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. Th ...

with the formula CH₃CH₂C(CH₂OH)₃. This colourless to white solid with a faint odor is a triol. Containing three hydroxy

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 res ...

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 butanal 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 ...

: :CH₃CH₂CH₂CHO + 2 CH₂O → CH₃CH₂C(CH₂OH)₂CHO The second step entails a Cannizaro reaction: :CH₃CH₂C(CH₂OH)₂CHO + CH₂O + NaOH → CH₃CH₂C(CH₂OH)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

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 n ...

s. Otherwise, acrylated and alkoxylated TMP's are used as multifunctional monomers to produce various coatings,

Ethoxylated Ethoxylation is a chemical reaction in which ethylene oxide adds to a substrate. It is the most widely practiced alkoxylation, which involves the addition of epoxides to substrates. In the usual application, alcohols and phenols are converted in ...

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 ...

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 CH₃CH₂C(CH₂OCH₂CH=CH₂)_3-x(CH₂OH)_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. It is an insoluble matrix (or support structure) normally in the form of small (0.25–1.43 mm radius) microbeads, usually white or ...

s. The oxetane "TMPO" is a photoinduceable polymerisation initiator. It is may also be reacted with epichlorohydrin 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.

References

Triols

Production

Applications

See also

References