Dibutyl maleate is an
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. T ...
with the formula (CHCO
2Bu)
2 (Bu =
butyl
In organic chemistry, butyl is a four- carbon alkyl radical or substituent group with general chemical formula , derived from either of the two isomers (''n''-butane and isobutane) of butane.
The isomer ''n''-butane can connect in two ways, gi ...
). It is the
diester
In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides a ...
of the unsaturated dicarboxylic acid
maleic acid
Maleic acid or ''cis''-butenedioic acid is an organic compound that is a dicarboxylic acid, a molecule with two carboxyl groups. Its chemical formula is HO2CCH=CHCO2H. Maleic acid is the ''cis''-isomer of butenedioic acid, whereas fumaric ac ...
. It is a colorless oily liquid, although impure samples can appear yellow.
Preparation
Dibutyl maleate can be prepared by the reaction of
maleic acid anhydride and
1-butanol
1-Butanol, also known as butan-1-ol or ''n''-butanol, is a primary alcohol with the chemical formula C4H9OH and a linear structure. Isomers of 1-butanol are isobutanol, butan-2-ol and ''tert''-butanol. The unmodified term butanol usually refers ...
in presence of
p-toluenesulfonic acid
''p''-Toluenesulfonic acid (PTSA or ''p''TsOH) or tosylic acid (TsOH) is an organic compound with the formula CH3 C6H4 SO3H. It is a white extremely hygroscopic solid that is soluble in water, alcohols, and other polar organic solvents. The CH3C ...
.
Uses
Dibutyl maleate is mainly used as a
plasticizer
A plasticizer ( UK: plasticiser) is a substance that is added to a material to make it softer and more flexible, to increase its plasticity, to decrease its viscosity, and/or to decrease friction during its handling in manufacture.
Plasticiz ...
for aqueous
dispersion
Dispersion may refer to:
Economics and finance
* Dispersion (finance), a measure for the statistical distribution of portfolio returns
* Price dispersion, a variation in prices across sellers of the same item
*Wage dispersion, the amount of variat ...
s of
copolymer
In polymer chemistry, a copolymer is a polymer derived from more than one species of monomer. The polymerization of monomers into copolymers is called copolymerization. Copolymers obtained from the copolymerization of two monomer species are some ...
s with
vinyl acetate
Vinyl acetate is an organic compound with the formula CH3CO2CH=CH2. This colorless liquid is the precursor to polyvinyl acetate and ethene-vinyl acetate copolymers, important industrial polymers.
Production
The worldwide production capacity of v ...
and as an intermediate in the preparation of other chemical compounds.
With the invention of
polyaspartic technology the material found another use. In this situation, an amine is reacted with a dialkyl maleate - usually diethyl maleate but also dibutyl maleate may be used- utilizing the
Michael addition
In organic chemistry, the Michael reaction or Michael addition is a reaction between a Michael donor (an enolate or other nucleophile) and a Michael acceptor (usually an α,β-unsaturated carbonyl) to produce a Michael adduct by creating a carbon ...
reaction. The resulting products, polyaspartic esters products are then used in
coatings
A coating is a covering that is applied to the surface of an object, usually referred to as the substrate. The purpose of applying the coating may be decorative, functional, or both. Coatings may be applied as liquids, gases or solids e.g. Powd ...
,
adhesives
Adhesive, also known as glue, cement, mucilage, or paste, is any non-metallic substance applied to one or both surfaces of two separate items that binds them together and resists their separation.
The use of adhesives offers certain advant ...
,
sealants
Sealant is a substance used to block the passage of fluids through openings in materials, a type of mechanical seal. In building construction ''sealant'' is sometimes synonymous with ''caulking'' and also serve the purposes of blocking dust, sou ...
and
elastomers
An elastomer is a polymer with viscoelasticity (i.e. both viscosity and elasticity) and with weak intermolecular forces, generally low Young's modulus and high failure strain compared with other materials. The term, a portmanteau of ''elastic p ...
.
[{{Cite journal, last=Howarth, first=GA, date=2003-06-01, title=Polyurethanes, polyurethane dispersions and polyureas: Past, present and future, url=https://doi.org/10.1007/BF02699621, journal=Surface Coatings International Part B: Coatings Transactions, language=en, volume=86, issue=2, pages=111–118, doi=10.1007/BF02699621, s2cid=93574741, issn=1476-4865]
See also
*
Diethyl maleate
*
Dimethyl maleate
References
Maleate esters
Plasticizers