FURFURAL

CAS Number: 98-01-1
EC Number: 202-627-7
Molecular Formula: C₅H₄O₂
Molar Mass: 96.09 g/mol

Furfural is an organic compound with the formula C4H3OCHO.
Furfural is a colorless liquid, although commercial samples are often brown.
Furfural has an aldehyde group attached to the 2-position of furan.

Furfural is a product of the dehydration of sugars, as occurs 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.

Furfural is also found in many processed foods and beverages.
Furfural, also known as 2-Furaldehyde is based on waste corn cob used in the synthesis of pharmaceutical, industrial and agricultural chemicals.

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.

Properties of Furfural:
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.
Furfural exhibits less aromatic character than benzene, as can be seen from the fact that furfural is readily hydrogenated to tetrahydrofurfuryl alcohol.
When Furfural is heated in the presence of acids, furfural irreversibly polymerizes, acting as a thermosetting polymer.

Uses and occurrence of Furfural:
Furfural is found in many foods: coffee (55–255 mg/kg) and whole grain bread (26 mg/kg).
Furfural is an important renewable, non-petroleum based, chemical feedstock.
Furfural can be converted into a variety of solvents, polymers, fuels and other useful chemicals by a range of catalytic reduction.

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

Furfural is also a specialized chemical solvent.
There is a good market for value added chemicals that can be obtained from furfural.

General description of Furfural:
Furfural is a heterocyclic aldehyde.
Furfural can be produced from agricultural raw materials containing pentosans and lignocellulosic feedstock.
Furfural is also obtained from xylose, via dehydration.
Furan has various interesting properties, such as it thermosets easily, has physical strength and exhibits resistance to corrosion.

Furfural is a raw material for the production of various furan-based chemicals and solvents such as:
-methylfuran
-furfuryl alcohol
-tetrahydrofurfuryl alcohol
-tetrahydrofuran
-methyltetrahydrofuran
-dihydropyran
-furoic acid

Furfural is a product of the dehydration of sugars, as occurs in a variety of agricultural byproducts, including corncobs, oat, wheat bran, and sawdust.

KEYWORDS:
98-01-1, 202-627-7, Artificial ant oil, 2-formylfuran, furaldehyde, 2-furanaldehyde, UNII-DJ1HGI319P, .alpha.-Furole, NSC 8841, MFCD00003229

Furfural, or furan-2-carbaldehyde, is an oily liquid formed when sugars from lignocellulosic biomasses such as corncobs, sawdust, and oat hulls dehydrate.
This is a natural process that is the basis of the commercial production of furfural.

In the first half of the 19th century, chemists such as Johann W. Döbereiner at the University of Jena (Germany) and John Stenhouse at Glasgow University discovered furfural in the distillation products of various biomaterials.
Furfural did not become an industrial product until Quaker Oats (Chicago) began to produce it on a large scale from oat hulls.

Furfural, one of the earliest sustainable chemical feedstocks, is used to synthesize a wide range of industrial chemicals, including solvents, resins, plastics, and furan derivatives.
As the hazard information table shows, Furfural must be handled with an abundance of caution.

Furfural is one of several five-carbon oxygenated hydrocarbons that make up the aroma of canned pumpkin you might use to make your Thanksgiving pumpkin pie.
Oddly, this odor differs significantly from that of the six-carbon compounds, such as former Molecule of the Week cis-3-hexen-1-ol, that emanates from freshly cut pumpkins.

Furfural in practice:
Furfural has an aromatic odour reminiscent of almonds.
This biomass-based chemical is a hetero-aromatic aldehyde with exceptional physical properties.

Applications of Furfural include:
-selective solvent in refining lubricating oils to produce high-quality motor oil with improved temperature-viscosity properties
-decolourizing agent to refine crude wood rosin
-purification of C4 and C5 hydrocarbons for manufacturing synthetic rubber
-reactive solvent and excellent wetting agent in manufacturing abrasive wheels, brake linings and refractory products for the steel industry
-chemical feedstock for furfuryl alcohol and other derivatives

Applications of Furfural:
Furfural undergoes hydrogenation in the vapor-phase over copper-containing catalysts to form furfuryl alcohol as the predominant product.
Furfural may also be used to prepare gel precursors for phenol-furfural aerogels.
Furfural has been employed as a standard for the HPLC quantification of furfural in the autohydrolysate liquor obtained from microwave-irradiated maize bran.
Furfural may be used in the preparation of γ-valerolactone (GVL) and biofuel 2-methylfuran (51% yield).

Function and Uses of Furfural:
Large quantities of Furfural are used in solvent extraction in the petroleum refining industry.
Furfural is also used as a solvent (for nitrated cotton, cellulose acetate and gums), to accelerate vulcanization, as an ingredient of phenolic resins (Durite), as an intermediate in the synthesis of furan derivatives, as a weed killer, as a fungicide and as a flavouring agent.
Furfural has been identified in 150 foods, including fruits, vegetables, beverages, bread and bread products.
The highest reported concentrations were found in wheat bread (0.8–14 ppm) [mg/kg], cognac (0.6–33 ppm), rum (22 ppm), malt whisky (10–37 ppm), port wine (2–34 ppm) and coffee (55–255 ppm).

The concentrations of Furfural in juices were 0.01–4.93 ppm.
Furfural is an ingredient contained in many fragrances and flavours.
Furfural may be found in fragrances used in decorative cosmetics, fine fragrances, shampoos, toilet soaps and other toiletries, in flavours of oral care products as well as in non-cosmetic products such as household cleaners and detergents.
Furfural in the in the fragrance compound is reported to be 0.036% or less.

Production of Furfural:
Furfural may be obtained by the acid catalyzed dehydration of 5-carbon sugars (pentoses), particularly xylose.
C5H10O5 → C5H4O2 + 3 H2O

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.
In the laboratory, furfural can be synthesized from plant material by heating with sulfuric acid or other acids.

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.
The formation and extraction of xylose and subsequently furfural can be favored over the extraction of other sugars with varied conditions, such as acid concentration, temperature, and time.
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, cattle feed, activated carbon, mulch/fertiliser, etc.

History of Furfural:
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.
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).
George Fownes named this oil "furfurol" in 1845 (from furfur (bran), and oleum (oil)).

In 1848, the French chemist Auguste Cahours determined that furfural was an aldehyde.
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.

By 1886, furfurol was being called "furfural" (short for "furfuraldehyde") and the correct chemical structure for furfural was being proposed.
By 1887, the German chemist Willy Marckwald had inferred that some derivatives of furfural contained a furan nucleus.
In 1901, the German chemist Carl Harries determined furan's structure by synthesizing it from succindialdehyde, thereby also confirming furfural's proposed structure.

Furfural remained relatively obscure 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.
The main countries producing furfural today are the Dominican Republic, South Africa and China.

Safety of Furfural:
Furfural is carcinogenic in lab animals and mutagenic in single cell organisms, but there is no data on human subjects.
Furfural 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.
Furfural is hepatotoxic.

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

Preferred IUPAC name:
Furan-2-carbaldehyde

Other names:
Furfural, furan-2-carboxaldehyde, fural, furfuraldehyde, 2-furaldehyde, pyromucic aldehyde

Where Do We Get That From?
Have you ever wondered where a lot of our chemical feedstocks come from?
What we are referring to by 'feedstocks' is raw materials that can be used to manufacture chemicals that are important to the chemical industry and things we rely on daily for our lives.
Obviously, we don't just get these raw materials out of thin air so where do they come from?
Well, most raw materials we rely on actually come from petroleum-based sources.
As you're probably aware, petroleum is a yellow-black liquid found beneath the earth's surface that contains various organic compounds (carbon-based compounds) that can be separated from one another into feedstocks that can be used by chemists for other chemicals.

Petroleum sources aren't going to last forever, and so there's been a big push recently for scientists to come up with alternative sources of fuel and feedstocks that aren't reliant on petroleum.
In this lesson, we are going to be learning about an organic compound called furfural, which is considered a renewable chemical feedstock that's non-petroleum based (meaning it doesn't come from petroleum sources).
Our main topics of discussion will be the structure of furfural, how it's made in terms of production, and finally some of the more important uses in which it finds application.

Structure of Furfural:
Let's get started by looking at the structure of furfural.
Furfural is an aldehyde of furan and is a yellow oily liquid in pure form, but tends to turn brown upon prolonged exposure to air and moisture.
An aldehyde is an organic functional group that has a carbonyl group (carbon-oxygen double bond) attached to a hydrogen and some other carbon-based side chain.
Furan is an aromatic five-membered ring that has an oxygen atom embedded within the ring system.
Notice that the aldehyde portion of the molecule is bonded to the carbon that's directly adjacent to the oxygen of the furan ring.

Due to the polar nature of furfural, it will dissolve quite readily and form solutions with a variety of polar organic solvents like methanol, ethanol, chloroform, and dimethyl sulfoxide (DMSO).
It will not, however, dissolve in water and particularly non-polar solvents like hexane.

Production of Furfural:
We mentioned previously that furfural was a renewable chemical feedstock.
The reason this is the case actually stems from how it's made. Furfural can be produced on large industrial scales by taking plant mass and treating it with an acid.
When this happens, the 5-carbon sugar molecules undergo a dehydration (loss of water) reaction to give furfural.

Depending on the type of plant matter that's used, anywhere between 3% and 10% of the original plant mass can be recovered as furfural.
Obviously, plants are constantly growing and being produced, that's why furfural is considered a 'green' or renewable source of chemical feedstocks.
Furfural could potentially represent an important source of organic compounds once petroleum resources start to dry up.

Uses of Furfural:
Now that we know what the structure of furfural looks like and how it's produced, let's talk about a couple of the more important applications it can be utilized for.
If we take furfural and convert the aldehyde to an alcohol in what's called a reduction reaction, we get furfuryl alcohol (abbreviated FA).
FA is used in the manufacture of things like cement, adhesives, castings, and coatings.

CAS Number: 98-01-1
CHEBI:34768
ChEMBL: ChEMBL189362
ChemSpider: 13863629
ECHA InfoCard: 100.002.389
KEGG: C14279
PubChem CID: 7362
UNII: DJ1HGI319P
CompTox Dashboard (EPA): DTXSID1020647

Recently, furfural, “the sleeping beauty bio-renewable chemical” has gained a renewed attention as a potential chemical for the production of biofuels and biochemicals.
Furfural is the most commonly produced industrial chemical because its production is very flexible.
Furfural is one of the top value-added chemicals that can be produced from biomass.

Furfural and its derivatives have been extensively used in plastics, pharmaceutical and agrochemical industries.
Furfural is a natural precursor to a range of furan-based chemicals and solvents such as dihydropyran, methyltetrahydrofuran, tetrahydrofuran, methylfuranfurfuryl alcohol, tetrahydrofurfuryl alcohol and furoic acid.
Furfural and its derivatives have been widely applied as fungicides and nematicides, transportation fuels, gasoline additives, lubricants, resins, decolorizing agents, jet fuel blend stocks, drugs, insecticides, bio-plastics, flavor enhancers for food and drinks, rapid all-weather repair system for bomb-damaged runways and pot holes and also for wood modification and book preservation.

Furfural (CAS Reg. no. 98-01-1) is a naturally occurring furan aldehyde with many commercial uses, e.g., industrial manufacturing, food flavoring, fragrance in personal care products, pesticide.
Furfural is not expected to be persistent in the environment.
Furfural is rapidly absorbed and eliminated after inhalation, dermal, and oral exposures.
Furfural has higher dermal toxicity than by oral and inhalation routes.

Furfural is a skin, mucous membrane, and respiratory irritant.
The main toxicity targets are respiratory system, nervous system, liver, and kidneys.
Furfural is not classifiable regarding its carcinogenicity to humans.
Furfural is moderately toxic to aquatic species.

Chemical formula: C5H4O2
Molar mass: 96.085 g·mol−1
Appearance : Colorless oil
Odor: Almond-like
Density: 1.1601 g/mL (20 °C)
Melting point: −37 °C (−35 °F; 236 K)
Boiling point: 162 °C (324 °F; 435 K)
Solubility in water: 83 g/L
Vapor pressure: 2 mmHg (20 °C)
Magnetic susceptibility (χ): −47.1×10−6 cm3/mol

Furfural is an organic compound obtained during the dehydration of sugars.
Furfurals IUPAC name is furan-2-carbaldehyde.
The word, furfural comes from the Latin word furfur that stands for bran, its usual source.
Sugars present in a variety of agricultural byproducts such as corn cobs, oats, wheat bran, and sawdust are used to produce furfural.
Furfural is commonly used in many processed foods and beverages.

Furfural is a colourless liquid that darkens on exposure to air.
Furfural is the best-known member of the furan family.
Furfural meaning is furfuraldehyde or also called 2-furaldehyde.
Furfural is also an important source of other furans.
The boiling point of furfuraldehyde is 161.70C.

The chemical formula for furfuraldehyde or furfural aldehyde is C4H3O-CHO.
In 1922, Quaker Oats company started producing furfural from oat hulls for commercial use much after its discovery by a German scientist Johann Wolfgang in 1821.
The industrial development of the production of furfural is a great example of how industries utilize agricultural residues.
The major raw material source of furfural such as corncobs, oat hulls, cottonseed hulls, rice hulls, and bagasse are replenished annually ensuring a constant supply of raw material for the production of furfural.

In large rotary digesters, lots of raw material and dilute sulphuric acid are steamed under pressure.
The furfural form is continuously removed with steam and then concentrated with the help of distillation.
The furfural obtained by distillation separates into two layers of condensation and the wet furfural at the bottom is dried with the help of vaccum distillation to obtain furfural with a minimum of 99% purity.

Given below is the dehydration reaction of pentoses under an acid catalyst.
C5H10O5 → C5H10O2 + 3H2O
The furfural price remains stable in the market and is readily available at Furfural sigma Aldrich.
Global demands of furfural remain high with China as its leading production capacity of 85% and consumption of 75%.
Properties of Furfural has a molecular weight of 96.08 g/mol.

Furfural is denser than water and water-soluble.
Furfurals vapours are heavier than air.
Furfural has a distinct caramel taste and smells somewhat like benzaldehyde.
Furfural has a boiling point of 161.70C.

Furfural is considered a major platform chemical that is used in the production of various other chemicals.
Furfural strongly resembles benzaldehyde in its reactions as an aldehyde.
In the presence of strong aqueous alkali, it undergoes a Cannizaro reaction.
Furfural dimerizes furoin under the influence of potassium cyanide and by the action of ammonia is converted into hydro furamide (C4H3O-CH)3N2.
On exposure to air at room temperature, furfural degrades into formic acid and formerly acrylic acid.

Furoic or furfural acid is a crystalline solid, white in colour, and is used as a bactericide and a preservative.
Furfurals esters are fragrant liquids commonly used in perfumes and flavourings.
Furfural is an arenecarbaldehyde that is slightly soluble in water and is used as a food flavouring agent.
Furfural is also used as a fragrance agent for in-home products or similar industrial products.

Furfural is an organic compound obtained upon dehydration of sugars, which is highly soluble in water and organic solvents.
Furfural is used as an additive agent in the food industry and also in the production of various fuels and chemicals.
Furfural is absent in fresh food but is naturally generated upon heating of sugar-containing food items.
Furfural is one of the furan derivatives from hemicellulose present in lignocellulosic.
Furfural is naturally obtained upon dehydration of xylose, which is a pentose sugar.

This heterocyclic and aromatic aldehyde consists of an aldehyde side group and a furan ring.
Furfural is a colourless liquid and has an oily appearance with an almond-like odour.
Furfural has various industrial purposes being a platform chemical that is used in the production of various other chemical compounds.
Furfural is also used in the production of furan compounds.

Chemical Name: Furfural
Synonyms: 2-Furancarboxaldehyde; 2-Furaldehyde; 2-Formylfuran; 2-Furanaldehyde; 2-Furancarbaldehyde; 2-Furancarbonal; 2-Furfural; 2-Furfuraldehyde; 2-Furylaldehyde; 2-Furylcarboxaldehyde; Artificial ant oil; Fural; Furaldehyde; Furan-2-carboxaldehyde; Furancarbonal; Furfuraldehyde; Furfurol; Furfurole; Furfurylaldehyde; Furole; NSC 8841; Pyromucic aldehyde; α-Furole
CAS Number: 98-01-1
Molecular Formula: C₅H₄O₂
Appearance: Light Yellow to Very Dark Brown Oil
Molecular Weight: 96.08
Storage: 4°C, Hygroscopic
Solubility: Chloroform (Sparingly), DMSO (Slightly), Methanol (Slightly)
Stability: Hygroscopic

Category:
Building Blocks; Miscellaneous;

Applications of Furfural:
Furfural is a compound mainly found in agricultural byproducts, and is produced from the hydrolysis and dehydration of xylan contained in lignocellulose using solid acid catalysts.
Furfural is also a potential platform for biofuels and inhibits fermentation in yeast.

CAS number: 98-01-1
EC index number: 605-010-00-4
EC number: 202-627-7
Hill Formula: C₅H₄O₂
Molar Mass: 96.09 g/mol
HS Code: 2932 12 00

A span of about 100 years marked the period from discovery of furfural in the laboratory to the first commercial production in 1922.
The subsequent industrial development provides an excellent example of the industrial utilization of agricultural residues.
Corncobs, oat hulls, cottonseed hulls, rice hulls, and bagasse are the major raw material sources, the annual replenishment of which ensures a continuing supply.

In the manufacturing process, lots of the raw material and dilute sulfuric acid are steamed under pressure in large rotary digesters.
The furfural formed is removed continuously with steam, and concentrated by distillation; the distillate, on condensation, separates into two layers.
The bottom layer, comprising wet furfural, is dried by vacuum distillation to obtain furfural of minimum 99 percent purity.

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.

LD50 (median dose): 300–500 mg/kg (oral, mice)
LC50 (median concentration):
370 ppm (dog, 6 hr)
175 ppm (rat, 6 hr)
1037 ppm (rat, 1 hr)
LCLo (lowest published):
370 ppm (mouse, 6 hr)
260 ppm (rat)
NIOSH (US health exposure limits):
PEL (Permissible): TWA 5 ppm (20 mg/m3) [skin]
REL (Recommended): No established REL
IDLH (Immediate danger): 100 ppm

Furfural is a naturally occurring product as well as being a synthetic one.
When released into the environment, it volatilizes readily.
In the air, furfural is degraded by reaction with hydroxy radicals produced photolytically.

If released into the soil, it is highly mobile and has a great potential to leach into groundwater.
Volatilization from the soil is expected to be slow.
Although data is limited, furfural is expected to biodegrade readily in the soil under both aerobic and anaerobic conditions.
Furfural will not bioconcentrate to any great extent in fish or wildlife.

Molecular Weight: 96.08
XLogP3: 0.4
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 2
Rotatable Bond Count: 1
Exact Mass: 96.021129366
Monoisotopic Mass: 96.021129366
Topological Polar Surface Area: 30.2 Å²
Heavy Atom Count: 7
Formal Charge: 0
Complexity: 70.5
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Furfural in distilled beverages.
Furfural is a compound derived from ethanol, which, if found in high amounts in alcoholic beverages, can cause severe discomfort.
During the production of distilled beverages, furfural (and hydroxymethyl furfural) is a by-product that may be involved as fermentation inhibitor.

In what part of the distillation process is furfural produced?
Furfural occurs mainly during hydrolysis (breakdown of molecules in aqueous solution), where fermentation occurs.
The raw materials to produce distilled beverages contain carbohydrates, which need hydrolysis to obtain sugars (mostly fructose).
These carbohydrates are a whole set of different compounds, from which problems can arise when hydrolyzing them due to their different conditions (short, long, branched chains, etc.).

Single chain carbohydrate sugars can caramelize during complex chain hydrolysis, and during this reaction, secondary compounds such as furfural are generated.
That is why this stage of the process (hydrolysis) is considered complicated, and it is important to have good control of this operation to avoid excessive production of furfural.

Furfural is also important to emphasize that furfural is part of all distilled beverages such as tequila, rum, whiskey, mezcal, etc.
Furfural cannot be removed in its entirety, but whether to reduce its amount present in distilled beverages.

What is the maximum furfural limit that any distilled beverage should have?
The standard that establishes the limits for furfural content in distilled beverages is the “Official Mexican Standard NOM-142-SSA1 / SCFI-2014 Alcoholic beverages.
Sanitary specifications Sanitary and commercial labeling.
”This standard establishes a maximum limit for furfural of 4 mg per 100 ml of anhydrous alcohol.

The symptoms that a person can present when ingesting a drink with a high content of furfural are: headache, nausea, diarrhea, abdominal pain and general discomfort.
Consuming distilled beverages with high levels of furfural can cause long-term severe liver problems.
Furfural is then a fundamental part in the composition of distilled beverages, however, a control of the concentrations of this compound must be established so as not to cause harm to consumers.

Correction of excess furfural.
Furfural is an excellent option for the reduction of furfural, as well as for the reduction of unwanted compounds, maintaining the profile of the distilled beverage desired by the producer.

Quality Level: 100
vapor density: 3.31 (vs air)
vapor pressure: 13.5 mmHg ( 55 °C)
assay: 99%
form: liquid
autoignition temp.: 599 °F
expl. lim.: 19.3 %
refractive index: n20/D 1.525 (lit.)
bp: 162 °C (lit.)
mp: −36 °C (lit.)
density: 1.16 g/mL at 25 °C (lit.)
SMILES string: [H]C(=O)c1ccco1
InChI: 1S/C5H4O2/c6-4-5-2-1-3-7-5/h1-4H
InChI key: HYBBIBNJHNGZAN-UHFFFAOYSA-N

Air & Water Reactions:
Flammable.
Furfural is sensitive to light and air.
Soluble in water, with mixing.

Fire Hazard:
Special Hazards of Combustion Products: Irritating vapors are generated when heated

Health Hazard:
Vapor may irritate eyes and respiratory system.
Liquid irritates skin and may cause dermatitis.

Reactivity Profile:
FURFURAL reacts with sodium hydrogen carbonate.
Furfural also can react with strong oxidizers.
An exothermic resinification of almost explosive violence can occur upon contact with strong mineral acids or alkalis.
Furfural forms condensation products with many types of compounds, including phenol, amines and urea.

Nomenclature:
Chem. Abstr. Serv Reg. No.: 98-01-1
Chem. Abstr. Name: 2-Furancarboxaldehyde
IUPAC Systematic Name: 2-Furaldehyde

Synonyms:
Artificial ant oil
2-formylfuran
fural
furaldehyde
2-furanaldehyde
2-furancarbaldehyde
furancarbonal
2-furancarbonal
2-furfutal
furfuraldehyde
2-furfuraldehyde;
furfurol
furfurole
furfurylaldehyde
furole
a-furole
2-furylaldehyde
2-furylcarboxaldehyde
pyromucic aldehyde

Title: Furfural
CAS Registry Number: 98-01-1
CAS Name: 2-Furancarboxaldehyde
Additional Names: 2-furaldehyde; pyromucic aldehyde; artificial oil of ants; "furfurol"
Molecular Formula: C5H4O2
Molecular Weight: 96.08
Percent Composition: C 62.50%, H 4.20%, O 33.30%

Properties of Furfural: Colorless oily liq. Peculiar odor, somewhat resembling the odor of benzaldehyde.
Turns yellow to brown on exposure to air and light and resinifies (the polymerization is greatly accelerated by hot alkali).
d425 1.1563. bp760 161.8°; bp100 103°; bp20 67.8°; bp1.0 18.5° mp -36.5°.
Volatile in steam. nD20 1.5261.
Absorption spectrum: Purvis, J. Chem. Soc. 97, 1655 (1910).
Sol in 11 parts water; very sol in alcohol, ether.
Flash pt, closed cup, 140°F (60°C); open cup, 155°F (68°C).
Lower explosive limit: 2.1% by vol in air.
Autoignition temp 797°F (392°C).
Keep in airtight container and protect from light.
LD50 orally in rats: 127 mg/kg (Jenner).

Production of Furfural:
Furfural has been produced since 1832 from renewable agricultural sources, such as nonfood residues of food crops and wood wastes.
The pentosan polysaccharides of these vegetable materials (xylan and arabinan) are almost as widely distributed in nature as is cellulose and are the major precursors of furfural.
Ail pentosancontaining substances are potentially usable, but only a relatively few (corn cobs, oat hulls and bagasse), which are available in large tonnages within a lirnited radius of furfural production facilities, are commercially significant.
Furfural is produced commercially in batch or continuous digesters, in which the pentosans are hydrolysed with strong inorganic acids to pentoses and the pentoses are subsequently cyclodehydrated to furfural.

Furfural is also produced by continuous hydrolysis of bark at 190°C and 12 atmospheres.
Worldwide consumption of furfural was estimated to have been 91 thousand tonnes in 1965, 136 thousand tonnes in 1973 and 159 thousand tonnes in 1978.
Furfural is produced by 31 companies in 15 countries, with eight producers in China and six in the Russian Federation.
ln the United States of Arnerica, 45- 57 thousand tonnes were used annuall y between 1965 and 1989.

Water:
Information on actual concentrations in water is very limited.
Low levels of furfural (up to 30 mg/L) were reported in wastewater from a furfural production plant; however, derivatives of furfural occurred at concentrations up to 300 mg/L.

Food:
Furfural has been identified in 150 foods, including fruits, vegetables, beverages, bread and bread products.
The highest reported concentrations were found in wheat bread (0.8-14 ppm) (mg/kg), cognac (0.6-33 ppm), rum (22 ppm), malt whisky (10-37 pprn), port wine (2-34 ppm) and coffee (55-255 ppm).

The concentrations of furfural in juices were 0.01-4.93 pprn.
Furfural is formed during the reaction of amino acids with sugars at 100°C for 4 h.
The occurrence of furfural in stored citrus products is recognized as an indication of deterioration; the concentrations in grapefruit juice samples stored at ambient temperature for over one year were 2.1-9.0 ppm.

Melting point: mp -36.5°
Boiling point: bp760 161.8°; bp100 103°; bp20 67.8°; bp1.0 18.5°
Flash point: Flash pt, closed cup, 140°F (60°C); open cup, 155°F (68°C)
Index of refraction: nD20 1.5261
Density: d425 1.1563
Toxicity data: LD50 orally in rats: 127 mg/kg (Jenner)

FURFURAL
2-Furaldehyde
furan-2-carbaldehyde
98-01-1
2-Furancarboxaldehyde
Furaldehyde
Furfuraldehyde
2-FormylfuranFural
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
2-Furil-metanale
2-furancarbaldehyde
Fufural
alpha-Furole
2-Formylofuran
Nci-C56177
2-Formyl furan
furan-2-aldehyde
2-Furankarbaldehyd
Rcra waste number U125
alpha-Furfuraldehyde
UNII-DJ1HGI319P
.alpha.-Furole
NSC 8841
MFCD00003229
CHEBI:34768
DJ1HGI319P
2-Furancarboxaldehyde, homopolymer
Bran oil
Furane-2-carbaldehyde
NCGC00091328-01
Quakeral
DSSTox_CID_647
DSSTox_RID_75709
DSSTox_GSID_20647
Furfural (natural)
Ant Oil, artificial
Furfurale [Italian]
Caswell No. 466
2-Formylofuran [Polish]
2-Furankarbaldehyd [Czech]
CAS-98-01-1
2-Furil-metanale [Italian]
25067-38-3
FEMA No. 2489
CCRIS 1044
HSDB 542
EINECS 202-627-7
UN1199
RCRA waste no. U125
EPA Pesticide Chemical Code 043301
BRN 0105755
Furaldehydes
Furfuralu
a-furfuraldehyde
Qo furfural
AI3-04466
a-Furole
2-furanal
Ant Oil
Furfural ACS grade
furan-2 carbaldehyde
Furfural, 99%
2-furancarboxyaldehyde
2-Furaldehyde, 8CI
2-furan-carboxaldehyde
2-Furanocarboxyaldehyde
Furfuraldehyde(Furfural)
2-Furylaldehyde xypropane
WLN: T5OJ BVH
EC 202-627-7
5-17-09-00292 (Beilstein Handbook Reference)
BIDD:ER0698
Furfural, ACS reagent, 99%
CHEMBL189362
QSPL 006
QSPL 102
DTXSID1020647
FEMA 2489
Furan-2-carbaldehyde (Furfural)
NSC8841
Furfural, >=98%, FCC, FG
Furfural, for synthesis, 98.0%
NSC-8841
STR00358
ZINC3861345
Tox21_111114
Tox21_202191
Tox21_300170
BDBM50486229
Furaldehydes [UN1199] [Poison]
STL283124
AKOS000118907
AM81812
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
DB-003668
CS-0015696
F0073
FT-0612462
A845786
Q412429
F1294-0048
UNII-N4G9GAT76C component HYBBIBNJHNGZAN-UHFFFAOYSA-N

2-formyl furan
formylfuran
2-furaldehyde
2-furan aldehyde
2-furan carbonal
2-furan carboxaldehyde
furan-2-carbaldehyde
furan-2-carboxaldehyde
2-furanaldehyde
2-furancarbonal
2-furancarboxaldehyde
2-furfural
furfural (furfuraldehyde) redist
furfural (natural)
furfural crude
furfural natural
furfural synthetic
furfural-refined flavor grade
furfuraldehyde
2-furfuraldehyde
a-furfuraldehyde
alpha-furfuraldehyde
furfuryl aldehyde
a-furole
2-furyl aldehyde
2-furyl carboxaldehyde
2-furyl methanal
2-furylcarboxaldehyde
2-furylmethanal
pyromucic aldehyde

Furfural [Wiki]
202-627-7 [EINECS]
2-Furaldehyd [German] [ACD/IUPAC Name]
2-Furaldehyde [ACD/IUPAC Name]
2-Furaldéhyde [French] [ACD/IUPAC Name]
2-Furanaldehyd
2-furanaldehyde
2-Furancarboxaldehyde [ACD/Index Name]
2-Furanecarbaldéhyde
2-furfural
2-Furfuraldehyde
98-01-1 [RN]
Aceton [German] [ACD/IUPAC Name]
formylfuran
Furaldehyde [Wiki]
Furan-2-carbaldehyde
Furan-2-carboxaldehyde
Furfuraldehyde
T5OJ BVH [WLN]
2-Formyl furan
2-FORMYLFURAN
2-Formylofuran [Polish]
2-Formylofuran
2-Furancarbaldehyde
2-furancarbonal
2-Furancarboxyaldehyde
2-Furankarbaldehyd [Czech]
2-Furil-metanale [Italian]
2-Furylaldehyde
2-Furylaldehyde xypropane
2-Furylcarboxaldehyde
2-furylmethanal
2-Furyl-methanal
5-17-09-00292 [Beilstein]
927866-58-8 [RN]
Azeton
Bran oil
E'2-Furaldehyde'
Formyl furan
FUFURAL
Fur-2-aldehyde
Fural
Furale
Furan-2-aldehyde
Furancarbonal
Furfural|furan-2-carbaldehyde
Furfural-d4 (Stabilized with BHT)
Furfurale [Italian]
Furfuralu
Furfurol [Wiki]
Furfurole
Furfurylaldehyde
Furol
Furole
Furyl-methanal
Pyromucic aldehyde
Qo furfural
Quakeral
STR00358
α-Furfuraldehyde
α-furole