FI86056B - 2-METHYLECANALOXY OCH DESS ANVAENDNING. - Google Patents

Description

The invention relates to a novel chemical compound 2-methyldecanal oxime (1-oximino-2-methyldecane) and its use.

The oximes have the general formula R2

c ^ c = NOH

R '

Aldoximes are compounds in which R1 is an organic radical and R2 = H; in ketoximes R1 and R2 are organic radicals.

The oxines can be prepared according to various methods 10. The most useful method is the reaction of aldehydes or ketones with hydroxylamine or hydroxylamine salts. This reaction usually proceeds very quickly and completely. Since oximes can also be easily cleaved again, they are often prepared for the identification, protection, isolation and purification of carbonyl compounds according to said method.

Other oxime syntheses start from olefins to which NOCl is still attached. Oxidation of aliphatic, primary amines ... and reduction of nitro compounds also leads to oximes.

• .20 Particularly suitable for the preparation of ketoximes is the nitrosation of ketones followed by the isomerization of an internally formed nitroso compound.

In addition to the isolation and purification of carbonyl compounds already mentioned, oximes have use as antioxidants in paints and varnishes, as an additive in lubricating oils to reduce: precipitation and as an additive in traction fluids. ' Furthermore, they are suitable as additives for bleaching polyamide fibers and for dyeing textile fibers.

2 86056

Oximes are still desired intermediates in the manufacture of valuable end products. In the foreground, according to the subject, is the production of polyamides from lactams, which in turn are obtained from oximes by Beckmann precipitation. Furthermore, oximes 5 can be converted by dehydration or thermal decomposition to nitriles and hydrogenation to amines.

The new compound 2-methyldecanal oxime is obtained from 2-methyldecanal by reaction with hydroxylamine or a hydroxylamine salt. 2-Methyldecanal can be obtained by hydroformy-10 weaving from decene-1; here it is formed along the undecanal. In order to separate the isomers, it has been found appropriate to include formaldehyde in the reaction mixture. In this case, the n-undecanal form is formed by the removal of water from 2-methylene undecanal, which is partially hydrogenated to 2-methylinonylacetaldehyde and separated by distillation from 2-methyldecanal, which does not react with formaldehyde.

To prepare the oxime, the aldehyde is reacted with an aqueous solution of hydroxylamine having a concentrate of 12-20, in particular 15-17% by weight of hydroxylamine (from solution). If starting from a hydroxylamine salt, so much hydroxide must be added to the solution that its pH is about 7. It is expedient to use hydroxylamine or a salt thereof in excess of the aldehyde; an excess of at least 10, preferably 15-25% of the stoichiometric amount has been found to be advantageous. The reaction is carried out at a temperature of t ": 50-90 ° C, preferably 70-85 ° C. It is completed in about 30-90 minutes, independently of the selected temperature. The aqueous phase and the organic phase are separated. The organic phase washed with water to remove dissolved salts, the water is removed .30 and optionally distilled under reduced pressure.

2-Methyldecanal is a clear, slightly viscous liquid at room temperature with a boiling point of about 255 ° C and a melting point of V- ° C.

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II

3 86056 2-Methyldecanal oxime is a remarkable fragrance which surprisingly has approximately the same odor value as its underlying aldehyde. Methyloctylacetaldehyde is disclosed in No. 2145 in "Perfume and Flavor Chemicals", 5 by Steffen Arctander (1969), Montclair N.Y. Its aroma is described as strong, fresh, dry, citrusy. Unlike aldehyde, oxime is also stable in alkaline environments. It is therefore ideally suited as a fragrance or ingredient in fragrance compositions 10 for detergents and soaps.

The following example describes a preparation method for a novel compound.

Example 98.5 g (0.6 mol of salt vs. 1.2 mol of hydroxylamine) of hydroxylamine sulphate in a 20% strength by weight aqueous solution are mixed with 40 g (1 mol) of NaOH (33% by weight). 170.3 g (1 mol) of 2-methyldecanal are added over 30 minutes to the resulting solution.

The mixture is heated to 80 ° C and stirred at this temperature for 20 hours. Finally, the aqueous phase and the organic phase are separated. The organic phase is washed twice with 150 ml of water each time, dehydrated ... by centrifugation or passing through a hydrophobic filter and possibly distilled. The yield, based on the aldehyde used, is 99.4% of theory.

Analysis: 'obtained calculated.

C 71.23 71.35 h: H: 12.43 12.39 · N 7.56 7.56% ·. •• .1.30 The figure shows the IR spectrum of the new compound.

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Claims (2)

4,86056 1. Chemical preparation of 2-methyldecanaloxime. 1. The chemical compound 2-methyldecananoxime. 2. Use of 2-methyldecanal oxime as a perfume. * 2. Användning av 2-methyldecanaloxim som lampämne. 1 ·