Composition that includes cyclohexyl-substituted tertiary alkanols

Abstract

The present invention relates to processes for the preparation of compounds of the formula (Ia) ##STR00001##
by reacting styrene with a secondary alkanol and the hydrogenation of the resulting phenyl-substituted tertiary alkanol. In addition, the invention relates to compounds of the formula (Ia) and to the use of such compounds as fragrances, and also to compositions which comprise compounds of the formulae (Ia) and (Ib).

Claims

1. A method for improving the olfactory properties and/or concealing undesired intrinsic odors of a cosmetic composition, textile detergent or cleaner for hard surfaces, the method comprising adding a compound of formula (Ia) to the cosmetic composition, the textile detergent or the cleaner for hard surfaces, ##STR00013## wherein R.sub.1 and R.sub.2, independently of one another, are selected from C.sub.4-7-cycloalkylalkyl- with a total of 4 to 7 carbon atoms, C.sub.3-7-cycloalkyl-, which is optionally substituted with 1, 2, or 3 C.sub.1-7-alkyl, and C.sub.1-7-alkyl-, and R.sub.1 and R.sub.2 together comprise in total 3 to 11 carbon atoms.

2. The method according to claim 1, wherein R.sup.1 and R.sup.2, independently of one another, are selected from C.sub.1-7-alkyl-.

3. The method according to claim 1, wherein R.sup.1 is methyl and R.sup.2 is ethyl.

4. The method according to claim 1, wherein R.sup.1 and R.sup.2 together comprise in total 3 to 5 carbon atoms.

5. The method according to claim 1, wherein the adding of the compound of formula (Ia) includes adding a compound of formula (Ib) ##STR00014##

6. The method according to claim 1, wherein R.sup.1 and R.sup.2, independently of one another, are selected from C.sub.1-7-alkyl, and C.sub.4-7-cycloalkylalkyl- with a total of 4 to 7 carbon atoms.

7. The method according to claim 1, wherein R.sup.1 and R.sup.2, independently of one another, are selected from C.sub.1-7-alkyl, and C.sub.3-7-cycloalkyl-, which is optionally substituted with 1, 2, or 3 C.sub.1-7-alkyl.

8. The method according to claim 2, wherein the compound of formula (1a) is selected from the from consisting of 1-cyclohexyl-3-methyl-3-hexanol, 1-cyclohexyl-3-methyl-3-heptanol, 1-cyclohexyl-3-methyl-3-octanol, 1-cyclohexyl-3-methyl-3-nonanol, 1-cyclohexyl-3,4-dimethyl-3-octanol, 1-cyclohexyl-3,5-dimethyl-3-octanol, 1-cyclohexyl-3,6-dimethyl-3-octanol, 1-cyclohexyl-3,7-dimethyl-3-octanol, 1-cyclohexyl-3,4,4-trimethyl-3-heptanol, 1-cyclohexyl-3,5,5-trimethyl-3-heptanol, 1-cyclohexyl-3,6,6-trimethyl-3-heptanol, 1-cyclohexyl-5-ethyl-3-methyl-3-heptanol, 1-cyclohexyl-3,5-dimethyl-3-heptanol, 2,4-dicyclohexyl-2-methyl-2-butanol, 1-cyclohexyl-4-cyclopentyl-3-methyl-3-pentanol, 1-cyclohexyl-3-ethyl-3-hexanol, 1-cyclohexyl-3-ethyl-3-heptanol, 1-cyclohexyl-3-ethyl-3-octanol, and 1-cyclohexyl-3-ethyl-3-nonanol.

Description

Example 1

Preparation of the Hydrogenated Catalyst

(1) The support material used was a spherical SiO.sub.2 support (type AF125 from BASF SE) with a sphere diameter of 3 to 5 mm and a bulk density of 0.49 kg/l. The BET surface area was 337 m2/g, the water absorption (WA) was 0.83 ml/g. For the impregnation, a 14.25% by weight ruthenium(III) acetate solution in acetic acid (from Umicore) was used.

(2) 200 g of support were introduced as initial charge into a round-bottomed flask. 15 g of the ruthenium acetate solution were diluted to 150 ml with distilled water (90% WA). The support material was introduced as initial charge into the distillation column of a rotary evaporator and the first quarter of the solution was pumped onto the support material with a slight vacuum at 3 to 6 rpm. When the addition was complete, the support was left in the rotary evaporator for a further 10 minutes at 3 to 6 rpm in order to homogenize the catalyst. This impregnation/homogenization step was repeated three times until all of the solution had been applied to the support. The support material treated in this way was dried under agitation in the rotary dryer at 140° C., then reduced for 3 h at 200° C. in a stream of hydrogen (20 l/h H.sub.2; 10 l/h N.sub.2) and passivated at 25° C. (5% air in N.sub.2, 2 h). The resulting catalyst A according to the invention comprised 0.34% by weight of ruthenium, based on the total weight of the catalyst.

Step A

Example 2

Preparation of 3-Methyl-1-Phenyl-3-Pentanol

(3) The reaction of styrene and 2-butanol was carried out in a continuously operated laboratory plant. This comprised a 300 ml autoclave which was operated with pressure regulation. Thus, the amount removed corresponded at all times to the amount introduced. The removed reaction mixture was cooled, decompressed and collected in a discharge container.

(4) A solution of styrene in 2-butanol (20% by weight, 100 g/h) was pumped continuously at an average temperature of 390° C. in the reactor through the laboratory plant. The conversion of styrene was 84.0% and, in the steady state, 14.7 g/h of 3-methyl-1-phenyl-3-pentanol were obtained.

Step B

Example 3

Preparation of 1-Cyclohexyl-3-Methyl-3-Pentanol

(5) A 300 ml autoclave was initially charged with 5.6 g of 3-methyl-1-phenyl-3-pentanol, dissolved in 94.4 g of tetrahydrofuran, and 1.6 g of a catalyst prepared according to Example 1 (0.35% ruthenium on silicon dioxide). The autoclave was flushed three times with nitrogen and then hydrogenated for 10 hours at 160° C. and a hydrogen pressure of 160 bar. The product was analyzed by gas chromatography (polydimethylsiloxane DB1, 30 m, internal diameter: 0.25 mm, film thickness: 0.25 μm, 50° C., 5 min isotherm, −6° C./min, 290° C., 219 min isotherm). The conversion was 99.9%, the selectivity 93%.