Ethyl Acrylate

HCID 8821CAS 140-88-5

기본 정보

표준 SMILES
C=CC(=O)OCC
InChIKey
JIGUQPWFLRLWPJ-UHFFFAOYSA-N
분자식
C5H8O2
평균 분자량
100.12 g/mol
단동위원소 질량
100.0524295

개요

Ethyl Acrylate can cause cancer according to an independent committee of scientific and health experts.

이름 및 식별자

우선 이름
Ethyl Acrylate
IUPAC
ethyl prop-2-enoate
영어명
Ethyl acrylate
분자식
C5H8O2
분자량
100.12

이름 및 동의어

ETHYL ACRYLATE140-88-5Acrylic acid ethyl esterEthyl propenoate2-Propenoic acid, ethyl esterEthyl 2-propenoateEthylacrylaatEthylakrylatEtil acrilatoAcrylic acid, ethyl esterAethylacrylatEtilacrilatului
이름 더 보기
Akrylanem etyluCarboset 511EthoxycarbonylethyleneEthyl acrylate, inhibitedAcrylate d'ethyle2-Propenoic Acid Ethyl EsterAcrylsaeureaethylesterRCRA waste number U113

데이터베이스 식별자

CAS
140-88-5、87605-70-7、9003-32-1
PubChem CID
8821
DTXSID
DTXSID4020583
ChEMBL
CHEMBL52084
ChEBI
CHEBI:82327
UNII
71E6178C9T
EC Number
205-438-8
Nikkaji
J2.534H

물성

구조 계산 물성

XLogP
1.3
극성 표면적
26.3 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
2
회전 가능 결합 수
3
무거운 원자 수
7

실험 및 물리화학적 성질

Chemical Classes · 2건

Hazardous Air Pollutants (HAPs)

Carcinogens

LipidsFatty Acyls [FA] -> Fatty esters [FA07] -> Short fatty esters [FA0710]
PolymersPlastics & Rubber -> (Meth)acrylates
CosmeticsCosmetics ingredient -> Anticaking/Absorbents; Other (Specify)
SpringerMaterials PropertiesBoiling point
FragrancesFragrance substance (Ethyl acrylate) -> IFRA amendment 40

물리화학적 성질

녹는점
-71.2 °C · -71.2 °C
끓는 점
99.4 °C · 99.4 °C
밀도
0.9234 g/cm3 · 0.9234 g/cm3

안전 및 규제

GHS 분류

GHS Classification · 6건

Danger

H225: Highly Flammable liquid and vapor [Danger Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P270, P271, P272, P280, P301+P317, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P316, P317, P319, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for < 0.1% (2 of 4896) of reports.

Danger

H225 (> 99.9%): Highly Flammable liquid and vapor [Danger Flammable liquids]

유해성 정보

Regulatory Information · 6건

Chemical: 2-Propenoic acid, ethyl ester

Hazard Traits - Carcinogenicity; Hepatotoxicity and Digestive System Toxicity; Neurotoxicity; Respiratory Toxicity

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

2-Propenoic acid, ethyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propenoic acid, ethyl ester are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 11-05-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15431

2-Propenoic acid, ethyl ester: HSNO Approval: HSR001042 Approved with controls

Other Safety InformationIMAP assessments - 2-Propenoic acid, ethyl ester: Human health tier II assessment
DOT LabelFlammable Liquid
Fire Hazards · 3건

Special Hazards of Combustion Products: Toxic and irritating vapors generated when heated.

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.

Highly flammable. Vapour/air mixtures are explosive.

Fire PotentialFlammable liquid. A very dangerous fire hazard when exposed to heat or flame.
Health Hazards · 2건

May cause irritation and burns of eyes and skin. Exposure to excessive vapor concentrations can also cause drowsiness accompanied by nausea, headache, or extreme irritation of the respiratory tract. (USCG, 1999)

· May cause toxic effects if inhaled or absorbed through skin.

안전 및 보호

Fire Fighting · 2건

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious); polymerization hazard]:

Use water spray, powder, alcohol-resistant foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

First Aid Measures · 4건

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Give one or two glasses of water to drink. Do NOT induce vomiting. Refer for medical attention .

Accidental Release Measures · 2건

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

First Aid · 3건

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

General First Aid:

(General first aid procedures)

Safe StorageFireproof. Cool. Keep in the dark. Store only if stabilized.
Firefighting HazardsVapor is heavier than air and may travel a considerable distance to a source of ignition and flash back. Liquid floats on water and may travel to a source of ignition and spread fire. /Ethyl acrylate, inhibited/

독성 정보

Treatment · 1건

For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport. Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal. (A569)

Cancer Sites[in animals: tumors of the forestomach]
Interactions · 1건

Pretreatment of rats with triorthotolyl phosphate potentiated the lethal action of inhaled methyl and ethyl acrylate. Carboxylesterases are important in detoxification of methyl and ethyl acrylate and the exposure to inhibitors of carboxylesterase may potentiate adverse effects of acrylate esters.

Target OrgansEyes, skin, respiratory system
Health EffectsThickened forestomach mucosa, forestomach inflammation and lesions, and abdominal adhesions; swelling of renal tubules and the liver, minor lesions on the liver and lung, and increased kidney weight may result from poisoning (L1242).
Ecotoxicity Values · 3건

LC50; Species: Pimephales promelas (Fathead minnow, age 32 days, length 18.7 mm, weight 0.095 g); Conditions: freshwater, flow through, 25.3 °C, pH 7.5, hardness 46.9 mg/L CaCO3, alkalinity 39.7 mg/L CaCO3, dissolved oxygen 6.8 mg/L; Concentration: 2500 ug/L for 96 hr (95% confidence interval: 2310-2700 ug/L) /99% purity/

Bacteria: Pseudomonas putida: inhibition of cell multiplication starts at 270 mg/L

Algae: Microcystis aeruginosa: inhibition of cell multiplication starts at 14 mg/L

규제 정보

FDA Requirements · 2건

Ethyl acrylate is a food additive permitted for direct addition to food for human consumption in accordance with the following conditions: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and b) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part.

Homopolymers and copolymers of ethyl acrylate are an indirect food additive for use only as a component of adhesives.

RCRA Requirements · 1건

U113; As stipulated in 40 CFR 261.33, when ethyl acrylate, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

TSCA Requirements · 1건

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Ethyl acrylate is included on this list. Effective date 4/13/89; Sunset date: 6/30/98.

FIFRA Requirements · 1건

Residues resulting from the use of the following substances, that meet the definition of a polymer and the criteria specified for defining a low-risk polymer in 40 CFR 723.250, as an inert ingredient in a pesticide chemical formulation, including antimicrobial pesticide chemical formulations, are exempted from the requirement of a tolerance under FFDCA section 408, if such use is in accordance with good agricultural or manufacturing practices. Ethyl acrylate is included on this list.

Atmospheric Standards · 1건

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Ethyl acrylate is produced, as an intermediate or a final product, by process units covered under this subpart.

CERCLA Reportable Quantities · 1건

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 1000 lb or 454 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV.D.3.b).

안전 데이터

신호 어
Danger
유해·위험 문구
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드 H225

화학 및 산업

약리 정보

Mechanism of Action · 3건

Cytotoxicity is primarily limited to the olfactory epithelium of the dorsal meatus region of the nasal cavity of rodents following inhalation exposure to acrylic monomers. To investigate the biochemical basis for this effect, three regions of the Fischer F344N rat nasal cavity were evaluated for carboxylesterase activity for ... ethyl acrylate. ... No regional difference in carboxylesterase activity was observed between sensitive and non-sensitive regions of olfactory epithelium. Respiratory epithelium (resistant to cytotoxicity) was found to be have a much lower rate of carboxylesterase activity than olfactory epithelium. These results suggest that the regional distribution of cytotoxicity observed in the rat nasal cavity at high concentrations of inhaled acrylic monomers may be due in part to the amount of released organic acid following deposition. However, the observation of the same esterase activity in sensitive and nonsensitive olfactory regions suggests that nasal air flow patterns and regional deposition may also be critical factors.

Quantitative hemolysis assays of acrylate and methacrylate esters provided estimates of the intrinsic hemolytic activity (Hi, the slope of the concentration-response curve) and the concentrations effecting 5% (H5) and 50% (H50) hemolysis. The dependence of hemolytic activity and LD50 (mice) on physical properties (lipophilicity, molar refraction, and molecular volume of the esters was detected by multiple regression analysis. The observed correlations were: Hi, R2 = 0.94; H5, R2 = 0.95; H50, R2 = 0.94; and LD50, R2 (all compounds) = 0.80, R2 (all compounds less the methyl esters) = 0.94. The difference of the methyl esters was associated with the smaller steric volume of the methyl ester substituent and the presence (methacrylates) or absence (acrylates) of the branched methyl group. Associative steric contributions of the branched methyl group and the ester substituents were probably responsible for greater variability in the methyacrylate series ... /It was concluded that/ the mechanism of the action of the esters is membrane-mediated and relatively nonspecific and that in vivo biotransformation was not a significant factor. Also, long-term toxic liability of the esters may be more closely related to intrinsic toxicity than acute toxicity.

Over the past several years, /the authors/ have been evaluating the mutagenicity and clastogenicity of compounds capable of Michael-type reactions. These compounds, including acrylamide, several acrylate and methacrylate esters, vinyl sulfones, and phorone, have been evaluated using TK+/- -3.7.2C mouse lymphoma cells. Mutagenic chemicals induced increases in the number of small colony tk- deficient mutants. This suggested a clastogenic mechanism which was confirmed by demonstrating increases in aberrations and micronucleus frequencies in cultured cells. Vinyl sulfone was found to be the most effective chemical mutagen with induction of genotoxic effects at concentrations as low as 0.25 microgram/ml. The other compounds also produced positive results, but at higher concentrations. Since these compounds are known to deplete glutathione, phorone, a model glutathione depleter, was examined and found to produce similar effects as the other compounds in mouse lymphoma cells. These results suggest that the direct-acting Michael-type reaction has activity relevant to producing a genotoxic effect. Since acrylamide has been found to be a potent germ cell mutagen, this mechanism may be also relevant in the induction of heritable mutagenic risk.

Metabolism/Metabolites · 6건

Ethyl 2,3-(14)C-acrylate to rats orally by gavage at doses of 2, 20 and 200 mg/kg bw ...The major metabolite was (14)CO2, with 52-61% exhaled within 24 hr ... Three metabolites were identified: 3-hydroxypropionic acid and two mercapturic acids. N-Acetyl-S-(2-carboxyethyl)cysteine arises by glutathione conjugation of acrylic acid, while N-acetyl-S-(2-carboxyethyl)cysteine ethyl ester derives from the conjugation of intact ethyl acrylate. The percentage of the dose excreted as these mercapturic acids falls with increasing dose, consistent with depletion of glutathione. Although ethyl acrylate does not reduce non-protein sulfhydryls in the liver, marked and dose-dependent depletion occurs in the forestomach and glandular stomach, which is enhanced by pretreatment of rats with the esterase inhibitor tri(ortho-cresyl)phosphate. These data are consistent with the hydrolysis of ethyl acrylate being a systemic detoxication reaction, since acrylic acid has no effect on non-protein sulfhydryl levels.

Increases in urinary levels of 3-hydroxypropanoic, lactic and acetic acids /were reported/ after administration of ethyl acrylate to rats.

Ethyl acrylate reacts spontaneously with glutathione and protein sulfhydryl groups in many tissues: in liver alone, conjugation with glutathione was catalysed by cytosolic glutathione S-transferase.

The liver /plays a major role/ in the hydrolysis of ethyl acrylate, the order of activities among tissues being liver >> blood >> lung > kidney. The hydrolysis of ethyl acrylate in various regions of the nose and respiratory tract was region-dependent ... : high activity was found in homogenates of the dorsal meatus and olfactory septum, with much lower activity in respiratory epithelium. This distribution of activity does not correlate well with the distribution of cytotoxicity of ethyl acrylate after inhalation exposure ... Ethyl acrylate was hydrolyzed in homogenates of mouse nasal epithelium.

For more Metabolism/Metabolites (Complete) data for Ethyl acrylate (13 total), please visit the HSDB record page.

Ethyl acrylate is hydrolized to acrylic acid in liver, kidney, and lung homogenates. It is suggested to bind to glutathione spontaneaoulsy and after catalysis by liver glutathione-S-transferase. The major metabolites of ethyl acrylate are mercapturic acids od ethyl acrylate and acrylic acid. Three metabolites were identified in a study: 3-hydroxypropionic acid and two mercapturic acids. N-Acetyl-S-(2-carboxyethyl)cysteine arises by glutathione conjugation of acrylic acid, while N-acetyl-S-(2-carboxyethyl)cysteine ethyl ester derives from the conjugation of intact ethyl acrylate.(A347, A635, A664, ).

MeSH Pharmacological Classification · 2건

Substances that increase the risk of NEOPLASMS in humans or animals. Both genotoxic chemicals, which affect DNA directly, and nongenotoxic chemicals, which induce neoplasms by other mechanism, are included.

Chemical agents that increase the rate of genetic mutation by interfering with the function of nucleic acids. A clastogen is a specific mutagen that causes breaks in chromosomes.

Absorption, Distribution and Excretion · 5건

Ethyl 2,3-(14)C-acrylate /was given/ to rats orally by gavage at doses of 2, 20, and 200 mg/kg bw. The total recovery in specific tissues and excreta fell with increasing dose from 108% at 2 mg/kg bw to 73% at 200 mg/kg bw ... The proportion of radioactivity excreted in the urine fell with increasing dose, from 28% at 2 mg/kg bw to 8% at 200 mg/kg bw.

Inhalation exposure of male Wistar rats to 1000 mg/cu m ethyl acrylate for 6 hr led to a significant increase in urinary thioether excretion

Ethyl acrylate is absorbed through the skin.

Absorption of ethyl acrylate vapors by the isolated upper respiratory tract was compared to the isolated lower respiratory tract and intact animal. 30-70% of ethyl acrylate was absorbed when passed through the upper respiratory tract. Similar levels were absorbed by the isolated lower respiratory tract and intact animal. It was estimated that intact animals received 50% of ethyl acrylate via the upper respiratory tract.

For more Absorption, Distribution and Excretion (Complete) data for Ethyl acrylate (15 total), please visit the HSDB record page.

Cellular LocationsCytoplasm

용도 및 제조

Uses · 6건

Ethyl acrylate is used in the manufacture of water-based latex paints and adhesives, textile and paper coatings, leather finish resins, and in the production of acrylic fibers.

Used to make acrylic resins for fibers, adhesives, binders, surface coatings, textiles, paper, and leather; [ACGIH]

Monomer for acrylic resins

The monomer in the manufacture of water emulsion paint vehicles; the production of emulsion-based polymers used in textile and paper coatings, leather finish resins and adhesives. Imparts flexibility to hard films.

Reported uses

Ethyl acrylate is a major component of straight acrylic emulsion polymers used in latex paints, a major monomer used in straight acrylic emulsion for textile applications, including backcoatings, fabric finishes, pigment binders, dirt release agents, and thickeners. Used to make emulsion polymers for paper coating; as pulp additives in floor polishes and sealants; in shoe polishes; in base coatings and surface impregnation of leather in adhesives, sealants, caulking compound and binders.

ImpuritiesWater: 0.05% by wt (max), acrylic acid: 0.005% by wt (max)
U.S. Exports · 5건

(1972) 9.03 X 10+9 g

(1975) 1.84 X 10+10 g

(1984) 3.97 X 10+10 g

(1987) 5.58X10+6 lb

(1988) 7.22 X 10+6 lb

U.S. Imports · 2건

(1972) Negligible

(1975) 3.50 X 10+9 g

U.S. Production · 6건

2023: 100,000,000 - <500,000,000 lb

(1972) 1.25 X 10+11 g

(1975) 1.09 X 10+11 g

(1983) 1.39 X 10+11 g

Annual production of ethyl acrylate in 1976 was reported to be over 295 million pounds.

For more U.S. Production (Complete) data for Ethyl acrylate (8 total), please visit the HSDB record page.

Consumption Patterns · 4건

(All acrylate esters, of which n-butyl acetate is the largest volume): surface coatings 44%; adhesives/sealants 18%; textiles 15%, plastics additives 9%, paper 5%, other 9% (2000)

(All acrylic esters) 47% for surface coatings; 22% for textiles; 7% for paper; 7% for polishes; 3% for leather; 9% for acrylic fibers; 5% for misc applications (1969)

(All acrylic acid esters) 46% as a monomer for emulsion polymers and solution polymers in latex paints; 26% as a monomer for emulsion polymers in textile applications; 6% as a comonomer for acrylic fibers; 6% as a monomer for emulsion polymers in polishes; 6% as a monomer for emulsion polymers in paper applications; 4% as a monomer for emulsion polymers used in base coatings and surface impregnation of natural leather; 6% in misc applications (1973)

45% for coatings, 16% for textiles & leather finishes, 9% for paper coatings, 8% for adhesives, 6% for polyacrylates, 5% for polishes, 5% for acrylic fibers, 6% other (1983 est) /Acrylates and acrylic acid/

공급사42 곳

北京华美互利生物化工010-56205725 · [email protected]
郑州阿尔法化工有限公司+86-18530059196 · [email protected]
湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
湖北万得化工有限公司15377098680 15377098680 · [email protected]
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]

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