FURFURAL

CAS No.: 98-01-1
EC No.: 202-627-7

Synonyms:
FURFURAL; Furfural; 2-Furaldehyde; furan-2-carbaldehyde; 98-01-1; 2-Furancarboxaldehyde; Furaldehyde; Furfuraldehyde; 2-Formylfuran; Fural; 2-Furanaldehyde; 2-Furancarbonal; 2-Furfural; 2-Furfuraldehyde; Furancarbonal; Furfurole; Furale; Furole; Furfurylaldehyde; Furol; 2-Furylaldehyde; 2-Furylcarboxaldehyde; Pyromucic aldehyde; 2-Furyl-methanal; Artificial ant oil; Furan-2-carboxaldehyde; Furfurale; Artificial oil of ants; Furyl-methanal; 2-Furylmethanal; Bran oil; 2-Furil-metanale; FURFURAL; Furfural; FURFURAL; Furfural; 2-furancarbaldehyde; Fufural; Quakeral; alpha-Furole; 2-Formylofuran; Nci-C56177; 2-Formyl furan; furan-2-aldehyde; 2-Furankarbaldehyd; Rcra waste number U125; alpha-Furfuraldehyde; Furfural (natural); Ant Oil, artificial; Furfurale [Italian]; Caswell No. 466; 2-Formylofuran [Polish]; UNII-DJ1HGI319P; FURFURAL; Furfural; .alpha.-Furole; NSC 8841; 2-Furankarbaldehyd [Czech]; 2-Furil-metanale [Italian]; FEMA No. 2489; CCRIS 1044; HSDB 542; CHEBI:34768; EINECS 202-627-7; MFCD00003229; UN1199; RCRA waste no. U125; EPA Pesticide Chemical Code 043301; BRN 0105755; DJ1HGI319P; AI3-04466; Furane-2-carbaldehyde; NCGC00091328-01; 2-Furaldehyde, 99%; FURFURAL; Furfural; DSSTox_CID_647; DSSTox_RID_75709; DSSTox_GSID_20647; Wood Tar; Pyroligneous acids; CAS-98-01-1; Furaldehydes; Furfuralu; a-furfuraldehyde; Qo furfural; a-Furole; Fuf ural; 2-furanal; Furancarboxaldehyde; Ant Oil; Pyroligneous vinegar; Furfural ACS grade; furan-2 carbaldehyde; Furfural, 99%; 2-furancarboxyaldehyde; Caswell No. 904; WOOD VINEGAR; 2-Furaldehyde, 8CI; 2-furan-carboxaldehyde; FURFURAL; Furfural; 2-Furanocarboxyaldehyde; Furfuraldehyde(Furfural); Pyroligneous acid extract; 2-Furylaldehyde xypropane; WLN: T5OJ BVH; EC 202-627-7; 5-17-09-00292 (Beilstein Handbook Reference); KSC214C0J; BIDD:ER0698; ACMC-20978u; FEMA No. 2967; FEMA No. 2968; Furfural, ACS reagent, 99%; CHEMBL189362; EBD294; QSPL 006; QSPL 102; DTXSID1020647; FURFURAL; Furfural; CTK1B4104; FEMA 2489; KS-00000WKJ; NSC8841; Furfural, >=98%, FCC, FG; Furfural, for synthesis, 98.0%; LS-28; Furaldehydes [UN1199] [Poison]; NSC-8841; STR00358; ZINC3861345; EINECS 232-450-0; Tox21_111114; Tox21_202191; Tox21_300170; ANW-13660; BDBM50486229; Furaldehydes [UN1199] [Poison]; SBB004386; STL283124; AKOS000118907; FURFURAL; Furfural; AM81812; EPA Pesticide Chemical Code 067206; Furfural, analytical reference material; MCULE-5757882837; Furfural 100 microg/mL in Acetonitrile; Furfural, natural, >=98%, FCC, FG; Furfural, SAJ first grade, >=99.0%; NCGC00091328-02; NCGC00091328-03; NCGC00091328-04; NCGC00253954-01; NCGC00259740-01; BP-31002; SC-18048; DB-003668; FURFURAL; Furfural; LS-162370; CS-0015696; F0073; FT-0612462; ST50213385; FURFURAL; Furfural; U1199; C14279; 72277-EP2277848A1; 72277-EP2308867A2; FURFURAL; Furfural; 72277-EP2308870A2; A845786; Q412429; F1294-0048; UNII-N4G9GAT76C component HYBBIBNJHNGZAN-UHFFFAOYSA-N; 39276-09-0; FURFURAL; Furfural; 2-Furaldehyde; furan-2-carbaldehyde; 98-01-1; 2-Furancarboxaldehyde; Furaldehyde; Furfuraldehyde; 2-Formylfuran; Fural; 2-Furanaldehyde; 2-Furancarbonal; 2-Furfural; 2-Furfuraldehyde; Furancarbonal; Furfurole; Furale; Furole; Furfurylaldehyde; Furol; 2-Furylaldehyde; 2-Furylcarboxaldehyde; Pyromucic aldehyde; 2-Furyl-methanal; Artificial ant oil; Furan-2-carboxaldehyde; Furfurale; Artificial oil of ants; Furyl-methanal; 2-Furylmethanal; Bran oil; 2-Furil-metanale; FURFURAL; Furfural; FURFURAL; Furfural; 2-furancarbaldehyde; Fufural; Quakeral; alpha-Furole; 2-Formylofuran; Nci-C56177; 2-Formyl furan; furan-2-aldehyde; 2-Furankarbaldehyd; Rcra waste number U125; alpha-Furfuraldehyde; Furfural (natural); Ant Oil, artificial; Furfurale [Italian]; Caswell No. 466; 2-Formylofuran [Polish]; UNII-DJ1HGI319P; FURFURAL; Furfural; .alpha.-Furole; NSC 8841; 2-Furankarbaldehyd [Czech]; 2-Furil-metanale [Italian]; FEMA No. 2489; CCRIS 1044; HSDB 542; CHEBI:34768; EINECS 202-627-7; MFCD00003229; UN1199; RCRA waste no. U125; EPA Pesticide Chemical Code 043301; BRN 0105755; DJ1HGI319P; AI3-04466; Furane-2-carbaldehyde; NCGC00091328-01; 2-Furaldehyde, 99%; FURFURAL; Furfural; DSSTox_CID_647; DSSTox_RID_75709; DSSTox_GSID_20647; Wood Tar; Pyroligneous acids; CAS-98-01-1; Furaldehydes; Furfuralu; a-furfuraldehyde; Qo furfural; a-Furole; Fuf ural; 2-furanal; Furancarboxaldehyde; Ant Oil; Pyroligneous vinegar; Furfural ACS grade; furan-2 carbaldehyde; Furfural, 99%; 2-furancarboxyaldehyde; Caswell No. 904; WOOD VINEGAR; 2-Furaldehyde, 8CI; 2-furan-carboxaldehyde; FURFURAL; Furfural; 2-Furanocarboxyaldehyde; Furfuraldehyde(Furfural); Pyroligneous acid extract; 2-Furylaldehyde xypropane; WLN: T5OJ BVH; EC 202-627-7; 5-17-09-00292 (Beilstein Handbook Reference); KSC214C0J; BIDD:ER0698; ACMC-20978u; FEMA No. 2967; FEMA No. 2968; Furfural, ACS reagent, 99%; CHEMBL189362; EBD294; QSPL 006; QSPL 102; DTXSID1020647; FURFURAL; Furfural; CTK1B4104; FEMA 2489; KS-00000WKJ; NSC8841; Furfural, >=98%, FCC, FG; Furfural, for synthesis, 98.0%; LS-28; Furaldehydes [UN1199] [Poison]; NSC-8841; STR00358; ZINC3861345; EINECS 232-450-0; Tox21_111114; Tox21_202191; Tox21_300170; ANW-13660; BDBM50486229; Furaldehydes [UN1199] [Poison]; SBB004386; STL283124; AKOS000118907; FURFURAL; Furfural; AM81812; EPA Pesticide Chemical Code 067206; Furfural, analytical reference material; MCULE-5757882837; Furfural 100 microg/mL in Acetonitrile; Furfural, natural, >=98%, FCC, FG; Furfural, SAJ first grade, >=99.0%; NCGC00091328-02; NCGC00091328-03; NCGC00091328-04; NCGC00253954-01; NCGC00259740-01; BP-31002; SC-18048; DB-003668; FURFURAL; Furfural; LS-162370; CS-0015696; F0073; FT-0612462; ST50213385; FURFURAL; Furfural; U1199; C14279; 72277-EP2277848A1; 72277-EP2308867A2; FURFURAL; Furfural; 72277-EP2308870A2; A845786; Q412429; F1294-0048; UNII-N4G9GAT76C component HYBBIBNJHNGZAN-UHFFFAOYSA-N; 39276-09-0

FURFURAL

Furfural
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Furfural
Furfural.svg
Furfural-3D-vdW.png
Names
IUPAC name
Furan-2-carbaldehyde
Other names
Furfural, furan-2-carboxaldehyde, fural, furfuraldehyde, 2-furaldehyde, pyromucic aldehyde
Identifiers
CAS Number    
98-01-1 check
3D model (JSmol)    
Interactive image
ChEBI    
CHEBI:34768 ☒
ChEMBL    
ChEMBL189362 check
ChemSpider    
13863629 check
ECHA InfoCard    100.002.389 Edit this at Wikidata
KEGG    
C14279 check
PubChem CID    
7362
UNII    
DJ1HGI319P check
CompTox Dashboard (EPA)    
DTXSID1020647 Edit this at Wikidata
InChI[show]
SMILES[show]
Properties
Chemical formula    C5H4O2
Molar mass    96.085 g·mol−1
Appearance    Colorless oil
Odor    Almond-like[1]
Density    1.1601 g/mL (20 °C)[2][3]
Melting point    −37 °C (−35 °F; 236 K)[2]
Boiling point    162 °C (324 °F; 435 K)[2]
Solubility in water    83 g/L[2]
Vapor pressure    2 mmHg (20 °C)[1]
Magnetic susceptibility (χ)    −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):
LD50 (median dose)    300–500 mg/kg (oral, mice)[4]
LC50 (median concentration)    
370 ppm (dog, 6 hr)
175 ppm (rat, 6 hr)
1037 ppm (rat, 1 hr)[5]
LCLo (lowest published)    
370 ppm (mouse, 6 hr)
260 ppm (rat)[5]
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).
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Infobox references
Furfural is an organic compound with the formula C4H3OCHO. It is a colorless liquid, although commercial samples are often brown. It has an aldehyde group attached to the 2-position of furan. It is a product of the dehydration of sugars, as occur in a variety of agricultural byproducts, including corncobs, oat, wheat bran, and sawdust. The name furfural comes from the Latin word furfur, meaning bran, referring to its usual source. Furfural is only derived from lignocellulosic biomass, i.e. its origin is non-food or non-coal/oil based. Aside from ethanol, acetic acid and sugar it is one of the oldest renewable chemicals.[6] It is also found in many processed foods and beverages.

Contents
1    History
2    Properties
3    Production
4    Uses and occurrence
5    Safety
6    See also
7    References
8    External links
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.[7][8] 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 furfural's empirical formula (C5H4O2).[8] George Fownes named this oil "furfurol" in 1845 (from furfur (bran), and oleum (oil)).[9] In 1848, the French chemist Auguste Cahours determined that furfural was an aldehyde.[10] Determining the structure of furfural required some time: the furfural molecule contains a cyclic ether (furan), which tends to break open when it's treated with harsh reagents. In 1870, German chemist Adolf von Baeyer speculated (correctly) about the structure of the chemically similar compounds furan and 2-furoic acid.[11][12][13] By 1886, furfurol was being called "furfural" (short for "furfuraldehyde") and the correct chemical structure for furfural was being proposed.[14] By 1887, the German chemist Willy Marckwald had inferred that some derivatives of furfural contained a furan nucleus.[15] In 1901, the German chemist Carl Harries determined furan's structure by synthesizing it from succindialdehyde, thereby also confirming furfural's proposed structure.[16][17]

Furfural remained relatively obscure until 1922,[6] when the Quaker Oats Company began mass-producing it from oat hulls.[18] 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 it is only slightly soluble in either water or alkanes.

Furfural participates in the same kinds of reactions as other aldehydes and other aromatic compounds. It exhibits less aromatic character than benzene, as can be seen from the fact that furfural is readily hydrogenated to tetrahydrofurfuryl alcohol. When heated in the presence of acids, furfural irreversibly polymerizes, acting as a thermosetting polymer.

Production
Furfural may be obtained by the acid catalyzed dehydration of 5-carbon sugars (pentoses), particularly xylose.[19]

C
5H
10O
5 → C
5H
4O
2 + 3 H
2O
These sugars may be obtained from pentosans obtained from hemicellulose present in lignocellulosic biomass.

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 [20]

In the laboratory, furfural can be synthesized from plant material by heating with sulfuric acid[21] or other acids.[22][20] With the purpose to avoid toxic effluents, an effort to substitute sulfuric acid with easily-separable and reusable solid acid catalysts has been studied around the world.[23]

In industrial production, some lignocellulosic residue remains after the removal of the furfural.[24] 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,[25][26] cattle feed, activated carbon, mulch/fertiliser, etc.

Uses and occurrence
It is found in many foods: coffee (55–255 mg/kg) and whole grain bread (26 mg/kg).[4]

Furfural is an important renewable, non-petroleum based, chemical feedstock. It can be converted into a variety of solvents, polymers, fuels and other useful chemicals by a range of catalytic reduction.[27]

Hydrogenation of furfural provides furfuryl alcohol (FA), which is used to produce Furan resins, which are exploited in thermoset polymer matrix composites, cements, adhesives, casting resins and coatings.[28] 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.

In another application as a feedstock, palladium-catalyzed decarbonylation on furfural manufactures industrially furan.[29]

Another important solvent made from furfural is methyltetrahydrofuran. Furfural is used to make other furan derivatives, such as furoic acid, via oxidation,[30] and furan itself via palladium catalyzed vapor phase decarbonylation.[4]

Furfural is also a specialized chemical solvent.[20]

There is a good market for value added chemicals that can be obtained from furfural.[20]

Safety
Furfural is carcinogenic in lab animals and mutagenic in single cell organisms, but there is no data on human subjects. It is classified in IARC Group 3 due to the lack of data on humans and too few tests on animals to satisfy Group 2A/2B criteria. It is hepatotoxic.[31][32][33][34]

The median lethal dose is low 650–900 mg/kg (oral, dogs), consistent with its pervasiveness in foods.[4]

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

6.8 Furfural as flavor enhancer for drinks and food
Furfural is generally recognized as a safe chemical. It is a natural degradation product of vitamin C (ascorbic acid) and also a significant product of fruit juices and wine. The longer the wine is aged, the greater the composition of furfural [22]. Regardless of the fact that furfural has an LD50 of 2330 mg/kg for dogs, its toxicity for humans is relatively low. The highest concentration of furfural is in cocoa and coffee (55–255 ppm). About 1–3 ppm of its concentration is in alcoholic beverages and 0.8–26 ppm in brown bread. It is also found in some essential oils, foods, and cosmetic products.

11.9 Furfural: An Aldehyde
Furfural is an important organic chemical. Furfural itself has many applications, such as oil refining, as a bonding agent in grinding and abrasive wheels, in pharmaceuticals, and the manufacture of phenolic resins. Furfural has been addressed as one of the most important biomass-derived chemicals. It is identified as a PC for liquid fuels production and also as a precursor for LVA and levulinate esters. Initially, furfural-derived products were identified as inhibitor compounds during the valorization of the lignocellulosic materials in fermentation (Monlau et al., 2014). Furfural is mainly produced by pentose degradation and also from the thermal degradation of 5-HMF at high temperatures (200–250°C). The hemicellulosic part of the plant biomass is rich in pentoses (xylose and arbinose), hence it can be transformed into furfural. The utilization of hemicellulose for the production of furfural could be a viable alternative instead of ethanol production. Current technologies have a limited yield for furfural due to many side reactions, such as cross-polymerization with other molecules and resinification and fragmentation of furfural itself. Yemiş and Mazza (2011) proved that a microwave-assisted process provided a highly efficient conversion of xylose and xylan of hemicellulosic biomass to furfural. Sahu and Dhepe (2012) achieved a 56% yield of furfural using a solid-acid catalyzed selective method for the conversion of solid hemicelluloses. Many process parameters were optimized to minimize the formation of by-products and increase the furfural yield. A biphasic reaction system for the continuous extraction of formed furfural to decrease the side reactions resulted in higher furfural yields (Gürbüz et al., 2012; Rong et al., 2012).A furfural derivative, furfuryl alcohol, accounted for over 85% of the overall furfural market in 2013 (Grand view research, 2015). The coming years will particularly aim at technology innovations to reduce production costs and therefore increase opportunities for new applications of furfural.

Furfural is a chemical compound produced by biomass rich in pentoses content in the hemicellulose as raw material, in a reaction catalysed in presence of strong acids. Is used as a potential platform to produce biofuels. In recent years, furfural has received special attention as a potential platform to produce biofuels and biochemicals. In a study conducted by the Department of Renewable Energy of the United States, furfural was selected as one of the 30 main chemicals that can be manufactured from biomass (Cai et al., 2014). Industrially, it is a very versatile chemical because of its multiple applications: utilized as a raw material to produce phenol-furfural-resins (Brown, 1959), or can be converted furfuryl alcohol, tetrahydrofurfuryl alcohol, furan, tetrahydrofuran and diols (Bhogeswararao, 2015). The Quaker Oats process is the oldest commercial form of producing furfural industrially. This process was created by the Quaker Oat company using oat cereal waste as raw material, which is mixed with sulfuric acid. The process consists in two steps, first the reaction zone in which the biomass reacted with a solution of sulfuric acid to convert the xylan fraction into furfural, then high vapour stream is introducing to the reactor to remove the furfural as fast as possible in order to avoid furfural polimerization (Marcotullio, 2011). The vapor stream from the reactor is condensed to feed the azeotropic distillation sequences in order to remove the excess of water and some by-products such as methanol and acetic acid (Marcotullio, 2011).

Under the economy circle concept, the study of the reaction zone in the production of furfural is important because it allows to reduce the excessive use of water, high energy consumption and the formation of decomposition products by reducing the separation costs. In this work aims to present a novel proposal for the simultaneous optimization having as objective function TAC as economic criteria, Condition Number as a control indicator and EI99 as environmental conditions in order to improve reactor productivity in the reaction zone in the furfural production process. So far, there are no publications reported in the literature where the multi-objective optimization methodology for the furfural reaction zone is solved.

6.2.7 Furfural
Furfural is the most common industrial chemical derived from lignocellulosic biomass, with an annual production volume of more than 200,000 tons [96,97]. Furfural production is exclusively based on the acid-catalyzed conversion of pentosan sugars present in agricultural and forestry residues [98]. The first commercial production of furfural was discovered at the Quaker Oats Company in 1921 [99]. At that time, the company had obtained vast quantities of oat hulls from the manufacture of oatmeal. Quaker Oats produced furfural in 50% yield (based on xylan) from hulls by treating them with dilute sulfuric acid and steam pressure [100]. As a platform molecule, some important chemicals could be produced via selective hydrogenolysis, reduction, ring opening, aldol condensation reactions, etc. (Fig. 1.19).

Furfural is used as a selective solvent for refining lubricating oils and rosin, and to improve the characteristics of diesel fuel and catalytic cracker recycle stocks. It is employed extensively in the manufacture of resin-bonded abrasive wheels and for the purification of butadiene needed for the production of synthetic rubber. The manufacture of nylon requires hexamethylenediamine, of which furfural is an important source. Condensation with phenol provides furfural-phenolic resins for a variety of uses.