JP2008094805A - Manufacturing method of polyglycerin condensed-ricinoleic acid ester - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a method for manufacturing a polyglycerin condensed-ricinoleic acid ester that slows down the coagulation speed appropriately when incorporated with a coagulant for soybean curds and allows the manufacture of soybean curds of good qualities. <P>SOLUTION: The manufacturing method of the polyglycerin condensed-ricinoleic acid ester comprises a step (I) for obtaining a condensed ricinoleic acid by subjecting ricinoleic acid to a polycondensation reaction, and a step (II) for subjecting the condensed ricinoleic acid obtained in the step (I) and polyglycerin to an esterification reaction, where the condensed ricinoleic acid obtained in the step (I) is one having a predetermined high molecular weight ratio of at least 1. <P>COPYRIGHT: (C)2008,JPO&INPIT

Description

  The present invention relates to a method for producing a polyglycerin condensed ricinoleic acid ester, and a coagulation preparation for tofu containing the polyglycerin condensed ricinoleic acid ester obtained by the production method.

  Conventionally, as a coagulant for tofu, inorganic salts such as magnesium chloride, magnesium sulfate, calcium chloride or calcium sulfate, or organic acids such as glucono delta lactone have been used. However, when these inorganic salts are used as a coagulant for tofu, the coagulation rate of soy milk is high and the tofu's internal phase is fine, homogeneous, rich in water retention, texture and flavor unless it is a highly skilled person. It was difficult to make excellent tofu. In particular, magnesium chloride has been used for the production of tofu as a bitter juice for a long time. Tofu using this has been preferred by consumers because of its unique taste, but its coagulation rate is extremely fast, for example secondary It was difficult to make tofu with a fine internal phase and fineness with “silk tofu” that was not molded. Therefore, bitter juice is only partially used in handmade tofu stores, etc., and it has been extremely difficult to use it in mass production on a factory scale. Therefore, calcium sulfate is widely used today because of its relatively slow coagulation rate, but the flavor of tofu using this does not reach the flavor of tofu with magnesium chloride, and it is not necessarily accepted by consumers. It ’s hard to say. On the other hand, glucono delta lactone has been used extensively in “silk tofu” etc. in recent years because it can be coagulated easily and a homogeneous tofu of the inner phase is obtained, but the sour taste remains in the finished tofu. There is a problem in terms of flavor.

In this way, in the method for producing tofu using the inorganic salt-based tofu coagulant such as bitter juice, the coagulation reaction of the coagulant such as bitter juice is remarkably fast, so it is difficult to control the coagulation rate and obtain a stable quality tofu. It was difficult. A method for delaying the coagulation reaction of bitter juice by emulsifying bitter juice is disclosed (Patent Documents 1, 2, and 3). In addition to these documents, Patent Documents 4 and 5 disclose a technique using polyglycerin condensed ricinoleic acid ester or the like as an emulsifier in order to prepare a bitter emulsion.
Japanese Examined Patent Publication No. 62-5581 JP-A-10-57002 JP 2000-32942 A JP 2006-101848 A JP 2006-204184 A

  Although the techniques of Patent Documents 1 to 3 are effective in stabilizing the emulsion of bitter emulsion, finely dispersed high-quality tofu with finely dispersed bitter emulsion in soy milk Therefore, a large dispersion shear force is required. Moreover, in the point of making the coagulation | solidification rate of tofu suitable, all the improvement of all of patent documents 1-5 is desired.

  An object of the present invention is to provide a method capable of producing a polyglycerin condensed ricinoleic acid ester capable of producing a high-quality tofu with a moderately slow coagulation rate when blended in a tofu coagulation preparation.

The present invention includes a step (I) of obtaining a condensed ricinoleic acid by polycondensation reaction of ricinoleic acid, and a step (II) of esterifying the condensed ricinoleic acid obtained in step (I) with polyglycerin. A method for producing a polyglycerin condensed ricinoleic acid ester, wherein the condensed ricinoleic acid obtained in step (I) is a condensed ricinoleic acid having a high molecular weight ratio calculated from the following formula (1) of 1 or more. The present invention relates to a method for producing an acid ester.
High molecular weight ratio = S1 / S2 Formula (1)
S1: Peak area corresponding to a molecular weight distribution of 2000 or more in terms of polystyrene by gel permeation chromatography of condensed ricinoleic acid S2: Molecular weight in the molecular weight distribution of polystyrene by gel permeation chromatography of condensed ricinoleic acid of 100 Peak area equivalent to more than 2000

  The present invention also includes at least one inorganic salt coagulant selected from the group consisting of polyglycerin condensed ricinoleic acid ester obtained by the production method of the present invention, (b) magnesium chloride, magnesium sulfate and calcium chloride. The present invention relates to a coagulation preparation for tofu.

  According to the present invention, it is possible to produce a polyglycerin condensed ricinoleic acid ester exhibiting excellent performance as an emulsifier used in a coagulated preparation for tofu.

<Method for producing polyglycerol condensed ricinoleic acid ester>
<Process (I)>
Step (I) is a step of obtaining condensed ricinoleic acid by polycondensation reaction of ricinoleic acid.

  The temperature of the polycondensation reaction of ricinoleic acid is preferably 170 ° C. to 260 ° C., more preferably 180 ° C. to 250 ° C., and still more preferably 190 ° C. to 230 ° C. from the viewpoints of reaction rate and quality. A catalyst may or may not be used for the reaction, but when used, sodium hydroxide, potassium hydroxide, calcium hydroxide, and magnesium hydroxide are preferred. The amount of catalyst used is preferably from 0.1 to 2% by weight, more preferably from 0.2 to 1.5% by weight, based on ricinoleic acid. The reaction time is preferably 2 to 20 hours, more preferably 3 to 20 hours, from the viewpoint of the degree of condensation of ricinoleic acid. The reaction pressure is normal pressure or reduced pressure. From the viewpoint of removal of produced water, the reaction pressure is preferably reduced, and more preferably 66.6 kPa or less. Nitrogen is preferably introduced into the reaction system from the viewpoint of preventing coloring and removing generated water, and the nitrogen flow rate is preferably 10 to 200 mL / min · kg, more preferably 20 to 100 mL / min · kg.

In the present invention, from the viewpoint of the solidification property of tofu, the condensed ricinoleic acid obtained in step (I) needs to have a high molecular weight ratio of 1 or more, preferably 1.5 to 4 calculated from the following formula (1). is there.
High molecular weight ratio = S1 / S2 Formula (1)
S1: Peak area corresponding to a molecular weight distribution of 2000 or more in terms of polystyrene by gel permeation chromatography of condensed ricinoleic acid S2: Molecular weight in the molecular weight distribution of polystyrene by gel permeation chromatography of condensed ricinoleic acid of 100 Peak area equivalent to more than 2000

Here, the conditions of gel permeation chromatography (GPC) are as follows.
* GPC conditions Column: G4000HXL + 2000HXL (anion)
Column temperature: 40 ° C
Mobile phase: 50mmol / L CH ₃ COOH / THF
Flow rate: 1.0ml / min
Detector: RI
Sample concentration: 5ml / mL (THF solvent)
Injection volume: 100μL

  There are no particular limitations on the high molecular weight ratio of the condensed ricinoleic acid obtained in step (I), but it is preferable to adjust the reaction temperature, the amount of nitrogen introduced, the reaction pressure, the reaction time, and the like. For example, the polymerization reaction temperature of ricinoleic acid is 170 to 250 ° C., nitrogen is streamed at 10 to 100 mL / min · kg, heated under reduced pressure of 10 to 100 kPa while removing generated water, and cooled after 6 to 19 hours. To do. It is preferable to perform such an operation.

  Examples of the condensed ricinoleic acid obtained by the step (I) include those having an average degree of polymerization of about 3 to 10. Preferably, the average degree of polymerization is about 4-7.

<Process (II)>
Step (II) is a step of esterifying the condensed ricinoleic acid obtained in step (I) with polyglycerin.

  Examples of the polyglycerol include those having an average degree of polymerization of about 2 to 15. The average degree of polymerization is preferably about 3 to 10. Specifically, for example, triglycerin, tetraglycerin, hexaglycerin and the like are preferable.

  In the esterification reaction of condensed ricinoleic acid and polyglycerin, it is preferable to use 2 to 5 moles, more preferably 2.5 to 4.5 moles of condensed ricinoleic acid with respect to polyglycerin. Reaction temperature is 170-260 degreeC from a viewpoint of reaction rate and quality, More preferably, it is 180-250 degreeC, More preferably, it is 190-230 degreeC. The reaction time is 5 to 15 hours, more preferably 6 to 15 hours, from the viewpoint of the degree of esterification progress. The acid value after esterification is preferably 5 or less, more preferably 3 or less, and still more preferably 2 or less. A catalyst may or may not be used to promote the reaction, but sodium hydroxide, potassium hydroxide, calcium hydroxide, and magnesium hydroxide are preferred when used. The amount of catalyst used is preferably 0.1 to 2% by weight, more preferably 0.15 to 1.5% by weight, based on the total charge. The reaction time is preferably 2 to 20 hours, more preferably 3 to 20 hours, because the coagulation rate is moderately delayed and a tofu with good quality can be produced. The reaction pressure is normal pressure or reduced pressure, but it is preferably reduced pressure from the viewpoint of removal of produced water, more preferably 66.6 kPa or less. Nitrogen is preferably flowed into the reaction system from the viewpoint of coloring prevention and removal of generated water, and the nitrogen flow rate is preferably 10 to 200 mL / min · kg, more preferably 20 to 100 mL / min · kg.

<Coagulation preparation for tofu>
The tofu coagulation preparation of the present invention comprises (a) a polyglycerin condensed ricinoleic acid ester (hereinafter referred to as (a) component) obtained by the production method of the present invention, (b) magnesium chloride, magnesium sulfate and calcium chloride. 1 type or more of inorganic salt type coagulant chosen from the group (henceforth (b) component) is contained.

  Examples of the inorganic salt-based coagulant used in the present invention include magnesium chloride, magnesium sulfate, and calcium chloride. These inorganic salts may be either anhydrous or water containing crystallization (eg, magnesium chloride hexahydrate, magnesium sulfate heptahydrate, calcium chloride dihydrate, etc.). These inorganic salt-based coagulants can be used alone or as a mixture of two or more thereof. From the viewpoint of tofu flavor, it is preferable to use magnesium chloride alone.

  The tofu coagulation preparation of the present invention is not particularly limited, but for example, the component (a) is preferably 0.1 to 5% by weight, more preferably 0.5 to 3% by weight, 2.5% by weight is particularly preferred. The component (b) is preferably contained in an amount of 5 to 30% by weight, more preferably 8 to 28% by weight, particularly preferably 10 to 25% by weight.

  The tofu coagulation preparation of the present invention can also contain components other than the component (a) and the component (b).

  The coagulation preparation for tofu of the present invention preferably contains (c) an oil and fat [hereinafter referred to as component (c)]. Component (c) is a polyhydric alcohol fatty acid ester having fluidity at room temperature (for example, 25 ° C.), and includes triglyceride, diglyceride and the like. Examples of triglycerides include rapeseed oil, soybean oil, fish oil, safflower oil, corn oil, palm oil, palm kernel oil, coconut oil, beef tallow, or triglycerides composed of medium chain fatty acids having 8 to 10 carbon atoms. Examples include fractionated oils, transesterified oils, hydrogenated oils, and triglycerides obtained by arbitrarily mixing these, and corn oil, rapeseed oil, and soybean oil are particularly preferable. As the diglyceride, those having 6 to 24 carbon atoms of the constituent fatty acid are preferable, and diglyceride containing oleic acid as the constituent fatty acid is particularly preferable. The coagulation preparation of the present invention is not particularly limited, but for example, the component (c) is preferably contained in an amount of 10 to 60% by weight, more preferably 30 to 60% by weight.

  Moreover, the coagulation preparation for tofu of this invention can contain (d) polyglycerol fatty acid ester [henceforth (d) component]. The polyglycerol fatty acid ester used in the present invention is an esterification product of polyglycerol and a fatty acid, and is produced by a known esterification reaction or the like. The polyglycerin is a mixture of polyglycerin having different degrees of polymerization, which is usually obtained by heating glycerin, glycidol, epichlorohydrin or the like to cause a polycondensation reaction. The polyglycerin used in the present invention has an average degree of polymerization of about 2 to 10, for example, diglycerin (average degree of polymerization 2), triglycerin (average degree of polymerization 3), tetraglycerin (average degree of polymerization 4), Examples include hexaglycerin (average degree of polymerization 6), octaglycerin (average degree of polymerization 8), decaglycerin (average degree of polymerization 10), and the like.

  The constituent fatty acid of the polyglycerol fatty acid ester is not particularly limited as long as it is a fatty acid derived from edible animal and vegetable oils and fats, such as caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, About 50% by weight of one or more mixtures selected from the group of linoleic acid and erucic acid, preferably one or more selected from the group of caprylic acid, capric acid and lauric acid % Or more, preferably about 70% by weight or more, more preferably about 90% by weight or more fatty acid or fatty acid mixture.

  Although content of (d) component in the coagulation preparation for tofu of this invention is not specifically limited, For example, 0.1-5 weight%, Furthermore, 0.2-4 weight% is preferable, 0.4- 3% by weight is particularly preferred.

  Moreover, the coagulation preparation for tofu of this invention can contain (e) propylene glycol fatty acid ester [henceforth (e) component]. The propylene glycol fatty acid ester used in the present invention is an esterification product of propylene glycol and a fatty acid, and is produced by a per se known esterification reaction or the like. The ester may be a monoester, a diester, or a mixture thereof. Preferably, it is a diester, and in the case of a mixture, the diester should contain about 50% by weight or more, preferably about 80% by weight or more, more preferably 90% by weight or more. Although content of (e) component in the coagulation preparation for tofu of this invention is not specifically limited, For example, 0.1-5 weight%, Furthermore, 0.2-4 weight% is preferable, 0.4- 3% by weight is particularly preferred.

  Moreover, the coagulation preparation for tofu of this invention can contain (f) sorbitan fatty acid ester [henceforth (f) component]. Sorbitan fatty acid ester is an esterification product of sorbitol or sorbitan and a fatty acid, and is produced by a known esterification reaction or the like. Although content of (f) component in the coagulation preparation for tofu of this invention is not specifically limited, For example, 0.1 to 5 weight%, Furthermore, 0.2 to 4 weight% is preferable, 0.4 to 3% by weight is particularly preferred.

  The fatty acid constituting the propylene glycol fatty acid ester of the component (e) or the sorbitan fatty acid ester of the component (f) is not particularly limited as long as it is a fatty acid originating from edible animal and vegetable fats and oils, such as caprylic acid, capric acid, Examples thereof include one or a mixture of two or more selected from the group of lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, erucic acid and the like. Preferably, one or more selected from the group of caprylic acid, capric acid and lauric acid is contained in an amount of about 50% by weight or more, preferably about 70% by weight or more, more preferably about 90% by weight or more based on the total fatty acid Fatty acids or fatty acid mixtures.

  Moreover, the coagulation preparation for tofu of this invention can contain (g) 1 type (s) or 2 or more types (henceforth (g) component) chosen from the group of saccharides, sugar alcohol, and a polyhydric alcohol.

  Examples of the saccharide used in the present invention include monosaccharides such as xylose, glucose and fructose, oligosaccharides such as sucrose, lactose and maltose, starch degradation products such as dextrin and starch syrup, maltotriose, maltotetraose, malto Examples include malto-oligosaccharides such as pentaose or maltohexaose, and preferably starch decomposition products such as dextrin or chickenpox.

  Examples of the sugar alcohol used in the present invention include sorbitol, mannitol, maltitol, or reduced starch syrup. Preferably, sorbitol or reduced starch syrup is used.

  Examples of the polyhydric alcohol used in the present invention include propylene glycol, glycerin, polyglycerin and the like, and preferably glycerin.

  The above component (g) can be used alone or as a mixture of two or more. Preferably, the polyhydric alcohol is used alone. The above-described component (g) may be a solution dissolved or mixed with a solvent such as water. When dissolved or mixed with a solvent, it varies depending on the saccharides used, but in the case of glycerin, for example, about 1 to 20 parts by weight, preferably about 2 to 15 parts by weight, more preferably about 1 to 15 parts by weight of water. About 5 to 10 parts by weight.

  Although content of the (g) component in the coagulation preparation for tofu of this invention is not specifically limited, For example, 1 to 20 weight%, Furthermore, 5 to 15 weight% is preferable.

  Water can be appropriately added to the tofu coagulation preparation of the present invention as necessary.

  Although the manufacturing method of the coagulation preparation for tofu of this invention is not specifically limited, The manufacturing method of the preferable coagulation preparation for tofu is illustrated below. For example, the polyglycerin condensed ricinoleic acid ester obtained by the production method of the present invention is added to propylene glycol fatty acid ester, and the mixture is heated to about 50 to 80 ° C, preferably about 60 to 70 ° C. While stirring the heated mixture, an inorganic salt coagulant (for example, magnesium chloride) and a glycerin-water mixed solution (for example, glycerin: water = about 9: 1) are sequentially added thereto, and then a high-speed rotating homogenizer or the like. Is used and stirred at a rotational speed of about 6000 to 20000 rpm for about 10 to 60 minutes to obtain a dispersion in which the inorganic salt coagulant is uniformly dispersed. The tofu coagulation preparation according to the present invention can be produced by atomizing the resulting dispersion preferably with a wet pulverizer or the like. The coagulation preparation for tofu of the present invention thus produced is a uniform and stable composition in which fine particles of inorganic salt coagulant (particle diameter of about 0.01 to 50 μm) are ultrafinely dispersed in a dispersion medium. obtain.

  The coagulation preparation for tofu according to the present invention is produced by mixing each component, but the apparatus for producing the coagulation preparation for tofu of the present invention is not particularly limited, and for example, a stirrer, a heating jacket or jammer. A normal stirring and mixing tank equipped with a plate or the like can be used. Examples of the stirrer used include a propeller stirrer, a homomixer (manufactured by Tokushu Kika Kogyo Co., Ltd.), a clear mix (manufactured by MTechnic Co., Ltd.), and the like, preferably a clear mix. The dispersion obtained by stirring with a stirrer is preferably further atomized with a wet pulverizer or the like. The wet pulverizer atomizes particles in the dispersion liquid using glass beads or zirconia beads filled in the pulverization chamber of the pulverizer as a dispersion medium. Examples of the wet pulverizer include a sand mill (manufactured by Shinto Kogyo Co., Ltd.), a bead mill (manufactured by Finetech Co., Ltd.), a dyno mill (manufactured by Swiss WAB Co.), and the like, and these can be preferably used.

  The maximum particle size of the ultrafine dispersed inorganic salt coagulant in the tofu coagulation preparation according to the present invention is preferably about 50 μm or less, more preferably about 40 μm or less, and still more preferably about 30 μm or less. By making the inorganic salt coagulant particles in the tofu coagulation preparation into fine particles, the other components in the tofu coagulation preparation are effectively adsorbed on the surface of the inorganic salt coagulant fine particles. As a result, when the tofu coagulation preparation of the present invention is added to and mixed with the soymilk during the production of tofu, the inorganic salt coagulant fine particles are uniformly dispersed in the soymilk, and the inorganic salt coagulant is added to the soymilk. Since the soymilk is solidified by gradually and uniformly dissolving in the tofu, the tofu with a fine and uniform texture of the inner phase of tofu and excellent texture of water retention can be obtained. In addition, precipitation of the inorganic salt coagulant itself is also suppressed.

  Further, in the coagulation preparation for tofu according to the present invention, a thickening stabilizer such as starch, agar or gelatin may be blended within a range not inhibiting the purpose of the present invention. Here, as starch, corn starch, potato starch, wheat starch, rice starch, sweet potato starch, tapioca starch, mung bean starch, sago starch, pea starch, or esterification treatment thereof (for example, acetate starch etc.), etherification treatment (For example, hydroxypropyl starch, etc.), cross-linked processing (for example, phosphoric acid cross-linked starch, etc.), oxidized starch (for example, dialdehyde starch, etc.) or processed starch that has been subjected to wet heat treatment alone or in combination. Can be mentioned.

  The amount of the coagulant preparation for tofu according to the present invention added to soy milk is preferably the amount of the inorganic salt coagulant in the coagulant preparation of the present invention that is usually used for soy milk, that is, the inorganic salt coagulant (in terms of anhydride). What is necessary is just to use in the range of about 0.05 to 0.5 weight%.

Example 1
[1] Production process of polyglycerin-condensed ricinoleic acid ester (I): 1200 g of ricinoleic acid was placed in a 2 liter four-necked flask equipped with a stirrer, thermometer, nitrogen introduction tube and dehydration condenser, and nitrogen was added at 60 ml / min. Then, the reaction was carried out at 210 ° C. for 6 hours while removing generated water under a reduced pressure of 53.3 kPa to obtain condensed ricinoleic acid. The obtained condensed ricinoleic acid was confirmed by GPC analysis to have a high molecular weight ratio of 1.9.
Step (II): In a 0.5 liter four-necked flask equipped with a stirrer, thermometer, nitrogen inlet tube, dehydration condenser tube, 40 g of hexaglycerin and 300 g of condensed ricinoleic acid obtained in step (I) (molar ratio) 3.0) Preparation, 0.6g of sodium hydroxide was introduced, nitrogen was introduced at 20ml / min, and the reaction was carried out at 190 ° C for 12 hours while removing the generated water under a reduced pressure of 53.3kPa to obtain polyglycerin condensed ricinoleic acid ester It was. The acid value of this product was 2 or less, and it was confirmed that it was esterified.

[2] Preparation of coagulated preparation The polyglycerin condensed ricinoleic acid ester obtained above was dissolved in corn oil at 80 ° C, and a 60 wt% magnesium chloride hexahydrate aqueous solution was added to the oil layer at 5000 rpm and temperature at the homomixer. After addition while emulsifying at 65 ° C., the rotational speed was set to 10000 rpm, and main emulsification was performed for 1 minute. Immediately after the completion of emulsification, the mixture was cooled to 5 ° C. and stored for 1 day and night at 5 ° C. to obtain an emulsion coagulation preparation.

[3] Production and evaluation of tofu Soymilk was Brix12 soymilk obtained by a conventional method using soybean binton. Use the metering pump so that the concentration of magnesium chloride in the soymilk becomes 0.3% by weight on the soymilk prepared at 80 ° C and pumped at 750g / min by the metering pump. Then, they were mixed in the line, and further mechanically dispersed at a rotational speed of 5000 rpm using a milder (manufactured by Ebara Seisakusho). 150 g of the dispersion treatment liquid was filled in a mold (8 cm × 7 cm × 3 cm (height)). The time from filling to the start of coagulation was measured, and this time was recorded as the coagulation start time of soy milk. Furthermore, after aging for 20 minutes after filling, it was stored overnight at 5 ° C. Moreover, about the internal phase of the obtained tofu, it cut with the cutter blade, and observed the cross section visually. The results are shown in Table 1.

Example 2
The same operation as in Example 1 was carried out except that the reaction time in step (I) of Example 1 was 19 hours and the reaction time in step (II) was 10 hours. The results are shown in Table 1.

Example 3
The same operation as in Example 1 was performed except that the reaction temperature in Step (I) of Example 1 was 190 ° C. and the reaction time was 12 hours. The results are shown in Table 1.

Example 4
The same operation as in Example 1 was performed except that the reaction temperature in Step (I) of Example 1 was 230 ° C. and the reaction time was 4 hours. The results are shown in Table 1.

Example 5
The same operation as in Example 1 was carried out except that in Step (II) of Example 1, 88.3 g of hexaglycerin was changed to 630 g of condensed ricinoleic acid (molar ratio 2.7). The results are shown in Table 1.

Example 6
The same operation as in Example 1 was carried out except that 59.5 g of hexaglycerin in Step (II) of Example 1 was changed to 654 g of condensed ricinoleic acid (molar ratio 4.2). The results are shown in Table 1.

Comparative Example 1
The same operation as in Example 1 was carried out except that the reaction time in step (I) of Example 1 was 1.5 hours and the reaction time in step (II) was 10 hours. The results are shown in Table 1.

  * Molar ratio: Condensed ricinoleic acid / polyglycerol molar ratio

Claims (5)

A polyglycerin condensed ricinol comprising a step (I) of obtaining a condensed ricinoleic acid by polycondensation reaction of ricinoleic acid and a step (II) of esterifying the condensed ricinoleic acid obtained in step (I) with polyglycerin. A method for producing an acid ester, wherein the condensed ricinoleic acid obtained in step (I) is a condensed ricinoleic acid having a high molecular weight ratio of 1 or more obtained from the following formula (1): Method.
High molecular weight ratio = S1 / S2 Formula (1)
S1: Peak area corresponding to a molecular weight distribution of 2000 or more in terms of polystyrene by gel permeation chromatography of condensed ricinoleic acid S2: Molecular weight in the molecular weight distribution of polystyrene by gel permeation chromatography of condensed ricinoleic acid of 100 Peak area equivalent to more than 2000   The method for producing a polyglycerol condensed ricinoleic acid ester according to product 1, wherein the reaction time of the polycondensation reaction of ricinoleic acid in step (I) is 2 to 20 hours.   The method for producing a polyglycerin condensed ricinoleic acid ester according to claim 1 or 2, wherein the polyglycerin condensed ricinoleic acid ester is used as an emulsifier for a coagulation preparation for tofu.   (A) One or more inorganic salts selected from the group consisting of polyglycerin condensed ricinoleic acid ester obtained by the production method according to any one of claims 1 to 3, (b) magnesium chloride, magnesium sulfate and calcium chloride A coagulation preparation for tofu containing a system coagulant.   The coagulation preparation for tofu according to claim 4, further comprising (c) an oil and fat.