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77-99-6

Basic Information
CAS No.: 77-99-6
Name: Trimethylol propane
Article Data: 50
Cas Database
Molecular Structure:
Molecular Structure of 77-99-6 (Trimethylol propane)
Formula: C6H14O3
Molecular Weight: 134.175
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;
EINECS: 201-074-9
Density: 1.116 g/cm3
Melting Point: 56-58 °C(lit.)
Boiling Point: 295.7 °C at 760 mmHg
Flash Point: 147.7 °C
Solubility: soluble in water
Appearance: white crystalline flakes
Hazard Symbols: N/A
Risk Codes: N/A
Safety: 22-24/25
Transport Information: N/A
PSA: 60.69000
LogP: -0.64030
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
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Chemistry

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

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.

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 .

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.

Consensus Reports

Reported in EPA TSCA Inventory.

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.

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 .