GB2081266A - Production of sucrose-fatty acid esters - Google Patents
Production of sucrose-fatty acid esters Download PDFInfo
- Publication number
- GB2081266A GB2081266A GB8123178A GB8123178A GB2081266A GB 2081266 A GB2081266 A GB 2081266A GB 8123178 A GB8123178 A GB 8123178A GB 8123178 A GB8123178 A GB 8123178A GB 2081266 A GB2081266 A GB 2081266A
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- United Kingdom
- Prior art keywords
- fatty acid
- sucrose
- soap
- weight
- molten mixture
- 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.)
- Granted
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- 239000000194 fatty acid Substances 0.000 title claims abstract description 52
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 229930006000 Sucrose Natural products 0.000 claims abstract description 51
- 239000005720 sucrose Substances 0.000 claims abstract description 51
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims abstract description 46
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 41
- 229930195729 fatty acid Natural products 0.000 claims abstract description 41
- 239000000344 soap Substances 0.000 claims abstract description 41
- -1 fatty acid ester Chemical class 0.000 claims abstract description 34
- 239000000203 mixture Substances 0.000 claims abstract description 32
- 238000005809 transesterification reaction Methods 0.000 claims abstract description 17
- 239000002904 solvent Substances 0.000 claims abstract description 15
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 13
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- 229910052751 metal Inorganic materials 0.000 claims abstract description 12
- 239000002184 metal Substances 0.000 claims abstract description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 9
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 9
- 239000003054 catalyst Substances 0.000 claims abstract description 8
- 238000002844 melting Methods 0.000 claims abstract description 5
- 230000008018 melting Effects 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 38
- 239000003513 alkali Substances 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 235000021588 free fatty acids Nutrition 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 150000001242 acetic acid derivatives Chemical class 0.000 claims 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
- 150000001342 alkaline earth metals Chemical class 0.000 claims 1
- 150000004703 alkoxides Chemical class 0.000 claims 1
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 150000003841 chloride salts Chemical class 0.000 claims 1
- 150000001860 citric acid derivatives Chemical class 0.000 claims 1
- 150000004679 hydroxides Chemical group 0.000 claims 1
- 150000003893 lactate salts Chemical class 0.000 claims 1
- 150000002823 nitrates Chemical class 0.000 claims 1
- 235000021317 phosphate Nutrition 0.000 claims 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 23
- 238000010438 heat treatment Methods 0.000 abstract description 3
- HPEUJPJOZXNMSJ-UHFFFAOYSA-N Methyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC HPEUJPJOZXNMSJ-UHFFFAOYSA-N 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- CAMHHLOGFDZBBG-UHFFFAOYSA-N epoxidized methyl oleate Natural products CCCCCCCCC1OC1CCCCCCCC(=O)OC CAMHHLOGFDZBBG-UHFFFAOYSA-N 0.000 description 9
- 235000002639 sodium chloride Nutrition 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000004530 micro-emulsion Substances 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 238000007664 blowing Methods 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 125000005313 fatty acid group Chemical group 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000001103 potassium chloride Substances 0.000 description 2
- 235000011164 potassium chloride Nutrition 0.000 description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- 235000011132 calcium sulphate Nutrition 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000011362 coarse particle Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000007970 homogeneous dispersion Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 235000011147 magnesium chloride Nutrition 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000001508 potassium citrate Substances 0.000 description 1
- 229960002635 potassium citrate Drugs 0.000 description 1
- QEEAPRPFLLJWCF-UHFFFAOYSA-K potassium citrate (anhydrous) Chemical compound [K+].[K+].[K+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QEEAPRPFLLJWCF-UHFFFAOYSA-K 0.000 description 1
- 235000011082 potassium citrates Nutrition 0.000 description 1
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- PHZLMBHDXVLRIX-UHFFFAOYSA-M potassium lactate Chemical compound [K+].CC(O)C([O-])=O PHZLMBHDXVLRIX-UHFFFAOYSA-M 0.000 description 1
- 239000001521 potassium lactate Substances 0.000 description 1
- 235000011085 potassium lactate Nutrition 0.000 description 1
- 229960001304 potassium lactate Drugs 0.000 description 1
- 239000004323 potassium nitrate Substances 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- LWIHDJKSTIGBAC-UHFFFAOYSA-K potassium phosphate Substances [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
- 229940114930 potassium stearate Drugs 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- ANBFRLKBEIFNQU-UHFFFAOYSA-M potassium;octadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCCCC([O-])=O ANBFRLKBEIFNQU-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229960004249 sodium acetate Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 229940074404 sodium succinate Drugs 0.000 description 1
- ZDQYSKICYIVCPN-UHFFFAOYSA-L sodium succinate (anhydrous) Chemical compound [Na+].[Na+].[O-]C(=O)CCC([O-])=O ZDQYSKICYIVCPN-UHFFFAOYSA-L 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 229940114926 stearate Drugs 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
- C07H13/06—Fatty acids
-
- Y—GENERAL 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
Abstract
Sucrose-fatty acid esters are by melting an alkali metal soap of a fatty acid free of water or other solvent, adding sucrose and a fatty acid ester to the molten soap to give a homogeneous molten mixture of these reaction components, and heating the molten mixture at a temperature from 125 DEG C to 165 DEG C under vacuum. Conventional basic transesterification catalysts and/or inert metal salts may be added to the molten mixture.
Description
SPECIFICATION
Production of sucrose-fatty acid esters
This invention relates to a method for producing sucrose-fatty acid esters by the transesterification of fatty acid esters with sucrose.
Various methods are known for producing sucrose-fatty acid esters. They may be classified into the following three principal types.
In the solvent process, a fatty acid ester is transesterified with sucrose in a common solvent for the fatty acid ester and sucrose such as dimethylformamide or dimethylsulfoxide in the presence of a basic transesterification catalyst.
The reaction may be carried out even at a relatively lower temperature, for example, at about 90"C. This process suffers from certain disadvantages that the solvent used is slightly toxic and, therefore, must be completely removed after the reaction. This is possible in practice only with great difficulty.
In the second process generally known as "microemulsion process", a fatty acid ester is dispersed in a solution of sucrose in a solvent such as propylene glycol or water with the aid of an emulsifier such as soap to form a microemulsion, and then the solvent is removed from the emulsion. The reaction is carried out in the absence of solvent and the reaction product does not contain any solvent. Great difficulty is also present in this process for removing the solvent while maintaining the microemulsion state.
In the third process, sucrose is directly reacted with a fatty acid ester by heating their mixture.
This process is known as "direct process". Since sucrose and fatty acid esters do not have sufficient affinity to each other, the success of this direct process depends on how they are well contacted in the reaction system.
In Japanese Patent Publication 41171/74, sucrose is reacted with a fatty acid ester in a molten state at a temperature of 160--1900C in the presence of alkali-free soap as a transesterification catalyst. This process suffers from the disadvantage of requiring the use of alkali-free soap which is difficult to make, as well as the use of a high reaction temperature close to the decomposition temperature of sucrose. Thus, degradation of sucrose unavoidably may occur to a certain extent during the reaction to give less pure products.
Japanese Laid Open Patent Publication 96518/75 describes a method comprising the steps of adding an excess of fatty acid ester to a methanolic solution containing alkali metal hydroxide and sucrose, partially saponifying the fatty acid ester to form the corresponding soap, removing the methanol and then reacting the remaining fatty acid ester with sucrose. Also,
Japanese Laid Open Patent Publication 39621/76 describes a method comprising the steps of preparing a molten mixture of alkali metal carbonate and sucrose with the aid of a small amount of water, and reacting a fatty acid ester with the mixture. These two methods are disadvantageous in requiring the removal of solvent which often causes phase separation to occur.
Japanese Laid Open Patent Publication 65704/76 proposes a heterogeneous reaction between sucrose and a fatty acid ester at atmospheric pressure in which no solvent is used and sucrose is not molten. Obviously this heterogeneous reaction is less advantageous than homogeneous reaction in many respects such as reaction velocity, reaction time and the like.
In accordance with one aspect of the present invention there is provided a method for producing sucrose-fatty acid esters which comprises:
melting an alkali metal soap of a fatty acid which is free of water or other solvents,
adding and mixing thereto sucrose and a fatty acid ester to give a homogeneous molten mixture, and
reacting said molten mixture at a temperature from 1 250C to 1 650C under vacuum to produce sucrose-fatty acid esters.
The homogeneous molten mixture of reaction components may contain a conventional basic transesterification catalyst preferably in the form of free alkali containing soap and a metal salt which is inert to the transesterification reaction.
The addition of inert metal salt may increase the reaction rate in terms of decrease in the amount of unreacted fatty acid ester.
DETAILED DESCRIPTION OF THE INVENTION
The present invention has its basis on our discovery that when solid sucrose and a fatty acid ester are added to a sufficient amount of a molten anhydrous alkali soap of a fatty acid, a homogeneous molten mixture of these components may be obtained. When the sucrose and fatty acid ester are added to the molten anhydrous soap and the temperature is raised gradually, a endothermic phenomenon may be seen at about 1 250C to give a visually homogeneous molten mixture of these three components. This means that sucrose may be transformed into liquid phase at a temperature substantially lower than its melting point. The amount of anhydrous soap required for melting sucrose in this manner is at least 10% by weight, preferably from 1 5 to 30% by weight based on the total weight of the molten mixture.The formation of homogeneous phase from these components is substantially retarded by the presence of only small amount of water, ethanol or other solvents.
Once the homogeneous phase is formed, the transesterification of fatty acid ester with sucrose may occur at a temperature from about 1 250C to 1 650C under a relatively weak vacuum to give
desired sucrose ester of fatty acid in a high yield.
Any commercially available solid sucrose of any grade and size may be used in the method of the present invention. Preferably coarse particles are preliminarily divided into finer particles of less than 70 mesh particle size.
The preferred fatty acid esters for the method of this invention have 8 to 22 carbon atoms in the fatty acid moiety and 1 to 4 carbon atoms in the monohydric alcohol moiety. The fatty acid may be of straight or branched chain and of saturated or unsaturated type. Mixed fatty acid esters may also be used.
Anhydrous alkali soaps of fatty acid are derived from an alkali and a fatty acid of the abovementioned type. Any conventional alkali conventionally used for making soap such as potassium carbonate, sodium carbonate,
potassium hydroxide, sodium hydroxide, sodium methoxide, potassium ethoxide and the like may be used. Potassium carbonate and sodium carbonate are preferable as they do not produce any by-product such as water or methanol which must be subsequently removed. The amount of alkali may be an equivalent or preferably slightly excess relative to the amount of fatty acid so that the resulting soap contains an amount of free alkali which catalyzes the transesterification reaction.
Alternatively, the above-mentioned alkali may be added separately to the reaction system in an amount from 1 to 10%, preferably from 3 to 7% by weight based on the weight of sucrose. The addition of alkali may be made simultaneously with or after the addition of sucrose and fatty acid ester to the molten soap.
The molten soap must be anhydrous and free of any solvent. To this end the molten soap is preferably heated at a temperature above 1 O00C, preferably from 120 to 1 4O0C under a reduced pressure from 50 to 200 mmHg for 20 to 30 minutes. The addition of sucrose and fatty acid ester to the molten soap may be made in any order or simultaneously preferably while
maintaining the temperature of molten soap at a temperature above 1 250C. Experiments have shown that excessive sucrose and fatty acid ester relative to the molten soap may adversely affect the yield of desired sucrose-fatty acid ester.
Experiments have also shown that the amount of
molten soap should occupy at least 10%, preferably 15 to 30% by weight of the entire molten mixture.
Thus, sucrose may be reacted with the fatty acid ester in a homogeneous phase in a simple
manner at a temperature substantially lower than the decomposition point of sucrose. The transesterification reaction may be carried out at a temperature from 1 250C to 1 650C under vacuum
less than 200 mmHg. The reaction time varies with the nature of starting materials, reaction temperature and the like, and generally less than 5
hours.
The resultant product contains soap, unreacted
sucrose and fatty acid ester in addition to sucrosefatty acid ester. These impurities may be removed
by conventional techniques well-known in the art
to give purified sucrose-fatty acid ester preferably having a purity higher than 95%. The
recovered sucrose and soap may be re-used in the
next batch of reaction. The remaining soap may be
conveniently converted to free fatty acid and recovered in this form. This free fatty acid is used for the preparation of soap used for another batch of the method.
In order to promote the reaction rate, a metal salt which is inert to the transesterification may be added to the molten mixture of soap, sucrose and fatty acid ester Examples of inert salts include sodium chloride, potassium chloride, calcium chloride, magnesium chloride, sodium sulfate, potassium sulfate, calcium sulfate, potassium nitrate, sodium nitrate, mono-potassium phosphate, di-potassium phosphate, sodium acetate, potassium lactate, sodium succinate, potassium citrate and the like. The amount of inert metal salt is at least 3%, preferably from 5 to 20% by weight based on the weight of entire reaction mixture. Addition of inert metal salt may be made to the molten soap separately or simultaneously with sucrose and fatty acid ester.
The addition of inert metal salt gives an additional advantage of facilitating the re-use of recovered sucrose in cycle. Normally recovered sucrose contains an amount of minerals which must be removed before the re-use thereof in conventional transesterification reactions.
The addition of inert metal salt according to the invention eliminates the need for removal of such minerals from recovered sucrose for reusing as starting material in another batch of transesterification.
The method of the present invention has certain important advantages over the prior art methods.
A stable, homogeneous molten mixture may be easily made in a simple manner from soap, sucrose and fatty acid, and the transesterification may be carried out in a homogenous phase at a temperature substantially lower than the decomposing temperature of sucrose under weak vacuum.
Alkali metal soap of fatty acid used for making homogeneous molten mixture in accordance with the present invention may be easily prepared using an excess of alkali relative to the fatty acid and may also be used as transesterification catalyst.
The method of the present invention can eliminate bubble forming which is often experienced in the prior art methods when alkali soap is added to the reaction system. The following non-limiting Examples 1 and 2 will further illustrate the present invention.
Comparative Examples 1-3 are not according to the invention all percentages therein are by weight.
EXAMPLE 1
18.7g of stearic acid in a 500ml flask having stirring means, thermometer and vacuum means was heated to 1 250C. 9.2g of potassium carbonate powder was added with stirring and allowed to react with stearic acid. The resultant soap was then stirred at 1 300C at 100mmHg for 20 minutes to remove water. To the molten soap were added 70g of sucrose powder and 52.4g of methyl stearate with stirring. The mixture was stirred at 1 400C at 100mmHg for 3 hours. The reaction mixture contained 1.2% of methyl stearate. From this the reaction rate was calculated as 96.8%.The content of sucrose stearates in the reaction mixture was found to be 43.5%, and the composition thereof was found to be 48% monostearate, 35% distearate, and 17% tristearate.
COMPARATIVE EXAMPLE 1
To the same flask used in Example 1 were added 61.6g of sucrose, 46.0g of methyl stearate, 30g of alkali-free sodium stearate and 40ml of propylene glycol. The content of flask was dissolved by heating at 1 350C. Then vacuum (initially 1 00mmHg) was applied and propylene glycol was distilled off with causion to excessive bubbling at a final temperature and vacuum of 1 6O0C and 4mmHg, respectively. Then 5g of potassium carbonate was added and the mixture was reacted at the same temperature and vacuum for 3 hours. The resulting dark product contained 3.8% of methyl stearate. The reaction rate was calculated as 87.0%.
COMPARATIVE EXAMPLE 2
To a 500ml flask having stirring means, thermometer and nitrogen gas blowing means were added 52g of sucrose powder and 45g of methyl stearate. The content of flask was heated at 1 500C to give a molten mass which was visually homogeneous. 1 0g of sodium carbonate was added and the mixture was reacted at 1 500C while blowing nitrogen gas for 4 hours. The resulting dark brown product contained 5.6% of methyl stearate. The reaction rate was calculated as 86%.
COMPARATIVE EXAMPLE 3
To the same flask used in Example 1 were added 70.1g of sucrose, 21.59 of sodium stearate, 52.4g of methyl stearate and 35g of water. The content of flask was heated to 1 350C to obtain a transparent, homogeneous dispersion. Then water was distilled off under vacuum and the mixture was reacted at 1 550C at 25mmHg for 3 hours.
The resulting product contained 2.4% of methyl stearate and 42.6% of sucrose stearates. The reaction rate was calculated as 93.6%.
EXAMPLE 2
1 53g of potassium stearate was melted in the same flask used in Example 1 at 1350 C. To this were added a mixture of 350g of powdered sucrose and 1 00g of potassium chloride, 220g of methly stearate, and 1 Og of potassium carbonate, successively. The mixture was reacted at 1 4O0C at SmmHg for 3 hours with stirring. The resulting light brown product contained 0.8% of methyl stearate and 48.2% of sucrose stearates. The composition of sucrose stearates was found to be 47.5% monostearate, 36.2% distearate, and 16.3% tristearate. The reaction rate was
calculated as 97.1%.
Claims (16)
1. A method for producing sucrose-fatty acid esters which comprises:
melting an alkali metal soap of a fatty acid which is free of water or other solvents,
adding and mixing thereto sucrose and a fatty acid ester to give a homogeneous molten mixture, and
reacting said molten mixture at a temperature from 1 250C to 1 650C under vacuum to produce sucrose-fatty acid esters.
2. The method of Claim 1, whereinsaid fatty acid ester is an alkyl ester having 8 to 22 carbon atoms in the fatty acid moiety and 1 to 4 carbon atoms in the alkyl moiety.
3. The method of Claim 1 or Claim 2, wherein the alkali metal soap contains 8 to 22 carbon atoms in the fatty acid moiety.
4. The method of any one of Claims 1-3, wherein the alkali metal soap comprises at least 10% by weight of the molten mixture.
5. The method of Claim 4, wherein the alkali metal soap comprises 1 5 to 30% by weight of the molten mixture.
6. The method of any one of Claims 1-5, wherein the alkali metal soap contains free alkali.
7. The method of any one of Claims 1-6, wherein 1 to 10%, by weight based on the weight of sucrose, of a basic transesterification catalyst is also added to the molten mixture.
8. The method of Claim 7 wherein the catalyst comprises 3 to 7% by weight on the same basis.
9. The method of Claim 7 or Claim 8, wherein said basic transesterification catalyst is selected from hydroxides, carbonate and lower alkoxides of potassium and sodium.
10. The method of any one of Claims 1-9 wherein a metal salt which is inert to the transesterification reaction is also added to the molten mixture.
11. The method of Claim 10, wherein said inert metal salt is at least 3% by weight of the entire mixture.
12. The method of Claim 11 wherein said inert metal salt is 5 to 20% by weight of the entire mixture.
13. The method of Claim 11 or Claim 12, wherein said inert metal salt is selected chlorides, sulfates, nitrates, phosphates, acetates, lactates, succinate and citrates of alkali metal and alkaline earth metals.
14. The method of any one of Claims 1 to 1 3 further including the steps of recovering unreacted sucrose and soap from the reaction mixture and re-using the recovered sucrose and soap in another batch of the method.
1 5. The method of Claim 14, wherein said soap is recovered as free fatty acid, and the recovered free fatty acid is used for preparing said soap used in another batch of the method.
16. The method of Claim 1 substantially as herein described in Example 1 or Example 2.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55105637A JPS6026399B2 (en) | 1980-07-31 | 1980-07-31 | Method for producing sucrose fatty acid ester |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2081266A true GB2081266A (en) | 1982-02-17 |
| GB2081266B GB2081266B (en) | 1984-03-28 |
Family
ID=14412966
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8123178A Expired GB2081266B (en) | 1980-07-31 | 1981-07-28 | Production of sucrose-fatty acid esters |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS6026399B2 (en) |
| AU (1) | AU544202B2 (en) |
| BR (1) | BR8104942A (en) |
| FR (1) | FR2487838A1 (en) |
| GB (1) | GB2081266B (en) |
| IT (1) | IT1138104B (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0132941A1 (en) * | 1983-06-23 | 1985-02-13 | The Procter & Gamble Company | Synthesis of higher polyol fatty acid polyesters using carbonate catalysts |
| GB2161806A (en) * | 1984-06-29 | 1986-01-22 | Dai Ichi Kogyo Seiyaku Co Ltd | Production of sucrose fatty acid polyester |
| EP0190779A1 (en) * | 1985-01-24 | 1986-08-13 | Coöperatieve Vereniging Suiker Unie U.A. | Method for the preparation of esters of a non-reducing sugar or sugar alcohol and one or more fatty acids |
| EP0275939A2 (en) * | 1987-01-17 | 1988-07-27 | Mitsubishi Kasei Corporation | Process for preparing sucrose fatty acid esters |
| EP0322971A2 (en) * | 1987-12-29 | 1989-07-05 | Unilever N.V. | Process for the synthesis of polyol fatty acid polyesters |
| US5006648A (en) * | 1986-07-23 | 1991-04-09 | Van Den Bergh Foods Co., Division Of Conopco Inc. | Process for preparing partial polyol fatty acid esters |
| EP0434117A2 (en) * | 1989-12-21 | 1991-06-26 | Unilever N.V. | Process for refining soapcontaining crude polyol fatty-acid polyester reaction products |
| US8329894B2 (en) | 2006-04-28 | 2012-12-11 | Sebus Limited | Process for the production of esters of sugars and sugar derivatives |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2548185B1 (en) * | 1983-06-29 | 1986-03-21 | Agrifurane Sa | PROCESS FOR PREPARING FURANIC ESTERS BY TRANSESTERIFICATION REACTION |
| JPS6150448A (en) * | 1984-08-18 | 1986-03-12 | Fuji Facom Corp | Data transmission system |
| JPS61189289A (en) * | 1985-02-15 | 1986-08-22 | Dai Ichi Kogyo Seiyaku Co Ltd | Production of sucrose fatty acid ester having high substitution degree |
| ES2014018B3 (en) * | 1986-02-19 | 1990-06-16 | Unilever Nv | ESTERS OF FATTY ACIDS OF SUGARS AND SUGARS-ALCOHOLS. |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3714144A (en) * | 1969-05-29 | 1973-01-30 | Us Agriculture | Process for the production of sucrose esters of fatty acids |
| JPS4941171A (en) * | 1972-07-10 | 1974-04-17 | ||
| JPS5096518A (en) * | 1973-12-28 | 1975-07-31 | ||
| US3963699A (en) * | 1974-01-10 | 1976-06-15 | The Procter & Gamble Company | Synthesis of higher polyol fatty acid polyesters |
| JPS50142507A (en) * | 1974-05-02 | 1975-11-17 | ||
| JPS5114485A (en) * | 1974-07-25 | 1976-02-04 | Kataoka Kikai Seisakusho Kk | HOSOSHIMAKITSUKECHORYOKUSEIGYOSOCHI |
| JPS5114486A (en) * | 1974-07-27 | 1976-02-04 | Fujimori Kogyo Co | Hosoho oyobi sonosochi |
| JPS5114488A (en) * | 1974-07-27 | 1976-02-04 | Towa Seiki Kk | Hosoyotaino umuo senbetsusuru sochi |
-
1980
- 1980-07-31 JP JP55105637A patent/JPS6026399B2/en not_active Expired
-
1981
- 1981-07-22 AU AU73301/81A patent/AU544202B2/en not_active Ceased
- 1981-07-24 IT IT23142/81A patent/IT1138104B/en active
- 1981-07-28 GB GB8123178A patent/GB2081266B/en not_active Expired
- 1981-07-30 BR BR8104942A patent/BR8104942A/en not_active IP Right Cessation
- 1981-07-31 FR FR8114909A patent/FR2487838A1/en active Granted
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0132941A1 (en) * | 1983-06-23 | 1985-02-13 | The Procter & Gamble Company | Synthesis of higher polyol fatty acid polyesters using carbonate catalysts |
| GB2161806A (en) * | 1984-06-29 | 1986-01-22 | Dai Ichi Kogyo Seiyaku Co Ltd | Production of sucrose fatty acid polyester |
| EP0190779A1 (en) * | 1985-01-24 | 1986-08-13 | Coöperatieve Vereniging Suiker Unie U.A. | Method for the preparation of esters of a non-reducing sugar or sugar alcohol and one or more fatty acids |
| US4778881A (en) * | 1985-01-24 | 1988-10-18 | Cooperatieve Vereniging Suiker Unie U.A. | Method for the preparation of esters of a non-reducing sugar and one or more fatty acids |
| US5071975A (en) * | 1986-07-23 | 1991-12-10 | Van Den Bergh Foods Co., Division Of Conopco Inc. | Process for preparing polyol fatty acid polyesters |
| US5006648A (en) * | 1986-07-23 | 1991-04-09 | Van Den Bergh Foods Co., Division Of Conopco Inc. | Process for preparing partial polyol fatty acid esters |
| EP0275939A3 (en) * | 1987-01-17 | 1990-06-13 | Mitsubishi Kasei Corporation | Process for preparing sucrose fatty acid esters |
| EP0275939A2 (en) * | 1987-01-17 | 1988-07-27 | Mitsubishi Kasei Corporation | Process for preparing sucrose fatty acid esters |
| EP0322971A2 (en) * | 1987-12-29 | 1989-07-05 | Unilever N.V. | Process for the synthesis of polyol fatty acid polyesters |
| EP0322971A3 (en) * | 1987-12-29 | 1991-07-31 | Unilever N.V. | Process for the synthesis of polyol fatty acid polyesters |
| EP0434117A2 (en) * | 1989-12-21 | 1991-06-26 | Unilever N.V. | Process for refining soapcontaining crude polyol fatty-acid polyester reaction products |
| EP0434117A3 (en) * | 1989-12-21 | 1991-11-06 | Unilever Nv | Process for refining soapcontaining crude polyol fatty-acid polyester reaction products |
| US8329894B2 (en) | 2006-04-28 | 2012-12-11 | Sebus Limited | Process for the production of esters of sugars and sugar derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2487838B1 (en) | 1983-12-02 |
| FR2487838A1 (en) | 1982-02-05 |
| JPS5731694A (en) | 1982-02-20 |
| BR8104942A (en) | 1982-04-20 |
| AU544202B2 (en) | 1985-05-23 |
| IT8123142A0 (en) | 1981-07-24 |
| JPS6026399B2 (en) | 1985-06-24 |
| IT1138104B (en) | 1986-09-17 |
| GB2081266B (en) | 1984-03-28 |
| AU7330181A (en) | 1982-02-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19960728 |