Isoprenol

Structural formula
General
Surname	Isoprenol
other names	3-methylbut-3-en-1-ol ( IUPAC ); 3-methyl-3-buten-1-ol; 3-isobutenyl carbinol; Methallyl carbinol;
Molecular formula	C 5 H 10 O
Brief description	colorless liquid with an alcohol-like odor
External identifiers / databases
EC number	212-110-8
ECHA InfoCard	100.011.009
PubChem	12988
Wikidata	Q408094
properties
Molar mass	86.13 g mol −1
Physical state	liquid
density	0.86 g cm −3
Melting point	−20 ° C
boiling point	129 ° C
Vapor pressure	26.7 mbar (20 ° C)
solubility	soluble in water (90 g l −1 at 20 ° C)
Refractive index	1.433 (20 ° C)
safety instructions
H and P phrases	H: 226-318
	P: 280-305 + 351 + 338
	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

Isoprenol ( 3-methyl-3-buten-1-ol ) is a chemical compound from the group of alkenols .

Extraction and presentation

For the industrial synthesis of isoprenol, isobutene is reacted with liquid formaldehyde at temperatures of 200-300 ° C. and pressures of 250 bar in a reactor without a catalyst.

The product is worked up and purified by multi-stage distillation under pressure in rectification columns .

properties

3-Methyl-3-buten-1-ol is a flammable, volatile, colorless liquid with an alcoholic odor, which is soluble in water.

The OH group is in the homoallyl position in relation to the double bond .

use

3-Methyl-3-buten-1-ol is a building block in the biogenesis of isoprenoids . Senecioaldehyde can be obtained from isoprenol by air oxidation on a silver catalyst .

safety instructions

The vapors of 3-methyl-3-buten-1-ol can form an explosive mixture with air ( flash point 42 ° C, ignition temperature 345 ° C).

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k Entry on 3-methyl-3-buten-1-ol in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .
↑ Data sheet 3-methyl-3-buten-1-ol, ≥ 97% from Sigma-Aldrich , accessed on December 6, 2011 ( PDF ).
↑ ^a ^b H. Pommer, A. Nürrenbach: INDUSTRIAL SYNTHESIS OF TERPENE COMPOUNDS. In: Organic Synthesis . 1975, pp. 527-551, doi : 10.1016 / B978-0-408-70725-1.50016-1 . ISBN 978-0-408-70725-1 (book chapter)
↑ Hans Martin Weitz, Eckhard Loser: Isoprene . In: Ullmann's Encyclopedia of Industrial Chemistry . Wiley ‐ VCH Verlag GmbH & Co. KGaA., June 15, 2000, p. 86, doi : 10.1002 / 14356007.a14_627 .
↑ K. Hüsnü, Can Başer, Gerhard Buchbauer: Handbook of Essential Oils: Science, Technology, and Applications , 2nd edition, Boca Raton, 2016, ISBN 978-1-4665-9046-5 , p. 192 ( limited preview in Google Book Search).
↑ Patent application WO2008037693 : Continuous process for the production of citral. Registered on September 26, 2006 , published on April 3, 2008 , applicant: BASF SE, inventor: Günter Wegner, Gerd Kaibel, Jörg Therre, Werner Aquila and Hartwig Fuchs. ‌

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k Entry on 3-methyl-3-buten-1-ol in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .

[Sigma-2] Data sheet 3-methyl-3-buten-1-ol, ≥ 97% from Sigma-Aldrich , accessed on December 6, 2011 ( PDF ).

[VERFAHREN-3] H. Pommer, A. Nürrenbach: INDUSTRIAL SYNTHESIS OF TERPENE COMPOUNDS. In: Organic Synthesis . 1975, pp. 527-551, doi : 10.1016 / B978-0-408-70725-1.50016-1 . ISBN 978-0-408-70725-1 (book chapter)

[ULLMANN-4] Hans Martin Weitz, Eckhard Loser: Isoprene . In: Ullmann's Encyclopedia of Industrial Chemistry . Wiley ‐ VCH Verlag GmbH & Co. KGaA., June 15, 2000, p. 86, doi : 10.1002 / 14356007.a14_627 .

[5] K. Hüsnü, Can Başer, Gerhard Buchbauer: Handbook of Essential Oils: Science, Technology, and Applications , 2nd edition, Boca Raton, 2016, ISBN 978-1-4665-9046-5 , p. 192 ( limited preview in Google Book Search).

[6] Patent application WO2008037693 : Continuous process for the production of citral. Registered on September 26, 2006 , published on April 3, 2008 , applicant: BASF SE, inventor: Günter Wegner, Gerd Kaibel, Jörg Therre, Werner Aquila and Hartwig Fuchs. ‌