WO1990015127A1 - Artificial jojoba oil - Google Patents
Artificial jojoba oil Download PDFInfo
- Publication number
- WO1990015127A1 WO1990015127A1 PCT/AU1990/000253 AU9000253W WO9015127A1 WO 1990015127 A1 WO1990015127 A1 WO 1990015127A1 AU 9000253 W AU9000253 W AU 9000253W WO 9015127 A1 WO9015127 A1 WO 9015127A1
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- WO
- WIPO (PCT)
- Prior art keywords
- compound
- acid
- properties
- jojoba oil
- alcohol
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/003—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with alcohols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
- C11C3/10—Ester interchange
Definitions
- This invention relates generally to an artificially synthesized compound, the properties of which are analogous to certain of the properties of naturally occurring jojoba oil, and to a method of producing the artificially synthesized compound.
- WICKENOL 139 is an ester formed from unsaturated straight chain acids, predominantly C__-containing acids and branched chain alcohols, predominantly C -containing acids and thus, has the empirical formula C ⁇ H_ Q 0_.
- WICKENOL 139 is characterized by the infra-red spectrograph as shown in figure 3. Scher Chemicals Inc describe the production of an oil (known as SCHEROBA OIL) in GB 2106507 which the applicants believe to be an ester comprising predominantly isostearylerucyl enucate.
- GB 2106507 discloses the use of alcohols with odd numbers of carbon atoms.
- SCHEROBA OIL is characterized by the infra-red spectrograph as shown in figure 4.
- the aforementioned artifical oils are not entirely satisfactory.
- the lubricity does not equal that of the naturally occurring jojoba oil.
- Jojoba oil both naturally occurring and artificially derived has many known commercial uses, which include such uses as high temperature lubricants, additives to mineral oil to improve their lubricity, additives and/or bases for cosmetic and skin care products such as moisturises, use in electronic components, slip agents in plastic films, leather softening agents, anti-foam agents in preparations of penicillin and tetracyclin, non-corrosive permanent lubricants for scientific instruments and robotics and the like.
- Naturally occurring jojoba oil is composed of esters of monounsaturated straight-chain alcohols and acids. Following intensive research, the present inventors have found a method for preparing a compound, the properties of which in many respects are analogous to the corresponding properties of a naturally occurring jojoba oil.
- One preferred method involves the use of mustard seeds having a high erucic acid content, from which mustard seed oil is extracted and transesterified.
- Mustard seed crops are readily grown in Australia and elsewhere in the world and yield good quantities of mustard seed oil (typically one tonne per hectare) .
- the oil yield from mustard seed which is available for processing is in the order of 35% by weight.
- the present invention provides a method of producing an artificially synthesized compound, the properties of which in many respects are analogous to corresponding properties of naturally occurring jojoba oil, the method comprising subjecting material containing a precursor of the said compound to a transesterification reaction and yielding the said compound.
- the precursor is erucic acid, an erucic acid containing material, or a mixture thereof.
- the alcohol is a branched-chain alcohol, more preferably, 2-octyldodecanol (C n ) . which is marketed by Henckel Chemicals under the trade name Eutanol G, stearyl alcohol (C- 8 ) , cetyl alcohol ( ⁇ _ ⁇ ) ' 1-eicosanol ( 2Q ) , 2-eicosanol (C 2Q ) , oleyl alcohol, isomers thereof, or a mixture of one or more thereof.
- the material containing the percursor comprises material obtained from vegetable oils containing at least 2-66% erucic acid residues, mustard (Brassica) species, rape (high-erucic) species, Crambe abyssinica, or naturally occurring jojoba.
- the erucic acid is combined with other acids. More typically the acid reactant of the transesterification reaction is a combination or collection of all of the acids present in the parent mustard seed oil or mustard oil.
- any suitable alcohol, acid or catalyst may be used in the practice of the present invention.
- sources other than mustard seed may be used to obtain artificially derived jojoba oil and such sources include seed of rapeseed varieties whose oil is high in erucic acid content.
- Preferred additional acids include oleic acid (C18:l), eicosenoic acid (C20:l), erucic acid (C22:l), nervonic acid (C24:l), linoleic acid (C18:2), or a mixture of one or more thereof.
- the transesterification reaction mixture is heated for up to six hours at a temperature of up to 110°C and the resultant compound is extracted by a solvent.
- the solvent is preferably hexane or petroleum.
- the acid catalyst is typically a strong acid, such as sulphuric acid and is preferably concentrated sulphuric acid.
- the present invention provides an artificially synthesized compound, the properties of which in many respects are analogous to corresponding properties of naturally occurring jojoba oil.
- the artificially synthesized compound has the empirical formula C 4Q H_ 8 0 , and more preferably the compound is characterized by having an infra-red spectrograph substantially as illustrated in figure 1.
- Figure 1 shows an infra-red spectrograph of one form of the compound of the present invention as described herein having the empirical formula C 0 H_ g O 2 ,
- Figure 2 shows an infra-red spectrograph of refined natural jojoba oil
- Figure 3 shows an infra-red spectrograph of WICKENOL 139
- Figure 4 shows an infra-red spectrograph of SHEROBA OIL.
- a reaction mixture is obtained by adding each of the above indicated reactants together in the proportion as indicated above.
- the reaction mixture is heated with stirring for approximately 2 hours at about 100°C in a water or oil bath.
- About 200 ml of water is added to the heated reaction mixture and the reaction mixture is then extracted from the water with hexane or petroleum ether in triplicate using 60 ml for each extraction (3 x 60 ml) .
- the ether or hexane extracts are then combined into a single solution and are kept overnight over anhydrous Na_S0. to remove any remaining traces of water.
- the solution is filtered and the solvent removed under reduced pressure to yield the ester.
- the amount of ester produced is about41.4 grams which corresponds to about 82% yield.
- the yellow colour of the product is optionally removed by passing the product through activated silica.
- the material made by Example I was subjected to column chromatography and a sample of the eluted material taken. The infra-red spectrograph was obtained using this sample of the eluted material.
- the infra-red spectra of naturally occurring jojoba oil exhibits peaks at the following locations,
- the compound forming the subject matter of the present invention as evidenced by the infra-red spectra of Figure 1 has an infra-red spectra which mimics that obtained from naturally refined jojoba oil as is evidenced by the spectra shown in Figure 2, and thus may be regarded as an artificially derived synthetic substitute for naturally occurring jojoba oil.
- a reaction mixture is obtained by adding each of the following reactants together:
- the product is an ester which is coloured, and has a detectable odour.
- a reaction mixture is obtained by adding each of the following reactants together:
- the product is an ester which is solid at room temperature.
- a reaction mixture is obtained by adding each of the following reactants together:
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A compound, the properties of which in many respects are analogous to corresponding properties of naturally occurring jojoba oil, is synthesized by sujecting material containing a precursor of the compound to a transesterification reaction to yield the compound. Preferably, the compound is synthesized by transesterifying erucic acid with 2-octyldodecanol in the presence, as catalyst, of concentrated sulphuric acid.
Description
ARTIFICIAL JOJOBA OIL Technical Field This invention relates generally to an artificially synthesized compound, the properties of which are analogous to certain of the properties of naturally occurring jojoba oil, and to a method of producing the artificially synthesized compound.
Background of the Invention Although the present invention will be described with particular reference to artificially synthesized jojoba oil and to a method of producing this material it is to be noted that the scope of the present invention is not so limited but may extend to include other similar materials and methods. Natural jojoba oil has been known for centuries for its lubricant and moisturising properties, and is of a neutral pH. Previous attempts have been made to produce artifical jojoba oil due to the high cost and problems associated with the availability of the natural product. However, such attempts have not been entirely satisfactory.
The icken Chemical Company of U.S.A., produced a product under the name of WICKENOL 139 which is styled along the lines of a Synthetic jojoba oil. It is believed that WICKENOL 139 is an ester formed from unsaturated straight chain acids, predominantly C__-containing acids and branched chain alcohols, predominantly C -containing acids and thus, has the empirical formula Cχ H_Q0_. WICKENOL 139 is characterized by the infra-red spectrograph as shown in figure 3. Scher Chemicals Inc describe the production of an oil (known as SCHEROBA OIL) in GB 2106507 which the applicants believe to be an ester comprising predominantly isostearylerucyl enucate. GB 2106507 discloses the use of alcohols with odd numbers of carbon atoms. SCHEROBA OIL is characterized by the infra-red spectrograph as shown in figure 4.
The aforementioned artifical oils are not entirely satisfactory. For example, the lubricity does not equal that of the naturally occurring jojoba oil.
Jojoba oil, both naturally occurring and artificially derived has many known commercial uses, which include such uses as high temperature lubricants, additives to mineral oil to improve their lubricity, additives and/or bases for cosmetic and skin care products such as moisturises, use in electronic components, slip agents in plastic films, leather softening agents, anti-foam agents in preparations of penicillin and tetracyclin, non-corrosive permanent lubricants for scientific instruments and robotics and the like. Naturally occurring jojoba oil is composed of esters of monounsaturated straight-chain alcohols and acids. Following intensive research, the present inventors have found a method for preparing a compound, the properties of which in many respects are analogous to the corresponding properties of a naturally occurring jojoba oil. One preferred method involves the use of mustard seeds having a high erucic acid content, from which mustard seed oil is extracted and transesterified. Mustard seed crops are readily grown in Australia and elsewhere in the world and yield good quantities of mustard seed oil (typically one tonne per hectare) . Typically, the oil yield from mustard seed which is available for processing is in the order of 35% by weight.
Summary of the Invention In a first aspect, the present invention provides a method of producing an artificially synthesized compound, the properties of which in many respects are analogous to corresponding properties of naturally occurring jojoba oil, the method comprising subjecting material containing a precursor of the said compound to a transesterification reaction and yielding the said compound.
Preferably, the precursor is erucic acid, an erucic acid containing material, or a mixture thereof.
It is further preferred that the alcohol is a branched-chain alcohol, more preferably, 2-octyldodecanol (C n). which is marketed by Henckel Chemicals under the trade name Eutanol G, stearyl alcohol (C-8) , cetyl alcohol ( ι_ι) ' 1-eicosanol ( 2Q) , 2-eicosanol (C2Q) , oleyl alcohol, isomers thereof, or a mixture of one or more thereof.
It is further preferred that the material containing the percursor comprises material obtained from vegetable oils containing at least 2-66% erucic acid residues, mustard (Brassica) species, rape (high-erucic) species, Crambe abyssinica, or naturally occurring jojoba. Typically, the erucic acid is combined with other acids. More typically the acid reactant of the transesterification reaction is a combination or collection of all of the acids present in the parent mustard seed oil or mustard oil. However, it is to be noted that any suitable alcohol, acid or catalyst may be used in the practice of the present invention. Furthermore, it is to be noted that sources other than mustard seed may be used to obtain artificially derived jojoba oil and such sources include seed of rapeseed varieties whose oil is high in erucic acid content.
Preferred additional acids include oleic acid (C18:l), eicosenoic acid (C20:l), erucic acid (C22:l), nervonic acid (C24:l), linoleic acid (C18:2), or a mixture of one or more thereof.
Typically, the transesterification reaction mixture is heated for up to six hours at a temperature of up to 110°C and the resultant compound is extracted by a solvent. The solvent is preferably hexane or petroleum. The acid catalyst is typically a strong acid, such as sulphuric acid and is preferably concentrated sulphuric acid.
In a second aspect, the present invention provides an artificially synthesized compound, the properties of which in many respects are analogous to corresponding properties of naturally occurring jojoba oil.
Preferably, the artificially synthesized compound has the empirical formula C4QH_80 , and more preferably
the compound is characterized by having an infra-red spectrograph substantially as illustrated in figure 1. Best Mode of Carrying out the Invention Preferred embodiments of the present invention will now be described by way of Example only( which are not to limit the scope of the invention in any way) with reference to the accompanying drawings in which:
Figure 1 shows an infra-red spectrograph of one form of the compound of the present invention as described herein having the empirical formula C 0H_gO2,
Figure 2 shows an infra-red spectrograph of refined natural jojoba oil,
Figure 3 shows an infra-red spectrograph of WICKENOL 139, and Figure 4 shows an infra-red spectrograph of SHEROBA OIL.
Example 1
Mustard seed oil 25 grams
2-octyldodecanol 25 grams concentrated H SO 1-2 grams
A reaction mixture is obtained by adding each of the above indicated reactants together in the proportion as indicated above. The reaction mixture is heated with stirring for approximately 2 hours at about 100°C in a water or oil bath. About 200 ml of water is added to the heated reaction mixture and the reaction mixture is then extracted from the water with hexane or petroleum ether in triplicate using 60 ml for each extraction (3 x 60 ml) . The ether or hexane extracts are then combined into a single solution and are kept overnight over anhydrous Na_S0. to remove any remaining traces of water. The solution is filtered and the solvent removed under reduced pressure to yield the ester. Typically, the amount of ester produced is about41.4 grams which corresponds to about 82% yield. The yellow colour of the product is optionally removed by passing the product through activated silica.
The material made by Example I was subjected to column chromatography and a sample of the eluted material taken. The infra-red spectrograph was obtained using this sample of the eluted material. The infra-red spectra of naturally occurring jojoba oil exhibits peaks at the following locations,
(i) a very strong triplet from 3000 to 2800, (ii) a moderately strong peak at about 1740, (iii) two weak single peaks at i470 and 1170, respectively.
As can be readily seen from a comparison of Figures 1 and 2, the compound forming the subject matter of the present invention as evidenced by the infra-red spectra of Figure 1 has an infra-red spectra which mimics that obtained from naturally refined jojoba oil as is evidenced by the spectra shown in Figure 2, and thus may be regarded as an artificially derived synthetic substitute for naturally occurring jojoba oil.
The spectra of WICKENOL 139 shown in Figure 3 and that of SCHEROBA OIL shown in Figure 4 both contain additional peaks in the region 1400 to 1100 which illustrates that the compound produced by the present invention is more closely related to the naturally refined jojoba oil than is either WICKENOL 139 or SCHEROBA OIL.
Similar methods to those described for Example 1 were used to produce further synthetic substitutes for naturally occurring jojoba oil:
Example 2
A reaction mixture is obtained by adding each of the following reactants together:
High erucic acid rapeseed oil plus equal weight of oolleeyyll aallcciohol (cis-9-octadecen-l-o__) with H 2„S04„ catalyst.
The product is an ester which is coloured, and has a detectable odour.
Example 3
A reaction mixture is obtained by adding each of the following reactants together:
High erucic acid rapeseed oil plus equal weight of stearyl alcohol (octadecon-l-ol) with H SO. catalyst.
The product is an ester which is solid at room temperature.
Example 4
A reaction mixture is obtained by adding each of the following reactants together:
High erucic acid rapeseed oil plus equal weight cetyl alcohol (hexadecan-1-ol) gives ester product which is a solid at room temperature.
High erucic mustard seed oil was used in the above trials with similar results.
Claims
1. A method of producing an artificially synthesized compound, the properties of which in many respects are analogous to corresponding properties of naturally occurring jojoba oil, the method comprising subjecting material containing a precursor of the compound to a transesterification reaction to yield the compound.
2. A method as claimed in claim 1 wherein the precursor is erucic acid, an erucic acid containing material, or a mixture thereof which is transesterified with an alcohol in the presence of an acid catalyst.
3. A method as claimed in claim 2 wherein the alcohol is a branched-chain alcohol, stearyl alcohol (C.-) , cetyl alcohol (C..) , 1-eicosonol (C_0) , 2-eicosanol (C2Q) , isomers thereof, or a mixture of one or more thereof.
4. A method as claimed in 3 wherein the alcohol is 2-octyl dodecanol or oleyl alcohol.
5. A method as claimed in any one of the preceding claims wherein the material containing the precursor comprises material obtained from one or more of the following sources: vegetable oils containing at least 2-66% erucic acid residues, mustard (Brassica) species, rape (high-erucic) species, Crambe abyssinica or naturally occurring jojoba.
6. A method as claimed in claim 5 wherein the material containing the precursor further comprises oleic acid (C18:l), eicosenoic acid (C20:l), erucic acid (C22:l), nervonic acid (C24:l), linoleic acid (C18:2), or a mixture of one or more thereof.
7. A method as claimed in any one of claims 1-4 wherein the material containing the precursor is mustard seed oil or oil extracted from mustard seed.
8. A method as claimed in any one of the preceding claims wherein the transesterification reaction mixture is heated for up to six hours at a temperature of up to 110°C.
9. A method as claimed in any one of the preceding claims wherein the solvent for the transesterification reaction is water.
10. A method as claimed in any one of the preceding claims wherein the compound is extracted from the transesterification reaction mixture by a solvent.
11. A method as claimed in claim 10 wherein the solvent is hexane or petroleum.
12. A method as claimed in any one of the preceding claims wherein the acid catalyst is sulphuric acid.
13. A method as claimed in claim 12 wherein the sulphuric acid is concentrated sulphuric acid.
14. A method of producing an artificially synthesised compound, the properties of which in many respects are analogous to the corresponding properties of naturally occuring jojoba oil substantially as described herein with reference to any one of the Examples.
15. An artificially synthesized compound, the properties of which in many respects are analogous to the corresponding properties of naturally occurring jojoba oil, having subtantially the infra-red spectrograph as shown in Figure 1.
16. An artificially synthesised compound, the properties of which in many respects are analogous to the corresponding properties of naturally occuring jojoba oil, prepared by a method as claimed in any one of claims 1-14.
17. An artificially synthesised compound, the properties of which in many respects are analagous to the corresponding properties of naturally occurring jojoba oil substantially as described herein with reference to any one of the Examples.
18. An artificially synthesised compound as claimed in any one of claims 15-17 having the empirical formula
C40H78°2-
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AUPJ466089 | 1989-06-09 | ||
| AUPJ4660 | 1989-06-09 | ||
| AUPJ6195 | 1989-09-06 | ||
| AUPJ619589 | 1989-09-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1990015127A1 true WO1990015127A1 (en) | 1990-12-13 |
Family
ID=25643698
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/AU1990/000253 WO1990015127A1 (en) | 1989-06-09 | 1990-06-08 | Artificial jojoba oil |
Country Status (1)
| Country | Link |
|---|---|
| WO (1) | WO1990015127A1 (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994002651A1 (en) * | 1992-07-18 | 1994-02-03 | Henkel Kommanditgesellschaft Auf Aktien | Use of guerbet alcohols to prevent the formation of fatty spew on leather |
| WO1994002649A2 (en) * | 1992-07-18 | 1994-02-03 | Henkel Kommanditgesellschaft Auf Aktien | Use of non-ionic organic dialkyl compounds to prevent the formation of fatty spew on leather |
| WO1999037274A2 (en) * | 1998-01-22 | 1999-07-29 | International Flora Technologies, Ltd. | Dry emollient compositions |
| FR2792190A1 (en) * | 1999-04-16 | 2000-10-20 | Sophim | Non-greasy wax-ester emollients for use in skin care preparations obtained by interesterification of triglycerides with an alcohol, distilling off residual alcohol, decolorizing and fridge or hydrogenating the product |
| WO2002002498A1 (en) * | 2000-07-04 | 2002-01-10 | Sophim | Method for producing a non-fatty softener based on wax-esters |
| WO2002010114A2 (en) * | 2000-08-02 | 2002-02-07 | Mj Research & Development, L.P. Of Which Mjrd, Llc Is A General Partner | Transesterified fatty esters for lubricant and refrigerant oil system |
| USRE38141E1 (en) * | 1997-10-17 | 2003-06-10 | International Flora Technologies Ltd. | Dry emollient compositions |
| WO2017040720A1 (en) * | 2015-08-31 | 2017-03-09 | International Flora Technologies, Ltd. | Processes and systems for catalytic manufacture of wax ester derivatives |
| US10435726B2 (en) | 2014-12-19 | 2019-10-08 | International Flora Technologies, Ltd. | Processes and systems for catalytic manufacture of wax ester derivatives |
| US11248245B2 (en) | 2014-12-19 | 2022-02-15 | International Flora Technologies, Ltd. | Processes and systems for catalytic manufacture of wax ester derivatives |
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| EP0069946A1 (en) * | 1981-07-10 | 1983-01-19 | CIRTA Centre International de Recherches et de Technologies Appliquées | Oil, its preparation and its use, particularly in cosmetics |
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| JPS58148836A (en) * | 1982-02-27 | 1983-09-05 | Shinei Kagaku Kk | 13-docosenoic acid ester and cosmetic containing the same |
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Cited By (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994002649A2 (en) * | 1992-07-18 | 1994-02-03 | Henkel Kommanditgesellschaft Auf Aktien | Use of non-ionic organic dialkyl compounds to prevent the formation of fatty spew on leather |
| WO1994002649A3 (en) * | 1992-07-18 | 1994-05-11 | Use of non-ionic organic dialkyl compounds to prevent the formation of fatty spew on leather | |
| US5468255A (en) * | 1992-07-18 | 1995-11-21 | Henkel Kommanditgesellschaft Auf Aktien | Use of nonionic organic dialkyl compounds for preventing fatty spew on leather |
| US5476517A (en) * | 1992-07-18 | 1995-12-19 | Henkel Kommanditgesellschaft Auf Aktien | Use of guerbet alcohols for preventing fatty spew on leather |
| WO1994002651A1 (en) * | 1992-07-18 | 1994-02-03 | Henkel Kommanditgesellschaft Auf Aktien | Use of guerbet alcohols to prevent the formation of fatty spew on leather |
| USRE38141E1 (en) * | 1997-10-17 | 2003-06-10 | International Flora Technologies Ltd. | Dry emollient compositions |
| US6280746B1 (en) | 1997-10-17 | 2001-08-28 | International Flora Technologies Ltd. | Dry emollient compositions |
| WO1999037274A2 (en) * | 1998-01-22 | 1999-07-29 | International Flora Technologies, Ltd. | Dry emollient compositions |
| WO1999037274A3 (en) * | 1998-01-22 | 1999-09-30 | Int Flora Technologies Ltd | Dry emollient compositions |
| FR2792190A1 (en) * | 1999-04-16 | 2000-10-20 | Sophim | Non-greasy wax-ester emollients for use in skin care preparations obtained by interesterification of triglycerides with an alcohol, distilling off residual alcohol, decolorizing and fridge or hydrogenating the product |
| WO2002002498A1 (en) * | 2000-07-04 | 2002-01-10 | Sophim | Method for producing a non-fatty softener based on wax-esters |
| US6596886B1 (en) | 2000-07-04 | 2003-07-22 | Sophim | Method for producing a non-fatty softener based on wax-esters |
| WO2002010114A2 (en) * | 2000-08-02 | 2002-02-07 | Mj Research & Development, L.P. Of Which Mjrd, Llc Is A General Partner | Transesterified fatty esters for lubricant and refrigerant oil system |
| WO2002010114A3 (en) * | 2000-08-02 | 2002-08-15 | Mj Res & Dev L P Of Which Mjrd | Transesterified fatty esters for lubricant and refrigerant oil system |
| US7252779B2 (en) | 2000-08-02 | 2007-08-07 | Mj Research Limited Partnership | Transesterification composition of fatty acid esters, and uses thereof |
| US7968504B2 (en) | 2000-08-02 | 2011-06-28 | MJ Research and Development, LP | Transesterification composition of fatty acid esters, and uses thereof |
| US10435726B2 (en) | 2014-12-19 | 2019-10-08 | International Flora Technologies, Ltd. | Processes and systems for catalytic manufacture of wax ester derivatives |
| US11248245B2 (en) | 2014-12-19 | 2022-02-15 | International Flora Technologies, Ltd. | Processes and systems for catalytic manufacture of wax ester derivatives |
| US11767543B2 (en) | 2014-12-19 | 2023-09-26 | Cargill, Incorporated | Processes and systems for catalytic manufacture of wax ester derivatives |
| US11767544B2 (en) | 2014-12-19 | 2023-09-26 | Cargill, Incorporated | Processes and systems for catalytic manufacture of wax ester derivatives |
| US11773418B2 (en) | 2014-12-19 | 2023-10-03 | Cargill, Incorporated | Processes and systems for catalytic manufacture of wax ester derivatives |
| WO2017040720A1 (en) * | 2015-08-31 | 2017-03-09 | International Flora Technologies, Ltd. | Processes and systems for catalytic manufacture of wax ester derivatives |
| IL257722A (en) * | 2015-08-31 | 2018-04-30 | International Flora Tech Ltd | Processes and systems for catalytic manufacture of wax ester derivatives |
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