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818-61-1

Basic Information
CAS No.: 818-61-1
Name: 2-Hydroxyethyl acrylate
Article Data: 45
Molecular Structure:
Molecular Structure of 818-61-1 (2-Hydroxyethyl acrylate)
Formula: C5H8O3
Molecular Weight: 116.117
Synonyms: Acrylicacid, 2-hydroxyethyl ester (6CI,8CI);2-(Acryloyloxy)ethanol;2-Hydroxyethyl2-propenoate;2HEA;AHEC-T;Acryics HEA;BHEA;2-Propenoic acid,2-hydroxyethyl ester;Ethylene glycol monoacrylate;HEA;HOA;Light Acrylate HOA;Light EsterHOA;Light Ester OA;Perm A;Perm A (monomer);Rocryl 420;Viscoat 220;b-Hydroxyethyl acrylate;
EINECS: 212-454-9
Density: 1.083 g/cm3
Melting Point: -60 °C
Boiling Point: 196.2 °C at 760 mmHg
Flash Point: 98.3 °C
Solubility: Soluble in water
Appearance: clear colorless liquid
Hazard Symbols: ToxicT, DangerousN
Risk Codes: 24-34-43-50-20/22
Safety: 26-36/39-45-61-36/37/39
Transport Information: UN 2927 6.1/PG 2
PSA: 46.53000
LogP: -0.29210
Synthetic route
75-21-8

oxirane

79-10-7

acrylic acid

818-61-1

2-hydroxyethyl acrylate

Conditions
ConditionsYield
With magnetic zeolite at 63℃; for 2h; Temperature;97.5%
With chromium(lll) acetate; 4-methoxy-phenol; hydroquinone In water at 80℃; under 5625.56 Torr; for 1.5h; Temperature; Inert atmosphere;97.91%
With 10H-phenothiazine; chromium acetate at 80 - 90℃; under 750.075 Torr; for 3.7 - 5.2h;81%
107-21-1

ethylene glycol

79-10-7

acrylic acid

818-61-1

2-hydroxyethyl acrylate

Conditions
ConditionsYield
With iodine for 4h; Reflux;71%
With toluene-4-sulfonic acid
toluene-4-sulfonic acid
41440-38-4

2-acryloyloxyethanol vinyl ether

818-61-1

2-hydroxyethyl acrylate

Conditions
ConditionsYield
With sulfuric acid
107-21-1

ethylene glycol

814-68-6

acryloyl chloride

818-61-1

2-hydroxyethyl acrylate

Conditions
ConditionsYield
With chloroform; sodium sulfate; sodium sulfite
With triethylamine In chloroform at 10℃; for 12h;
7446-81-3

sodium 2-propenoate

540-51-2

2-bromoethanol

818-61-1

2-hydroxyethyl acrylate

Conditions
ConditionsYield
With water
10192-85-5

potassium acrylate

107-07-3

2-chloro-ethanol

818-61-1

2-hydroxyethyl acrylate

Conditions
ConditionsYield
With copper(l) chloride
79-10-7

acrylic acid

818-61-1

2-hydroxyethyl acrylate

Conditions
ConditionsYield
anion exchange resin Conversion of starting material;
DIAION SA10A Conversion of starting material;
anion exchange resin Conversion of starting material;
oxirane
75-21-8

oxirane

79-10-7

acrylic acid

A

2274-11-5

ethylene glycol diacrylate

B

13533-05-6

2-(2-acryloyloxyethyloxy)ethyl alcohol

C

818-61-1

2-hydroxyethyl acrylate

Conditions
ConditionsYield
With 10H-phenothiazine; chromium(II) acetate at 60℃; under 7500.75 Torr; for 6.5h;
chromium(lll) acetate; 4-methoxy-phenol at 50 - 70℃; under 375.038 Torr; for 4 - 7h; Autoclave;
75-21-8

oxirane

79-10-7

acrylic acid

A

4074-88-8

diethyleneglycol(diacrylate)

B

16695-45-7

triethylene glycol monoacrylate

C

818-61-1

2-hydroxyethyl acrylate

Conditions
ConditionsYield
With 10H-phenothiazine at 50℃; under 7500.75 Torr; for 5h; Product distribution / selectivity;
With 10H-phenothiazine; Catalyst A : 270 g Böhmit (Pural SB of Sasol comp.) and 30 g NH4Fe [Fe (CN) 6] at 50℃; under 7500.75 Torr; for 5h; Product distribution / selectivity;
With 10H-phenothiazine; Catalyst C : 297 g Böhmit (Pural SB of Sasol comp.) and 3 g Fe4 [Fe (CN) 6] 3 (Berliner-Blau) at 50℃; under 7500.75 Torr; for 5h; Product distribution / selectivity;
75-21-8

oxirane

79-10-7

acrylic acid

A

13533-05-6

2-(2-acryloyloxyethyloxy)ethyl alcohol

B

818-61-1

2-hydroxyethyl acrylate

Conditions
ConditionsYield
With 10H-phenothiazine; chromium(lll) acetate at 85℃; under 3.0003 - 375.038 Torr; for 3 - 3.3h; Product distribution / selectivity;
With 10H-phenothiazine; Octanoic acid; chromium(lll) acetate at 85℃; under 375.038 Torr; for 3.2h; Product distribution / selectivity;
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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The Acrylic acid-2-hydroxyethyl ester is an organic compound with the formula C5H8O3. The IUPAC name of this chemical is 2-hydroxyethyl prop-2-enoate. With the CAS registry number 818-61-1, it is also named as 2-propenoic acid, 2-hydroxyethyl ester. The product's categories are Monomer; Ethylene Glycols & Monofunctional Ethylene Glycols; Monofunctional Ethylene Glycols. Besides, it is used in radiation curing system in the reactive diluent and crosslinking agent, and it may be used as crosslinking resins, plastics, rubber modifier.

Physical properties about Acrylic acid-2-hydroxyethyl ester are: (1)ACD/LogP: -0.06; (2)ACD/LogD (pH 5.5): -0.05; (3)ACD/LogD (pH 7.4): -0.05; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 22.24; (7)ACD/KOC (pH 7.4): 22.24; (8)#H bond acceptors: 3; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 5; (11)Polar Surface Area: 35.53 Å2; (12)Index of Refraction: 1.44; (13)Molar Refractivity: 28.24 cm3; (14)Molar Volume: 107.1 cm3; (15)Polarizability: 11.19×10-24cm3; (16)Surface Tension: 35.4 dyne/cm; (17)Density: 1.083 g/cm3; (18)Flash Point: 98.3 °C; (19)Enthalpy of Vaporization: 50.31 kJ/mol; (20)Boiling Point: 196.2 °C at 760 mmHg; (21)Vapour Pressure: 0.104 mmHg at 25°C.

Preparation: this chemical can be prepared by Acrylic acid and ethylene oxide in the catalyst (vanadium trichloride, chromium acetate chromium or acrylic). Reaction as follows:



Uses of Acrylic acid-2-hydroxyethyl ester: it can be used to (acryloyloxyethyleneoxy)(tert-butylperoxy)dimethylsilane at room temperature. It will need reagent Et3N and solvent hexane. The yield is about 76.4%.

When you are using this chemical, please be cautious about it as the following:
It is harmful by inhalation and if swallowed and toxic in contact with skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Besides, this chemical can cause burns and may cause sensitisation by skin contact, it is very toxic to aquatic organisms. When you are using it, wear suitable gloves and eye/face protection. In case of accident or if you feel unwell seek medical advice immediately (show the label where possible).

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OCCO)\C=C
(2)InChI: InChI=1/C5H8O3/c1-2-5(7)8-4-3-6/h2,6H,1,3-4H2
(3)InChIKey: OMIGHNLMNHATMP-UHFFFAOYAK
(4)Std. InChI: InChI=1S/C5H8O3/c1-2-5(7)8-4-3-6/h2,6H,1,3-4H2
(5)Std. InChIKey: OMIGHNLMNHATMP-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral 300mg/kg (300mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

GASTROINTESTINAL: ALTERATION IN GASTRIC SECRETION
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 24(4), Pg. 56, 1980.
rabbit LD50 skin 298mg/kg (298mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: MUSCLE WEAKNESS
National Technical Information Service. Vol. OTS0555795,
rat LCLo inhalation 500ppm/4H (500ppm)   AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 4, Pg. 119, 1951.
rat LD50 oral 548mg/kg (548mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
National Technical Information Service. Vol. OTS0555795,