with many unsaturated hydrocarbons; immiscible with many saturated hydrocarbons; dissolves somewhat in inorg salts such

as silver nitrate, lithium nitrate, magnesium bromide .

[Budavari, S . (ed.) . The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals . Whitehouse

Station, NJ : Merck and Co ., Inc ., 1996 . 13]**PEER REVIEWED* *

Soluble in alcohol

[Lewis, R .J ., Sr (Ed .) . Hawley's Condensed Chemical Dictionary . 13th ed . New York, NY : John Wiley & Sons,

Inc . 1997 . 9]**PEER REVIEWED* *

MISCIBLE WITH BENZEN E

[Lide, D .R . (ed) . CRC Handbook of Chemistry and Physics . 72nd ed . Boca Raton, FL : CRC Press, 1991-

1992 .,p . 3-221**PEER REVIEWED* *

Equal wt of acetonitrile and the following materials are miscible at room temp : formic acid, acetic acid, levulinic acid, methanol,

cellosolve solvent, formaldehyde, acetaldehyde, di-n-butyl amine, acetic anhydride, pyridine, nitrobenzene, aniline, xylene, phenol, acetyl

chloride, dibutyl phthalate, diglycol stearate, n-butyl ether, dichloroethyl ether, methyl isobutyl ketone, nitromethane, nitroethane,

nitropropane

[Flick, E .W . Industrial Solvents Handbook . 3rd ed . Park Ridge, NJ : Noyes Publications, 1985 . 578)**PEER

REVIEWED* *

In water, infinite solubility @ 25 deg C

[Riddick, J .A., W .B . Bunger, Sakano T .K . Techniques of Chemistry 4th ed ., Volume II . Organic Solvents .

New York, NY : John Wiley and Sons ., 1985 . 583]**PEER REVIEWED**

Spectral Properties:

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Index of refraction : 1 .33934 @ 30 deg C/D

[Budavari, S . (ed .) . The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals . Whitehouse

Station, NJ : Merck and Co ., Inc ., 1996 . 13]**PEER REVIEWED* *

MAX ABSORPTION: 274 NM (LOG E= 2.7) UNDILUTED

[Weast, R .C . (ed .) . Handbook of Chemistry and Physics . 60th ed . Boca Raton, Florida : CRC Press Inc .,

1979 .,p . C-871**PEER REVIEWED* *

Acetonitrile, 99%, exhibits its two strongest infra red absorption bands at wavelengths of 7 .0 and 7 .3 micrometers.

[Aldrich; The Aldrich Microfiche Library of Chemical Indices (1983)]**PEER REVIEWED**

IR: u SADP 269 (Sadder Research Laboratories Prism Collection)

[Lide, D .R., G .W .A . Milne (eds .) . Handbook of Data on Organic Compounds . Volume I . 3rd ed . CRC Press,

Inc . Boca Raton FL . 1994 .,p . V1 187]**PEER REVIEWED* *

UV: OES 4-2 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York )

[Lide, D .R ., G .W .A . Milne (eds .) . Handbook of Data on Organic Compounds . Volume I . 3rd ed . CRC Press,

Inc . Boca Raton FL . 1994 .,p . V1 187]**PEER REVIEWED* *

1H NMR: SAD 9154 (Sadtler Research Laboratories Spectral Collection)

[Lide, D .R., G .W.A . Milne (eds .) . Handbook of Data on Organic Compounds . Volume I . 3rd ed . CRC Press,

Inc . Boca Raton FL . 1994 .,p . V1 187]**PEER REVIEWED* *

MS : NIST 18850 (NIST/EPA/MSDC Mass SPectral Database 1990 version)

[Lide, D .R., G .W.A . Milne (eds .) . Handbook of Data on Organic Compounds . Volume I . 3rd ed . CRC Press,

Inc . Boca Raton FL . 1994 .,p . V1 1871**PEER REVIEWED* *

Surface Tension:

29 .04 dynes/cm @ 20 deg C

[Budavari, S . (ed .) . The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals . Whitehouse

Station, NJ : Merck and Co ., Inc ., 1996 . 131**PEER REVIEWED* *

Vapor Density:

1 .42 (air=1)

[Clayton, G .D ., F .E . Clayton (eds .) Patty's Industrial Hygiene and Toxicology . Volumes 2A, 2B, 2C, 2D,

2E, 2F : Toxicology . 4th ed . New York, NY : John Wiley & Sons Inc ., 1993-1994 . 3141]**PEER REVIEWED**

Vapor Pressure:

88 .8mmHg@25degC

[Boublik, T ., Fried, V ., and Hala, E ., The Vapour Pressures of Pure Substances . Second Revised Edition.

Amsterdam : Elsevier, 1984 .]**PEER REVIEWED* *

Relative Evaporation Rate :

5 .79 (butyl acetate= 1 )

[Kirk-Othmer Encyclopedia of Chemical Technology . 4th ed . Volumes 1 : New York, NY . John Wiley and Sons,

1991-Present .,p . SUPP (1998) 442]**PEER REVIEWED* *

Viscosity :

0 .35cP@20degC

[Kirk-Othmer Encyclopedia of Chemical Technology . 4th ed . Volumes 1 : New York, NY . John Wiley and Sons,

1991-Present .,p . SUPP (1998) 442]**PEER REVIEWED* *

Other Chemical/Physical Properties:

PERCENT IN SATURATED AIR 9.6; DENSITY OF SATURATED AIR 1 .04 (AIR= 1).

[Clayton, G .D ., F .E . Clayton (eds .) Patty's Industrial Hygiene and Toxicology . Volumes 2A, 2B, 2C, 2D,

2E, 2F : Toxicology . 4th ed . New York, NY: John Wiley & Sons Inc ., 1993-1994 . 3141]**PEER REVIEWED* *

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High polarity ; strongly reactiv e

[Lewis, R .J ., Sr (Ed .) . Hawley's Condensed Chemical Dictionary . 13th ed . New York, NY : John Wiley & Sons,

Inc . 1997 . 9]**PEER REVIEWED* *

Burns with luminous flame ; dielectric constant : 38.8 @ 20 deg C ; constant boiling mixture with water contains 16% H20 and bp : 76 deg C

[Budavari, S . (ed .) . The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals . Whitehouse

Station, NJ : Merck and Co ., Inc ., 1996 . 13)**PEER REVIEWED* *

Sat concn 163 g/cu in at 20 deg C, 249 g/cu in at 30 deg C

[Clayton, G .D ., F .E . Clayton (eds .) Patty's Industrial Hygiene and Toxicology . Volumes 2A, 2B, 2C, 2D,

2E, 2F: Toxicology . 4th ed . New York, NY : John Wiley & Sons Inc ., 1993-1994 . 117]**PEER REVIEWED**

Saturated liquid density : 48 .7301b/cu ft; liquid heat capacity : 0.540 Btu/lb-F ; saturated vapor pressure : 1 .383 lb/sq in; saturated vapor

density : 0 .00998 lb/cu ft (all at 70 deg F)

[U .S . Coast Guard, Department of Transportation . CHRIS - Hazardous Chemical Data . Volume II . Washington,

D .C . : U .S . Government Printing Office, 1984-5 .]**PEER REVIEWED* *

Specific heat= 0.541 Btu/lb/deg F (21 deg to 76 deg C)

[Flick, E .W . Industrial Solvents Handbook . 3rd ed . Park Ridge, NJ : Noyes Publications, 1985 . 577 ] **PEER

REVIEWED* *

Dielectric constant= 42 .0 @ 0 deg C, 38.8 (0,20 deg C, 26.2 @ 81 .6 deg C

[Flick, E .W . Industrial Solvents Handbook . 3rd ed . Park Ridge, NJ : Noyes Publications, 1985 . 577]**PEER

REVIEWED* *

Heat of fusion = 21 .8X10+4 J/kg @-45 .7 deg C; heat capacity (liquid) = 22 .59X10+2 J/kg K@ 20 deg C; coefficient of expansion (@ 20

deg C) = 1 .37X10-3/deg C ; specific conductance = 5X10-8 S to 9X10-8 S@ 25 deg C; dipole moment = 10.675X10-30 C-m; dielectric

constant = 42.0 @ 0 deg C, 38 .8 @ 20 deg C, 26.2 @ 81 .6 deg C.

[Kirk-Othmer Encyclopedia of Chemical Technology . 4th ed . Volumes 1 : New York, NY . John Wiley and Sons,

1991-Present .,p . SUPP (98) 4421**PEER REVIEWED* *

Henry's Law constant = 3 .45X10-5 atm-cu m/mole @ 25 deg C

[Gaffney JS et al ; Environ Sci Technol 21 : 519-23 (1987)]**PEER REVIEWED**

Hydroxyl radical reaction rate constant = 2.63X10-14 cu cm/molecule-sec @ 25 deg C

[Atkinson R; J Phys Chem Ref Data . Monograph 2(1994)]**PEER REVIEWED**

Ideal gas heat capacity = 52 .22 J/K mo l

[Riddick, J .A., W .B . Bunger, Sakano T .K. Techniques of Chemistry 4th ed ., Volume II . Organic Solvents .

New York, NY : John Wiley and Sons ., 1985 . 582]**PEER REVIEWED**

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ACETONITRILE

CASRN: 75-05- 8

For other data, click on the Table of Contents

Manufacturing/Use Information :

Major Uses:

In organic synthesis as starting material for acetophenone, alpha-naphthaleneacetic acid, thiamine, acetamidine . To remove tars, phenols, &

coloring matter from petroleum hydrocarbons which are not soluble in acetonitrile. To extract fatty acids from fish liver oils & other

an imals & vegetable oils. Can be used to recrystallize steroids. As an indifferent medium in physicochemical investigations . Wherever a

polar solvent having a rather high dielectric constant is required . As medium for promoting reactions involving ionization . As a solvent in

non-aqueous titrations. As a nonaqueous solvent for inorg anic salts.

[Budavari, S . (ed .) . The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals . Whitehouse

Station, NJ : Merck and Co ., Inc ., 1996 . 13]**PEER REVIEWED* *

Acrylic fibers; phannaceuticals; perfumes; nitrile rubber ; ABS resin s

[Sax NI, ed; Danger Props Indus Mater Report 4 (1) : 44-6 (1985))**PEER REVIEWED* *

Acetonitrile is used as a chemical intermediate in pesticide m an ufacture .

[Sittig, M . Handbook of Toxic and Hazardous Chemicals and Carcinogens, 1985 . 2nd ed . Park Ridge, NJ :

Noyes Data Corporation, 1985 . 29]**PEER REVIEWED* *

Starting material for many types of nitrogen-containing compounds, eg, amides, amines, higher molecular weight mono- and dinit ri les;

halogenated nitriles; ketones; isocy anates; and heterocycles, eg, pyridines and imidazoline s

[Kirk-Othmer Encyclopedia of Chemical Technology . 4th ed . Volumes 1 : New York, NY . John Wiley and Sons,

1991-Present .,p . SUPP (1998) 4421**PEER REVIEWED* *

Acetonitrile is used as a solvent remover of acry lic sculpted nails that are bonded to the natural nail with durable glues.

[Ellenhorn, M.J ., S . Schonwald, G . Ordog, J . Wasserberger . Ellenhorn's Medical Toxicology : Diagnosis and

Treatment of Human Poisoning . 2nd ed . Baltimore, MD : Williams and Wilkins, 1997 . 1484]**PEER REVIEWED* *

Solvent in hydrocarbon extraction processes, especially for butadiene ; specialty solvent; intermediate ; catalyst; separation of fatty acids

from vegetable oils.

[Lewis, R .J ., Sr (Ed .) . Hawley's Condensed Chemical Dictionary . 13th ed . New York, NY : John Wiley & Sons,

Inc . 1997 . 91**PEER REVIEWED* *

Widely used as a recoverable reaction medium, pa rticularly for the preparation of pharmaceuticals; used in the separation of other olefins

(eg propylene, isoprene, allene, and methylactylene) fr om hydrocarbon streams; used as a solvent for polymers, spinning fibers, and c asting

and molding plastics; used with spectr ophotometry, elec trochemistry, and high pressure liquid chromatography ; used as a catalyst and

ingredient in transition metal complex catalysts, in the photographic indust ry, and for the ex traction and refining of copper and by-product

ammonium sulfate; used for dyeing textiles and in coating compositions; used as a stabilizer for chlorinated solvents in the presence of

aluminum; used in the manufacture of perfumes and as reagent in a wide variety of compounds.

[Kirk-Othmer Encyclopedia of Chemical Technology . 4th ed . Volumes 1 : New York, NY . John Wiley and Sons,

1991-Present .,p . SUPP (1998) 443)**PEER REVIEWED* *

Used as solvent in lithium-sulfur dioxide elec trochemical cells.

[Kirk-Othmer Encyclopedia of Chemical Technology . 4th ed . Volumes 1 : New York, NY . John Wiley and Sons,

1991-Present .,p . V3 (1992) 1022]**PEER REVIEWED* *

Manufacturers :

BP Amoco Corp ., 200 E . Randolph Dr., Chicago, IL 60601, ( 312) 856-6111 : Production site : Green Lake, TX 77031 ; Lima, OH 45804

[SRI International . 2000 Directory of Chemical Producers -- United States . SRI Consulting, Menlo Park : CA

2000 437)**PEER REVIEWED* *

DuPont. Dupont Specialty Chemicals, 1007 Market St., Wilmington, DE 19898, (800) 441-7515 ; Production site : Beaumont, TX 77704

[SRI International . 2000 Directory of Chemical Producers -- United States . SRI Consulting, Menlo Park : CA

2000 4371**PEER REVIEWED* *

Sterling Chemicals, Inc ., 1200 Smith St ., Suite 1900, Houston, TX 77002-4312, (713) 650-3700 ; Production site : Texas City , TX 77590

[SRI International . 2000 Directory of Chemical Producers -- United States . SRI Consulting, Menlo Park : CA

2000 437]**PEER REVIEWED* *

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Methods of Manufacturing :

By-product of propylene-ammonia process for acrylonitril e

[Lewis, R .J ., Sr (Ed .) . Hawley's Condensed Chemical Dictionary . 13th ed . New York, NY : John Wiley & Sons,

Inc . 1997 . 9]**PEER REVIEWED* *

Prepd indust by dehydration of acetamide .

[Budavari, S . (ed .) . The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals . Whitehouse

Station, NJ : Merck and Co ., Inc ., 1996 . 13]**PEER REVIEWED* *

By reacting acetic acid with ammonia at 400-500 deg C in the presence of a dehydration catalyst .

[Snyder, R . (ed .) . Ethyl Browning's Toxicity and Metabolism of Industrial Solvents . 2nd ed . Volume II :

Nitrogen and Phosphorus Solvents . Amsterdam-New York-Oxford : Elsevier, 1990 . 3011**PEER REVIEWED**

General Manufacturing Information :

All of the acetonitrile produced commercially in the United States in 1980 was produced as an isolated by-product from the manufacture

of acrylonitrile via propylene ammoxidation .

[Kirk-Othmer Encyclopedia of Chemical Technology . 4th ed . Volumes 1 : New York, NY . John Wiley and Sons,

1991-Present .,p . SUPP (1998) 442]**PEER REVIEWED* *

Formulation s/Preparations:

Grades: technical; nanograde ; spectrophotometric .

[Lewis, R .J ., Sr (Ed .) . Hawley's Condensed Chemical Dictionary . 13th ed . New York, NY : John Wiley & Sons,

Inc . 1997 . 9]**PEER REVIEWED* *

Impurities :

The principal organic impurity in commercial acetonitrile is propionitrile ; small amounts of allyl alcohol may be present .

[Kirk-Othmer Encyclopedia of Chemical Technology . 4th ed . Volumes 1 : New York, NY . John Wiley and Sons,

1991-Present .,p . SUPP (1998) 443]**PEER REVIEWED* *

Acidity (max), 0 .05 wt%; copper (max), 0 .5 ppm; iron (max), 0 .5 ppm; water (max), 0.3 wt%

[Kirk-Othmer Encyclopedia of Chemical Technology . 4th ed . Volumes 1 : New York, NY . John Wiley and Sons,

1991-Present .,p . SUPP (1998) 443]**PEER REVIEWED* *

Maximum limits of impurities: residue after evaporation 0 .0005%, acidity (as acetic acid) 0 .03%, alkalinity (as ammonia) 0 .001%, water

0 .05%. /'Photrex' Reagent, for spectrophotometry /

[JT Baker Chemical Co ; Reagents and Laboratory Products Catalog 860C p .3 (1986)]**PEER REVIEWED**

U. S . Production :

(1972) PROBABLY GREATER THAN 4.54X10+5 G

[SRI]**PEER REVIEWED* *

(1989) 3.5X10+7l b

[United States International Trade Commission . Synthetic Organic Chemicals- United States Production and

Sales, 1988 . USITC Publication 1989 . Washington,DC : United States International Trade Commission,

1989 .,p . 15-41**PEER REVIEWED* *

(1991) Exceeded 5000 lb or US $5000 in value

[SRI . 1992 Directory of Chemical Producers-United States of America . Menlo Park, CA: SRI International,

1992 . 4341**PEER REVIEWED* *

U. S . Imports:

(1984) 9 .27X10+10 g /NITRILES, NSPF/

[BUREAU OF THE CENSUS . US IMPORTS FOR CONSUMPTION AND GENERAL IMPORTS 1984 p .1-3561**PEER REVIEWED**

U. S . Exports :

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(1984) 9.73X10+9 g/Nitriles & their derivatives, NSPF /

[BUREAU OF THE CENSUS . US EXPORTS, SCHEDULE E, 1984 p .2-81 1 **PEER REVIEWED* *

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ACETONITRILE

CASRN: 75-05- 8

For other data, click on the Table of Contents

Environmental Fate & Exposure:

Environmental Fate/Exposure Summa ry:

Acetonitrile's production and wide use as a solvent, chemical intermediate, and catalyst may result in its release to the environment

through various waste streams. If released to air, a vapor pressure of 88 .8 mm Hg at 25 deg C indicates acetonitrile will exist solely as a

vapor in the ambient atmosphere . Vapor-phase acetonitrile will be degraded in the atmosphere by reaction with photochemically-produced

hydroxyl radicals; the half-life for this reaction in air is estimated to be 621 days. If released to soil, acetonitrile is expected to have ve ry

high mobili ty based upon an estimated Koc of 16 . Volatilizati on from moist soil surfaces is expected to be an important fate process based

upon a Henry's Law constant of 3 .45X10-5 atm-cu m/mole . Acetonitrile may volatilize from dry soil surfaces based upon its vapor

pressure . If released into water, acetonitrile is not expected to adsorb to suspended solids and sediment based upon the estimated Koc .

Studies using mixed microbial cultures from ac tivated sludge and sewage have shown that biodegradati on of acetonitrile proceeds

sluggishly without acclimatization. Mixed microbial cultures isolated by an enrichment culture technique degraded 58% acetonitrile in 5

days; river water also biodegraded acetonitrile with 40% theore tical oxygen dem and after 12 days. Volatilizati on from water surfaces is

expected to be an important fate process based upon this compound's Hen ry 's Law constant. Estimated volatilization half-lives for a model

river and model lake are 12 hours and 7 days, respectively . An estimated BCF of 3 suggests the potential for bioconcentrati on in aquatic

organisms is low. The chemical hydrolysis of acetonitrile in water is base catalyzed but the rate is too slow to be an important fate process .

The chemical hydrolysis half-life at pH 7 is >150,000 years. Occupational exposure to acetonitrile may occur through inhalation and

dermal contact with this compound at workplaces where acetonitrile is produced or used . Monitoring data indicate that the general

population may be exposed to acetonitrile via ingestion of food and drinking water, and dermal contact with products containing

acetonitrile . (SRC)

**PEER REVIEWED**

Probable Routes of Human Exposure :

NIOSH (NOES Survey 1981-1983) has statistically estimated that 31,341 workers (7,975 of these are female) are potentially exposed to

acetonitrile in the US(l). Occupational exposure to acetonitrile may occur through inhalation and dermal contact with this compound at

workplaces where acetonitrile is produced or used(SRC) . Monitoring data indicate that the general popula tion may be exposed to

acetonitrile via ingesti on of food and drinking water, and dermal contact with products containing acetonitrile(SRC).

[(1) NIOSH ; National Occupational Exposure Survey (NOES) ( 1983)]**PEER REVIEWED**

Body Burden :

. . . A standardized second puff of cigarette smoke contains 0 .31 mg acetonitrile . A smoker may absorb between 73 and 82% of this,

depending on post smoking habits.

[USEPA; Chemical Hazard Information Profiles p .9 EPA-560/11-80-011 ( 1980)]**PEER REVIEWED* *

An individual who died about 2 hours after a 12 hr exposure to acetonitrile had the following cyanide concn detected in his tissues at

autopsy : blood= 8 mg/l ; lung= 1 .3 mg/kg; liver= 0 mg/kg ; kidney= 2 .0 mg/kg ; u rine= 2 .2 mg/1 .

[Baselt RC ; Biological Monitoring Methods for Industrial Chemicals p .11 (1980)]**PEER REVIEWED* *

Blood cyanide concentrati ons exceeding 0 .1 mg/1 or pl asma or urine thiocyan ate exceeding 20 mg/I in workers exposed to acetonitrile are

indicative of excessive exposure.

[Baselt RC ; Biological Monitoring Methods for Industrial Chemicals p .11 (1980)]**PEER REVIEWED**

Natural Pollution Sources :

Small amounts of acetonitrile occur in coal tar(1) .

[(1) Budavari S, ed; The Merck Index . 12th ed Whitehouse Station, NJ : Merck and Co Inc, p . 13 (1996)]

**PEER REVIEWED* *

Artificial Pollution Sources:

Acetonitrile . . . /h as/ been detected in the thermal decomp products of flexible polyureth ane foam .

[Landrock, A .H . Handbook of Plastics Flammability and Combustion Toxicology . Park Ridge, New Jersey :

Noyes Publications, 1983 . 92]**PEER REVIEWED* *

Acetonitrile's production and wide use as a solvent, chemical intermediate, and catalyst(1,2) may result in its release to the environment

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through various waste streams(SRC). Acetonitrile is rele ased in the atmosphere as a result offugitive emission during its manufacture

(3,4). Emission of acetonitrile from industri al facilities during its use also occurs(4). It is also released to the atmosphere from incineration

of polyacrylonitrile polymers(3,4), automobile exhaust(4,5), tobacco smoke(6), synthetic rubber manufacture(4), off-gas ofshale oil

retorting(7), manufacture of acrylonitrile(8) and turbine engines(4). Acetonitrile has been detected in shale oil wastewater(9, 10) and in

wastewater from coal gasification processes(10,11) .

[(1) Lewis RJ Sr, ed ; Hawley's Condensed Chemical Dictionary 13th ed NY, NY : John Wiley and Sons Inc, p .

9 (1997) (2) McKinney RJ, DeVito SC ; Kirk-Othmer Encycl Chem Tech 4th ed NY, NY : John Wiley and Sons

Supp : 442 (1998) (3) USEPA ; Chemical Hazard Information Profiles . Washington, DC : USEPA-560/11-80-011

(1980) (4) Graedel TE et al ; Atmospheric Chemical Compounds . NY, NY : Academic Press p . 389 (1986) (5)

Schuchmann HP, Laidler KJ ; J Air Pollut Control Assoc 22 : 52-3 (1972) (6) Kadaba PK et al ; Bull Environ

Contam Toxicol 19 : 104-11 (1978) (7) Sklarew DS, Hayes DJ ; Environ Sci Technol 18 : 600-3 (1984) (8)

USEPA; Locating and estimating air emissions from sources of acrylonitrile . Research Triangle Park, NC :

USEPA-450/4-84-007A (1984) (9) Hawthorne SB, Sievers RE ; Environ Sci Technol 18 : 483-90 (1984) (10)

Pellizzari ED et al ; pp . 256-74 in ASTM Spec Tech Publ STP 686 (1979) (11) Mohr DH, King CJ ; Environ Sci

Technol 19 : 929-35 (1985)]**PEER REVIEWED* *

Environmental Fate:

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 16(SRC), determined from a log Kow of -0 .34(2)

and a regression-derived equation(3), indicates that acetonitrile is expected to have very high mobility in soil(SRC). Volatilization of

acetonitrile from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 3 .45X10-5 atm-cu

m/mole(4). The potential for volatilization of acetonitrile from dry soil surfaces may exist(SRC) bas ed upon a vapor pressure of 88 .8 mm

Hg(5). In water, biode gradati on studies of acetonitrile with mixed cultures of microorgan isms from activated sludge and sewage show that

de gradation proceeds sluggishly without acclimatization of microorgan isms, particularly at high concns(6,7) . Acclimated mixed microbial

cultures isolated by an enrichment culture technique degr aded 58% acetonitrile in 5 days(8).

[(1) Swann RL at al; Res Rev 85 : 17-28 (1983) (2) Hansch C at al; Exploring QSAR . Hydrophobic,

Electronic, and Steric Constants . ACS Prof Ref Book . Heller SR, consult . ed ., Washington, DC : Amer Chem

Soc p . 4 (1995) (3) Lyman WJ at al ; Handbook of Chemical Property Estimation Methods . Washington, DC :

Amer Chem Soc pp . 4-9 (1990) (4) Gaffney JS et al; Environ Sci Technol 21 : 519-23 (1987) (5) Boublik T at

al ; The vapor pressures of pure substances . Vol 17 Amsterdam, Netherlands : Elsevier Sci Publ (1984) (6)

Kalmykova GY, Rogovskaya TI ; Biol Vnutr Vod 38 : 79-83 (1978) (7) Placak OR, Ruchhoft CC ; Sewage Works J

19 : 423-40 (1946) (8) Babeu L, Vaishnav DD ; J Ind Microbiol 2 : 107-15 (1987)]**PEER REVIEWED* *

AQUATIC FATE : Based on a cl assification scheme(1), an estimated Koc value of 16(SRC), determined from a log Kow of -0.34(2) and a

regression-de rived equation(3), indicates that acetonitrile is not expected to adsorb to suspended solids and sediment(SRC) . Volatilization

from water surfaces is expected(3) b ased upon a Henry's Law constant of 3 .45X10-5 atm-cu m/mole(4) . Using this Henry's Law constant

an d an estimation method(3), volatilization half-lives for a model ri ver and model lake are 12 hours and 7 days, respectively(SRC).

According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(6), suggests

the potential for bioconcentration in aquatic organisms is low(SRC). The biode gradation studies of acetonitrile with mixed cultures of

microorganisms from activated sludge and sewage show that degradation proceeds sluggishly without acclimatization of microorg an isms,

particularly at high concn(7,8). Acclimated mixed microbial cultures isolated by an enrichment culture technique de gr aded 58%

acetonitrile in 5 days(9). The biodegradability of acetonitrile was also observ ed with river water; the 12 day ThOD (theoretical oxygen

demand) with river water was 40%(10,11).

[(1) Swann RL at al; Res Rev 85 : 17-28 (1983) (2) Hansch C et al ; Exploring QSAR . Hydrophobic,

Electronic, and Steric Constants . ACS Prof Ref Book . Heller SR, consult . ed ., Washington, DC : Amer Chem

Soc p . 4 (1995) (3) Lyman WJ at al ; Handbook of Chemical Property Estimation Methods . Washington, DC :

Amer Chem Soc pp . 4-9, 15-1 to 15-29 (1990) (4) Gaffney JS et al ; Environ Sci Technol 21 : 519-23 (1987)

(5) Franke C et al ; Chemosphere 29 : 1501-14 (1994) (6) Meylan WM et al ; Environ Toxicol Chem 18 : 664-72

(1999) (7) Kalmykova GY, Rogovskaya TI ; Biol Vnutr Vod 38 : 79-83 (1978) (8) Placak OR, Ruchhoft CC ;

Sewage Works J 19 : 423-40 (1946) (9) Babeu L, Vaishnav DD ; J Ind Microbiol 2 : 107-15 (1987) (10) Ludzack

FJ et al; Proc 13th Ind Waste Conf Purdue Univ Eng Ext Service, p. 297-312 (1958) (11) Ludzack FJ,

Ettinger MB ; Water Pollut Control Assoc J 32 : 1173-2000 (1960)1**PEER REVIEWED* *

ATMOSPHERIC FATE : According to a model of gas/particle partitioning of semivolatile organ ic compounds in the atmosphere(1),

acetonitrile, which has a vapor pressure of 88 .8 mm Hg at 25 deg C(2), is expected to exist solely as a vapor in the ambient atmosphere

(SRC). Vapor-phase acetonitrile is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the

half-life for this reaction in air is estimated to be 621 days(SRC), calculated from its rate constan t of 2 .63X10-14 cu cm/molecule-sec at 25

deg C(3). Acetonitrile does not undergo direct photolysis in the vapor ph ase(4,5).

[(1) Bidleman TF ; Environ Sci Technol 22 : 361-367 (1988) (2) Boublik T at al ; The vapor pressures of pure

substances . Vol 17 Amsterdam, Netherlands : Elsevier Sci Publ (1984) (3) Atkinson R; J Phys Chem Ref Data .

Monograph 2 (1994) (4) Kagiya T et al ; Japan Chem Soc Spring Term Ann Mtg, Japan : Tokyo, April 1-4, Paper

No . 1036 (1975) (5) Fujiki M at al ; Simulation studies of degradation of chemicals in the environment

Chem Res Report No . 1/1978, Japan : Tokyo, Environ Agency Japan, Off Health Studies (1978)1**PEER

REVIEWED* *

Environmental Biodegradation:

AEROBIC: Enzyme-catalyzed hydrolysis of nitriles, such as acetonitrile, has been shown to proceed by two distinct routes(1,2); a nitril ase

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transforms the nitriles directly into acids plus ammonium ion, or a nitrile hydratase forms the amide which is hydrolyzed to acid plus

ammonium ion by amidase(1,2). A mixed microbial culture isolated from an environment contaminated with organic cyanides and PCBs

utilized acetonitrile as the sole source of carbon and nitrogen(3). The mixed microbial culture was grown for 48 hrs at pH 7 with 1 g/l of

acetonitrile ; the final pH and ammonia concn were determined to be 8 .81 and 80.1 umol/ml, respectively(3). The biodegradation studies of

acetonitrile wi th mixed cultures ofmicroorgan isms from activated sludge and sewage show that degradati on proceeds sluggishly without

acclimati zati on of microorgan isms, particularly at high concn(4,5). Degradati on is faster with acclimatization(6-1 1). With activated sludge

as microbial riod of acetonitrile de was about I day after which -adatQa the compound degraded wi a -Ti e o-f

1 .2 da__ys(8) . Acclimated mixed micro i s isolated by an enric en c ture technique degraded 58% acetonitrile in 5 days(9) . The

biodtg-radability of acetonitrile was also observed with river water; the 12 day ThOD (theoreti cal oxygen dem and) with river water was

~ 40%(10,11). Acclimation of th e microorganisms was examined by redosing; the degradation was 5 times faster after acclimation; it was

also 4 times faster at 20 deg C than at 5 deg C(10,11) . The biodegradation is expected to be much slower in seawater than in freshwater

(12).

[(1) Meth-Cohn 0, Wang MX ; J Chem Soc Perkin Trans 1 : 1099-1104 (1997) (2) Kobayashi M et al ; Biochem

Biophys Res Commun 253 : 662-666 (1998) (3) Chapatwala KD et al ; Environ Toxicol Chem 11 : 1145-51 (1992)

(4) Kalmykova GY, Rogovskaya TI ; Biol Vnutr Vod 38 : 79-83 (1978) (5) Placak OR, Ruchhoft CC ; Sewage Works

J 19 : 423-40 (1946) (6) Ludzack FJ et al ; Sewage Ind Wastes 31 : 33-44 (1959) (7) Thom NS, Agg AR ; Proc R

Soc Lond B189 : 347-57 (1975) (8) Urano K, Kato Z ; J Hazardous Materials 13 : 147-59 (1986) (9) Babeu L,

Vaishnav DD ; J Ind Microbiol 2 : 107-15 (1987) (10) Ludzack FJ et al ; Proc 13th Ind Waste Conf Purdue Univ

Eng Ext Service, p . 297-312 (1958) (11) Ludzack FJ, Ettinger MB ; Water Pollut Control Assoc J 32 : 1173-

2000 (1960) (12) Takemoto S at al ; Suishitsu Odaku Kenkyu 4 : 80-90 (1981)]**PEER REVIEWED* *

ANAEROBIC: Results of anaerobic tests with acetonitrile suggest th at anaerobic biodegradation is not effective for removing the

compound from wastewater(1).

[(1) Ludzack FJ et al ; J Water Pollut Control Fed 33 : 492-505 (1961)]**PEER REVIEWED**

Environmental Abiotic Degradation :

The photochemical smog studies show that this compound is unreacti ve towards photochemically-generated free radicals(2). Due to

nonreactivity of acetonitrile in the atmosphere, transport of the compound from troposphere to stratosphere is expected to occur(SRC) and

acetonitrile has been detected in th e stratosphere(1).

[(1) Arijs E at al ; Nature 303 : 314-6 (1983) (2) Dimitriades B, Joshi SB ; pp . 705-11 in Inter Conf

Photochem Oxidant Poll Control, USEPA-600/3-77-001B Research Triangle Park,NC : USEPA (1977)]**PEER

REVIEWED* *

The rate constant for the vapor-phase reaction of acetonitrile with photochemically-produced hydroxyl radicals is 2.63X10-14 cu

cm/molecule-sec at 25 deg C(1) . This corresponds to an atmospheri c half-life of about 621 days at an atmosphe ric concentration of 5X10+5

hydroxyl radicals per cu cm(1) . The reported rate constant for the reac ti on of acetonitrile with hydroxyl radicals in aqueous solution at pH

9 is in th e ran ge 2 .1-3 .5X10+6/M-sec(2,3). Assuming the concentrati on of hydroxyl radicals in natural surface waters as 1X10-17 M, the

half-life is >600 yrs(SRC). The chemical hydrolysis of acetonitrile in water is base catalyzed(4) ; th e rate constant for base catalyzed

hydrolysis is 5 .8X10-3/M-hr and half-life at pH 7 is more than 150,000 yrs(4). Acetonitrile absorbs light only in the far UV region(S).

Therefore, photolysis of the compound in the atmosphere should not be an important process(SRC).

[(1) Atkinson R; J Phys Chem Ref Data . Monograph 2 (1994) (2) Anbar M, Neta P ; Inter J Appl Radiation

Isotopes 18 : 493-523 (1967) (3) Dorfman LM, Adams GE ; Reactivity of the hydroxyl radical in aqueous

solution NDRD-NBS-46 Washington, DC : Natl Bur Stand (NTIS COM-73-50623) (1973) (4) Ellington JJ at al ;

Measurement of hydrolysis rate constants for evaluation of hazardous waste land disposal . USEPA-600/S3-

88/028 (PB88-234 042/AS) (1988) (5) Arijs E et al ; Nature 303 : 314-6 (1983)3**PEER REVIEWED**

Environmental Bioconcentration :

An estimated BCF of 3 was calculated for acetonitrile(SRC), using a log Kow of -0 .34(1) and a regression-derived equation(2). According

to a classification scheme(3), th is BCF suggests the potential for bioconcentrati on in aquatic organisms is low(SRC).

[(1) Hansch C et al ; Exploring QSAR . Hydrophobic, Electronic, and Steric Constants . ACS Prof Ref Book .

Heller SR, consult . ed ., Washington, DC : Amer Chem Soc p . 4 (1995) (2) Meylan WM et al ; Environ Toxicol

Chem 18 : 664-72 (1999) (3) Franke C at al ; Chemosphere 29 : 1501-14 (1994)]**PEER REVIEWED* *

Soil Adsorption/Mobility:

The Koc of acetonitrile is estimated as 16(SRC), using a measured log Kow of -0.34(1) and a reg re ssion-de rived equation(2). According to

a classification scheme(3), this estimated Koc value suggests th at acetonitrile is expected to have very high mobility in soil(SRC) .

[(1) Hansch C at al ; Exploring QSAR . Hydrophobic, Electronic, and Steric Constants . ACS Prof Ref Book .

Heller SR, consult . ed ., Washington, DC : Amer Chem Soc p . 4 (1995) (2) Lyman WJ et al ; Handbook of

Chemical Property Estimation Methods . Washington, DC : Amer Chem Soc pp . 4-9 (1990) (3) Swann RL et al ;

Res Rev 85 : 17-28 (1983)]**PEER REVIEWED* *

Volatilization from Water/Soil:

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The Henry's Law constant for acetonitrile is estimated as 3.45X10-5 atm-cu m/mole(1). This Henry's Law constant indicates that

acetonitrile is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model

river ( 1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 12 hours(SRC). The volatilization half-life from a model lake

(1 m deep, flowing 0 .05 m/sec, wind velocity of 0 .5 m/sec)(2) is estimated as 7 days(SRC). Acetonitrile's Henry's Law constant(l)

indicates that volatilization from moist soil surfaces may occur(SRC). The potential for volatilization of acetonitrile from dry soil surfaces

may exist(SRC) based upon a vapor pressure of 88.8 mm Hg(3).

[(1) Gaffney JS et al ; Environ Sci Technol 21 : 519-23 (1987) (2) Lyman WJ et al ; Handbook of Chemical

Property Estimation Methods . Washington, DC : Amer Chem Soc pp . 15-1 to 15-29 (1990) (3) Boublik T et al ;

The vapor pressures of pure substances . Vol 17 . Amsterdam, Netherlands : Elsevier Sci Publ (1984)]**,PEER

REVIEWED* *

Effluent Concentrations:

Acetonitrile was qualitatively detected in shale oil wastewater(l) and wastewater from coal gasificati on process(2,3). During the early

1980s, EPA conducted performance testing of eight full-scale hazardous waste incinerators ; in this study, the reasonable worst case

hazardous stack emissions of acetonitrile was 0.3 ng/l(4). The concn of acetonitrile in the emissions from a municipal waste incineration

plant in Germany were 13 .7 ug/cu m(5). The concn of acetonitrile in condensate and process retort water from an oil-shale processing

facility in Colorado was 38 .9 and 5 .8 mg/l, respectively(6).

[(1) Hawthorne SB, Sievers RE ; Environ Sci Technol 18 : 483-90 (1984) (2) Pellizzari ED et al ;

Identification of organic components in aqueous effluents from energy-related processes . ASTM Spec Tech

Publ STP 686 : 256-74 (1979) (3) Mohr DH, King CJ ; Environ Sci Technol 19 : 929-35 (1985) (4) Dempsey CR ; J

Air Waste Manage Assoc 43 : 1374-79 (1993) (5) Jay K et al ; Chemosphere 30 : 1249-60 (1995) (6) Leenheer JA

et al ; Environ Sci Technol 16 : 714-23 (1982)]**PEER REVIEWED* *

Atmosphe ri c Concentrations:

URBAN/SUBURBAN: Acetonitrile was not detected in the 1 sample taken from an urb an area(1). It was detected in air near ground levels

in both urban and rural are as at concn 2-7 ppb(2). The avg concn of acetonitrile in stratosphere air above Deuselbach, Germany ranged

from 117 to 212 parts per trillion between the years 1986-1987(3). Acetonitri0e was detected with a frequency of 20% in exhaled air of

normal human (non-smoking) at a me an concn 7.4 ng/1(4,5).

[(1) Shah JJ, Heyerdahl EK ; National ambient volatile organic compounds (VOCs) data base update . Res Tri

Park, NC : Atmos Sci Res Lab USEPA-600/3-88/010a (1988) (2) Becker KM, Ionescu A; Geophys Res Lett 9 :

1349-51 (1982) (3) Hamm S et al ; Geophysical Res Lett . 16 : 483-86 (1989) (4) Krotoszyniski BK et al ; J

Anal Toxicol 3 : 225-34 (1979) (5) Krotoszyniski BK at al ; J Chromatog Sci 15 : 239-44 (1977)]**PEER

REVIEWED* *

RURAL/REMOTE : Acetonitrile was detected at a me an concn of 0 .024 ppb in two samples from a rural area(1). It was detected in air near

ground levels in both urban and rural areas at concn 2-7 ppb(2). It was reported to be present in the upper stratosphere(3).

[(1) Shah JJ, Heyerdahl EK ; National ambient volatile organic compounds (VOCS) data base update USEPA600/3-88/010(a) Res Tri Park, NC : Atmos Sci Res Lab USEPA (1988) (2) Becker KM, Ionescu A; Geophys Res

Lett 9 : 1349-51 (1982) (3) Arijs E at al ; Nature 303 : 314-6 (1983)]**PEER REVIEWED* *

Food Survey Values:

Acetonitrile was detected in some milk products, such as kefir culture(l).

[(1) Palo V, Ilkova H ; J Chromatog 53 : 363-7 (1970) 1 **PEER REVIEWED**

Other Environmental Concentrations :

. . . A standardized second puff of cigarette smoke contains 0 .31 mg acetonitrile .

[USEPA; Chemical Hazard Information Profiles p .9 EPA-560/11-80-011 (1980)1**PEER REVIEWED* *

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