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| CAS No.: | 103-11-7 |
|---|---|
| Name: | 2-Ethylhexyl acrylate |
| Molecular Structure: | |
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|
|
| Formula: | C11H20O2 |
| Molecular Weight: | 184.279 |
| Synonyms: | 1-Hexanol, 2-ethyl-, acrylate;2-Ethylhexyl 2-propenoate;Acrylic acid, 2-ethylhexyl ester;BRN 1765828;2-Propenoic acid, 2-ethylhexyl ester;acrylic acid-2-ethyl hexyl ester; |
| EINECS: | 203-080-7 |
| Density: | 0.881 g/cm3 |
| Melting Point: | -90 °C |
| Boiling Point: | 216 °C at 760 mmHg |
| Flash Point: | 79.4 °C |
| Solubility: | <0.1 g/100 mL at 22 °C in water |
| Appearance: | Colorless transparent liquid |
| Hazard Symbols: |
 Xi
|
| Risk Codes: | 37/38-43 |
| Safety: | 36/37-46 |
| PSA: | 26.30000 |
| LogP: | 2.93200 |
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| Conditions | Yield |
|---|---|
| With tetramethoxytitanium; 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy In 2-Methylpentane; cyclohexane at 90 - 110℃; for 6h; | 98% |
| Conditions | Yield |
|---|---|
| With hydroquinone at 115 - 180℃; for 4h; Reagent/catalyst; Inert atmosphere; Dean-Stark; | 83% |
| With hydroquinone In toluene at 93 - 94℃; under 375.038 Torr; for 6h; Pressure; Temperature; Flow reactor; | 80% |
| With alkanesulfonic acid; toluene at 120℃; |
- 500790-28-3
O-acetyl-lactic acid-(2-ethyl-hexyl ester)
- 103-11-7
2-Ethylhexyl acrylate
| Conditions | Yield |
|---|---|
| With pyrexglass at 500℃; |
- 104-76-7
2-Ethylhexyl alcohol
- 79-10-7
acrylic acid
A
- 103-11-7
2-Ethylhexyl acrylate
B
- 38940-91-9
2-ethylhexyl β-2-ethylhexylhydroxypropionate
| Conditions | Yield |
|---|---|
| With KU-23 (10/60) sulphonic cation exchanger; hydroquinone at 90℃; Rate constant; Kinetics; Thermodynamic data; ΔH(excit.), ΔS(excit.), ΔG(excit.); var. sulphonic cation exchangers, var. temperatures; |
| Conditions | Yield |
|---|---|
| With triethylamine In chloroform at 10℃; for 12h; | |
| In dichloromethane |
| Conditions | Yield |
|---|---|
| With 1-methyl-pyrrolidin-2-one; nickel dibromide at 190℃; under 20594.2 Torr; | |
| With hydrogenchloride; tetracarbonyl nickel | |
| With hydrogenchloride; tetracarbonyl nickel |
- 103-11-7
2-Ethylhexyl acrylate
| Conditions | Yield |
|---|---|
| With sulfuric acid; hydroquinone at 189 - 205℃; under 34 - 36 Torr; |
- 103-11-7
2-Ethylhexyl acrylate
| Conditions | Yield |
|---|---|
| Stage #1: acrolein With tert-butylhypochlorite In tetrachloromethane at 30℃; for 3.33333h; Stage #2: 2-Ethylhexyl alcohol In tetrachloromethane at 50℃; for 0.5h; |
| Conditions | Yield |
|---|---|
| With sodium acetate In ISOPROPYLAMIDE | 100% |
| With sodium acetate In ISOPROPYLAMIDE | 100% |
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Specification
2-Ethylhexyl acrylate, also known as 2-Ethylhexyl 2-propenoate, is an organic compound with the formula C11H20O2. It is colorless transparent liquid which is slightly soluble in water and complete soluble in alcohols and ethers. 2-Ethylhexyl acrylate contains a double bond and functional carboxyl group which can make 2-ethylhexyl acrylate form homopolymers and copolymers.
Preparation of 2-Ethylhexyl acrylate: 2-Ethylhexyl acrylate can be obtained by many methods.
1. Direct esterification: First, go through esterification of acrylic acid and 2-ethylhexanol in the presence of sulfuric acid catalyst. And then, after neutralization, dealcoholization and distillation, 2-ethylhexyl acrylate can be obtained.
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2. Transesterification: The acrylic acid 2-ethylhexyl ester can be produced by transesterification from methyl acrylate and 2-ethylhexanol in the presence of titanium tetrachloride catalyst. Then 2-ethylhexyl acrylate can be obtained by distillation.
3. Add a certain amount of acrylic acid, isooctyl alcohol, catalyst (SO42-/ZrO2) and polymerization inhibitor phenothiazine in the reactor. Heat and reflux until no water is out. Then, after alkali washing and water washing to neutral, go through vacuum distillation to collect the 2-ethylhexyl acrylate. Catalyst dosage is 5% of acrylic acid quality, and polymerization inhibitor dosage is 0.05% of acrylic acid quality. The ratio of raw materials ethylhexanol: acrylic acid is 1.2:1. The reaction temperature is 120 °C and the reaction time is 3h.
Uses of 2-Ethylhexyl acrylate: 2-Ethylhexyl acrylate is used for the manufacture of coatings, adhesives, fiber and fabric modification, processing aids, leather processing aids, etc. It is also used as a monomer for the soft polymer. What's more, it can serve as plasticizing effect in copolymer. 2-Ethylhexyl crylate can carry out copolymerization, crosslinking and grafting with other monomers to acrylic resin products used for processing of synthetic fabrics, adhesives, coatings, plastics modification, and many other aspects. Besides, it can be used as a solvent. It is also a very useful feedstock for chemical syntheses, because it readily undergoes addition reactions with a wide variety of organic and inorganic compounds.
2-Ethylhexyl acrylate may cause sensitisation by skin contact. If swallowed, seek medical advice immediately and show this container or label. Besides, this chemical is irritating to respiratory system and skin. When you are using it, wear suitable protective clothing and gloves.
Physical properties about 2-Ethylhexyl acrylate are: (1)ACD/LogP: 4.33; (2)ACD/LogD (pH 5.5): 4.33; (3)ACD/LogD (pH 7.4): 4.33; (4)ACD/BCF (pH 5.5): 1147.92; (5)ACD/BCF (pH 7.4): 1147.92; (6)ACD/KOC (pH 5.5): 5393.65; (7)ACD/KOC (pH 7.4): 5393.65; (8)#H bond acceptors: 2; (9)#Freely Rotating Bonds: 8; (10)Polar Surface Area: 26.3 Å2; (11)Index of Refraction: 1.434; (12)Molar Refractivity: 54.46 cm3; (13)Molar Volume: 209 cm3; (14)Polarizability: 21.59×10-24 cm3; (15)Surface Tension: 27.9 dyne/cm; (16)Density: 0.881 g/cm3; (17)Flash Point: 79.4 °C; (18)Enthalpy of Vaporization: 45.24 kJ/mol; (19)Boiling Point: 216 °C at 760 mmHg; (20)Vapour Pressure: 0.143 mmHg at 25°C.
You can still convert the following datas into molecular structure:
(1)InChI: InChI=1S/C11H20O2/c1-4-7-8-10(5-2)9-13-11(12)6-3/h6,10H,3-5,7-9H2,1-2H3;
(2)InChIKey:InChIKey=GOXQRTZXKQZDDN-UHFFFAOYSA-N;
(3)Smiles:C([C@@H](CCCC)CC)OC(C=C)=O;
The toxicity data of 2-Ethylhexyl acrylate as follows:
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| mammal (species unspecified) | LC50 | inhalation | > 450mg/m3 (450mg/m3) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 56(12), Pg. 19, 1991. |
| mouse | LCLo | inhalation | 600mg/m3 (600mg/m3) | BEHAVIORAL: EXCITEMENT | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 26(9), Pg. 52, 1982. |
| mouse | LD50 | intraperitoneal | 1326mg/kg (1326mg/kg) | Journal of Dental Research. Vol. 51, Pg. 526, 1972. | |
| mouse | LD50 | oral | 4400mg/kg (4400mg/kg) | BEHAVIORAL: EXCITEMENT | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 26(9), Pg. 52, 1982. |
| rabbit | LD50 | skin | 8480uL/kg (8.48mL/kg) | AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 4, Pg. 119, 1951. | |
| rabbit | LDLo | oral | > 4mL/kg (4mL/kg) | National Technical Information Service. Vol. OTS0520808, | |
| rat | LD | skin | > 12gm/kg (12000mg/kg) | Polish Journal of Pharmacology and Pharmacy. Vol. 32, Pg. 223, 1980. | |
| rat | LD50 | intraperitoneal | 1670mg/kg (1670mg/kg) | Archives des Maladies Professionnelles de Medecine du Travail et de Securite Sociale. Vol. 36, Pg. 58, 1975. | |
| rat | LD50 | oral | 6500uL/kg (6.5mL/kg) | Union Carbide Data Sheet. Vol. 11/3/1971, |