2-Ethylhexyl acrylate supplier

Name
2-Ethylhexyl acrylate
EINECS 203-080-7
CAS No. 103-11-7
Article Data32
CAS DataBase
Density 0.881 g/cm³
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
Appearance Colorless transparent liquid
Safety 36/37-46
Risk Codes 37/38-43
Molecular Structure
Hazard Symbols Xi
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;
PSA 26.30000
LogP 2.93200

Synthetic route

: 104-76-7
2-Ethylhexyl alcohol

: 292638-85-8
acrylic acid methyl ester

: 103-11-7
2-Ethylhexyl acrylate

Conditions

Conditions	Yield
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

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

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

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;

...Expand

: 104-76-7
2-Ethylhexyl alcohol

: 814-68-6
acryloyl chloride

: 103-11-7
2-Ethylhexyl acrylate

Conditions

Conditions	Yield
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

Conditions	Yield
With 1-methyl-pyrrolidin-2-one; nickel dibromide at 190℃; under 20594.2 Torr;
With hydrogenchloride; tetracarbonyl nickel
With hydrogenchloride; tetracarbonyl nickel

...Expand

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

Conditions	Yield
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

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;

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

Conditions	Yield
With sodium acetate In ISOPROPYLAMIDE	100%
With sodium acetate In ISOPROPYLAMIDE	100%

...Expand

: 103-11-7
2-Ethylhexyl acrylate

: 58313-23-8
3-iodobenzoic acid methyl ester

: ethyl (E)-3-(3-((2-ethylhexyl)oxy)-3-oxoprop-1-en-1-yl)benzoate

Conditions

Conditions	Yield
With potassium phosphate; sodium chloride In water; N,N-dimethyl-formamide at 45℃; for 16h; Micellar solution;	100%

: 103-11-7
2-Ethylhexyl acrylate

: 347-46-6
4-(N,N-diethylamino)benzenediazonium tetrafluoroborate

: 2'-ethylhexyl 4-N,N-diethylaminocinnamate

Conditions

Conditions	Yield
[(1,3-dimesitylimidazol-2-ylidene)(naphthoquinone)Pd(0)]2 In methanol at 50℃; for 1h; Heck reaction;	99%
(IMes)Pd(NQ) In ethanol at 50℃; for 1h; Conversion of starting material; Heck Reaction;	99%

: 591-50-4
iodobenzene

: 103-11-7
2-Ethylhexyl acrylate

: 16397-78-7
2-ethylhexyl cinnamate

Conditions

Conditions	Yield
With (Bis(tri-tert-butylphosphine)palladium(0)); SPGS-550-M; NOK; triethylamine In water for 5h; Reagent/catalyst; Heck Reaction; Inert atmosphere; Sealed tube;	99%
With triethylamine In N,N-dimethyl-formamide at 120℃; for 3h; Heck Reaction;	90%
With potassium carbonate at 80℃; Heck Reaction; Micellar solution;	82%
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 2h; Catalytic behavior; Heck Reaction; Inert atmosphere; Green chemistry;	56%
With triethylamine at 80℃; for 18h; Heck reaction;	68 %Spectr.

: 103-11-7
2-Ethylhexyl acrylate

: 696-62-8
para-iodoanisole

: 5466-77-3
2-propenoic acid, 3-(4-methoxyphenyl)-, 2-ethylhexyl ester

Conditions

Conditions	Yield
With water; potassium carbonate In 1-methyl-pyrrolidin-2-one at 135℃; for 24h; Catalytic behavior; Heck Reaction;	99%
With tributyl-amine; palladium on activated charcoal; tetrabutylammomium bromide at 120℃; for 4h; Heck Reaction; Inert atmosphere;	99 %Chromat.

: 61589-18-2
N,N-dimethylindoline-1-carboxamide

: 103-11-7
2-Ethylhexyl acrylate

: C22H32N2O3

Conditions

Conditions	Yield
With tetrafluoroboric acid; palladium diacetate; p-benzoquinone In ethyl acetate at 20℃; for 24h; Sealed tube;	99%

: 103-11-7
2-Ethylhexyl acrylate

: 128034-00-4
C13H20N2O

: C24H38N2O3

Conditions

Conditions	Yield
With tetrafluoroboric acid; palladium diacetate; p-benzoquinone In ethyl acetate at 20℃; for 24h; Sealed tube;	99%

: 103-11-7
2-Ethylhexyl acrylate

: 97-54-1
2-methoxy-4-propenylphenol

: (E)-2-ethylhexyl ferulate

Conditions

Conditions	Yield
With Hoveyda-Grubbs catalyst first generation In 1,2-dichloro-ethane at 70℃; Cross Metathesis; Schlenk technique; Inert atmosphere; Glovebox;	98%

: 103-11-7
2-Ethylhexyl acrylate

3-carbethoxyphenyl halide: 3-carbethoxyphenyl halide

: ethyl (E)-3-(3-((2-ethylhexyl)oxy)-3-oxoprop-1-en-1-yl)benzoate

Conditions

Conditions	Yield
With potassium phosphate monohydrate; C64H118O20; sodium chloride In water at 20℃; Heck Reaction;	98%

: 103-11-7
2-Ethylhexyl acrylate

: 696-62-8
para-iodoanisole

: 5466-77-3
2-ethylhexyl methoxycinnamate

Conditions

Conditions	Yield
With tetrabutylammomium bromide; C32H26Cl2N8O4Pd2; potassium carbonate In methanol; water for 0.416667h; Reflux;	97%
With C43H54NO5P; palladium diacetate; triethylamine In water at 40℃; for 12h; Heck Reaction;	95%
With tributyl-amine; chloro-[2-(9-phenyl-1,10-phenanthrolin-2-yl)phenyl]palladium In 1-methyl-pyrrolidin-2-one at 140℃; for 15h; Heck Reaction; Inert atmosphere;	94%

: 103-11-7
2-Ethylhexyl acrylate

: 28170-54-9
3-(3-methoxyphenyl)-1,1-dimethylurea

: C21H32N2O4

Conditions

Conditions	Yield
With tetrafluoroboric acid; palladium diacetate; p-benzoquinone In ethyl acetate at 20℃; for 24h; Sealed tube;	97%

: 103-11-7
2-Ethylhexyl acrylate

: 1609034-51-6
2-ethylhexyl glycidate

Conditions

Conditions	Yield
With sodium hypochlorite; Aliquat 336; sodium hydrogencarbonate In aq. buffer at 40℃; for 1h; pH=8.2; Reagent/catalyst; Green chemistry;	96.8%

: 103-11-7
2-Ethylhexyl acrylate

: 459-64-3
4-methoxybenzenediazonium tetrafluoroborate

: 5466-77-3
2-ethylhexyl methoxycinnamate

Conditions

Conditions	Yield
[(1,3-dimesitylimidazol-2-ylidene)(benzoquinone)Pd(0)]2 In methanol at 50℃; for 1h; Heck reaction;	96%
With calcium carbonate; Lindlar's catalyst In methanol	93%
(IMes)Pd(NQ) In ethanol at 50℃; for 1h; Conversion of starting material; Heck Reaction;	88%
palladium on activated carbon In dichloromethane; water; dimethyl sulfoxide	80%
With xonotlite; palladium diacetate In methanol at 20℃; Reagent/catalyst;	73%

: 103-11-7
2-Ethylhexyl acrylate

: 456-27-9
4-nitrobenzenediazonium tetrafluoroborate

: 2'-ethylhexyl 4-nitrocinnamate

Conditions

Conditions	Yield
[(1,3-dimesitylimidazol-2-ylidene)(naphthoquinone)Pd(0)]2 In methanol at 50℃; for 1h; Heck reaction;	96%
(IMes)Pd(NQ) In ethanol at 50℃; for 1h; Conversion of starting material; Heck Reaction;	96%

: 1046862-39-8
1-nitro-4-(1-phenylbut-3-en-1-yloxy)benzene

: 103-11-7
2-Ethylhexyl acrylate

: 1046862-47-8
(E)-2-ethylhexyl 5-(4-nitrophenoxy)-5-phenylpent-2-enoate

Conditions

Conditions	Yield
Grubbs-Hoveyda second generation catalyst In dichloromethane at 40℃; for 15h;	96%

: 103-11-7
2-Ethylhexyl acrylate

: 1019205-88-9
1-iodo-4-(3,7,11-trimethyldodecyloxy)benzene

: 1019640-46-0
2-ethylhexyl (E)-3-(4-(3,7,11-trimethyldodecyloxy)phenyl)-acrylate

Conditions

Conditions	Yield
With bis(tri-t-butylphosphine)palladium(0); toluene-4-sulfonic acid; triethylamine; sodium chloride In water at 22℃; for 3h; Heck coupling; Inert atmosphere;	96%
With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); pyridinium p-toluenesulfonate; triethylamine In water at 50℃; under 760.051 Torr; for 8h; Heck reaction; Inert atmosphere; Micellar solution;	94%

: 104-76-7
2-Ethylhexyl alcohol

: 103-11-7
2-Ethylhexyl acrylate

: 38940-91-9
2-ethylhexyl β-2-ethylhexylhydroxypropionate

Conditions

Conditions	Yield
Stage #1: 2-Ethylhexyl alcohol With sodium at 60℃; Stage #2: 2-Ethylhexyl acrylate at 60℃; for 12h;	96%

: 103-11-7
2-Ethylhexyl acrylate

: 55792-52-4
acetic acid-(3-propoxy-anilide)

: 1222482-58-7
C22H33NO4

Conditions

Conditions	Yield
With tetrakis(acetonitrile)palladium(II) tetrafluoroborate; silver nitrate; p-benzoquinone In water at 20℃; for 20h; Fujiwara-Moritani reaction; regiospecific reaction;	96%

: 103-11-7
2-Ethylhexyl acrylate

: 6293-37-4
2-ethylhexyl propionate

Conditions

Conditions	Yield
With o-phenylenebis(diphenylphosphine); copper diacetate; poly(methylhydrosiloxane) In toluene; tert-butyl alcohol at 20℃; for 2h;	95%
With 1,2,2,3,4,4-hexamethylphosphetane 1-oxide; phenylsilane; water In toluene at 80℃; for 24h; Schlenk technique; Inert atmosphere;	61%

: 103-11-7
2-Ethylhexyl acrylate

: 101-42-8
fenuron

: C20H30N2O3

Conditions

Conditions	Yield
With tetrafluoroboric acid; palladium diacetate; p-benzoquinone In ethyl acetate at 20℃; for 24h; Sealed tube;	95%

: 14285-68-8
decacarbonyldirhenium(0)

: 103-11-7
2-Ethylhexyl acrylate

: N-[1-(1-cyclohexen-1-yl)ethylidene]benzamine

: (C9H9CH3CO2CH2CH(C2H5)(CH2)3CH3)Re(CO)3

Conditions

Conditions	Yield
In xylene byproducts: C9H10CH3CO2CH2CH(C2H5)(CH2)3CH3; xylene, 150°C, 72 h; as oil;	94%
In toluene byproducts: C9H10CH3CO2CH2CH(C2H5)(CH2)3CH3; toluene, 150°C, 24 h;	4%

...Expand

: 16619-14-0
2-phenyl-2,3-dihydro-1H-quinolin-4-one

: 103-11-7
2-Ethylhexyl acrylate

: C26H31NO3

Conditions

Conditions	Yield
With silver hexafluoroantimonate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; copper diacetate In 1,2-dichloro-ethane at 100℃; for 5h; chemoselective reaction;	94%

: 103-11-7
2-Ethylhexyl acrylate

: 106-53-6
para-bromobenzenethiol

: 881664-08-0
3-(4-bromophenylsulfanyl)propionic acid 2-ethylhexyl ester

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 15h;	93%

: 103-11-7
2-Ethylhexyl acrylate

: 40742-21-0
1‐(but‐3‐en‐1‐yloxy)‐4‐nitrobenzene

: 1046862-42-3
(E)-2-ethylhexyl 5-(4-nitrophenoxy)pent-2-enoate

Conditions

Conditions	Yield
Grubbs-Hoveyda second generation catalyst In dichloromethane at 40℃; for 15h;	93%

: 103-11-7
2-Ethylhexyl acrylate

: 120105-59-1
3’H-spiro[indole-3,2’-[1,3]]benzothiazole-2(1H)-one

: bis(2-ethylhexyl) 3,3'-(2'-oxo-3H-spiro[benzo[d]thiazole-2,3'-indoline]-1',3-diyl)dipropionate

Conditions

Conditions	Yield
With tetrabutylammomium bromide; potassium carbonate In neat (no solvent) at 20℃; for 3h; Michael Addition; Green chemistry; regioselective reaction;	93%

: 79-41-4
poly(methacrylic acid)

: 103-11-7
2-Ethylhexyl acrylate

poly(methacrylic acid-co-2-ethylhexyl acrylate): poly(methacrylic acid-co-2-ethylhexyl acrylate)

Conditions

Conditions	Yield
With dimethyl 2,2'-azobis(isobutyrate); 2,4-diphenyl-4-methyl-pent-1-ene In isopropyl alcohol at 80℃; for 20h;	92.53%

: 107-45-9
tert-Octylamine

: 103-11-7
2-Ethylhexyl acrylate

: 696-62-8
para-iodoanisole

: 5466-77-3
2-ethylhexyl methoxycinnamate

Conditions

Conditions	Yield
With acetic acid; palladium on charcoal	92%

...Expand

palladium of charcoal: palladium of charcoal

: 103-11-7
2-Ethylhexyl acrylate

: 696-62-8
para-iodoanisole

: 5466-77-3
2-ethylhexyl methoxycinnamate

Conditions

Conditions	Yield
With triethylamine In water; toluene	92%

...Expand

: 14159-55-8
2-cyclohex-1-enyl-pyridine

: 103-11-7
2-Ethylhexyl acrylate

: 1161621-73-3
2-ethylhexyl 3-[2-(2-pyridyl)-1-cyclohexenyl]propionate

Conditions

Conditions	Yield
With bromotricarbonyl(tetrahydrofuran)rhenium(I) dimer In toluene at 135℃; for 24h; Inert atmosphere;	91%

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. 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 (SO₄^2-/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,

Product Name

2-Ethylhexyl acrylate

Synthetic route

2-Ethylhexyl acrylate Consensus Reports

2-Ethylhexyl acrylate Specification

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