2-Methylfuran

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2-Methylfuran
2-Methylfuran.svg
2-Methylfuran-3D-balls.png
Names
Preferred IUPAC name
2-Methylfuran
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.007.814 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 208-594-5
PubChem CID
UNII
  • InChI=1S/C5H6O/c1-5-3-2-4-6-5/h2-4H,1H3 Yes check.svgY
    Key: VQKFNUFAXTZWDK-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C5H6O/c1-5-3-2-4-6-5/h2-4H,1H3
    Key: VQKFNUFAXTZWDK-UHFFFAOYAB
  • o1c(ccc1)C
  • Cc1ccco1
Properties
C5H6O
Molar mass 82.10 g/mol
AppearanceColorless to pale yellow/green liquid
Density 0.91546 g/mL (20 °C) [1]
Boiling point 64 [2] [1]  °C (147 °F; 337 K)
3000 mg/L (20 °C)
Solubility in ethanolSoluble
1.4332 (20 °C) [1]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Very flammable, harmful
NFPA 704 (fire diamond)
2
3
1
Flash point −22 °C; −8 °F; 251 K
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

2-Methylfuran, also known with the older name of sylvane, is a flammable, water-insoluble liquid [3] with a chocolate odor, found naturally in Myrtle and Dutch Lavender [4] used as a FEMA GRAS flavoring substance, [5] with the potential for use in alternative fuels.

Contents

Manufacture

2-Methylfuran is an article of commerce (chemical intermediate) and is normally manufactured by catalytic hydrogenolysis of furfural alcohol or via a hydrogenation-hydrogenolysis sequence from furfural in the vapor phase. [6]

See also

Related Research Articles

<span class="mw-page-title-main">Boiling point</span> Temperature at which a substance changes from liquid into vapor

The boiling point of a substance is the temperature at which the vapor pressure of a liquid equals the pressure surrounding the liquid and the liquid changes into a vapor.

<span class="mw-page-title-main">Enthalpy of vaporization</span> Energy to convert a liquid substance to a gas; a function of pressure

The enthalpy of vaporization, also known as the (latent) heat of vaporization or heat of evaporation, is the amount of energy (enthalpy) that must be added to a liquid substance to transform a quantity of that substance into a gas. The enthalpy of vaporization is a function of the pressure at which that transformation takes place.

<span class="mw-page-title-main">Formic acid</span> Simplest carboxylic acid (HCOOH)

Formic acid, systematically named methanoic acid, is the simplest carboxylic acid, and has the chemical formula HCOOH and structure H−C(=O)−O−H. It is an important intermediate in chemical synthesis and occurs naturally, most notably in some ants. Esters, salts and the anion derived from formic acid are called formates. Industrially, formic acid is produced from methanol.

<span class="mw-page-title-main">Tetrahydrofuran</span> Chemical compound

Tetrahydrofuran (THF), or oxolane, is an organic compound with the formula (CH2)4O. The compound is classified as heterocyclic compound, specifically a cyclic ether. It is a colorless, water-miscible organic liquid with low viscosity. It is mainly used as a precursor to polymers. Being polar and having a wide liquid range, THF is a versatile solvent.

Bromomethane, commonly known as methyl bromide, is an organobromine compound with formula CH3Br. This colorless, odorless, nonflammable gas is produced both industrially and biologically. It has a tetrahedral shape and it is a recognized ozone-depleting chemical. It was used extensively as a pesticide until being phased out by most countries in the early 2000s.

<span class="mw-page-title-main">Anthracene</span> Chemical compound

Anthracene is a solid polycyclic aromatic hydrocarbon (PAH) of formula C14H10, consisting of three fused benzene rings. It is a component of coal tar. Anthracene is used in the production of the red dye alizarin and other dyes. Anthracene is colorless but exhibits a blue (400–500 nm peak) fluorescence under ultraviolet radiation.

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 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. Aside from ethanol, acetic acid, and sugar, it is one of the oldest renewable chemicals. It is also found in many processed foods and beverages.

Furan is a heterocyclic organic compound, consisting of a five-membered aromatic ring with four carbon atoms and one oxygen atom. Chemical compounds containing such rings are also referred to as furans.

Hydrogenolysis is a chemical reaction whereby a carbon–carbon or carbon–heteroatom single bond is cleaved or undergoes lysis (breakdown) by hydrogen. The heteroatom may vary, but it usually is oxygen, nitrogen, or sulfur. A related reaction is hydrogenation, where hydrogen is added to the molecule, without cleaving bonds. Usually hydrogenolysis is conducted catalytically using hydrogen gas.

<span class="mw-page-title-main">Methyl formate</span> Chemical compound

Methyl formate, also called methyl methanoate, is the methyl ester of formic acid. The simplest example of an ester, it is a colorless liquid with an ethereal odour, high vapor pressure, and low surface tension. It is a precursor to many other compounds of commercial interest.

The heating value of a substance, usually a fuel or food, is the amount of heat released during the combustion of a specified amount of it.

<span class="mw-page-title-main">2-Pentanone</span> Chemical compound

2-Pentanone or methyl propyl ketone (MPK) is a ketone and solvent of minor importance. It is comparable to methyl ethyl ketone, but has a lower solvency and is more expensive. It occurs naturally in Nicotiana tabacum (Tobacco) and blue cheese as a metabolic product of Penicillium mold growth.

<span class="mw-page-title-main">Hydroxymethylfurfural</span> Chemical compound

Hydroxymethylfurfural (HMF), also 5-(hydroxymethyl)furfural, is an organic compound formed by the dehydration of reducing sugars. It is a white low-melting solid which is highly soluble in both water and organic solvents. The molecule consists of a furan ring, containing both aldehyde and alcohol functional groups.

<span class="mw-page-title-main">Furfuryl alcohol</span> Chemical compound

Furfuryl alcohol is an organic compound containing a furan substituted with a hydroxymethyl group. It is a colorless liquid, but aged samples appear amber. It possesses a faint odor of burning and a bitter taste. It is miscible with but unstable in water. It is soluble in common organic solvents.

1,5-Pentanediol is the organic compound with the formula HOCH2CH2CH2CH2CH2OH. Like other diols, this viscous colourless liquid is used as plasticizer and also forms polyesters that are used as emulsifying agents and resin intermediates.

<span class="mw-page-title-main">2,5-Furandicarboxylic acid</span> Chemical compound

2,5-Furandicarboxylic acid (FDCA) is an organic chemical compound consisting of two carboxylic acid groups attached to a central furan ring. It was first reported as dehydromucic acid by Rudolph Fittig and Heinzelmann in 1876, who produced it via the action of concentrated hydrobromic acid upon mucic acid. It can be produced from certain carbohydrates and as such is a renewable resource, it was identified by the US Department of Energy as one of 12 priority chemicals for establishing the “green” chemistry industry of the future. Furan-2,5-dicarboxylic acid (FDCA) has been suggested as an important renewable building block because it can substitute for terephthalic acid (PTA) in the production of polyesters and other current polymers containing an aromatic moiety.

<span class="mw-page-title-main">2-Methyltetrahydrofuran</span> Chemical compound

2-Methyltetrahydrofuran (2-MeTHF) is an organic compound with the molecular formula C5H10O. It is a highly flammable, mobile liquid. It is mainly used as a replacement for Tetrahydrofuran (THF) in specialized applications for its better performance, such as to obtain higher reaction temperatures, or easier separations (as, unlike THF, it is not miscible with water). It is derived from sugars via furfural and is occasionally touted as a biofuel.

Reductions with hydrosilanes are methods used for hydrogenations and hydrogenolysis of organic compounds. The approach is a subset of Ionic hydrogenations. In this particular method, the substrate is treated with a hydrosilane and auxiliary reagent, often a strong acid, resulting in formal transfer of hydride from silicon to carbon. This style of reduction with hydrosilanes enjoys diverse if specialized applications.

<span class="mw-page-title-main">Methoxymethylfurfural</span> Chemical compound

Methoxymethylfurfural is an organic compound derived from dehydration of sugars and subsequent etherification with methanol. This colorless liquid is soluble in a wide range of solvents including lower alcohols. The molecule is a derivative of furan, containing both aldehyde and ether (methoxymethyl) functional groups. MMF has been detected in the leaves and roots of Chilean Jaborosa magellanica (Solanaceae). It has a typical odor suggestive of maraschino cherries. MMF can be made from a wide range of carbohydrate containing feedstocks including sugar, starch and cellulose using a chemical catalytic process and is a potential "carbon-neutral" feedstock for fuels and chemicals.

Dionisios G. Vlachos is an American chemical engineer, the Allan & Myra Ferguson Endowed Chair Professor of Chemical Engineering at the University of Delaware and director of the Catalysis Center for Energy Innovation, a U.S. Department of Energy - Energy Frontiers Research Center. Throughout his career at University of Delaware and the University of Minnesota, he has advanced the study of catalysts and reaction engineering including catalytic applications in biomass utilization, alkane conversion and zeolites. He is a fellow of the American Association for the Advancement of Science and recipient of the Wilhelm Award of the American Institute of Chemical Engineers (2011).

References

  1. 1 2 3 Baird, Zachariah Steven; Uusi-Kyyny, Petri; Pokki, Juha-Pekka; Pedegert, Emilie; Alopaeus, Ville (6 Nov 2019). "Vapor Pressures, Densities, and PC-SAFT Parameters for 11 Bio-compounds". International Journal of Thermophysics. 40 (11): 102. doi: 10.1007/s10765-019-2570-9 .
  2. NIST Chemistry WebBook. http://webbook.nist.gov
  3. Kenneth Barbalace. "Chemical Database - 2-Methylfuran. EnvironmentalChemistry.com. 1995 - 2008. Accessed on-line: 8/26/2008" . Retrieved 2008-08-26.
  4. Jim Duke. "Dr. Duke's Phytochemical and Ethnobotanical Databases. [Online Database] 26 August 2008. 2-METHYL-FURAN". Archived from the original on 2016-11-18. Retrieved 2008-08-26.
  5. "2-methyl furan". The Good Scents Company. Retrieved 2008-08-26.
  6. L. W. Burnette, et al., "Production of 2-Methylfuran by Vapor Phase Hydrogenation of Furfural" Industrial and engineering Chemistry, V40, P502-505 (1948).