Trimethylolpropane (TMP) is the
organic compound
Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...
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 an organic compound containing three hydroxyl groups ( functional groups),functional group
In organic chemistry, a functional group is any substituent or moiety (chemistry), moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions r ...
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 ...
of
butyraldehyde
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 an organic compound with the chemical formula and structure , more precisely . The compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde. It is stored as ...
:
:
The second step entails a
Cannizzaro 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 ...
resin
A resin is a solid or highly viscous liquid that can be converted into a polymer. Resins may be biological or synthetic in origin, but are typically harvested from plants. Resins are mixtures of organic compounds, predominantly terpenes. Commo ...
s. Otherwise,
acrylated and alkoxylated TMP's are used as multifunctional monomers to produce various coatings,
Ethoxylated
In organic chemistry, ethoxylation is a chemical reaction in which ethylene oxide () addition reaction, adds to a Substrate (chemistry), substrate. It is the most widely practiced alkoxylation, which involves the addition of epoxides to substrat ...
and propoxylated TMP, derived condensation of from TMP and the
epoxide
In organic chemistry, an epoxide is a cyclic ether, where the ether forms a three-atom ring: two atoms of carbon and one atom of oxygen. This triangular structure has substantial ring strain, making epoxides highly reactive, more so than other ...
s, are used for production of flexible
polyurethane
Polyurethane (; often abbreviated PUR and PU) is 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, polyurethane term ...
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 resin
An ion-exchange resin or ion-exchange polymer is a resin or polymer that acts as a medium for ion exchange, that is also known as an ionex. It is an solubility, insoluble matrix (or support structure) normally in the form of small (0.25–1.43&nbs ...
s. The
oxetane
Oxetane, or 1,3-propylene oxide, is a heterocycle, 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 compou ...
"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 miscibility, miscible with most p ...
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. The molecular structure can be described as a neopentane with one hydrogen atom in each methyl group replaced by a hydroxyl (–OH) group. It is therefore a polyol, specifically a ...
* 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 of ...
* 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 str ...
References
Triols
Alkanols