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Furfural

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Furfural
Names
IUPAC name
Furan-2-carbaldehyde
Other names
furfural, furan-2-carboxaldehyde, fural, furfuraldehyde, 2-furaldehyde, pyromucic aldehyde
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.389 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C5H4O2/c6-4-5-2-1-3-7-5/h1-4H checkY
    Key: HYBBIBNJHNGZAN-UHFFFAOYSA-N checkY
  • InChI=1/C5H4O2/c6-4-5-2-1-3-7-5/h1-4H
    Key: HYBBIBNJHNGZAN-UHFFFAOYAD
  • c1cc(oc1)C=O
Properties
C5H4O2
Molar mass 96.085 g·mol−1
Appearance Colorless oil
Odor Almond-like[1]
Density 1.16 g/mL (20 °C)[2]
Melting point −37 °C (−35 °F; 236 K)[2]
Boiling point 162 °C (324 °F; 435 K)[2]
83 g/L[2]
Vapor pressure 2 mmHg (20°C)[1]
-47.1·10−6 cm3/mol
Hazards
Flash point 62 °C (144 °F; 335 K)
Explosive limits 2.1%-19.3%[1]
Lethal dose or concentration (LD, LC):
300–500 mg/kg (oral, mice)[3]
370 ppm (dog, 6 hr)
175 ppm (rat, 6 hr)
1037 ppm (rat, 1 hr)[4]
370 ppm (mouse, 6 hr)
260 ppm (rat)[4]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 5 ppm (20 mg/m3) [skin][1]
REL (Recommended)
 No established REL[1]
IDLH (Immediate danger)
 100 ppm[1]
Related compounds
Related furan-2-carbaldehydes
 Hydroxymethylfurfural

Methoxymethylfurfural

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Furfural /ˈfɜːrfjəræl/ is an organic compound produced from a variety of agricultural byproducts, including corncobs, oat, wheat bran, and sawdust. The name furfural comes from the Latin word [furfur] Error: {{Lang}}: text has italic markup (help), meaning bran, referring to its usual source. Aside from ethanol, acetic acid and sugar it is one of the oldest renewable chemicals.[5]

Chemically, furfural is an aldehyde of furan. It is a colorless oily liquid with the odor of almonds, which quickly darkens when exposed to air.

History

Furfural was first isolated in 1821 (published in 1832) by the German chemist Johann Wolfgang Döbereiner, who produced a small sample as a byproduct of formic acid synthesis.[6][7] 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; he also determined an empirical formula of (C5H4O2).[7] George Fownes named this oil furfurol in 1845 (from furfur - bran, and oleum).[8] This name persisted prominently in the literature until 1901 when the German chemist Carl Harries deduced furfural's structure.[citation needed]

Furfural remained a relatively obscure chemical until 1922,[5] when the Quaker Oats Company began mass-producing it from oat hulls.[9] Today, furfural is still produced from agricultural byproducts like sugarcane bagasse and corn cobs. The main countries producing furfural today are the Dominican Republic, South Africa and China.

Properties

Furfural dissolves readily in most polar organic solvents, but is only slightly soluble in either water or alkanes.

Furfural participates in the same kinds of reactions as other aldehydes and other aromatic compounds, but has less aromatic character than benzene, as can be seen from the fact that furfural is readily hydrogenated to the corresponding tetrahydrofuran derivatives. When heated in the presence of acids, furfural irreversibly solidifies, acting as a thermosetting polymer.

Production

Furfural may be obtained by the acid catalyzed dehydration of 5-carbon sugars (pentoses), particularly xylose.[10]

C5H10O5 → C5H4O2 + 3 H2O

These sugars may be obtained from hemicellulose present in lignocellulosic biomass, which can be extracted from most terrestrial plants.

Between 3% and 10% of the mass of crop residue feedstocks can be recovered as furfural, depending on the type of feedstock. Furfural and water evaporate together from the reaction mixture, and separate upon condensation. The global production capacity is about 800,000 tons as of 2012. China is the biggest supplier of furfural, and accounts for the greater part of global capacity. The other two major commercial producers are Illovo Sugar in the Republic of South Africa and Central Romana in the Dominican Republic.

In the laboratory, furfural can be synthesized from plant material by reflux with dilute sulfuric acid[11]or other acids.[12]

In industrial production, some lignocellulosic residue remains after the removal of the furfural. This residue is dried and burned to provide steam for the operation of the furfural plant. Newer and more energy efficient plants have excess residue, which is or can be used for co-generation of electricity,[13][14] cattle feed, activated carbon, mulch/fertiliser, etc. It also has been used as a glue extender in the North American board industry.[15]

This synthesis is similar to the production of hydroxymethylfurfural by the acid catalyzed dehydration of 6-carbon sugars (hexoses)

Uses

Furfural is an important renewable, non-petroleum based, chemical feedstock. Hydrogenation of furfural provides furfuryl alcohol (FA), which is a used to produce furan resin prepolymers exploited in thermoset polymer matrix composites, cements, adhesives, casting resins and coatings. Further hydrogenation of furfuryl alcohol leads to tetrahydrofurfuryl alcohol (THFA), which is used as a solvent in agricultural formulations and as an adjuvant to help herbicides penetrate the leaf structure. Furfural is used to make other furan derivative, such as furoic acid, via oxidation,[16] and furan itself via palladium catalyzed vapor phase decarbonylation.[3] Furfural is also a specialized chemical solvent.


Safety

Although it occurs in many foods and flavorants, furfural is toxic with an LD50 of 65 mg/kg (oral, rat).[17] It is a skin irritant and chronic skin exposure can lead to a skin allergy as well as an unusual susceptibility to sunburn.

The Occupational Safety and Health Administration has set a permissible exposure limit for furfural at 5 ppm over an eight-hour time-weighted average, and also designates furfural as a risk for skin absorption.[1]

See also

References

  1. ^ a b c d e f g NIOSH Pocket Guide to Chemical Hazards. "#0297". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ a b c d Record of CAS RN 98-01-1 in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  3. ^ a b H. E. Hoydonckx, W. M. Van Rhijn, W. Van Rhijn, D. E. De Vos, P. A. Jacobs "Furfural and Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry 2007, Wiley-VCH, Weinheim. doi:10.1002/14356007.a12_119.pub2
  4. ^ a b "Furfural". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  5. ^ a b Peters, Fredus N. (1936). "The Furans: Fifteen Years of Progress". Industrial & Engineering Chemistry. 28 (7): 755–759. doi:10.1021/ie50319a002. ISSN 0019-7866.
  6. ^ J. W. Döbereiner (1832). "Ueber die medicinische und chemische Anwendung und die vortheilhafte Darstellung der Ameisensäure". Berichte der deutschen chemischen Gesellschaft. 3 (2): 141–146. doi:10.1002/jlac.18320030206.
  7. ^ a b John Stenhouse (1843). "On the Oils Produced by the Action of Sulphuric Acid upon Various Classes of Vegetables. [Abstract]". Abstracts of the Papers Communicated to the Royal Society of London. 5: 939–941.
  8. ^ George Fownes (1845). "An Account of the Artificial Formation of a Vegeto-Alkali". Philosophical Transactions of the Royal Society of London. 135: 253–262.
  9. ^ Brownlee, Harold J.; Miner, Carl S. (1948). "Industrial Development of Furfural". Industrial & Engineering Chemistry. 40 (2): 201–204. doi:10.1021/ie50458a005. ISSN 0019-7866.
  10. ^ Roger Adams and V. Voorhees (1921). "Furfural". Organic Syntheses. 1: 49; Collected Volumes, vol. 1, p. 280.
  11. ^ Roger Adams and V. Voorhees (1922). "Furfural". Organic Syntheses. 1: 49; Collected Volumes, vol. 1, p. 280.
  12. ^ J., Zeitsch, Karl (2000). The chemistry and technology of furfural and its many by-products. Amsterdam: Elsevier. ISBN 9780080528991. OCLC 162130560.{{cite book}}: CS1 maint: multiple names: authors list (link)
  13. ^ Edgard,, Gnansounou,. Life-cycle assessment of biorefineries. Pandey, Ashok,. Amsterdam, Netherlands. ISBN 9780444635860. OCLC 967224456.{{cite book}}: CS1 maint: extra punctuation (link) CS1 maint: multiple names: authors list (link)
  14. ^ Virtual biorefinery : an optimization strategy for renewable carbon valorization. Bonomi, Antonio,, Cavalett, Otávio,, Cunha, Marcelo Pereira da,, Lima, Marco A. P.,. Cham. ISBN 9783319260457. OCLC 932064033.{{cite book}}: CS1 maint: extra punctuation (link) CS1 maint: others (link)
  15. ^ 1938-, Sellers, Terry, (1985). Plywood and adhesive technology. New York: M. Dekker. ISBN 9780824774073. OCLC 12344447. {{cite book}}: |last= has numeric name (help)CS1 maint: extra punctuation (link) CS1 maint: multiple names: authors list (link)
  16. ^ R. J. Harrison and M. Moyle, Organic Syntheses, Coll. Vol. 4, p.493 (1963); Vol. 36, p.36 (1956).
  17. ^ "ChemIDplus Advanced - Chemical information with searchable synonyms, structures, and formulas". chem.sis.nlm.nih.gov.
  • Furfural in the Pesticide Properties DataBase (PPDB)
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