JPH08245549A - Production of sulfonate - Google Patents

Abstract

PURPOSE: To efficiently obtain a high-purity sulfonate useful as an organic peracid precursor, etc., in high yield by reacting a prescribed ether carbonyl compound with a specific hydroxyalkanesulfonate under prescribed conditions. CONSTITUTION: An ether carbonyl compound of formula I [R<1> is H, a 1-10C alkyl, an alkenyl or an acyl; R<2> is a 1-8C alkylene or a (substituted) phenylene; R<4> is a 1-5C alkylene; (p) is 0 or 1; A is a 2-4C alkylene; (n) is 0-100; Y is hydroxy, a halogen or a 1-3C alkoxy] is reacted with a hydroxyalkanesulfonate of the formula HO-R<3> -SO3 M (R<3> is a 1-8C alkylene; M is an alkali metal, etc.) in a solventless state or in the presence of an inert organic solvent. The prepared reaction product is mixed with a solvent having 7.4-12.0 solubility parameter at <=100 deg.C boiling point such as methyl ethyl ketone and centrifuged to give the objective sulfonate of formula II.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a process for producing a sulfonate useful as an organic peracid precursor in a household bleaching agent such as a fungicide, a kitchen bleaching agent and a clothing bleaching agent.

[0002]

2. Description of the Related Art Conventionally, the problems to be solved by the invention
As a bleaching agent, a chlorine bleaching agent and an oxygen bleaching agent are known, but the former has a strong chlorine-based odor, irritation to eyes, skin, etc., and if used by mistake with an acidic detergent. There is a problem that toxic gas is generated. For this reason,
In recent years, such an oxygen-based bleaching agent which has no danger has been widely used. Then, in order to enhance the bleaching activity, a peroxide which produces a peracid in hydrogen peroxide or an aqueous solution is used in combination with a bleach activator or an organic peracid precursor. For example, JP-A-62-479
Japanese Patent Publication No. 4 discloses a composition in which hydrogen peroxide or sodium percarbonate, a bleaching activator and a peroxydisulfate are used in combination. As the bleach activator, for example, tetraacetylethylenediamine, tetraacetylglycoluril,
Pentaerythritol tetraacetate or the like is used.

However, since these bleach activators generate peracetic acid as a bleaching active species, they have a strong pungent odor and have many problems in practical use. In addition, JP-A-61-8
1498, JP-A-61-81499 and JP-A-63-152357, the general formula (a)

[0004]

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(In the formula, R ⁸ represents an alkyl group having 1 to about 14 carbon atoms, an aryl group or an alkanol group, and R ⁹ represents a hydrogen atom or an alkyl group having 1 to about 10 carbon atoms, an aryl group or an alkanol group. R ¹⁰ represents a group represented by an alkylene group having 1 to about 14 carbon atoms, an arylene group or an alkarylene group). ] The compound represented by the following is disclosed as an organic peracid precursor that can be used in a bleaching agent. However, in order to obtain a more excellent bleaching power, when the compound described in the above publication is used in a system in which hydrogen peroxide and the like and an organic peracid precursor are used at a high concentration, the organic peracid generated by perhydrolysis is phenol. Since it is consumed in the oxidation of sodium sulfonate, the expected effect cannot be obtained. Also, the above general formula
In the synthesis of the compound represented by (a), it is difficult to dehydrate esterification of an ordinary acid and alcohol, which is a problem in industrial implementation. Therefore, the present inventors have studied the organic peracid precursor, the following general formula (3)

[0006]

[Chemical 4]

[Wherein R ¹ is a hydrogen atom or has 1 carbon atom]
To a linear or branched alkyl group, an alkenyl group, or an acyl group having 10 to 10 carbon atoms, R ² is a linear or branched alkylene group having 1 to 8 carbon atoms, or a linear or branched chain having 1 to 5 carbon atoms. Represents an optionally substituted phenylene group, R ³ represents a linear or branched alkylene group having 1 to 8 carbon atoms, and R ⁴ represents a linear or branched chain having 1 to 5 carbon atoms. Represents an alkylene group, p represents a number of 0 or 1, A represents an alkylene group having 2 to 4 carbon atoms, n represents a number of average added moles of alkylene oxide and is a number greater than 0 and 100 or less, n The individual A's may be the same or different. M represents an alkali metal atom, an alkaline earth metal atom, ammonium, alkylammonium or alkanolammonium. ], And a patent application has already been made (Japanese Patent Application No. 5-182497). However, since the reaction end product when obtaining this sulfonate is a fine crystal, there is a problem in purification and separation, and it is an industrial scale. Was difficult to manufacture. In addition, the obtained product was unsatisfactory in terms of purity because it contained many impurities. Moreover, when the reaction is carried out without a solvent, the fluidity is low, and it is difficult to produce it on an industrial scale, and there is a problem that an odor remains in the product when an inert organic solvent is added to increase the fluidity. Yes, research was being conducted.

Therefore, an object of the present invention is to produce a sulfonate which can remove impurities and odor components and can efficiently produce a high-quality sulfonate represented by the general formula (3) on an industrial scale. To provide the law.

[0009]

[Means for Solving the Problems] As a result of intensive investigations conducted by the present inventors in such an actual situation, an ether carbonyl compound and a hydroxyalkane sulfonate are reacted in the presence of a solvent-free or inert organic solvent to give a compound of the general formula (3) When producing the sulfonate represented by, in the reaction product obtained,
The present invention has been completed by finding that the above problems can be solved by adding a solvent having a solubility parameter of 7.4 to 12.0 and a boiling point of 100 ° C. or less and centrifuging. That is, the present invention, the following general formula (1)

[0010]

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[In the formula, R ¹ , R ² , R ⁴ , p, A and n have the above-mentioned meanings, and Y represents a hydroxy group, a halogen atom or an alkoxy group having 1 to 3 carbon atoms. And ether carbonyl compound represented by] the following general formula ^{(2) HO-R 3 -SO} 3 M (2) wherein, R ³ and M have the same meanings as defined above. ] The hydroxyalkane sulfonate represented by the following is reacted in the presence of a solvent-free or inert organic solvent, to the resulting reaction product, a solvent having a solubility parameter of 7.4 to 12.0 and a boiling point of 100 ° C or less is added. The present invention provides a method for producing a sulfonate represented by the general formula (3), characterized by performing centrifugation.

The present invention will be described in detail below. In the sulfonate represented by the general formula (3) of the present invention, as the linear or branched alkyl group or alkenyl group having 1 to 10 carbon atoms represented by R ¹ , methyl, ethyl, propyl, butyl, pentyl, Examples thereof include groups such as isopropyl, isobutyl, isopentyl, octyl and nonyl. Examples of the acyl group represented by R ¹ include groups such as acetyl, propionyl, butyryl and valeryl. Among these groups represented by R ¹ , a hydrogen atom is particularly preferable.

As the linear or branched alkylene group having 1 to 8 carbon atoms represented by R ² or the phenylene group which may be substituted with a linear or branched alkyl group having 1 to 5 carbon atoms, , Methylene, ethylene, propylene, ethylethylene, trimethylene, tetramethylene, hexamethylene, heptamethylene, octamethylene, 1,2-phenylene, 1,4-phenylene, 2-methyl-1,4-phenylene, 2-ethyl- 1,4-phenylene, 2-propyl-1,4-phenylene, 2-butyl-1,4-phenylene,
2-heptyl-1,4-phenylene, 2- (1-methylethyl) -1,4-phenylene, 2- (1-methylpropyl) -1,4-phenylene, 2- (2-methylbutyl)-
Examples include groups such as 1,4-phenylene. Of these groups represented by R ² , a methylene group is particularly preferable.

Examples of the linear or branched alkylene group having 1 to 8 carbon atoms represented by R ³ include methylene, ethylene, propylene, ethylethylene, trimethylene, tetramethylene, hexamethylene, heptamethylene, octamethylene and the like. Groups. Among these groups represented by R ³ , a linear or branched alkylene group having 1 to 4 carbon atoms is particularly preferable.

Examples of the linear or branched alkylene group having 1 to 5 carbon atoms represented by R ⁴ include groups such as methylene, ethylene, propylene and tetramethylene.
Is 0 or 1, but p = 0 is preferred. Examples of the alkylene group having 2 to 4 carbon atoms represented by A include groups such as ethylene, propylene, trimethylene and tetramethylene, and ethylene or propylene is particularly preferable. Also, n
Is a number greater than 0 and 100 or less indicating the average number of moles of alkylene oxide added, and 0 <n ≦ 5 is preferable.

Examples of the alkali metal atom represented by M include sodium atom and potassium atom, examples of the alkaline earth metal atom include magnesium atom and calcium atom, and examples of the alkylammonium include methylammonium. , Diethylammonium and the like, and examples of the alkanolammonium include monoethanolammonium, triethanolammonium and the like. Among these groups represented by M, an alkali metal atom is particularly preferable.

The general formula representing the sulfonate of the present invention
In (3), the n oxyalkylene groups (AO) may be one kind of oxyalkylene group or a combination of different oxyalkylene groups. Specifically, a polyoxyethylene group, a polyoxypropylene group, a polyoxyethylene-polyoxypropylene group and the like can be mentioned.

Further, in the ether carbonyl compound represented by the general formula (1) used in the production method of the present invention, the halogen atom represented by Y is a chlorine atom, a fluorine atom, a bromine atom, an iodine atom or the like. As the alkoxy group having 1 to 3 carbon atoms, methoxy, ethoxy,
Examples include groups such as propoxy. Among these groups represented by Y 1, a hydroxy group is particularly preferable.

The general formula (1), which is a raw material for the production method of the present invention,
As an ether carbonyl compound represented by, for example,

[0020]

[Chemical 6]

An organic acid such as or a mixed acid thereof, an acid halide of the above organic acid or a mixture thereof, a lower alcohol ester of the above organic acid or a mixture thereof, and the like are used. Among these ether carbonyl compounds (1), the compounds represented by the general formula (1-1) are particularly preferable.

[0022]

[Chemical 7]

[In the formula, A has the same meaning as described above, n'is a number greater than 0 and 5 or less, which represents the average number of moles of alkylene oxide added, and n'number of A may be the same or different. good. These ether carbonyl compounds (1) can be obtained by any method, but in the case of an organic acid (1-a) in which Y is a hydroxy group in the general formula (1), for example, It can be obtained by reacting the corresponding glycol ether salt (4) with the halogen compound (5) according to the reaction formula.

[0024]

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[In the formula, R ¹ , R ² , R ⁴ , A, M, n and p have the same meanings as described above, and X represents a halogen atom. Further, in the general formula (1), the acid halide (1-b) in which Y is a halogen atom and the lower alcohol ester (1-c) in which Y is an alkoxy group having 1 to 3 carbon atoms are the organic compounds obtained above. It can be produced from the acid (1-a) by a known method.

Examples of the hydroxyalkanesulfonate represented by the general formula (2) used in the production method of the present invention include 2-hydroxyethanesulfonic acid (isethionic acid) and 2-hydroxypropane-1-sulfone. Acids, 1-hydroxypropane-2-sulfonic acid, 1-hydroxybutane-2-sulfonic acid, 2-hydroxypentane-1-sulfonic acid, and the like, hydroxyalkanesulfonic acid sodium salts, potassium salts, calcium salts, ammonium salts, Examples thereof include methylammonium salt, diethylammonium salt and triethanolammonium salt.

In the production method of the present invention, the ether carbonyl compound (1) is a hydroxyalkane sulfonate (2)
It is preferable to react 0.5 to 3 mol, particularly 0.8 to 2 mol per mol. A solvent is not always necessary for this reaction, but it can be used. As the solvent used here, any solvent may be used as long as it is inert to the raw materials and the reaction product, and particularly forms a azeotropic mixture with water for the reaction with the organic acid (1-a). An inert organic solvent that facilitates the dehydration action is preferable. Examples of such an inert organic solvent include inert solvents such as benzene, cyclohexane, toluene, mesitylene, xylene, ethylbenzene and monochlorobenzene, and these can be used alone or in combination. Among these, xylene, because solid-liquid separation is easy,
Toluene, mesitylene and benzene are preferred. The reaction temperature is preferably 70 to 250 ° C, particularly preferably 80 to 220 ° C.

The reaction in the production method of the present invention proceeds sufficiently even without using a catalyst, but the reaction can be carried out more efficiently by using the esterification reaction catalyst which is usually used in the esterification reaction. . Among such esterification reaction catalysts, examples of acidic catalysts include sulfuric acid, hydrochloric acid, and paratoluenesulfonic acid, and examples of basic catalysts include alkali metal hydroxides and alkali metal alcoholates. The amount of these esterification reaction catalysts used is preferably about 0.1 to 5% by weight based on the entire reaction system.

Further, the progress of the reaction in the production method of the present invention can be confirmed by measuring the amount of water or alcohol distilled out of the system. The desired sulfonate represented by the general formula (3) in the reaction mixture is obtained as fine crystals, and solid-liquid separation takes a very long time by simple filtration, and the obtained product has many impurities and a high purity. I am not satisfied with it. Moreover, when the reaction is carried out without a solvent, the fluidity is low, and it is difficult to produce it on an industrial scale.
The addition of an inert organic solvent to increase flowability leaves an odor in the product. Therefore, in the present invention, a solvent having a solubility parameter of 7.4 to 12.0 and a boiling point of 100 ° C. or less is added to the obtained reaction product, and centrifugation is performed.

The solvent having a solubility parameter of 7.4 to 12.0 and a boiling point of 100 ° C. or less used in the present invention is preferably an ether solvent or a ketone solvent, and examples thereof include methyl ether, ethyl ether, acetone and methyl ethyl ketone. Solubility parameter 7.4 ~
If a solvent having a boiling point of 12.0 and a boiling point higher than 100 ° C. is used, the subsequent drying step is time consuming and not economical. The addition amount of the solvent having a solubility parameter of 7.4 to 12.0 and a boiling point of 100 ° C. or lower is preferably 30 to 500% by weight with respect to the reaction product. If it is less than 30% by weight, impurities and odorous components cannot be sufficiently removed, and if it exceeds 500% by weight, it is not economical. Solvents with solubility parameters below 7.4 or above 12.0
Impurities and odor components cannot be removed sufficiently. The centrifuge used in the present invention is preferably a centrifugal settler, for example, a decanter type or a separation plate type. Further, it may be either a batch type or a continuous type.

In the present invention, the cake obtained by centrifugation has a solubility parameter of 7.4 to 12.0 and a boiling point of 100.
It is preferable to wash or reslurry with a solvent at a temperature of not higher than ° C. When washing the cake obtained by centrifugation, it is preferable to use a decanter type centrifugal separator, for example, a decanter equipped with a washing device. The amount of the solvent having a solubility parameter of 7.4 to 12.0 and a boiling point of 100 ° C. or less used for washing is preferably 50 to 500% by weight based on the solid content of the cake obtained by centrifugation. 50
Impurities and odorous components cannot be sufficiently removed if it is less than 5% by weight, and it is not economical if it exceeds 500% by weight. In the case of a decanter, the cake obtained by centrifugation has a solubility parameter of 7.4 to 12.0 and a boiling point of 100 ° C until it becomes fluid.
The following solvents may be added (within the above range) and washed in a decanter.

The condition of centrifugation is not particularly limited as long as solid-liquid separation of the reaction product can be completed, but 1000 to 5000 G is preferable. The number of times of washing is not particularly limited as long as impurities and odorous components can be removed, but it is preferable to repeat 1 to 5 times from an economical viewpoint. By washing, unreacted raw materials, by-products, and odor components can be efficiently removed, and high-quality sulfonate can be obtained.

Examples of the by-products present in the reaction product include compounds represented by the following formula (6) in which the ether carbonyl compound (1) is reacted with the unreacted raw material.

[0034]

[Chemical 9]

[In the formula, R ¹ , R ² , R ⁴ , A, n and p have the same meanings as described above. Further, examples of the odor component include solvent odor derived from the inert organic solvent used in the reaction.

When the cake obtained by centrifugation is reslurried, it is preferable to use a decanter type or a separation plate type as the centrifugal separator. The method of reslurrying is not particularly limited, but the cake obtained by centrifugation in a general tank and the solubility parameter of 7.4 to 12.0 and the boiling point of 100
A method of adding a solvent at a temperature of ℃ or less and mixing with a stirrer is preferable. Solubility parameter used for reslurry 7.4-12.0
The amount of the solvent having a boiling point of 100 ° C. or lower is preferably 50 to 500% by weight based on the solid content of the cake obtained by centrifugation. If it is less than 50% by weight, impurities and odorous components cannot be sufficiently removed, and if it exceeds 500% by weight, it is not economical. The condition of centrifugation is not particularly limited as long as solid-liquid separation of the reaction product can be completed, but 1000 to 5000 G is preferable. The number of reslurry is not particularly limited as long as impurities and odor components can be removed, but it is preferable to repeat 1 to 5 times from an economical viewpoint.

After such centrifugation, the cake is dried to obtain the sulfonate represented by the general formula (3) in powder form. The method for drying the cake is not particularly limited, but vacuum drying is preferable in order to efficiently remove the remaining solvent having a solubility parameter of 7.4 to 12.0 and a boiling point of 100 ° C or less. The vacuum dryer is not particularly limited as long as sulfonate can be obtained in powder form, but a batch type box dryer, a groove type agitation dryer and the like are preferable. The drying conditions are not particularly limited as long as the solvent having a remaining solubility parameter of 7.4 to 12.0 and a boiling point of 100 ° C. or less can be removed, and the drying temperature and the drying vacuum degree may be changed during the drying. After drying, it may be pulverized with a general pulverizer depending on the case.

[0038]

Industrial Applicability According to the method of the present invention, the sulfonate represented by the general formula (3), which is useful as an organic peracid precursor, is efficiently removed on an industrial scale, and impurities and odor components are removed.
It can be manufactured with high purity.

[0039]

The present invention will be described in more detail below with reference to examples, but the present invention is not limited thereto.

Example 1 In a 300-liter GL reaction vessel equipped with a stirrer, a thermometer, a nitrogen blowing tube and a reflux condenser equipped with a water separator, 2 mol of ethylene oxide was added on average, and the following formula (7) was used.

[0041]

[Chemical 10]

48 kg of compound represented by (average molecular weight 240)
(200 mol) and 44% aqueous sodium isethionate 60
Then, kg (180 mol) was charged, 3.8 kg (20 mol) of paratoluenesulfonic acid monohydrate as a catalyst and 48 kg of xylene (solvent azeotropic with water) as a solvent were charged, and heated under a nitrogen atmosphere while stirring. From around 100 ° C., water derived from sodium isethionate and xylene were distilled out, so water was taken out from the water separator and xylene was refluxed. When heated further to approximately 140 ° C, water of reaction and xylene are distilled off. The temperature was controlled at 140 to 143 ° C., and the reaction was carried out until the acid value of the reaction solution became 15 or less. After that, it was cooled to 70 ° C and the esterified product was extracted from the reaction tank.
It was g.

After adding 56 kg of acetone (solubility parameter = 9.9) to 100 kg of the obtained esterified product and mixing,
Centrifugation (centrifugation effect: 3000 G) was performed using a decanter (ZIL type manufactured by Tanabe Wiltech Co., Ltd.) to obtain 43.07 kg of cake.
Acetone (56 kg) was added to the cake, the mixture was reslurried and then centrifuged (3000 G) in a decanter to obtain 35.97 kg of cake. After adding 56 kg of acetone to this cake and reslurrying, centrifuging (3000 G) with a decanter to give 33.97 kg of cake.
I got After adding 56 kg of acetone to this cake and reslurrying, centrifuge (3000 G) with a decanter to make cake 3
I got 2.08kg. This cake in a 100 liter kneader
After drying for 8.5 hours (40 to 80 ° C / 20 to 80 Torr: static drying + mixed drying), 22.0 kg of a sulfonate represented by the following formula (8) was obtained.

[0044]

[Chemical 11]

Example 2 In the same manner as in Example 1, except that the reslurry was cake washed and the decanter was a decanter equipped with a washing device, the above formula was used.
21.8 kg of sulfonate represented by (8) was obtained.

Example 3 To a 1-liter GL reactor equipped with a stirrer, a thermometer, a nitrogen blowing tube and a reflux condenser equipped with a water separator, 1.5 mol of ethylene oxide was added on average, and the following formula (9) was used.

[0047]

[Chemical 12]

232.0 g (1.0 mol) of a compound represented by the formula (average molecular weight 218.5, purity 94.2%) and 177.7 g (1.2 mol) of sodium isethionate were charged, and 22.8 g (0.12) of paratoluenesulfonic acid monohydrate was used as a catalyst. Mol) and 232.0 g of xylene as a solvent, and the mixture was heated with stirring under a nitrogen atmosphere. Since water and xylene were distilled off from around 115 ° C., water was taken out from the water separator and xylene was refluxed. When heated to about 140 ° C, water of reaction and xylene are distilled off. Temperature control at 140-143 ℃,
The reaction was carried out until the acid value of the reaction solution became 15 or less. Then, it cooled to 70 degreeC and obtained the esterification thing. To this esterified product, 232 g of acetone was added and mixed, followed by centrifugation (centrifugal effect: 3000 G / 3 minutes) to obtain 411 g of cake. After adding 800 g of acetone to this cake and reslurrying,
After centrifugation (centrifugal effect 3000G / 3 minutes), cake 390
g was obtained. This cake was dried in a vacuum dryer (80 ° C, 500 Torr)
After drying for 24 hours and crushing with a mixer, the following formula
286 g of sulfonate represented by (10) was obtained.

[0049]

[Chemical 13]

Example 4 An esterified product was obtained in the same manner as in Example 1, and 90.0 g of methyl ether (solubility parameter = 8.8) was added to 30.1 g of the obtained esterified product and mixed, followed by centrifugation (centrifugal effect 3000 G / For 3 minutes) to obtain 17.4 g of cake. 17.4 g of this cake was dried for 12 hours in a vacuum dryer (80 ° C., 500 Torr) and pulverized with a mixer to obtain 13.9 g of the sulfonate represented by the above formula (8).

Comparative Example 1 An esterified product was obtained in the same manner as in Example 1, and 30.1 g of the obtained esterified product was mixed with hexane (solubility parameter 7.3).
After adding 90.0 g and mixing well, pressurizing filter (membrane area 0.00159
charged in m ^2), filtration pressure = 2 kg / cm ^2, filtration temperature = room temperature, subjected to pressure filtration through a filter agent = filter paper (No.2), cake 18.1g
I got 18.1g of this cake was dried under reduced pressure (80 ℃, 500 To
rr) and dried for 12 hours, and pulverized with a mixer to obtain 14.5 g of the sulfonate represented by the above formula (8).

Comparative Example 2 22.0 kg of the sulfonate represented by the above formula (8) was obtained in the same manner as in Example 1 except that acetone was changed to hexane (solubility parameter = 7.3).

The purity, odor and powderiness of the sulfonates obtained in Examples 1 to 4 and Comparative Examples 1 and 2 were evaluated by the following methods. The results are shown in Table 1. <Purity> The purity of the sulfonate was calculated from the following formula by analyzing the acid value and saponification value of the dry powder. Purity of sulfonate (%) = (acid value-saponification value) x 10 ^-3 x
370 / 56.11 × 100 <Odor> The odor of sulfonate was evaluated by the panelists according to the following criteria : Evaluation criteria ◎: Very good ○: Good △: Slightly bad ×: Poor <Powderability> Powderiness of sulfonate Is the evaluation criteria in which the state of the dry powder is visually evaluated and evaluated according to the following criteria ◎: Very good (dry) ○: Good (dull feeling) Δ: Somewhat bad (somewhat sticky) ×: Poor (adhesive) Big)

[0054]

[Table 1]

Claims (3)

[Claims] 1. The following general formula (1): [In the formula, R ¹ represents a hydrogen atom, or a linear or branched alkyl group, an alkenyl group, or an acyl group having 1 to 10 carbon atoms, and R ² represents a linear or branched alkylene group having 1 to 8 carbon atoms. A group, or a phenylene group which may be substituted with a linear or branched alkyl group having 1 to 5 carbon atoms, R ⁴ represents a linear or branched alkylene group having 1 to 5 carbon atoms,
p represents a number of 0 or 1, A represents an alkylene group having 2 to 4 carbon atoms, n represents a number of average added moles of alkylene oxide, is a number greater than 0 and 100 or less, and n A's are the same. But it can be different. Y represents a hydroxy group, a halogen atom or an alkoxy group having 1 to 3 carbon atoms. And ether carbonyl compound represented by] the following general formula ^{(2) HO-R 3 -SO} 3 M (2) wherein, R ³ is an alkylene group of a straight-chain or branched-chain having 1 to 8 carbon atoms In the formula, M represents an alkali metal atom, an alkaline earth metal atom, ammonium, alkylammonium or alkanolammonium. ] The hydroxyalkane sulfonate represented by the following is reacted with a solvent-free or in the presence of an inert organic solvent, the resulting reaction product, a solvent having a solubility parameter of 7.4 to 12.0 and a boiling point of 100 ℃ or less. In addition, a general formula (3), characterized by performing centrifugation, (In the formula, R ¹ , R ² , R ³ , R ⁴ , A, M, p and n have the above-mentioned meanings.) A process for producing a sulfonate. 2. The cake obtained by centrifugation is boiled at a boiling point of 100 ° C.
Washing with the following solvent, The manufacturing method of the sulfonate of Claim 1 characterized by the above-mentioned. 3. The cake obtained by centrifugation is boiled at a boiling point of 100 ° C.
The reslurry is performed with the following solvent.
A method for producing the sulfonate described.