JPH09168395A - Production of saccharide fatty acid ester - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject compound high in surface activity in excellent productivity by reacting a saccharide such as a monosaccharide, a disaccharide, an ether compound of a monosaccharide and a monohydric alcohol and a sugar- alcohol with a fatty acid in the presence of a specific ketone-based solvent and a lipase. SOLUTION: At least one saccharide such as a 5-7C monosaccharide, a disaccharide composed of a hexose, an ether compound of the 5-7C monosaccharide and a monohydric alcohol, a 4-6C sugar-alcohol or these condensate through dehydration is esterified with at least one fatty acid based compound such as a 6-22C saturated and unsaturated fatty acid or an esterified substance of the fatty acid and a 1-4C lower alcohol in the presence of at least one ketone-based solvent (e.g. cyclohexanone) having >=100 deg.C boiling point as an organic solvent by using a lipase to give the objective saccharide fatty acid ester high in surface activity, useful as a cleaning agent composition strong in cleaning power in high productivity.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a method for producing a sugar fatty acid ester utilizing an enzymatic reaction.

[0002]

It is known that a detergent composition having a strong detergency can be obtained by blending a sugar fatty acid ester having a high surface activity. As a method of synthesizing this sugar fatty acid ester, a method of synthesizing a sugar and a fatty acid or a lower alkyl ester of the fatty acid using an alkali as a catalyst is known (Japanese Patent Publication No. 35-13102). . However, in this method, when an alkali is used as a catalyst, a large amount of di- or tri-fatty acid ester having low surface-active ability is by-produced. A reaction in the system is required. Therefore, in this method, the productivity does not reach a practical level in consideration of recovery and recycling of products and unreacted raw materials, and further, the reaction product is markedly colored due to the synthetic reaction at high temperature. There was a problem.
On the other hand, a method of reacting a saccharide with a fatty acid or a lower alkyl ester of the fatty acid using a lipase as a catalyst to synthesize a sugar fatty acid ester has been reported (Bjoerking et al., CHEM.SOC., COMMUN., 1989). Year) . This method includes:
Although the di- or tri-fatty acid ester is less by-produced and the synthetic reaction is carried out at a low temperature, there is an extremely excellent advantage that the product is less colored, but the reaction rate is slow. In a study to overcome this drawback, in order to obtain a practical reaction rate in the lipase-catalyzed sugar fatty acid ester synthesis method, in order to obtain a practical reaction rate, a sugar with a strong hydrophilic property and a fatty acid with a strong hydrophobic property or a lower alkyl ester thereof is used. It became clear that an organic solvent that dissolves both is necessary. The applicant of the present invention, as disclosed in Japanese Patent Application Laid-Open Nos. 4-16196, 5-112592 and 5-176783, has used various organic solvents to carry out this synthetic reaction rate. However, research was conducted to further improve the productivity of sugar fatty acid monoesters.

[0003]

PROBLEM TO BE SOLVED BY THE INVENTION A process for producing a sugar fatty acid monoester utilizing an enzymatic reaction, which produces little di- or tri-fatty acid ester as a by-product and has high production efficiency, is provided.

[0004]

In order to solve the above-mentioned problems, the organic solvent of the present invention is
It is necessary to satisfy the conditions that the enzymatic activity of lipase is not impaired and that both highly hydrophilic saccharides and highly hydrophobic fatty acids are sufficiently dissolved. In particular, the solvent with high lipase activity is a water-insoluble organic solvent, and conversely, in a water-soluble organic solvent that dissolves sugars well, the water in the enzyme is deprived of the enzyme activity and the enzyme activity is lost. Change the molecular structure of the active site (A-05991, Na
tional AOCS Meeting, May 19, 1987). As a result of the research conducted by the present inventors, it was found that an organic solvent containing at least one ketone solvent having a boiling point of 100 ° C. or higher satisfies the above conditions (1) and (2).

Therefore, the present invention has 5 to 7 carbon atoms.
Monosaccharides, disaccharides consisting of hexoses, 5 carbon atoms
An ether compound of 7 monosaccharides and a monohydric alcohol,
At least one saccharide selected from sugar alcohols having 4 to 6 carbon atoms and dehydration condensation products thereof, saturated and unsaturated fatty acids having 6 to 22 carbon atoms, and the fatty acids and 1 to 4 carbon atoms A method for producing a sugar fatty acid ester, which comprises esterifying at least one fatty acid-based compound selected from esterified products with individual low alcohols with lipase in the presence of an organic solvent, wherein the organic solvent is
Provided is a method for producing a sugar fatty acid ester, which comprises at least one ketone solvent having a boiling point of 100 ° C or higher. Next, the present invention will be described in detail.

The saccharide used in the present invention has 5 to 7 carbon atoms.
Monosaccharides, disaccharides consisting of hexoses, 5 carbon atoms
An ether compound of 7 monosaccharides and a monohydric alcohol,
It is selected from sugar alcohols having 4 to 6 carbon atoms and dehydration condensation products thereof, and these are used alone or in combination of two or more kinds. Specific examples of these include arabinose, ribose, xylose, lyxose, xylulose, ribulose, and 2-deoxyribose as monosaccharides having 5 carbon atoms. Is glucose, galactose,
Fructose, mannose, sorbose, talose, 2
-Deoxyglucose, 6-deoxygalactose, 6
-Deoxymannose, 2-deoxygalactose and the like, and monosaccharides having 7 carbon atoms include alloheptulose, sedoheptulose, mannoheptulose and glucoheptulose. Examples of disaccharides composed of hexose include maltose, sucrose and sophorose, and examples of sugar alcohols include erythritol, ribitol, xylitol, allitol, sorbitol, mannitol and galactitols. Moreover, in the ether compound of a monosaccharide having 5 to 7 carbon atoms and a monohydric alcohol, the monohydric alcohol may be a linear or branched chain, or a saturated or unsaturated carbon chain. The number of atoms is preferably 1 to 12, particularly 1 to 4. As specific examples, methyl alcohol, ethyl alcohol, propyl alcohol, butyl alcohol and the like are preferable.

Further, the bonding position of the saccharide and the monohydric alcohol is not particularly limited and may be any position. In these alkyl glucosides, the configurations of the hemiacetal hydroxyl groups after the alkyl substitution may be α and β respectively, or α and β may be mixed at an arbitrary ratio. Further, in the present invention, the dehydrated condensate of the above-mentioned monosaccharide, disaccharide, etherified product and sugar alcohol can also be used as a saccharide for the synthesis of sugar fatty acid ester. Incidentally, in the present invention, the number of carbon atoms having no substituent is 5 to 7
Monosaccharides, disaccharides consisting of hexose, and sugar alcohols having 4 to 6 carbon atoms and sugars selected from these condensates are mixed and used, whereby sugar fatty acids are efficiently produced at a ratio according to the usage ratio. A mixture of ester and sugar ether fatty acid ester can be synthesized simultaneously.

The fatty acid compound used in the present invention is at least one selected from saturated and unsaturated fatty acids having 6 to 22 carbon atoms, and esterified products of the fatty acid and a low alcohol having 1 to 4 carbon atoms. Is a compound of. Examples of the saturated and unsaturated fatty acids include caproic acid, sorbic acid, capric acid, lauric acid, myristic acid, palmitoleic acid, palmitic acid, stearic acid, isostearic acid, oleic acid, linoleic acid, linolenic acid, pentadecanoic acid. , Eicosanoic acid, docosanoic acid, docosenoic acid, arachidonic acid, ricinoleic acid, dihydroxystearic acid and the like. Further, in the present invention, as the esterified product,
An esterified product of the above fatty acid and a lower alcohol having 1 to 4 carbon atoms is used. The lower alcohol includes methanol, ethanol, propanol, and butanol. To give a specific example of the esterified product,
Methyl caproate, ethyl caproate, methyl caprate, ethyl caprate, methyl laurate, ethyl laurate, propyl laurate, methyl myristate, ethyl myristate, propyl myristate, methyl palmitate, ethyl palmitate, palmitate Propyl, methyl stearate, ethyl stearate, propyl stearate, methyl oleate, ethyl oleate, propyl oleate, methyl linoleate, ethyl linoleate, propyl linoleate, methyl linolenate, ethyl linolenate, propyl linolenate , Methyl eicosanoate, methyl arachidonic acid, methyl docosanoate, and methyl docosenoate.

The amount of the fatty acid compound used is usually 0.5 to 10 mol, preferably 0.5 to 3 mol, based on 1 mol of the saccharide. The reason for limiting the amount used in this way is that if the amount is less than 0.5 mol, the synthetic reaction rate of the sugar fatty acid ester becomes remarkably slow, and if it is more than 10 mol, separation and recovery from the reaction product becomes complicated. Because it will be. In the present invention, an enzyme that esterifies the saccharide and the fatty acid compound is used and reacted in the presence of a specific organic solvent described later. This enzyme is a lipase and means an enzyme group belonging to hydrolases. Examples of this lipase include porcine pancreas-derived lipase, candida-derived yeast lipase, and microbial cell-derived lipase. Bacteria that produce this lipase include Aspergillus spp, Mucor spp, Pseudomonas spp, Rhizopus spp, Penicillium spp, and Chromobacterium spp. Lipase may be used. In addition, the lipase of the present invention is used in a form contained in a purified or crude enzyme composition, or a microbial cell producing an enzyme having an esterolytic activity (treated microbial cell, quiescent or quiescent bacterium). It is also possible to use the dried product of the body directly.

In the esterification reaction with the lipase of the present invention, since the lipase reacts with the saccharide after forming an intermediate bond with the fatty acid compound, the monoester is preferred even if the fatty acid compound is used in excess. By-products of fatty acid polysubstituted compounds such as diesters and triesters, which are synthesized synthetically and have low interfacial performance, can be kept low. Further, the enzyme composition containing the lipase may be used in a state of being dispersed in the reaction solution, but by using it as an immobilized enzyme, heat resistance is improved, and recovery / recycling from the reaction solution is used. Can be done efficiently. Examples of carriers for immobilizing the enzyme composition include activated carbon, porous glass, acid clay, kaolinite, alumina, silica gel, bentonite, hydroxyapatite, calcium phosphate, inorganic substances such as metal oxides, starch and gluten. There are synthetic polymers such as natural polymer, polyethylene, polypropylene, phenol formalin resin, acrylic resin, anion exchange resin and cation exchange resin. Of these carriers, porous synthetic polymer carriers are preferred. For example, it is porous polyethylene, porous polypropylene, porous phenol formalin resin, porous acrylic resin, or the like.

When the lipase is immobilized on the carrier, usually 0.2 to 5 parts of the purified enzyme composition are added to 1 g of the carrier.
It is fixed to be 00 mg, preferably 20 to 200 mg. In this case, the enzyme composition preferably contains 30 to 80% lipase. The amount of saccharide used when the immobilized enzyme is used is not particularly limited. On the other hand, assuming a reaction by a batch reactor, 0.01 to 1 part of the enzyme composition containing lipase is added to 1 part by weight of sugar as a raw material.
It is preferred to use parts by weight, preferably 0.05 to 0.5 parts by weight. If the amount of enzyme is small, it takes time to complete the reaction and the production efficiency becomes low. On the contrary, if the amount of enzyme is large, uniform stirring of the reaction solution may be hindered.

The organic solvent used as the reaction solvent in the present invention is a ketone solvent having a boiling point of 100 ° C. or higher. In addition,
In the present invention, since the organic solvent is used for ester synthesis or transesterification, it is necessary to be separable from water or a lower alcohol which is a by-product. In addition, the solvent recovered during the reaction and from the reaction mixture must be purified and recycled for practical use. Therefore, in order to accurately separate it by rectification, adsorption operation, etc., the boiling point of the solvent is 100 ° C or more. Is preferred. Further, the ketone-based solvent used in the present invention can be used in a mixture with an aliphatic hydrocarbon, an aromatic hydrocarbon or the like, which has a small decrease in the enzyme activity of lipase and has a high compatibility with the ketone-based solvent. An example of this ketone solvent is 2
-Pentanone, 3-pentanone, methyl isobutyl ketone, diisobutyl ketone, mesityl oxide, hexanone, 2-methylcyclohexanone, 3-methylcyclohexanone, 4-methylcyclohexanone, 2-heptanone, 3-heptanone, 4-heptanone, 2-octanone, 3 -Octanone, 2-nonanone, 5-nonanone, acetophenone, diisobutyl ketone, acetylacetone, acetonylacetone, phorone, isophorone and the like, and these ketone solvents can be used alone or in combination of two or more. The amount of the ketone solvent used can be appropriately selected depending on the type of solvent, the carbon chain length of the starting fatty acid or its ester, and the reaction temperature. Usually, the amount of the ketone solvent is 0.1 to 30 parts by weight, particularly 0.5 to 20 parts by weight, based on 1 part by weight of the saccharide.

The temperature of the synthesis reaction is determined in consideration of the optimum temperature of the lipase used, but it is usually 30 to 100.
C, preferably 40 to 90C. Furthermore, when the sugar fatty acid ester is produced according to the present invention, any method such as a batch reaction method, a semi-batch reaction method, and a packed column reaction method may be used. The batch reaction method refers to a method in which a saccharide, a fatty acid compound, a lipase, and a solvent are introduced into a reaction tank, and the reaction is carried out at a constant temperature, pressure, and stirring conditions. The semi-batch reaction system is a method in which a lipase and a solvent are introduced into a reaction tank, and a predetermined temperature, pressure, and stirring conditions are set to prepare for the reaction to proceed, and then either a saccharide or a fatty acid compound and both Is continuously supplied to proceed the reaction. The packed column reaction system is a method in which a column reactor filled with an immobilized enzyme is allowed to proceed with a reaction by passing a solution prepared by dissolving a saccharide and a fatty acid compound in a predetermined solvent. Since the method of the present invention is an ester synthesis or transesterification reaction, water or a lower alcohol is by-produced, and an equilibrium reaction occurs depending on the amount of the by-product. Therefore, in order to smoothly proceed the synthesis reaction, it is preferable to remove these by-products from the reaction system. As a method of removing the by-products from the reaction system, a method of depressurizing the inside of the reaction tank and evaporating and discharging the reaction system, a method of removing the by-products from the reaction system by using zeolite, molecular sieve, PV membrane, etc. By combining these methods with the above-mentioned reactor, the synthetic reaction can be efficiently carried out.

[0014]

Next, the present invention will be described in detail with reference to examples and comparative examples. In addition, this invention is not limited to a following example. Reference Example First, in order to compare the properties of the ketone solvent used in the present invention with conventional organic solvents, the solubility of sugars and fatty acid compounds and the activity of the immobilized enzyme after immersion in the solvent were measured. . First, 0.2 g of the immobilized enzyme was immersed in 4 g of a solvent in a 30 ml Erlenmeyer flask at 70 ° C. for 24 hours, and then allowed to stand at room temperature for separation to remove only the solvent and t-Bu.
Washed with OH. After washing, the immobilized enzyme was added to 7 ml of a t-BuOH solution containing glycerin as a substrate and methyl lauric acid ester, and reacted at 50 ° C. for 15 minutes. The product glyceryl laurate monoester was quantified by gas chromatography.
No decrease in enzyme activity was observed by the washing operation with t-BuOH at room temperature. At the same time, the same enzyme reaction was carried out with an enzyme that was not immersed in a solvent as a blank, and the activity after immersion in the solvent was shown as a percentage. The results of this experiment are shown in Table 1 below.

[0015]

TABLE 1 TABLE 1 ───────────────────────────────── Shikurohe Jimechiruhoru Jimechirusu quinone Muamido sulfoxide solvent after immersion of the active (%) 92.7 0 0 Solubility C ₁₀ fatty acid methyl ∞ ∞ ∞ ∞ (wt%) ester C ₁₀ fatty acid ∞ ∞ ∞ methyl glucoside 0.5 21 46

As described above, in the method of synthesizing a sugar fatty acid ester by reacting a saccharide and a fatty acid compound with an enzyme such as lipase as a catalyst, a practical reaction rate is obtained by an enzymatic reaction. In order to do so, two components, a saccharide and a fatty acid compound, must be sufficiently present in the vicinity of the active site on the surface of the solid-phase enzyme that is the reaction site. For this reason, the present invention requires a solvent that dissolves both a highly hydrophilic saccharide and a highly hydrophobic fatty acid compound, and at the same time does not inhibit the enzymatic reaction at the active site of the enzyme. As shown in Table 1, the ketone solvent used in the present invention allows the enzymatic reaction to proceed without impairing the activity of lipase, has high solubility of the above-mentioned two components, and can efficiently remove the reaction product, and the lipase It can be seen that the solvent does not affect the enzyme active site.

Example 1 A four-necked round bottom equipped with a stirrer, a thermometer, a mercury manometer and a vacuum exhaust tube was charged with 194 g of cyclohexanone, and 23.7 g of caprylic acid methyl ester and methyl glucoside (MG) were added with stirring. ) 19.4g
1.9 g of immobilized lipase enzyme was added. Subsequently, the low boiling point components such as methanol by-produced by the reaction and water brought in from the raw materials are distilled off from the vacuum exhaust pipe via a cold trap, and the temperature of the reaction system is raised to 70 ° C. The reaction was carried out for 6 hours while maintaining the vacuum degree at 40 mmHg. After the reaction was completed, the reaction solution was cooled to 20 ° C., the pressure in the reaction system was returned to normal pressure, and the reaction solution was filtered to separate the immobilized enzyme and the reaction solution. The reaction solution is acetylated by a conventional method,
Analysis by gas chromatography (GC) was performed to measure the composition (area ratio) of the reaction product excluding the methyl solvent. On the other hand, the immobilized enzyme was washed with butanol and then the enzyme activity was measured by the method used in Reference Example. GC analysis composition Unreacted MG: 4.8 Gucoside caprylic acid monoester: 69.5 Gucoside caprylic acid diester: 2.7 Unreacted ester, unreacted fatty acid: 23.0 Enzyme activity after reaction (%): 98

Example 2 Using the same apparatus as in Example 1, 194 g of cyclohexanone was charged, and while stirring, 27.9 g of capric acid methyl ester and methyl glucoside were added.
19.4 g and 1.0 g of immobilized lipase enzyme were added. While distilling off low boiling point components such as methanol by-produced by the reaction and water brought from the raw material from the vacuum exhaust pipe via the cold trap, the temperature of the reaction system is raised to 60 ° C. and the pressure of the reaction system is 40 mmHg. While maintaining, the reaction was carried out for 6 hours. After the reaction was completed, the reaction solution was cooled to 20 ° C., the pressure of the reaction system was returned to normal pressure, and then the reaction solution was filtered to separate the immobilized enzyme and the reaction solution. The reaction solution was acetylated by a conventional method and analyzed by gas chromatography to measure the composition (area ratio) of the reaction product excluding the methyl solvent. On the other hand, the immobilized enzyme used in the reaction was washed with butanol, and then the enzyme activity was measured by the method of Reference Example. GC analysis composition Unreacted MG: 4.6 Glucoside capric acid monoester: 69.4 Gucocide capric acid diester: 1.9 Unreacted ester, unreacted fatty acid: 24.1 Enzyme activity after reaction (%): 98

[Example 3] Using the same apparatus as in Example 1, 194 g of 2-heptanone was charged, and while stirring, 27.9 g of capric acid methyl ester and 19.4 g of methyl glucoside.
, And 1.9 g of immobilized lipase enzyme were added. While distilling off low boiling point components such as methanol by-produced by the synthesis reaction and water brought in from the raw material through the vacuum exhaust pipe via a cold trap, the temperature of the reaction system is raised to 60 ° C. The reaction was carried out for 6 hours while maintaining the pressure at 40 mmHg. After the reaction was completed, the reaction solution was cooled to 20 ° C., the pressure of the reaction system was returned to normal pressure, and then the reaction solution was filtered to separate the immobilized enzyme and the reaction solution. The reaction solution was acetylated by a conventional method and analyzed by gas chromatography to measure the composition (area ratio) of the reaction product excluding the methyl solvent. On the other hand, the immobilized enzyme used in the reaction was washed with butanol, and then the enzyme activity was measured by the method of Reference Example. GC analysis composition Unreacted MG: 4.6 Guccoside capric acid monoester: 65.9 Gucocide capric acid diester: 3.7 Unreacted ester, unreacted fatty acid: 25.8 Enzyme activity after reaction (%): 98

[Example 4] Using the same apparatus as in Example 1, 194 g of diisobutyl ketone was charged and stirred,
Stearic acid methyl ester 59.6g, methyl glucoside
19.4 g and 1.9 g of immobilized lipase enzyme were added. While evaporating low-boiling components such as methanol by-produced by the synthesis reaction and water brought in from the raw material through the vacuum exhaust pipe and the cold trap, the temperature of the reaction system was raised to 70 ° C and the pressure of the reaction system was set to a vacuum degree of 30 mmHg. The reaction was carried out for 6 hours while maintaining After the reaction was completed, the reaction solution was cooled to 20 ° C., the pressure of the reaction system was returned to normal pressure, and then the reaction solution was filtered to separate the immobilized enzyme and the reaction solution. The reaction solution was acetylated by a conventional method and analyzed by gas chromatography to measure the composition (area ratio) of the reaction product excluding the methyl solvent. After the immobilized enzyme was washed with butanol, the enzyme activity was measured by the method of Reference Example. GC analysis composition Unreacted MG: 2.5 Guccoside stearic acid monoester: 2.34 Gucocide stearic acid diester: 4.7 Unreacted ester, unreacted fatty acid: 40.5 Enzyme activity after reaction (%): 98

[Example 5] Using the same apparatus as in Example 1, 194 g of cyclohexanone was charged, and 44.7 g of methyl stearate and ethyl glucoside 2 were added while stirring.
0.6 g and 2.0 g of immobilized lipase enzyme were added. While evaporating low-boiling components such as methanol by-produced by the synthesis reaction and water brought in from the raw material through the vacuum exhaust pipe and the cold trap, the temperature of the reaction system was raised to 70 ° C and the pressure of the reaction system was set to a vacuum degree of 30 mmHg. The reaction was carried out for 6 hours while maintaining Then, the reaction solution was cooled to 20 ° C., the pressure in the reaction system was returned to normal pressure, and then the reaction solution was filtered to separate the immobilized enzyme and the reaction solution. The reaction solution was acetylated by a conventional method and analyzed by gas chromatography to measure the composition (area ratio) of the reaction product excluding the methyl solvent. After the immobilized enzyme was washed with butanol, the enzyme activity was measured by the method of Reference Example. GC analysis composition Unreacted ethyl glucoside: 4.0 Guccoside stearic acid monoester: 64.9 Gucocide stearic acid diester: 3.0 Unreacted ester, unreacted fatty acid: 28.1 Enzyme activity after reaction (%): 96

Comparative Example 1 Using the same apparatus as in Example 1, 139.5 g of capric acid methyl ester, 97 g of methyl glucoside and 9.7 g of immobilized lipase enzyme were added. While evaporating low-boiling components such as methanol by-produced by the synthesis reaction and water brought in from the raw material through the vacuum exhaust pipe and a cold trap, the temperature of the reaction system is raised to 70 ° C. and the pressure of the reaction system is 40 mmHg in vacuum degree. The reaction was carried out for 24 hours while maintaining After the reaction was completed, the reaction solution was cooled to 40 ° C., the pressure of the reaction system was returned to normal pressure, and the reaction solution was filtered to separate the immobilized enzyme and the reaction solution. The reaction solution was acetylated by a conventional method and analyzed by gas chromatography to measure the composition (area ratio) of the methyl reaction product. On the other hand, the immobilized enzyme was washed with butanol, and then the enzyme activity was measured by the method of Reference Example. GC analysis composition Unreacted MG: 7.5 Gukoside capric acid monoester: 43.2 Gukoside capric acid diester: 32.9 Unreacted ester, unreacted fatty acid: 16.3 Enzyme activity after reaction (%): 25

Comparative Example 2 Using the same apparatus as in Example 1, 194 g of methyl ethyl ketone (boiling point 80 ° C.) was charged, and while stirring, 23.7 g of capric acid methyl ester, 19.4 g of methyl glucoside, and immobilized lipase enzyme 1.9. g was added. While distilling off low boiling point components such as methanol by-produced by the reaction and water brought from the raw material from the vacuum exhaust pipe via a cold trap, the temperature was raised to 65 ° C.
While maintaining the pressure of the reaction system at a vacuum degree of 40 mmHg, the reaction was carried out for 6 hours. After the reaction was completed, the reaction solution was cooled to 20 ° C., the pressure of the reaction system was returned to normal pressure, and then the reaction solution was filtered to separate the immobilized enzyme and the reaction solution. The reaction solution was acetylated by a conventional method and analyzed by gas chromatography to measure the composition (area ratio) of the reaction product excluding the methyl solvent. on the other hand,
After the immobilized enzyme was washed with butanol, the enzyme activity was measured by the method of Reference Example. GC analysis composition Unreacted MG: 17.0 Gukoside capric acid monoester: 41.3 Gukoside capric acid diester: 9.4 Unreacted ester, unreacted fatty acid: 32.3 Enzyme activity after reaction (%): 51

Comparative Example 3 Using the same apparatus as in Example 1, 194 g of n-decane (boiling point 174 ° C.) was charged, and while stirring, 23.7 g of capric acid methyl ester, 19.4 g of methyl glucoside, and immobilized lipase enzyme. 1.9g was added. While evaporating low-boiling components such as water by-produced from the synthetic reaction and water brought from the raw materials through a vacuum exhaust pipe and a cold trap, the temperature of the reaction system is raised to 65 ° C. and the pressure of the reaction system is 40 mmHg in vacuum degree. The reaction was carried out for 6 hours while maintaining
After the reaction was completed, the reaction solution was cooled to 20 ° C., the pressure of the reaction system was returned to normal pressure, and then the reaction solution was filtered to separate the immobilized enzyme and the reaction solution. The reaction solution was acetylated by a conventional method and analyzed by gas chromatography to measure the composition (area ratio) of the reaction product excluding the methyl solvent. On the other hand, the immobilized enzyme was washed with butanol, and then the enzyme activity was measured by the method of Reference Example. GC analysis composition Unreacted MG: 23.3 Gukoside capric acid monoester: 31.2 Gukoside capric acid diester: 6.2 Unreacted ester, unreacted fatty acid: 39.3 Enzyme activity after reaction (%): 92

 ─────────────────────────────────────────────────── ─── Continued Front Page (72) Inventor Hiroshi Nakamura 1-3-7 Main Office, Sumida-ku, Tokyo Inside Lion Corporation

Claims (1)

[Claims] 1. A monosaccharide having 5 to 7 carbon atoms, a disaccharide composed of hexose, an ether compound of a monosaccharide having 5 to 7 carbon atoms and a monohydric alcohol, and a sugar having 4 to 6 carbon atoms. From alcohols and at least one saccharide selected from dehydration condensation products thereof, saturated and unsaturated fatty acids having 6 to 22 carbon atoms, and esterified products of the fatty acids and lower alcohols having 1 to 4 carbon atoms A method for producing a sugar fatty acid ester, wherein at least one selected fatty acid compound is esterified with a lipase in the presence of an organic solvent, wherein the organic solvent is at least a ketone solvent having a boiling point of 100 ° C or higher. A method for producing a sugar fatty acid ester, which comprises one kind.