CA2174723C - Process for the production of fatty alcohols based on vegetable fats and oils by fractionation - Google Patents
Process for the production of fatty alcohols based on vegetable fats and oils by fractionation Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/2003—Alcohols; Phenols
- C11D3/2006—Monohydric alcohols
- C11D3/2027—Monohydric alcohols unsaturated
- C11D3/2031—Monohydric alcohols unsaturated fatty or with at least 8 carbon atoms in the alkenyl chain
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
- A61K8/342—Alcohols having more than seven atoms in an unbroken chain
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
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- 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
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/02—Monohydroxylic acyclic alcohols
- C07C31/125—Monohydroxylic acyclic alcohols containing five to twenty-two carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/02—Acyclic alcohols with carbon-to-carbon double bonds
- C07C33/025—Acyclic alcohols with carbon-to-carbon double bonds with only one double bond
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/2003—Alcohols; Phenols
- C11D3/2006—Monohydric alcohols
- C11D3/201—Monohydric alcohols linear
- C11D3/2013—Monohydric alcohols linear fatty or with at least 8 carbon atoms in the alkyl chain
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/2003—Alcohols; Phenols
- C11D3/2006—Monohydric alcohols
- C11D3/2017—Monohydric alcohols branched
- C11D3/202—Monohydric alcohols branched fatty or with at least 8 carbon atoms in the alkyl chain
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Abstract
The invention concerns a method of producing fatty alcohols with an iodine number between 20 and 110 from vegetable oils, the alcohols consisting essentially of unsaturated fatty alcohols or mixtures of saturated and unsaturated fatty alcohols of the general formula (I): R1OH, in which R1 is a saturated or unsaturated straight-chain or branched-chain alkyl group with 8 to 22 carbon atoms. Using prior art methods, the triglycerides contained in the vegetable-oil raw materials are (a) decomposed under pressure into the constituent fatty acids and optionally esterified with methanol or (b) transesterified to give the fatty-acid methyl esters and (c) the fatty acids or fatty-acid methyl esters are hydrogenated to give fatty alcohols. The method is characterized in that the fatty acids, the fatty-acid methyl esters and/or their hydrogenation products are fractionally distilled and the first runnings taken from the distillation, the end product having an iodine number from 20 to 110. The invention also concerns fatty alcohols produced from vegetable oils having an iodine number from 20 to 95 and the use of fatty alcohols produced from vegetable oils in the manufacture of washing, rinsing and cleaning agents as well as hair-care and body-care agents.
Description
A process for the production of fatty alcohols based on vegetable fats and oils by fractionation ~3ackground of the Invention This invention relates to a process for. the produc-tion of fatty alcohols based on vegetable fats and oils with an iodine value in the range from 20 to 110, to fatty alcohols based on vegetable fats and oils with an iodine value of 20 to less than 95 and to the use of these products for the production surface-active formula-tions.
Statement of Related Art Fatty compounds, particularly unsaturated fatty alcohols, are important intermediates for a large number of products of the chemical industry, for example for the production of surfactants and skin-care products. An overview of these intermediate products is provided, for example, by U. Ploog et al. in Seifen-ole Fette-Wachse 109, 225 (1983). They are produced fram more or less unsaturated fatty acid methyl esters which may be hydro-genated, for example, in the presence of chromium- or zinc-containing mixed catalysts [Ullmann~s Enzyclopaedie der technischen Chemie, Verlag Chemie, Weinheim, 4th Edition, Vol. 11, pages 436 et seq.].
The prior art in this field is an industrial process using animal fats and oils which has also been carried out by applicants and in which the unsaturated fatty alcohols accumulating after hydrogenation are distilled at a bottom temperature of, for example, X120 to 2.50 ° C and under a reduced pressure of 1 to 20 mbar, as measured at
Statement of Related Art Fatty compounds, particularly unsaturated fatty alcohols, are important intermediates for a large number of products of the chemical industry, for example for the production of surfactants and skin-care products. An overview of these intermediate products is provided, for example, by U. Ploog et al. in Seifen-ole Fette-Wachse 109, 225 (1983). They are produced fram more or less unsaturated fatty acid methyl esters which may be hydro-genated, for example, in the presence of chromium- or zinc-containing mixed catalysts [Ullmann~s Enzyclopaedie der technischen Chemie, Verlag Chemie, Weinheim, 4th Edition, Vol. 11, pages 436 et seq.].
The prior art in this field is an industrial process using animal fats and oils which has also been carried out by applicants and in which the unsaturated fatty alcohols accumulating after hydrogenation are distilled at a bottom temperature of, for example, X120 to 2.50 ° C and under a reduced pressure of 1 to 20 mbar, as measured at
2 PCT/EP94/03348 the head of the column. Since the production of unsat-urated fatty alcohols involves high costs, the distilla-tion conditions were designed to minimize the loss of raw materials. In fact, a yield of around 90% of the theore-tical (and hence a loss of 10~) was achieved in this way.
Unfortunately, the products had a distinct odor. Another disadvantage was that the fatty alcohols of the prior art show unsatisfactory storage and low-temperature behavior.
Unsaturated fatty alcohols with iodine values of 20 to 95 are particularly preferred for' applicational reasons because they have a particularly favorable solidification point for use in cosmetic products.
Hitherto, unsaturated fatty alcohols with iodine values in the range mentioned have always been based on animal fats. The desired iodine value range is established by blending various products with different iodine value ranges. The iodine value range cannot be established by distillation-based processes because the iodine value or rather the iodine value range of fatty alcohols or fatty acids based on animal fats remains substantially constant during fractionation.
However, animal fats have the disadvantage that they are extremely heterogeneous. For example, animal fats contain nitrogen-containing compounds, such as amides or steroids, such as cholesterol for example, which are directly or indirectly responsible for the unpleasant odor of the products mentioned above. The nitrogen-containing compounds can enter into secondary reactions which adversely affects product stability, particularly oxidation stability, and leads to discolared products.
There is an urgent need in the cosmetic market in particular for purer raw materials of higher quality - a requirement which normally can only be satisfied by increasingly more expensive technical processes and additional purification steps. In the case of unsatura-' CA 02174723 2005-08-25
Unfortunately, the products had a distinct odor. Another disadvantage was that the fatty alcohols of the prior art show unsatisfactory storage and low-temperature behavior.
Unsaturated fatty alcohols with iodine values of 20 to 95 are particularly preferred for' applicational reasons because they have a particularly favorable solidification point for use in cosmetic products.
Hitherto, unsaturated fatty alcohols with iodine values in the range mentioned have always been based on animal fats. The desired iodine value range is established by blending various products with different iodine value ranges. The iodine value range cannot be established by distillation-based processes because the iodine value or rather the iodine value range of fatty alcohols or fatty acids based on animal fats remains substantially constant during fractionation.
However, animal fats have the disadvantage that they are extremely heterogeneous. For example, animal fats contain nitrogen-containing compounds, such as amides or steroids, such as cholesterol for example, which are directly or indirectly responsible for the unpleasant odor of the products mentioned above. The nitrogen-containing compounds can enter into secondary reactions which adversely affects product stability, particularly oxidation stability, and leads to discolared products.
There is an urgent need in the cosmetic market in particular for purer raw materials of higher quality - a requirement which normally can only be satisfied by increasingly more expensive technical processes and additional purification steps. In the case of unsatura-' CA 02174723 2005-08-25
3 ted fatty alcohols, there is a need above all for prod-ucts with improved color and odor quality and more favorable low-temperature behavior. Added to this is the fact that, in recent years, consumer behavior has changed to the extent that consumers now attribute considerable importance to purely vegetable products.
Known vegetable fatty alcohols have iodine values below 20 or very high iodine values above 100. Fatty alcohols with iodine values in the applicationally l0 preferred range of 20 to 95 mentioned above are not known. The blending of fatty alcohols with very dif-ferent iodine values does not lead to satisfactory products.
The problem addressed by the present invention was to provide fatty alcohols based on vegetable fats and oils which would have iodine values in the applicational ly preferred range and which, at the same time, would have greater oxidation stability than unsaturated fatty alcohols based on animal fats and equivalent or better low-temperature behavior.
Description of the Invention The present invention relates to a process for the production of a fatty alcohol, based on vegetable fats and oils, of the general formula (I):
R10H (I) where R1 is a saturated or unsaturated, linear or branched group, which is a constituent group of the vegetable fats and oils, having from 8 to 22 carbon atoms comprising the steps of: hydrogenating a fatty acid, a fatty acid methyl ester or a combination thereof to form a fatty alcohol; and removing a head fraction from said fatty acid, said fatty acid methyl ester and said fatty alcohol in such a quantity that said fatty alcohol has an iodine value of from 20 to 110 and less than about 4.5% by weight of conjugated compounds.
Known vegetable fatty alcohols have iodine values below 20 or very high iodine values above 100. Fatty alcohols with iodine values in the applicationally l0 preferred range of 20 to 95 mentioned above are not known. The blending of fatty alcohols with very dif-ferent iodine values does not lead to satisfactory products.
The problem addressed by the present invention was to provide fatty alcohols based on vegetable fats and oils which would have iodine values in the applicational ly preferred range and which, at the same time, would have greater oxidation stability than unsaturated fatty alcohols based on animal fats and equivalent or better low-temperature behavior.
Description of the Invention The present invention relates to a process for the production of a fatty alcohol, based on vegetable fats and oils, of the general formula (I):
R10H (I) where R1 is a saturated or unsaturated, linear or branched group, which is a constituent group of the vegetable fats and oils, having from 8 to 22 carbon atoms comprising the steps of: hydrogenating a fatty acid, a fatty acid methyl ester or a combination thereof to form a fatty alcohol; and removing a head fraction from said fatty acid, said fatty acid methyl ester and said fatty alcohol in such a quantity that said fatty alcohol has an iodine value of from 20 to 110 and less than about 4.5% by weight of conjugated compounds.
4 Surprisingly, it has been found that, in contrast to products based on animal fats, it is possible to produce fatty alcohols based on vegetable fats and oils with iodine values in the range mentioned above which contain substantially unsaturated fatty alcohols and mixtures of saturated and unsaturated fatty alcohols corresponding to general formula (I), the iodine value being adjustable to the desired range by simple fractionation in accordance with applicational requirements. The products based on vegetable fats and oils obtained by the process according to the invention show better oxidation stability and less odor than corresponding products based on animal fats.
The present invention also relates to fatty alcohols of the general formula I
R10H ( I ) wherein R' is a saturated or unsaturated, linear or branched group which is a constituent group of vegetable fats and oils, having from 8 to 22 carbon atoms produced by a process comprising the steps of . hydrogenating a fatty acid, a fatty acid methyl ester or a combination thereof to form a fatty alcohol; and removing a head fraction from said fatty acid, said fatty acid methyl ester and said fatty alcohol in such a quantity that said fatty alcohol has an iodine value of from 20 to 110 and less than 4.5°s by weight of conjugated compounds.
i i ., i ~~ ii a i."v"i"i, In addition, compounds corresponding to formula (I), in which R1 is a group containing l2 to 20 carbon atoms, are preferred. Preferably, the iodine value is between 40 and 85.
The fatty alcohols according to the invention show
The present invention also relates to fatty alcohols of the general formula I
R10H ( I ) wherein R' is a saturated or unsaturated, linear or branched group which is a constituent group of vegetable fats and oils, having from 8 to 22 carbon atoms produced by a process comprising the steps of . hydrogenating a fatty acid, a fatty acid methyl ester or a combination thereof to form a fatty alcohol; and removing a head fraction from said fatty acid, said fatty acid methyl ester and said fatty alcohol in such a quantity that said fatty alcohol has an iodine value of from 20 to 110 and less than 4.5°s by weight of conjugated compounds.
i i ., i ~~ ii a i."v"i"i, In addition, compounds corresponding to formula (I), in which R1 is a group containing l2 to 20 carbon atoms, are preferred. Preferably, the iodine value is between 40 and 85.
The fatty alcohols according to the invention show
5 particularly high stability when only a low percentage of conjugated compounds is present. The fatty alcohols according to the invention based on vegetable fats and oils preferably have a content of conjugated compounds below 6% by weight and, more preferably, below 4.5% by weight.
Unsaturated or partLly unsaturated vegetable fats and oils are used as starting materials for the process according to the invention. Palm oil, palm stearin oil, palm kernel olefin oil, coconut oil, palm kernel oil, sunflower oil, new rapeseed oil, soybean oil, peanut oil, rapeseed oil, linseed oil and olive oil are particularly .preferred. The fats consisting essentially of triglycer ides are converted into the fatty acids in known manner by pressure hydrolysis and optionally esterified with methanol or are transesterified with methanol to the fatty acid methyl ester. The fatty acid or the fatty acid methyl ester is then hydrogenated to the correspond-ing fatty alcohol by known methods. The percentage content of saturated and unsaturated constituents and the chain length distribution are determined by the vegetable oils used. In the above compounds corresponding to formula (I), R1 is a group containing 8 to 22 - ~ carbon atoms and preferably 12 to 2r0 carbon atoms.
Through the use of vegetable fats and oils as starting products, the fatty acids/fatty acid methyl esters used or the hydrogenation product are mixtures of fatty acids, fatty acid methyl esters or fatty alcohols differing in their chain lengths. According to the invention, the iodine value of the fatty alcohols to be produced is adjusted by fractionating the fatty acids c
Unsaturated or partLly unsaturated vegetable fats and oils are used as starting materials for the process according to the invention. Palm oil, palm stearin oil, palm kernel olefin oil, coconut oil, palm kernel oil, sunflower oil, new rapeseed oil, soybean oil, peanut oil, rapeseed oil, linseed oil and olive oil are particularly .preferred. The fats consisting essentially of triglycer ides are converted into the fatty acids in known manner by pressure hydrolysis and optionally esterified with methanol or are transesterified with methanol to the fatty acid methyl ester. The fatty acid or the fatty acid methyl ester is then hydrogenated to the correspond-ing fatty alcohol by known methods. The percentage content of saturated and unsaturated constituents and the chain length distribution are determined by the vegetable oils used. In the above compounds corresponding to formula (I), R1 is a group containing 8 to 22 - ~ carbon atoms and preferably 12 to 2r0 carbon atoms.
Through the use of vegetable fats and oils as starting products, the fatty acids/fatty acid methyl esters used or the hydrogenation product are mixtures of fatty acids, fatty acid methyl esters or fatty alcohols differing in their chain lengths. According to the invention, the iodine value of the fatty alcohols to be produced is adjusted by fractionating the fatty acids c
6 PCT/EP94/03348 obtained by pressure hydrolysis, the fatty acid methyl esters obtained by transesterification of the triglycer-ides or the hydrogenation product obtained by hydrogena-tion of the fatty acid or the fatty acid methyl ester.
The iodine value of the product to be fractionated is determined before fractionation. Depending on the starting product or its iodine value and the desired iodine value, a certain quantity of head fraction is removed during fractionation. 8y removing the head fraction, the iodine value of the fatty alcohol is increased. To adjust the iodine value of the product, the iodine value of the product which has not yet dis-tilled over is monitored during fractionation. For example, it is possible by the process according to the invention to obtain from coconut oil/palm kernel oil a fatty acid or fatty acid methyl ester fraction which contains fatty acid or fatty acid methyl ester with chain lengths of 16 to 18 carbon atoms, so-ca:Lled Clsila fatty acid or fatty acid methyl ester, as its principal consti-tuent. The required chain length distribution can also be adjusted by corresponding fractionation of the fatty alcohol.
The fractionation conditions under reduced pressure for the unsaturated fatty alcohols obtained, for example, from the hydrogenation stage have long been known.
Fractionation may be carried out in batches~or continu-ously under reduced pressure. Superheated steam, for example, may be used for heating, the bottom temperature being in the range from 220 to 250°C for example.
:30 The actual fractionation process takes place in a packed column with fittings characterized by a low pressure loss. Suitable fittings are, for example, ordered metal packs. Further examples can be found in ROMPP Chemie Lexikon, Thieme Verlag, Stuttgart, 9th Edition, Vol. 3, page 2305 (1990) under the keyword ~1747~~
The iodine value of the product to be fractionated is determined before fractionation. Depending on the starting product or its iodine value and the desired iodine value, a certain quantity of head fraction is removed during fractionation. 8y removing the head fraction, the iodine value of the fatty alcohol is increased. To adjust the iodine value of the product, the iodine value of the product which has not yet dis-tilled over is monitored during fractionation. For example, it is possible by the process according to the invention to obtain from coconut oil/palm kernel oil a fatty acid or fatty acid methyl ester fraction which contains fatty acid or fatty acid methyl ester with chain lengths of 16 to 18 carbon atoms, so-ca:Lled Clsila fatty acid or fatty acid methyl ester, as its principal consti-tuent. The required chain length distribution can also be adjusted by corresponding fractionation of the fatty alcohol.
The fractionation conditions under reduced pressure for the unsaturated fatty alcohols obtained, for example, from the hydrogenation stage have long been known.
Fractionation may be carried out in batches~or continu-ously under reduced pressure. Superheated steam, for example, may be used for heating, the bottom temperature being in the range from 220 to 250°C for example.
:30 The actual fractionation process takes place in a packed column with fittings characterized by a low pressure loss. Suitable fittings are, for example, ordered metal packs. Further examples can be found in ROMPP Chemie Lexikon, Thieme Verlag, Stuttgart, 9th Edition, Vol. 3, page 2305 (1990) under the keyword ~1747~~
7 PCT/EP94/03348 "column fittings" and in the literature cited therein.
The necessary fine vacuum of 1 to 20 mbar at the head of the column can be obtained, fox example, with water ring pumps and preceding steam jet pumps. The pressure drop throughout the distillation plant should preferably be no more than 20 mbar.
An improvement in the end product can be obtained by distilling the unsaturated fatty alcohols in such a way that a residue of up to 10% by weight and preferably from 2 to 7% by weight is obtained. The color value and odor of the end products are distinctly further improved by this measure.
Industrial Applications :L 5 The unsaturated fatty alcohols based on vegetable fats and oils obtainable by the process according to the invention are substantially colorless and odorless and show particularly favorable low-temperature behavior.
Accordingly, they are suitable as raw materials for the production of laundry detergents, dishwashing detergents and cleaning products and also hair-care and body-care products, in which they may be present in quantities of 1 to 50% by weight and preferably 5 to 30% by weight, based on the particular product.
The invention is illustrated by the following Examples:
Exaa~p 1 a s :30 Fatty acid methyl esters were hydrogenated in a typical hydrogenation reactor under a pressure of around 225 bar and at a temperature of 275 to 33U°C in the pres-ence of a CuCr04 catalyst. The hydrogenation product is distilled, a corresponding head fraction being removed.
The necessary fine vacuum of 1 to 20 mbar at the head of the column can be obtained, fox example, with water ring pumps and preceding steam jet pumps. The pressure drop throughout the distillation plant should preferably be no more than 20 mbar.
An improvement in the end product can be obtained by distilling the unsaturated fatty alcohols in such a way that a residue of up to 10% by weight and preferably from 2 to 7% by weight is obtained. The color value and odor of the end products are distinctly further improved by this measure.
Industrial Applications :L 5 The unsaturated fatty alcohols based on vegetable fats and oils obtainable by the process according to the invention are substantially colorless and odorless and show particularly favorable low-temperature behavior.
Accordingly, they are suitable as raw materials for the production of laundry detergents, dishwashing detergents and cleaning products and also hair-care and body-care products, in which they may be present in quantities of 1 to 50% by weight and preferably 5 to 30% by weight, based on the particular product.
The invention is illustrated by the following Examples:
Exaa~p 1 a s :30 Fatty acid methyl esters were hydrogenated in a typical hydrogenation reactor under a pressure of around 225 bar and at a temperature of 275 to 33U°C in the pres-ence of a CuCr04 catalyst. The hydrogenation product is distilled, a corresponding head fraction being removed.
8 PCT/EP94/03348 Example 1 A Cl2ila palm kernel oil methyl ester obtained from the transesterification of palm kernel oil and subsequent fractionation was fractionated to a Clziia and Clsila methyl ester. The Clsiia methyl ester was hydrogenated to the fatty alcohol as described above. The crude product was distilled in a two-stage vacuum fractionating unit, a head fraction of 3% by weight being removed and a residue of 3% by weight remaining.
A fatty alcohol (FA) with the following chain distribution and the following characteristic data was obtained:
FA C 12 0.2% by weight FA C 14 4.5% by weight FA C 15 0.3% by weight FA C 16 25.1% by weight FA C 16' 0.4% by weight FA C 17 0.3% by weight FA C 18 8.9% by weight FA C 18' 52.5% by weight FA C 18 " 2.9% by weight FA C 18 " conj. 3.2% by weight FA C 18 " ' 0.1% by weight FA C 20 0.6% by weight Acid value - 0.02 Saponification value - 0.35 OH value - 213.5 Iodine value - 61.3 HZO content - 0.02 Softening point - 26.6C
Hydrocarbon content - 0.87% by weight CO value - 360 Hazen - < 10
A fatty alcohol (FA) with the following chain distribution and the following characteristic data was obtained:
FA C 12 0.2% by weight FA C 14 4.5% by weight FA C 15 0.3% by weight FA C 16 25.1% by weight FA C 16' 0.4% by weight FA C 17 0.3% by weight FA C 18 8.9% by weight FA C 18' 52.5% by weight FA C 18 " 2.9% by weight FA C 18 " conj. 3.2% by weight FA C 18 " ' 0.1% by weight FA C 20 0.6% by weight Acid value - 0.02 Saponification value - 0.35 OH value - 213.5 Iodine value - 61.3 HZO content - 0.02 Softening point - 26.6C
Hydrocarbon content - 0.87% by weight CO value - 360 Hazen - < 10
9 PCT/EP94/03348 Example 2 The product obtained from the hydrogenation in Example 1 is distilled in such a way that a head fraction of around 18% by weight is removed, a fatty alcohol with a relatively high iodine value of 75 being obtained.
This fatty alcohol has the following chain distribu-tion and the following characteristic data:
FA C 12 0.0% byweight FA C 14 0.1% byweight FA C 15 0.1% byweight FA C 16 12.1% byweight FA C 16' 0.2% byweight FA C 17 0.3% byweight FA C 18 11.5% byweight FA C 18' 66.5% byweight FA C 18 " 3.7% byweight FA C 18 " conj. 4.3% byweight FA C 18 " ' 0.2% byweight FA C 20 0.4% byweight Acid value - 0.02 Saponification value - 0.40 OH value - 210. 5 Iodine value - 75 HZO content - 0.02 Softening point - 23.2 C
Hydrocarbon content - 0.13 %
by weight CO value - 306 Hazen - 5 Example 3 Starting out from a mixture of a Clsiis Palm kernel oil methyl ester (70% by weight) and rapeseed oil methyl ester (30% by weight) prepared from new rapeseed oil, a 2~ 74 723
This fatty alcohol has the following chain distribu-tion and the following characteristic data:
FA C 12 0.0% byweight FA C 14 0.1% byweight FA C 15 0.1% byweight FA C 16 12.1% byweight FA C 16' 0.2% byweight FA C 17 0.3% byweight FA C 18 11.5% byweight FA C 18' 66.5% byweight FA C 18 " 3.7% byweight FA C 18 " conj. 4.3% byweight FA C 18 " ' 0.2% byweight FA C 20 0.4% byweight Acid value - 0.02 Saponification value - 0.40 OH value - 210. 5 Iodine value - 75 HZO content - 0.02 Softening point - 23.2 C
Hydrocarbon content - 0.13 %
by weight CO value - 306 Hazen - 5 Example 3 Starting out from a mixture of a Clsiis Palm kernel oil methyl ester (70% by weight) and rapeseed oil methyl ester (30% by weight) prepared from new rapeseed oil, a 2~ 74 723
10 PCT/EP94/03348 fatty alcohol with the following chain distribution and the following characteristic data was prepared as de-scribed in Example 1:
FA C 12 0.0% by weight FA C 14 0.0% by weight FA C 15 0.2% by weight FA C 16 23.1% by weight FA C 16' 0.8% by weight FA C 17 0.4% by weight FA C 18 6.4% by weight FA C 18' 60.3% by weight FA C 18 " 4.6% by weight FA C 18 " conj. 3.2% by weight FA C 18 " ' 0.1% by weight FA C 20 0,6% by weight Acid value - 0.02 Saponification value - 0.35 OH value - 213 Iodine value - 73.9 HZO content - 0.03 Softening point - 22.9C
Hydrocarbon content - 0.2% by weight CO value - 279 Hazen - < 10
FA C 12 0.0% by weight FA C 14 0.0% by weight FA C 15 0.2% by weight FA C 16 23.1% by weight FA C 16' 0.8% by weight FA C 17 0.4% by weight FA C 18 6.4% by weight FA C 18' 60.3% by weight FA C 18 " 4.6% by weight FA C 18 " conj. 3.2% by weight FA C 18 " ' 0.1% by weight FA C 20 0,6% by weight Acid value - 0.02 Saponification value - 0.35 OH value - 213 Iodine value - 73.9 HZO content - 0.03 Softening point - 22.9C
Hydrocarbon content - 0.2% by weight CO value - 279 Hazen - < 10
Claims (7)
1. A process for the production of a fatty alcohol, based on vegetable fats and oils, of the general formula (I):
R1OH (I) where R1 is a saturated or unsaturated, linear or branched group, which is a constituent group of the vegetable fats and oils, having from 8 to 22 carbon atoms comprising the steps of: hydrogenating a fatty acid, a fatty acid methyl ester or a combination thereof to form a fatty alcohol; and removing a head fraction from said fatty acid, said fatty acid methyl ester and said fatty alcohol in such a quantity that said fatty alcohol has an iodine value of from 20 to 110 and less than about 4.5% by weight of conjugated compounds.
R1OH (I) where R1 is a saturated or unsaturated, linear or branched group, which is a constituent group of the vegetable fats and oils, having from 8 to 22 carbon atoms comprising the steps of: hydrogenating a fatty acid, a fatty acid methyl ester or a combination thereof to form a fatty alcohol; and removing a head fraction from said fatty acid, said fatty acid methyl ester and said fatty alcohol in such a quantity that said fatty alcohol has an iodine value of from 20 to 110 and less than about 4.5% by weight of conjugated compounds.
2. The process according to claim 1, wherein the iodine value is from 40 to 85.
3. The process according to claim 1, wherein R1 contains from 12 to 20 carbon atoms.
4. A fatty alcohol of the general formula I
R1OH (I) wherein R1 is a saturated or unsaturated, linear or branched group which is a constituent group of vegetable fats and oils, having from 8 to 22 carbon atoms produced by a process comprising the steps of; hydrogenating a fatty acid, a fatty acid methyl ester or a combination thereof to form a fatty alcohol; and removing a head fraction from said fatty acid, said fatty acid methyl ester and said fatty alcohol in such a quantity that said fatty alcohol has an iodine value of from 20 to 110 and less than 4.5% by weight of conjugated compounds.
R1OH (I) wherein R1 is a saturated or unsaturated, linear or branched group which is a constituent group of vegetable fats and oils, having from 8 to 22 carbon atoms produced by a process comprising the steps of; hydrogenating a fatty acid, a fatty acid methyl ester or a combination thereof to form a fatty alcohol; and removing a head fraction from said fatty acid, said fatty acid methyl ester and said fatty alcohol in such a quantity that said fatty alcohol has an iodine value of from 20 to 110 and less than 4.5% by weight of conjugated compounds.
5. The fatty alcohol according to claim 4, wherein the iodine value is from 40 to 85.
6. The fatty alcohol according to claim 4, wherein R1 contains from 12 to 20 carbon atoms.
7. The use of the fatty alcohol according to claim 4, 5, or 6, for the production of a laundry detergent, a dishwashing detergent, a cleaning product, a hair-care product or a body-care product.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4335781A DE4335781C2 (en) | 1993-10-20 | 1993-10-20 | Vegetable-based fatty alcohols and process for their preparation |
| DEP4335781.4 | 1993-10-20 | ||
| PCT/EP1994/003348 WO1995011210A1 (en) | 1993-10-20 | 1994-10-12 | Method of producing fatty alcohols from vegetable oils by fractional distillation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2174723A1 CA2174723A1 (en) | 1995-04-27 |
| CA2174723C true CA2174723C (en) | 2006-10-03 |
Family
ID=37101732
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002174723A Expired - Lifetime CA2174723C (en) | 1993-10-20 | 1994-10-12 | Process for the production of fatty alcohols based on vegetable fats and oils by fractionation |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2174723C (en) |
-
1994
- 1994-10-12 CA CA002174723A patent/CA2174723C/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CA2174723A1 (en) | 1995-04-27 |
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