WO2008110168A1 - Preparation of 2-isomers of propylene glycol monoesters - Google Patents
Preparation of 2-isomers of propylene glycol monoesters Download PDFInfo
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- WO2008110168A1 WO2008110168A1 PCT/DK2007/050031 DK2007050031W WO2008110168A1 WO 2008110168 A1 WO2008110168 A1 WO 2008110168A1 DK 2007050031 W DK2007050031 W DK 2007050031W WO 2008110168 A1 WO2008110168 A1 WO 2008110168A1
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- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/62—Carboxylic acid esters
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- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
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Abstract
The present invention relates to a method of preparing a composition of 2-propylene glycol monoesters of a fatty acid (2-PGME), and particularly to such a method involving hydrolysis or alcoholysis of esterified fatty acids of 1-propylene glycol monoesters of a fatty acid (1-PGME) or propylene glycol diester of fatty acids (PGDE) by means of a position specific enzyme.
Description
PREPARATION OF 2-ISOMERS OF PROPYLENE GLYCOL MONOESTERS
TECHNICAL FIELD OF THE INVENTION The present invention relates to a method of preparing a composition of 2-propylene glycol monoesters of a fatty acid (2-PGME), and particularly to such a method involving hydrolysis or alcoholysis of esterified fatty acids of 1-propylene glycol monoesters of a fatty acid (1-PGME) or propylene glycol diester of fatty acids (PGDE) by means of a position specific enzyme.
BACKGROUND OF THE INVENTION
Propylene glycol monoesters of fatty acids, and particularly 2-PGME, has recently proven to be useful emulsifiers in a number of food products. The preparation of 2-PGME has, however, previously been very burdensome.
Preparation of 1-PGME and 2-PGME was described by J. B. Martin and E. S. Lutton, JOACS,
43, 1965.
In that paper the authors described the preparation of 2-propylene monoester of stearic acid by several steps. In the first step they prepared a mixture of tetrahγdropyranyl ethers of propylene glycol. Secondly, they divided 1- tetrahydropyranyl ether from 2- tetrahydropyranyl ether by several isolation steps. Thirdly, they reacted 1- tetrahydropyranyl ether with stearoyl chloride to form l-tetrahydropyranyl-2-stearoyl propylene glycol. Finally, they performed a reaction with boric acid, and isolated 2-stearoyl propylene glycol from the reaction mixture.
The method described by J. B. Martin and E. S. Lutton involves the use of several toxic chemicals and several costly protection and deprotection steps, thus limiting its usefulness of the method for production in large scale as well as for production of food additives.
SUMMARY OF THE INVENTION
Thus, an object of the present invention is to reduce or remove the problems associated with the prior art.
Particularly, it is an object of the present invention to provide simple methods for preparing 2-PGME, that is, method containing as few steps as possible.
Additionally, it is an object of the present invention to provide methods that reduce the need for toxic chemical.
The present invention is based on the surprising discovery that 2-propylene glycol monoester of a fatty acid (2-PGME) may be efficiently prepared using position specific enzyme for hydrolysing or alcoholysing propylene glycol diester of a fatty acid (PGDE) .
Thus, an aspect of the invention relates to a method of preparing a composition comprising 2-propylene glycol monoester of a fatty acid (2-PGME), the method comprising the steps: a) providing a mixture comprising propylene glycol diester of a fatty acid (PGDE), a position specific enzyme, and water and/or alcohol, b) hydrolysing or alcoholysing the ester bond at the 1-position of the PGDE using the position specific enzyme as catalyst, thus forming 2-PGME, c) optionally, isolating the 2-PGME, thus forming the composition comprising 2-PGME.
Additionally, the position specific enzyme may be used for enriching 2-PGME relative to 1- propylene glycol monoester of a fatty acid (1-PGME) in mixtures containing both 2-PGME and 1-PGME.
Another aspect of the present invention relates to a method of preparing a composition comprising 2-propylene glycol monoester of a fatty acid, the method comprising the steps: i) providing a mixture comprising a 1-propylene glycol monoester of a fatty acid (1- PGME), a 2-propylene glycol monoester of a fatty acid (2-PGME), a position specific enzyme, and water and/or alcohol, ii) hydrolysing or alcoholysing the ester bond at the 1-position of the 1-PGME using the position specific enzyme as catalyst, iii) optionally, isolating the 2-PGME, thus forming the composition comprising 2-PGME.
In the context of the present invention, the verb "alcoholyse" means performing alcoholysis, ie. interesterification between propylene glycol ester and an alcohol.
Yet another aspect of the present invention relates to a composition comprising 2-PGME obtainable by the methods of the invention.
The present invention will now be described in more detail in the following.
DETAILED DESCRIPTION OF THE INVENTION In the context of the present invention, the term "2-propylene glycol monoester of a fatty acid", abbreviated "2-PGME", relates to a monoester of a fatty acid and propane-l,2-diol, said monoester having the general formula I,
In the context of the present invention, the term "1-propylene glycol monoester of a fatty acid", abbreviated "1-PGME", relates to a monoester of a fatty acid and propane-l,2-diol, said monoester having the general formula II
Preparation of the 2-PGME and 1-PGME is well known to the person skilled in the art, e.g. in Martin and Lutton, the contents of which are incorporated herein by reference. The preparation of the 2-PGME and 1-PGME may e.g. involve esterification using protection groups to protect either the 1-hydroxy or the 2-hydroxy group. Alternatively, 2-PGME or 1- PGME may be provided by isolating the individual molecular species from a mixture of 2- PGME and 1-PGME by means of chromatography.
In the context of the present invention, the term "propylene glycol diester of a fatty acid ", abbreviated "PGDE", relates to a diester of two fatty acids and propane-l,2-diol, said diester having the general formula III
In an embodiment of the invention, at least one fatty acid of the esterified fatty acids of 2- PGME, 1- PGME, or PGDE, comprises from 4 to 24 carbon atoms, preferably from 12 to 20 carbon atoms and even more preferably from 16-18 carbon atoms.
In useful embodiments of the invention, one or more of the fatty acids of the 2-PGME, 1- PGME, or PGDE, are derived from one or more of the fatty acid sources selected from the group consisting of sunflower oil, sunflower seed oil, palm oil, palm kernel oil, coconut oil, rape seed oil, soya bean oil, shea oil, ricinus oil, and a mixture thereof. The fatty acid sources may e.g. be the native fatty acid sources, or fully or partially hydrogenated fatty acid sources.
For examle, the at least one fatty acid may comprise one or more fatty acids selected from the group consisting of decanoic acid, dodecanoic acid, myristic acid, palmitic acid, stearic acid, oleic acid, elaidic acid, linoleic acid, linolenic acid, arachidonic acid, behenic acid, erucic acid, ricinoleic acid, or mixtures thereof.
The at least one fatty acid may e.g. comprise stearic acid, in which case the 2-PGME comprises propylene glycol-2-monostearate.
The position specific enzyme is an enzyme capable of hydrolysing or alcoholysing an ester bond and preferably an enzyme which hydrolytic or alcoholytic activity is specific for 1- position esters, and thus not, or to a lesser degree, for 2-position esters.
In a preferred embodiment of the invention, the position specific enzyme has a rate of hydrolysis or alcoholysis of 2-position esters which is at most 10% of its rate of hydrolysis or alcoholysis of 1-position esters, and preferably at most 1%, such as at most 0.1%, and even more preferably at most 0.01% such as at most 0.001%.
In a preferred embodiment of the invention, the position specific enzyme is not capable of hydrolysing or alcoholysing 2-position esters.
In a preferred embodiment of the invention, the position specific enzyme comprises a position specific lipase, and preferably a 1-specific lipase or a 1,3-specific lipase.
The position specific enzyme may comprise at least one enzyme selected from the group consisting of Lipozyme TL®, Lipozyme TL IM®, Lipozyme RM®, and Lipozyme RM IM®
These lipases are 1,3 specific lipases found in the organisms Thermomyces lanuginosus (TL) and Rhizomucor meihei (RM).
The described Lipozyme lipases are available from Novozyme A/S, Denmark.
In a preferred embodiment of the invention, the position specific enzyme is an immobilised position specific enzyme. An immobilised position specific enzyme comprises the position specific enzyme immobilised to a solid phase. Useful solid phases are e.g. beads, microparticles, paramagnetic or super paramagnetic particles, filters etc. The solid phase may e.g. be dispersed in the mixture or it may be used as a packed or fluidised bed reactor. A presently preferred immobilised position specific enzyme is Lipozyme RM IM®.
The mixture comprises the positions specific enzyme in an amount in the range of 0.001- 30% by weight, preferably in the range of 0.25-25% by weight, such as 0.5-20% by weight, and even more preferably in the range of 1-15% by weight, such as 4-8% by weight.
The weight ratio between the position specific enzyme and the 1-PGME or PGDE in mixture may e.g. range from 1:200 to 1: 1, preferably from 1:50 to 1:2 and even more preferably from 1:20 to 1:5.
The activity of the position specific enzyme is typically measured in terms of IUN (interesterification units), where 1 IUN corresponds to a conversion rate of O.Olg tristearin/L/minute. The IUN of a given enzyme is determined according the procedure
outlined in WO 2005/071053, the contents of which are incorporated herein by reference for all purposes.
In a preferred embodiment of the invention, the mixture of step a) the enzymatic activity of the positions specific enzyme is in the range of 1-27500 IUN per 1 mol of PGDE, preferably in the range of 230-22800 IUN per 1 mol of PGDE, such as 460-18300 IUN per 1 mol of PGDE, and even more preferably in the range of 920-13700 IUN per 1 mol of PGDE, such as 3600-7200 IUN per 1 mol of PGDE.
In a preferred embodiment of the invention, the mixture of step i) the enzymatic activity of the positions specific enzyme is in the range of 1-27500 IUN per 1 mol of 1-PGME, preferably in the range of 230-22800 IUN per 1 mol of 1-PGME, such as 460-18300 IUN per 1 mol of 1-PGME, and even more preferably in the range of 920-13700 IUN per 1 mol of 1-PGME, such as 1800-3600 IUIM per 1 mol of 1-PGME.
In the event that the mixture of step a) or step i) contains both PDME and 1-PGME, the number of enzyme units to be used should be calculated from the combined amount of PGDE and 1-PGME since both molecular species require the position specific enzyme to be hydrolysed or alcoholysed.
The mixture of step a) or step i) typically includes water and/or alcohol.
In the context of the present invention, the term "and/or" used in the context "X and/or Y" should be interpreted as "X", or "Y", or "X and Y".
Thus, the mixture of step a) or step i) may comprise water, it may comprise alcohol, and it may comprise both water and alcohol.
The mixture of step a) may furthermore comprise a 1-PGME and/or a 2-PGME.
The mixture of step i) may furthermore comprise a PGDE.
The alcohol for alcoholysing the 1-ester bond typically comprises a C1-C8^aIcOhOl, preferably a C2-C4 alcohol, and even more preferably a C2-C3 alcohol.
The alcohol may e.g. comprise one or more alcohols selected from the group consisting methanol, ethanol, n-propanol, isopropanol, n-butanol, sec-butanol, n-pentanol, sec- pentanol, n-hexanol, sec-hexanol, n-heptanol, sec-heptanol, n-octanol, sec-octanol, 2- methyl-1-propanol, and a mixture thereof.
In a preferred embodiment of the invention, the alcohol comprises ethanol.
The mixture of step a) may comprise PGDE in an amount in the range of 0.1-99% by weight, preferably in an amount in the range of 1-50% by weight and even more preferably in the an amount in the range of 2.5-20% by weight, such as 5-15% by weight. The mixture of step a) may also comprise 2-PGME, normally in minor amounts. The mixture of step a) may additionally contain 1-PGME.
The mixture of step i) may comprise 1-PGME in an amount in the range of 0.1-90% by weight, preferably in an amount in the range of 1-50% by weight and even more preferably in the an amount in the range of 2.5-20% by weight, such as 5-15% by weight. The mixture of step i) may additionally contain PGDE.
The mixture of step i) typically comprises 2-PGME in an amount in the range of 0.1-90% by weight, preferably in an amount in the range of 1-50% by weight and even more preferably in the an amount in the range of 2.5-25% by weight, such as 5-15% by weight.
In an embodiment of the invention, the mixture comprises a solvent, preferably an organic solvent. For example, the solvent may be acetone, methyl t-butyl ether, or a combination thereof.
When the mixture of step a) or step i) comprises a solvent, the solvent is typically present in the mixture in an amount in the range of 1-99% by weight of the mixture, preferably in an amount in the range of 20-90% by weight of the mixture, and even more preferably in the range of 30-80% by weight of the mixture.
In step b) or step ii) the ester bond at the 1-position of the PGDE or 1-PGME is hydrolysed or alcoholysed the using the position specific enzyme as catalyst. In step b) this results in the formation of 2-PGME. In step ii) this results in conversion of 1-PGME into propylene glycol and fatty acid alcohol ester. Step ii) does not generate more 2-PGME but increases the ratio between 2-PGME and 1-PGME by degrading 1-PGME.
The hydrolysis or alcoholysis of step b) or step ii) is typically performed at a temperature in the range of 20-950C, preferably in the range of 30-700C, and even more preferred in the range of 40-600C.
In step b), the hydrolysis or alcoholysis is typically performed until a sufficient amount of the PGDE has been converted to 2-PGME.
In step ii), the hydrolysis or alcoholysis is normally performed until the desired ratio between 2-PGME and 1-PGME has been achieved. The desired molar ratio between 2-PGME and 1-PGME in the end-product is typically in the range of 1: 10 to 10: 1.
The reaction time, i.e. the duration of the hydrolysis or alcoholysis of step b) or step ii), may be adjusted based on the specific composition of the mixture and the temperature used during reaction. Higher concentration or number of units of the position specific enzyme and higher temperature typically speed up the reaction and reduces the necessary reaction time. The reaction time may e.g. be in the range of 0.1-96 hours, such as 1-48 hours, and preferably in the range of 5-36 hours, and even more preferably in the range of 10-24 hours.
It is envisioned that the method of the invention e.g. may be implemented as a batch process or as a continuous process.
The methods of the invention may optionally contain an additional step c) or step iii) wherein the 2-PGME obtained from step b) or step ii), respectively, is isolated.
The isolation typically involves removal of the position specific enzyme. The position specific enzyme may e.g. be removed by filtration, sedimentation, or centrifugation. When the position specific enzyme is immobilised on a paramagnetic or super paramagnetic solid phase, the solid phase-bound position specific enzyme may be removed from the reaction products by magnetic separation techniques.
The isolation of 2-PGME may e.g. involve molecular distillation, fractionation or recrystallisation. H. Szelag and W. Zwierzykowski, Fett, Seifen, Anstrichmittel, Vol. 85, issue 11, p 443-446, 1983, the contents of which is incorporated herein by reference, describe the application of Molecular Distillation. A. E. Thomas and F. R. Paulicka, Chemistry and Industry, p 774-779, 1976, describe the principle in fractionation or recrystallisation of fatty materials., Bailey's Industrial Oil & Fat Products vol. 2 also describe how to fractionate edible oils. The contents of these documents are incorporated herein by reference for all purposes.
It should be noted that embodiments and features described in the context of one of the aspects of the present invention also apply to the other aspects of the invention.
All patent and non-patent references cited in the present application, are hereby incorporated by reference in their entirety.
The invention will now be described in further details in the following non-limiting examples.
EXAMPLES
Analysis equipment: Gas chromatography-mass spectroscopy
Gas chromatography system: Agilent 6890 (Agilent Technologies Inc., USA) Mass spectroscopy system: Agilent 5973 (Agilent Technologies Inc., USA) Software: Agilent MSD Chemstation D.01.02.16 (Agilent Technologies Inc., USA)
Samples were silylated by N-Methyi-N-(trimethylsilyl)trifluoroacetamide (MSTFA) before they were analysed.
Example 1: Preparation of 2-PGMS by alcoholysis of PGDS.
In this example it have been demonstrated that propylene glycol-2-monostearate (2- PGMS) can be made by alcoholysis of propylene glycol-l,2-distearate (PGDS) and without use of solvent.
0.0164 MoI PGDS and 1.640 mol ethanol 99% were charged to a reaction flask. The reaction flask was equipped with a mechanical stirrer, water cooled condenser, thermometer and temperature controlled heating mantel.
The reaction mixture was heated to 500C. Then 75 IUN Lipozyme RM IM (corresponding to 5.0% by weight of propylene glycol distearate) was added and the reaction was started. After 24 hours of reaction, the enzyme was removed by filtration.
The raw reaction product obtained was analysed by GCMS measured as area percentage, and the result is summarised in the table below.
Example 2: Preparation of 2-PGMS using alcoholysis in the presence of solvent.
In this example it has been demonstrated that 2-PGMS can be made using alcoholysis in the presence of solvent.
0.0164 MoI PGDS, 1.640 mol ethanol 99% and 1500 ml methyl t-butylether were charged to a reaction flask. The reaction flask was equipped with a mechanical stirrer, water cooled condenser, thermometer and temperature controlled heating mantel.
The reaction mixture was heated to 50 0C. Then 150 IUN Lipozyme RM IM (corresponding to 10.0% by weight of PGDS) was added and the reaction was started. After 24 hours of reaction, the enzyme was removed by filtration and solvent was evaporated.
The raw reaction product obtained was analysed by GCMS measured as area percentage, and the result is summarised in the table below.
Example 3: Preparation of 2-PGMS using alcoholysis of PGDS in the presence of solvent and reusing the enzyme.
In this example it has been demonstrated that 2-PGMS can be made using alcoholysis of PGDS in the presence of solvent and reusing the enzyme at least 3 times.
Reuse of the same load of Lipozyme RM IM 3 times other wise the same recipe as in example 2. After each reaction, the enzyme was removed by filtration and solvent was
evaporated. The raw reaction products obtained were analysed by GCMS measured as area percentage. The result of the analyses is summarised in the table below.
Example 4: Enrichment of 2-PGMS using degradation of 1-PGMS.
In this example it has been demonstrated that 2-PGMS can be enriched relative to 1-PGMS by degrading the 1-PGMS.
0.0305 MoI propylene glycol monoester (PGMS) and 0.1093 mol ethanol 99% were charged to a reaction flask. The reaction flask was equipped with a mechanical stirrer, water cooled condenser, thermometer and temperature controlled heating mantel.
The reaction mixture was heated to 40 0C. Then 120 IUN Lipozyme RM IM (corresponding to 8.0% by weight of PGMS) was added and the reaction was started. After 0, 2, 4, 7 and 24 hours of reaction, adequate samples were withdrawn from the reaction mixture, without taking up any enzyme.
The obtained samples were analysed by GCMS. The result of the analyses, measured as area percentage, is summarised in the table below.
Example 5: Preparation of 2-PGMS using degradation of 1-PGMS in the presence of a solvent.
In this example it has been demonstrated that 2-PGMS can be made using degradation of 1-PGMS in the presence of a solvent.
0.0061 MoI propylene glycol monoester (a mixture of 1-PGMS and 2-PGMS), 0.0328 mol ethanol 99% and 20 ml methyl ethylacetat were charged to a reaction flask. The reaction flask was equipped with a mechanical stirrer, water cooled condenser, thermometer and temperature controlled heating mantel.
The reaction mixture was heated to 50 0C. Then 30 IUN Lipozyme RM IM (corresponding to 10.0% by weight of propylene glycol monoester) was added and the reaction was started. After 0, 2, 4, 6 and 24 hours of reaction, adequate samples were withdrawn from the reaction mixture, without taking up any enzyme.
The obtained samples were analysed by GCMS. The result of the analyses, measured as area percentage, is summarised in the table below.
In this example it has been demonstrated that 2-PGMS can be made in kilogram scale using degradation of 1-PGMS.
20.0 Kg (61.0 mol) propylene glycol monoester (a mixture of 1-PGMS and 2-PGMS), 7.4 kg (161,6 mol) ethanol 99.9% and 0.2 kg water were charged to a 50 L reaction vessel. .The reaction vessel was equipped with a mechanical stirrer, thermometer and temperature controlled heating of the vessel.
The reaction mixture was heated to 40 0C. Then 1,0 kg (3.5% by weight of the other raw materials - corresponding to 150000 IUN) Lipozyme RM IM was added and the reaction was started. After 0.0, 0.5, 1.5, 3.5, 6.0 and 24.5 hours of reaction, adequate samples were withdrawn from the reaction mixture, without taking up any enzyme.
The obtained samples were analysed by GCMS. The result of the analyses, measured as area percentage, is summarised in the table below.
Example 7: Isolation of PGMS from reaction mixture by distillation.
In this example it has been demonstrated that PGMS can be isolated by distillation.
The reaction mixture obtained after 24.5 hours reaction was vacuum distilled in 4 steps for isolation of PGMS. The parameters in the 4 steps were:
• Step 1. Distillation of ethanol by Thin Film evaporator at temperature 1400C +/-50C and pressure 170 mbar +/-10 mbar.
• Step 2. Distillation of propylene glycol by Thin Film evaporator at 13O0C +/- 50C and pressure 4mbar +/-1 mbar.
• Step 3. Distillation of fatty acid ethyl esters and fatty acids by Short Path evaporator at temperature 1550C +/-50C and pressure 0.5 mbar +/-0.1 mbar. • Step 4. Distillation of PGMS by Short Path evaporator at temperature 1650C
+/-50C and pressure 0.05 mbar +/-0.01 mbar.
Isolation by the described method gives more than 90% purity of PGMS and the isomeric purity in PGMS with more than 60% 2-PGMS.
Claims
1. A method of preparing a composition comprising 2-propylene glycol monoester of a fatty acid (2-PGME), the method comprising the steps: a) providing a mixture comprising propylene glycol diester of a fatty acid (PGDE), a position specific enzyme, and water and/or alcohol, b) hydrolysing or alcoholysing the ester bond at the 1-position of the PGDE using the position specific enzyme as catalyst, thus forming 2-PGME, c) optionally, isolating the 2-PGME, thus forming the composition comprising 2-PGME.
2. A method of preparing a composition comprising 2-propylene glycol monoester of a fatty acid, the method comprising the steps: i) providing a mixture comprising a 1-propylene glycol monoester of a fatty acid (1- PGME), a 2-propylene glycol monoester of a fatty acid (2-PGME), a position specific enzyme, and water and/or alcohol, ii) hydrolysing or alcoholysing the ester bond at the 1-position of the 1-PGME using the position specific enzyme as catalyst, iii) optionally, isolating the 2-PGME, thus forming the composition comprising 2-PGME.
3. The method according to claim 1, wherein the mixture of step a) furthermore comprises a 1-PGME and/or a 2-PGME.
4. The method according to claim 2, wherein the mixture of step i) furthermore comprises a PGDE.
5. The method according to any of the preceding claims, wherein the position specific enzyme is a lipase.
6. The method according to any of the preceding claims, wherein the lipase is a 1,3- specific lipase.
7. The method according to any of the preceding claims, wherein at least one enzyme is selected from the group consisting of Lipozyme TL®, and Lipozyme RM
8. The method according to claim 6 or 7, wherein the mixture comprises 0.001-30% enzyme by weight.
9. The method according to any of any of the preceding claims, wherein the enzymatic activity of the positions specific enzyme in the mixture is in the range of 1-27500 IUN per 1 mol of PGME or per mol PGDE.
5
10. The method according to any of the preceding claims, wherein the mixture comprises 1-PGME in an amount of 0.1-90% by weight.
11. The method according to any of the preceding claims, wherein the mixture comprises 10 2-PGME in an amount of 0.1-90% by weight.
12. The method according to any of the preceding claims, wherein the mixture comprises PGDE in an amount of 0.1-90% by weight.
15 13. The method according to any of the preceding claims, wherein the alcohol for alcoholising the 1-ester bond comprises a C1-C8, preferably a C2-C4 alcohol, and even more preferably a C2-C3 alcohol.
14. The method according to any of the preceding claims, wherein the alcohol for 20 alcoholysing the 1-ester bond comprises one or more alchohols selected from the group consisting methanol, ethanol, n-propanol, isopropanol, n-butanol, sec-butanol, n- pentanol, sec-pentanol, n-hexanol, sec-hexanol, n-heptanol, sec-heptanol, n-octanol, sec- octanol, 2-methyl-l-propanol, and a mixture thereof.
25 15. The method according to any of the preceding claims, wherein the at least one fatty acid comprises from 4 to 24 carbon atoms.
16. The method according to claim 15, wherein the at least one fatty acid comprises fatty acids is derived from a native or hydrogenated fatty acid source selected from the group
30 consisting of sunflower oil, sunflower seed oil, palm oil, palm kernel oil, coconut oil, rape seed oil, soya bean oil, shea oil, ricinus oil, and a mixture thereof.
17. The method according to claim 15, wherein the at least one fatty acid comprises a fatty acid selected from the group consisting of decanoic acid, dodecanoic acid, myristic
35 acid, palmitic acid, stearic acid, oleic acid, elaidic acid, linoleic acid, linolenic acid, arachidonic acid, behenic acid, erucic acid, ricinoleic acid or mixtures thereof.
18. The method according to any of the preceding claims, wherein the hydrolysis or alcoholysis is performed at a temperature in the range of 20-950C.
19. The method according to any of the preceding claims, wherein the hydrolysis or alcoholysis is performed until the ratio between 2-PGME and 1-PGME is 1: 10 to 10: 1.
20. A composition comprising 2-PGME obtainable by the method according to any of the preceding claims.
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| PCT/DK2007/050031 WO2008110168A1 (en) | 2007-03-15 | 2007-03-15 | Preparation of 2-isomers of propylene glycol monoesters |
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06116585A (en) * | 1992-10-09 | 1994-04-26 | Kanegafuchi Chem Ind Co Ltd | Method for purifying fat and oil |
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2007
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06116585A (en) * | 1992-10-09 | 1994-04-26 | Kanegafuchi Chem Ind Co Ltd | Method for purifying fat and oil |
Non-Patent Citations (5)
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| SHAW JEI-FU ET AL: "Optimized enzymatic synthesis of propylene glycol monolaurate by direct esterification.", FOOD CHEMISTRY, vol. 81, no. 1, May 2003 (2003-05-01), pages 91 - 96, XP002459391, ISSN: 0308-8146 * |
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