Trimethylolpropane (TMP) is the
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...
with the formula CH
3CH
2C(CH
2OH)
3. This colourless to white solid with a faint odor is a
triol
In chemistry, a triol is a chemical compound containing three hydroxyl groups ( functional groups),functional group
In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest ...
s, TMP is a widely used building block in the polymer industry.
Production
TMP is produced via a two step process, starting with the
condensation
Condensation is the change of the state of matter from the gas phase into the liquid phase, and is the reverse of vaporization. The word most often refers to the water cycle. It can also be defined as the change in the state of water vapor to ...
of
butanal
Butyraldehyde, also known as butanal, is an organic compound with the formula CH3(CH2)2CHO. This compound is the aldehyde derivative of butane. It is a colorless flammable liquid with an unpleasant smell. It is miscible with most organic solvents. ...
with
formaldehyde
Formaldehyde ( , ) (systematic name methanal) is a naturally occurring organic compound with the formula and structure . The pure compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde (refer to section F ...
:
:CH
3CH
2CH
2CHO + 2 CH
2O → CH
3CH
2C(CH
2OH)
2CHO
The second step entails a
Cannizaro reaction
The Cannizzaro reaction, named after its discoverer Stanislao Cannizzaro, is a chemical reaction which involves the base-induced disproportionation of two molecules of a non-enolizable aldehyde to give a primary alcohol and a carboxylic acid.
...
:
:CH
3CH
2C(CH
2OH)
2CHO + CH
2O + NaOH → CH
3CH
2C(CH
2OH)
3 +
NaO2CH
Approximately 200,000,000 kg are produced annually in this way.
[Peter Werle, Marcus Morawietz, Stefan Lundmark, Kent Sörensen, Esko Karvinen, Juha Lehtonen “Alcohols, Polyhydric” in Ullmann’s Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2008.]
Applications
TMP is mainly consumed as a precursor to
alkyd
An alkyd is a polyester resin modified by the addition of fatty acids and other components. Alkyds are derived from polyols and organic acids including dicarboxylic acids or carboxylic acid anhydride and triglyceride oils. The term ''alkyd'' is a m ...
resin
In polymer chemistry and materials science, resin is a solid or highly viscous substance of plant or synthetic origin that is typically convertible into polymers. Resins are usually mixtures of organic compounds. This article focuses on natu ...
s. 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
epoxide
In organic chemistry, an epoxide is a cyclic ether () with a three-atom ring. This ring approximates an equilateral triangle, which makes it strained, and hence highly reactive, more so than other ethers. They are produced on a large scale for ...
s, are used for production of flexible
polyurethane
Polyurethane (; often abbreviated PUR and PU) refers to a class of polymers composed of organic chemistry, organic units joined by carbamate (urethane) links. In contrast to other common polymers such as polyethylene and polystyrene, polyurethan ...
s. Allyl ether derivatives of TMP, with the formula CH
3CH
2C(CH
2OCH
2CH=CH
2)
3-x(CH
2OH)
x are precursors to high-gloss coatings and
ion exchange resins. The
oxetane
Oxetane, or 1,3-propylene oxide, is a heterocyclic organic compound with the molecular formula , having a four-membered ring with three carbon atoms and one oxygen atom.
The term "an oxetane" or "oxetanes" refer to any organic compound containing ...
"TMPO" is a photoinduceable polymerisation initiator.
[ It is may also be reacted with ]epichlorohydrin
Epichlorohydrin (abbreviated ECH) is an organochlorine compound and an epoxide. Despite its name, it is not a halohydrin. It is a colorless liquid with a pungent, garlic-like odor, moderately soluble in water, but miscible with most polar organi ...
to produce the triglycidyl ether.[{{Cite patent, country=US, number=5162547, title=Process for the preparation of glycidyl ethers, pubdate=1992-11-10, inventor1-last=Roth, inventor1-first=Martin, inventor2-last=Wolleb, inventor2-first=Heinz, inventor3-last=Truffer, inventor3-first=Marc-Andre, assign1= Ciba-Geigy Corp.]
See also
* Pentaerythritol
Pentaerythritol is an organic compound with the formula C(CH2OH)4. Classified as a polyol, it is a white solid. Pentaerythritol is a building block for the synthesis and production of explosives, plastics, paints, appliances, cosmetics, and many o ...
* Neopentyl glycol
Neopentyl glycol (IUPAC name: 2,2-dimethylpropane-1,3-diol) is an organic chemical compound. It is used in the synthesis of polyesters, paints, lubricants, and plasticizers. When used in the manufacture of polyesters, it enhances the stability ...
* Trimethylolethane
Trimethylolethane (TME) is the organic compound with the formula CH3C(CH2OH)3. This colorless solid is a triol, as it contains three hydroxy functional groups. More specifically, it features three primary alcohol groups in a compact neopentyl st ...
References
Triols