CA2019831A1 - Method of producing fatty acid amides directly from crude fats and oils - Google Patents
Method of producing fatty acid amides directly from crude fats and oilsInfo
- Publication number
- CA2019831A1 CA2019831A1 CA 2019831 CA2019831A CA2019831A1 CA 2019831 A1 CA2019831 A1 CA 2019831A1 CA 2019831 CA2019831 CA 2019831 CA 2019831 A CA2019831 A CA 2019831A CA 2019831 A1 CA2019831 A1 CA 2019831A1
- Authority
- CA
- Canada
- Prior art keywords
- oil
- oils
- fats
- fatty acids
- crude
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
Abstract
396-16(1)/9/98 June 1990 ABSTRACT
The present invention relates to a method of producing amides of naturally occurring fatty acids from fats and oils by direct reaction of the initial substance with amide-forming reagents.
The present invention relates to a method of producing amides of naturally occurring fatty acids from fats and oils by direct reaction of the initial substance with amide-forming reagents.
Description
Z~8~3~.
The invention relates to a method of producing acid amides of naturally occurring fatty acids by direct reaction of crude fats and oils with amide-forming reagents.
At all times, oils and fats of vegetable and animal origin have been important raw materials both for human nutrition and for the production of key chemicals to be used in the manufacture of textile finishing products, paints, varnishes and similar products, cosmetics, candles, soap, surfactants, lubricants, softening agents, cement and asphalt additives, plastics, as well as the production of free fatty acids. In view of diminishing raw materials reserves, e.g. mineral oil reserves, it can be assumed that naturally occurring fats and oils as renewable raw materials will gain increasing industrial importance in the future.
~ndustrial production of chemical elements from fats and oils is not without problems however. Thus, the crude fats and oils that can be won from oil seeds often contain numerous undesired companion substances such as phosphatides, mucilaginous substances, pigments and odorous substances or hydrocarb~ns. Such companion substances impede direct processing of these crude fats and oils.
For example, they can act as catalysts which, especially in the presence of larger quantities of unsaturated fatty acids, cause decomposition or resinification of the initial substance so that the potential yield is considerably reduced. Therefore the crude fats and oils can only be processed into useful chemical elements after they have been subjected to complicated and costly methods such as desliming, deacidification, decolouration and deodoration to free them from such ingredients. Oleochemistry, which deals with the chemical-technical processing of oils and fats into secondary products, therefore gets its raw materials usually in the form of pre-cleaned triglycerides from the oil and fat producing industry, e.g. from oil mills. In this connection the problem arises, however, that the oil mills are designed for handling large quantities of oil seeds, so that processing oils seeds that are available only in small quantities is hardly possible. Thus, the ~3~
oils from new breeds of oil-producing plants such as the "high-oleic" sunflower breed or Euphorbia lathyris, which, because of their special fatty acid composition, are particularly suitable initial substances for high-percentage oleic acid, are excluded from industrial-scale utilisation because of the uneconomical cleaning process they require. A further drawback of some oil seeds is that in addition to the said companion substances they often have ingredients that are hazardous from the point of view of nutritional physiology, if not toxic, and that this fact alone makes the oils unsuited for processing in facilities that also serve to produce fats for human consumption and would therefore have to be cleaned at an enormous expense of effort and money.
Therefore it is the object of this invention to provide a method by which crude oils and fats can be used directly as initial substances, without complex cleaning procedures, and to render the oils from those kinds of oil seed into useful raw materials whose production involves great difficulties because the oil seeds are only available in small quantities or contain problematic ingredients.
Surprisingly, it was found that the amides of fatty acids can also be recovered at high purity by reacting the crude oils from oil presses with amide-forming reagents.
Even oils that are highly reactive because of the large number of double bonds they contain, e.g. linseed oil, can be reacted without problem by means of this method. Therefore the subject matter of the invention is a method as claimed in Claim 1.
Basically any kind of fat and oil can be used as initial substance for the method according to the invention. In the following, the terms fat and oil are used to denote those products of vegetable or animal origin which consist chiefly of mixed glycerol esters of higher fatty acids, i.e. primarily triglycerides, but which can of course also contain undetermined amounts of monoglycerides, diglycerides or other naturally occurring fatty acid esters. The method is particularly suitable for reacting crude fats and oils such as can be obtained by the usual methods, e.g. cold or hot pressing in worm or screw presses, or by press extraction. Those fats and oils are preferably used which have a particularly high content of functional or extraordinary fatty acids, because the appropriate fatty acid derivatives can be obtained particularyl easily from these substances at high yield and great purity. The content of ordinary functional fatty acids should preferably amount to at least 50 %, that of extraordinary fatty acids to at least 10 %, always related to the total number of fatty acid molecules.
Preferably used oils are the oil of ~uphorbia lathyris, sunflower oil rich in linoleic acid or oleic acid, in particular the i'high-oleic" kind of sunflower oil, hardened and unhardened castor oil, linseed oil, rapeseed oil, especially that which is rich in erucic acid, the oil of Jatropha curcas, olive oil or the oil from marine animals such as ~ish or whale oil. It is advisable that any solid matter that is possibly contained in the initial substances, such as wood or plant residues, be removed prior to the reaction. The initial reaction batch may be varied at will, so that bascially the method can be applied both in the laboratory and at the industrial scale.
The fats and oils are reacted directly with the amide-forming substances. Amide-forming substances include, for example, ammonia, formamide or primary and secondary aliphatic, cyclo-aliphatic, aliphatic-aromatic and aromatic amines, preferably monoamines or diamines wlth 1 - 44 car~on atoms. This also includes dimeric fatty acids from nati~e fats and oils. The amines may bear additional reactive functional groups, e.g., OH groups. In the case of diamines, additional structural elements or functional groups may be arranged between the two amino functions in the hydrocarbon chain or at the cylcoaliphatic or aromatic residue, for example ether groups, amino groups, diamide groupin~s, ~etone groups or sulphone groups. Preferred amino compounds are methylamine, ethylamine, methylethylamine, dimethylamine, diethylamine, morpholine, benzylamine, naphthylamine, phenylethylamine, aniline, toluidine, diethylenetriamine, 1,~-diaminoethane, 1,3-diaminopropane, 1,6-diaminohexane, 1,8-diaminooctane, piperazine, ~,7,10-trioxatridecane-1,13-diamine,3,3'-diaminodiphenylsulphone, 3,3'-dimethyl-4,4'-diaminodicyclo-hexylmethane, ethanolamine, 3-aminopropanol and commercially available ether diamines with the structural formula CH, H2N~CHCH[OCH2~H]nNH2/
CH, where n is an integral number between 1 and 2000.
1,2-diaminoethane and 1,6-diaminohexane are particularly preferable compounds.
The amines are preferably used in stoichometric quantities related to the number of amino functions and fatty acid residues, but a minor excess or deficiency of amino functions does not influence the yield of the reaction substantially.
The reaction can also be performed with an appropriate solvent to assure a homogeneous reaction process. Non-polar solvents are usually employed for this, in particular toluene, ~ylene or petroleum ether.
The reaction can occur at temperatures bet~een 20 and 300C, but the temperature range between 50 and 200C is preferred, because in this temperature range the reaction time is a reasonable 1 to 6 hours.
As a precaution, the reaction is carried out in a closed system, e.g. an autoclave. Although it is possible to work under air, an inert gas atmosphere, e.g. of argon or nitrogen, or of the vapour of an inert solvent, is preferred because undesired side-reactions such as oxidation of the initial substance can thus be suppressed more easily.
If necessary, catalysts such as ammonium chloride or toluene-p-sulphonic acid can be added to the reaction mixture. At appropriate temperatures, biological catalysts such as esterases can also be used. Other auxiliary agents and additives like polymerisation inhibitors and antioxidants, e.g. ascorbic acid or glucose, can also be added.
~ 6~3~
After the reaction, i.e. no later than after the possi~ly present solvent has been removed, the reaction products precipitate. They are separated and then recrystallised from appropriate solvents.
Both non-polar solvents like hexane and extremely polar solvents like sulphoxides are suitable for this. Recrystallisation from methanol or ethanol is preferred. A simple washing process, for example with cold methanol or toluene, is possibly also sufficient for this. However, the reaction mixture can also be subjected to a steam-solvent extraction process, which also yields the acid amides in crystalline form.
When the fatty acids have been withdrawn in form of acid amides, the companion substances of the oils and the glycerin remain in the mother liquor in concentrated form. Some of the oil companions, e.g. the vitamines that are always present, as well as the glycerin are also interesting for industry. Since separation of such concentrated mixtures is much easier, the method permits these substances also to be recovered in a simpler way.
The acid amides produced in this way contain no undesired companion substances and when appropriate crude oils are used, they have a degree of purity that presents no problems in further processing.
Thus, the fatty acid amides - possibly in form of mixtures - can either be used directly as additives, e.g. Eor lubricants, or converted into other interesting secondary products. Particularly interesting secondary products which so far could only be obtained at considerable effort, if at all, are achieved, for example, from difatty acid diamides that are obtained by reacting fats and oils with diamines, in particular those diamides that result from oils and fats in which one fatty acid is predominant that bears a functional group like a carbon-carbon double bond or an OH group.
According to the invention it is possible, for example, to produce highly concentrated dioleic acid diamides from the crude oil of Euphorbia lathyris seeds and highly concentrated dlricinoleic acid diamides from crude castor oil. As described in the simultansously filed Patent Application P [396-16/(3)/9/89], such difatty acid diamides can be reacted with appropriate difunctional compounds like diisocyanates and thus constitute new key chemicals for the production of prepolymers, plastics and plastic additives, e.g., .
~ 8t~
for adhesives, sealing materials, foamed plastics, lubricants and a number of other technical auxiliary substances. With the usual saponification methods it is also possible to produce free fatty acids from the fatty acid amides, which is particularly advantageous with a view to the production of rare fatty acids such as fatty acids with five double bonds. If the fatty acids obtained in this way comprise functional groups, they may themselves also ser~e as basic or additive substances for plastics.
Consequently, the invention not only provides a method of processing crude oils and fats that could not be utilised as raw materials so far, but it also permits a large variety of new key chemicals to be produced, or chemicals that could only be obtalned at great effort and expense so far, and that are of great interest for further processing in the chemical industry.
The invention is exemplified in the following.
~3 Example 1:
Reaction of crude euphorbia oil with 1,2-diaminoethane 100 g euphorbia oil is reacted with 9.4 g 1,2-diaminoethane in an autoclave in nitrogen atmosphere, first 3 hours at 180C and then another 3 hours at 100C. The reaction product is recrystallised twice from methanol. The N,N'-ethylenebisoleodiamide obtained in this way has a purity >90%.
(Melting point~ to 116C; yield: 73 g) Example_2:
Reaction of castor oil with 1,2-diaminoethane 5.1 g castor oil and 0.5 g 1,2-diaminoethane are stirred for 5 hours in an autoclave in nitrogen atmosphere at 120C. The reaction product is recrystallised from methanol. The N,N'-ethylene-bisricinoldiamide obtained in this way has a purity >90%.
(Melting point: 83 to 85C; yield: 2.6 g) Example 3:
Reaction of castor oil with 1,6-diaminohexane 51 g castor oil and 9.7 g 1,6-diaminohexane are stirred for 5 hours in a nitrogen atmosphere at 100C. The reaction product is recrystallised from 150 ml methanol. The hexamethylene-bisricinoleic acid diamide obtained in this way has a purity >90%.
(Melting point: 86 to 88C; yield: 32 g).
The invention relates to a method of producing acid amides of naturally occurring fatty acids by direct reaction of crude fats and oils with amide-forming reagents.
At all times, oils and fats of vegetable and animal origin have been important raw materials both for human nutrition and for the production of key chemicals to be used in the manufacture of textile finishing products, paints, varnishes and similar products, cosmetics, candles, soap, surfactants, lubricants, softening agents, cement and asphalt additives, plastics, as well as the production of free fatty acids. In view of diminishing raw materials reserves, e.g. mineral oil reserves, it can be assumed that naturally occurring fats and oils as renewable raw materials will gain increasing industrial importance in the future.
~ndustrial production of chemical elements from fats and oils is not without problems however. Thus, the crude fats and oils that can be won from oil seeds often contain numerous undesired companion substances such as phosphatides, mucilaginous substances, pigments and odorous substances or hydrocarb~ns. Such companion substances impede direct processing of these crude fats and oils.
For example, they can act as catalysts which, especially in the presence of larger quantities of unsaturated fatty acids, cause decomposition or resinification of the initial substance so that the potential yield is considerably reduced. Therefore the crude fats and oils can only be processed into useful chemical elements after they have been subjected to complicated and costly methods such as desliming, deacidification, decolouration and deodoration to free them from such ingredients. Oleochemistry, which deals with the chemical-technical processing of oils and fats into secondary products, therefore gets its raw materials usually in the form of pre-cleaned triglycerides from the oil and fat producing industry, e.g. from oil mills. In this connection the problem arises, however, that the oil mills are designed for handling large quantities of oil seeds, so that processing oils seeds that are available only in small quantities is hardly possible. Thus, the ~3~
oils from new breeds of oil-producing plants such as the "high-oleic" sunflower breed or Euphorbia lathyris, which, because of their special fatty acid composition, are particularly suitable initial substances for high-percentage oleic acid, are excluded from industrial-scale utilisation because of the uneconomical cleaning process they require. A further drawback of some oil seeds is that in addition to the said companion substances they often have ingredients that are hazardous from the point of view of nutritional physiology, if not toxic, and that this fact alone makes the oils unsuited for processing in facilities that also serve to produce fats for human consumption and would therefore have to be cleaned at an enormous expense of effort and money.
Therefore it is the object of this invention to provide a method by which crude oils and fats can be used directly as initial substances, without complex cleaning procedures, and to render the oils from those kinds of oil seed into useful raw materials whose production involves great difficulties because the oil seeds are only available in small quantities or contain problematic ingredients.
Surprisingly, it was found that the amides of fatty acids can also be recovered at high purity by reacting the crude oils from oil presses with amide-forming reagents.
Even oils that are highly reactive because of the large number of double bonds they contain, e.g. linseed oil, can be reacted without problem by means of this method. Therefore the subject matter of the invention is a method as claimed in Claim 1.
Basically any kind of fat and oil can be used as initial substance for the method according to the invention. In the following, the terms fat and oil are used to denote those products of vegetable or animal origin which consist chiefly of mixed glycerol esters of higher fatty acids, i.e. primarily triglycerides, but which can of course also contain undetermined amounts of monoglycerides, diglycerides or other naturally occurring fatty acid esters. The method is particularly suitable for reacting crude fats and oils such as can be obtained by the usual methods, e.g. cold or hot pressing in worm or screw presses, or by press extraction. Those fats and oils are preferably used which have a particularly high content of functional or extraordinary fatty acids, because the appropriate fatty acid derivatives can be obtained particularyl easily from these substances at high yield and great purity. The content of ordinary functional fatty acids should preferably amount to at least 50 %, that of extraordinary fatty acids to at least 10 %, always related to the total number of fatty acid molecules.
Preferably used oils are the oil of ~uphorbia lathyris, sunflower oil rich in linoleic acid or oleic acid, in particular the i'high-oleic" kind of sunflower oil, hardened and unhardened castor oil, linseed oil, rapeseed oil, especially that which is rich in erucic acid, the oil of Jatropha curcas, olive oil or the oil from marine animals such as ~ish or whale oil. It is advisable that any solid matter that is possibly contained in the initial substances, such as wood or plant residues, be removed prior to the reaction. The initial reaction batch may be varied at will, so that bascially the method can be applied both in the laboratory and at the industrial scale.
The fats and oils are reacted directly with the amide-forming substances. Amide-forming substances include, for example, ammonia, formamide or primary and secondary aliphatic, cyclo-aliphatic, aliphatic-aromatic and aromatic amines, preferably monoamines or diamines wlth 1 - 44 car~on atoms. This also includes dimeric fatty acids from nati~e fats and oils. The amines may bear additional reactive functional groups, e.g., OH groups. In the case of diamines, additional structural elements or functional groups may be arranged between the two amino functions in the hydrocarbon chain or at the cylcoaliphatic or aromatic residue, for example ether groups, amino groups, diamide groupin~s, ~etone groups or sulphone groups. Preferred amino compounds are methylamine, ethylamine, methylethylamine, dimethylamine, diethylamine, morpholine, benzylamine, naphthylamine, phenylethylamine, aniline, toluidine, diethylenetriamine, 1,~-diaminoethane, 1,3-diaminopropane, 1,6-diaminohexane, 1,8-diaminooctane, piperazine, ~,7,10-trioxatridecane-1,13-diamine,3,3'-diaminodiphenylsulphone, 3,3'-dimethyl-4,4'-diaminodicyclo-hexylmethane, ethanolamine, 3-aminopropanol and commercially available ether diamines with the structural formula CH, H2N~CHCH[OCH2~H]nNH2/
CH, where n is an integral number between 1 and 2000.
1,2-diaminoethane and 1,6-diaminohexane are particularly preferable compounds.
The amines are preferably used in stoichometric quantities related to the number of amino functions and fatty acid residues, but a minor excess or deficiency of amino functions does not influence the yield of the reaction substantially.
The reaction can also be performed with an appropriate solvent to assure a homogeneous reaction process. Non-polar solvents are usually employed for this, in particular toluene, ~ylene or petroleum ether.
The reaction can occur at temperatures bet~een 20 and 300C, but the temperature range between 50 and 200C is preferred, because in this temperature range the reaction time is a reasonable 1 to 6 hours.
As a precaution, the reaction is carried out in a closed system, e.g. an autoclave. Although it is possible to work under air, an inert gas atmosphere, e.g. of argon or nitrogen, or of the vapour of an inert solvent, is preferred because undesired side-reactions such as oxidation of the initial substance can thus be suppressed more easily.
If necessary, catalysts such as ammonium chloride or toluene-p-sulphonic acid can be added to the reaction mixture. At appropriate temperatures, biological catalysts such as esterases can also be used. Other auxiliary agents and additives like polymerisation inhibitors and antioxidants, e.g. ascorbic acid or glucose, can also be added.
~ 6~3~
After the reaction, i.e. no later than after the possi~ly present solvent has been removed, the reaction products precipitate. They are separated and then recrystallised from appropriate solvents.
Both non-polar solvents like hexane and extremely polar solvents like sulphoxides are suitable for this. Recrystallisation from methanol or ethanol is preferred. A simple washing process, for example with cold methanol or toluene, is possibly also sufficient for this. However, the reaction mixture can also be subjected to a steam-solvent extraction process, which also yields the acid amides in crystalline form.
When the fatty acids have been withdrawn in form of acid amides, the companion substances of the oils and the glycerin remain in the mother liquor in concentrated form. Some of the oil companions, e.g. the vitamines that are always present, as well as the glycerin are also interesting for industry. Since separation of such concentrated mixtures is much easier, the method permits these substances also to be recovered in a simpler way.
The acid amides produced in this way contain no undesired companion substances and when appropriate crude oils are used, they have a degree of purity that presents no problems in further processing.
Thus, the fatty acid amides - possibly in form of mixtures - can either be used directly as additives, e.g. Eor lubricants, or converted into other interesting secondary products. Particularly interesting secondary products which so far could only be obtained at considerable effort, if at all, are achieved, for example, from difatty acid diamides that are obtained by reacting fats and oils with diamines, in particular those diamides that result from oils and fats in which one fatty acid is predominant that bears a functional group like a carbon-carbon double bond or an OH group.
According to the invention it is possible, for example, to produce highly concentrated dioleic acid diamides from the crude oil of Euphorbia lathyris seeds and highly concentrated dlricinoleic acid diamides from crude castor oil. As described in the simultansously filed Patent Application P [396-16/(3)/9/89], such difatty acid diamides can be reacted with appropriate difunctional compounds like diisocyanates and thus constitute new key chemicals for the production of prepolymers, plastics and plastic additives, e.g., .
~ 8t~
for adhesives, sealing materials, foamed plastics, lubricants and a number of other technical auxiliary substances. With the usual saponification methods it is also possible to produce free fatty acids from the fatty acid amides, which is particularly advantageous with a view to the production of rare fatty acids such as fatty acids with five double bonds. If the fatty acids obtained in this way comprise functional groups, they may themselves also ser~e as basic or additive substances for plastics.
Consequently, the invention not only provides a method of processing crude oils and fats that could not be utilised as raw materials so far, but it also permits a large variety of new key chemicals to be produced, or chemicals that could only be obtalned at great effort and expense so far, and that are of great interest for further processing in the chemical industry.
The invention is exemplified in the following.
~3 Example 1:
Reaction of crude euphorbia oil with 1,2-diaminoethane 100 g euphorbia oil is reacted with 9.4 g 1,2-diaminoethane in an autoclave in nitrogen atmosphere, first 3 hours at 180C and then another 3 hours at 100C. The reaction product is recrystallised twice from methanol. The N,N'-ethylenebisoleodiamide obtained in this way has a purity >90%.
(Melting point~ to 116C; yield: 73 g) Example_2:
Reaction of castor oil with 1,2-diaminoethane 5.1 g castor oil and 0.5 g 1,2-diaminoethane are stirred for 5 hours in an autoclave in nitrogen atmosphere at 120C. The reaction product is recrystallised from methanol. The N,N'-ethylene-bisricinoldiamide obtained in this way has a purity >90%.
(Melting point: 83 to 85C; yield: 2.6 g) Example 3:
Reaction of castor oil with 1,6-diaminohexane 51 g castor oil and 9.7 g 1,6-diaminohexane are stirred for 5 hours in a nitrogen atmosphere at 100C. The reaction product is recrystallised from 150 ml methanol. The hexamethylene-bisricinoleic acid diamide obtained in this way has a purity >90%.
(Melting point: 86 to 88C; yield: 32 g).
2~
Exam~le 4:
Reaction of hardened castor oil with 1,2-diaminoethane 153 g hardened castor oil and 15 g 1,2 diaminoethane are stirred for 5 hours in an autoclave in a nitrogen atmosphere at 140C. The reaction product is recrystallised from methanol. The bis(12-hydroxystearic acid)-N,N'-ethylenediamide obtained in this way has a purity >90%.
(Melting point: 142-145C; yield: 106.5 g).
Example 5:
Reaction of hardened castor oil with 1,6-diaminohexane 5.1 g hardened castor oil and 0.97 1,6-diaminohexane are stirred for 5 hours in an autoclave in nitrogen atmosphere at 150C. The reaction product is subjected to hot vapour extraction with methanol. The bis(1~-hydroxystearic acid)-1,6-N,N'-hexamethylenediamide obtained in this way has a purity >90%.
(Melting point: 135-136C; yield: 3.7 g).
Exam~le 4:
Reaction of hardened castor oil with 1,2-diaminoethane 153 g hardened castor oil and 15 g 1,2 diaminoethane are stirred for 5 hours in an autoclave in a nitrogen atmosphere at 140C. The reaction product is recrystallised from methanol. The bis(12-hydroxystearic acid)-N,N'-ethylenediamide obtained in this way has a purity >90%.
(Melting point: 142-145C; yield: 106.5 g).
Example 5:
Reaction of hardened castor oil with 1,6-diaminohexane 5.1 g hardened castor oil and 0.97 1,6-diaminohexane are stirred for 5 hours in an autoclave in nitrogen atmosphere at 150C. The reaction product is subjected to hot vapour extraction with methanol. The bis(1~-hydroxystearic acid)-1,6-N,N'-hexamethylenediamide obtained in this way has a purity >90%.
(Melting point: 135-136C; yield: 3.7 g).
Claims (13)
1. Method of producing the amides of natural fatty acids from oils and fats, c o m p r i s i n g:
reacting crude fats and oils as initial substances, possibly using an appropriate solvent and possibly with the addition of appropriate catalysts and antioxidants, directly with amide-forming reagents to give the corresponding fatty acid amides, and purifying the latter if necessary.
reacting crude fats and oils as initial substances, possibly using an appropriate solvent and possibly with the addition of appropriate catalysts and antioxidants, directly with amide-forming reagents to give the corresponding fatty acid amides, and purifying the latter if necessary.
2. Method as claimed in Claim 1, w h e r e i n the crude fats and oils have a high content of functional fatty acids.
3. Method as claimed in Claim 1, w h e r e i n the crude fats and oils contain extraordinary fatty acids.
4. Method as claimed in any of Claims 1 to 3, w h e r e i n euphorbia oil, sunflower oil rich in linoleic or oleic acid, especially of the "high-oleic" kind, rapeseed oil, especially rapeseed opil rich in erucic acid, the oil of Jatropha curcas, castor oil or hydrogenated castor oil, linseed oil, olive oil or the oil of marine animals, e.g. fish or whale oil, is used as crude fat or oil.
5. Method as claimed in any of Claims l to 4, w h e r e i n primary and secondary aliphatic, cyclo-aliphatic or aliphatic-aromatic monoamines or diamines are used as amide-forming reagents.
6. Method as claimed in any of Claims 1 to 5, w h e r e i n 1,2-diaminoethane or 1,6-diaminohexane is used as amide-forming reagent.
7. Method as claimed in any of Claims 1 to 6, w h e r e i n toluene, xylene or petroleum ether is used as solvent.
8. Method as claimed in any of Claims 1 to 7, w h e r e i n the initial substance is reacted with the amides at 20-300 °C, preferably at 50-200 °C.
9. Method as claimed in any of Claims 1 to 8, w h e r e i n the work is carried out in a inert gas atmosphere of nitrogen or argon.
10. Method as claimed in any of Claims 1 to 9, w h e r e i n ammonium chloride or toluene-p-sulphonic acid is used as catalyst.
11. Method as claimed in any of Claims 1 to 10, w h e r e i n ascorbic acid or glucose is used as antioxidant.
12. Method as claimed in any one of Claims 1 to 11, w h e r e i n the fatty acid amides are cleaned by recrystallisation from methanol or ethanol.
13. Method as claimed in any of Claims 1 to 11, w h e r e i n the fatty acid amides are cleaned by hot solvent vapour extraction.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3921343 | 1989-06-29 | ||
| DEP3921343.9 | 1989-06-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2019831A1 true CA2019831A1 (en) | 1990-12-29 |
Family
ID=6383888
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2019831 Abandoned CA2019831A1 (en) | 1989-06-29 | 1990-06-26 | Method of producing fatty acid amides directly from crude fats and oils |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0432248A1 (en) |
| JP (1) | JPH04500686A (en) |
| CA (1) | CA2019831A1 (en) |
| WO (1) | WO1991000264A1 (en) |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB558854A (en) * | 1941-06-17 | 1944-01-25 | Nat Oil Prod Co | Improvements in or relating to hard wax substitutes |
| GB632242A (en) * | 1946-05-31 | 1949-11-18 | Ici Ltd | Improvements in or relating to the manufacture of ricinoleyl amines and to the treatment of water to prevent foaming |
| GB1084981A (en) * | 1963-09-13 | 1967-09-27 | Louis Herbert Libby | Improvements in or relating to n-ethyl carboxylic acid amide derivatives |
| GB1250421A (en) * | 1968-02-05 | 1971-10-20 |
-
1990
- 1990-06-22 WO PCT/EP1990/000997 patent/WO1991000264A1/en not_active Application Discontinuation
- 1990-06-22 JP JP50918590A patent/JPH04500686A/en active Pending
- 1990-06-22 EP EP19900909729 patent/EP0432248A1/en not_active Ceased
- 1990-06-26 CA CA 2019831 patent/CA2019831A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| WO1991000264A1 (en) | 1991-01-10 |
| EP0432248A1 (en) | 1991-06-19 |
| JPH04500686A (en) | 1992-02-06 |
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