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2-Ethylhexyl acrylate

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Name

2-Ethylhexyl acrylate

EINECS 203-080-7
CAS No. 103-11-7 Density 0.881 g/cm3
PSA 26.30000 LogP 2.93200
Solubility <0.1 g/100 mL at 22 °C in water Melting Point -90 °C
Formula C11H20O2 Boiling Point 216 °C at 760 mmHg
Molecular Weight 184.279 Flash Point 79.4 °C
Transport Information N/A Appearance Colorless transparent liquid
Safety 36/37-46 Risk Codes 37/38-43
Molecular Structure Molecular Structure of 103-11-7 (2-Ethylhexyl acrylate) Hazard Symbols IrritantXi
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;

Article Data 32

2-Ethylhexyl acrylate Synthetic route

104-76-7

2-Ethylhexyl alcohol

292638-85-8

acrylic acid methyl ester

103-11-7

2-Ethylhexyl acrylate

Conditions
ConditionsYield
With tetramethoxytitanium; 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy In 2-Methylpentane; cyclohexane at 90 - 110℃; for 6h;98%
104-76-7

2-Ethylhexyl alcohol

79-10-7

acrylic acid

103-11-7

2-Ethylhexyl acrylate

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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;
104-76-7

2-Ethylhexyl alcohol

814-68-6

acryloyl chloride

103-11-7

2-Ethylhexyl acrylate

Conditions
ConditionsYield
With triethylamine In chloroform at 10℃; for 12h;
In dichloromethane
104-76-7

2-Ethylhexyl alcohol

74-86-2

acetylene

carbon monoxide

carbon monoxide

103-11-7

2-Ethylhexyl acrylate

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one; nickel dibromide at 190℃; under 20594.2 Torr;
With hydrogenchloride; tetracarbonyl nickel
With hydrogenchloride; tetracarbonyl nickel
diethyl ether dicarboxylic acid-(2.2')-bis-<2-ethyl-hexyl ester>

diethyl ether dicarboxylic acid-(2.2')-bis-<2-ethyl-hexyl ester>

103-11-7

2-Ethylhexyl acrylate

Conditions
ConditionsYield
With sulfuric acid; hydroquinone at 189 - 205℃; under 34 - 36 Torr;

hydroxypropyl Acrylate

103-11-7

2-Ethylhexyl acrylate

104-76-7

2-Ethylhexyl alcohol

107-02-8

acrolein

103-11-7

2-Ethylhexyl acrylate

Conditions
ConditionsYield
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;
trans-di-μ-acetato-bis ›o-(di-o-tolylphosphino)[benzyl]dipalladium

trans-di-μ-acetato-bis ›o-(di-o-tolylphosphino)[benzyl]dipalladium

103-11-7

2-Ethylhexyl acrylate

99-90-1

para-bromoacetophenone

2-ethylhexyl E-4-acetylcinnamate

Conditions
ConditionsYield
With sodium acetate In ISOPROPYLAMIDE100%
With sodium acetate In ISOPROPYLAMIDE100%

2-Ethylhexyl acrylate Consensus Reports

Reported in EPA TSCA Inventory.

2-Ethylhexyl acrylate 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.

2-Ethylhexyl acrylate can be obtained by acrylic acid and 2-ethylhexanol
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,

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