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Trimethylol propane

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Name

Trimethylol propane

EINECS 201-074-9
CAS No. 77-99-6 Density 1.116 g/cm3
PSA 60.69000 LogP -0.64030
Solubility soluble in water Melting Point 56-58 °C(lit.)
Formula C6H14O3 Boiling Point 295.7 °C at 760 mmHg
Molecular Weight 134.20 Flash Point 147.7 °C
Transport Information Appearance white crystalline flakes
Safety 22-24/25 Risk Codes
Molecular Structure Molecular Structure of 77-99-6 (Trimethylol propane) Hazard Symbols
Synonyms

NSC 3576;Propane,1,1,1-tris(hydroxymethyl)-;RC Crosslinker TR;TMP;TMP (alcohol);Hexaglycerine;Tris(hydroxymethyl)propane;Trimethylol Propane (TMP);1,1,1-Tri(hydroxymethyl)propane;1,1,1-Trimethylolpropane;1,1,1-Tris(hydroxymethyl)propane;2,2-Bis(hydroxymethyl)-1-butanol;2-Ethyl-2-(hydroxymethyl)-1,3-propanediol;2-Ethyl-2-(hydroxymethyl)propanediol;Addolink TR;Ethriol;Ethyltrimethylolmethane;Ettriol;

 

Trimethylol propane Synthetic route

50-00-0

formaldehyd

123-72-8

butyraldehyde

77-99-6

1,1,1-tri(hydroxymethyl)propane

Conditions
ConditionsYield
With water; sodium hydroxide In ethanol at 55℃; for 0.0833333h; Temperature;90%
With calcium hydroxide
With sodium hydroxide In water at 40 - 60℃; for 0.75h;
123-72-8

butyraldehyde

77-99-6

1,1,1-tri(hydroxymethyl)propane

Conditions
ConditionsYield
With sodium hydroxide; formaldehyd; triethylamine; Ni-Cr-Al88.5%
With formaldehyd; triethylamine In water82.77%
With formaldehyd; triethylamine In water81.59%
41966-25-0

2,2-dimethylolbutanal

77-99-6

1,1,1-tri(hydroxymethyl)propane

Conditions
ConditionsYield
With hydrogen at 115℃; under 22502.3 Torr; for 8h;84.8%
With hydrogen; Cu/TiO2 catalyst B of PCT/WO 02/85825; activated at 110℃; under 67506.8 Torr; for 2112h; Conversion of starting material;
With hydrogen; citric acid; activated Cu/TiO2 catalyst J PCT/WO 99/44974 In water at 120℃; under 60006 Torr; Conversion of starting material;
With hydrogen at 120℃; under 22502.3 Torr;
copper-II acetate

copper-II acetate

7397-44-6

tris-methylamino-borane

123-72-8

butyraldehyde

77-99-6

1,1,1-tri(hydroxymethyl)propane

Conditions
ConditionsYield
With triethylamine In methanol; formaldehyd74.6%
922-63-4

ethylacrolein

50-00-0

formaldehyd

A

bis-TMP

B

77-99-6

1,1,1-tri(hydroxymethyl)propane

C

23235-61-2

3,3,7,7-tetra(hydroxymethyl)-5-oxanonane

Conditions
ConditionsYield
In water at 96 - 100℃; for 3.3h;A 2%
B 67.5%
C 15%
1313-99-1

nickel(II) oxide

Al2 O3

Al2 O3

123-72-8

butyraldehyde

77-99-6

1,1,1-tri(hydroxymethyl)propane

Conditions
ConditionsYield
With formaldehyd; triethylamine14%
103205-80-7

2-hydroxymethyl-2-vinyl-propane-1,3-diol

77-99-6

1,1,1-tri(hydroxymethyl)propane

Conditions
ConditionsYield
With palladium on activated charcoal; ethanol Hydrogenation;
95461-66-8

2,2-bis(hydroxymethyl)-1,4-butanediol

77-99-6

1,1,1-tri(hydroxymethyl)propane

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sodium acetate
2: 500 °C
3: barium methylate; methanol
4: palladium/charcoal; ethanol / Hydrogenation
View Scheme
105790-11-2

4-acetoxy-3,3-bis-acetoxymethyl-but-1-ene

77-99-6

1,1,1-tri(hydroxymethyl)propane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: barium methylate; methanol
2: palladium/charcoal; ethanol / Hydrogenation
View Scheme

1,4-diacetoxy-2,2-bis-acetoxymethyl-butane

77-99-6

1,1,1-tri(hydroxymethyl)propane

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 500 °C
2: barium methylate; methanol
3: palladium/charcoal; ethanol / Hydrogenation
View Scheme
50-00-0

formaldehyd

123-72-8

butyraldehyde

A

bis-TMP

B

77-99-6

1,1,1-tri(hydroxymethyl)propane

C

23235-61-2

3,3,7,7-tetra(hydroxymethyl)-5-oxanonane

Reaxys ID: 11464418

Reaxys ID: 11464418

A

77-99-6

1,1,1-tri(hydroxymethyl)propane

B

23235-61-2

3,3,7,7-tetra(hydroxymethyl)-5-oxanonane

C

5187-23-5

5-ethyl-1,3-dioxane-5-methanol

Conditions
ConditionsYield
With toluene-4-sulfonic acid In water at 90℃; for 6h;A n/a
B 5.9 g
C n/a
With toluene-4-sulfonic acid In water at 90℃; for 6h;A n/a
B 15.2 g
C n/a
crude TMP

crude TMP

77-99-6

1,1,1-tri(hydroxymethyl)propane

Conditions
ConditionsYield
Stage #1: crude TMP With phosphoric acid at 150℃; under 50 Torr; for 1h;
Stage #2: With phosphoric acid at 180℃; for 1h;
41966-25-0

2,2-dimethylolbutanal

A

67-56-1

methanol

B

77-99-6

1,1,1-tri(hydroxymethyl)propane

C

58828-90-3

trimethylamine-formic acid complex

Conditions
ConditionsYield
With hydrogen In water at 115℃; under 67506.8 Torr;
110-89-4

piperidine

2591-86-8

N-Formylpiperidine

77-99-6

1,1,1-tri(hydroxymethyl)propane

108-30-5

succinic acid anhydride

6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

77-99-6

1,1,1-tri(hydroxymethyl)propane

Conditions
ConditionsYield
With pyridine In 5,5-dimethyl-1,3-cyclohexadiene; dichloromethane
50-00-0

formaldehyd

41966-25-0

2,2-dimethylolbutanal

A

77-99-6

1,1,1-tri(hydroxymethyl)propane

B

141-53-7

sodium formate

Conditions
ConditionsYield
With sodium hydroxide In water at 45 - 50℃; for 3.75 - 4.25h; Product distribution / selectivity; Cannizzaro Reaction;
50-00-0

formaldehyd

123-72-8

butyraldehyde

A

922-63-4

ethylacrolein

B

77-99-6

1,1,1-tri(hydroxymethyl)propane

Conditions
ConditionsYield
With water; sodium carbonate at 73 - 84℃; Product distribution / selectivity;
With sodium carbonate In water Reagent/catalyst; Temperature; Concentration; Reflux;A 58 g
B 15 g
922-63-4

ethylacrolein

50-00-0

formaldehyd

A

77-99-6

1,1,1-tri(hydroxymethyl)propane

B

23235-61-2

3,3,7,7-tetra(hydroxymethyl)-5-oxanonane

Conditions
ConditionsYield
Stage #1: ethylacrolein; formaldehyd In water at 100℃;
Stage #2: With sodium hydroxide In water at 100℃; Reagent/catalyst; Time; Concentration;
A 253 g
B 66 g

C6H11O3(3-)*Sb(3+)

77-99-6

1,1,1-tri(hydroxymethyl)propane

Conditions
ConditionsYield
With water-d2 In dimethylsulfoxide-d6 Glovebox;
50-00-0

formaldehyd

123-72-8

butyraldehyde

A

77-99-6

1,1,1-tri(hydroxymethyl)propane

B

41966-25-0

2,2-dimethylolbutanal

Conditions
ConditionsYield
With triethylamine at 35℃; for 3h; Cannizzaro Reaction;
50-00-0

formaldehyd

123-72-8

butyraldehyde

A

67-56-1

methanol

B

77-99-6

1,1,1-tri(hydroxymethyl)propane

Conditions
ConditionsYield
With potassium hydroxide In water at 60℃; for 1h; Temperature; Cannizzaro Reaction;A 11.71 %Chromat.
B 76.63 %Chromat.
77-99-6

1,1,1-tri(hydroxymethyl)propane

107-05-1

3-chloroprop-1-ene

682-08-6

trimethylolpropane triallyl ether

Conditions
ConditionsYield
With sodium hydroxide; sodium chloride; tetrabutylammomium bromide In toluene100%
With sodium hydroxide; tetrabutylammomium bromide 1.) water, 80 deg C, 0.5 h, 2.) 80 deg C, 7 h; Yield given. Multistep reaction;
With sodium hydroxide; tetrabutylammomium bromide In water at 45℃; for 22h; Allylation;
With tetrabutylammomium bromide; sodium hydroxide at 45℃; for 22h;
4870-65-9

2-bromophenylacetic acid

77-99-6

1,1,1-tri(hydroxymethyl)propane

Bromo-phenyl-acetic acid 2,2-bis-(2-bromo-2-phenyl-acetoxymethyl)-butyl ester

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene at 110℃;100%
77-99-6

1,1,1-tri(hydroxymethyl)propane

5455-98-1

2-oxiranylmethylisoindole-1,3-dione

556-52-5

oxiranyl-methanol

C72H107N3O34

Conditions
ConditionsYield
Stage #1: 1,1,1-tri(hydroxymethyl)propane With potassium tert-butylate In tetrahydrofuran at 120℃; for 18h; Inert atmosphere;
Stage #2: oxiranyl-methanol In tetrahydrofuran at 120℃; for 0.5h; Inert atmosphere;
Stage #3: 2-oxiranylmethylisoindole-1,3-dione In tetrahydrofuran at 120℃; Inert atmosphere;
100%
77-99-6

1,1,1-tri(hydroxymethyl)propane

600-17-9

vinyl glycolic acid

C18H26O9

Conditions
ConditionsYield
With salicylaldehyde In toluene at 100℃; for 14h; Catalytic behavior; Reagent/catalyst; Inert atmosphere;100%
77-99-6

1,1,1-tri(hydroxymethyl)propane

90-02-8

salicylaldehyde

22251-64-5

2-[(5-ethyl-5-hydroxymethyl)-1,3-dioxan-2-yl]phenol

Conditions
ConditionsYield
With sulfuric acid at 80℃;100%
77-99-6

1,1,1-tri(hydroxymethyl)propane

105-58-8

Diethyl carbonate

A

trimethylolpropane cyclic monocarbonate

B

1286272-49-8

C9H18O5

Conditions
ConditionsYield
With Novozym435 at 60℃; for 48h; Molecular sieve; Enzymatic reaction; neat (no solvent);A 6%
B 99.4%
77-99-6

1,1,1-tri(hydroxymethyl)propane

67-64-1

acetone

20761-68-6

1,3-dioxa-5-ethyl-2,2-dimethyl-5-cyclohexylmethanol

Conditions
ConditionsYield
With toluene-4-sulfonic acid In water; Petroleum ether for 10h; Reflux;99%
With toluene-4-sulfonic acid at 20℃; for 16h;78%
With toluene-4-sulfonic acid In Petroleum ether Heating;76%
77-99-6

1,1,1-tri(hydroxymethyl)propane

1821-12-1

4-Phenylbutyric acid

1,1,1-tri(4-phenylbutyroxymethyl)propane

Conditions
ConditionsYield
tetrachlorobis(tetrahydrofuran)hafnium(IV) In toluene for 24h; Heating;99%
With molecualar sevies 4A; tetrachlorobis(tetrahydrofuran)hafnium(IV) In toluene at 120℃; for 24h;99%
77-99-6

1,1,1-tri(hydroxymethyl)propane

1067-52-3

tributyltin methoxide

79428-57-2

1,1,1-tris(tributyltinoxymethyl) propane

Conditions
ConditionsYield
In neat (no solvent) 1,1,1-trymethylolpropane to methoxytributyltin ratio 1:3; mixed, heatedat 100-150°C for 1 h at P=50 mm; evacuated to P=1 mm for 0.5 h, heated at 190-220°C; distd., IR, elem. anal.;99%
77-99-6

1,1,1-tri(hydroxymethyl)propane

C27H43N3O13

C87H137N9O39

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; acetonitrile at 20℃;99%
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

637-88-7

1,4-Cyclohexanedione

C18H32O6

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene at 90 - 112℃; for 10h; Reagent/catalyst; Solvent; Dean-Stark;98%
50-00-0

formaldehyd

77-99-6

1,1,1-tri(hydroxymethyl)propane

5187-23-5

5-ethyl-1,3-dioxane-5-methanol

Conditions
ConditionsYield
With cationite KU-2 In benzene Reflux; Dean-Stark;97%
With toluene-4-sulfonic acid In toluene for 4h; Heating;95%
With toluene-4-sulfonic acid In toluene for 4h; Heating;95%
With toluene-4-sulfonic acid In tetrahydrofuran for 3h; Reflux;93%
With toluene-4-sulfonic acid
77-99-6

1,1,1-tri(hydroxymethyl)propane

929-10-2

isooctanoic acid

C30H56O6

Conditions
ConditionsYield
With chlorosulfonic acid; 3,5-dichloro-2-hydroxybenzenesulfonyl chloride; 3-methylimidazoletrifluoromethanesulfonate; toluene-4-sulfonic acid In tetrahydrofuran; propan-1-ol at 200℃; for 10h; Temperature; Large scale;97%
77-99-6

1,1,1-tri(hydroxymethyl)propane

98-59-9

p-toluenesulfonyl chloride

A

C20H26O7S2

B

6962-93-2

2-ethyl-2-((tosyloxy)methyl)propane-1,3-diyl bis(4-methylbenzenesulfonate)

Conditions
ConditionsYield
With pyridine at -5 - 20℃; for 48h;A n/a
B 96.5%
111-20-6

1,10-decanedioic acid

77-99-6

1,1,1-tri(hydroxymethyl)propane

hydrogenated castor oil

hydrogenated castor oil

polymer, product of polycondensation of 2-ethyl-2-(hydroxymethyl)-1,3-propanediol, sebacic acid, and hydrogenated castor oil

polymer, product of polycondensation of 2-ethyl-2-(hydroxymethyl)-1,3-propanediol, sebacic acid, and hydrogenated castor oil

Conditions
ConditionsYield
With dibutyltin(II) dilaurate at 180 - 200℃;96.4%
77-99-6

1,1,1-tri(hydroxymethyl)propane

999-97-3

1,1,1,3,3,3-hexamethyl-disilazane

17940-81-7

tris((trimethylsiloxy)methyl)propane

Conditions
ConditionsYield
With activated clay at 60 - 70℃; for 3h;96.4%
77-99-6

1,1,1-tri(hydroxymethyl)propane

4-(1,3-diacetoxypropan-2-yloxy)-4-oxobutanoic acid

C39H56O24

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 0 - 25℃; for 24.5h;96%
77-99-6

1,1,1-tri(hydroxymethyl)propane

36239-09-5

ethyl chlorocarbonylacetate

O,O'-(2-(((3-ethoxy-3-oxopropanoyl)oxy)methyl)-2-ethylpropane-1,3-diyl) diethyl dimalonate

Conditions
ConditionsYield
With pyridine In tetrahydrofuran; dichloromethane at 20℃; for 12h;96%
77-99-6

1,1,1-tri(hydroxymethyl)propane

121-45-9

phosphorous acid trimethyl ester

756-79-6

dimethyl methane phosphonate

Conditions
ConditionsYield
Stage #1: 1,1,1-tri(hydroxymethyl)propane; phosphorous acid trimethyl ester at 80 - 120℃; for 4h;
Stage #2: With methyl p-toluene sulfonate at 170 - 180℃; for 2h; Reagent/catalyst; Temperature;
96%
77-99-6

1,1,1-tri(hydroxymethyl)propane

126-58-9

Dipentaerythritol

756-79-6

dimethyl methane phosphonate

121-45-9

phosphorous acid trimethyl ester

methyl-(5-ethyl-2-methyl-1,3,2-dioxaphosphorinan-5-yl)methyl methyl ester (P-oxide phosphonate)

Conditions
ConditionsYield
Stage #1: 1,1,1-tri(hydroxymethyl)propane; Dipentaerythritol; phosphorous acid trimethyl ester With phosphoric acid at 85℃; for 5h; Inert atmosphere;
Stage #2: dimethyl methane phosphonate With 1-bromo-butane at 185℃; for 16h;
95.8%
512-56-1

trimethyl phosphite

77-99-6

1,1,1-tri(hydroxymethyl)propane

102-85-2

tri-n-butyl phosphite

126-58-9

Dipentaerythritol

C13H25O10P3

Conditions
ConditionsYield
Stage #1: 1,1,1-tri(hydroxymethyl)propane; tri-n-butyl phosphite; Dipentaerythritol With sulfuric acid at 85℃; for 5h; Inert atmosphere;
Stage #2: trimethyl phosphite With 1-Bromopentane at 185℃; for 16h;
95.6%
77-99-6

1,1,1-tri(hydroxymethyl)propane

79-08-3

bromoacetic acid

343846-05-9

C12H17Br3O6

Conditions
ConditionsYield
With 2,6-di-tert-butyl-4-methyl-phenol; toluene-4-sulfonic acid In toluene for 7h; Reflux;95.1%
77-99-6

1,1,1-tri(hydroxymethyl)propane

C32H50O15S4

TMP-(S-S)3-G1-(acet)3

Conditions
ConditionsYield
With pyridine; dmap In dichloromethane at 0℃;95.1%
77-99-6

1,1,1-tri(hydroxymethyl)propane

382-21-8

perfluoroisobutylene

A

382-24-1

1,1,1,3,3,3-hexafluoro-2-trifluoromethyl-propane

B

97651-62-2

2-hexafluoroisopropylidene-5-ethyl-5--1,3-dioxane

Conditions
ConditionsYield
With potassium fluoride In acetonitrile 1) 0 deg C, 1 hour 2) 20 deg C, 11-12 h;A n/a
B 95%
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;

Trimethylol propane Chemical Properties

Molecule structure of Hexaglycerine (CAS NO.77-99-6):

IUPAC Name: 2-Ethyl-2-(hydroxymethyl)propane-1,3-diol
Molecular Formula: C6H14O3
Formula Weight: 134.17356 g/mol
Density: 1.116 g/cm
Melting Point: 56-58 °C(lit.)
Boiling Point: 295.7 °C at 760 mmHg 
Flash Point: 147.7 °C
Index of Refraction: 1.484
Molar Refractivity: 34.41 cm3
Molar Volume: 120.1 cm3
Surface Tension: 47.9 dyne/cm 
Enthalpy of Vaporization: 62.12 kJ/mol
Vapour Pressure: 0.000155 mmHg at 25 °C 
Solubility H2O: 0.1 g/mL, clear
XLogP3-AA: -0.8
H-Bond Donor: 3
H-Bond Acceptor: 3
Rotatable Bond Count: 4
Exact Mass: 134.094294
MonoIsotopic Mass: 134.094294
Topological Polar Surface Area: 60.7 
Canonical SMILES: CCC(CO)(CO)CO
InChI: InChI=1S/C6H14O3/c1-2-6(3-7,4-8)5-9/h7-9H,2-5H2,1H3
InChIKey: ZJCCRDAZUWHFQH-UHFFFAOYSA-N
EINECS: 201-074-9

Trimethylol propane Uses

 Hexaglycerine (CAS NO.77-99-6) is widely used in polyester and polyurethane foam production, but also for alkyd coatings, synthetic lubricants, plasticizers, surfactants, rosin esters and the manufacture of explosives.

Trimethylol propane Production

 N-butyraldehyde makes aldol reaction with formaldehyde under alkaline conditions, then desalting the concentrated reaction solution, then decoloring with the ion-exchange resin and purifying. At last, evaporating with the thin-film evaporator, cooling and rolling film, we can obtain Hexaglycerine .

Trimethylol propane Toxicity Data With Reference

1.    

orl-rat LD50:14,100 mg/kg

    HYSAAV    Hygiene and Sanitation: English Translation of Gigiena Sanitariya. 32 (5)(1967),288.
2.    

orl-mus LD50:13,700 mg/kg

    HYSAAV    Hygiene and Sanitation: English Translation of Gigiena Sanitariya. 32 (5)(1967),288.

Trimethylol propane Consensus Reports

Reported in EPA TSCA Inventory.

Trimethylol propane Safety Profile

Safety Statements: 22-24/25 
S22:Do not breathe dust. 
S24/25:Avoid contact with skin and eyes.
WGK Germany: 1
RTECS: TY6470000
HS Code: 29054100
Mildly toxic by ingestion. A combustible liquid. When heated to decomposition it emits acrid smoke and irritating vapors.

Trimethylol propane Specification

 Hexaglycerine (CAS NO.77-99-6) is also named as 1,1,1-Tri(hydroxymethyl)propane ; 1,1,1-Trimethylolpropane ; 1,1,1-Tris(hydroxymethyl)propane ; 1,3-Propanediol, 2-ethyl-2-(hydroxymethyl)- ; 2,2-Bis(hydroxymethyl)-1-butanol ; 2-Ethyl-2-(hydroxymethyl)propanediol ; 4-01-00-02786 (Beilstein Handbook Reference) ; AI3-24124 ; BRN 1698309 ; Ethriol ; Ethyltrimethylolmethane ; Etriol ; Ettriol ; HSDB 5218 ; Hexaglycerol ; Methanol, (propanetriyl)tris- ; NSC 3576 ; Propane, 1,1,1-tris(hydroxymethyl)- ; TMP ; TMP (VAN) ; TMP (alcohol) ; Tri(hydroxymethyl)propane ; Trimethylolpropane ; Tris(hydroxymethyl)propane ; UNII-090GDF4HBD . Hexaglycerine (CAS NO.77-99-6) is crystalline flakes. It is soluble in water, lower alcohol, glycerin, N, N-dimethylformamide, some soluble in acetone, ethyl acetate, slightly soluble in carbon tetrachloride, ether and chloroform, but insoluble in aliphatic hydrocarbons, Aromatic hydrocarbons and chlorinated hydrocarbons .

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