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SECTION 1. CHEMICAL IDENTIFICATION

CHEMINFO Record Number: 573
CCOHS Chemical Name: Ethyl acetoacetate

Synonyms:
Acetoacetic acid, ethyl ester
Acetoacetic ester
Active acetyl acetate
Diacetic ester
Ethyl acetylacetate
Ethyl acetylacetonate
Ethyl 3-oxobutanoate
Ethyl 3-oxobutyrate
3-Oxobutanoic acid ethyl ester
EAA
Diacetic ether
1-Ethoxybutane-1,3-dione

Chemical Name French: Acétoacétate d'éthyle
Chemical Name Spanish: Acetoacetato de etilo
CAS Registry Number: 141-97-9
RTECS Number(s): AK5250000
EU EINECS/ELINCS Number: 205-516-1
Chemical Family: Aliphatic carboxylic acid ester / aliphatic keto carboxylic acid ester / aliphatic saturated keto carboxylic acid ester / alkyl acetoalkanoate / acetoacetic acid ester / acetoacetate / ethyl ester
Molecular Formula: C6-H10-O3
Structural Formula: CH3-C(=O)-CH2-C(=O)-O-CH2-CH3

SECTION 2. DESCRIPTION

Appearance and Odour:
Colourless liquid with a fruity or rum odour.(1,8)

Odour Threshold:
Not available

Warning Properties:
Insufficient information for evaluation.

Composition/Purity:
Ethyl acetoacetate is available in grades with purity of 98-99.5%.(5)

Uses and Occurrences:
Ethyl acetoacetate (EAA) is used as a chemical intermediate for antimalarial agents, Vitamin B1, analgesics, antibiotics, antipyrene and aminopyrene and plant protection agents; in the manufacture of dyes, yellow paint pigments, lacquers, inks and plastics; in the synthesis of amino acids; as a solvent; as a food flavouring agent; and in perfumes and aromas.(1,3,6,8)


SECTION 3. HAZARDS IDENTIFICATION

EMERGENCY OVERVIEW:
Colourless liquid with a fruity or rum odour. COMBUSTIBLE LIQUID AND VAPOUR. Can form explosive mixtures with air at, or above 57 deg C (135 deg F). EYE IRRITANT. Causes severe eye irritation.



POTENTIAL HEALTH EFFECTS

Effects of Short-Term (Acute) Exposure

Inhalation:
Ethyl acetoacetate can form a vapour at room temperatures. However, it is not expected to produce significant harmful effects by this route of exposure, based on the limited animal information available. There is no human information available.

Skin Contact:
Ethyl acetoacetate is not irritating or a mild irritant, based on limited human and animal information. Application of 8% ethyl acetoacetate in petroleum jelly to the skin of 26 people in a 48-hour patch test resulted in no irritating effects. (3, unconfirmed).
It is not expected to produce harmful effects if absorbed through the skin, based on animal toxicity values.

Eye Contact:
Ethyl acetoacetate is a severe eye irritant, based on animal information. There is no human information available.

Ingestion:
Ethyl acetoacetate is not expected to be toxic if ingested, based on animal information. There is no human information available. Ingestion is not a typical route for occupational exposure.

Effects of Long-Term (Chronic) Exposure

Skin Sensitization:
Ethyl acetoacetate did not induce skin sensitization in humans in one test.(3, unconfirmed)

There is no other human or animal information available.

Carcinogenicity:

There is no human or animal information available.

The International Agency for Research on Cancer (IARC) has not evaluated the carcinogenicity of this chemical.

The American Conference of Governmental Industrial Hygienists (ACGIH) has no listing for this chemical.

The US National Toxicology Program (NTP) has not listed this chemical in its report on carcinogens.

Teratogenicity and Embryotoxicity:
There is no human or animal information available.

Reproductive Toxicity:
There is no human or animal information available.

Mutagenicity:
There is no human or animal information available. Positive and negative results have been reported for ethyl acetoacetate in mutagenicity tests using bacteria and negative results have been reported in a test using cultured mammalian cells.

Toxicologically Synergistic Materials:
There is no information available.

Potential for Accumulation:
Probably does not accumulate. It is believed to hydrolyze and metabolize readily in the body.(8)


SECTION 4. FIRST AID MEASURES

Inhalation:
If symptoms are experienced, remove source of contamination or move victim to fresh air. Obtain medical advice immediately.

Skin Contact:
As quickly as possible, flush with lukewarm, gently flowing water for at least 5 minutes or until the chemical is removed. Under running water, remove contaminated clothing, shoes and leather goods (e.g. watchbands, belts). Obtain medical advice immediately. Completely decontaminate clothing, shoes and leather goods before re-use or discard.

Eye Contact:
Immediately flush the contaminated eye(s) with lukewarm, gently flowing water for 20 minutes or until the chemical is removed, while holding the eyelid(s) open. Take care not to rinse contaminated water into the unaffected eye or onto the face. Obtain medical attention immediately.

Ingestion:
NEVER give anything by mouth if victim is rapidly losing consciousness, is unconscious or convulsing. Have victim rinse mouth thoroughly with water. DO NOT INDUCE VOMITING. Have victim drink 240 to 300 mL (8 to 10 oz) of water to dilute material in stomach. Obtain medical advice immediately.

First Aid Comments:
Provide general supportive measures (comfort, warmth, rest).
Consult a doctor and/or the nearest Poison Control Centre for all exposures except minor instances of inhalation or skin contact.
All first aid procedures should be periodically reviewed by a doctor familiar with the material and its conditions of use in the workplace.



SECTION 5. FIRE FIGHTING MEASURES

Flash Point:
57 deg C (135 deg F) (closed cup) (7)

Lower Flammable (Explosive) Limit (LFL/LEL):
1.4% at 93 deg C (200 deg F) (7)

Upper Flammable (Explosive) Limit (UFL/UEL):
9.5% at 176 deg C (350 deg F) (7)

Autoignition (Ignition) Temperature:
295 deg C (563 deg F) (7)

Sensitivity to Mechanical Impact:
Probably not sensitive. Stable material.

Sensitivity to Static Charge:
Ethyl acetoacetate will not accumulate static charge, since it has a high electrical conductivity.(7,12) Mixtures of ethyl acetoacetate vapour and air at concentrations in the flammable range will not be ignited by a static discharge, since it has a moderately high flash point.

Electrical Conductivity:
4 X 10(6) pS/m at 25 deg C (7,12)

Minimum Ignition Energy:
Not available.

Combustion and Thermal Decomposition Products:
Carbon monoxide and carbon dioxide. Incomplete combustion may produce irritating fumes and acrid smoke.

Fire Hazard Summary:
COMBUSTIBLE LIQUID. Can form explosive mixtures with air at, or above 57 deg C (135 deg F). During a fire, irritating/toxic smoke and fumes may be generated. Closed containers may rupture violently and suddenly release large amounts of product when exposed to fire or excessive heat for a sufficient period of time.

Extinguishing Media:
Carbon dioxide, dry chemical powder, appropriate foam, water spray or fog.(5) Special alcohol resistant "multipurpose" fire-fighting foams are recommended for use with any flammable liquid that is soluble in water, such as ethyl acetoacetate.(7) Foam manufacturers should be consulted for recommendations regarding types of foams and application rates.

Fire Fighting Instructions:
Evacuate area and fight fire from a safe distance or protected location. Approach fire from upwind to avoid toxic decomposition products.
Closed containers may rupture violently when exposed to the heat of fire and suddenly release large amounts of products. Stay away from ends of tanks, but be aware that flying material (shrapnel) from ruptured tanks may travel in any direction.
If possible, isolate materials not yet involved in the fire and move containers from fire area if this can be done without risk. Protect personnel. Otherwise, cool fire-exposed containers, tanks or equipment by applying hose streams. Cooling should begin as soon as possible (within several minutes) and should concentrate on any unwetted portions of the container. Apply water from the side and a safe distance. Cooling should continue until well after the fire is out. If this is not possible, use unmanned monitor nozzles and immediately evacuate the area.
If a leak or spill has not ignited, use water spray in large quantities to disperse the vapours and to protect personnel attempting to stop a leak. Water spray can be used to dilute spills to nonflammable mixtures and to flush spills away from ignition sources. Solid streams of water may be ineffective and spread material.
For an advanced or massive fire in a large area, use unmanned hose holders or monitor nozzles; if this is not possible withdraw from fire area and allow the fire to burn. Withdraw immediately in case of rising sound from venting safety device or any discolouration of tank.

Protection of Fire Fighters:
Ethyl acetoacetate is slightly hazardous to health. Firefighters may enter the area if positive pressure self-contained breathing apparatus (NIOSH approved or equivalent) and full Bunker Gear is worn.



NATIONAL FIRE PROTECTION ASSOCIATION (NFPA) HAZARD IDENTIFICATION

NFPA - Health: 1 - Exposure would cause significant irritation, but only minor residual injury.
NFPA - Flammability: 2 - Must be moderately heated or exposed to relatively high ambient temperatures before ignition can occur.
NFPA - Instability: 0 - Normally stable, even under fire conditions, and not reactive with water.

SECTION 9. PHYSICAL AND CHEMICAL PROPERTIES

Molecular Weight: 130.14

Conversion Factor:
1 ppm = 5.31 mg/m3; 1 mg/m3 = 0.19 ppm at 25 deg C (calculated)

Physical State: Liquid
Melting Point: -45 deg C (-49 deg F) (13,14,15)
Boiling Point: 180-181 deg C (356-357.8 deg F) (13,15,16)
Relative Density (Specific Gravity): 1.025 at 20 deg C (16,17); 1.021 at 25 deg C (14,15) (water = 1)
Solubility in Water: Soluble (11 g/100 mL at 17 deg C) (1,18)
Solubility in Other Liquids: Soluble in all proportions in ethanol, acetone and diethyl ether; soluble in benzene and chloroform.(1,13)
Coefficient of Oil/Water Distribution (Partition Coefficient): Log P(oct) = 0.25 (experimental) (19)
pH Value: Not available.
Dissociation Constant: pKa = 10.68 at 25 deg C (14)
Viscosity-Dynamic: 1.419 mPa.s (1.419 centipoises) at 20 deg C; 1.508 mPa.s (1.508 centipoises) at 25 deg C (14)
Viscosity-Kinematic: 1.38 mm2/s (1.38 centistokes) at 20 deg C; 1.48 mm2/s (1.48 centistokes) at 25 deg C (calculated)
Saybolt Universal Viscosity: Approximately 30.5 Saybolt Universal Seconds at 37.8 deg C (100 deg F) (calculated)
Surface Tension: 32.39 mN/m (32.39 dynes/cm) at 20 deg C; 31.88 mN/m (31.88 dynes/cm) at 25 deg C (calculated) (14,20)
Vapour Density: 4.48 (air = 1) (1,17)
Vapour Pressure: 0.104 kPa (0.78 mm Hg) at 25 deg C (1,18)
Saturation Vapour Concentration: Approximately 1000 ppm (0.10%) at 25 deg C (calculated)
Evaporation Rate: Extremely low.(21)
Henry's Law Constant: 1.22 X 10(-1) Pa.m3/mole (cited as 1.2 X 10(-6) atm.m3/mole) at 25 deg C (18); log H = -4.31 (dimensionless constant; calculated)

SECTION 10. STABILITY AND REACTIVITY

Stability:
Normally stable. May slowly hydrolyze to ethanol and acetic acid in the presence of water.

Hazardous Polymerization:
Does not occur

Incompatibility - Materials to Avoid:

NOTE: Chemical reactions that could result in a hazardous situation (e.g. generation of flammable or toxic chemicals, fire or detonation) are listed here. Many of these reactions can be done safely if specific control measures (e.g. cooling of the reaction) are in place. Although not intended to be complete, an overview of important reactions involving common chemicals is provided to assist in the development of safe work practices.


STRONG OXIDIZING AGENTS (e.g. nitrates, perchlorates, peroxides) - reaction can be violent. Increased risk of fire and explosion.(5,22)
STRONG ACIDS (e.g. sulfuric acid or hydrochloric acid) or STRONG BASES (e.g. sodium hydroxide or potassium hydroxide) - decomposition (hydrolysis) can occur, releasing heat. The reaction may be vigorous and there is a risk of fire and explosion.(5)
REDUCING AGENTS (e.g. hydrides, such as lithium aluminum hydride) - reaction may be strongly exothermic (generation of heat). Increased risk of fire and explosion.(5)
TRIBROMONEOPENTYL ALCOHOL AND ZINC - violent decomposition can occur.(7,23)

Hazardous Decomposition Products:
Acetic acid

Conditions to Avoid:
Open flames, sparks, heat and other ignition sources.

Corrosivity to Metals:
Ethyl acetoacetate is not corrosive to the common metals, such as cast iron, carbon steel, stainless steel (types 304 and 316), aluminum, copper and its alloys, nickel alloys, tantalum and titanium.(24,25)

Corrosivity to Non-Metals:
Ethyl acetoacetate attacks plastics, such as acrylonitrile-butadiene-styrene (ABS), polypropylene and polyvinyl chloride (PVC); and elastomers, such as chloroprene, fluorosilicone, neoprene, nitrile buna-N (NBR), polyurethane and Viton A. It does not attack plastics, such as chlorinated polyvinyl chloride (CPVC) and Teflon; and elastomers, such as butyl rubber, natural rubber, ethylene-propylene-diene and isoprene.(24,26)


SECTION 11. TOXICOLOGICAL INFORMATION

LC50 (rat): greater than 1380 ppm (4-hour exposure); cited as greater than 1129 ppm (6-hour exposure) (essentially saturation vapour concentration) (3, unconfirmed)

LD50 (oral, rat): 3980 mg/kg (cited as 3.98 gm/kg) (2)
LD50 (oral, mouse): 3200 to 6400 mg/kg (3, unconfirmed)

LD50 (dermal, rabbit): greater than 10300 mg/kg (cited as 10 mL/kg) (2)

Eye Irritation:

Ethyl acetoacetate is a severe eye irritant.

Application of 0.1 mL of undiluted ethyl acetoacetate caused severe injury in rabbits (scored over 5 where 5 is severe injury; graded 4/10).(9)

Skin Irritation:

Ethyl acetoacetate is not irritating or a mild irritant based on limited information.

Application of 510 mg of ethyl acetoacetate onto the skin of rabbits caused a mild reaction.(4, unconfirmed) Ethyl acetoacetate is a non-irritant or mild irritant to the skin.(3, unconfirmed)

Effects of Short-Term (Acute) Exposure:

Inhalation:
An 8-hour exposure to the concentrated vapour of ethyl acetoacetate was not lethal to rats.(2)

Ingestion:
Ingestion of 0, 100, 300 or 1000 mg/kg/day ethyl acetoacetate for 28 days did not adversely affect the health or body weight of rats. Only slight alterations were observed upon analysis of the blood, serum, and urine as well as histopathological evaluation of the treated animals. Treatment with ethyl acetoacetate at these doses is considered not to have adverse effects.(10)

Skin Sensitization:
Ethyl acetoacetate did not induce skin sensitization in guinea pigs.(3, unconfirmed)

Mutagenicity:
There is insufficient information available to evaluate the mutagenic potential of ethyl acetoacetate.
Negative results (chromosome aberrations) were reported for a test using cultured mammalian cells.(3, unconfirmed) Positive results (DNA damage, gene mutation) were obtained in bacteria.(11) Details of this study are not available in English. Negative results (gene mutation) were reported for another test using bacteria.(3, unconfirmed)


SECTION 16. OTHER INFORMATION

Selected Bibliography:
(1) US National Library of Medicine. Ethyl acetoacetate. Last revision date: 2002-02-13. In: Hazardous Substances Data Bank (HSDB). CHEMpendium. [CD-ROM]. Canadian Centre for Occupational Health and Safety (CCOHS). Issue: 2002-3. Also available at: <ccinfoweb.ccohs.ca/chempendium/search.html>
(2) Smyth, Jr., H.F., et al. Further experience with the range finding test in the industrial toxicology laboratory. Journal of Industrial Hygiene and Toxicology. Vol. 30, no. 1 (Jan. 1948). p. 63-68
(3) Gesellschaft Deutscher Chemiker (GDCh). Advisory Committee on Existing Chemicals of Environmental Relevance (BUA). Criteria document on ethyl acetoacetate. BUA Report 169 (June, 1995). S. Hirzel Wissenschaftliche Verlagsgesellschaft, 1997. [English Translation, 1997]
(4) National Institute for Occupational Safety and Health (NIOSH). Ethyl acetoacetate. Last updated: 97-01. In: Registry of Toxic Effects of Chemical Substances (RTECS(R)). [CD-ROM]. Canadian Centre for Occupational Health and Safety (CCOHS). Also available at: <ccinfoweb.ccohs.ca/rtecs/search.html>
(5) Ethyl acetoacetate, 99%+, FCC. Sigma-Aldrich Website. Sigma-Aldrich Corporation. MSDS. Date updated: 2003-01. Available at: <www.sigmaaldrich.com/suite7/homepage/New_Site_Redirect.html> (Password required)
(6) Abaecherli, C., et al. Ketenes: acetoacetate derivatives. In: Kirk-Othmer encyclopedia of chemical technology. 4th ed. Vol. 14. John Wiley and Sons, 1995. p. 970-978
(7) Fire protection guide to hazardous materials. 13th ed. Edited by A.B. Spencer, et al. National Fire Protection Association, 2002. NFPA 325; NFPA 491
(8) Bisesi, M. Esters of mono- and alkenyl carboxylic acids and mono- and polyalcohols: ethyl acetoacetate. In: Patty's toxicology. 5th ed. Edited by E. Bingham, et al. Vol. 6. John Wiley and Sons, 2001. p. 584-586
(9) Carpenter, C.P., et al. Chemical burns of the rabbit cornea. American Journal of Ophthalmology. Vol. 29 (1946). p. 1363-1372
(10) Cook, W.M. et al. A 28-day feeding study with ethyl acetoacetate in rats. Food and Chemical Toxicology. Vol. 30, no. 7 (July 1992). p. 567-573
(11) Yoo, Y.S. Mutagenic and antimutagenic activities of flavoring agents used in foodstuffs. The Journal of the Osaka City Medical Center. Vol. 34 (1986). p. 267-288
(12) Britton, L.G. Using material data in static hazard assessment. Plant/Operations Progress. Vol. 11, no. 2 (Apr.
1992). p. 56-70
(13) Lide, D.R., ed. Handbook of chemistry and physics. [CD-ROM]. Chapman and Hall/CRCnetBASE 1999
(14) Dean, J.A. Lange's handbook of chemistry. 14th ed. McGraw-Hill, Inc., 1992. p. 1.213, 5.96, 8.46
(15) Ethyl acetoacetate. The Merck index: an encyclopedia of chemicals, drugs and biologicals. Edited by M.J. O'Neil, et al. 13th ed. Merck and Company, 2001. p. 670
(16) Lewis, Sr., R.J., ed. Ethyl acetacetate. Hawley's condensed chemical dictionary. [CD-ROM]. 14th ed. John Wiley and Sons, Inc., 2002
(17) Sullivan, D.A. Solvents, industrial. In: Kirk-Othmer encyclopedia of chemical technology. 4th ed. Vol. 22. John Wiley and Sons, 1997. p. 542-543, 565
(18) Syracuse Research Corporation. The Physical Properties Database (PHYSPROP). Interactive PhysProp Database Demo. Date unknown. Available at: <www.syrres.com/esc/physdemo.htm>
(19) Syracuse Research Corporation. Interactive LogKow (KowWin) Database Demo. Date unknown. Available at: <syrres.com/esc/kowdemo.htm>
(20) Jasper, J.J. Surface tension of pure liquid compounds. In: Compilation of data of some 2200 pure liquid compounds. Journal of Physical and Chemical Reference Data. Vol. 1, no. 4 (1972). p. 854, 964
(21) Riemenschneider, W. Esters, organic. In: Ullmann's encyclopedia of industrial chemistry. 5th completely revised ed. Vol. A 9. VCH Verlagsgesellschaft, 1987. p. 568, 580
(22) Ethyl acetoacetate. In: Chemical safety sheets: working safely with hazardous chemicals. Kluwer Academic Publishers, 1991. p. 385
(23) Urben, P.G., ed. Bretherick's reactive chemical hazards database. [CD-ROM]. 6th ed. Version 3.0. Butterworth-Heinemann Ltd., 1999
(24) Schweitzer, P.A. Corrosion resistance tables: metals, nonmetals, coatings, mortars, plastics, elastomers and linings, and fabrics. 4th ed. Part B, E-O. Marcel Dekker, Inc., 1995. p. 1137-1140
(25) Corrosion data survey: metals section. 6th ed. National Association of Corrosion Engineers, 1985. p. 54-5 to 55-5
(26) Pruett, K.M. Chemical resistance guide for elastomers II: a guide to chemical resistance of rubber and elastomeric compounds. Compass Publications, 1994. p. C-140 to C-145
(27) Occupational Safety and Health Administration (OSHA). Organic Vapours. In: OSHA Analytical Methods Manual. Revision Date: Oct. 31, 2001. Available at: <www.osha-slc.gov/dts/sltc/methods/toc>
(28) European Union Risk Assessment Report. Ethyl acetoacetate. Risk assessment final report. Vol. 13. European Commission Joint Research Centre. 2002. Available at: <ecb.jrc.it/esis/esis.php>

Information on chemicals reviewed in the CHEMINFO database is drawn from a number of publicly available sources. A list of general references used to compile CHEMINFO records is available in the database Help.


Review/Preparation Date: 2005-01-06

Revision Indicators:
Bibliography 2005-12-06



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