2-methylfuran

Structural formula
General
Surname	2-methylfuran
other names	Silvan
Molecular formula	C 5 H 6 O
Brief description	colorless liquid with an ethereal odor
External identifiers / databases
EC number	208-594-5
ECHA InfoCard	100.007.814
PubChem	10797
Wikidata	Q209438
properties
Molar mass	82.10 g mol −1
Physical state	liquid
density	0.91 g cm −3
Melting point	−89 ° C
boiling point	64 ° C
Vapor pressure	139 mbar (20 ° C)
solubility	sparingly soluble in water (3 g l −1 at 20 ° C)
Refractive index	1.4332 (20 ° C, 589 nm)
safety instructions
H and P phrases	H: 225-301-330
	P: 210-233-240-304 + 340-308 + 310-403 + 235
Toxicological data	167 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

2-Methylfuran is a chemical compound belonging to the furans group and is isomeric to 3-Methylfuran .

Occurrence

2-methylfuran occurs naturally in the form of an odor component in cigarette smoke and mold.

Extraction and presentation

2-Methylfuran can be obtained by a palladium- catalyzed reaction of penta-1,3-diene with hydrogen peroxide .

Industrially, 2-methylfuran is produced from furfuryl alcohol by catalytic hydrogenation with a copper catalyst in the vapor phase .

properties

2-Methylfuran is a volatile, colorless liquid with an ethereal odor that is sparingly soluble in water. It decomposes when heated strongly and has a dynamic viscosity of 4 mPa · s at 20 ° C.

use

2-Methylfuran was used as a high octane gasoline additive during World War II . It is also used to produce 2-methylthiophene .

safety instructions

The vapors of 2-methylfuran form an explosive mixture with air (flash point −22 ° C).

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k Entry on 2-methylfuran in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .
↑ ^a ^b Data sheet 2-methylfuran (PDF) from Merck , accessed on October 12, 2012.
↑ Wolfgang Legrum: Fragrances, between stench and fragrance . Springer DE, 2011, ISBN 3-8348-1245-5 , p. 67 ( limited preview in Google Book search).
^ CW Jones: Applications of Hydrogen Peroxide and Derivatives . Royal Society of Chemistry, 1999, ISBN 0-85404-536-8 , pp. 102 ( limited preview in Google Book search).
↑ Patent US6852868 : Catalytic hydrogenation of furfural to produce 2-methylfuran and 2-methyltetrahydrofuran, using a reduced copper based catalyst. Filed August 21, 2002 , published February 8, 2005 , applicant: Pure Energy Corporation, inventor: Irshad Ahmed. ‌
↑ Peter Kurzweil, Paul Scheipers: Chemistry: Fundamentals, structural knowledge, applications and experiments . Springer DE, 2012, ISBN 3-8348-1555-1 , p. 274 ( limited preview in Google Book search).
^ KB Wiberg, HF McShane: 2-Chloromethylthiophene In: Organic Syntheses . 29, 1949, p. 31, doi : 10.15227 / orgsyn.029.0031 ; Coll. Vol. 3, 1955, p. 197 ( PDF ).

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k Entry on 2-methylfuran in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .

[Merck-2] Data sheet 2-methylfuran (PDF) from Merck , accessed on October 12, 2012.

[Wolfgang_Legrum-3] Wolfgang Legrum: Fragrances, between stench and fragrance . Springer DE, 2011, ISBN 3-8348-1245-5 , p. 67 ( limited preview in Google Book search).

[C._W._Jones-4] CW Jones: Applications of Hydrogen Peroxide and Derivatives . Royal Society of Chemistry, 1999, ISBN 0-85404-536-8 , pp. 102 ( limited preview in Google Book search).

[5] Patent US6852868 : Catalytic hydrogenation of furfural to produce 2-methylfuran and 2-methyltetrahydrofuran, using a reduced copper based catalyst. Filed August 21, 2002 , published February 8, 2005 , applicant: Pure Energy Corporation, inventor: Irshad Ahmed. ‌

[Peter_Kurzweil,_Paul_Scheipers-6] Peter Kurzweil, Paul Scheipers: Chemistry: Fundamentals, structural knowledge, applications and experiments . Springer DE, 2012, ISBN 3-8348-1555-1 , p. 274 ( limited preview in Google Book search).

[7] KB Wiberg, HF McShane: 2-Chloromethylthiophene In: Organic Syntheses . 29, 1949, p. 31, doi : 10.15227 / orgsyn.029.0031 ; Coll. Vol. 3, 1955, p. 197 ( PDF ).