| Maleic
Anhydride is the anhydride of cis-butenedioic acid (maleic
acid) which carboxylic acid groups are next to each
other in the cis form. Maleic Anhydride has a cyclic
structure with a ring containing four carbon atoms and
one oxygen atom. It is soluble in acetone, hydrolyzing
in water. It is prepared in commerce by the oxidation of benzene
with catalyst at high temperatures or by the
reaction of C4 (butane) with oxygen in the presence of vanadium catalyst. It is used in 1,4-cyclo
polyaddition and polycondensation as a dienophile. Maleic
Anhydride's biggest single use is in the manufacture
of unsaturated polyester resins for use in fibre-reinforced
plastics in the automotive, construction, marine, consumer
goods and agricultural industries. Producers are working
at capacity, but maleic supplies are barely adequate
for market requirements due to planned and unplanned
downtime in recent days and continued strong demand.
Maleic
Anhydride has attractive molecule structure in chemistry.
Its reactivity of the two carbonyl groups
and the solid bond in conjugation with the two carbonyl
oxygens provide broad applications in commerce. Examples
of reactions which maleic anhydride are :
- Acylation
- Alkylation
- Amidation
- Cycloaddition
- Decomposition
and Decarboxylation
- Diels-Alder
reaction
- Electrophilic
Addition and Nucleophilic Addition
- Ene
Reaction
- Esterification
- Formation
of Acid Chloride
- Grignard
Reactions
- Halogenation
- Heterogeneous
catalytic reduction
- Hydration
and Dehydration
- Hydroformylation
- Isomerization
- Ligation
- Michael Addition
- Ozonolysis and
Oxidaton
- Polymerization
|
|
Unsaturated
polyester resins, lubricating oil additives, copolymers,
fumaric acid, agricultural chemicals, malic acid, sulfosuccinic
acid esters, alkenyl succinic anhydrides and alkyd resins.
|
| Anhydride is a
compound formed by the abstraction of a molecule of water,
H2O, from a substance.
The term acid anhydride is restricted sometime to the anhydride formed
especially from an acid by dehydration or one that revert to the original
substance upon hydration. In case of bimolecular, it can be composed of two
molecules of the corresponding acid. The term mixed anhydride is an acid
anhydride composed of two different acids. Examples are adenosine triphosphate
or an aminoacyl adenylate. The anhydrides of bases are oxides.
Anhydrides of
inorganic acids are usually oxides of nonmetallic elements. Carbon dioxide
(CO2) is the anhydride of
carbonic acid, dinitrogen pentoxide (N2O5) is the anhydride of
nitric acid, sodium oxide is an anhydride of sodium hydroxide,
phosphorus pentoxide (P2O5) is the anhydride of
phosphoric acid, and sulfur trioxide (SO3) is the anhydride of
sulfuric acid. An acid anhydride forms
an acid; a base anhydride forms a base.
Sulfur trioxide (acid anhydride) reacts with water to form sulfuric acid (an
acid product). Calcium oxide
(an base anhydride) reacts with water to form calcium hydroxide (a base product).
Organic anhydrides contain the carbonyl group (CO).
Organic anhydrides are formed by the condensation of original acids. Lactone, an
internal cyclic monoester, is an anhydride derived from the hydroxyl and
carboxyl radicals. In organic chemistry, most
anhydride compounds are
derived from corresponding carboxylic acids. Carboxylic anhydrides, general formula (RCO)2O, are
the dehydration product of two carboxylic acid molecules. The name of carboxylic
anhydride is
given first from the original acid, followed by the separate word "anhydride".
[CH3(CH2)2CO]2O is butanoic
anhydride, CH3COOCOCH2CH3 is
ethanoic propanoic anhydride (or
acetic propionic anhydride). Anhydrides are more reactive than the parent acids. Anhydrides are typically not
target molecules, but rather they are used as intermediates for the synthesis of
other organic members such as esters and amides for the industrial applications
include dyes, pharmaceuticals, pesticides, plastics, fibers, curing agents,
plasticizers and many others. The reactivity
of carboxylic acid derivatives are in order of acyl halides > anhydrides >> esters ¡Ö acids >> amides.
Anhydrides react with alcohols to form esters; acetic anhydride [(CH3CO)2O] reacts with
ethanol (C2H5OH)
to form ethyl acetate (CH3COOC2H5)
used as a common solvent. Anhydrides also react with ammonia and
primary or secondary amines to form amides. Anhydrides react with water to form their corresponding acids.
|