2- sec -butylphenol

Structural formula
Simplified structural formula without stereochemistry
General
Surname	2-sec-butylphenol
other names	o - (sec-butyl) phenol o - (1-methylpropyl) phenol 2- (1-methylpropyl) phenol
Molecular formula	C 10 H 14 O
Brief description	colorless to yellowish liquid with a phenolic odor
External identifiers / databases
CAS number 89-72-5 ( racemate ) 159650-89-2 ( S ) -2- sec -butylphenol 36383-18-3 ( R ) -2- sec -butylphenol EC number 201-933-8 ECHA InfoCard 100,001,758 PubChem 6984 Wikidata Q20156241
properties
Molar mass	150.22 g mol −1
Physical state	liquid
density	0.982 g cm −3
Melting point	12 ° C
boiling point	226-228 ° C
Vapor pressure	0.08 hPa (20 ° C)
solubility	sparingly soluble in water (1.46 g l −1 at 20.1 ° C)
safety instructions
GHS labeling of hazardous substances danger H and P phrases H: 302-314 P: 280-305 + 351 + 338-310
Toxicological data	5560 mg kg −1 ( LD 50 ,  rabbit ,  transdermal ) 320 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 .

2- sec -Butylphenol is an aromatic compound from the group of alkylphenols .

Isomers

2- sec -Butylphenol has a stereocenter and is consequently a chiral compound of which there are two isomers , ( R ) -2- sec -Butylphenol and ( S ) -2- sec -Butylphenol.

Unless expressly stated otherwise in this text or in the scientific literature, "2- sec -Butylphenol" is the racemate, i.e. the 1: 1 mixture of ( R ) -2- sec -Butylphenol and ( S ) -2- sec -butylphenol.

Isomers of 2-sec-butylphenol
Surname	( S ) -2- sec -butylphenol	( R ) -2- sec -butylphenol
other names	(+) - 2- sec -Butylphenol	(-) - 2- sec -butylphenol
Structural formula
CAS number	159650-89-2	36383-18-3
	89-72-5 (racemate)
EC number	-	-
	201-933-8 (racemate)
ECHA info card	-	-
	100.001.758 (racemate)
PubChem	5325936	7000004
	6984 (racemate)
Wikidata	Q28600794	Q27115978
	Q20156241 (racemate)

Extraction and presentation

2- sec -Butylphenol is industrially produced by a Friedel-Crafts alkylation of phenol with 1-butene (or 2-butene ) at temperatures of 250-300 ° C. and pressures of 35-80 bar on acidic gamma-aluminum oxide contacts as Catalyst made.

The catalyst is finely suspended in a discontinuous process . In the liquid phase, stirred tank reactors are used and phenol is used in an approximately four-fold excess. The selectivity for 2- sec- butylphenol reached 95%. Small amounts of 4 sec -butylphenol and sec -butylphenyl ether are also formed as by-products .

properties

2- sec -Butylphenol is a flammable, hardly inflammable, colorless to yellowish liquid with a phenol-like odor, which is sparingly soluble in water.

use

2- sec -Butylphenol is used as an intermediate in the manufacture of insecticides , acaricides , herbicides and other chemical compounds.

safety instructions

The vapors of 2- sec -butylphenol can form an explosive mixture with air ( flash point 112 ° C, ignition temperature 270 ° C).

Individual evidence

1. ↑ ^{a b c d e f g h i j k l m} entry on 2-sec-butylphenol in the GESTIS substance database of the IFA , accessed on December 6, 2016(JavaScript required) .
2. ↑ ^{a b c} Helmut Fiege, Heinz ‐ Werner Voges, Toshikazu Hamamoto, Sumio Umemura, Tadao Iwata, Hisaya Miki, Yasuhiro Fujita, Hans ‐ Josef Buysch, Dorothea Garbe, Wilfried Paulus: Phenol Derivatives. In: Ullmann's Encyclopedia of Industrial Chemistry . Wiley ‐ VCH Verlag GmbH & Co. KGaA., June 15, 2000, p. 17, doi : 10.1002 / 14356007.a19_313 .