Name: Trimethylolpropane triacrylate
SKU: 15625-89-5

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Basic Information

Molecular Structure:
CAS No.:	15625-89-5
Name:	Trimethylolpropane triacrylate

Formula:	C₁₅H₂₀O₆
Molecular Weight:	296.32
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;
EINECS:	239-701-3
Density:	1.089 g/cm³
Melting Point:	-66 °C
Boiling Point:	380.9 °C at 760 mmHg
Flash Point:	165 °C
Solubility:	Miscible with water.
Appearance:	Pale yellow to yellow transparent liquid
Hazard Symbols:	Xi
Risk Codes:	36/38-43
Safety:	39
PSA:	78.90000
LogP:	1.57040

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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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

Raw Materials

814-68-6

79-10-7

77-99-6

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Consensus Reports

Reported in EPA TSCA Inventory.

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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Consensus Reports

Specification