JPH09224694A - Production of sugar fatty acid ester - Google Patents

Abstract

PROBLEM TO BE SOLVED: To produce a sugar fatty acid ester in a continuous and effective manner. SOLUTION: This method for producing a sugar fatty acid ester comprises (a) a process in which a saccharide (A) and a fatty acid compound (B) are fed into the first reaction system where lipase-immobilized particles are suspended, the sugar fatty acid ester is synthesized and a byproduct consisting of water and alcohol formed by the synthesis of the sugar fatty acid ester is removed at 30-100 deg.C and <=100Torr in the degree of vacuum, (b) a process in which the lipase-immobilized particles are removed from the reaction mixture of the process (a), the liquid portion of the reaction mixture is fed into the second reaction system where lipase-immobilized particles are suspended and a byproduct formed in the synthesis of the sugar fatty acid ester is removed at 30-100 deg.C and <=100Torr in the degree of vacuum, and (c) a process in which the lipase-immobilized particles are removed from the reaction mixture of the process (b), the liquid portion of the reaction mixture is fed into the third reaction system where lipase-immobilized particles are suspended and a byproduct formed in the synthesis of the sugar fatty acid ester is removed at 30-100 deg.C and <=100Torr in the degree of vacuum.

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. More specifically, the present invention relates to a method for producing a sugar fatty acid ester in which esterification is continuously performed in a plurality of steps.

[0002]

When a sugar fatty acid ester is industrially produced using lipase, in order to improve heat resistance and activity and facilitate recovery, lipase is used as an immobilized enzyme, and the immobilized lipase is used in a batch system, or Used in a continuous reaction system. When sugar fatty acid ester is synthesized using lipase, the synthesis reaction of sugar fatty acid ester reaches equilibrium due to increase of by-products such as water and alcohol, and the synthesis reaction is stopped (Carl Miller et al., National AOCS Meeting.
In New Orleans, May 19, 1987), the by-product is removed and the synthetic reaction proceeds while avoiding the reaction equilibrium.
However, in batch reaction, charging of raw materials while stirring, temperature rise to reaction temperature, progress of ester reaction, recovery of sugar fatty acid ester, cooling, recovery / separation of immobilized lipase, etc. in one reaction tank Since this step is carried out, the lipase is easily released from the carrier, the recovery yield is lowered, and the enzyme activity is also easily lowered. Further, in the batch system using a stirring tank, the gas phase portion on the surface of the reaction solution can be decompressed to easily remove dehydration and dealcohol, but at the initial stage of the reaction with many reaction substrates, water and alcohol are used. Since the amount of by-products such as is particularly large, and then the amount of by-products decreases,
The removal conditions such as pressure and temperature must be set according to the reaction stage, which is complicated. On the other hand, as a continuous reaction system, a system using a fixed bed in which a temperature controller, a pre-column for water content adjustment, etc., and an immobilized lipase packed tower are connected is known. There is a drawback that the contact time is insufficient and the reaction does not proceed sufficiently. As a method for solving this drawback, a loop reaction method in which the reaction solution that has passed through the fixed bed of immobilized lipase is dehydrated while aeration with dry nitrogen and the fixed bed is circulated to proceed the reaction in two stages Is known (Koji Kosugi, "Oil Chemistry", Vol. 44, No. 10, 869-874, 1995).
Year). However, this loop reaction system has a drawback in that it is difficult to perform the dehydration and dealcoholization necessary in the circulation line.

[0003]

The present invention provides a method for efficiently producing sugar fatty acid ester by solving the drawbacks of the conventional methods for producing sugar fatty acid ester by the batch method and the continuous method.

[0004]

[Means for Solving the Problems] As a result of research for solving the above problems, a saccharide and a fatty acid compound are reacted in a continuous process of a system in which lipase-immobilized particles are suspended, and at the same time, a by-product is reacted in a predetermined amount. It was found that removal under the conditions can prevent equilibrium in the synthetic reaction and efficiently produce sugar fatty acid ester. The present invention has been completed based on this finding. Therefore, the present invention provides the following method for producing an ester of sugar fatty acid. (A) a monosaccharide having 5 to 7 carbon atoms, a disaccharide consisting of hexose, an ether compound of a monosaccharide having 5 to 7 carbon atoms and a monohydric alcohol, a sugar alcohol having 4 to 6 carbon atoms, and At least one saccharide selected from these dehydration condensates, and (B) a saturated or unsaturated fatty acid having 6 to 22 carbon atoms, and an esterified product of the fatty acid and a lower alcohol having 1 to 4 carbon atoms At least 1 selected from
A method for producing a sugar fatty acid ester, which comprises esterifying a fatty acid compound of a species with a lipase in the presence of an organic solvent, comprising the following steps (a) to (d):

(A) First in which lipase-immobilized particles are suspended
The sugar system (A) and the fatty acid compound (B) are supplied to the reaction system to synthesize a sugar fatty acid ester, and a by-product containing water and alcohol produced by the synthesis of the sugar fatty acid ester is treated at a temperature of 30 to 100 ° C. A step of removing the lipase-immobilized particles from the reaction solution of step (a), and removing the reaction solution from the reaction solution of step (a) in which the lipase-immobilized particles are suspended.
By-products containing water and alcohol, which are supplied to the reaction system and are produced in the synthesis of sugar fatty acid ester, are heated at a temperature of 30 to 100.
A step of removing the lipase-immobilized particles from the reaction solution of the step (b), the step of removing the lipase-immobilized particles from the reaction solution of the third step in which the lipase-immobilized particles are suspended.
By-products containing water and alcohol, which are supplied to the reaction system and are produced in the synthesis of sugar fatty acid ester, are heated at a temperature of 30 to 100.
And a degree of vacuum of 100 torr or less; and (d) a step of separating the lipase-immobilized particles from the reaction solution of step (c) and recovering the sugar fatty acid ester from the reaction solution. In the above production method, the step (c) is performed at least twice by replacing the third reaction system in which the lipase-immobilized particles are suspended with a new reaction system, thereby improving the efficiency of sugar fatty acid ester production. Can be planned. Next, the present invention will be described in detail.

The saccharide (A) used in the present invention has 5 carbon atoms.
~ 7 monosaccharides, disaccharides composed of hexose, ether compounds of monosaccharides having 5 to 7 carbon atoms and monohydric alcohols, sugar alcohols having 4 to 6 carbon atoms and dehydration condensation products thereof At least one sugar. Specific examples of these include arabinose, ribose, xylose, lyxose, xylulose, ribulose, and 2-deoxyribose as monosaccharides having 5 carbon atoms. Is glucose,
There are 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, and mannohepts. Loose, glucoheptulose, etc. 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 preferably 1 to 6. To give a specific example,
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, a dehydrated condensate obtained from the monosaccharide, disaccharide, ether compound and sugar alcohol can be used as the saccharide. In the present invention, monosaccharides having no substituents and having 5 to 7 carbon atoms, disaccharides composed of hexose, and saccharides selected from sugar alcohols having 4 to 6 carbon atoms are mixed and used. Thus, the mixture of the sugar fatty acid ester and the sugar ether fatty acid ester can be efficiently synthesized at a ratio according to the use ratio thereof. The fatty acid compound used in the present invention is at least one kind selected from saturated and unsaturated fatty acids having 6 to 22 carbon atoms, and esterified products of the fatty acid and low alcohol having 1 to 4 carbon atoms. It is a compound.

Examples of the saturated and unsaturated fatty acids are:
Caproic acid, sorbic acid, capric acid, lauric acid, myristic acid, palmitoleic acid, palmitic acid, stearic acid, isostearic acid, oleic acid, linoleic acid,
Examples include linolenic acid, pentadecanoic acid, eicosanoic acid, docosanoic acid, docosenoic acid, arachidonic acid, ricinoleic acid, and dihydroxystearic acid. 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. Specific examples of the esterified product include methyl caproate, ethyl caproate, methyl caprate, ethyl caprate, methyl laurate, ethyl laurate, propyl laurate, methyl myristate, ethyl myristate, myristic acid. Propyl, methyl palmitate, ethyl palmitate,
Propyl palmitate, methyl stearate, ethyl stearate, propyl stearate, methyl oleate, ethyl oleate, propyl oleate, methyl linoleate, ethyl linoleate, propyl linoleate, methyl linolenate, ethyl linolenate, linolene Propyl acid, methyl eicosanoate, methyl arachidonic acid, methyl docosanoate, methyl docosenoate and the like.

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 it is lower than 0.5 mol, the synthesis reaction rate of sugar fatty acid ester will be slow, and if it is higher than 10 mol, separation and recovery from the reaction product will be complicated. Because. The solvent used in the present invention is a solvent that dissolves both a highly hydrophilic saccharide and a strongly hydrophobic fatty acid or a lower alkyl ester thereof, and does not inhibit the activity of lipase. The boiling point of this solvent is 100 ° C. or higher, especially 140 ° C.
~ 200 ° C is preferred. The reason why the boiling point of the solvent is 100 ° C. or higher is that
This is because the solvent must be stable in the reaction liquid phase. Examples of the solvent of the present invention include butyrolactone, picoline, cyclohexanone, 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, isophorone and other ketone solvents; tetrahydrothiophene-1,
1-dioxaside (sulfolane) and the like. In the present invention, these solvents are used alone or in combination of two or more kinds.

The amount of the solvent used can be appropriately selected depending on the type of the solvent, the carbon chain length of the starting fatty acid or its ester, and the reaction temperature. Usually, the amount of the solvent is 1 to 30 parts by weight, preferably 1 to 10 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 is usually 30 to 90 ° C, preferably 50 to 80 ° C. The enzyme used in the present invention is lipase, which means a group of enzymes 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 bacterial cell that produces an enzyme having an esterolytic activity (treated bacterial cell, dormant or resting bacterial cell). 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 of the fatty acid compound, the monoester is preferentially used 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, in the present invention, the enzyme composition containing the lipase is used as an immobilized enzyme. Examples of the carrier 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, natural polymers such as gluten, polyethylene, polypropylene, phenol formalin resin, acrylic resin ,
There are synthetic polymers such as anion exchange resins and cation exchange resins. Of these carriers, porous synthetic polymer carriers are preferred. For example, there are porous polyethylene, porous polypropylene, porous phenol formalin resin, porous acrylic resin and the like. When the lipase is immobilized on the carrier, the purified enzyme composition is usually immobilized on 1 g of the carrier in an amount of 0.2 to 500 mg, preferably 10 to 30 mg. In this case, the enzyme composition contains lipase 30-
80% is preferable.

The specific gravity of the lipase-immobilized particles used in the present invention is 1.1 to 2.0, preferably 1.2 to 1.5, and the average particle size is 100 to 1,000 μm, preferably 300.
It is suitable to set the thickness to 800 μm. Examples of commercially available immobilized enzymes of lipase include Novozym 435 (NO
VONORDISK company). This immobilized enzyme is obtained by immobilizing lipase on a macroporous anion exchange resin, has high enzyme activity and heat resistance, and is suitable for the present invention. The average particle size of the immobilized enzyme is about 400 mμ and the true specific gravity is 1.4, and the specific gravity of the reaction solution used for the synthesis of sugar fatty acid ester is usually 0.9 to 1.1, so that it can be rapidly gravity-precipitated. Settle and separate. In the present invention, the enzyme composition containing lipase is used in an amount of 0.01 to 1 part by weight, and particularly 0.05 to 0.5 part by weight, relative to 1 part by weight of the raw material sugar.
If the amount of enzyme is small, it takes time to complete the reaction and the production efficiency is not low. On the contrary, if the amount of enzyme is large, uniform stirring of the reaction solution may be disturbed. This enzyme composition is used as an index of the effective enzyme content, and is 5,000 per gram.
It has an enzyme activity of ˜15,000 PLU. PLU means the production rate (μmol / min.) Of propyl-lauric acid ester at 60 ° C. per gram of the enzyme composition.

The manufacturing method of the present invention has the following continuous steps. (a) The sugar (A) and the fatty acid compound (B) are supplied to the first reaction system in which the lipase-immobilized particles are suspended to synthesize a sugar fatty acid ester, and the sugar fatty acid ester is synthesized. By-products including water and alcohol are heated to a temperature of 30 to 100.
℃, preferably 50 ~ 80 ℃, vacuum 100 torr or less,
Preferably, the step of removing under the condition of 5 to 50 torr; (b) the lipase-immobilized particles are separated from the reaction solution of the step (a), and the reaction solution is used as a second suspension of the lipase-immobilized particles.
By-products containing water and alcohol, which are supplied to the reaction system and are produced in the synthesis of sugar fatty acid ester, are heated at a temperature of 30 to 100.
℃, preferably 50 ~ 80 ℃, vacuum 100 torr or less,
Preferably, the step of removing the lipase-immobilized particles under the condition of 5 to 50 torr; (c) the lipase-immobilized particles are separated from the reaction solution of step (b), and the reaction solution is suspended in the third step.
By-products containing water and alcohol, which are supplied to the reaction system and are produced in the synthesis of sugar fatty acid ester, are heated at a temperature of 30 to 100.
℃, preferably 50 ~ 80 ℃, vacuum 100 torr or less,
Preferably, it is a step of removing under conditions of 5 to 50 torr; and (d) a step of separating the lipase-immobilized particles from the reaction solution of step (c) and recovering the sugar fatty acid ester from the reaction solution.

In order to continuously overflow the reaction solution in each tank, it is preferable to keep the pressure in each tank constant with a pressure equalizing pipe or the like, but the overflow pipe is intermittently opened within the above pressure range. It is also possible to change the pressure of each tank by closing. Further, within the above temperature range, it is possible to change the reaction rate in order to control the reaction rate and to select the optimum conditions for separating by-produced water and alcohols. In the production method of the present invention, the synthesis reaction of sugar fatty acid ester is carried out while keeping the enzyme in the reactor and simultaneously removing the by-products lower alcohol and water out of the system. In steps (a) to (c) of the present invention, the suspended state of the immobilized lipase particles is maintained. By setting the suspension state, the reaction liquid on the surface of the immobilized lipase particles is constantly renewed, so that the esterification reaction can proceed rapidly and the undesirable diester can be prevented from increasing.
When stirring is performed to maintain the suspended state, the carrier that forms the immobilized lipase particles must be kept in a stirred state so as not to separate from the lipase. For example,
As a stirring state, stirring power of 0.2 to 1.5 KW / m ³ is required.

In the conventional multi-stage stirring tank, the immobilized lipase particles are washed away from the reaction tank due to the overflow of the reaction solution. Therefore, the immobilized lipase particles must be newly supplied so as to have a predetermined concentration. did not become. On the other hand, in the present invention, the separation device for immobilized lipase particles is used to prevent the immobilized lipase particles from flowing out when the reaction solution moves through each step. In order to prevent this outflow, a method of providing a wire mesh with openings smaller than the immobilized lipase particles at the liquid outlet (see FIG. 2),
There is a method in which an overflow weir is provided and the enzyme particles in the overflowed reaction solution are settled by gravity and then the reaction solution is allowed to flow to the next reactor (see FIG. 3). In the case of separation outside the reactor, there is a method in which a gravity settling tank is provided between the pipes connecting the reactors to separate the immobilized enzyme particles into a lower layer and return them to the original reactor. As a method for removing by-products generated in the esterification reaction from the reaction system, in addition to a method of evaporating the surface of the reaction solution under reduced pressure, zeolite, molecular sieve, PV membrane or the like is used, and water or a lower alcohol such as There is a method of removing by-products from the reaction system.

Next, a mode for carrying out the present invention and an apparatus used for carrying out the present invention will be described with reference to FIGS. FIG.
In the apparatus shown in FIG. 3, the reaction tank 8 is equipped with a stirrer, a jacket 13 and an overflow pipe 16, and the overflow pipe 16 is horizontally installed in the middle of the reaction tank 8. Reaction liquid outlet
A separation device for immobilized lipase particles is provided at a connection portion between 14 and the overflow pipe 16. This separation device
For example, as shown in FIG. 2, a wire mesh 17 attached to the end of the overflow pipe 16 and having a mesh size smaller than that of the immobilized lipase particles, and as shown in FIG. A gravity settling tube 18 is installed and the immobilized lipase particles settled by gravity are returned to the reaction tank 8.

In the embodiment of the present invention, first, each reaction tank 8
A suspension containing immobilized lipase particles and a solvent is prepared. Next, sugars contained in tanks 1, 2 and 3,
The fatty acid compound and the solvent are continuously supplied to the first reaction tank (first reaction system) by the pumps 5, 6 and 7. Sugar fatty acid ester is synthesized in the first reaction tank, and by-produced water and alcohol are distilled off. Further, the reaction liquid in an amount corresponding to the raw materials supplied at the same time overflows, and the immobilized lipase particles are separated and transferred to the second reaction tank (second reaction system). Further, synthesis of sugar fatty acid ester proceeds in the second reaction tank, water and alcohol produced as by-products are distilled off, and an amount of the reaction liquid corresponding to the supplied reaction liquid overflows,
The immobilized lipase particles are separated and transferred to the third reaction tank (third reaction system). Then, the reaction solution is moved from the third reaction tank to the reaction solution recovery tank 11, and the sugar fatty acid ester is recovered from the reaction solution by a conventional method. The ratio of the supplied sugars converted into sugar fatty acid ester is 10 to 60% in the first reaction tank, and the second
It is 20 to 80% in the reaction tank and 50 to 95% in the third reaction tank. In this embodiment, the temperature of the reaction system is adjusted by the jacket 13 provided on the side surface of each reaction tank, and the liquid surface of the reaction liquid in each reaction tank is controlled by the vacuum pump 10 to a desired degree of vacuum, whereby the sugar fatty acid Water or alcohol by-produced by the synthesis of ester is removed in a gas state.
The removed water, alcohol, etc. reach the condenser 9 through the collecting pipe 15, are condensed, and then are recovered in the condensate recovery tank 12.

[0018]

EFFECTS OF THE INVENTION According to the present invention, the complexity of recovering immobilized lipase particles used for sugar fatty acid ester synthesis can be eliminated, and sugar fatty acid ester can be continuously produced at low cost while maintaining high efficiency. The present invention will be described in detail based on examples and comparative examples. The present invention is not limited to the scope of the embodiments.

[0019]

【Example】

Example 1 A 42-mesh wire net in the form shown in FIG. 2 was attached as a separating device to the device shown in FIG. 1 having a reaction tank having a capacity of 2 liters. In the reaction vessel of the device, Novo zym43
5 g of immobilized lipase particles with a large particle size obtained by sieving 5 with 32 mesh were charged in each reaction tank until cyclohexanone overflowed as a solvent, and sugar was continuously added under stirring conditions of a stirring power of 1 KW / m ^3. A synthetic reaction of a fatty acid ester was performed. The reaction conditions and the quality obtained by the reaction were as follows. Reaction temperature: 70 ℃ Pressure of reaction liquid surface: 40 torr Capric acid methyl ester supply rate: 20 g / hour 60% Aq. Methylglucoside supply rate: 30 g / hour Cyclohexanone supply rate: 130 g / hour

The reaction liquid flowing out from the third tank was acetylated by a conventional method and analyzed by gas chromatography to measure the composition (area ratio) of the reaction product excluding the solvent.
On the other hand, the immobilized enzyme in each tank was measured for enzyme activity after washing with butanol. GC analysis composition Unreacted methyl glucoside (MG): 4.8% Methyl glucoside caprate monoester: 69.5% Methyl glucoside caprate diester: 2.7% Unreacted ester, unreacted fatty acid: 23.0% Enzyme activity after reaction (%) 1st Tank: 98% Second tank: 98% Third tank: 98% Method for measuring enzyme activity (%) after reaction; After the immobilized lipase particles used were separated from the reaction solution by filtration and thoroughly washed with t-BuOH After vacuum-drying at room temperature, 0.2 g thereof was precisely weighed in a 30 ml Erlenmeyer flask, 7 ml of a t-BuOH solution containing glycerin as a substrate and methyl lauric acid ester was added, and the mixture was reacted at 50 ° C. for 15 minutes, then produced. The product, glyceryl lauric acid monoester, was quantified by gas chromatography. At the same time, as a blank, the same enzymatic reaction was carried out with an unreacted enzyme, and the amount of glyceryl laurate monoester produced was measured and used as the standard (100%) of the activity of the immobilized lipase particles.

Example 2 In the apparatus shown in FIG. 1 having a reaction tank having a capacity of 2 liters, a separating pipe having a 50 mmφ and 30 mmH settling pipe was installed in the pipe connecting the reaction tanks in the form shown in FIG. The bottom of the settling tube was provided with a path leading to the lower side surface of each reaction tank to prevent the immobilized lipase particles from flowing out. Immobilized enzyme Novozym 435 was not sieved, and the particle size (average particle size: 400 μm) was charged to each reaction tank in an amount of 15 g, and cyclohexanone was added as a solvent to a position where it overflowed, and the stirring power was 1 KW / m ³ under stirring conditions. Then, the synthetic reaction of sugar fatty acid ester was continuously carried out. The reaction conditions and the quality obtained by the reaction were as follows. Reaction temperature: 70 ° C. Reaction pressure: 40 torr Methyl glucoside caprylate supply rate: 24 g / hour 70% Aq. Methyl glucoside supply rate: 28 g / hour Cyclohexanone supply rate: 200 g / hour

The reaction liquid flowing out from the third reaction tank was acetylated by a conventional method and analyzed by gas chromatography (GC) to measure the composition (area ratio) of the reaction product excluding the solvent. On the other hand, the immobilized lipase particles in each tank are
After washing with butanol, the residual enzyme activity was measured by the same method as in Example 1. GC analysis results Unreacted caprylic acid methyl glucoside (MG) 4.8% Methyl glucoside caprylic acid monoester: 71.1% Methyl glucoside caprylic acid diester: 2.3% Unreacted ester, unreacted fatty acid: 21.8% Enzyme activity after reaction (%) 1 reaction tank: 98% 2nd reaction tank: 98% 3rd reaction tank: 98%

[Brief description of drawings]

FIG. 1 is a conceptual diagram of a multi-paragraph sugar fatty acid ester synthesizer used in the production method of the present invention.

FIG. 2 is a conceptual diagram of a device for separating immobilized lipase particles using a wire mesh.

FIG. 3 is a conceptual diagram of a device for separating immobilized lipase particles using a sedimentation tube.

[Explanation of symbols]

 8 Reaction Tank 9 Condenser 10 Vacuum Pump 11 Reaction Liquid Recovery Tank 12 Condensate Recovery Tank 13 Jacket 13 14 Reaction Liquid Outlet 15 Collecting Pipe 16 Overflow Pipe 17 Wire Mesh 18 Gravity Settling Pipe 19 Rectifier Plate

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Takahisa Koyanagi 1-3-7 Main Office, Sumida-ku, Tokyo Lion Corporation

Claims (2)

[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 4 to 6 carbon atoms.
Sugar alcohols and at least one saccharide selected from these dehydrated condensates, and (B) a carbon atom number of 6 to 22
Ester of at least one fatty acid compound selected from saturated and unsaturated fatty acids and esterification products of the fatty acid and lower alcohols having 1 to 4 carbon atoms in the presence of an organic solvent with lipase. A method for producing a sugar fatty acid ester to be emulsified, which comprises the following steps (a) to (d): (a) a saccharide in a first reaction system in which lipase-immobilized particles are suspended. (A) and the fatty acid compound (B) are supplied to synthesize a sugar fatty acid ester, and a by-product containing water and alcohol produced in the synthesis of the sugar fatty acid ester is treated at a temperature of 30 to 100.
A step of removing the lipase-immobilized particles from the reaction solution of the step (a) at a temperature of 100 ° C. or less and a vacuum degree of 100 torr or less; and a second step in which the lipase-immobilized particles are suspended in the reaction solution.
By-products containing water and alcohol, which are supplied to the reaction system and are produced in the synthesis of sugar fatty acid ester, are heated at a temperature of 30 to 100.
A step of removing the lipase-immobilized particles from the reaction solution of the step (b), the step of removing the lipase-immobilized particles in the third step.
By-products containing water and alcohol, which are supplied to the reaction system and are produced in the synthesis of sugar fatty acid ester, are heated at a temperature of 30 to 100.
A step of removing the lipase-immobilized particles from the reaction solution of step (c) and removing sugar fatty acid ester from the reaction solution; 2. The production method according to claim 1, wherein step (c) is performed at least twice with the third reaction system in which the lipase-immobilized particles are suspended being replaced.