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CAS No.: | 140-88-5 |
---|---|
Name: | Ethyl acrylate |
Article Data: | 212 |
Molecular Structure: | |
Formula: | C5H8O2 |
Molecular Weight: | 100.117 |
Synonyms: | Acrylicacid ethyl ester (6CI,8CI);2-Propenoic acid ethyl ester;Ethyl 2-propenoate;Ethyl acrylic ester;Ethyl propenoate;NSC 8263; |
EINECS: | 205-438-8 |
Density: | 0.913 g/cm3 |
Melting Point: | -71 °C(lit.) |
Boiling Point: | 99.499 °C at 760 mmHg |
Flash Point: | 15.556 °C |
Solubility: | 1.5 g/100 mL (25 °C) in water |
Appearance: | clear colorless liquid |
Hazard Symbols: | F,Xn |
Risk Codes: | 11-20/21/22-36/37/38-43 |
Safety: | 9-16-33-36/37 |
Transport Information: | UN 1917 3/PG 2 |
PSA: | 26.30000 |
LogP: | 0.73550 |
ethyl 3-(trifluoromethanesulfonyl)propionate
A
Langlois reagent
B
ethyl acrylate
Conditions | Yield |
---|---|
With sodium methylate In methanol at 20℃; | A 100% B n/a |
Conditions | Yield |
---|---|
With iron(III) sulfate; sulfuric acid for 3h; Heating; | 98% |
In neat (no solvent) at 80℃; for 2.5h; | 89% |
With sulfuric acid for 12h; Reflux; | 82% |
Conditions | Yield |
---|---|
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; sodium carbonate In dimethyl sulfoxide at 20℃; for 1.5h; Inert atmosphere; Irradiation; | 95% |
With ethanol; sulfuric acid; zinc | |
With ethanol; zinc | |
With diethyl ether; zinc | |
With 2-methoxy-phenylamine In tetrahydrofuran at 20℃; stereospecific reaction; |
Conditions | Yield |
---|---|
With P(MeNCH2CH2)3N In acetonitrile at 25℃; for 0.0833333h; | 92% |
Multi-step reaction with 2 steps 1: 83 percent / dimethylformamide / 1.) 55 deg C, 60 h, 2.) room temperature, 6 h 2: 100 °C View Scheme | |
With indole; dichloro bis(acetonitrile) palladium(II); potassium carbonate; norbornene In N,N-dimethyl acetamide; water Schlenk technique; Inert atmosphere; regioselective reaction; |
Conditions | Yield |
---|---|
With water; cesium nitrate; tungstophosphoric acid; water; mixture of, dried, tabletted at 85.6 - 165℃; under 2250.23 Torr; Product distribution / selectivity; Gas phase; | A 3.5% B 4.3% C 91.8% |
Conditions | Yield |
---|---|
In tetrahydrofuran N2 or Ar atmosphere; refluxing (3 h, ratio Rh-compd. org. compd. 1:10), cooling (room temp.); addn. of EtOH, washing (EtOH and pentane), drying (N2 stream); elem. anal.; | A 90% B 8-15 |
In tetrahydrofuran N2 or Ar atmosphere; stirring (room temp., 24 h, ratio Rh-compd. org. compd. 1:10); addn. of EtOH, slow evapn., washing (EtOH and pentane), drying (N2 stream); elem. anal.; | A 90% B 8-15 |
Conditions | Yield |
---|---|
In benzene Wittig reaction; Reflux; | 87% |
In 1,4-dioxane at 50℃; for 16h; |
Conditions | Yield |
---|---|
With potassium carbonate In water at 30℃; for 0.166667h; | 77% |
With potassium carbonate In 1,4-dioxane at 70℃; for 5h; | 75% |
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran; paraffin oil at 0 - 25℃; Horner-Wadsworth-Emmons Olefination; Inert atmosphere; Stage #2: formaldehyd In tetrahydrofuran; paraffin oil at 0 - 25℃; for 0.166667h; Horner-Wadsworth-Emmons Olefination; Inert atmosphere; | |
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In toluene at 0℃; Horner-Wadsworth-Emmons Olefination; Inert atmosphere; Schlenk technique; Stage #2: formaldehyd at 20℃; Horner-Wadsworth-Emmons Olefination; Inert atmosphere; Schlenk technique; | |
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran at 20 - 40℃; for 1h; Stage #2: formaldehyd In tetrahydrofuran at 40℃; for 5h; |
1-(trimethylsilyl)piperidin-2-one
Ethyl 2-bromopropionate
A
piperidin-2-one
B
trimethylsilyl bromide
D
ethyl acrylate
Conditions | Yield |
---|---|
at 155 - 180℃; for 3h; Yields of byproduct given; | A n/a B n/a C 73% D n/a |
Conditions | Yield |
---|---|
With oxygen; tetraethylammonium perchlorate In N,N-dimethyl-formamide at 20℃; electroreduction at -1.1 V; | A 70% B 20 % Chromat. |
With oxygen In N,N-dimethyl-formamide at 20℃; Product distribution; electrolysis of the oxygen saturated solution at -1,1 V; 0.1 M TEAP; further esters; | A 70% B 20 % Chromat. |
National Toxicology Program Technical Report Series. (Research Triangle Park, NC 27709) No. NTP-TR-259 ,1986. . Reported in EPA TSCA Inventory. Community Right-To-Know List.
OSHA PEL: TWA 5 ppm; STEL 25 ppm (skin)
ACGIH TLV: TWA 5 ppm; STEL 15 ppm; Suspected Human Carcinogen
DFG MAK: 5 ppm (21 mg/m3)
DOT Classification: 3; Label: Flammable Liquid
For occupational chemical analysis use NIOSH: Esters I, 1450.
Ethyl acrylate, also known as 2-Propenoic acid, ethyl ester, is clear, colorless, flammable liquid with a sharp, acrid odor. It is slightly soluble in water, easily soluble in ethanol, ether, and soluble in chloroform. Ethyl acrylate can easily polymerize upon standing and polymerization is accelerated by heat, light, and peroxides. So this chemical is mainly used in the preparation of various polymers. If you don't want it polymerize spontaneously, you must add an inhibitor to prevent it. The odor threshold for ethyl acrylate ranges from 0.001 to 0.005 part per million (ppm) parts of air. So the human nose is easily detecting this odor.
Preparation: Ethyl acrylate can be obtianed by many methods.
1. Currently, the propylene oxidation method is the most used method. First, oxidize propylene to acrolein, and then further oxidize to acrylic acid. Secondly, go through successive esterification by acrylic acid and ethanol in the presence of ion exchange resin catalyst at the boiling temperature to obtain ethyl acrylate. Equation is as follows:
CH2=CH-CH3[O2]→CH2=CHCHO[O2]→CH2=CHCOOH
CH2=CHCOOH+C2H5OH→CH2=CHCOOC2H5
2. Ethyl acrylate can be obtianed by the reaction of 3-hydroxy propionitrile and ethanol in dilute sulfuric acid solution.
3. Ethyl acrylate can be obtianed by ethylene, carbon monoxide and ethanol in the presence of nickel or cobalt catalyst.
4. Ethyl acrylate can be obtianed by esterification of acrylic acid and acetylene in the presence of hydrochloric acid and Ni (CO)4 in ethanol solution.
Uses: Ethyl acrylate is mainly used as comonomer in the production of resin which is widely used in paints, textiles, leather, adhesives and other industries. It is the intermediate in the preparation of ethyl carbamate insecticides Benfuracarb. Ethyl acrylate also can be used as raw material of protective coatings, adhesives and paper impregnant. The polymer can be used as anti-cracking agent of leather. And the copolymer with ethylene is a hot-melt adhesives, with 5% chloroethyl vinyl ether is synthetic rubber with good performance of oil resistance and heat resistant, which can replace nitrile rubber in some cases. What's more, ethyl acrylate is used in preparation of food flavor such as rum, pineapple and fruit cocktail allowed by GB 2760-1996.
Safty: The main safety issue of ethyl acrylate arises from its being flammable and highly reactive. So people should keep it away from sources of ignition. It is harmful by inhalation, in contact with skin and if swallowed. The drowsiness, nausea, headache, convulsions, lethargy, and respiratory and gastrointestinal irritation has been reported to be caused by acute exposure of workers to ethyl acrylate vapors. There is a favorable safety aspect which is ethyl acrylate has good warning properties: the odor threshold is much lower than any level of health concern. In other words, before the concentration reaches a level capable of creating a serious health risk, the bad odor warns people of ethyl acrylate's presence long. If you want to contact this product, you must wear suitable protective clothing and gloves.
Other properties: (1)ACD/LogP: 1.30; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.298; (4)ACD/LogD (pH 7.4): 1.298; (5)ACD/BCF (pH 5.5): 5.705; (6)ACD/BCF (pH 7.4): 5.705; (7)ACD/KOC (pH 5.5): 121.04; (8)ACD/KOC (pH 7.4): 121.04; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 26.3 Å2; (13)Index of Refraction: 1.402; (14)Molar Refractivity: 26.713 cm3; (15)Molar Volume: 109.645 cm3; (16)Polarizability: 10.59×10-24 cm3; (17)Surface Tension: 24.853 dyne/cm; (18)Density: 0.913 g/cm3; (19)Flash Point: 15.556 °C; (20)Enthalpy of Vaporization: 33.885 kJ/mol; (21)Boiling Point: 99.499 °C at 760 mmHg; (22)Vapour Pressure: 38.182 mmHg at 25°C.
Structure Descriptors:
1. Smiles:C(=O)(OCC)C=C
2. InChI:InChI=1/C5H8O2/c1-3-5(6)7-4-2/h3H,1,4H2,2H3
Toxicity:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
cat | LD | oral | > 800uL/kg (0.8mL/kg) | GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS GASTROINTESTINAL: NAUSEA OR VOMITING | National Technical Information Service. Vol. OTS0521003, |
guinea pig | LCLo | inhalation | 1204ppm/7H (1204ppm) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: COUGH BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Journal of Industrial Hygiene and Toxicology. Vol. 31, Pg. 317, 1949. |
human | TCLo | inhalation | 50ppm (50ppm) | SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 75, 1969. |
monkey | LC | inhalation | > 75ppm/6H (75ppm) | SENSE ORGANS AND SPECIAL SENSES: DEVIATED NASAL SEPTUM: OLFACTION SENSE ORGANS AND SPECIAL SENSES: ULCERATED NASAL SEPTUM: OLFACTION | Toxicologist. Vol. 36(1, Pg. pt2), 113. |
mouse | LC50 | inhalation | 16200mg/m3 (16200mg/m3) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 23(9), Pg. 55, 1979. | |
mouse | LD50 | intraperitoneal | 599mg/kg (599mg/kg) | Journal of Dental Research. Vol. 51, Pg. 526, 1972. | |
mouse | LD50 | oral | 1799mg/kg (1799mg/kg) | Toxicology Letters. Vol. 11, Pg. 125, 1982. | |
mouse | LD50 | skin | 2997mg/kg (2997mg/kg) | National Technical Information Service. Vol. OTS0520999, | |
rabbit | LCLo | inhalation | 1204ppm/7H (1204ppm) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" BEHAVIORAL: ATAXIA | Journal of Industrial Hygiene and Toxicology. Vol. 31, Pg. 317, 1949. |
rabbit | LD50 | oral | 370mg/kg (370mg/kg) | GASTROINTESTINAL: ALTERATION IN GASTRIC SECRETION | National Technical Information Service. Vol. OTS0521003, |
rabbit | LD50 | skin | 500uL/kg (0.5mL/kg) | LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA LIVER: OTHER CHANGES SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" | National Technical Information Service. Vol. OTS0520180, |
rat | LC50 | inhalation | 1414ppm/4H (1414ppm) | SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS LUNGS, THORAX, OR RESPIRATION: DYSPNEA | National Technical Information Service. Vol. OTS0520180, |
rat | LD50 | intraperitoneal | 450mg/kg (450mg/kg) | Archives des Maladies Professionnelles de Medecine du Travail et de Securite Sociale. Vol. 36, Pg. 58, 1975. | |
rat | LD50 | oral | 800mg/kg (800mg/kg) | Bromatologia i Chemia Toksykologiczna. Vol. 12, Pg. 405, 1979. | |
rat | LDLo | skin | 1800mg/kg (1800mg/kg) | Polish Journal of Pharmacology and Pharmacy. Vol. 32, Pg. 223, 1980. |