JPS6328118B2 - - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing sugar alcohol fatty acid esters.

More specifically, the present invention relates to a method for producing a sugar alcohol fatty acid ester by alcoholysing a sugar alcohol and a fatty acid ester in the presence of a base catalyst.

Sugar alcohol fatty acid esters have excellent surface activity, good biodegradability, and high safety, so they are used as additives for foods, cosmetics, pharmaceuticals, feed, and resins, metal processing oils, rust preventives, It is an extremely useful compound that has a wide range of uses such as textile oils.

Conventionally, methods for producing sugar alcohol fatty acid esters include (1) reacting sugar alcohols with fatty acid chlorides or fatty acid anhydrides, and (2) dehydrating sugar alcohols and fatty acids in the presence of a base catalyst or an acid catalyst. (3) sugar alcohol and fatty acid lower alkyl esters such as fatty acid methyl esters and fatty acid ethyl esters, and fatty acid esters such as fatty acid glycerides, in the presence or absence of a solvent capable of dissolving both, in trace amounts ( Methods of alcoholysis using a base catalyst (about 0.1 to 1.0% by weight based on the total amount of sugar alcohol and fatty acid ester) are known, but each method has the following drawbacks.

That is, in the first method, since fatty acid chlorides and fatty acid anhydrides are expensive, it is generally extremely disadvantageous to implement industrially, except in the case of specific sugar alcohol fatty acid esters such as sugar alcohol lower fatty acid esters. be. Also, the second method usually uses 200 to 250
Since it is necessary to carry out the reaction at a high temperature of °C, the main product is fatty acid ester of the sugar alcohol dehydration cyclization product, which has a cyclic ether skeleton and is produced by intramolecular dehydration and ring closure of the sugar alcohol itself. It has a fatal flaw in that the yield of fatty acid ester is extremely low. in particular,
For example, when sorbitol and fatty acids are reacted,
Large amounts of sorbitan fatty acid ester and sorbide fatty acid ester are produced, and only a small amount of sorbitol fatty acid ester is produced. Although it is possible to increase the production rate of sorbitol fatty acid ester to a certain extent by improving the catalyst and reaction conditions, even in this case it is not possible to avoid considerable by-product of sorbitan fatty acid ester and sorbide fatty acid ester.

In addition, the third method uses methanol, ethanol,
It is relatively highly reactive, such as propylene glycol and glycerin, and has extremely high or relatively high solubility in fatty acid esters such as fatty acid lower alkyl esters and fatty acid glycerides, and during alcoholysis, Alternatively, it is an extremely useful method for alcohols that do not easily cause side reactions such as dehydration condensation between molecules, and is widely practiced industrially. However, alcohols that have unique properties such as sugar alcohols having 4 to 9 hydroxyl groups, which are the target of the method of the present invention, have extremely low solubility in fatty acid esters, have poor reactivity, and are easy to undergo dehydration and ring closure. Generally, it is necessary to perform alcoholysis in the presence of a special solvent that can dissolve both sugar alcohols and fatty acid esters, which increases production and purification costs. There is a risk that the solvent used during alcoholysis may remain in the product. Therefore, it cannot be said that it is an industrially advantageous method. In any case, conventional methods for producing sugar alcohol fatty acid esters have various drawbacks, and even though sugar alcohol fatty acid esters have excellent performance and high safety, they are not widely used. This is the biggest reason.

As a result of intensive studies to overcome the deficiencies of conventional methods, the present inventors have discovered that when producing sugar alcohol fatty acid esters by reacting sugar alcohols and fatty acid esters in the presence of a base catalyst to carry out alcoholysis, By using a base catalyst in an amount within a specific range that is significantly increased from the amount used in the past, the compatibility of sugar alcohols and fatty acid esters was unexpectedly improved, making it possible to use sugar alcohols with 4 to 9 hydroxyl groups. In this case, the reaction can proceed smoothly under mild conditions without the use of solvents, which were previously thought to be essential in this type of reaction. The present inventors have discovered that it is now possible to almost completely suppress the production of sugar alcohols, and that the desired sugar alcohol fatty acid ester can be produced with high selectivity, leading to the completion of the present invention.

The present invention uses a sugar alcohol having 4 to 9 hydroxyl groups and a fatty acid ester in the presence of a basic catalyst of 3 to 15% by weight based on the total amount of the sugar alcohol and fatty acid ester, using substantially a solvent. This is a method for producing a sugar alcohol fatty acid ester, which is characterized in that alcoholysis is carried out without any alcoholysis.

Next, the present invention will be explained in detail.

The sugar alcohol used in the present invention is a type of polyhydric alcohol having 4 to 9 hydroxyl groups,
Specifically, erythritol having 4 hydroxyl groups,
Tetritols such as threitol, pentitols such as lipitor, arabitol, and xylitol having 5 hydroxyl groups, hexitols such as allitol, sorbitol, mannitol, dulcitol, ideitol, and altritol having 6 hydroxyl groups, boremitol having 7 hydroxyl groups, Typical examples include heptitols such as sedoheptitol and perseitol, maltitol and lactitol each having nine hydroxyl groups. Further, cyclic sugar alcohols such as inositol, sucillitol, quercitol, etc. can also be used.

Among them, sorbitol and mannitol are produced in large quantities by hydrogenating glucose and mannose, respectively, in the presence of a nickel catalyst.
In addition, it is produced at a low cost, so it is one of the sugar alcohols that can be most advantageously used in the present invention.

Most of these sugar alcohols have optical isomers, and any of the D-form, L-form, and DL-form can be used.

On the other hand, as the fatty acid ester, an ester of a fatty acid and a monovalent to trivalent alcohol is used.
Specifically, fatty acid esters of lower monohydric alcohols such as methanol, ethanol, isopropanol, ethylene glycol mono-lower alkyl ether, carbitol (diethylene glycol mono-lower alkyl ether), lower monohydric alcohols such as ethylene glycol, propylene glycol, butanediol, etc.
Typical examples include fatty acid esters of alcohols, fatty acid esters of lower trihydric alcohols such as glycerin, and trimethylolpropane. Among them, glycerin fatty acid esters are available in large quantities and at low cost as fats such as beef tallow, hydrogenated beef tallow, palm oil, palm kernel oil, coconut oil, olive oil, soybean oil, rapeseed oil, cottonseed oil, linseed oil, castor oil, lard, and fish oil. It is one of the fatty acid esters that can be most preferably used in the present invention. There are three types of glycerin fatty acid esters: glycerin monofatty acid esters (monoglycerides), glycerin difatty acid esters (diglycerides), and glycerin trifatty acid esters (triglycerides). Monoglycerides and diglycerides can also be used. The same applies to other lower trihydric alcohol fatty acid esters, and both monoesters and diesters can be used in the case of lower dihydric alcohol fatty acid esters.

In addition, the fatty acid component constituting the fatty acid ester is not particularly limited, but from the viewpoint of the usefulness of the final sugar alcohol fatty acid ester, fatty acids having about 6 to 24 carbon atoms are usually most suitable. . These fatty acid components may be either saturated fatty acids or unsaturated fatty acids, and their carbon chains are not limited to linear ones, but branched ones can also be used. Note that a fatty acid having a substituent such as a hydroxyl group may also be used.

Typical examples of these fatty acids include caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, ricinoleic acid,
Examples include elaidic acid, arachidic acid, behenic acid, and lignoceric acid.

Note that the sugar alcohols and fatty acid esters mentioned above do not necessarily need to be used alone, and two or more of each can be used in combination.

In addition, the usage ratio of sugar alcohol and fatty acid ester depends on the type, molecular weight, etc. of the sugar alcohol and fatty acid ester, and the average degree of substitution of the target sugar alcohol fatty acid ester, i.e., monoester, diester,
Although it varies depending on the composition ratio of triester, etc., usually sugar alcohol: fatty acid ester = 5 to 70:30
-95 weight ratio, more preferably 10-60:40-90 weight ratio, most preferably 15-55:45-85 weight ratio is suitable. Generally, as the amount of sugar alcohol used increases,
The average degree of substitution of sugar alcohol fatty acid esters tends to be lower, and the production rate of sugar alcohol monofatty acid esters tends to be higher.

Next, the base catalyst used in the present invention includes alkali metal carbonates such as lithium carbonate, sodium carbonate, and potassium carbonate, alkaline earth metal carbonates such as magnesium carbonate, calcium carbonate, and barium carbonate, lithium hydroxide, and hydroxide. Alkali metal hydroxides such as sodium and potassium hydroxide, alkaline earth metal hydroxides such as magnesium hydroxide, calcium hydroxide, and barium hydroxide, sodium oxide,
oxides of alkali metals or alkaline earth metals such as magnesium oxide, calcium oxide, and barium oxide; alkali metal bicarbonates such as sodium bicarbonate and potassium bicarbonate; ammonium salts such as ammonium carbonate and ammonium bicarbonate;
sodium methylate, sodium ethylate,
Alcoholates such as potassium methylate and potassium butyrate, sodium acetate, potassium acetate, fatty acid salts such as soaps, triethylamine, tributylamine, laurylamine, 1,8-diazabicyclo[5.4.0]undecene-7, 1,4 ,5,
6-tetrahydropyrimidine, formamidine,
Typical examples include organic bases such as N-ethylmorpholine.

Among them, alkali metal carbonates and alkali metal hydroxides exhibit particularly excellent catalytic effects, are inexpensive, and are easy to handle, so they are among the basic catalysts that can be most preferably used in the present invention. Furthermore, when both of the above catalysts are used together, the catalytic effect is further improved, so
Particularly preferred.

These base catalysts need to be used in an amount of 3 to 15% by weight based on the total amount of the sugar alcohol and fatty acid ester mentioned above.

If the amount of the base catalyst used is less than the above range, the catalytic effect will be extremely insufficient, and the affinity between the sugar alcohol and fatty acid ester, which originally have poor compatibility, will hardly be improved, which is not preferable. . or,
Even if the base catalyst is used in an amount larger than the upper limit of the above range, no significant advantage will be exhibited; on the contrary, the viscosity of the reaction mass during alcoholysis will increase significantly, making stirring difficult, or the conversion of fatty acid esters to fatty acids This is undesirable because the ratio of saponification reactions in which salts (so-called soaps) are produced as by-products increases.

The optimum amount of the base catalyst to be used varies depending on the type of sugar alcohol, fatty acid ester, and base catalyst, reaction temperature, etc., but in general, the optimum amount is 5 to 10% by weight based on the total amount of sugar alcohol and fatty acid ester. Favorable results are obtained.

A sugar alcohol fatty acid ester is produced by performing alcoholysis using the above-mentioned sugar alcohol, fatty acid ester, and base catalyst.

The temperature when performing alcoholysis is 90 to 180
°C, more preferably 100 to 170 °C, most preferably
A temperature of about 110 to 150°C is good.

If the temperature is below the lower limit of the above range, the reaction rate will drop significantly, and if the temperature is higher than the upper limit, side reactions such as intramolecular dehydration ring closure reaction of sugar alcohols will tend to proceed, resulting in sugar alcohol fatty acid esters. Both are undesirable because they lead to a decrease in yield and deterioration of quality. Although the reaction can give satisfactory results even under normal pressure, it is possible to remove the alcohols produced by the alcoholysis reaction from the reaction system by keeping it under reduced pressure or by blowing inert gas such as nitrogen gas. If removed, the reaction can proceed in a more desirable direction.

Various methods can be used to carry out the above-mentioned alcoholysis, such as a method in which a sugar alcohol, a fatty acid ester, and a base catalyst are simultaneously charged into a reactor to carry out the alcoholysis; After charging both the ester and the base catalyst into the reactor and carrying out the saponification reaction to some extent,
It is possible to arbitrarily adopt a method in which alcoholysis is carried out by charging sugar alcohol, or a method in which only fatty acid ester is charged into the reactor in advance, and then sugar alcohol and base catalyst are simultaneously charged and alcoholysis is carried out. It is possible.

The reactor is usually a tank reactor equipped with a heating device and a stirring device, or a tube reactor, etc.
Of course, it is also possible to use other types of reactors. Furthermore, if necessary, a cooling device or a device for maintaining the inside of the reactor at reduced pressure may be installed. Further, the alcoholysis reaction can be carried out in a batch manner, a semi-batch manner, or a continuous manner.

The time required for the alcoholysis reaction varies depending on the type and ratio of sugar alcohol, fatty acid ester, and base catalyst used, reaction temperature, reaction pressure, type of reactor, etc., but it usually ranges from 10 minutes to 20 hours. Preferably 30 minutes to 15 hours, most preferably 1 to 15 hours.
Approximately 10 hours is appropriate. The viscosity of the reaction mass tends to increase as the reaction progresses, so by measuring changes in the viscosity of the reaction mass, it is possible to roughly know the progress of the reaction and the end point.
Further, by analyzing the remaining amount of unreacted raw materials and the content of products in the reaction mass using gas chromatography, liquid chromatography, etc., it is also possible to accurately know the progress status and end point of the reaction.

In the method of the present invention, in addition to the production reaction of sugar alcohol fatty acid ester by alcoholysis of sugar alcohol and fatty acid ester with a base catalyst,
A reaction for producing fatty acid salts, that is, soaps, by the saponification reaction of the fatty acid ester and the base catalyst also proceeds at the same time.

The latter saponification reaction has the effect of improving the compatibility of the sugar alcohol and fatty acid ester, which originally have little compatibility, and promoting the reaction for producing the sugar alcohol fatty acid ester. Therefore, it is also effective to add separately synthesized soaps at the beginning of the reaction, and in this case it is also possible to reduce the amount of the base catalyst.

In addition to sugar alcohol fatty acid esters, the reaction products obtained by the method of the present invention include soaps,
Contains unreacted sugar alcohol, unreacted fatty acid ester, unreacted base catalyst, etc. This reaction product can be used as it is for various purposes, but unreacted raw materials and by-products other than the sugar alcohol fatty acid ester in the reaction product can be extracted, converted to other derivatives, or
It can be easily removed by known methods such as filtration and crystallization, and ultimately a highly purified sugar alcohol fatty acid ester can be obtained.

The sugar alcohol fatty acid ester obtained by the method of the present invention is characterized by an extremely high proportion of low-substitution sugar alcohol fatty acid esters, that is, monoesters and diesters, which have the highest utility value. Another major feature is that almost no fatty acid ester is produced in the dehydrated cyclized sugar alcohol, which has a cyclic ether core produced by intramolecular dehydration and cyclization of the sugar alcohol itself.

As detailed above, according to the present invention, high quality sugar alcohol fatty acid esters can be produced using inexpensive sugar alcohols and fatty acid esters as main raw materials under mild conditions and without using substantially any solvent. It is industrially extremely useful because it can be produced with high selectivity and economically.

The present invention will be explained in more detail below using Examples and Comparative Examples.

Example 1 150 g of D-sorbitol, 350 g of beef tallow, and 25 g of potassium carbonate were placed in the glass reactor equipped with a stirrer in 1, and an alcoholysis reaction was carried out at 150°C.
After about 1 hour had passed after the start of the reaction, the reaction mass began to bubble and gradually thicken, and there was a noticeable tendency for the entire reaction mass to become homogeneous. After a total of 5 hours of reaction, the reaction mass became a fairly viscous and homogeneous liquid (light brown color).

Finally, 510 g of reaction product was obtained.

The reaction product solidified upon cooling to room temperature, becoming a slightly sticky solid. Quantitative analysis of the reaction product using gas chromatography after trimethylsilyl etherification showed that 42.3% by weight of sorbitol tallow fatty acid ester (monoester/diester = 68/32 weight ratio) and potassium tallow fatty acid.
18.7% by weight, beef tallow fatty acid glyceride 21.5% by weight
(total amount of mono-, di-, and triglycerides), unreacted D-sorbitol, glycerin, etc. were 17.5% by weight, and only trace amounts of sorbitan tallow fatty acid ester were detected.

Comparative Example 1 An alcoholysis reaction was carried out at 150° C. in the same manner as in Example 1 using 150 g of D-sorbitol, 350 g of beef tallow, and 10 g of potassium carbonate. About 3 hours after the start of the reaction, the reaction mass tended to bubble slightly, but no thickening or homogenization of the reaction mass was observed, and when stirring was stopped, it turned into a liquid phase and an extremely viscous semi-solid. Immediate separation into two phases was observed. Thereafter, the reaction was continued for a total of 10 hours, but the reaction was stopped because there was almost no tendency for thickening or homogenization of the reaction mass. A portion of the liquid phase portion and semi-solid phase portion (liquid phase portion/semi-solid phase portion≒7/3 weight ratio) in the reaction mass was sampled and analyzed by gas chromatography, and it was found that most of the liquid phase portion was was beef tallow fatty acid triglyceride, and some beef tallow fatty acid diglyceride and beef tallow fatty acid monoglyceride were also detected. In addition, the semi-solid phase was mainly composed of D-sorbitol, and some potassium tallow fatty acid was also detected. However, only a small amount of sorbitol tallow fatty acid ester was detected in the semi-solid phase.

Example 2 A reactor similar to Example 1 was charged with 275 g of coconut oil and 10 g of potassium hydroxide, and after saponifying the coconut oil at 125°C for 1 hour, 225 g of D-sorbitol and 25 g of potassium carbonate were charged. Enter,
The alcoholysis reaction was carried out at 125°C. From about 20 minutes after the start of the alcoholysis reaction, the reaction mass became noticeably prone to bubbling, thickening, and homogenization. As a result of carrying out the alcoholysis reaction for a total of 4 hours, the reaction mass became a viscous homogeneous liquid (white), and 515 g of a reaction product was finally obtained.

The reaction product solidified upon cooling to room temperature, becoming a slightly sticky solid. The reaction product is shown in Example 1.
As a result of quantitative analysis using a method similar to total amount), unreacted sorbitol, glycerin, etc.
The amount was 23.1% by weight, and no sorbitan coconut fatty acid ester was detected.

Example 3 400 g of hydrogenated beef tallow and 5 g of sodium hydroxide were charged into the same reactor as in Example 1, and the saponification reaction was carried out at 110°C for 1 hour. Then, 20 g of potassium carbonate was charged, and then D- 100 g of sorbitol was gradually charged over 1 hour. About 30 minutes after the start of charging D-sorbitol, bubbling, thickening, and homogenization of the reaction mass were observed. After charging D-sorbitol, the alcoholysis reaction was carried out at 110℃ for another 7 hours, resulting in the reaction mass becoming a viscous homogeneous liquid (white, which becomes a hard solid when cooled to room temperature) and finally weighing 508g. A reaction product was obtained. Quantitative analysis of the reaction product in the same manner as in Example 1 revealed that sorbitol hydrogenated beef tallow fatty acid ester was 35.4% by weight (monoester/diester/triester = 60/38/2 weight ratio) and hydrogenated beef tallow fatty acid salt was 20.3% by weight. Weight% (total amount of sodium salt and potassium salt), hydrogenated beef tallow fatty acid glyceride 37.1% by weight (total amount of mono-, di-, and triglyceride), unreacted D
-Sorbitol, glycerin, etc. were 7.2% by weight, and sorbitan tallow fatty acid ester was not detected.

Example 4 D-sorbitol was added to the same reactor as in Example 1.
Prepare 200g and 300g of methyl stearate,
After dehydrating and drying for 30 minutes at 120°C and 30 mmHgabs, 20 g of sodium methylate and 20 g of sodium carbonate were added, and alcoholysis reaction was carried out at 120°C and 10 mmHgabs for 3 hours. As the alcoholysis reaction progressed, methanol distilled out and was collected in a trap cooled in a dry ice-acetone bath.

The reaction mass finally became a viscous homogeneous liquid (white, solidified to a hard solid when cooled to room temperature). 480 g of reaction product was obtained.

As a result of quantitative analysis of the reaction product in the same manner as in Example 1, it was found that sorbitol stearate
48.5% by weight (monoester/diester = 71/29
(weight ratio), sodium stearate was 25.0% by weight, and the remainder was unreacted D-sorbitol, unreacted methyl stearate, and others. Moreover, sorbitan stearate was not detected.

Example 5 Using the same reactor as in Example 1, an alcoholysis reaction was carried out under exactly the same conditions as in Example 2, except that 225 g of D-mannitol was used instead of D-sorbitol. The reaction mass became a viscous homogeneous liquid (white, solidified when cooled to room temperature), and 513 g of reaction product was finally obtained. As a result of quantitative analysis of the reaction product in the same manner as in Example 1,
Mannitol coconut fatty acid ester 41.7% by weight
(monoester/diester = 71/29 weight ratio), coconut fatty acid potassium 23.1% by weight, coconut fatty acid glyceride 10.5% by weight (total amount of mono-, di-, and triglycerides), unreacted D-mannitol, glycerin, etc. 24.7% by weight. , mannitan coconut fatty acid ester was not detected.

Example 6 In a 200 ml glass reactor equipped with a stirrer, 40 g of D-mannitol, 30 g of lauric acid triglyceride, 30 g of lauric acid monoglyceride, and 3 potassium carbonate were added.
g was charged, and the allurisis reaction was carried out at 130°C. After about 5 minutes had passed from the start of the reaction, the reaction mass began to foam violently and tend to thicken and become more uniform. The reaction was carried out for a total of 2 hours, and 101 g of a viscous homogeneous liquid reaction product (white, solidified when cooled to room temperature)
I got it.

As a result of quantitative analysis of the reaction product in the same manner as in Example 1, mannitol lauric acid ester 40.1
Weight% (monoester/diester = 81/19 weight ratio), potassium laurate 9.1% by weight, lauric acid glyceride 29.5% by weight (total amount of mono-, di-, and triglycerides), unreacted D-mannitol, glycerin, etc. 21.3% by weight and mannitan laurate was not detected.

Example 7 In a reactor similar to Example 6, erythritol 25
125 g, prepared with 75 g of beef tallow and 12 g of potassium carbonate.
The alcoholysis reaction was carried out at .degree. C. for 3 hours to obtain 107 g of an extremely viscous homogeneous liquid reaction product (light brown in color, which solidified when cooled to room temperature).

As a result of quantitative analysis of the reaction product in the same manner as in Example 1, it was found that erythritol beef tallow fatty acid ester
38.7% by weight (monoester/diester = 71/29
weight ratio), beef tallow fatty acid potassium is 33.0% by weight,
The remainder was tallow fatty acid glyceride (a mixture of mono-, di-, and triglycerides), unreacted erythritol, glycerin, and the like.

Example 8 In a reactor similar to Example 6, 40 g of xylitol was added.
60 g of methyl palmitate and 4 g of potassium carbonate were charged, and an alcoholysis reaction was carried out at 150°C and 10 mmHg for 2 hours to produce a viscous homogeneous liquid reaction product95.
g (pale yellow, solidified upon cooling to room temperature) was obtained.

As a result of quantitative analysis using the same method as in Example 1, it was found that xylitol palmitate ester was 52.3% by weight (monoester/diester = 73/27 weight ratio), potassium palmitate was 15.8% by weight, and the rest was unreacted xylitol and unreacted. It contained methyl palmitate and others.

Example 9 65 g of palm oil and 2 g of potassium hydroxide were placed in the same reactor as in Example 6, and a saponification reaction was carried out at 130°C for 30 minutes. Then, 35 g of maltitol and 4 g of potassium carbonate were added, and the mixture was heated at 130°C. The alcoholysis reaction was carried out for 4 hours. 103 g of a viscous, homogeneous liquid reaction product (pale yellow, solidified upon cooling to room temperature) was obtained. As a result of quantitative analysis using the same method as in Example 1, 40.5% by weight of maltitol palm fatty acid ester (monoester/diester/triester =
67/29/4 weight ratio), palm fatty acid potassium 22.1
The remainder was palm fatty acid glyceride (a mixture of mono-, di- and triglycerides), unreacted maltitol, glycerin, etc.

Claims (1)

[Scope of Claims] 1. A sugar alcohol having 4 to 9 hydroxyl groups and a fatty acid ester are substantially dissolved in a solvent in the presence of a base catalyst of 3 to 15% by weight based on the total amount of the sugar alcohol and fatty acid ester. A method for producing a sugar alcohol fatty acid ester, characterized by carrying out alcoholysis without using. 2. The method for producing a sugar alcohol fatty acid ester according to claim 1, wherein the sugar alcohol is hexitol. 3. The method for producing a sugar alcohol fatty acid ester according to claim 1 or 2, wherein the sugar alcohol is sorbitol. 4. The method for producing a sugar alcohol fatty acid ester according to claim 1 or 2, wherein the sugar alcohol is mannitol. 5. The method for producing a sugar alcohol fatty acid ester according to claim 1, wherein the sugar alcohol is pentitol. 6. The method for producing a sugar alcohol fatty acid ester according to claim 1, wherein the sugar alcohol is tetritol. 7. The method for producing a sugar alcohol fatty acid ester according to claim 1, wherein the sugar alcohol is heptitol. 8. The method for producing a sugar alcohol fatty acid ester according to claim 1, wherein the sugar alcohol is maltitol. 9. The method for producing a sugar alcohol fatty acid ester according to claim 1, wherein the sugar alcohol is lactitol. 10. The method for producing a sugar alcohol fatty acid ester according to claim 1, wherein the fatty acid ester is an ester of a fatty acid having 6 to 24 carbon atoms and a monovalent to trivalent alcohol. 11. The method for producing a sugar alcohol fatty acid ester according to claim 1 or 10, wherein the fatty acid ester is a fatty acid glyceride. 12. The method for producing a sugar alcohol fatty acid ester according to claim 1, wherein the base catalyst is an alkali metal base catalyst. 13. The method for producing a sugar alcohol fatty acid ester according to claim 1 or 12, wherein the base catalyst is an alkali metal carbonate. 14 Claim 1 in which an alkali metal carbonate and an alkali metal hydroxide are used together as a base catalyst
The method for producing a sugar alcohol fatty acid ester according to item 1 or 12. 15. The method for producing a sugar alcohol fatty acid ester according to claim 1, wherein alcoholysis is carried out at a temperature of 90 to 180°C.