Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
  • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
  • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
  • C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
  • C07C29/149—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases

Definitions

• the invention relates to unsaturated fatty alcohols which are obtained by fractionating palm fatty acid methyl esters and then hydrogenating the fraction of unsaturated long-chain methyl esters, and a process for the preparation of these fatty alcohols.
• Unsaturated fatty alcohols are important intermediates for a large number of products in the chemical industry, e.g. for the production of surfactants and main care products. An overview of this can be found, for example, by U.PIoog et ai. in Soap-Oil-Fat Waxes 109, 225 (1983). Their production is based on more or less unsaturated fatty acid methyl esters, which can be hydrogenated, for example, in the presence of chromium- or zinc-containing mixed catalysts [Ullmann's Enzyciopaedie der Technische Chemie, Verlag Chemie, Weinheim, 4th ed., Vol. 11, p.
• the prior art is a large-scale process, as has been carried out so far by the applicant, after which animal fats and oils are used which are obtained after the hydrogenation of unsaturated fatty alcohols at a bottom temperature of, for. B. 220 to 250 ° C and a reduced pressure of 1 to 20 mbar - measured at the top of the column - distilled. Since the production of unsaturated fatty alcohols is associated with high costs, distillation was carried out to minimize the loss of raw materials. In fact, a yield of approx. 90% of theory - and accordingly a loss of 10% - could be achieved in this way, but the products showed a distinct inherent smell. Another disadvantage is that the fatty alcohols of the prior art show unsatisfactory storage and cold behavior.
• unsaturated fatty alcohols with iodine numbers from 50 to 80 are particularly preferred since they have a solidification point which is favorable for use in cosmetic products.
• Unsaturated fat alcohols with iodine numbers in the above range are currently predominantly based on animal raw materials.
• the desired iodine number range is determined by cutting different products with different iodine number ranges.
• the setting of the iodine number range by distillative methods is not possible, since the iodine number or the iodine number range of fatty alcohols or fatty acids on an animal basis remains almost constant during the fractionation.
• animal fats have the disadvantage that they are built up very heterogeneously.
• animal fats contain nitrogenous compounds such as amides or steroids, such as. B. cholesterol, which are directly or indirectly responsible for the above-mentioned unpleasant smell of the products.
• the nitrogen-containing compounds can undergo side reactions, which worsens the product stability, in particular the oxidation stability, and leads to discolored products.
• consumers are extremely critical of products that are produced using beef tallow in view of the ongoing BSE discussion. There is therefore a constant need on the cosmetics market for ever purer and higher quality raw materials, a requirement which can usually only be provided by means of ever more complex technical processes and additional cleaning steps.
• unsaturated fatty alcohols there is a particular need for products with improved color and odor quality and more advantageous cold behavior.
• the known vegetable fatty alcohols have iodine numbers in the range below 20 or very high iodine numbers above 100.
• Fatty alcohols with iodine numbers in the range from 20 to 95 which is particularly preferred in terms of application technology are not known. Blending the fatty alcohols with very different iodine numbers does not lead to satisfactory products.
• a process is known from German published patent application DE-A1 4335781 (Henkel) in which the triglycerides contained in the vegetable fat raw materials are first split into glycerol and fatty acids by pressure splitting and the latter esterified with methanol or the starting materials are transesterified directly to the fatty acid methyl esters and then the esters are hydrogenated to give the alcohols, either the fatty acid methyl esters or the hydrogenation products being fractionated by taking off an amount such that the end product has an iodine number of 20 to 110 and a conjugate content of less than 4.5% by weight.
• the object of the present invention was therefore to provide unsaturated fatty alcohols based on palm oil, which have iodine numbers in the range from 65 to 85 and have greater oxidation stability and an equivalent or better low-temperature behavior compared to unsaturated fatty alcohols based on animals. At the same time, as pure as possible co-products should be obtained. Description of the invention
• the invention relates to unsaturated palm fatty alcohols with an iodine number in the range from 65 to 85, which essentially contain unsaturated fatty alcohols and mixtures of saturated fatty alcohols of the formula (I),
• R 1 represents a saturated or unsaturated, linear or branched alkyl radical having 14 to 20 carbon atoms, which is obtained by
• the process according to the invention also makes it possible to obtain unsaturated fatty alcohols in the iodine number range from 65 to 85 based on palm oil, which have high color and oxidation stability and excellent cold behavior; in addition, the products are practically odorless.
• Another advantage is that a very pure methyl palmitate fraction is obtained as an intermediate product, which can be processed separately.
• the invention further relates to a process for the production of unsaturated palm fatty alcohols with an iodine number in the range from 65 to 85, which essentially contain unsaturated fatty alcohols and mixtures of saturated fatty alcohols of the formula (I),
• R 1 represents a saturated or unsaturated, linear or branched alkyl radical having 14 to 20 carbon atoms
• the fractionation of the palm fatty acid methyl esters can be carried out batchwise or continuously under reduced pressure.
• the heating can be done for example by superheated steam, with a bottom temperature of, for. B. 220 to 250 ° C.
• the actual fractionation takes place in a packed column with low-pressure internals. Ordered sheet metal packs can be considered as internals. Further examples can be found in R ⁇ PP Chemie Lexikon, Thieme Verlag, Stuttgart, 9th edition, vol. 3, p. 2305 (1990) under the keyword “column internals" and in the literature mentioned there.
• the required fine vacuum of 1 to 20 mbar at the top of the column can be achieved, for example, using water ring pumps and upstream steam jets.
• the pressure drop across the entire distillation system should preferably not exceed 20 mbar. This gives a distillate with predominantly saturated Ci6 fractions and a bottom product with predominantly unsaturated Ci6 -C ⁇ s fractions.
• the weight ratio of distillate and bottom product is in the range from 30:70 to 35:65.
• the subsequent hydrogenation of the largely unsaturated methyl ester fraction obtained as the bottom to obtain the double bonds can be carried out in a manner known per se, i.e. for example in the presence of commercially available zinc / chromium catalysts, at temperatures in the range from 250 to 350 ° C and a hydrogen pressure of 200 to 275 bar.
• the conjugate content of the products is in the range from 6 to 12% by weight, the hydrocarbon content is less than 3, preferably less than 1% by weight.
• the unsaturated palm fatty alcohols according to the invention are low in color and odor and have a particularly advantageous low-temperature behavior. They are therefore suitable as raw materials for the production of washing, rinsing and cleaning products and products for hair and body care, in which they are present in amounts of 1 to 50, preferably 5 to 30% by weight, based on the composition can. example
• a technical palm fatty acid methyl ester was fractionated in a packed column with low-pressure internals at a bottom temperature of 200 ° C. and a head vacuum of 20 mbar, 30% by weight of methyl palmitate being obtained as distillate, while 70% by weight of a Ci6 / 18- Fatty acid methyl ester mixture remained, which had an iodine number of 74.
• the ester mixture from the bottom was transferred to an autoclave and reduced there with hydrogen to the mixture of the corresponding alcohols in the presence of commercially available zinc / chromium catalysts at 300 ° C. and 250 bar.
• the hydrogenation product freed from methanol had the following characteristics after gas chromatographic and wet chemical analysis:

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Fats And Perfumes (AREA)

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Citations (2)

• 1997
  • 1997-11-17 DE DE19750800A patent/DE19750800C2/de not_active Expired - Fee Related
• 1998
  • 1998-11-09 DE DE59809229T patent/DE59809229D1/de not_active Expired - Lifetime
  • 1998-11-09 EP EP98955557A patent/EP1032552B1/de not_active Expired - Lifetime
  • 1998-11-09 ES ES98955557T patent/ES2205571T3/es not_active Expired - Lifetime
  • 1998-11-09 WO PCT/EP1998/007148 patent/WO1999025673A1/de not_active Ceased
  • 1998-11-09 JP JP2000521060A patent/JP2001523654A/ja active Pending
• 2001
  • 2001-06-12 US US09/880,695 patent/US7169959B2/en not_active Expired - Lifetime

Patent Citations (2)

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