Prenol

Structural formula
General
Surname	Prenol
other names	3-methyl-2-buten-1-ol; 3,3-dimethylallyl alcohol; gamma, gamma-dimethylallyl alcohol; 3-methylbut-2-en-1-ol; 1-hydroxy-3-methyl-2-butene;
Molecular formula	C 5 H 10 O
Brief description	colorless liquid with a fruity odor
External identifiers / databases
EC number	209-141-4
ECHA InfoCard	100.008.312
PubChem	11173
Wikidata	Q425512
properties
Molar mass	86.13 g mol −1
Physical state	liquid
density	0.85 g cm −3
boiling point	140 ° C
Vapor pressure	1.4 mbar (20 ° C)
solubility	easily soluble in water (170 g l −1 at 20 ° C)
Refractive index	1.443 (20 ° C)
safety instructions
H and P phrases	H: 226-302-314
	P: 261-305 + 351 + 338
Toxicological data	810 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

Prenol ( 3-methyl-2-buten-1-ol ) is a chemical compound from the group of alkenols , more precisely the methylbutenols .

Extraction and presentation

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

Following the resulting isoprenol at temperatures of 50-110 ° C and pressures of 2-20 bar is to palladium - catalysts which on activated carbon isomerized to prenol are supported.

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

properties

Prenol is an inflammable colorless liquid with a fruity odor, which is easily soluble in water.

Occurrence and use

Prenol occurs as a building block in the biogenesis and industrial production of isoprenoids (polyprenols).

safety instructions

The vapors of Prenol can form an explosive mixture with air ( flash point 50 ° C, ignition temperature 305 ° C).

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on 3-methyl-2-buten-1-ol in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .
↑ ^a ^b Data sheet 3-Methyl-2-buten-1-ol, 99% from Sigma-Aldrich , accessed on January 29, 2019 ( 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 .
↑ Martine Dehn, Bernhard Brunner, Klaus Ebel, Sabine Huber: PROCESS FOR PRODUCING PRENOL AND PRENAL FROM ISOPRENOL. In: freepatentsonline.com. BASF SE, March 14, 2019, accessed on July 27, 2019 .

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on 3-methyl-2-buten-1-ol in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .

[Sigma-2] Data sheet 3-Methyl-2-buten-1-ol, 99% from Sigma-Aldrich , accessed on January 29, 2019 ( 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] Martine Dehn, Bernhard Brunner, Klaus Ebel, Sabine Huber: PROCESS FOR PRODUCING PRENOL AND PRENAL FROM ISOPRENOL. In: freepatentsonline.com. BASF SE, March 14, 2019, accessed on July 27, 2019 .