Preparation of olefinically unsaturated carbonyl compounds and alcohol

US4320228A · kind A · utility

Assignee

• BASF SE

Inventors

• Michael Horner · Neustadt, DE
• Matthias Irgang · Heidelberg, DE
• Axel Nissen

Key dates

• Filing date: Jul 8, 1980
• Grant date: Mar 16, 1982
• Expiry date: Jul 8, 2000

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07B2200/09
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Olefinically unsaturated carbonyl compounds R.sup.1 --CHR.sup.2 --CHR.sup.3 --C(R.sup.4)O (I) and alcohols R.sup.1 --CHR.sup.2 --CHR.sup.3 --CH(R.sup.4)--OH (II) (where R.sup.1 is an olefinically unsaturated organic radical, and R.sup.2, R.sup.3 and R.sup.4 are H or C.sub.1 -C.sub.4 -alkyl) are prepared by hydrogenating the carbonyl compounds R.sup.1 --CR.sup.2 .dbd.CR.sup.3 --C(R.sup.4)O (III) in the liquid phase with hydrogen, using a catalyst system comprising, firstly, Pd and, secondly, Ru, Rh, Os, Ir or Pt, in the presence of from 5 to 40% by weight, based on (III), of a tertiary amine, under a hydrogen pressure of from 1 to 20 bar is predominantly (I) is to be obtained and from 20 to 150 bar if predominantly (II) is to be obtained. The process is of particular importance for the hydrogenation of citral (IIIa) to give citronellal (Ia) or citronellol (IIa), the preferred amine being trimethylamine.