GB2396611A - Preparation of wax esters by transesterifying esters with alcohols below atmospheric pressure - Google Patents

Preparation of wax esters by transesterifying esters with alcohols below atmospheric pressure Download PDF

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GB2396611A
GB2396611A GB0329456A GB0329456A GB2396611A GB 2396611 A GB2396611 A GB 2396611A GB 0329456 A GB0329456 A GB 0329456A GB 0329456 A GB0329456 A GB 0329456A GB 2396611 A GB2396611 A GB 2396611A
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esters
process according
mixtures
acid
application
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Jeffrey Lee Richardson
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Procter and Gamble Co
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Procter and Gamble Co
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00Preparation of carboxylic acid esters
    • C07C67/03Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/50Improvements relating to the production of bulk chemicals
    • Y02P20/584Recycling of catalysts

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

Abstract

A process for the preparation of wax esters by transesterifying a C2-60 fatty ester with a C1-30 fatty alcohol at a pressure below atmospheric pressure. Wax esters in improved chemical yield or with improved purity, reduced colour or reduced odour may be obtained. The process may be performed in the presence of a catalyst, preferably a non-recyclable basic catalyst such as sodium methylate. The process is preferably performed at a pressure below 0.1 atm and at a temperature between 60 and 100 {C. The wax esters may be useful in home care, fabric care, cosmetics, personal care, pharmaceutical or confectionary applications.

Description

1 2396611
Improved Process for the Preparation of Wax Esters Field of the Invention
This invention relates to lower pressure processes for the preparation of esters, more specifically of wax esters.
5 In particular, this invention relates to the preparation of wax esters with improved chemical yield, with improved purity, with reduced color, with reduced odor or any combination thereof.
Background to the Invention
10 Wax esters are widely used materials, e.g., in the candle making industries, in the cosmetic industries, in the pharmaceutical industries, in the confectionery industries, in the car polish industries and in the shoe polish industries to name a few. The growing demand of wax 15 esters, also known as fatty esters, has generated interest in investigating novel and improved processes of preparing such compounds.
U.S. Patent No. 4,112,235 (issued September 5, 1978; UOP Inc.) describes a transesterification process wherein 20 a specific C2-C8 fatty ester is reacted with a C:-C20 carboxylic acid in the presence of a tin halide catalyst to obtain the corresponding ester of the carboxylic acid. The reaction is performed in an autoclave at a pressure between 1 atm to 100 atm and at temperatures from 0 C to 150 C.
25 The document cited is, in relevant part, incorporated herein by reference; the citation of this document is not to be construed as an admission that it is prior art with
respect to the present invention.
The process mentioned above has at least the following 30 disadvantages: (a) the process is performed at high reaction pressures and therefore requires the use of a relatively complicated reaction vessel; and (b) the process requires an expensive catalyst (which generally must be separated and/or re-cycled from the reaction liquor and/or 35 from the reaction product in an expensive and/or time consuming manner).
Therefore, a need exists for an improved process for the preparation of wax esters to deliver desired wax esters without the common disadvantages known in the art.
As described above, the prior art teaches to perform
5 trans-esterification reactions at atmospheric pressure. The same document teaches to perform trans-esterification reactions at even higher pressures than atmospheric pressure, e.g. up to 150 atmospheres. It is evident from the cited art document that problems occur when using such 10 high pressures. Indeed, it is noted from the example section of U.S. Patent No. 4,112,235 that mixtures of products are obtained by high pressure processes. The prior art does not teach to lower the pressure to perform trans-
esterification processes. We have now surprisingly found 15 that wax esters are obtainable in an improved process under reduced pressure. By utilizing such a process with suitable starting materials, wax esters are obtainable with improved chemical yield, with improved purity, with reduced color, with reduced odor or any combination thereof.
20 Summary of the Invention
The present invention relates to processes for the preparation of wax esters comprising the following reaction step performed under reduced pressure: trans-esterification of C7-C60 fatty esters with C-C30 fatty alcohols.
25 As used herein, "reduced pressure" refers to a pressure below atmospheric pressure. Preferably, the processes of the present invention are performed at a pressure below 0.5 atm, more preferably at a pressure below 0.2 atm, and most preferably at a pressure below 0.1 atm.
30 The processes of the present invention are preferably performed at relatively mild reaction temperatures, or in the presence of a catalyst, or in the presence of an inert solvent, or even at any combination of these conditions. As used herein, "relatively mild reaction temperatures" refers 35 to temperatures below 105 C. Preferably, the reaction temperature is below 100 C, and more preferably the reaction temperature is between 60 C and 100 C.
To prepare the final wax ester by the process of the present invention, one or more additional processing steps may be necessary, e.g., steps in which the intermediate products or final products or raw products are washed, 5 neutralized, separated and/or purified from impurities and/or side products and/or starting materials or any combination thereof.
The present invention also relates to a method of using the wax esters obtained by the processes of the 10 present invention in applications known for utilizing wax esters, including but not limiting to any home care application, fabric care application, cosmetics application, personal care application, pharmaceutical application, confectionery application and any combination 15 thereof. The present invention further relates to the use of the wax esters obtained by the processes of the present invention in any home care application, fabric care application, cosmetics application, personal care application, pharmaceutical application, confectionery 20 application and any combination thereof.
Detailed Description of the Invention
The processes of the present invention provide a way to prepare the desired wax esters with improved chemical yield, with improved purity, with reduced color, with 25 reduced odor or any combination thereof.
The following reaction has been found to be suitable to deliver the desired wax esters under reduced pressure: The reaction of C2-C60 fatty esters with C1-C30 fatty alcohols (trans-esterification).
30It has been found that this reaction performed at reduced pressure for the preparation of such esters provides improvements as mentioned above.
In the chemical reactions of the present invention, the group Ri is selected from the group consisting of 35 hydrogen and C1 to C29 saturated or unsaturated, linear, branched, cyclic, substituted or unsubstituted hydrocarbons, preferably from Cg to Cal saturated or
unsaturated, linear, branched or cyclic, substituted or unsubstituted hydrocarbons and more preferably from Cal to Ci7 saturated or unsaturated, linear, branched or cyclic, substituted or unsubstituted hydrocarbons and mixtures 5 thereof. The group Red is selected from the group consisting of C1 to C30 saturated or unsaturated, linear, branched or cyclic, substituted or unsubstituted hydrocarbons, preferably from ClO to C22 saturated or unsaturated, linear, branched or cyclic, substituted or unsubstituted 10 hydrocarbons and more preferably from C:2 to Cue saturated or unsaturated, linear, branched or cyclic, substituted or unsubstituted hydrocarbons and mixtures thereof. The group R3 is selected from the group consisting of Cat to C30 saturated or unsaturated, linear, branched or cyclic, 15 substituted or unsubstituted hydrocarbons, preferably from Cl to C6 saturated or unsaturated, linear, branched or cyclic, substituted or unsubstituted hydrocarbons and more preferably from Cat to C3 saturated or unsaturated, linear, branched or cyclic, substituted or unsubstituted 20 hydrocarbons and mixtures thereof.
When using the term substituted, it is meant that the respective hydrocarbon chain may comprise any heteroatom in addition to already containing carbon and hydrogen. Non-
limiting examples of heteroatoms useful herein include 25 silicone, nitrogen, phosphorous, arsenic, oxygen, sulfur, fluorine, chlorine, bromine, iodine, and mixtures thereof.
These heteroatoms may be part of the main carbon chain or of a functional group attached to the main carbon chain of the hydrocarbon. When using the term unsubstituted, it is 30 meant that the respective hydrocarbon chain only contains carbon and hydrogen and none of the above-mentioned heteroatoms. Non-limiting examples of suitable esters to be used in the processes of the present invention include any C2 to C60 35 esters derivable from formic acid, acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, 2-ethyl hexanoic acid, oenanthylic acid, caprylic acid, pelargonic
acid, capric acid, undecylic acid, lauric acid, tridecoic acid, myristic acid, pentadecanonic acid, palmitic acid, margaric acid, stearic acid, arachidic acid, behenic acid, cyclopentanecarboxylic acid, cyclohexanecarboxylic acid, 5 cycloheptanecarboxylic acid, cyclooctanecarboxylic acid, benzoic acid, phentylacetic acid, phenylpropionic acid, phenylbutyric acid, o-toluic acid, m-toliuc acid, ptoluic acid, naphthalenecarboxylic acid, acryclic acid, crotonic acid, isocrotonic acid, tiglic acid, angelic acid, 10 senecioic acid, myristoleic acid, palmitoleic acid, oleic acid, linoleic acid, linolenic acid, eleosteraic acid, eicosenic acid, erucic acid, oxalic acid, malonic acid, succinic acid, glutaric acid, sebacic acid, brassic acid, amleic acid, boxylic acid and mixtures thereof.
15 Preferably, suitable esters to be used in the processes of the present invention include methyl laureate, ethyl laureate, propyl laureate, isopropyl laureate, methyl myristate, ethyl myristate, propyl myristate, isopropyl myristate, methyl palmitate, ethyl palmitate, propyl 20 palmitate, isopropyl palmitate, methyl stearate, ethyl stearate, propyl stearate, isopropyl stearate, methyl myristoleate, ethyl myristoleate, propyl myristoleate, isopropyl myristoleate, methyl palmitoleate, ethyl palmitoleate, propyl palmitoleate, isopropyl palmitoleate, 25 methyl oleate, ethyl oleate, propyl oleate, isopropyl oleate, methyl linoleate, ethyl linoleate, propyl linoleate, isopropyl linoleate, and mixtures thereof. More preferably, suitable esters to be used in the processes of the present invention include methyl palmitate, ethyl 30 palmitate, propyl palmitate, isopropyl palmitate, methyl stearate, ethyl stearate, propyl stearate, isopropyl stearate, methyl palmitoleate, ethyl palmitoleate, propyl palmitoleate, isopropyl palmitoleate, methyl oleate, ethyl oleate, propyl oleate, isopropyl oleate, and mixtures 35 thereof. Most preferably, suitable esters to be used in the processes of the present invention include ethyl palmitate, isopropyl palmitate, ethyl stearate, isopropyl stearate,
ethyl palmitoleate, isopropyl palmitoleate, ethyl oleate, isopropyl oleate, and mixtures thereof.
Non-limiting examples of suitable alcohols to be used in the processes of the present invention include methanol, 5 ethanol, propanol, butanol, pentanol, hexanol, 2-ethyl hexanol, heptanol, octanol, nonanol, decanol, undecanol, dodecanol, lauryl alcohol, tridecyl alcohol, myristiryl alcohol, pentadecyl alcohol, palmyl alcohol, margaryl alcohol, stearyl alcohol, arachyl alcohol, behenyl alcohol, 10 cyclopentanol, cyclohexanol, cycloheptanol, cyclooctanol, phenol, and mixtures thereof. Preferably, suitable alcohols to be used in the processes of the present invention include decanol, undecanol, dodecanol, lauryl alcohol, tridecyl alcohol, myristiryl alcohol, pentadecyl alcohol, 15 palmyl alcohol, margaryl alcohol, stearyl alcohol, arachyl alcohol, behenyl alcohol, and mixtures thereof. More preferably, suitable alcohols to be used in the processes of the present invention include dodecanol, lauryl alcohol, tridecyl alcohol, myristiryl alcohol, pentadecyl alcohol, 20 palmyl alcohol, margaryl alcohol, stearyl alcohol, and mixtures thereof.
The esters and alcohols suitable for use in the present invention can be of natural or synthetic origin.
The ratio of the fatty esters to the fatty alcohols in 25 the processes of the present invention ranges from about 10:1 to about 1:10, preferably from about 5:1 to about 1:5, more preferably from about 2:1 to about 1:2, even more preferably from about 1.2:1 to about 1:1.2 and most preferably from about 1.05:1 to about 1:1.05.
30 In the processes of the present invention, it is required that side products formed during the reaction are withdrawn at least in part from the reaction mixture.
Preferably, the side products are continuously withdrawn at least in part from the reaction mixture. For a trans 35 esterification reaction, the side product is typically an alcohol. In order to withdraw the side products, the pressure inside the reaction vessel is set below
atmospheric pressure, preferably at a pressure below 0.5 atm, more preferably at a pressure below 0.2 atm, and most preferably at a pressure below 0.1 atm. Without being bound by theory, it is believed that the improved chemical yield 5 of wax ester products obtained from the processes of the present invention results from driving the reaction until its completion by the continuous removal of side products.
It is further believed that the improved purity, the reduced color, the reduced odor or any combination thereof 10 also result from reducing the pressure in the reaction vessel. Furthermore, the withdraw of side products may be assisted by an inert gas flow, e.g. nitrogen, and/or argon, passing through the reaction mixture to further 15 the stripping effect of the reduced pressure.
Alternatively or in addition to using an inert gas, the withdraw of side products may be assisted by applying heat to the reaction vessel. However, it is preferred that the temperature is maintained below 105 C at any 20 time during the process.
In order to substantially remove the side products from the reaction mixtures, it is preferred to have a combination of reducing the pressure inside the reaction vessel and applying heat.
25 In a preferred embodiment of the present invention, the processes of the present invention are performed under relatively mild conditions. This means that in a preferred embodiment, the reaction temperature inside the reaction vessel is below 105 C, preferably the reaction temperature 30 is below 100 C, and more preferably the reaction temperature is between 60 C and 100 C.
Without being bound by theory, it is believed that the improved purity is also effected by these relatively mild reaction conditions. It is believed that these relatively 35 mild reaction conditions reduce the possibility of unwanted side reactions, thereby increasing the chemical yield of desired wax esters.
Unwanted side products often cause an undesired darkening and/or off odor formation, e.g., a brownish color and/or a burnt odor of the wax esters. By preventing the formation of side products, the desired wax esters in 5 themselves can be obtained in reduced color and/or in reduced odor, which is specifically true for the wax esters obtained by the processes of the present invention.
In another preferred embodiment of the present invention, the processes are performed in the presence of 10 a catalyst, more preferably in the presence of a non-
recyclable catalyst. Even more preferably, the trans-
esterification is performed in the presence of a basic catalyst. Suitable basic catalysts include inorganic and organic bases, selected from NaOH, KOH, NaOCH3, and 15 mixtures thereof. More preferably, the catalyst is NaOCH3.
The catalyst may be used in an inert solvent such as an inorganic solvent, organic solvent or combination thereof.
Non-limiting examples of suitable solvents to be used in the processes of the present invention include substituted 20 and unsubstituted hydrocarbons, such as C-C1s hydrocarbons.
Preferably, the solvent is selected from hexane; heptane; octane; toluene; halocarbons, such as CBr4, CCl4, CHCl3, CH2Cl2; and mixtures thereof.
Typically, the catalyst is present in a catalytic 25 amount, that is, less than stochiometric quantity based on the fatty ester. By being able to utilize only catalytic amounts of catalyst, it is possible to prepare the desired wax esters at a relatively low costs and thus render the process more attractive from an economic point of view.
30 Preferably, the volume inside the reaction vessel is flooded with an inert gas, e.g. nitrogen and/or argon prior to letting in any starting materials of any of the claimed processes. The processes of the present invention may optionally 35 be performed in the presence of an inert solvent. Suitable solvents to be used in the processes of the present invention include any organic solvent or inorganic solvent
or mixtures thereof, which do not react with any of the reactants, namely with the fatty ester or with the fatty alcohol or with the wax esters or with the catalyst, if present. Non-limiting examples of suitable solvents to be 5 used in the processes of the present invention include substituted and unsubstituted hydrocarbons, such as C1-C5 hydrocarbons. Preferably, the solvent is selected from hexane; heptane; octane; toluene; halocarbons, such as CBr4, CCl4, CHCl3, CH2Cl2; and mixtures thereof.
10 In a preferred embodiment of the present invention, the reaction is performed at a pressure below about 0.1 atm, the ratio of the fatty esters to the fatty alcohols ranges from about 1.05:1 to about 1:1.05, the reaction is performed at a temperature below about 105 C, the reaction 15 is performed in the presence of a catalyst, the reaction is performed in the presence of an inert solvent or any combination thereof.
The process of the present invention may be effected in any suitable manner and may comprise either a batch or 20 continuous type operation. For example, when a batch type operation is used, a quantity of the reactants, namely the fatty ester and the fatty alcohol set forth hereinbefore in greater detail, are placed in an appropriate reaction vessel which may comprise a flask. In a preferred 25 embodiment of the present invention, the catalyst and/or any other additional component is added. Optionally, alternatively or in addition, the catalyst may be admixed with one or both of the reactants and the resulting mixture charged thereto into the reaction vessel. The pressure is 30 then adjusted by activating the vacuum pump and by adjusting the desired pressure controlled by any suitable pressure controlling device. The temperature at which the reaction is effected may be controlled by external means, that is either cooling means or conversely heating means.
35 The reaction is allowed to proceed for a predetermined period of time which may range from about 0.5 hours to about 24 hours or more in duration. This residence time
being dependent upon the various parameters of the reaction including pressure, temperature and type of reactants employed. Upon completion of the desired residence time, heating or cooling is discontinued and the apparatus and 5 contents thereof are allowed to return to room temperature.
The reaction mixture is then recovered and subjected to conventional means of separation as described below in more greater detail.
It is also contemplated within the scope of the 10 present invention that the process in which a fatty ester is treated with a fatty alcohol may be effected in a continuous manner of operation. When such a type of operation is employed, the starting materials comprising the fatty ester and the fatty alcohol are continuously 15 charged to a reaction zone which is maintained at the proper operation condition of pressure and optionally of temperature. In addition, the catalyst may be also charged to the reactor through a separate line, or if so desired, may be admixed with one or both of the reactants and the 20 resulting mixture charged thereto in a single stream.
Alternatively, the catalyst may be added to one of the reactants and the mixture charged through one line, the other reactant being charged through another line. Upon completion of the desired reaction time, the reactor 25 effluent is continuously withdrawn and subjected to conventional means of separation whereby the desired product is separated and recovered as described in greater detail below.
Additional Processing steps 30 Depending on the desired purity level of the wax esters products from the reaction of the present invention, further processing steps may be desired. The additional processing steps useful herein include one or more steps in which the intermediate or final or raw products are washed, 35 neutralized, separated and/or purified from impurities and/or side products and/or starting materials or any combination thereof.
Preferably, the catalysts are neutralized before refurbishing the reaction liquor and before isolating the desired wax ester. The basic catalyst is preferably neutralized with an acidic (pH of from about 6.5 to about 5 1) medium, preferably strongly acidic (pH of from about 3.0 to about 1) medium, in order to completely neutralize a strong basic catalyst. Preferably, an aqueous solution of the acidic, preferably strongly acidic medium is applied to the reaction mixture. Examples include H2SO4, HNO3, and HC1.
10 The washing step may be performed by adding either pure water or an aqueous solution of an inorganic salt, e.g. an about 10% wt. solution of sodium chloride, calcium chloride, and/or magnesium sulfate to the reaction mixture.
Often due to the hydrophobic nature of the wax esters 15 products of the present invention, a two phase solution will result after the washing step. These two phases should be separated from each other, wherein the desired wax ester is usually dissolved in the organic phase, and wherein the aqueous phase can usually be discarded. The solvent, if 20 present, is removed from the retained organic phase by any method applicable, e.g., vacuum distillation, and/or evaporation under reduced pressure with or without added heat. Finally, the desired wax esters product will be obtained as raw product. If desirable, the raw product can 25 be further purified by vacuum distillation, and/or re-
crystallization or any other method as known in the art.
Furthermore, if a colorless product is desired the resulting wax ester may be either bleached with active carbon and/or reacted with bleaching earths or any other 30 method known in the art.
Examples
The following non-limiting examples are illustrative of the present invention. Percentages are by weight unless otherwise specified.
For the purpose of the present invention, the reaction vessel can be any suitable one as known by the person skilled in the art. This includes reaction vessels made from glass ware as well as stainless steel reactors. The 5 reduced pressure inside the reaction vessel is constituted by any conventional means as known by the skilled person.
Non-limiting examples include mechanical vacuum pumps such as rotary vane pumps from Edwards, UK, e.g. Edwards RV12, and membrane pumps from IMLVAC, Germany, e.g. IMLVAC MPC 10 052Z. The reduced pressure inside the reaction vessel is measured by any conventional means as known by the skilled person. Non-limiting examples include a field mounted
pressure indicating controller with a stainless steel Bourbon tube. Furthermore, a Jordan Valve Mark 65 Vacuum 15 Regulator has been used for pressure control. The pressure indicating controller and the vacuum regulator are located in a position between the reactor and the vacuum pump. The pressure controller indicates the pressure for the entire process above the liquid phase in the reactor, including 20 the reactor headspace, the condenser and the receiver.
Example I
A reactor, which is a 12 liter flask equipped with thermometer, stirrer, heating mantle, overhead condenser, and receiver with dry ice trap is connected to a vacuum 25 pump. The stirrer is turned on and the flask is charged with 4114 grams (11.75 gram moles) of C22 methyl ester, 3147 grams (11.6 gram moles) of Cue fatty alcohol, and 29.05 grams (0.54 gram moles) of sodium methylate. The latter ingredient is added as a 25 solution in methanol for ease 30 of handling. The reactor is heated to a temperature of 100 C and the pressure is slowly reduced to 5 mm Hg over a period of four hours. The methanol is constantly removed from the reaction mixture to drive the reaction to completion while the reaction product remains in the 35 reactor.
After ventilating to atmospheric pressure, the reaction mixture is neutralized with 23.3 grams (0.20 gram
moles) of 85% phosphoric acid. 1800 grams of deionized water with 18 grams of sodium chloride present are then added to the reactor and are mixed for five minutes at a temperature of 85 C. Then the stirrer is turned off and the 5 water phase is settled and decanted. A total of 1866 grams of water is collected with a pH of 8.0. The wax ester left in the reactor is dried at a temperature of 75 C and a pressure of 5 mm Hg for a period of 30 minutes. 6583 grams of product is collected with a purity of 91% wax ester and 10 a moisture content of less than 0.1%.
Example II
A C24 wax ester is prepared using a procedure similar to that in Example 1. The product purity is 86% wax ester.
In order to reduce odor originating from residual levels of 15 C12 methyl ester and Cry fatty alcohol, the product is processed in a 2" short path continuous evaporator with internal condenser (Pope Scientific). The evaporator conditions are a pressure of 3 mm Hg and a jacket temperature of 180 C. The internal condenser uses 20 C 20 cooling water. Using a dropping funnel, 200 grams of material is processed in the evaporator over a period of two hours. The final residue out of the evaporator has a purity of 98% wax ester and a much reduced odor impression.
The distillate from the evaporator is a blend of C24 25 wax ester, C12 methyl ester, and C12 fatty alcohol and has a very sharp odor.

Claims (13)

Claims
1. A process for the preparation of wax esters comprising the reaction step of: 5 trans-esterifying C2-C60 fatty esters with C-C30 fatty alcohols wherein the reaction step is performed at a pressure below atmospheric pressure.
2. A process according to Claim 1, wherein the reaction 10 step is performed at a pressure below 0.5 atm, more preferably at a pressure below 0.2 atm, and most preferably at a pressure below 0.1 atm.
3. A process according to any of the preceding claims, wherein the reaction step is performed in the presence 15 of a catalyst, preferably in the presence of a non recyclable catalyst and even more preferably in the presence of a basic catalyst.
4. A process according to any of the preceding claims, wherein the reaction step is performed in the presence 20 of an inert solvent.
5. A process according any of the preceding claims, wherein the reaction step is performed at a temperature below 105 C, preferably at a temperature below 100 C, and more preferably at a temperature 25 between 60 C and 100 C.
6. A process according any of the preceding claims, wherein the ratio of the fatty esters to the fatty alcohols ranges from 10:1 to 1:10, preferably from 5:1 to 1:5, more preferably from 2:1 to 1:2, even more 30 preferably from 1.2:1 to 1:1.2, and most preferably from 1.05:1 to 1:1. 05.
7. A process according any of the preceding claims, wherein the fatty alcohols are selected from the group consisting of Car to C30 saturated or unsaturated, 35 linear, branched or cyclic fatty alcohols of natural or synthetic origin, and mixtures thereof; preferably from CIO to C22 saturated or unsaturated, linear,
branched or cyclic, substituted or unsubstituted fatty alcohols of natural or synthetic origin, and mixtures thereof; and most preferably from C2 to Cl8 saturated or unsaturated, linear, branched or cyclic, 5 substituted or unsubstituted fatty alcohols of natural or synthetic origin, and mixtures thereof.
8. A process according any of the preceding claims, wherein the fatty esters are selected from the group consisting of C2 to C60 saturated or unsaturated, 10 linear, branched or cyclic fatty esters of natural or synthetic origin, and mixtures thereof; preferably from the group consisting of CIO to C22 saturated or unsaturated, linear, branched or cyclic fatty esters of natural or synthetic origin; and mixtures thereof; 15 and more preferably from the group consisting of C:2 to C:8 saturated or unsaturated, linear, branched or cyclic fatty esters of natural or synthetic origin; and mixtures thereof.
9. A process according any of the preceding claims, 20 wherein the process to obtain the final wax esters comprises one or more additional processing steps selected from the group consisting of: steps in which the intermediate product or final product or raw product are washed, neutralized, separated and/or 25 purified from impurities and/or side products and/or starting materials or any combination thereof.
10. A process according any of the preceding claims, wherein the reaction step is performed at a pressure below 0.1 atm, wherein the ratio of the fatty esters 30 to the fatty alcohols ranges from 1.05:1 to 1:1.05, and wherein the reaction step is performed at a temperature below 105 C.
11. A process for the preparation of wax esters substantially as described herein with reference to 35 examples I and II.
12. A method of using the wax esters obtained by the process according to any of the preceding claims in
any home care application and/or fabric care application and/or cosmetics application and/or personal care application and/or pharmaceutical application and/or confectionery application.
5
13. The use of the wax esters obtained by the process according to any of the preceding claims in any home care application and/or fabric care application and/or cosmetics application and/or personal care application and/or pharmaceutical application and/or confectionery 10 application.
GB0329456A 2002-12-19 2003-12-19 Preparation of wax esters by transesterifying esters with alcohols below atmospheric pressure Withdrawn GB2396611A (en)

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4002667A (en) * 1974-03-26 1977-01-11 Imperial Chemical Industries Limited Bis-(2-hydroxyethyl)-terephthalate
JPS57185235A (en) * 1981-05-07 1982-11-15 Mitsui Toatsu Chem Inc Preparation of neopentyl polyol ester from fatty acid
JPS62185051A (en) * 1986-02-10 1987-08-13 Mitsui Toatsu Chem Inc Production of acrylic acid or methacrylic acid higher alkyl ester
JPH0648988A (en) * 1992-07-29 1994-02-22 Dainippon Ink & Chem Inc Production of tetrakis(3-@(3754/24)3,5-dialkyl-4--hydroxyphenyl) propionyloxyalkyl) methane
WO1999057092A1 (en) * 1998-05-02 1999-11-11 Cognis Deutschland Gmbh Method for producing polyolesters
JP2001271090A (en) * 2000-03-24 2001-10-02 Sumitomo Chem Co Ltd Method for producing fatty acid ester and fuel containing fatty acid ester

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4002667A (en) * 1974-03-26 1977-01-11 Imperial Chemical Industries Limited Bis-(2-hydroxyethyl)-terephthalate
JPS57185235A (en) * 1981-05-07 1982-11-15 Mitsui Toatsu Chem Inc Preparation of neopentyl polyol ester from fatty acid
JPS62185051A (en) * 1986-02-10 1987-08-13 Mitsui Toatsu Chem Inc Production of acrylic acid or methacrylic acid higher alkyl ester
JPH0648988A (en) * 1992-07-29 1994-02-22 Dainippon Ink & Chem Inc Production of tetrakis(3-@(3754/24)3,5-dialkyl-4--hydroxyphenyl) propionyloxyalkyl) methane
WO1999057092A1 (en) * 1998-05-02 1999-11-11 Cognis Deutschland Gmbh Method for producing polyolesters
JP2001271090A (en) * 2000-03-24 2001-10-02 Sumitomo Chem Co Ltd Method for producing fatty acid ester and fuel containing fatty acid ester

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