Method for manufacturing a sulfonate composition

Abstract

The present invention provides a method for producing a sulfonate composition, which comprises the following operations: reacting (C) a sulfonating agent with a diester of a specified unsaturated carboxylic acid [hereinafter referred to as component (A)] in the presence of at least one solvent selected from (B) (B1) an organic solvent [hereinafter referred to as component (B1)] and (B2) water [hereinafter referred to as component (B2)] to obtain a mixture containing a specified sulfonate having a diester structure [hereinafter referred to as component (S)]; and an operation of removing insoluble components from the mixture. In the mixture to which the removal of insoluble components is applied, the content of component (B1) is 0.05 or more and 0.65 or less, and the content of component (B2) is 0.03 or more and 0.26 or less, relative to the total content of component (S), component (B1) and component (B2).

Description

Technical Field

[0001] The present invention relates to a method for manufacturing a sulfonate composition. Background Art

[0002] Regarding sulfonates such as sulfosuccinates, there are sulfonates used as anionic surfactants, which are used alone or in combination with other components as main cleaning agents, emulsifiers, wetting agents, dispersants, etc. in various fields.

[0003] In U.S. Patent Application Publication No. 2007 / 0214999, a compound and a composition containing the compound and a specified organic solvent are disclosed. The compound is a compound containing a salt of a mono- and / or diester of a sulfonated dicarboxylic acid, the dicarboxylic acid contains 4 to 8 carbon atoms, and the alkyl group is an alkyl group derived from 2-propylheptanol.

[0004] In Japanese Patent Application Laid-Open No. 2002-224552, an emulsifying dispersant is disclosed, which is formed by using two or more anionic surfactants (A) selected from sulfate esters (A1), sulfosuccinates (A2), ether carboxylates (A3), and phosphate esters (A4) of specified aliphatic alcohol alkylene oxide adducts.

[0005] In Japanese Patent Application Laid-Open No. Hei 9-500884, a liquid composition is disclosed, which is characterized in that it contains a diester of sulfosuccinic acid represented by a specific formula in water as a solvent or co-solvent, and the co-solvent is a polymer containing an alkylene oxide unit that is liquid at 10°C.

[0006] In Japanese Patent Application Laid-Open No. Hei 8-337567, a method for manufacturing a sulfosuccinate is disclosed. In this manufacturing method, an inorganic acid salt or an organic acid salt is added to an aqueous solution of a sulfosuccinate, the aqueous solution is heated and then cooled to remove the precipitate.

[0007] In Japanese Patent Application Laid-Open No. 2018-162446, a method for manufacturing a surfactant composition is disclosed. In this manufacturing method, there is a step of converting an esterified product (C) of an unsaturated dicarboxylic acid (c1) having 4 to 22 carbon atoms and a fatty acid monoalcohol (c2) having 1 to 22 carbon atoms into a sulfonated product (E) using a sulfonating agent (D). Summary of the Invention

[0008] Problems to be Solved by the Invention

[0009] From the viewpoints of forming extremely fine bubbles when used in an aqueous solution, having desired bubble characteristics such as rapid defoaming, and having high detergency against solid fat stains, etc., sulfonates of the diester type having an alkyl and / or alkenyl group with a specified number of carbon atoms are considered to be highly valuable surfactants.

[0010] Sulfonates are generally produced using an aqueous reaction medium and obtained as a reaction product containing water. Considering distribution costs and the like, it is desirable to reduce water and other components from the reaction product and to increase the concentration of the sulfonate composition as the main component to a certain extent for use in the preparation of secondary products. For these reasons, it is preferred that the sulfonate in the sulfonate composition has a high purity, and there is a need to provide a technology for a sulfonate composition with a low content of components other than sulfonate (such as inorganic salts, etc.).

[0011] The present invention provides a sulfonate composition containing a diester-type sulfonate having an alkyl group and / or alkenyl group with a specified number of carbon atoms and having a low content of inorganic metal compounds such as inorganic salts.

[0012] The present invention relates to a method for producing a sulfonate composition, which comprises the following operations: reacting (C) a sulfonating agent (hereinafter referred to as component (C)) with (A) a compound represented by the following general formula (1) (hereinafter referred to as component (A)) in the presence of one or more solvents selected from (B) (B1) an organic solvent (hereinafter referred to as component (B1)) and (B2) water (hereinafter referred to as component (B2)) (hereinafter referred to as component (B)) to obtain a mixture containing (S) a sulfonate represented by the following general formula (2) (hereinafter referred to as component (S)); and an operation of removing insoluble components from the above mixture,

[0013] The mixture to which the above insoluble component removal is applied contains component (S), component (B1), and component (B2), and the mass ratio (B1) / (S + B1 + B2) of the content of component (B1) to the total content of component (S), component (B1), and component (B2) is 0.05 or more and 0.65 or less,

[0014] The mass ratio (B2) / (S + B1 + B2) of the content of component (B2) to the total content of component (S), component (B1), and component (B2) is 0.03 or more and 0.26 or less.

[0015] ROOC-(CH2) n -CH=CH-(CH2) m -COOR’ (1)

[0016] (In the formula, R and R’ are independently groups selected from an alkyl group having 10 carbon atoms and an alkenyl group having 10 carbon atoms. n and m are each a number of 0 or more and 18 or less, and the sum of n and m is 0 or more and 18 or less.)

[0017] ROOC-(CH2) p -CH(SO3M)-CH2-(CH2) q -COOR’(2)

[0018] (In the formula, M is a cation, and R and R’ are independently groups selected from an alkyl group having 10 carbon atoms and an alkenyl group having 10 carbon atoms. p and q are each a number of 0 or more and 18 or less, and the sum of p and q is 0 or more and 18 or less.)

[0019] According to the method for producing a sulfonate composition of the present invention, a sulfonate composition containing a diester-type sulfonate having an alkyl group and / or an alkenyl group with a specified number of carbon atoms and having a low content of inorganic metal compounds such as inorganic salts can be obtained.

[0020] The method for producing a sulfonate composition of the present invention is suitable for producing a sulfonate composition that contains a diester-type sulfonate having an alkyl group and / or an alkenyl group with a specified number of carbon atoms at a high concentration and has excellent storage stability. Detailed Description

[0021] The inventors conducted in-depth research to solve the above problems, and as a result, invented a method for producing a sulfonate composition having a low content of inorganic metal compounds in the sulfonate. According to the production method of the present invention, a sulfonate composition having a low content of inorganic metal compounds in the sulfonate can be obtained. In addition, the inventors conducted in-depth research and found that the storage stability of the sulfonate composition is affected by an increase in the content of inorganic metal compounds such as inorganic salts in the sulfonate composition. It should be noted that a composition containing a sulfonate at a high concentration and having a low content of inorganic metal compounds such as inorganic salts can also obtain derived effects such as excellent low-temperature stability when incorporated into a cleaning agent composition, thereby broadening the degree of freedom in formulation.

[0022] Generally, sulfonates are produced through a reaction of sulfonating the compound represented by the above general formula (1). In this reaction, a mixture containing a sulfonate is obtained, and an operation of removing insoluble components such as inorganic salts from the mixture is performed.

[0023] It is presumed that in the present invention, when removing insoluble components from the mixture containing a sulfonate, by making the contents of (B1) an organic solvent and (B2) water in the mixture to be subjected to the removal of insoluble components fall within a specified range, the precipitation of inorganic metal compounds such as inorganic salts from the mixture can be promoted. Moreover, it is presumed that by subjecting the mixture in which a large amount of inorganic metal compounds such as inorganic salts have precipitated to the removal of insoluble components, the content of inorganic metal compounds such as inorganic salts in the mixture after the insoluble components have been removed becomes small.

[0024] The present invention relates to a method for manufacturing a sulfonate composition. In this manufacturing method, the following operations are carried out, that is, in the presence of one or more solvents [hereinafter referred to as component (B)] selected from (B1) an organic solvent [hereinafter referred to as component (B1)] and (B2) water [hereinafter referred to as component (B2)], a sulfonating agent (C) [hereinafter referred to as component (C)] is reacted with a compound represented by the general formula (1) (A) [hereinafter referred to as component (A)] under specified conditions to obtain a mixture containing the sulfonate (S) represented by the above general formula (2) [hereinafter referred to as component (S)]; and the operation of removing insoluble components from the mixture. The insoluble components are, for example, solids in the mixture. The solid may be a solid that exists without dissolving in the mixture or a solid that precipitates from the mixture by an operation carried out after the step of obtaining the mixture.

[0025] First, component (A), component (B), and component (C) used as raw materials in the sulfonation reaction of component (A) will be described.

[0026] Component (A) is a compound represented by the following general formula (1).

[0027] ROOC-(CH2) n -CH=CH-(CH2) m -COOR’ (1)

[0028] (In the formula, R and R’ are independently groups selected from an alkyl group having 10 carbon atoms and an alkenyl group having 10 carbon atoms. n and m are each a number of 0 or more and 18 or less, and the sum of n and m is 0 or more and 18 or less.)

[0029] R and R’ are independently groups selected from an alkyl group having 10 carbon atoms and an alkenyl group having 10 carbon atoms. From the viewpoint of cleaning performance, R and R’ are preferably independently groups selected from a branched alkyl group having 10 carbon atoms and a branched alkenyl group having 10 carbon atoms, and more preferably a branched alkyl group having 10 carbon atoms. Examples of the alkyl group having 10 carbon atoms include n-decyl, isodecyl, 2-propylheptyl, 4-methyl-2-propylhexyl, and 5-methyl-2-propylhexyl. Examples of the alkenyl group having 10 carbon atoms include n-decenyl and isodecenyl. From the viewpoint of cleaning performance, R and R’ are further preferably independently groups selected from 2-propylheptyl, 4-methyl-2-propylhexyl, and 5-methyl-2-propylhexyl.

[0030] n and m are each 0 or more, and may be 18 or less, 16 or less, 12 or less, 8 or less, 4 or less, 2 or less, 1 or less, 0. In addition, the sum of n and m is 0 or more, and may be 18 or less, 16 or less, 12 or less, 8 or less, 4 or less, 2 or less, 1 or less, 0.

[0031] In the present invention, one or more than two components (A) can be used. In the method for producing the sulfonate composition of the present invention, from the viewpoint of the detergency of the sulfonate composition [hereinafter referred to as the sulfonate composition of the present invention] obtained by the method for producing the sulfonate composition of the present invention, it is preferable to use a compound in which one or both of R and R' are 2-propylheptyl as the component (A).

[0032] From the viewpoints of the permeability, detergency, and compounding stability of the sulfonate composition of the present invention, the component (A) is preferably an ester of an unsaturated dicarboxylic acid having 4 or more and 22 or less carbon atoms. For example, it is preferably a diester of maleic acid, fumaric acid, citraconic acid, mesaconic acid, 2-pentenedioic acid, methylene succinic acid, allyl malonic acid, isopropylidene succinic acid, 2,4-hexadienedioic acid, or acetylenedicarboxylic acid, and more preferably a diester of maleic acid and fumaric acid.

[0033] The component (B) is a solvent. The component (B) is a solvent containing one or more selected from the component (B1) and the component (B2).

[0034] The component (B1) is an organic solvent. As the component (B1), at least one selected from monohydric alcohols and polyhydric alcohols can be mentioned. Considering the use of the sulfonate composition of the present invention, for example, as a raw material for manufacturing household products, the component (B1) is preferably a compound with less odor, and is also preferably a compound recognized as a food additive, a cosmetic raw material, etc.

[0035] The carbon number of the monohydric alcohol can be 1 or more and 12 or less. Examples of the monohydric alcohol include methanol, ethanol, 1-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-octanol, 1-nonanol, 2-nonanol, 5-nonanol, 1-decanol, 1-dodecanol, 3,5,5-trimethylhexan-1-ol, 2,6-dimethyl-4-heptanol, 2-propylheptanol, 4-methyl-2-propylhexanol, 5-methyl-2-propylhexanol, etc. From the viewpoints of the uniformity of appearance and use as a general raw material, the monohydric alcohol is preferably a compound selected from ethanol, 1-butanol, and 1-propanol, and more preferably ethanol.

[0036] The carbon number of the polyhydric alcohol can be 2 or more and 12 or less. The polyhydric alcohol can be 2 or more and 6 or less. Examples of the polyhydric alcohol include ethylene glycol, propylene glycol, 1,3-butanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,10-decanediol, diethylene glycol, triethylene glycol, tetraethylene glycol, dipropylene glycol, tripropylene glycol, glycerol, xylitol, sorbitol, etc. From the viewpoints of the uniformity of appearance and use as a general raw material, the polyhydric alcohol is preferably a compound selected from propylene glycol and glycerol, and more preferably propylene glycol.

[0037] From the viewpoints of appearance uniformity and use as a general raw material, the component (B1) is preferably a compound selected from ethanol, 1-butanol, 1-propanol, glycerin, and propylene glycol, and more preferably a compound selected from ethanol and propylene glycol.

[0038] The component (B2) is water. The component (B2) is preferably water that has been moderately purified without containing impurities. Well water or industrial water can also be used. From the viewpoint of the appearance of the sulfonate composition of the present invention, water with few impurities and hardness components is preferably used. Examples of the component (B2) include tap water, purified water, and ion-exchanged water, and ion-exchanged water is preferred.

[0039] The component (C) is a sulfonating agent. The component (C) can be used without particular limitation as long as it is a substance capable of adding to the double bond of the compound represented by the general formula (1) to carry out sulfonation. The component (C) is, for example, one or more compounds selected from sulfites (M2SO3 (M: cation)), bisulfites (MHSO3 (M: cation)), and metabisulfites (M2S2O5 (M: cation)). The component (C) is preferably an inorganic sulfate selected from bisulfites and metabisulfites, and more preferably an inorganic sulfate selected from metabisulfites. The cation (M) of the component (C) can be a monovalent cation such as sodium, potassium, or ammonium ion, or a divalent cation such as magnesium or calcium.

[0040] From the viewpoints of ease of operation and obtaining a high-quality and high-content sulfonate composition, the component (C) is preferably a sulfite such as ammonium sulfite, potassium sulfite, or sodium sulfite, a bisulfite such as ammonium bisulfite, potassium bisulfite, or sodium bisulfite, or a metabisulfite such as potassium metabisulfite or sodium metabisulfite. From the same viewpoint, as the salt, a sodium salt or a potassium salt is preferred, and a sodium salt is more preferred. From the same viewpoint, the component (C) is preferably sodium metabisulfite or potassium metabisulfite, and more preferably sodium metabisulfite.

[0041] In the mixture of the sulfonate containing the component (A) obtained by the sulfonation reaction, inorganic metal compounds such as unreacted component (C) and the hydrolyzate of component (C) are included. When removing the insoluble components in the mixture, the precipitate precipitated from the mixture to which the insoluble components are to be removed can be separated and removed. Alternatively, the insoluble components can be precipitated from the mixture to which the insoluble components are to be removed, and the precipitated precipitate can be separated and removed. The precipitate contains inorganic metal compounds (D) such as unreacted component (C) and the hydrolyzate of component (C).

[0042] The insoluble components to be removed can be inorganic metal compounds (D).

[0043] The inorganic metal compound as component (D) [hereinafter referred to as component (D)] may include salts, hydroxides, oxides, etc. Component (D) may be an inorganic metal compound not containing halogen.

[0044] As component (D), there may be mentioned the above-mentioned inorganic sulfates, hydrolyzates of the above-mentioned inorganic sulfates, neutralized products of the above-mentioned inorganic sulfates, neutralized products of the hydrolyzates of the above-mentioned inorganic sulfates, oxides of the above-mentioned inorganic sulfates, oxides of the hydrolyzates of the above-mentioned inorganic sulfates, and oxides of the neutralized products of the above-mentioned inorganic sulfates, etc.

[0045] Specifically, as component (D), one or more selected from the following (D1) to (D4) may be mentioned.

[0046] (D1) At least one compound selected from MHSO3, M2SO3 and M2S2O5 (wherein M represents a metal cation)

[0047] (D2) Hydrolyzate of the compound of (D1)

[0048] (D3) At least one neutralized product selected from the neutralized product of the compound of (D1) and the neutralized product of the hydrolyzate of (D2)

[0049] (D4) At least one oxide selected from the oxide of the compound of (D1), the oxide of the hydrolyzate of (D2), and the oxide of the neutralized product of (D3)

[0050] In (D1), M in the formula may include alkali metal ions, alkaline earth metal ions, etc.

[0051] Among (D1), as MHSO3, potassium bisulfite, sodium bisulfite, etc. may be mentioned.

[0052] Among (D1), as M2SO3, potassium sulfite, sodium sulfite, etc. may be mentioned.

[0053] Among (D1), as M2S2O5, potassium metabisulfite, sodium metabisulfite, etc. may be mentioned.

[0054] As the above-mentioned hydrolyzate of (D2), when the sulfonating agent of component (D) is M2S2O5, potassium bisulfite, sodium bisulfite, etc. may be mentioned.

[0055] As the above-mentioned neutralized product of (D3), there may be mentioned a compound obtained by neutralizing a compound selected from the compounds of (D1) and its hydrolyzates with a neutralizing agent.

[0056] As the above-mentioned oxide of (D4), a compound obtained by oxidizing a compound selected from the compounds of the above-mentioned (D1), the hydrolyzate of the above-mentioned (D2), and the neutralized product of the above-mentioned (D3) with an oxidizing agent can be cited.

[0057] Next, a method for producing the sulfonate composition of the present invention will be described. In the method for producing the sulfonate composition of the present invention, the following operations are carried out, that is, an operation of reacting the component (C) with the component (A) under specified conditions in the presence of the component (B) to obtain a mixture containing sulfonate; an operation of removing insoluble components from the mixture.

[0058] In the sulfonation reaction in which the component (C) reacts with the component (A), the component (C) is reacted with the component (A) to obtain a sulfonate represented by the following general formula (2) [hereinafter referred to as the component (S)].

[0059] ROOC-(CH2) p -CH(SO3M)-CH2-(CH2) q -COOR’(2)

[0060] (In the formula, M is a cation, and R and R’ are independently groups selected from an alkyl group having 10 carbon atoms and an alkenyl group having 10 carbon atoms. p and q are each a number of 0 or more and 18 or less, and the sum of p and q is 0 or more and 18 or less.)

[0061] In the general formula (2), M is a cation. Specifically, alkali metal ions such as sodium ions and potassium ions, and ammonium ions can be cited.

[0062] In the general formula (2), R and R’ are the same as the manner and preferred manner of R and R’ in the general formula (1) of the above-mentioned component (A).

[0063] p and q are each 0 or more, and can be 18 or less, 16 or less, 12 or less, 8 or less, 4 or less, 2 or less, 1 or less, 0.

[0064] The sum of p and q is 0 or more, and can be 18 or less, 16 or less, 12 or less, 8 or less, 4 or less, 2 or less, 1 or less, 0.

[0065] Regarding the usage amount of the component (C), from the viewpoints of obtaining a high-quality component (S) and obtaining the component (S) with a high conversion rate, the usage amount of the component (C) relative to 1 mole of the component (A) is preferably 1.00 mole or more and 1.20 moles or less. The usage amount of the component (C) relative to 1 mole of the component (A) can be selected from more preferably greater than 1.00 mole, more preferably 1.05 moles or more, more preferably 1.10 moles or more, more preferably 1.13 moles or more, and more preferably 1.17 moles or less.

[0066] In the sulfonation reaction, a separately prepared (S) component can be used as a solubilizer (or reaction accelerator) or the like. As the separately prepared (S) component, the (S) component obtained after removing the insoluble component, which will be described in detail later, or the (S) component obtained by adjusting the amount of the solvent after removing the insoluble component can be used. Regarding the amount of the (S) component added as a solubilizer, from the viewpoint of dissolving the poorly soluble (A) component in the solvent, it is preferably 1% by mass or more relative to the amount of the (A) component used, and from the viewpoint of productivity, it is preferably 10% by mass or less.

[0067] Unless otherwise specified, the modes and preferred modes described in this specification are common whether or not a separately prepared (S) component is used.

[0068] Regarding the amount of the (B1) component used in the sulfonation reaction, from the viewpoint of reducing the content of the (D) inorganic metal compound in the obtained sulfonate composition and obtaining a high-purity sulfonate composition, relative to 100 parts by mass of the (A) component, it is preferably 7 parts by mass or more, more preferably 7.5 parts by mass or more, further preferably 20 parts by mass or more, and preferably 380 parts by mass or less, more preferably 300 parts by mass or less, further preferably 216 parts by mass or less, still more preferably 199 parts by mass or less, still more preferably 100 parts by mass or less, still more preferably 85 parts by mass or less, still more preferably 75 parts by mass or less, still more preferably 60 parts by mass or less, still more preferably 55 parts by mass or less, still more preferably 51 parts by mass or less. In either case, whether or not a separately prepared (S) component is used in the sulfonation reaction, the amount of the (B1) component used in the sulfonation reaction is preferably within this range.

[0069] Regarding the amount of the (B2) component used in the sulfonation reaction, from the viewpoint of reducing the content of the (D) inorganic metal compound in the obtained sulfonate composition and obtaining a high-purity sulfonate composition, relative to 100 parts by mass of the (A) component, it is preferably 2.0 parts by mass or more, more preferably 2.5 parts by mass or more, further preferably 3.0 parts by mass or more, and preferably 180 parts by mass or less, more preferably 120 parts by mass or less, further preferably 50 parts by mass or less, still more preferably 41 parts by mass or less, still more preferably 39 parts by mass or less, still more preferably 25 parts by mass or less, still more preferably 18 parts by mass or less, still more preferably 15 parts by mass or less. In either case, whether or not a separately prepared (S) component is used in the sulfonation reaction, the amount of the (B2) component used in the sulfonation reaction is preferably within this range.

[0070] Regarding the mass ratio (B1) / (B2) of the usage amount of the (B1) component to the usage amount of the (B2) component in the (B) component during the sulfonation reaction, from the viewpoint of reducing the content of the (D) inorganic metal compound in the obtained sulfonate composition and obtaining a high-purity sulfonate composition, it is preferably 0.3 or more, more preferably 0.4 or more, further preferably 0.7 or more, still further preferably 0.9 or more, still further preferably 1.0 or more, still further preferably 2.0 or more, still further preferably 5.0 or more, and for example, it can be 1000 or less, 100 or less, 50 or less, 30 or less, 20 or less, 10 or less. This mass ratio (B1) / (B2) is preferably within this range regardless of whether the separately prepared (S) component is used or not used during the sulfonation reaction.

[0071] Regarding the reaction time of the sulfonation reaction, from the viewpoints of obtaining a high-quality (S) component and obtaining a high conversion rate (e.g., 90% or more), it is preferably 10 hours or less.

[0072] Regarding the reaction temperature of the sulfonation reaction, from the viewpoint of suppressing the hydrolysis of the (S) component, it is preferably below 125 °C, more preferably 120 °C or less, and from the viewpoint of accelerating the reaction rate and shortening the reaction time, it is preferably 100 °C or more, more preferably 105 °C or more, further preferably 110 °C or more.

[0073] During the sulfonation reaction, depending on the boiling point of the (B) solvent, it can be carried out at normal pressure (atmospheric pressure) or under pressure. For example, when the (B) component is propylene glycol, its boiling point is 188.2 °C, so the reaction can also be carried out at normal pressure.

[0074] In addition, the sulfonation reaction can be carried out in an air atmosphere or in an inert gas atmosphere such as nitrogen.

[0075] After the sulfonation reaction, it is preferable to adjust the concentration of the mixture obtained in the sulfonation reaction using the (B1) component and / or the (B2) component. For example, it is preferable to add one or more solvents selected from the (B1) component and the (B2) component to the mixture obtained in the sulfonation reaction and then remove the insoluble components in the mixture.

[0076] From the viewpoint of a low content of the (D) inorganic metal compound in the obtained sulfonate composition and obtaining a high-purity sulfonate composition, it is preferable to adjust the mass ratio (B1) / (B2) of the content of the component (B1) to the content of the component (B2) in the mixture after adjusting the concentration to 0.3 or more, more preferably to 0.4 or more, further preferably to 0.7 or more, still more preferably to 0.9 or more, still more preferably to 1.0 or more, and for example, it can be adjusted to 1000 or less, 100 or less, 50 or less, 30 or less, 20 or less, 10 or less. This mass ratio (B1) / (B2) is preferably within this range in either case where the component (S) prepared separately is used or not used in the sulfonation reaction.

[0077] When the component (B1) is mixed into the mixture obtained in the sulfonation reaction, regarding the content of the component (B1) in the composition after mixing the component (B1) into the mixture obtained in the sulfonation reaction, from the viewpoints of handleability based on physical properties and operability in subsequent processes, the component (B1) can be mixed as follows: based on 100 parts by mass of the component (A) before the sulfonation reaction, the component (B1) is preferably 5 parts by mass or more, more preferably 10 parts by mass or more, further preferably 15 parts by mass or more, and preferably 380 parts by mass or less, more preferably 300 parts by mass or less, further preferably 200 parts by mass or less, still more preferably 60 parts by mass or less. If the content of the component (B1) in the mixture obtained in the sulfonation reaction is within the above range, the subsequent processes can be carried out without mixing the component (B1).

[0078] When the component (B2) is mixed into the mixture obtained in the sulfonation reaction, regarding the content of the component (B2) in the composition after mixing the component (B2) into the mixture obtained in the sulfonation reaction, from the viewpoints of handleability based on physical properties and operability in subsequent processes, the component (B2) can be mixed as follows: based on 100 parts by mass of the component (A) before the sulfonation reaction, the component (B2) is preferably 5 parts by mass or more, more preferably 15 parts by mass or more, further preferably 25 parts by mass or more, and preferably 180 parts by mass or less, more preferably 120 parts by mass or less, further preferably 80 parts by mass or less, still more preferably 50 parts by mass or less. If the content of the component (B2) in the mixture obtained in the sulfonation reaction is within the above range, the subsequent processes can be carried out without mixing the component (B2).

[0079] When mixing the component (B1) into the mixture obtained from the sulfonation reaction, from the viewpoints of ease of handling based on physical properties and operability in subsequent processes, in the mixture obtained from the sulfonation reaction, based on 100 parts by mass of the component (A) before the sulfonation reaction, for example, 1 part by mass or more, 1.5 parts by mass or more, 10 parts by mass or more, 20 parts by mass or more, and 350 parts by mass or less, 320 parts by mass or less, 300 parts by mass or less, 250 parts by mass or less, 200 parts by mass or less, 150 parts by mass or less, 100 parts by mass or less, 75 parts by mass or more, 50 parts by mass or less of the component (B1) can be mixed.

[0080] When mixing the component (B2) into the mixture obtained from the sulfonation reaction, from the viewpoints of ease of handling based on physical properties and operability in subsequent processes, in the mixture obtained from the sulfonation reaction, based on 100 parts by mass of the component (A) before the sulfonation reaction, for example, 1 part by mass or more, 5 parts by mass or more, 15 parts by mass or more, 20 parts by mass or more, and 150 parts by mass or less, 100 parts by mass or less, 50 parts by mass or less, 40 parts by mass or less, 35 parts by mass or less, 30 parts by mass or less of the component (B2) can be mixed.

[0081] Regarding the removal of insoluble components in the mixture obtained from the sulfonation reaction, insoluble components such as the component (D) in the mixture are removed. When removing the insoluble components, for example, the insoluble components precipitated from the mixture are separated and removed by filtration, centrifugation, etc. Before removing the insoluble components, the unreacted component (C) and / or its hydrolyzate in the mixture to be subjected to the removal of insoluble components can be neutralized and / or oxidized. When performing the neutralization reaction and the oxidation reaction, the oxidation reaction can be carried out after the neutralization reaction, or the neutralization reaction can be carried out after the oxidation reaction.

[0082] Regarding the reaction temperatures of the neutralization reaction and the oxidation reaction, from the viewpoint of suppressing the hydrolysis of the component (S), it is preferably 60 °C or lower, more preferably 55 °C or lower, and from the viewpoint of operability, it is preferably 20 °C or higher.

[0083] It should be noted that the reaction temperatures of the neutralization reaction and the oxidation reaction refer to the temperature of the mixture obtained from the sulfonation reaction during the neutralization reaction and the oxidation reaction. Since the neutralization reaction and the oxidation reaction are accompanied by heat release, cooling is carried out as needed. By operating within the above temperature range, the hydrolysis of the component (S) can be suppressed.

[0084] The neutralizing agent used in the neutralization reaction is not particularly limited, and alkali metal carbonates such as sodium carbonate and potassium carbonate, alkali metal bicarbonates such as sodium bicarbonate and potassium bicarbonate, hydroxides of alkali metals such as sodium hydroxide and potassium hydroxide can be used. The neutralizing agent can be used in the form of powder or aqueous solution. From the viewpoints of ease of operation and obtaining high-quality sulfonates, an aqueous solution of sodium carbonate, sodium bicarbonate, or an aqueous solution of sodium hydroxide is preferred. The concentration of the aqueous solution of the neutralizing agent is preferably 1% by mass or more and 48% by mass or less. When the neutralizing agent is an aqueous solution of sodium carbonate or an aqueous solution of sodium bicarbonate, an aqueous solution with a concentration of sodium carbonate or sodium bicarbonate of 2% by mass or more and 22% by mass or less is more preferred. In addition, when the neutralizing agent is an aqueous solution of sodium hydroxide, an aqueous solution with a concentration of sodium hydroxide of 2% by mass or more and 35% by mass or less is more preferred.

[0085] The oxidizing agent used in the oxidation reaction is not particularly limited. From the viewpoints of ease of operation, efficiency of oxidation treatment, and obtaining high-quality sulfonates, peroxides of alkali metals or alkaline earth metals, hypochlorites of alkali metals or alkaline earth metals, potassium permanganate, hydrogen peroxide, etc. are preferred, and hydrogen peroxide is more preferred. An aqueous hydrogen peroxide solution obtained by dissolving hydrogen peroxide in water can be used as the oxidizing agent.

[0086] Regarding the content of the (B1) component in the mixture for removing insoluble components, from the viewpoints of a small content of inorganic metal compounds in the sulfonate composition and obtaining a high-purity sulfonate composition, based on 100 parts by mass of the (A) component before the sulfonation reaction, it is preferably 5 parts by mass or more, more preferably 7 parts by mass or more, further preferably 7.5 parts by mass or more, still further preferably 8 parts by mass or more, still further preferably 10 parts by mass or more, still further preferably 15 parts by mass or more, and preferably 380 parts by mass or less, more preferably 300 parts by mass or less, further preferably 216 parts by mass or less, still further preferably 200 parts by mass or less, still further preferably 199 parts by mass or less, still further preferably 100 parts by mass or less, still further preferably 85 parts by mass or less, still further preferably 75 parts by mass or less, still further preferably 65 parts by mass or less, still further preferably 60 parts by mass or less, still further preferably 55 parts by mass or less.

[0087] In the mixture for removing insoluble components, from the same viewpoints, the content of the (B1) component is preferably 5% by mass or more, more preferably 7% by mass or more, and preferably 65% by mass or less, more preferably 60% by mass or less, further preferably 40% by mass or less, still further preferably 30% by mass or less, still further preferably 20% by mass or less.

[0088] Regarding the content of component (B1) in the mixture for removing insoluble components, in any case, whether or not component (S) prepared separately is used in the sulfonation reaction, this range is preferred.

[0089] It should be noted that the contents of component (B1) and component (B2) in the mixture for removing insoluble components can be calculated values (the same applies hereinafter) calculated based on the measured values in the mixture, the charged amount of component (A) in the sulfonation reaction, and the measured values of the contents of each component in the mixture after removing insoluble components.

[0090] Regarding the content of component (B2) in the mixture for removing insoluble components, from the viewpoint of reducing the content of inorganic metal compounds in the sulfonate composition and obtaining a high-purity sulfonate composition, based on 100 parts by mass of component (A) before the sulfonation reaction, it is preferably 5 parts by mass or more, more preferably 7 parts by mass or more, further preferably 15 parts by mass or more, still further preferably 25 parts by mass or more, and preferably 180 parts by mass or less, more preferably 120 parts by mass or less, further preferably 80 parts by mass or less, still further preferably 45 parts by mass or less, still further preferably 40 parts by mass or less, still further preferably 37 parts by mass or less, still further preferably 35 parts by mass or less, still further preferably 30 parts by mass or less.

[0091] In the mixture for removing insoluble components, from the same viewpoint, the content of component (B2) is preferably 3% by mass or more, more preferably 5% by mass or more, and preferably 40% by mass or less, more preferably 35% by mass or less, further preferably 30% by mass or less, still further preferably 26% by mass or less, still further preferably 25% by mass or less, still further preferably 22% by mass or less, still further preferably 20% by mass or less.

[0092] Regarding the content of component (B2) in the mixture for removing insoluble components, in any case, whether or not component (S) prepared separately is used in the sulfonation reaction, this range is preferred.

[0093] In the mixture for removing insoluble components, regarding the mass ratio (B1) / (S + B1 + B2) of the content of component (B1) to the total content of component (S), component (B1) and component (B2), from the viewpoint of removing inorganic metal compounds, it is 0.05 or more, preferably 0.09 or more, more preferably 0.10 or more, and from the viewpoint of obtaining a sulfonate composition with high purity and / or higher concentration, it is 0.65 or less, preferably 0.59 or less, more preferably 0.55 or less, further preferably 0.50 or less, still further preferably 0.40 or less, and even more preferably 0.35 or less.

[0094] In the mixture for removing insoluble components, regarding the mass ratio (B2) / (S + B1 + B2) of the content of component (B2) to the total content of component (S), component (B1) and component (B2), from the viewpoint of removing inorganic metal compounds, it is 0.03 or more, preferably 0.10 or more, and from the viewpoint of obtaining a sulfonate composition with high purity and / or higher concentration, it is 0.26 or less, preferably 0.25 or less, more preferably 0.23 or less, further preferably 0.20 or less, still further preferably 0.18 or less.

[0095] Regarding the mass ratio (B1) / (B2) of the content of component (B1) to the content of component (B2) in the mixture for removing insoluble components, from the viewpoint of a low content of inorganic metal compounds in the sulfonate composition and obtaining a sulfonate composition with high purity, it is preferably 0.3 or more, and can be selected from, for example, 0.6 or more, 0.80 or more, 0.82 or more, 0.85 or more, 0.9 or more, and can also be selected from 1000 or less, 100 or less, 50 or less, 30 or less, 20 or less, 10 or less, 5 or less, 2.5 or less, 2 or less. From the viewpoint of precipitating a large amount of inorganic metal compounds such as inorganic salts in the mixture, the amount of component (B2) can be small, and thus the upper limit value of this mass ratio (B1) / (B2) can be arbitrarily selected according to the amount of component (S) in the mixture and the solubility of component (S) relative to component (B1).

[0096] If the contents of component (B1) and component (B2) in the mixture for removing insoluble components are as described above, the amount of inorganic metal compounds dissolved in the mixture can be reduced in a state where component (S) is dissolved in the mixture. By subjecting this mixture to the removal of insoluble components, a mixture with a high concentration of component (S) and a low content of inorganic metal compounds can be obtained.

[0097] Whether or not the (S) component prepared separately is used in the sulfonation reaction, the preferred contents of (B1) and (B2) in the mixture for removing the insoluble components and the mass ratio (B1) / (B2) of the content of the (B1) component to the content of the (B2) component are as described above.

[0098] The amounts of the (B1) component and the (B2) component used in the sulfonation reaction can be determined such that the contents of the (B1) component and the (B2) component are the above-mentioned parts by mass (or contents). Alternatively, one or more solvents selected from the (B1) component and the (B2) component can be added to the mixture before removing the insoluble components, and the mixture with adjusted contents of the (B1) component and the (B2) component can be subjected to the removal of the insoluble components. The adjustment of the contents of the (B1) component and the (B2) component in the mixture for removing the insoluble components can be carried out during or after the sulfonation reaction and before removing the insoluble components.

[0099] Regarding the viscosity of the mixture for removing the insoluble components at 20 °C, from the viewpoints of easy handling based on physical properties and operability in subsequent processes, it is preferably 600 mPa·s or less, more preferably 500 mPa·s or less, further preferably 470 mPa·s or less, still more preferably 450 mPa·s or less, and can be, for example, 0.1 mPa·s or more, 1 mPa·s or more, 10 mPa·s or more. The viscosity of this mixture can be measured using a B-type rotational viscometer at 20 °C.

[0100] When removing the insoluble components, for example, the mixture for removing the insoluble components can be maintained at 50 °C or lower, and the precipitated (D) component can be separated and removed by a known separation method. Alternatively, the insoluble components can be precipitated from the mixture for removing the insoluble components, and the precipitated (D) component and the like can be separated and removed by a known separation method.

[0101] It should be noted that from the viewpoint of obtaining a sulfonate with high purity, azeotropic distillation is preferably not carried out when removing the insoluble components.

[0102] Examples of the above-mentioned separation methods include treatment with an adsorption membrane or adsorbent, addition of a flocculant, centrifugation, standing, decantation, filtration, etc. Filtration can be gravity filtration, pressure filtration, vacuum filtration, etc. Additionally, when removing the insoluble components, a filter aid and a flocculant can be used in combination as needed. There is no particular limitation on the filter aid, and diatomaceous earth, silica, glass fiber, activated carbon, etc. that are industrially used can be used.

[0103] In the case of using a filter aid, from the viewpoints of removing inorganic metal compounds and the amount of liquid contained in the filter aid, the addition amount of the filter aid is preferably 0.01 part by mass or more, more preferably 1 part by mass or more, and preferably 20 parts by mass or less, more preferably 10 parts by mass or less, relative to every 100 parts by mass of the mixture for removing insoluble components.

[0104] In addition, regarding the particle diameter of the component (D) captured during the insoluble component removal operation, from the viewpoints of the removal rate of insoluble components and the operability in subsequent processes, it can be, for example, 10 μm or less, 5 μm or less, and can be 0.1 μm or more, 1 μm or more. This particle diameter is a value guaranteed as the capture particle diameter of the filter aid and filter medium used. That is, this particle diameter is the particle diameter of the particles captured by the mesh of the filtration mechanism.

[0105] From the viewpoints of the appearance stability of the sulfonate composition and suppressing the generation of turbidity, precipitates, and stability at low temperatures when the sulfonate composition is combined with other components, it is preferable to remove insoluble components as follows, that is, in the mixture after removing insoluble components, the content of sodium sulfate is preferably 1.2% by mass or less, more preferably 0.8% by mass or less, further preferably 0.7% by mass or less, and even more preferably 0.5% by mass or less.

[0106] The method for producing a sulfonate composition of the present invention can obtain a sulfonate composition that can be directly used as a product. The sulfonate composition can be used for secondary products. The method for producing a sulfonate composition of the present invention can not add component (B1) during the period after the production of the sulfonate, that is, after the removal of insoluble components and before being used for secondary products.

[0107] It should be noted that the method for producing a sulfonate composition of the present invention can adjust the amount of solvent in the sulfonate composition by adding a solvent containing one or more selected from component (B1) and component (B2) in such a manner that the component (S) etc. in the sulfonate composition becomes a desired concentration after removing insoluble components.

[0108] By using the method for producing a sulfonate composition of the present invention, a sulfonate composition containing component (S) can be obtained.

[0109] In the sulfonate composition of the present invention, regarding the content of component (B1), from the viewpoints of obtaining a sulfonate composition with a low content of inorganic metal compounds and suppressing turbidity and precipitation caused by the precipitation of inorganic metal compounds, it is preferably 5% by mass or more, more preferably 10% by mass or more, further preferably 12% by mass or more, and preferably 65% by mass or less, more preferably 58% by mass or less, further preferably 35% by mass or less, and even more preferably 30% by mass or less. It is preferred that the content of (B1) is within this range and the content of (B2) is within the following range.

[0110] In the sulfonate composition of the present invention, regarding the content of component (B2), from the viewpoints of obtaining a sulfonate composition with a low content of inorganic metal compounds and suppressing turbidity and precipitation caused by the precipitation of inorganic metal compounds, it is preferably 2% by mass or more, more preferably 3% by mass or more, further preferably 4% by mass or more, even more preferably 5% by mass or more, and preferably 30% by mass or less, more preferably 25% by mass or less, further preferably 20% by mass or less.

[0111] The content of component (B1) and component (B2) in the sulfonate composition of the present invention may be the content after removing insoluble components, or may be the content after adjusting the amount of solvent after removing insoluble components.

[0112] From the viewpoints of appearance uniformity and production efficiency, the sulfonate composition of the present invention may contain component (S) preferably at 50% by mass or more, more preferably at 55% by mass or more, and preferably at 70% by mass or less, more preferably at 68% by mass or less.

[0113] In addition, from the viewpoints of appearance uniformity and operability, the sulfonate composition of the present invention may contain component (S) preferably at 19% by mass or more, and preferably at 80% by mass or less, more preferably at 70% by mass or less, further preferably at 68% by mass or less.

[0114] From the viewpoints of production efficiency, appearance uniformity and operability, the sulfonate composition of the present invention may contain component (B) preferably at 20% by mass or more, more preferably at 25% by mass or more, and preferably at 45% by mass or less.

[0115] In addition, from the viewpoints of appearance uniformity and operability, the sulfonate composition of the present invention may contain component (B) preferably at 45% by mass or more, and preferably at 80% by mass or less.

[0116] From the viewpoint of the purity of the (S) component, the content of the (D) component in the sulfonate composition of the present invention is preferably less than 1.6 parts by mass, more preferably 1.5 parts by mass or less, still more preferably 1.0 part by mass or less, relative to 100 parts by mass of the content of the (S) component. Further, from the viewpoint of productivity, it can be, for example, 0.10 part by mass or more, and further can be 0.15 part by mass or more.

[0117] The sulfonate composition of the present invention may contain components other than the (S) component and the (B) component. For example, it may contain diesters or monoesters of maleic acid or fumaric acid, 2-propylheptanol, 4-methyl-2-propylhexanol, 5-methyl-2-propylhexanol, sulfosuccinic acid monoesters salts, salts of maleic acid or fumaric acid, etc. In addition, it may also contain additives and regulators such as pH buffers, preservatives, etc.

[0118] The sulfonate composition of the present invention can be used, for example, as a raw material for products such as detergents, solubilizers, treatment agents, modifiers, wetting agents, penetrants, pesticides, paints, cosmetics, and emulsifiers.

[0119] As one mode of the method for producing the sulfonate composition of the present invention, there can be cited the following method for producing a sulfonate composition, which performs the following operations: reacting a (C) sulfonating agent with a compound represented by the general formula (1) of (A) in the presence of one or more solvents selected from (B1) organic solvents and (B2) water to obtain a mixture containing a sulfonate represented by the following general formula (2) of (S); and an operation of removing insoluble components from the above mixture.

[0120] The mixture to be subjected to the removal of the insoluble components contains the (S) component, the (B1) component, and the (B2) component. The mass ratio (B1) / (S + B1 + B2) of the content of the (B1) component to the total content of the (S) component, the (B1) component, and the (B2) component is 0.05 or more and 0.65 or less, preferably 0.59 or less.

[0121] (B2) component, the mass ratio (B2) / (S + B1 + B2) of the content of the (B2) component to the total content of the (S) component, the (B1) component, and the (B2) component is 0.03 or more and 0.26 or less, preferably 0.20 or less, and preferably the mass ratio (B1) / (B2) of the content of the (B1) component to the content of the (B2) component is 0.80 or more. In this method for producing the sulfonate composition, an operation of precipitating insoluble components from the mixture containing a sulfonate represented by the following general formula (2) of (S), and an operation of removing the components precipitated from the mixture can be performed.

[0122] ROOC-(CH2) n -CH=CH-(CH2) m-COOR’ (1)

[0123] (In the formula, R and R’ are independently groups selected from an alkyl group having 10 carbon atoms and an alkenyl group having 10 carbon atoms. n and m are each a number of 0 or more and 18 or less, and the sum of n and m is 0 or more and 18 or less.)

[0124] ROOC-(CH2) p -CH(SO3M)-CH2-(CH2) q -COOR’(2)

[0125] (In the formula, M is a cation, R and R’ are independently groups selected from an alkyl group having 10 carbon atoms and an alkenyl group having 10 carbon atoms. p and q are each a number of 0 or more and 18 or less, and the sum of p and q is 0 or more and 18 or less.)

[0126] When insolubles are precipitated from the mixture, a method of performing one or a combination of two or more of an oxidation reaction of a component selected from the mixture, a neutralization reaction of a component in the mixture, and cooling of the mixture can be carried out.

[0127] In addition, in the method for producing the sulfonate composition of the present invention, from the viewpoint of obtaining a high-quality (S) component, after reacting the (C) component with the (A) component to obtain a mixture containing the (S) component, the insoluble components can be removed without heating the mixture (for example, raising the temperature to 80°C or higher). Further, from the viewpoint of obtaining a highly pure sulfonate, it is preferable to remove the insoluble components without performing azeotropic distillation after reacting the (C) component with the (A) component to obtain a mixture containing the (S) component.

[0128] <Mode of the present invention>

[0129] Hereinafter, modes of the present invention are exemplified. Also in the following modes: the compound represented by the general formula (1) is the (A) component, the organic solvent is the (B1) component, water is the (B2) component, one or more solvents selected from the (B1) component and the (B2) component are the (B) component, the sulfonating agent is the (C) component, and the sulfonate represented by the general formula (2) is the (S) component.

[0130] <1> A method for producing a sulfonate composition, which performs the following operations: an operation of reacting a (C) sulfonating agent with an (A) compound represented by the following general formula (1) in the presence of one or more solvents selected from the group consisting of (B) (B1) an organic solvent and (B2) water to obtain a mixture containing a (S) sulfonate represented by the following general formula (2); and an operation of removing insoluble components from the above mixture,

[0131] The mixture for removing the above-mentioned insoluble components contains component (S), component (B1), and component (B2). The mass ratio (B1) / (S + B1 + B2) of the content of component (B1) to the total content of component (S), component (B1), and component (B2) is 0.05 or more and 0.65 or less.

[0132] The mass ratio (B2) / (S + B1 + B2) of the content of component (B2) to the total content of component (S), component (B1), and component (B2) is 0.03 or more and 0.26 or less.

[0133] ROOC-(CH2) n -CH=CH-(CH2) m -COOR’ (1)

[0134] (In the formula, R and R’ are independently groups selected from an alkyl group having 10 carbon atoms and an alkenyl group having 10 carbon atoms. n and m are each a number of 0 or more and 18 or less, and the sum of n and m is 0 or more and 18 or less.)

[0135] ROOC-(CH2) p -CH(SO3M)-CH2-(CH2) q -COOR’(2)

[0136] (In the formula, M is a cation, and R and R’ are independently groups selected from an alkyl group having 10 carbon atoms and an alkenyl group having 10 carbon atoms. p and q are each a number of 0 or more and 18 or less, and the sum of p and q is 0 or more and 18 or less.)

[0137] <2> According to the method for producing the sulfonate composition described in <1> above, wherein component (A) is a compound in which R and R’ in the above general formula (1) are independently groups selected from 2-propylheptyl, 4-methyl-2-propylhexyl, and 5-methyl-2-propylhexyl.

[0138] <3> According to the method for producing the sulfonate composition described in <1> or <2> above, wherein after adding one or more solvents selected from component (B1) and component (B2) to the above mixture, the insoluble components in the mixture are removed.

[0139] <4> According to the method for producing the sulfonate composition described in any one of <1> to <3> above, wherein in the above sulfonate composition, the content of component (B1) is 5% by mass or more and 65% by mass or less, and the content of component (B2) is 3% by mass or more and 25% by mass or less.

[0140] <5> According to the method for producing the sulfonate composition described in any one of <1> to <4> above, wherein component (B1) is at least one selected from a monohydric alcohol and a polyhydric alcohol.

[0141] <6> The method for producing a sulfonate composition according to any one of <1> to <5> above, wherein the component (C) is at least one compound selected from MHSO3, M2SO3 and M2S2O5 (wherein M represents a cation).

[0142] <7> The method for producing a sulfonate composition according to any one of <1> to <6> above, wherein the component (C) is used in a proportion of 1.00 mole or more and 1.20 moles or less relative to 1 mole of the component (A).

[0143] <8> The method for producing a sulfonate composition according to any one of <1> to <7> above, wherein the component (C) is reacted with the component (A) at a reaction temperature of 100 °C or higher and lower than 125 °C, under normal pressure or pressure.

[0144] <9> The method for producing a sulfonate composition according to any one of <1> to <8> above, wherein, before removing the insoluble components, the unreacted component (C) in the above mixture is neutralized and / or oxidized.

[0145] <10> The method for producing a sulfonate composition according to any one of <1> to <9> above, wherein a sulfonate obtained by reacting the component (A) with the component (C) (hereinafter referred to as the separately prepared component (S)) is separately prepared, and the component (C) is reacted with the component (A) in the coexistence of this sulfonate.

[0146] <11> The method for producing a sulfonate composition according to any one of <1> to <10> above, wherein R and R' in the general formula (1) are independently groups selected from branched-chain alkyl groups having 10 carbon atoms and branched-chain alkenyl groups having 10 carbon atoms, and further are branched-chain alkyl groups having 10 carbon atoms.

[0147] <12> The method for producing a sulfonate composition according to any one of <1> to <10> above, wherein R and R' in the general formula (1) are independently groups selected from n-decyl, isodecyl, 2-propylheptyl, 4-methyl-2-propylhexyl and 5-methyl-2-propylhexyl.

[0148] <13> The method for producing a sulfonate composition according to any one of <1> to <10> above, wherein R and R' in the general formula (1) are independently groups selected from n-decenyl and isodecenyl.

[0149] <14> The method for producing a sulfonate composition according to any one of <1> to <13> above, wherein one kind or two or more kinds of the component (A) are used.

[0150] <15> The method for producing a sulfonate composition according to any one of <1> to <14> above, wherein one or both of the components (A) are compounds in which R and R' are 2-propylheptyl.

[0151] <16> The method for producing a sulfonate composition according to any one of <1> to <15> above, wherein n and m in the general formula (1) are each 0 or more, and 18 or less, 16 or less, 12 or less, 8 or less, 4 or less, 2 or less, 1 or less, or 0.

[0152] <17> The method for producing a sulfonate composition according to any one of <1> to <16> above, wherein the sum of n and m in the general formula (1) is 0 or more, and 18 or less, 16 or less, 12 or less, 8 or less, 4 or less, 2 or less, 1 or less, or 0.

[0153] <18> The method for producing a sulfonate composition according to any one of <5> to <17> above, wherein the monohydric alcohol has 1 to 12 carbon atoms, and further is one or more compounds selected from methanol, ethanol, 1-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-octanol, 1-nonanol, 2-nonanol, 5-nonanol, 1-decanol, 1-dodecanol, 3,5,5-trimethylhexan-1-ol, 2,6-dimethyl-4-heptanol, 2-propylheptanol, 4-methyl-2-propylhexanol, 5-methyl-2-propylhexanol; still further is one or more compounds selected from ethanol, 1-butanol, and 1-propanol; still further is ethanol.

[0154] <19> The method for producing a sulfonate composition according to any one of <5> to <17> above, wherein the polyhydric alcohol has 2 to 12 carbon atoms and is divalent or more and hexavalent or less.

[0155] <20> The method for producing a sulfonate composition according to any one of <5> to <17> and <19> above, wherein the polyhydric alcohol is one or more compounds selected from ethylene glycol, propylene glycol, 1,3-butanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,10-decanediol, diethylene glycol, triethylene glycol, tetraethylene glycol, dipropylene glycol, tripropylene glycol, glycerol, xylitol, sorbitol; further is one or more compounds selected from propylene glycol and glycerol; still further is propylene glycol.

[0156] <21> The method for producing a sulfonate composition according to any one of <1> to <20> above, wherein the component (B1) is one or more compounds selected from ethanol, 1-butanol, 1-propanol, glycerol, and propylene glycol; further is one or more compounds selected from ethanol and propylene glycol.

[0157] <22> The method for producing the sulfonate composition according to any one of <1> to <21> above, wherein the component (B2) is any one of tap water, purified water, and ion-exchanged water.

[0158] <23> The method for producing the sulfonate composition according to any one of <1> to <22> above, wherein the component (C) is one or more compounds selected from sulfites, bisulfites, and metabisulfites. Further, the sulfite is one or more sulfites selected from ammonium sulfite, potassium sulfite, and sodium sulfite, the bisulfite is one or more bisulfites selected from ammonium bisulfite, potassium bisulfite, and sodium bisulfite, and the metabisulfite is one or more metabisulfites selected from potassium metabisulfite and sodium metabisulfite.

[0159] <24> The method for producing the sulfonate composition according to any one of <1> to <23> above, wherein the component (C) is sodium metabisulfite or potassium metabisulfite, and further is sodium metabisulfite.

[0160] <25> The method for producing the sulfonate composition according to any one of <1> to <24> above, wherein R and R' in the general formula (2) are independently groups selected from branched-chain alkyl groups having 10 carbon atoms and branched-chain alkenyl groups having 10 carbon atoms, and further are branched-chain alkyl groups having 10 carbon atoms.

[0161] <26> The method for producing the sulfonate composition according to any one of <1> to <24> above, wherein R and R' in the general formula (2) are independently groups selected from n-decyl, isodecyl, 2-propylheptyl, 4-methyl-2-propylhexyl, and 5-methyl-2-propylhexyl.

[0162] <27> The method for producing the sulfonate composition according to any one of <1> to <24> above, wherein R and R' in the general formula (2) are independently groups selected from n-decenyl and isodecenyl.

[0163] <28> The method for producing the sulfonate composition according to any one of <1> to <24> above, wherein R and R' in the general formula (2) are independently groups selected from 2-propylheptyl, 4-methyl-2-propylhexyl, and 5-methyl-2-propylhexyl.

[0164] <29> The method for producing the sulfonate composition according to any one of <1> to <28> above, wherein p and q in the general formula (2) are each 0 or more and 18 or less, 16 or less, 12 or less, 8 or less, 4 or less, 2 or less, 1 or less, or 0.

[0165] <30> The method for producing the sulfonate composition according to any one of <1> to <29> above, wherein the sum of p and q in the general formula (2) is 0 or more and 18 or less, 16 or less, 12 or less, 8 or less, 4 or less, 2 or less, 1 or less, or 0.

[0166] <31> The method for producing the sulfonate composition according to any one of <1> to <30> above, wherein the amount of the component (C) used relative to 1 mole of the component (A) is any one selected from greater than 1.00 mole, 1.05 mole or more, 1.10 mole or more, 1.13 mole or more, and is 1.17 mole or less.

[0167] <32> The method for producing the sulfonate composition according to any one of <1> to <31> above, wherein, during the sulfonation reaction, relative to 100 parts by mass of the component (A), the component (B1) is preferably used in an amount of 7 parts by mass or more, more preferably 7.5 parts by mass or more, further preferably 20 parts by mass or more, and preferably 380 parts by mass or less, more preferably 300 parts by mass or less, further preferably 216 parts by mass or less, still further preferably 199 parts by mass or less, still further preferably 100 parts by mass or less, still further preferably 85 parts by mass or less, still further preferably 75 parts by mass or less, still further preferably 60 parts by mass or less, still further preferably 55 parts by mass or less, still further preferably 51 parts by mass or less.

[0168] <33> The method for producing the sulfonate composition according to any one of <1> to <32> above, wherein, during the sulfonation reaction, relative to 100 parts by mass of the component (A), the component (B2) is preferably used in an amount of 2.0 parts by mass or more, more preferably 2.5 parts by mass or more, further preferably 3.0 parts by mass or more, and preferably 180 parts by mass or less, more preferably 120 parts by mass or less, further preferably 50 parts by mass or less, still further preferably 41 parts by mass or less, still further preferably 39 parts by mass or less, still further preferably 25 parts by mass or less, still further preferably 18 parts by mass or less, still further preferably 15 parts by mass or less.

[0169] <34> The method for producing the sulfonate composition according to any one of <1> to <33> above, wherein, during the sulfonation reaction, the mass ratio (B1) / (B2) of the amount of the component (B1) used to the amount of the component (B2) used is preferably 0.3 or more, more preferably 0.4 or more, further preferably 0.7 or more, still further preferably 0.9 or more, still further preferably 1.0 or more, still further preferably 2.0 or more, still further preferably 5.0 or more.

[0170] <35> The method for producing a sulfonate composition according to any one of <1> to <34> above, wherein after the sulfonation reaction, the concentration of the mixture obtained in the sulfonation reaction is adjusted using the component (B1) and / or the component (B2).

[0171] <36> The method for producing a sulfonate composition according to <35> above, wherein the mass ratio (B1) / (B2) of the content of the component (B1) to the content of the component (B2) in the mixture after the concentration adjustment is preferably 0.3 or more, more preferably 0.4 or more, further preferably 0.7 or more, still further preferably 0.9 or more, still further preferably 1.0 or more.

[0172] <37> The method for producing a sulfonate composition according to any one of <1> to <36> above, wherein based on 100 parts by mass of the component (A) before the sulfonation reaction, the content of the component (B1) in the mixture to be subjected to the removal of insoluble components is preferably 5 parts by mass or more, more preferably 7 parts by mass or more, further preferably 7.5 parts by mass or more, still further preferably 8 parts by mass or more, still further preferably 10 parts by mass or more, still further preferably 15 parts by mass or more, and preferably 380 parts by mass or less, more preferably 300 parts by mass or less, further preferably 216 parts by mass or less, still further preferably 200 parts by mass or less, still further preferably 199 parts by mass or less, still further preferably 100 parts by mass or less, still further preferably 85 parts by mass or less, still further preferably 75 parts by mass or less, still further preferably 65 parts by mass or less, still further preferably 60 parts by mass or less, still further preferably 55 parts by mass or less.

[0173] <38> The method for producing a sulfonate composition according to any one of <1> to <37> above, wherein in the mixture to be subjected to the removal of insoluble components, the content of the component (B1) is preferably 5% by mass or more, more preferably 7% by mass or more, and preferably 65% by mass or less, more preferably 60% by mass or less, further preferably 40% by mass or less, still further preferably 30% by mass or less, still further preferably 20% by mass or less.

[0174] <39> The method for producing a sulfonate composition according to any one of <1> to <38> above, wherein, based on 100 parts by mass of the component (A) before the sulfonation reaction, the content of the component (B2) in the mixture to which the removal of insoluble components is applied is preferably 5 parts by mass or more, more preferably 7 parts by mass or more, further preferably 15 parts by mass or more, still further preferably 25 parts by mass or more, and preferably 180 parts by mass or less, more preferably 120 parts by mass or less, further preferably 80 parts by mass or less, still further preferably 45 parts by mass or less, still further preferably 40 parts by mass or less, still further preferably 37 parts by mass or less, still further preferably 35 parts by mass or less, still further preferably 30 parts by mass or less.

[0175] <40> The method for producing a sulfonate composition according to any one of <1> to <39> above, wherein, in the mixture to which the removal of insoluble components is applied, the content of the component (B2) is preferably 3% by mass or more, more preferably 5% by mass or more, and preferably 40% by mass or less, more preferably 35% by mass or less, further preferably 30% by mass or less, still further preferably 26% by mass or less, still further preferably 25% by mass or less, still further preferably 22% by mass or less, still further preferably 20% by mass or less.

[0176] <41> The method for producing a sulfonate composition according to any one of <1> to <40> above, wherein, in the mixture to which the removal of insoluble components is applied, the mass ratio (B1) / (S + B1 + B2) of the content of the component (B1) to the total content of the components (S), (B1), and (B2) is 0.05 or more, preferably 0.09 or more, more preferably 0.10 or more, and 0.65 or less, preferably 0.59 or less, more preferably 0.55 or less, further preferably 0.50 or less, still further preferably 0.40 or less, still further preferably 0.35 or less.

[0177] <42> The method for producing a sulfonate composition according to any one of <1> to <41> above, wherein, in the mixture to which the removal of insoluble components is applied, the mass ratio (B2) / (S + B1 + B2) of the content of the component (B2) to the total content of the components (S), (B1), and (B2) is 0.03 or more, preferably 0.10 or more, and 0.26 or less, preferably 0.25 or less, more preferably 0.23 or less, further preferably 0.20 or less, still further preferably 0.18 or less.

[0178] <43>According to the method for producing a sulfonate composition described in any one of <1> to <42> above, in the mixture for removing insoluble components, the mass ratio (B1) / (B2) of the content of component (B1) to the content of component (B2) is preferably 0.3 or more, for example, 0.6 or more, 0.80 or more, 0.82 or more, 0.85 or more, 0.9 or more, and is 1000 or less, 100 or less, 50 or less, 30 or less, 20 or less, 10 or less, 5 or less, 2.5 or less, 2 or less.

[0179] <44>According to the method for producing a sulfonate composition described in any one of <1> to <43> above, one or more separation methods selected from the addition of an adsorption film, an adsorbent, a flocculant, centrifugation, standing, decantation, and filtration are used to remove the insoluble components from the mixture.

[0180] <45>According to the method for producing a sulfonate composition described in <44> above, the filtration is gravity filtration, pressure filtration, or vacuum filtration.

[0181] <46>According to the method for producing a sulfonate composition described in <44> or <45> above, one or more selected from a filter aid and a flocculant are used, and further, the filter aid is one or more selected from diatomaceous earth, silica, and glass fiber, to remove the insoluble components from the mixture.

[0182] <47>According to the method for producing a sulfonate composition described in <46> above, the addition amount of the filter aid is preferably 0.01 part by mass or more, more preferably 1 part by mass or more, and preferably 20 parts by mass or less, more preferably 10 parts by mass or less, based on every 100 parts by mass of the mixture for removing insoluble components.

[0183] <48>According to the method for producing a sulfonate composition described in any one of <1> to <47> above, in the mixture after removing insoluble components, the content of sodium sulfate is preferably 1.2% by mass or less, more preferably 0.8% by mass or less, further preferably 0.7% by mass or less, and even more preferably 0.5% by mass or less.

[0184] <49>According to the method for producing a sulfonate composition described in any one of <1> to <48> above, in the obtained sulfonate composition, the content of component (B1) is preferably 5% by mass or more, more preferably 10% by mass or more, further preferably 12% by mass or more, and preferably 65% by mass or less, more preferably 58% by mass or less, further preferably 35% by mass or less, and even more preferably 30% by mass or less.

[0185] <50>According to the method for producing a sulfonate composition described in any one of <1> to <49> above, in the obtained sulfonate composition, the content of component (B2) is preferably 2% by mass or more, more preferably 3% by mass or more, still more preferably 4% by mass or more, even more preferably 5% by mass or more, and preferably 30% by mass or less, more preferably 25% by mass or less, still more preferably 20% by mass or less.

[0186] <51>According to the method for producing a sulfonate composition described in <1> to <50> above, the obtained sulfonate composition preferably contains component (S) in an amount of 19% by mass or more, more preferably 50% by mass or more, still more preferably 55% by mass or more, and preferably 80% by mass or less, more preferably 70% by mass or less, still more preferably 68% by mass or less.

[0187] <52>According to the method for producing a sulfonate composition described in any one of <1> to <51> above, the obtained sulfonate composition preferably contains component (B) in an amount of 20% by mass or more, more preferably 25% by mass or more, still more preferably 45% by mass or more, and preferably 80% by mass or less, more preferably 45% by mass or less.

[0188] <53>According to the method for producing a sulfonate composition described in any one of <1> to <52> above, the following operations are performed: reacting (C) a sulfonating agent with (A) a compound represented by the following general formula (1) in the presence of at least one solvent selected from (B1) an organic solvent and (B2) water to obtain a mixture containing (S) a sulfonate represented by the following general formula (2); and removing insoluble components from the above mixture.

[0189] The mixture to which the removal of the insoluble components is applied contains component (S), component (B1), and component (B2). The mass ratio (B1) / (S + B1 + B2) of the content of component (B1) to the total content of component (S), component (B1), and component (B2) is 0.05 or more and 0.65 or less, preferably 0.59 or less.

[0190] The mass ratio (B2) / (S + B1 + B2) of the content of component (B2) to the total content of component (S), component (B1), and component (B2) is 0.03 or more and 0.26 or less, preferably 0.20 or less, and preferably the mass ratio (B1) / (B2) of the content of component (B1) to the content of component (B2) is 0.80 or more.

[0191] ROOC-(CH2) n -CH=CH-(CH2) m -COOR’ (1)

[0192] (In the formula, R and R' are independently groups selected from an alkyl group having 10 carbon atoms and an alkenyl group having 10 carbon atoms. n and m are each a number of 0 or more and 18 or less, and the sum of n and m is 0 or more and 18 or less.)

[0193] ROOC-(CH2) p -CH(SO3M)-CH2-(CH2) q -COOR’(2)

[0194] (In the formula, M is a cation, R and R' are independently groups selected from an alkyl group having 10 carbon atoms and an alkenyl group having 10 carbon atoms. p and q are each a number of 0 or more and 18 or less, and the sum of p and q is 0 or more and 18 or less.)

[0195] <54> According to the method for producing a sulfonate composition according to any one of <1> to <53> above, the following operations are carried out: in the presence of one or more solvents selected from (B) (B1) an organic solvent and (B2) water, reacting (C) a sulfonating agent with (A) a compound represented by the general formula (1) to obtain an operation of a mixture containing (S) a sulfonate represented by the following general formula (2); an operation of precipitating insoluble components from the mixture; and an operation of removing the components precipitated from the mixture,

[0196] The mixture to be subjected to the removal of the insoluble components contains (S) components, (B1) components, and (B2) components. The mass ratio (B1) / (S + B1 + B2) of the content of the (B1) components to the total content of the (S) components, (B1) components, and (B2) components is 0.05 or more and 0.65 or less, preferably 0.59 or less,

[0197] (The mass ratio (B2) / (S + B1 + B2) of the content of the (B2) components to the total content of the (S) components, (B1) components, and (B2) components is 0.03 or more and 0.26 or less, preferably 0.20 or less, and preferably the mass ratio (B1) / (B2) of the content of the (B1) components to the content of the (B2) components is 0.80 or more.)

[0198] ROOC-(CH2) n -CH=CH-(CH2) m -COOR’ (1)

[0199] (In the formula, R and R' are independently groups selected from an alkyl group having 10 carbon atoms and an alkenyl group having 10 carbon atoms. n and m are each a number of 0 or more and 18 or less, and the sum of n and m is 0 or more and 18 or less.)

[0200] ROOC-(CH2) p-CH(SO3M)-CH2-(CH2) q -COOR’(2)

[0201] (In the formula, M is a cation, and R and R’ are independently groups selected from an alkyl group having 10 carbon atoms and an alkenyl group having 10 carbon atoms. p and q are each a number of 0 or more and 18 or less, and the sum of p and q is 0 or more and 18 or less.)

[0202] <55> The method for producing a sulfonate composition according to any one of <1> to <54> above, wherein the insoluble component contains a (D) inorganic metal compound selected from the unreacted (C) component and the hydrolyzate of the (C) component.

[0203] <56> The method for producing a sulfonate composition according to any one of <1> to <55> above, wherein azeotropic distillation is not performed when removing the insoluble component.

[0204] <57> The method for producing a sulfonate composition according to any one of <1> to <56> above, wherein an organic solvent (B1) is not added to the sulfonate composition obtained by removing the insoluble component.

[0205] <58> The method for producing a sulfonate composition according to any one of <1> to <57> above, wherein the viscosity of the mixture to be subjected to the removal of the insoluble component at 20 °C is preferably 600 mPa·s or less, more preferably 500 mPa·s or less, still more preferably 470 mPa·s or less, and even more preferably 450 mPa·s or less.

[0206] <59> The method for producing a sulfonate composition according to any one of <1> to <58> above, wherein the viscosity of the mixture to be subjected to the removal of the insoluble component is, for example, 0.1 mPa·s or more, 1 mPa·s or more, or 10 mPa·s or more.

[0207] <60> The method for producing a sulfonate composition according to any one of <1> to <59> above, wherein the particle size of the (D) component captured during the removal operation of the insoluble component is 10 μm or less and 5 μm or less.

[0208] <61> The method for producing a sulfonate composition according to any one of <1> to <60> above, wherein the particle size of the (D) component captured during the removal operation of the insoluble component is preferably 0.1 μm or more, more preferably 1 μm or more.

[0209] <62>According to the method for producing a sulfonate composition described in any one of <1> to <61> above, the content of the component (D) in the sulfonate composition after removing insoluble components is less than 1.6 parts by mass with respect to 100 parts by mass of the content of the component (S), more preferably 1.5 parts by mass or less, and still more preferably 1.0 part by mass or less.

[0210] Examples

[0211] <Manufacturing Examples>

[0212] Diethyl maleate (di(2-propylheptyl) maleate (DDM)) was obtained according to Example 2 of the specification of U.S. Patent Application Publication No. 2007 / 0214999. In addition, maleic anhydride was changed to fumaric acid, and diethyl fumarate (di(2-propylheptyl) fumarate (DDF)) was obtained by the same operation.

[0213] <Step 1>

[0214] Then, the previous diethyl maleate (or diethyl fumarate), sodium metabisulfite, ion-exchanged water, and propylene glycol (PG) were added to a 1-L glass reaction vessel so as to have the compositions shown in Tables 1 to 3, and the reaction was carried out under the conditions shown in Tables 1 to 3 by a known method. In Examples 3 to 11, 13 to 20, and Comparative Examples 1 to 2, the same dialkyl sulfonate (DASS) as the dialkyl sulfonate produced in each example and comparative example was used in advance as a reaction promoter. It should be noted that in the following description, DASS includes not only the dialkyl sulfonate used as a reaction promoter but also the dialkyl sulfonate produced in the examples.

[0215] [Reagents Used]

[0216] · Sodium metabisulfite: manufactured by FUJIFILM Wako Pure Chemical Corporation, special grade reagent

[0217] · Propylene glycol: manufactured by FUJIFILM Wako Pure Chemical Corporation, special grade reagent

[0218] <Step 2>

[0219] Then, the mixture containing sulfonate obtained in Step 1 was cooled to 50°C or lower, and if necessary, propylene glycol and / or ion-exchanged water in the amounts shown in Tables 1 to 3 were added to the mixture.

[0220] <Step 3>

[0221] Then, while maintaining the mixture at 55°C or lower, the unreacted component (C) and / or the hydrolyzate of component (C) are oxidized with 30% aqueous hydrogen peroxide. Additionally, a 35% aqueous sodium hydroxide solution is added to the mixture to adjust the pH to 5. In the case where the neutralization step is performed first, after treating the unreacted component (C) and / or the hydrolyzate of component (C) with 20% sodium carbonate, it is oxidized with 30% aqueous hydrogen peroxide.

[0222] <Process 4>

[0223] Then, after adding Radiolite#900 (manufactured by Showa Chemical Industry Co., Ltd.) as a filter aid to the mixture, it is pressure-filtered with nitrogen at 0.4 MPa while circulating warm water at 50°C and maintaining the temperature in a jacketed pressure filter (internal volume 2.9 L, filtration area 0.0095 m 2 ) The captured particle size is 1 μm (value recorded in the filter aid catalog).

[0224] (1) Measurement method

[0225] For the sulfonate compositions obtained in Examples 1 to 20 and Comparative Examples 1 and 2, the content of each component was determined by the following method. The content of each component was measured immediately after filtration in Process 4. It should be noted that among the contents (mass%) of each component before filtration in Process 4, the contents of (S) DASS, (B1) PG, sodium sulfate, and (B2) water were calculated based on the feed amounts in Process 1, etc. Specifically, the content of (S) DASS was calculated by adding the added amount of DASS added as needed in Process 1 to the (S) component calculated based on the feed amount of component (A) and the conversion rate in the table. PG was calculated based on the feed amount in Process 1 and the added amount in Process 2. Sodium sulfate was the content obtained by calculating the remaining sodium metabisulfite based on the feed amount of sodium metabisulfite in Process 1 and the conversion rate in the table and converting the remaining sodium metabisulfite to sodium sulfate. (B2) Water was calculated as the balance of (S) DASS, (B1) PG, and sodium sulfate. The results are shown in Tables 1 to 3.

[0226] (1-1) Sulfonate (DASS) mass%

[0227] Determined in accordance with the synthetic detergent test method JIS K 3362.

[0228] (1-2) Bis(2-propylheptyl) fumarate mass%

[0229] Bis(2-propylheptyl) fumarate was quantified by gas chromatography.

[0230] (1-3) Propylene glycol mass%

[0231] Quantify propylene glycol using gas chromatography.

[0232] (1-4) Water mass %

[0233] Determine according to the moisture test method for chemicals JIS K 0068.

[0234] (1-5) Sodium sulfate mass %

[0235] Quantify sodium sulfate using the "Automatic potentiometric titrator" manufactured by Kyoto Electronics Industry Co., Ltd.

[0236] In addition, in Step 4, measure the viscosity at 20 °C of the mixture for filtration using a Type B rotational viscometer (Brookfield viscometer, manufactured by Toki Sangyo Co., Ltd.) with a No. 2 rotor.

[0237] (2) Evaluation method

[0238] (2-1) Evaluation of the content of inorganic metal compounds in the sulfonate composition

[0239] Determine the amount of sodium sulfate in each prepared sulfonate composition using the above method. The results are shown in Tables 1 to 3. If the content of sodium sulfate in each sulfonate composition immediately after Step 4 is 1.2 mass % or less, and further less than 0.8 mass %, it can be said that the sulfonate composition has a further reduced content of inorganic salt metal compounds.

[0240] (2-2) Inorganic salt reduction rate

[0241] Based on the content (mass %) of sodium sulfate before filtration and after filtration in Step 4, calculate the inorganic salt reduction rate using the following formula. The results are shown in Tables 1 to 3. It should be noted that in the following formula, "before filtration" represents the content (mass %) of sodium sulfate before filtration in Step 4, and "after filtration" represents the content (mass %) of sodium sulfate after filtration in Step 4.

[0242] Inorganic salt reduction rate (%) = [(before filtration - after filtration) / before filtration] × 100

[0243] (2-3) Ratio of inorganic salts to the (S) component

[0244] For the sulfonate composition after Step 4, evaluate each sulfonate composition based on the mass parts of sodium sulfate contained in the sulfonate composition relative to 100 mass parts of the (S) component contained in the sulfonate composition.

[0245] The smaller the mass parts of sodium sulfate relative to 100 mass parts of the (S) component, the higher the purity of the sulfonate composition can be said to be.

[0246] (2-4) Appearance evaluation

[0247] Add 30 g of the sulfonate composition after Step 4 to a sealable glass container (50 mL), and visually observe the appearance after storing at 20°C for 24 hours.

[0248] [Table 1]

[0249]

[0250] In Table 1, ※1, ※2: The parts by mass (addition amount or content) of the (B1) component and the (B2) component represent the parts by mass of the (B1) component or the (B2) component relative to 100 parts by mass of the (A) component, which is the raw material before the sulfonation reaction. The same applies to ※1 and ※2 in Tables 2 and 3 below.

[0251] [Table 2]

[0252]

[0253] [Table 3]

[0254]

[0255] As can be seen from Tables 1 to 3, according to the method for producing a sulfonate composition of the present invention, insoluble components (such as inorganic metal compounds such as sodium sulfate) in the sulfonate composition can be efficiently removed.

[0256] In addition, according to the method for producing a sulfonate composition of the present invention, the sulfonate represented by the general formula (2) of (S) can be contained at a high concentration, and the content of insoluble components (such as inorganic metal compounds such as sodium sulfate) relative to the content of the (S) component in the sulfonate composition can be effectively reduced.

Claims

1. A method for manufacturing a sulfonate composition, which performs the following operations: An operation of reacting component C with component A in the presence of component B to obtain a mixture containing component S; and An operation of removing insoluble components in the mixture without azeotropic distillation, Component A is a compound represented by the following general formula (1), component B is one or more solvents selected from component B1 and component B2, component B1 is propylene glycol, component B2 is water, component C is a sulfonating agent, and component S is a sulfonate represented by the following general formula (2), Relative to 1 mole of component A, the usage amount of component C is 1.00 mole or more and 1.20 moles or less, Component C is at least one compound selected from MHSO3, M2SO3, and M2S2O5, where M represents sodium or potassium, Before removing the insoluble components, the unreacted component C and / or its hydrolyzate in the mixture to be subjected to the removal of the insoluble components are oxidized and then neutralized, The mixture to be subjected to the removal of the insoluble components contains component S, component B1, and component B2, and the mass ratio (B1) / (S + B1 + B2) of the content of component B1 to the total content of component S, component B1, and component B2 is 0.09 or more and 0.65 or less, The mass ratio (B2) / (S + B1 + B2) of the content of component B2 to the total content of component S, component B1, and component B2 is 0.10 or more and 0.25 or less, The mass ratio (B1) / (B2) of the content of component B1 to the content of component B2 is 0.9 or more; ROOC-(CH2) n -CH=CH-(CH2) m -COOR’ (1) In the formula, R and R' are independently branched alkyl groups having 10 carbon atoms; n and m are each a number of 0 or more and 4 or less, and the sum of n and m is 0 or more and 4 or less; ROOC-(CH2) p -CH(SO3M)-CH2-(CH2) q -COOR’(2) In the formula, M is a cation, R and R' are independently branched alkyl groups having 10 carbon atoms; p and q are each a number of 0 or more and 4 or less, and the sum of p and q is 0 or more and 4 or less.

2. The method for manufacturing a sulfonate composition according to claim 1, wherein Component A is a compound in which R and R' in the general formula (1) are independently groups selected from 2-propylheptyl, 4-methyl-2-propylhexyl, and 5-methyl-2-propylhexyl.

3. The method for manufacturing a sulfonate composition according to claim 1 or 2, wherein After adding one or more solvents selected from component B1 and component B2 to the mixture, the insoluble components in the mixture are removed.

4. The method for manufacturing a sulfonate composition according to claim 1 or 2, wherein In the sulfonate composition, the content of component B1 is 5% by mass or more and 65% by mass or less, and the content of component B2 is 3% by mass or more and 25% by mass or less.

5. The method for manufacturing a sulfonate composition according to claim 1 or 2, wherein The insoluble components include component D, and component D is an inorganic metal compound selected from unreacted component C and the hydrolyzate of component C.

6. The method for manufacturing a sulfonate composition according to claim 1 or 2, wherein Component C is reacted with component A at a reaction temperature of 100 °C or more and less than 125 °C, under normal pressure or pressure.

7. The method for producing a sulfonate composition according to claim 1 or 2, wherein, A sulfonate obtained by reacting component A and component C is separately prepared, and component C and component A are reacted in the coexistence of the sulfonate.

8. The method for producing a sulfonate composition according to claim 1 or 2, wherein, In the sulfonate composition after removing the insoluble components, the content of component D is less than 1.6 parts by mass with respect to 100 parts by mass of the content of component S.

9. The method for producing a sulfonate composition according to claim 1, wherein, One or more than two kinds of component A are used.

10. The method for producing a sulfonate composition according to claim 1, wherein, Component A is a compound in which one or both of R and R' are 2-propylheptyl.

11. The method for producing a sulfonate composition according to claim 1, wherein, n and m in the general formula (1) are each 0 or more and 2 or less.

12. The method for producing a sulfonate composition according to claim 1, wherein, n and m in the general formula (1) are each 0 or more and 1 or less.

13. The method for producing a sulfonate composition according to claim 1, wherein, n and m in the general formula (1) are each 0.

14. The method for producing a sulfonate composition according to claim 1, wherein, The sum of n and m in the general formula (1) is 0 or more and 2 or less.

15. The method for producing a sulfonate composition according to claim 1, wherein, The sum of n and m in the general formula (1) is 0 or more and 1 or less.

16. The method for producing a sulfonate composition according to claim 1, wherein, The sum of n and m in the general formula (1) is 0.

17. The method for producing a sulfonate composition according to claim 1, wherein, Component C is sodium metabisulfite or potassium metabisulfite.

18. The method for producing a sulfonate composition according to claim 1, wherein, The insoluble components are removed from the mixture by one or more separation methods selected from the addition of an adsorption film, an adsorbent, a coagulant, centrifugation, standing, decantation, and filtration.

19. The method for producing a sulfonate composition according to claim 18, wherein, The filtration is gravity filtration, pressure filtration, or vacuum filtration.

20. The method for producing a sulfonate composition according to claim 18, wherein, One or more than one selected from a filter aid and a coagulant are used to remove the insoluble components from the mixture.

21. The method for producing a sulfonate composition according to claim 20, wherein, The addition amount of the filter aid is 0.01 part by mass or more and 20 parts by mass or less with respect to every 100 parts by mass of the mixture for removing the insoluble components.

22. The method for producing a sulfonate composition according to claim 20, wherein, The addition amount of the filter aid is 1 part by mass or more and 10 parts by mass or less with respect to every 100 parts by mass of the mixture for removing the insoluble components.

23. The method for producing a sulfonate composition according to claim 1, wherein, The obtained sulfonate composition contains component S in an amount of 19% by mass or more and 80% by mass or less.

24. The method for producing a sulfonate composition according to claim 1, wherein the resulting sulfonate composition contains an S component in an amount of 50% by mass or more and 70% by mass or less.

25. The method for producing a sulfonate composition according to claim 1, wherein the resulting sulfonate composition contains an S component in an amount of 55% by mass or more and 68% by mass or less.

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