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Trimethylolpropane triacrylate
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Name

Trimethylolpropane triacrylate

 EINECS 239-701-3
CAS No. 15625-89-5 Density 1.089 g/cm3
PSA 78.90000 LogP 1.57040
Solubility Miscible with water. Melting Point -66 °C
Formula C15H20O6 Boiling Point 380.9 °C at 760 mmHg
Molecular Weight 296.32 Flash Point 165 °C
Transport Information N/A Appearance Pale yellow to yellow transparent liquid
Safety 39 Risk Codes 36/38-43
Molecular Structure Molecular Structure of 15625-89-5 (Trimethylolpropane triacrylate) Hazard Symbols IrritantXi
Synonyms

2-Propenoicacid, 2-ethyl-2-[[(1-oxo-2-propenyl)oxy]methyl]-1,3-propanediyl ester (9CI);1,3-Propanediol, 2-ethyl-2-(hydroxymethyl)-, triacrylate (8CI);2-Ethyl-2-(hydroxymethyl)-1,3-propanediol triacrylate;A-TMPT;Ageflex TMPTA;Aronix M 309;Blemmer ATT;Etermer231;Genomer 1330;

Article Data 9

Trimethylolpropane triacrylate Synthetic route

77-99-6

1,1,1-tri(hydroxymethyl)propane

814-68-6

acryloyl chloride

15625-89-5

2-((acryloyloxy)methyl)-2-ethylpropane-1,3-diyl diacrylate

Conditions
ConditionsYield
With 4-methoxy-phenol; triethylamine; hydroquinone at 60℃; for 2h; Temperature;98.38%
In pyridine; benzene at 50℃; for 30h;81%
With pyridine In benzene at 50℃; for 30h;81%
77-99-6

1,1,1-tri(hydroxymethyl)propane

79-10-7

acrylic acid

15625-89-5

2-((acryloyloxy)methyl)-2-ethylpropane-1,3-diyl diacrylate

Conditions
ConditionsYield
With methanesulfonic acid; hypophosphorous acid; hydroquinone In cyclohexane at 70 - 91℃; under 3750.38 Torr;95%
Stage #1: With hypophosphorous acid; 4-methoxy-phenol; copper dichloride In cyclohexane; water at 70 - 75℃;
Stage #2: 1,1,1-tri(hydroxymethyl)propane; acrylic acid With toluene-4-sulfonic acid In cyclohexane; water at 95 - 130℃; for 6 - 10h;
With methanesulfonic acid; hydroquinone In toluene at 120℃; for 5h;
37275-47-1

trimethylolpropane diacrylate

292638-85-8

acrylic acid methyl ester

15625-89-5

2-((acryloyloxy)methyl)-2-ethylpropane-1,3-diyl diacrylate

Conditions
ConditionsYield
With dmap; oxo[hexa(trifluoroacetato)]tetrazinc In toluene at 80℃; for 72h; Inert atmosphere; Schlenk technique; chemoselective reaction;63%
15625-89-5

2-((acryloyloxy)methyl)-2-ethylpropane-1,3-diyl diacrylate

60-24-2

2-hydroxyethanethiol

2-ethyl-2-(((3-((2-hydroxyethyl)thio)propanoyl)oxy)methyl)propane-1,3-diyl bis(3-((2-hydroxyethyl)thio)propanoate)

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 0 - 20℃; Inert atmosphere;100%
110-60-1

1,4-diaminobutane

15625-89-5

2-((acryloyloxy)methyl)-2-ethylpropane-1,3-diyl diacrylate

C64H92N2O24

Conditions
ConditionsYield
In methanol at 10 - 25℃; for 26h; Inert atmosphere;95.02%
124-09-4

1,6-Hexanediamine

15625-89-5

2-((acryloyloxy)methyl)-2-ethylpropane-1,3-diyl diacrylate

C66H96N2O24

Conditions
ConditionsYield
In methanol at 10 - 25℃; for 26h; Inert atmosphere;94.5%
In methanol at 4 - 30℃; for 18h;
15625-89-5

2-((acryloyloxy)methyl)-2-ethylpropane-1,3-diyl diacrylate

66943-05-3

1,4,7,10-tetraoxa-15-azacyclopentadecane

3-(1,4,7,10-tetraoxa-13-aza-cyclopentadec-13-yl)-propionic acid 2,2-bis-(3-1,4,7,10-tetraoxa-13-aza-cyclopentadec-13-yl-propionyloxymethyl)-butyl ester

Conditions
ConditionsYield
In methanol at 50℃; for 24h;82.8%
33941-15-0

1-aza-18-crown-6

15625-89-5

2-((acryloyloxy)methyl)-2-ethylpropane-1,3-diyl diacrylate

3-(1,4,7,10,13-pentaoxa-16-aza-cyclooctadec-16-yl)-propionic acid 2,2-bis-(3-1,4,7,10,13-pentaoxa-16-aza-cyclooctadec-16-yl-propionyloxymethyl)-butyl ester

Conditions
ConditionsYield
In methanol at 50℃; for 24h;81%
15625-89-5

2-((acryloyloxy)methyl)-2-ethylpropane-1,3-diyl diacrylate

829-85-6

diphenylphosphane

C51H53O6P3

Conditions
ConditionsYield
In 2-methyltetrahydrofuran at 90℃; for 12h; Inert atmosphere; Sealed tube; Green chemistry; regioselective reaction;81%
1121-60-4

pyridine-2-carbaldehyde

15625-89-5

2-((acryloyloxy)methyl)-2-ethylpropane-1,3-diyl diacrylate

1352877-62-3

mono(β-hydroxy-α-methylene-2-pyridinepropanoic acid)-diacryloyl trimethylolpropane

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane; methanol In N,N-dimethyl-formamide at 20℃; for 5h;80.5%

Trimethylolpropane triacrylate Consensus Reports

Reported in EPA TSCA Inventory.

Trimethylolpropane triacrylate Specification

The IUPAC name of Trimethylolpropane triacrylate is 2,2-bis(prop-2-enoyloxymethyl)butyl prop-2-enoate . With the CAS registry number 15625-89-5, it is also named as 1,3-Propanediol, 2-ethyl-2-(hydroxymethyl)-, triacrylate ; 2-Ethyl-2-(hydroxymethyl)-1,3-propanediol triacrylate ; Acrylic acid, 1,1,1-(trihydroxymethyl)propane triester ; NK Ester A TMPT ; Ogumont T 200 ; TMPTA ; Viscoat 295 ; 2-Propenoic acid, 1,1'-(2-ethyl-2-(((1-oxo-2-propen-1-yl)oxy)methyl)-1,3-propanediyl) ester . 

When heated to decomposition it emits acrid smoke and irritating fumes. This product is mildly toxic by ingestion. It is irritating to eyes and skin. It may cause sensitization by skin contact. If you want to contact the product, you must wear eye / face protection.

The Trimethylolpropane triacrylate is functional monomer with the appreance is pale yellow to yellow transparent liquid. It has the property of resistance against weather, chemical, water and abrasion. So this product can be used in manufacture of acrylic glue, plastic, adhesive, anaerobic sealant, Ink which is useful in the low volatility and fast cure response.

The other characteristics of this product can be summarized as: (1)ACD/BCF (pH 5.5): 8.09 ; (2)ACD/BCF (pH 7.4): 8.09 ; (3)ACD/KOC (pH 5.5): 155.43 ; (4)ACD/KOC (pH 7.4): 155.43 ; (5)#H bond acceptors: 6 ; (6)#H bond donors: 0 ; (7)#Freely Rotating Bonds: 13 ; (8)Index of Refraction: 1.471 ; (9)Molar Refractivity: 76 cm3 ; (10)Molar Volume: 271.9 cm3 ; (11)Polarizability: 30.13×10-24 cm3 ; (12)Surface Tension: 35.8 dyne/cm ; (13)Enthalpy of Vaporization: 62.91 kJ/mol ; (14)Vapour Pressure: 5.27E-06 mmHg at 25°C.

People can use the following data to convert to the molecule structure. SMILES: O=C(OCC(COC(=O)\C=C)(CC)COC(=O)\C=C)\C=C; InChI: InChI=1/C15H20O6/c1-5-12(16)19-9-15(8-4,10-20-13(17)6-2)11-21-14(18)7-3/h5-7H,1-3,8-11H2,4H3. 

The following is the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rabbit LD50 skin 5170mg/kg (5170mg/kg)   American Industrial Hygiene Association Journal. Vol. 42(11), Pg. B53, 1981.
rat LD50 intraperitoneal 55mg/kg (55mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA		 National Technical Information Service. Vol. OTS0555702,
rat LD50 oral 5190uL/kg (5.19mL/kg)   Toxicology and Applied Pharmacology. Vol. 28, Pg. 313, 1974.
 

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