Trimethanolpropane
2-Ethyl-2-(hydroxymethyl)-1,3-propanediol
CAS: 77-99-6
Molecular Formula: C6H14O3
Trimethanolpropane - Names and Identifiers
Trimethanolpropane - Physico-chemical Properties
| Molecular Formula | C6H14O3 |
| Molar Mass | 134.17 |
| Density | 1.176 |
| Melting Point | 56-58°C(lit.) |
| Boling Point | 159-161°C2mm Hg(lit.) |
| Flash Point | 172 °C |
| Water Solubility | soluble |
| Solubility | H2O: 0.1g/mL, clear |
| Vapor Presure | <1 mm Hg ( 20 °C) |
| Vapor Density | 4.8 (vs air) |
| Appearance | White crystal |
| Color | White |
| BRN | 1698309 |
| pKa | 14.01±0.10(Predicted) |
| PH | 6.5 (100g/l, H2O, 20℃)(External MSDS) |
| Storage Condition | Store below +30°C. |
| Sensitive | Easily absorbing moisture |
| Explosive Limit | 2-11.8%(V) |
| Refractive Index | 1.4850 (estimate) |
| MDL | MFCD00004694 |
| Physical and Chemical Properties | Character: white patchy crystal. "use: TMP is intended for the manufacture of composite solid propellant charge coating and insulation layer, and can also be used for resin modifier and crosslinking agent. " |
| Use | TMP is intended for the manufacture of composite solid propellant charge coating and insulation layer, can also be used for resin modifier and crosslinking agent, is also the raw material of synthetic resin and used for the synthesis of aviation lubricating oil, plasticizer, etc |
Trimethanolpropane - Risk and Safety
| Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 1 |
| RTECS | TY6470000 |
| TSCA | Yes |
| HS Code | 29054100 |
| Toxicity | LD50 orally in Rabbit: > 2500 mg/kg |
Trimethanolpropane - Upstream Downstream Industry
| Raw Materials | Butyraldehyde Formaldehyde Formaldehyde |
| Downstream Products | Toluenediisocyanate Trihydroxymethylpropyl trioleate Polyurethane |
Trimethanolpropane - Reference
| Reference Show more | 1. Zhao Yanna, Lin Lei, cattle Yuhua, etc. Preparation and application of UV-resistant waterborne polyurethane sizing agent [J]. China paper, 38(9). 2. [IF = 1.813] Li Shaoxue et al."Tetrameethlpyrazine protection against Early Brain after Experimental sub-barachnoid haemorrhage by Affecting Mitochondrial-Dependent Caspase-3 Apoptotic Pathway."Evid-Based Compl Alt. 2017;2017:3514914 3. [IF=3.125] Jie Song et al."Preparation of humic acid water-retaining agent-modified polyurethane sponge as a soilless culture material."Journal Of Applied Polymer Science. 2022 Jan 28 |
Trimethanolpropane - Nature
Open Data Verified Data
White flaky crystals. Boiling point 295 °c. Melting point 58.8 °c. The relative density was 1. 0889. Flash point (Open Cup) 180 °c. Ignition point: 193 ℃. Heat of fusion 183 kJ/mol. The combustion heat was 3615kJ/mol. Soluble in water, low carbon alcohol, glycerol, N,N-methyl formamide, soluble in acetone, ethyl acetate, slightly soluble in carbon tetrachloride, ether and chloroform, but insoluble in aliphatic hydrocarbons, aromatic and chlorinated hydrocarbons. Its Hygroscopicity is about 50% of that of glycerol.
Last Update：2024-01-02 23:10:35
Trimethanolpropane - Preparation Method
Open Data Verified Data
n-butyraldehyde and formaldehyde in alkaline conditions of aldol condensation reaction. The reaction solution is concentrated to remove salt, then decolorized with ion exchange resin, purified, and finally evaporated by thin film evaporator, cooled and rolled.
Last Update：2022-01-01 10:34:47
Trimethanolpropane - Introduction
Soluble in acetone, soluble in carbon tetrachloride, chloroform, ether; insoluble in aliphatic hydrocarbons and aromatic hydrocarbons. It has strong hygroscopicity.
Last Update：2022-10-16 17:28:36
Trimethanolpropane - Use
Open Data Verified Data
is widely used in the production of polyester and polyurethane foams, but also in the manufacture of Alkyd Coatings, synthetic lubricants, plasticizers, surfactants, rosin esters and explosives. It can also be used directly as a heat stabilizer for Textile Auxiliaries and PVC resins.
Last Update：2022-01-01 10:34:46
Trimethanolpropane - Safety
Open Data Verified Data
- slightly toxic. The skin was non-irritating, and the LD50 in the rat test was 14.1g/kg.
- lined with plastic bags, external use of wood or iron drum packaging. Should be stored in a cool, dehumidifying, sunscreen, heat insulation and away from the fire. According to the general provisions of the storage and transportation of chemicals.
Last Update：2022-01-01 10:34:47
Trimethanolpropane - Reference Information
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Overview | the chemical name of trimethylolpropane (TMP) is 2-ethyl-2-hydroxymethyl-1, 3-propanediol, also known as trimethylol propane, 2, 2-dimethylol butanol, which has three typical hydroxymethyl groups on the molecule, and thus has polyol properties similar to glycerol, it can react with organic acids to produce monoesters or polyesters, react with aldehydes and ketones to produce acetals and ketals, and react with diisocyanates to produce carbamates, etc. It is a widely used chemical raw material and chemical product, mainly used in alkyd resin, polyurethane, unsaturated resin, polyester resin, coating and other fields, can also be used for the synthesis of aviation lubricating oil, plasticizer, surfactant, wetting agent, explosives, printing ink and so on, can also be directly used as textile auxiliaries and PVC resin heat stabilizer. |
| preparation method | 1. Cross-canizarro condensation method Cross-canizro condensation method is also called sodium formate method. N-butyraldehyde and formaldehyde aqueous solution in alkaline catalyst under the action of aldol condensation reaction to produce 2, 2-dimethylolbutyraldehyde, 2, 2-dimethylolbutanal is reacted with excess formaldehyde in strong alkali to form trimethylolpropane by cross-reaction, formaldehyde is oxidized to form formic acid, formic acid is neutralized with sodium hydroxide to form sodium formate, and the reaction mixture is desalted, qualified products were refined. The reaction equation is as follows: FIG. 1 is the reaction equation for the synthesis of TMP by cross-Canizaro condensation when trimethylolpropane is produced by this method, the catalysts used mainly include sodium hydroxide, calcium hydroxide, calcium oxide and organic tertiary amines (such as trimethylamine, triethylamine, etc.). When sodium hydroxide is used as the catalyst, the difficulty of the process increases when it dissolves in water and finally removes sodium formate. Therefore, the catalyst has been eliminated abroad, however, the catalyst is expensive, resulting in an increase in the production cost of trimethylolpropane; Calcium hydroxide (or calcium oxide) due to the solubility in water is small, most can be precipitated, the rest can be separated by centrifugal separation and membrane separation, and the separated calcium formate can be directly used for feed additives, preservatives, etc., which is convenient to use and has a good market, at present, most of the trimethylolpropane in foreign countries is produced by the catalyst. The cross-canizarol condensation method is a traditional method for producing trimethylolpropane. The method is relatively simple and easy to master, does not require high temperature, high pressure and special catalyst, and is more suitable for small and medium-scale industrial batch production. However, this method has many by-products, poor product quality and heavy post-treatment workload, and the yield of the product is only 60% ~ 70%. In order to reduce the formation of by-products, a large excess of formaldehyde (generally 8~10: 1 molar ratio) is needed to facilitate the complete reaction and inhibit the formation of some heat-sensitive substances that are difficult to separate, however, a large excess of formaldehyde increases the load of the post-treatment dealdehyde column and increases the energy consumption. In addition, the post-treatment of this process is relatively complicated, and 1t of Sodium Formate with low added value is produced per 1t of trimethylolpropane, As a result, the utilization rate of formaldehyde is very low, the production cost is increased, and the purification of trimethylolpropane is difficult. How to effectively remove formate is the key to prepare high quality trimethylolpropane. 2. Aldehyde hydrogenation reduction method The aldol condensation product 2, 2-dimethylolbutyraldehyde was obtained by the reaction of n-butanol and formaldehyde under the catalysis of trialkylamine (such as triethylamine), aqueous hydrogenation of 2, 2-dimethylolbutanal was carried out to produce trimethylolpropane. The reaction equation is as follows: FIG. 2 is the reaction equation for the synthesis of TMP by aldehyde hydrogenation and reduction in the condensation of aldol, triethylamine is mainly used as the catalyst, using triethylamine as the catalyst of aldol condensation reaction can control the selectivity of the reaction, inhibit the occurrence of side reactions and reduce the formation of formate. The aqueous hydrogenation catalyst is mainly nickel or nickel oxide distributed on the carrier, and copper chromite may also be used, and copper oxide or copper-chromium may be used as a cocatalyst. The aldehyde hydrogenation reduction method has high formaldehyde utilization rate, strong hydrogenation technology, can save a lot of formaldehyde and alkali, relatively few side reaction products, good product quality, simple purification and less equipment, the production cost is low, but the hydrogenation unit is required, the high pressure equipment is used, the hydrogenation equipment and the catalyst are required to be high, and the production technical requirements are also high, which is more suitable for large-scale continuous production. At present, some manufacturers of trimethylolpropane in Europe and the United States mainly use this method for production. |
| Application | 1. Synthesis of alkyd resin Because of the special molecular structure of trimethylolpropane molecule containing three primary hydroxyl groups, it can not only replace glycerol synthesis of alkyd resin, but also can replace or with neopentyl glycol, pentaerythritol and other Polyols to produce alkyd resin, its performance with glycerin, neopentyl glycol, pentaerythritol and other Polyols made of alkyd resin, has better hydrolysis resistance, oxidation stability, alkali resistance and thermal stability, in addition, it has the advantages of bright color, strong color retention, temperature resistance and fast drying, especially suitable for the production of road marking paint, finishing paint, can also be used as a car, refrigerator, washing machine, bicycle, aviation and marine finish, etc. The alkyd resin synthesized by trimethylolpropane has good compatibility with amino resin, and can be used as the raw material of polyurethane coating, and can also be used as urethane self-drying paint and drying paint and other high-grade coatings. 2. Synthesis of advanced lubricating oil esters of trimethylolpropane can be used for synthesis of advanced lubricating oil. The lubricating oil synthesized with trimethylolpropane as raw material has the advantages of low melting point, high viscosity, high ignition point and strong oxidation resistance. It is widely used in the lubrication of aircraft engines, and the working temperature can reach above 200 ℃, it can also be used for lubrication of automobile engines, air compressors and refrigerators, and its performance is better than that of lubricating oil synthesized from neopentyl glycol and other raw materials. In addition, the synthetic oil based on trimethylolpropane can also be used for the processing of bearing steel. 3. Production of polyester and polyurethane foams trimethylolpropane is widely used in the production of polyurethane elastomers and polyurethane foams. Trimethylolpropane and toluene diisocyanate (TDI), 1, 3-butanediol production of carbamate, with high hardness, good elasticity, wear and anti-aging advantages, widely used in solid tires, transport belt, manufacturing of sponge and thermal processing and aerospace industry; Polyether polyol with free hydroxyl group formed by the reaction of trimethylolpropane with ethylene oxide or propylene oxide is the main raw material for the production of flexible polyurethane foam, the synthetic polyurethane has the dual properties of rubber and plastic, has the characteristics of high elasticity, wear resistance, washing resistance, durability, fluorescence and bright color, and is especially suitable for the production of road marking paint, finishing paint, electrophoretic paint, etc, can also be used in the manufacture of aircraft, automobile, train, tire seat cushion, backrest, steering wheel, instrument, armrest, bumper, for the sole, solid tire, transmission belt, sponge, aerospace, thermal processing and building materials; Trimethylolpropane and glycerol maleic acid synthesis of polyester, with weatherability, radiation resistance, flexibility and reduce polyester self-dyeing characteristics, widely used as building materials and leather substitutes. In the production of foam, trihydroxymethylpropane may also be partially or fully substituted for 1, 4-butanediol. 4. Preparation of plasticizer In the presence of non-acidic catalyst, trimethylolpropane and mono aromatic acid, C5 ~ C9 fatty acid reaction of compound Ester, is a kind of good performance of plasticizer, the polymer with the ester has good high temperature resistance, hydrolysis resistance and acid and alkali resistance, and with polyvinyl chloride (PVC) it has good affinity, and the PVC plastic containing this plasticizer can still maintain good electrical insulation in a water environment. In addition, trimethylolpropane can also replace isodecyl alcohol for the production of important advanced plasticizer diisodecyl phthalate, used in the production of special coatings such as cable. 5. Preparation of emulsifier trimethylolpropane and mono fatty acid partial esterification with ethylene oxide reaction of semi-solid compounds, oil/water emulsion has a good emulsifying effect, can be used as pharmaceutical and cosmetic emulsifier. Nonionic surfactants prepared by the addition of trimethylolpropane and propylene oxide have excellent emulsifying properties and wettability. The alkyd resin made of trimethylolpropane and high molecular weight binary fatty acid containing two double bonds is a water/oil type emulsifier, which is widely used in textile and printing and dyeing industries. 6. Preparation of liquid fuel additive The liquid fuel additive was prepared by esterification of trimethylolpropane with oleic acid and then reacting with polyoxymethylene. The liquid fuel after adding 0.5% to 1% of the substance can purify the exhaust gas without using a vaporization device. 7. Production of trimethylolpropane triacrylate (TMPTA) trimethylolpropane triacrylate (TMPTA) obtained by the reaction of trimethylolpropane with acrylate is the most widely used multifunctional alkenyl Ester reactive diluent in the field of radiation curing, with high double bond content, fast curing, wear resistance, solvent resistance and other properties, mainly used for UV curable coatings and ink reactive diluent. Before irradiation with ultraviolet rays, a dilution effect is exerted, and after irradiation, it itself reacts to form a part of the cured film. TMPTA can also be used for the preparation of unsaturated polyester glass fiber reinforced plastic, reinforced plastics, special alkyd resin, adhesives, synthetic oil, rosin ester explosives, synthetic fiber additives and for the processing of chemical film. 8. Production of trimethylolpropane trimethacrylate (TMPTM) trimethylolpropane trimethacrylate (TMPTM) obtained by esterification of trimethylolpropane with methacrylic acid is a multi-functional monomer, it can be used for the setting of PVC latex (anti-corrosion rubber shoes, etc.) and cross-linking PVC coating line, and can also be used as anaerobic Binder, rubber (Ethylene Propylene Rubber) crosslinking agent and ink curing agent, it can also be used for the modification of coatings and resins. 9. Production of trimethylolpropane triglycidyl ester (TMPTE) trimethylolpropane and epichlorohydrin reaction of trimethylolpropane triglycidyl ester (TMPTE) can be used as reactive diluent of epoxy resin (epoxy resin coating), modifiers such as polyesters and melamine resins, fiber processing agents (anti-crease treatment agents), and adhesion modifiers. 10. The 43 flame retardant Polyether prepared by heating reaction of trimethylolpropane with phosphoric acid, vacuum dehydration, and then adding excess epichlorohydrin for polycondensation has excellent flame retardant properties, can react with isocyanate to produce flame retardant polyurethane resin; In addition, trimethylolpropane can also be used for resin chain extender, Textile Auxiliaries, curing agent, release agent, Catalyst, polyvinyl chloride (PVC) resin heat stabilizers and a variety of fine chemical synthesis, for the manufacture of sodium ion selective liquid membrane electrode. |
| Main references | [1] Ma Shichang, ed. A Dictionary of chemical substances. Xi'an: Shaanxi Science and Technology Press. 1999. Page 112. [2] Cui Xiaoming. Production, application and Market Overview of trimethylolpropane. Guizhou Chemical Industry Co., Ltd. 2003.28(2):11-15. |
| Use | used as a glycerol substitute and also used in the synthesis of drying oils widely used in the production of polyester and polyurethane foams, it is also used in the manufacture of Alkyd Coatings, synthetic lubricants, plasticizers, surfactants, rosin esters and explosives. Also directly used as a textile auxiliaries and PVC resin heat stability, in the application of alkyd resin, can improve the resin firmness, color, weather resistance, chemical resistance, sealing. TMP is intended for the manufacture of composite solid propellant charge coating and insulation layer, can also be used for resin modifier and crosslinking agent, is also the raw material of synthetic resin and used for the synthesis of aviation lubricating oil, plasticizers and the like molecule contains three hydroxymethyl groups at the-position, which is A new pentane structure of trihydric alcohol. It has the advantages of improving the resin firmness, corrosion resistance, sealing; Good stability for hydrolysis, pyrolysis and oxidation; Three hydroxyl groups have the same reaction and other excellent performance. used as a raw material of synthetic resin, also used in the synthesis of aviation lubricating oil, plasticizer, etc. |
| production method | n-butyl aldehyde and formaldehyde are subjected to aldol condensation reaction under alkaline conditions, and the reaction solution is concentrated to remove salt, then ion exchange resin decolorization, purification, and finally use thin film evaporator evaporation, cooling, rolling, to get the finished product. Raw material consumption quota: N-butyraldehyde (≥ 95%)950kg/t, formaldehyde (37%)3400kg/t. |
| category | flammable liquid |
| toxicity grade | low toxicity |
| Acute toxicity | oral-rat LD50: 14100 mg/kg; Oral-mouse LD50: 13700 mg/kg |
| flammability hazard characteristics | flammability; Combustion stimulus smoke |
| storage and transportation characteristics | warehouse ventilation and low temperature drying |
| extinguishing agent | dry powder, foam, sand, water |
| autoignition temperature | 375°C DIN 51794 |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 20:52:54
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