TRIMETHYLOLPROPANE TRIOLEATE

Trimethylolpropane Trioleate = TMPTO

Molecular Formula: CH3CH2C(CH2OOCC17H33)3
CAS No.: 11138-60-6
Molecular Weight 927.5141

Trimethylolpropane Trioleate or TMPTO is a biodegradable and hydrolytically stable polyol ester suitable for use in a wide range of applications.
With excellent lubricating property, high viscosity index, fire resistant and high biodegradability, TMPTO is ideal synthetic ester basic fluid for ISO 46 fire resistant hydraulic oil and ingredients for the formulation of steel milling, grinding, cutting oils, hot or cold rolling oils and drawing lubricants.

Trimethylolpropane Trioleate is used in industrial applications as lubricating base oil for hydraulic fluids, two-stroke engine oils, etc.
TMPTO is a biodegradable and hydrolytically stable polyol ester suitable for use in a wide range of applications.
With excellent lubricating property, high viscosity index, fire resistant and high biodegradability, TMPTO is ideal synthetic ester basic fluid for ISO 46 fire resistant hydraulic oil and ingredients for the formulation of steel milling, grinding, cutting oils, hot or cold rolling oils and drawing lubricants.
Trimethylolpropane Trioleate belongs to the fatty esters family and can be applied as base oil for the Lubricants industry

Trimethylolpropane trioleate (TMPTO) has been prepared by esterification of oleic acid with trimethylolpropane (TMP) without solvent in the presence of solid acid catalyst.
The synthesised TMPTO was characterised by infrared spectroscopy, and its physicochemical properties were also evaluated.
The compatibilities of TMPTO as lubricant base stock with several conventional additives for mineral oils were investigated.

The results showed that the synthesised TMPTO exhibited excellent viscosity–temperature property and low temperature fluidity, high flash point, good foaming stability, hydrolytic stability, and lubricity.
In addition, TMPTO possessed good compatibility with conventional additives designed for mineral oils.
In particular, zinc dialkyl dithiophosphates as extreme pressure and anti-wear additive exhibited good extreme pressure and anti-wear properties in TMPTO.

Features & Applications of Trimethylolpropane Trioleate:
Trimethylolpropane Trioleate has excellent lubricating properties,high viscosity index,fire resistances and high biodegradabilities.
TMPTO is an ideal base oil for ISO 46 fire resistant hydraulic oil (HFDU)and one ingredient for the formulation of biodegradable hydraulic oil,chain saw oil and water yacht engine oil
Trimethylolpropane Trioleate also recommended to be used as oiliness agent for liquid steel cold rolling system,steel tube drawing oil and other metal processing fluid

Afterward, five reaction parameters were investigated, and the optimal conditions obtained were as follows: catalyst/TMP, 3.2:1 (molar ratio) 2% (w/w) OA/TMP; temperature, 180 °C; reaction time, 3 h; and vacuum degree, 0.095 MPa.
Under the optimized conditions, the TMP conversion rate reached up to 92.8%.
Furthermore, TMPTO was confirmed by Fourier transform infrared spectroscopy (FTIR).
Finally, the typical properties of the product were evaluated, including the kinematic viscosity at 40 and 100 °C, viscosity index, solidifying point, and thermal oxidation stability of TMPTO.

Applications of Trimethylolpropane Trioleate:
Trimethylolpropane trioleate is used in biolubricant base oil, fire resistant & biodegradable hydraulic fluids, and metalworking fluids
Trimethylolpropane trioleate is particularly recommended for usage in formulation of environmentally-friendly hydraulic fluids and metalworking fluids.
Trimethylolpropane Trioleate is also used for cutting and forming (including steel rolling and greases).

Trimethylolpropane Trioleate or TMPTO is a biodegradable and hydrolytically stable polyol ester suitable for use in a wide range of applications.

KEYWORDS:
11138-60-6, TMPTO, 57675-44-2, UNII-S448BZW2BR, S448BZW2BR, EINECS 260-895-0, C60H110O6, Trimethylol propane orelate, SCHEMBL9724337, DTXSID4028044

Molecular Weight: 927.5
XLogP3-AA: 23.3
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 6
Rotatable Bond Count: 55
Exact Mass: 926.83024122
Monoisotopic Mass: 926.83024122
Topological Polar Surface Area: 78.9 Å²
Heavy Atom Count: 66
Formal Charge: 0
Complexity: 1000
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 3
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Trimethylolpropane trioleate is an ISO 46, biodegradable and hydrolytically stable polyol ester suitable for use in a wide range of applications, including HFDU type hydraulic fluids and environmentally acceptable lubricants,e.g., fibre auxiliary (spinning finish) .
Trimethylolpropane Trioleates product form is usually colorless or yellow clear liquid.
CAS:11138-60-6.

Trimethylolpropane trioleate (TMPTO) could significantly reduce environmental pollution compared to mineral oils.
In this study, oleic acid (OA) and trimethylolpropane (TMP) were used to synthesize TMPTO, and the synthesis process was optimized by single-factor experiments to obtain the highest yield.
First, two kinds of operating conditions (vacuum distillation and atmospheric reflux) were compared, and then four kinds of catalysts were investigated to select the most efficient catalyst in esterification.
Afterward, five reaction parameters were investigated, and the optimal conditions obtained were as follows: catalyst/TMP, 3.2:1 (molar ratio) 2% (w/w) OA/TMP; temperature, 180 °C; reaction time, 3 h; and vacuum degree, 0.095 MPa.

Under the optimized conditions, the TMP conversion rate reached up to 92.8%.
Furthermore, TMPTO was confirmed by Fourier transform infrared spectroscopy (FTIR).
Finally, the typical properties of the product were evaluated, including the kinematic viscosity at 40 and 100 °C, viscosity index, solidifying point, and thermal oxidation stability of TMPTO.

A chemical structure of a molecule includes the arrangement of atoms and the chemical bonds that hold the atoms together.
The Trimethylolpropane trioleate molecule contains a total of 175 bond(s).
There are 65 non-H bond(s), 6 multiple bond(s), 55 rotatable bond(s), 6 double bond(s) and 3 ester(s) (aliphatic).

The 2D chemical structure image of Trimethylolpropane trioleate is also called skeletal formula, which is the standard notation for organic molecules.
The carbon atoms in the chemical structure of Trimethylolpropane trioleate are implied to be located at the corner(s) and hydrogen atoms attached to carbon atoms are not indicated – each carbon atom is considered to be associated with enough hydrogen atoms to provide the carbon atom with four bonds.

The 3D chemical structure image of Trimethylolpropane trioleate is based on the ball-and-stick model which displays both the three-dimensional position of the atoms and the bonds between them.
The radius of the spheres is therefore smaller than the rod lengths in order to provide a clearer view of the atoms and bonds throughout the chemical structure model of Trimethylolpropane trioleate.

Item: Specifications
Appearance:    Colorless or yellow clear liquid
Viscosity (mm2/s):
40℃   45-55
100℃   9-10
Viscosity Index: 180-183
Acid Value (mg KOH/g): 1 Max
Flashing Point (open ℃): 290 Min
Pour Point (℃): -30 Max
Hydroxy Value (mg KOH/g): 10 Max
Saponification Value (mg KOH/g): 185-190

Applications of Trimethylolpropane trioleate：
With excellent lubricating property, high viscosity index, fire resistant and high biodegradability, TMPTO-A is an ideal synthetic ester basic fluid for ISO 46 fire resistant hydraulic oil ,and one ingredient for the formulation of biodegradable hydraulic oil, saw oil , barge engine oil.
TMPTO-B,TMPTO-C are recommended as high effective oiliness additive for cold steel rolling oil, pipe drawing oil,metal cutting fluids and other metal processing fluids.

Trimethylolpropane trioleate was synthesized by oleic acid and trimethylolpropane as the raw material, SnCl 2 ·2H 2 O as catalyst, toluene as watercarrying.
The optimum reaction condition obtained through the experiments were found as follows: the molar ratio of OA to TMP was 3.1:1, the amount of SnCl 2 ·2H 2 O was 2%, with toluene 2ml, reacted for 2h at temperature 170°C and vacuum degree 0.07Mpa.
The results show that in the optimum conditions, the AE value of emulsification-resistive was 438.81, the ester value was 91.65%, the acid value was 2.41mgKOH/g, according with the standard of GB/T264.
The structure of product was identified by IR.

Description of Trimethylolpropane trioleate:
A liquid, easy to handle, highly efficient thickening agent for surfactant rinse off formulations and especially suitable for difficult to thicken formulas that do not contain sulfate-based surfactants.
Effective even at low surfactant concentrations.
Trimethylolpropane trioleate is Cold Processable.
Improves viscosity &stability at higher temperatures (pearlized systems).
Recommended alternative to DEA/MEA-containing thickeners.

Iupac Name:
2,2-bis{[(9Z)-9-octadecenoyloxy]methyl}butyl (9Z)-9-octadecenoate

Inchi Code:
1S/C60H110O6/c1-5-9-12-15-18-21-24-27-30-33-36-39-42-45-48-51-57(61)64-54-60(8-4,55-65-58(62)52-49-46-43-40-37-34-31-28-25-22-19-16-13-10-6-2)56-66-59(63)53-50-47-44-41-38-35-32-29-26-23-20-17-14-11-7-3/h27-32H,5-26,33-56H2,1-4H3/b30-27-,31-28-,32-29-

InChI key:
BTGGRPUPMPLZNT-PGEUSFDPSA-N

CHEMICAL COMPOSITION:
Trimethylolpropane TriOleate CHARACTERISTICS ESTEROL 332 is a pale yellow to amber viscous liquid with a bland fatty odour.

Product Usage of Trimethylolpropane trioleate:
Lubricants: Oxidatively stable vegetable oil based synthetic ester which can be used as the basis of non-toxic, biodegradable lubricant products such as hydraulic fluids.
Metal Working: Component of metal working formulations with high temperature stability.

Key Points of Trimethylolpropane trioleate:
Readily Biodegradable means that Trimethylolpropane trioleate will have a low environmental impact.
Non-toxic means that Trimethylolpropane trioleate poses a low health and safety risk for users.
Excellent oxidative and temperature stability for use in high temperature situations.

Evaluation and Testing:
-Moisture: 0.1%
-Colour: 4 Gardner
-SG (20ºC): 0.93
-Acid Value: 1
-Saponification Value: 180
-Hydroxyl Value: 20
-Flash Point (CC): 250ºC

CAS No: 57675-44-2
Product Code: FT140388
MDL No: MFCD00072630
Chemical Formula: C60H110O6
Molecular Weight: 927.51 g/mol

Trimethylolpropane trioleate
57675-44-2
UNII-S448BZW2BR
9-Octadecenoic acid (9Z)-, 2-ethyl-2-[[[(9Z)-1-oxo-9-octadecenyl]oxy]methyl]-1,3-propanediyl ester
2,2-bis[[(Z)-octadec-9-enoyl]oxymethyl]butyl (Z)-octadec-9-enoate
S448BZW2BR
2-ethyl-2-[[(1-oxooleyl)oxy]methyl]-1,3-propanediyl dioleate
2-Ethyl-2-(((1-oxooleyl)oxy)methyl)-1,3-propanediyl dioleate
9-Octadecenoic acid (9Z)-, 2-ethyl-2-((((9Z)-1-oxo-9-octadecenyl)oxy)methyl)-1,3-propanediyl ester
2,2-bis{[(9Z)-octadec-9-enoyloxy]methyl}butyl (9Z)-octadec-9-enoate
EINECS 260-895-0
C60H110O6
Trimethylol propane orelate
SCHEMBL9724337
DTXSID4028044
9-Octadecenoic acid (9Z)-, 1,1'-(2-ethyl-2-((((9Z)-1-oxo-9-octadecen-1-yl)oxy)methyl)-1,3-propanediyl) ester
MFCD00072630
ZINC150339507
Trimethylolpropane Trioleate, veg. based
BS-28916
Z4903
2-Ethyl-2-(hydroxymethyl)-1,3-propanediol trioleate
Q27288562
2,2-BIS({[(9Z)-OCTADEC-9-ENOYLOXY]METHYL})BUTYL (9Z)-OCTADEC-9-ENOATE
9-Octadecenoic acid (Z)-, 2-ethyl-2-(((1-oxo-9-octadecenyl)oxy)methyl)-1,3-propanediyl ester, (Z)-
2-ethyl-2-(((1-oxooleyl)oxy)methyl)-1,3-propane diyl dioleate
2-ethyl-2-(((1-oxooleyl)oxy)methyl)-1,3-propanediyl dioleate
2-ethyl-2-[[(1-oxooleyl)oxy]methyl]-1,3-propanediyl dioleate
2,2-bis[[(Z)- octadec-9-enoyl]oxymethyl]butyl (Z)-octadec-9-enoate
2,2-bis{[(9Z)-octadec-9-enoyloxy]methyl}butyl (9Z)-octadec-9-enoate
9-octadecenoic acid (9Z)-, 2-ethyl-2-((((9Z)-1-oxo-9-octadecenyl)oxy)methyl)-1,3-propanediyl ester
9-octadecenoic acid (9Z)-, 2-ethyl-2-[[[(9Z)-1-oxo-9-octadecenyl]oxy]methyl]-1,3-propanediyl ester
9-octadecenoic acid (Z)-, 2-ethyl-2-(((1-oxo-9-octadecenyl)oxy)methyl)-1,3-propanediyl ester, (Z)-
9-octadecenoic acid, 2,2-bis[[[(9Z)-1-oxo-9-octadecen-1-yl]oxy]methyl]butyl ester, (9Z)-
2,2-bis{[(9Z)-9-octadecenoyloxy]methyl}butyl (9Z)-9-octadecenoate
trimethylol propane trioleate
(9Z)-9-Octadécénoate de 2,2-bis{[(9Z)-9-octadecenoyloxy]méthyl}butyle [French] [ACD/IUPAC Name]
2,2-BIS({[(9Z)-OCTADEC-9-ENOYLOXY]METHYL})BUTYL (9Z)-OCTADEC-9-ENOATE
2,2-Bis{[(9Z)-9-octadecenoyloxy]methyl}butyl (9Z)-9-octadecenoate [ACD/IUPAC Name]
2,2-Bis{[(9Z)-9-octadecenoyloxy]methyl}butyl-(9Z)-9-octadecenoat [German] [ACD/IUPAC Name]
2,2-Bis{[(9Z)-octadec-9-enoyloxy]methyl}butyl (9Z)-octadec-9-enoate
2,2-bis{[(9Z)-octadec-9-enoyloxy]methyl}butyl (9Z)-octadec-9-enoate (non-preferred name)
260-895-0 [EINECS]
2-Ethyl-2-(((1-oxooleyl)oxy)methyl)-1,3-propanediyl dioleate
57675-44-2 [RN]
9-Octadecenoic acid (9Z)-, 2-ethyl-2-[[[(9Z)-1-oxo-9-octadecenyl]oxy]methyl]-1,3-propanediyl ester
9-octadecenoic acid, 2,2-bis[[[(9Z)-1-oxo-9-octadecen-1-yl]oxy]methyl]butyl ester, (9Z)-
TRIMETHYLOLPROPANE TRIOLEATE
(Z)-2-Ethyl-2-((oleoyloxy)methyl)propane-1,3-diyldioleate
[57675-44-2]
2,2-bis[[(Z)-octadec-9-enoyl]oxymethyl]butyl (Z)-octadec-9-enoate
2-Ethyl-2-(hydroxymethyl)-1,3-propanediol trioleate
2-ethyl-2-[[(1-oxooleyl)oxy]methyl]-1,3-propanediyl dioleate
9-Octadecenoic acid (9Z)-, 2-ethyl-2-((((9Z)-1-oxo-9-octadecenyl)oxy)methyl)-1,3-propanediyl ester
9-Octadecenoic acid (Z)-, 2-ethyl-2-(((1-oxo-9-octadecenyl)oxy)methyl)-1,3-propanediyl ester, (Z)-
AC1O5M6W
MFCD00072630 [MDL number]
SCHEMBL9724337
Trimethylolpropane Trioleate, veg. based