Everything about Furfural totally explained
| Section2 =
| Section3 =
| Section4 =
| Section5 =
| Section6 =
| Section7 =
| Section8 =
}}
The
chemical compound furfural is an industrial chemical derived from a variety of
agricultural byproducts, including
corncobs,
oat and
wheat bran, and
sawdust. The name
furfural comes from the
Latin word
furfur, meaning bran, referring to its usual source.
Furfural is an
aromatic aldehyde, with the ring structure shown at right. Its
chemical formula is
C5 H4 O2. In its pure state, it's a colorless oily liquid with the odor of
almonds, but upon exposure to air it quickly becomes yellow.
History
Furfural was first isolated in 1832 by the
German chemist Johann Wolfgang Döbereiner, who formed a very small quantity of it as a byproduct of
formic acid synthesis. At the time, formic acid was formed by the
distillation of dead
ants, and Döbereiner's ant bodies probably contained some plant matter. In 1840, the
Scottish chemist
John Stenhouse found that the same chemical could be produced by distilling a wide variety of crop materials, including corn, oats, bran, and sawdust, with aqueous
sulfuric acid, and he determined that this chemical had an
empirical formula of C
5H
4O
2. In 1901, the German chemist
Carl Harries deduced furfural's structure.
Except for occasional use in
perfume, furfural remained a relatively obscure chemical until 1922, when the
Quaker Oats Company began mass-producing it from oat hulls. Today, furfural is still produced from agricultural byproducts like
sugarcane bagasse and
corn cobs.
Properties
Furfural's physical properties are summarized in the table at right. Furfural dissolves readily in most polar
organic solvents, but is only slightly soluble in either
water or
alkanes.
Chemically, furfural participates in the same kinds of reactions as other aldehydes and other aromatic compounds. The aromatic stability of furfural isn't as great as in
benzene, and furfural participates in
hydrogenation and other
addition reactions more readily than many other aromatics.
When heated above 250 °C, furfural decomposes into
furan and
carbon monoxide, sometimes explosively.
When heated in the presence of acids, furfural irreversibly solidifies into a hard thermosetting
resin.
Production
Many plant materials contain the
polysaccharide hemicellulose, a
polymer of
sugars containing five carbon atoms each. When heated with sulfuric acid, hemicellulose undergoes
hydrolysis to yield these sugars, principally
xylose. Under the same conditions of heat and acid, xylose and other five carbon sugars undergo dehydration, losing three water molecules to become furfural:
» C5H10O5 → C
5H
4O
2 + 3
H2O
For crop residue feedstocks, about 10% of the mass of the original plant matter can be recovered as furfural. Furfural and water evaporate together from the reaction mixture, and separate upon condensation.
Global total capacity of production is about 450,000 ton.
China is the biggest supplier of this product and they've about a half of global capacity.
In the laboratory, synthesis of furfural from corn cobs takes place by
reflux with dilute
sulfuric acid .
Uses
Furfural is used as a
solvent in
petrochemical refining to extract
dienes (which are used to make synthetic
rubber) from other
hydrocarbons.
Furfural, as well as its derivative
furfuryl alcohol, can be used either by themselves or in together with
phenol,
acetone, or
urea to make solid resins. Such resins are used in making
fiberglass, some
aircraft components, and automotive
brakes.
Furfural is also used as a chemical intermediate in the production of the solvents
furan and
tetrahydrofuran.
Hydroxymethylfurfural has been identified in a wide variety of heat processed foods.
Safety
When ingested or inhaled, furfural can cause
intoxication, including
euphoria,
headache,
dizziness,
nausea, and eventual unconsciousness and death due to respiratory failure. Contact with furfural irritates the
skin and
respiratory tract and can cause the
lungs to fill with fluid.
Chronic skin exposure can lead to a skin
allergy to the substance, as well as an unusual susceptibility to
sunburn. In toxicity studies, furfural has led to
tumors,
mutations, and
liver and
kidney damage in animals.
Further Information
Get more info on 'Furfural'.
|
External Link Exchanges
Do you know how hard it is to get a link from a large encyclopaedia? Well we're different and will prove it. To get a link from us just add the following HTML to your site on a relevant page:
<a href="http://furfural.totallyexplained.com">Furfural Totally Explained</a>
Then simply click through this link from your web page. Our crawlers will verify your link, extract the title of your web page and instantly add a link back to it. If you like you can remove the words Totally Explained and embed the link in article text.
As long as your link remains in place, we'll keep our link to you right here. Please play fair - our crawlers are watching. Your site must be closely related to this one's topic. Any kind of spamming, dubious practises or removing the link will result in your link from us being dropped and, potentially, your whole site being banned. |
