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Trimethylolpropane (TMP) is the organic compound with the formula CH3CH2C(CH2OH)3.
Trimethylolpropane (TMP) is a Colorless, hygroscopic crystals soluble in water and alcohol.
Trimethylolpropane (TMP), in the form of a clear crystalline flake, is an alcohol produced by the reaction of formaldehyde with n-butyraldehyde.
CAS Number: 77-99-6
Molecular Formula: C6H14O3
Molecular Weight: 134.17
EINECS Number: 201-074-9
Synonyms: 1,1,1-TRIS(HYDROXYMETHYL)PROPANE, DIST.;TrimethanolPropane;1,3-Propanediol, 2-ethyl-2-(hydroxymethyl)-;Trimethylol;Abbreviation;propylidynetrimethanol;Trimethylolpropane (TMP), carbamate with tolylene diisocyanate solution;Trimethyloy propane
Trimethylolpropane (TMP) is used as a precursor for the manufacture of resins including alkyds, saturated polyesters and polyurethanes (polyester polyol and polycarbonate diol).
This colourless to white solid with a faint odor is a triol.
The three primary hydroxyl groups undergo the normal OH group reactions.
Trimethylolpropane (TMP) is a primary alcohol.
Containing three hydroxy functional groups, Trimethylolpropane (TMP) is a widely used building block in the polymer industry.
Trimethylolpropane (TMP) is produced via a two step process, starting with the condensation of butyraldehyde with formaldehyde: CH3CH2CH2CHO + 2 CH2O → CH3CH2C(CH2OH)2CHO
The second step entails a Cannizzaro reaction: CH3CH2C(CH2OH)2CHO + CH2O + NaOH → CH3CH2C(CH2OH)3 + NaO2CH
Approximately 200,000,000 kg are produced annually in this way.
Trimethylolpropane (TMP) is an intermediate and a triol that can be used in glues and polyurethane coatings.
It is also known as hexaglycerol.
Trimethylolpropane (TMP) is a polyfunctional alcohol composed of a propane backbone bearing three hydroxyl groups, which gives it high reactivity and strong hydrogen-bonding capability.
Trimethylolpropane (TMP) appears as a white to off-white crystalline solid and is valued for its chemical stability and well-defined molecular structure.
The presence of three primary hydroxyl groups makes it an important building block in many condensation and esterification reactions.
Because of its trifunctional nature, Trimethylolpropane (TMP) readily forms branched and crosslinked molecular structures when reacted with acids, isocyanates, or other reactive compounds.
This allows it to impart rigidity, thermal stability, and resistance to degradation in the resulting materials.
Its compact molecular size also helps maintain good processability while still enabling high crosslink density.
Trimethylolpropane (TMP) exhibits good thermal resistance and low volatility, which supports its use in high-temperature and long-life applications.
Trimethylolpropane (TMP) shows good compatibility with a wide range of organic compounds and polymers.
These physical characteristics make it suitable for demanding industrial formulations.
In materials science, Trimethylolpropane (TMP) is especially valued for its ability to improve mechanical strength and chemical resistance.
Its incorporation into polymer networks often leads to enhanced hardness and durability.
At the same time, it allows controlled tuning of flexibility depending on formulation design.
From a chemical standpoint, Trimethylolpropane (TMP) is considered a versatile intermediate because its three hydroxyl groups can be selectively modified.
This enables the synthesis of a wide variety of derivatives with tailored properties.
Such versatility explains its broad importance across coatings, resins, lubricants, and advanced material systems.
Trimethylolpropane (TMP) contributes to improved thermal and mechanical balance in polymer systems because it increases crosslink density without making materials excessively brittle.
This balance allows materials to retain strength while still tolerating mechanical stress and deformation.
Such behavior is particularly important in coatings and resins exposed to cyclic loads.
In ester chemistry, Trimethylolpropane (TMP) is frequently used to produce TMP esters with controlled branching and high purity.
These esters exhibit excellent oxidative stability and low volatility compared to linear ester analogues.
This makes them suitable for demanding thermal and oxidative environments.
Trimethylolpropane (TMP) also enhances chemical resistance in finished materials by reducing the number of weak points in polymer chains.
Its trifunctional structure limits chain mobility and solvent penetration.
As a result, materials derived from it often show improved resistance to oils, fuels, and chemicals.
Melting point: 56–58 °C (lit.)
Boiling point: 159–161 °C at 2 mm Hg (lit.)
Density: 1.176
Bulk density: 700 kg/m³
Vapor density: 4.8 (vs air)
Vapor pressure: <1 mm Hg at 20 °C
Refractive index: 1.4850 (estimate)
Flash point: 172 °C
Storage temp.: Store below +30 °C
Solubility: H₂O, 0.1 g/mL, clear
pKa: 14.01 ± 0.10 (predicted)
Form: Flakes
Color: White
pH: 6.5 (100 g/L, H₂O, 20 °C; external MSDS)
Explosive limit: 2–11.8 % (v/v)
Water solubility: Soluble
BRN: 1698309
Cosmetics ingredients functions: Humectant; Solvent
InChIKey: ZJCCRDAZUWHFQH-UHFFFAOYSA-N
LogP: −0.975 (estimated)
Trimethylolpropane (TMP) is made by the base-catalyzed aldol addition of butyraldehyde with formaldehyde followed by Cannizzaro reaction of the intermediate 2,2-bis(hydroxymethyl) butanal with additional formaldehyde and at least a stoichiometric quantity of base.
Trimethylolpropane (TMP) provides a compact and symmetrical molecular framework that contributes to uniform network formation in polymers.
This symmetry helps distribute stress evenly throughout cured materials.
As a result, products formulated with it often show improved dimensional stability.
In reactive formulations, Trimethylolpropane (TMP) acts as an efficient crosslinking center due to the close proximity of its hydroxyl groups.
This promotes rapid and controlled reaction kinetics during curing or polymerization.
Such behavior is advantageous in processes that require predictable and reproducible material properties.
The molecule demonstrates good resistance to hydrolysis and oxidative degradation under normal service conditions.
This stability supports long-term performance in materials exposed to heat, moisture, or chemicals.
Trimethylolpropane (TMP) is therefore suitable for applications demanding extended service life.
Trimethylolpropane (TMP) also influences viscosity and flow behavior during processing.
Its solid state and defined melting behavior allow precise control during blending and formulation.
This contributes to consistent manufacturing quality in industrial-scale production.
From a structural standpoint, Trimethylolpropane (TMP) enables the formation of highly branched architectures without excessive molecular weight increase.
This allows designers to balance hardness and toughness within the same material system.
Such control is important in advanced polymer engineering.
Because of its predictable reactivity, Trimethylolpropane (TMP) is often used as a reference polyol in research and development.
It allows systematic investigation of structure–property relationships in crosslinked materials.
This role highlights its importance not only in industry but also in scientific studies.
Various procedures have been suggested for separating the Trimethylolpropane (TMP) from the formate.
For instance, the concentrated reaction solution can be extracted with an organic solvent, which is then evaporated and the crude Trimethylolpropane (TMP) is purifified by vacuum distillation.
In another variant, the aqueous reaction solution is evaporated until most of the sodium formate crystallizes and is removed by hot fifiltration.
The application of electrodialysis has also been suggested.
The liquid Trimethylolpropane (TMP) which remains is liberated of residual salts with an ion exchanger and then distilled.
The removal of discoloring impurities is described in.
Cyclic diethers of the acetal type (1,3-dioxanes, formals) can be converted into Trimethylolpropane (TMP) and methanol by metal-catalyzed hydrogenation.
Removal of high boiling acetals by acid treatment has been described.
During processing, Trimethylolpropane (TMP) allows formulators to fine-tune curing speed and final hardness by adjusting stoichiometry.
Small changes in its concentration can significantly influence network structure.
This sensitivity provides high formulation flexibility for customized material performance.
In composite and reinforced systems, Trimethylolpropane (TMP) supports strong interfacial bonding between matrix and filler.
Its multiple hydroxyl groups promote better wetting and chemical interaction.
This leads to improved load transfer and mechanical integrity in composite materials.
Because of its reproducible quality and well-characterized behavior, Trimethylolpropane (TMP) is widely used in standard industrial formulations.
It provides consistency across batches and production scales.
This reliability is a key reason for its continued and widespread use in advanced material technologies.
Uses:
Trimethylolpropane (TMP) acts as a precursor to alkyd resins, high-gloss coatings and ion exchange resins.
It is also employed as a multifunctional monomer utilized for the production of coatings, ethoxylated and propoxylated Trimethylolpropane (TMP) derivatives.
Further, it serves as a building block in the polymer industry.
Trimethylolpropane (TMP) is widely used as a polyol in the manufacture of alkyd resins, polyester resins, and polyurethane systems.
Its trifunctional structure allows the formation of branched and crosslinked networks that provide strength, hardness, and durability.
These materials are commonly applied in industrial coatings, paints, and varnishes.
In lubricant technology, Trimethylolpropane (TMP) is used to produce synthetic ester base oils known as TMP esters.
These esters exhibit excellent thermal stability, low volatility, and strong resistance to oxidation.
They are used in high-performance lubricants for automotive, aviation, and industrial machinery.
Trimethylolpropane (TMP) is also applied in the production of radiation-curable and thermosetting resins.
It helps control crosslink density and curing behavior.
This supports its use in UV-curable coatings, inks, and adhesives.
In adhesive and sealant formulations, Trimethylolpropane (TMP) improves mechanical strength, chemical resistance, and long-term durability.
It contributes to strong bonding performance under thermal and environmental stress.
These properties make it suitable for structural and industrial adhesive systems.
Trimethylolpropane (TMP) is used in plastic and composite formulations to enhance rigidity and dimensional stability.
It supports uniform stress distribution and resistance to deformation.
Such applications are common in molded components and reinforced materials.
In research and development, Trimethylolpropane (TMP) serves as a reference polyol for studying crosslinking and network formation.
Its predictable reactivity enables systematic formulation design.
This use supports innovation in advanced polymer and materials science.
Trimethylolpropane (TMP) is used in saturated polyesters for coil coatings, alkyds for paints, polyurethanes for coatings and elastomers, acrylic acid esters for radiation curing, esters for synthetic lubricants, rosin esters and for surface treatment of pigments.
Large quantities of Trimethylolpropane (TMP) and its ethoxylated derivatives are used as precursors for urethanes and polyester resins. Another important field of application is in medium-oil and short-oil alkyd resins (→ Alkyd Resins). The resulting lacquers are characterized by excellent resistance to alkali, detergents, and water, combined with outstanding impact resistance and flexibility, as well as excellent clearness and clearness retention.
Trimethylolpropane (TMP) is mainly consumed as a precursor to alkyd resins. Otherwise, acrylated and alkoxylated TMP's are used as multifunctional monomers to produce various coatings, Ethoxylated and propoxylated TMP, derived condensation of from TMP and the epoxides, are used for production of flexible polyurethanes.
Allyl ether derivatives of TMP, with the formula CH3CH2C(CH2OCH2CH=CH2)3-x(CH2OH)x are precursors to high-gloss coatings and ion exchange resins.
The oxetane "TMPO" is a photoinduceable polymerisation initiator.
Trimethylolpropane (TMP) is may also be reacted with epichlorohydrin to produce the triglycidyl ether.
Safety Profile:
Trimethylolpropane (TMP) may cause mild irritation to the skin and eyes upon direct contact, especially with prolonged or repeated exposure.
Contact can lead to redness, dryness, or discomfort due to interaction with skin moisture.
The use of protective gloves and eye protection is recommended during handling.
Inhalation of dust particles may cause irritation to the respiratory tract.
This risk is mainly associated with handling the solid material during weighing, grinding, or transfer operations.
Adequate ventilation and dust control measures help reduce inhalation exposure.
Ingestion of Trimethylolpropane (TMP) in significant amounts may cause gastrointestinal discomfort such as nausea or irritation.
The substance is generally considered to have low acute toxicity.
Nevertheless, good laboratory and industrial hygiene practices should be followed to prevent accidental ingestion.
From a safety perspective, Trimethylolpropane (TMP) is chemically stable and not highly flammable under normal conditions.
However, it can decompose at elevated temperatures, producing irritating fumes.
Proper temperature control and storage away from strong oxidizing agents are advised.
