Trimethylolethane
Encyclopedia
Trimethylolethane is the organic compound
with the formula CH3C(CH2OH)3. This colorless solid is a triol
, that is it contains three hydroxy functional group
s. More specifically, it features three primary alcohol
groups in a compact neopentyl structure. Its esters are known for their resistance to heat, light, hydrolysis
, and oxidation. More important than TME and closely related is trimethylolpropane
(TMP).
of propionaldehyde
with formaldehyde
:
The second step entails a Cannizaro reaction:
A few thousand tons are produced annually in this way.
and polyester
resin
s, powder coating
resins, synthetic lubricant
s based on polyol esters, stabilizers
for plastics, plasticizer
s, and pigment coatings based on titanium dioxide
. Trimethylolethane based resins have superior weatherability and resistance to alkali and heat. Trimethylolethane is used in some phase change materials
. The typical composition is then 63 wt.% TME with 37 wt.% water. The mixture has melting point of 29.8 °C and heat of fusion 218 kJ/kg. Nitration
of trimethylolethane gives trimethylolethane trinitrate
, an explosive, monopropellant
, and energetic plasticizer.
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...
with the formula CH3C(CH2OH)3. This colorless solid is a triol
Triol
A triol is a chemical compound containing three hydroxyl groups , such as glycerol. An example of triol on benzene is benzenetriol.- See also :* Alcohols, chemical compounds with one hydroxyl group...
, that is it contains three hydroxy functional group
Functional group
In organic chemistry, functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. The same functional group will undergo the same or similar chemical reaction regardless of the size of the molecule it is a part of...
s. More specifically, it features three primary alcohol
Primary alcohol
A primary alcohol is an alcohol which has the hydroxyl radical connected to a primary carbon. It can also be defined as a molecule containing a “–CH2OH” group.Examples include ethanol and butanol....
groups in a compact neopentyl structure. Its esters are known for their resistance to heat, light, hydrolysis
Hydrolysis
Hydrolysis is a chemical reaction during which molecules of water are split into hydrogen cations and hydroxide anions in the process of a chemical mechanism. It is the type of reaction that is used to break down certain polymers, especially those made by condensation polymerization...
, and oxidation. More important than TME and closely related is trimethylolpropane
Trimethylolpropane
Trimethylolpropane is the organic compound with the formula CH3CH2C3. This colorless solid is a triol. Containing three hydroxy functional groups, TMP is a widely used building block in the polymer industry.-Production:...
(TMP).
Production
Trimethylolethane is produced via a two step process, starting with the condensation reactionCondensation reaction
A condensation reaction is a chemical reaction in which two molecules or moieties combine to form one single molecule, together with the loss of a small molecule. When this small molecule is water, it is known as a dehydration reaction; other possible small molecules lost are hydrogen chloride,...
of propionaldehyde
Propionaldehyde
Propionaldehyde or propanal is the organic compound with the formula CH3CH2CHO. It is a saturated 3-carbon aldehyde and is a structural isomer of acetone...
with formaldehyde
Formaldehyde
Formaldehyde is an organic compound with the formula CH2O. It is the simplest aldehyde, hence its systematic name methanal.Formaldehyde is a colorless gas with a characteristic pungent odor. It is an important precursor to many other chemical compounds, especially for polymers...
:
- CH3CH2CHO + 2 CH2O → CH3C(CH2OH)2CHO
The second step entails a Cannizaro reaction:
- CH3C(CH2OH)2CHO + CH2O + NaOH → CH3C(CH2OH)3 + NaO2CH
A few thousand tons are produced annually in this way.
Applications
TME is an intermediate in the production of alkydAlkyd
An alkyd is a polyester modified by the addition of fatty acids and other components. They are derived from polyols and a dicarboxylic acid or carboxylic acid anhydride. The term alkyd is a modification of the original name "alcid", reflecting the fact that they are derived from alcohol and...
and polyester
Polyester
Polyester is a category of polymers which contain the ester functional group in their main chain. Although there are many polyesters, the term "polyester" as a specific material most commonly refers to polyethylene terephthalate...
resin
Resin
Resin in the most specific use of the term is a hydrocarbon secretion of many plants, particularly coniferous trees. Resins are valued for their chemical properties and associated uses, such as the production of varnishes, adhesives, and food glazing agents; as an important source of raw materials...
s, powder coating
Powder coating
thumb|right|Aluminium extrusions being powder coatedPowder coating is a type of coating that is applied as a free-flowing, dry powder. The main difference between a conventional liquid paint and a powder coating is that the powder coating does not require a solvent to keep the binder and filler...
resins, synthetic lubricant
Synthetic oil
Synthetic oil is a lubricant consisting of chemical compounds that are artificially made . Synthetic lubricants can be manufactured using chemically modified petroleum components rather than whole crude oil, but can also be synthesized from other raw materials...
s based on polyol esters, stabilizers
Stabilizer (chemistry)
In chemistry a stabilizer is a chemical which tends to inhibit the reaction between two or more other chemicals. It can be thought of as the antonym to a catalyst...
for plastics, plasticizer
Plasticizer
Plasticizers or dispersants are additives that increase the plasticity or fluidity of the material to which they are added; these include plastics, cement, concrete, wallboard, and clay. Although the same compounds are often used for both plastics and concretes the desired effects and results are...
s, and pigment coatings based on titanium dioxide
Titanium dioxide
Titanium dioxide, also known as titanium oxide or titania, is the naturally occurring oxide of titanium, chemical formula . When used as a pigment, it is called titanium white, Pigment White 6, or CI 77891. Generally it comes in two different forms, rutile and anatase. It has a wide range of...
. Trimethylolethane based resins have superior weatherability and resistance to alkali and heat. Trimethylolethane is used in some phase change materials
Phase Change Material
A phase-change material is a substance with a high heat of fusion which, melting and solidifying at a certain temperature, is capable of storing and releasing large amounts of energy...
. The typical composition is then 63 wt.% TME with 37 wt.% water. The mixture has melting point of 29.8 °C and heat of fusion 218 kJ/kg. Nitration
Nitration
Nitration is a general chemical process for the introduction of a nitro group into a chemical compound. The dominant application of nitration is for the production of nitrobenzene, the precursor to methylene diphenyl diisocyanate...
of trimethylolethane gives trimethylolethane trinitrate
Trimethylolethane trinitrate
Trimethylolethane trinitrate , also known as metriol trinitrate or nitropentaglycerin, is a nitro ester. It is a high explosive similar to nitroglycerin. It is a transparent oily liquid, colorless to light brown. It is odorless. It is used in some solid propellants and smokeless powders as a...
, an explosive, monopropellant
Monopropellant
Monopropellants are propellants composed of chemicals or mixtures of chemicals which can be stored in a single container with some degree of safety. While stable under defined storage conditions, they react very rapidly under certain other conditions to produce a large volume of energetic gases...
, and energetic plasticizer.