Basf Aktiengesellschaft

Michael Horner

Axel Nissen

Matthias Irgang

Gernot Teege

Dieter Horn

Erik Lueddecke

Gerd Kaibel

Hubert Trauth

Albert Hettche

Werner Aquila

Werner Fliege

Gerd Heilen

Stefan Weiss

Peter Lechtken

Walter Rebafka

Wolfgang Koernig

Guenter Boettger

Peter R Laurer

Heinrich Pasedach

Distillative separation of liquid mixtures of one or more water-insoluble substances which have boiling points higher than that of water and one or more substances which have boiling points lower than that of water or which form azeotropes having boiling points lower than that of water, wherein the mixture to be distilled is mixed with a quantity of water such that the boiling point of the water under the pressure applied limits the bottom temperature of the mixture of substances to be separated.

Distillative separation of liquid mixtures of substances

Stabilizers consisting of (a) 2,5,7,8-tetramethyl-2-(2'-stearyloxyethyl)-chroman and (b) glyceryl stearate, glyceryl hydroxystearate, partial esters of stearic acid with condensates of glycerol and trimethylolpropane, triglyceryl stearate and/or tetraglyceryl stearate, with or without further conventional additives, the weight ratio of (a) to (b) being from 10:1 to 1:10, give improved stabilization to discoloration and superior stability during processing when used in plastics such as polyethylene or polypropylene.

Stabilizers

Ruthenium-on-charcoal and ruthenium-on-carbon black catalysts, containing from 0.1 to 5% by weight of iron, for the preparation of olefinically unsaturated alcohols by selective hydrogenation of the corresponding .alpha., .beta.-unsaturated carbonyl compounds in the liquid phase are prepared by modifying the catalyst with iron only after it has been impregnated with the ruthenium compound, and reducing the catalyst with hydrogen at from 400.degree. to 600.degree. C., with thorough mixing. The catalysts according to the invention are particularly useful for improving the industrially difficult hydrogenation of citral to give the soughtafter fragrances geraniol and nerol.

Selective hydrogenation of unsaturated carbonyl compounds

Chroman derivatives of the general formula I ##STR1## where R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each H or C.sub.1 -C.sub.4 -alkyl, R.sup.5 is C.sub.10 -C.sub.30 -alkyl or C.sub.10 -C.sub.30 -alkenyl, X and Y are each O, NH or S, m is 0, 1, 2 or 3 and n and r are each 0 or 1, the preparation of compounds I by various methods known per se, and the use of the compounds as stabilizers for organic materials.

Chroman derivatives and stabilized polypropylene composition

Ruthenium-on-charcoal and ruthenium-on-carbon black catalysts, containing from 0.1 to 5% by weight of iron, for the preparation of olefinically unsaturated alcohols by selective hydrogenation of the corresponding .alpha.,.beta.-unsaturated carbonyl compounds in the liquid phase are prepared by modifying the catalyst with iron only after it has been impregnated with the ruthenium compound, and reducing the catalyst with hydrogen at from 400.degree. to 600.degree. C., with thorough mixing. The catalysts according to the invention are particularly useful for improving the industrially difficult hydrogenation of citral to give the sought-after fragrances geraniol and nerol.

Ruthenium-on-charcoal and ruthenium-on-carbon black hydrogenation

Olefinically unsaturated alcohols (I) are prepared by selective hydrogenation of the corresponding carbonyl compounds (II) in the liquid phase with hydrogen, using an Ru, Rh, Os, Ir or Pt catalyst and carrying out the hydrogenation in the presence of from 5 to 40% by weight, based on (II), of a tertiary amine. The process is of particular importance for the selective hydrogenation of .alpha.,.beta.-unsaturated carbonyl compounds (IIa) and amongst these specifically for the hydrogenation of citral to geraniol and nerol. The preferred amine is trimethylamine.

Preparation of unsaturated alcohols

Novel chroman derivatives ##STR1## where R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are each H or C.sub.1 -C.sub.4 -alkyl, R.sup.6 and R.sup.7 are each H, C.sub.1 -C.sub.4 -alkyl or aryl, m is 1, 2 or 3, and R.sup.8 is alkyl or alkenyl of up to 30 carbon atoms, the preparation of these compounds, and their use as stabilizers for organic materials.

Chroman derivatives useful as stabilizers for polypropylene and

Novel chroman derivatives ##STR1## where R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each H or C.sub.1 -C.sub.4 -alkyl, R.sup.5 is sec.--C.sub.3 -C.sub.8 --alkyl or tert.--C.sub.4 -C.sub.8 --alkyl, R.sup.6 is H or R.sup.5, m is 1, 2 or 3, and n is 0, 1, 2 or 3, a process for the preparation of these compounds, and their use as stabilizers for plastics.

Chroman-6-ol derivatives useful for stabilizing plastics

4-(2,5-Dihydroxyphen-1-yl)-crotonic acid and its derivative (I) ##STR1## where R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each H or C.sub.1 -C.sub.8 -alkyl, R.sup.5 is H, C.sub.1 -C.sub.30 -alkyl or C.sub.2 -C.sub.30 -alkenyl, and R' is H or an organic radical which can be split off hydrogenolytically, and a process for the preparation of the compounds I, wherein a hydroquinone II ##STR2## is reacted, in the presence of from 0.1 to 2 moles of a Lewis acid per mole of II, with

4-(2,5-Dihydroxyphen-1-yl)-crotonic acid and its derivatives, and the

2-Hydroxyalkylchromans (I) ##STR1## where R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each H or C.sub.1 -C.sub.8 -alkyl, R' is H or an organic radical which can be split off hydrolytically or hydrogenolytically as R'-OH or R'-COOH, and m is 1, 2 or 3, are prepared by reacting a hydroquinone II ##STR2## (a) with an alkenediol IIIa ##STR3## or (b) with an alkenediol IIIb ##STR4## or (c) with an alkenediol IIIc ##STR5## where R.sup.4' is a radical which during the condensation with II is converted to the radical R.sup.4, at from -50.degree. C. to 120.degree. C., in an inert solvent, in the presence of from 10 to 300 mole %, based on II, of a Lewis acid or of an adduct of a Lewis acid with a Lewis base which has a lower basicity than compound II.

Preparation of 2-hydroxyalkylchromans

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.

Preparation of olefinically unsaturated carbonyl compounds and alcohol

Saturated aliphatic, cycloaliphatic and araliphatic aldehydes are prepared by selective hydrogenation of the corresponding olefinically unsaturated aldehydes with hydrogen in the liquid phase over a palladium-containing catalyst, using a catalyst system in which the active constituents are from 2 to 90% by weight of palladium and from 10 to 98% by weight of an oxide or a salt of a rare earth metal or of a mixture of different oxides and/or salts of this type.

Preparation of saturated aliphatic, cycloaliphatic and araliphatic

Chromane derivatives (I) ##STR1## where R.sup.1, R.sup.2 and R.sup.3 are H or C.sub.1 -C.sub.8 -alkyl, R.sup.4 is H, C.sub.1 -C.sub.8 -alkyl or C.sub.1 -C.sub.8 -acyl and R.sup.5 is C.sub.1 -C.sub.8 -alkyl are prepared by reacting a hydroquinone (II) ##STR2## with a Lewis acid or a Lewis acid derivative having the same action, and with a nitrile CH.sub.2 .dbd.CH--C(R.sup.5)(OR.sup.6)CN (III), where R.sup.6 is H, C.sub.1 -C.sub.4 -acyl or C.sub.1 -C.sub.4 -alkyl, or with a compound from which III is formed in situ, in the presence of an inert solvent.

Preparation of chromane derivatives

Carbonyl compounds R.sup.1 --CHR.sup.2 --CHR.sup.3 --CR.sup.4 O (I, R.sup.1 =H or an organic radical; R.sup.2 -R.sup.4 =H or C.sub.1 -C.sub.4 -alkyl) are prepared by selective hydrogenation of the .alpha.,.beta.-unsaturated carbonyl compounds R.sup.1 --CR.sup.2 =CR.sup.3 --CR.sup.4 O (II) in the liquid phase by means of hydrogen in the presence of a palladium catalyst and of from 15 to 50% by weight, based on (II), of a tertiary amine.

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Neustadt, Germany

Michael Horner