Method for producing olefin sulfonic acid or salt thereof

Abstract

To provide a method for producing olefin sulfonic acid or a salt thereof that can suppress deterioration of the hue of the olefin sulfonic acid or salt thereof.SOLUTION: The method for producing an olefin sulfonic acid or a salt thereof of the present invention includes: a step (step A) of reacting one or more selected from an alkyl ether and an alkylbenzene with sulfur trioxide in a reaction apparatus and removing a reactant; a step (step B) of reacting an alcohol with sulfur trioxide in the reaction apparatus after the step A and removing a reactant; and a sulfonation step (step C) of reacting an olefin with sulfur trioxide in the reaction apparatus after the step B to obtain an olefin sulfonated product.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a process for producing an olefin sulfonic acid or a salt thereof. [Background technology]

[0002] Organic compound raw materials such as alkyl ethers, alkylbenzenes, alcohols, and olefins are sulfonated or sulfated with sulfur trioxide, and the resulting products are neutralized with alkali to be used as various anionic surfactants.

[0003] In the sulfonation or sulfate esterification of an organic compound raw material, there is a problem in that carbonaceous solid fouling is likely to adhere to the inside of the reaction apparatus.

[0004] In order to solve this problem, Patent Document 1 proposes a method for producing an anionic surfactant, which includes a step of supplying an organic compound raw material to a sulfonation or sulfate esterification apparatus and sulfonating or sulfate esterifying the raw material with sulfur trioxide gas, and is characterized in that an organic compound raw material other than higher alcohols is supplied to the sulfonation or sulfate esterification apparatus, and then higher alcohols are supplied thereto.

[0005] Furthermore, Patent Document 2 proposes a method for cleaning a sulfonation or sulfate esterification apparatus, which sulfonates or sulfates organic compounds with sulfur trioxide gas, characterized in that dirt adhering to the apparatus is cleaned with higher alcohols. [Prior art documents] [Patent documents]

[0006] [Patent Document 1] JP 2000-136398 A [Patent Document 2] JP 2000-129293 A Summary of the Invention [Problem to be solved by the invention]

[0007] Usually, the sulfonation or sulfate esterification of organic compound raw materials is carried out continuously by sequentially supplying various organic compound raw materials to a reaction apparatus from the viewpoint of improving production efficiency.

[0008] However, it has been found that when an alkyl ether, an alkyl benzene, or a mixture thereof is supplied to a reactor and sulfated or sulfonated with sulfur trioxide to produce an alkyl ether sulfate, an alkyl benzene sulfonic acid, or a mixture thereof, and then an olefin is subsequently supplied to the reactor and sulfonated with sulfur trioxide to produce an olefin sulfonic acid, the color of the olefin sulfonic acid or a salt thereof is significantly deteriorated.

[0009] It is believed that when an alkyl ether is supplied to a reactor and sulfated with sulfur trioxide to produce alkyl ether sulfuric acid, and then an olefin is supplied to the reactor and sulfonated with sulfur trioxide to produce olefin sulfonic acid, precipitates are generated due to the low compatibility between alkyl ether and olefin, which makes the reaction between the olefin and sulfur trioxide uneven, resulting in the production of colored substances such as polymers having many double bonds, causing the olefin sulfonic acid or its salt to become colored.

[0010] In addition, it is presumed that when alkylbenzene is supplied to a reactor and sulfonated with sulfur trioxide to produce alkylbenzene sulfonic acid, the reaction between the olefin compound and sulfur trioxide becomes non-uniform because the reactivities of alkylbenzene compounds and olefin compounds are extremely different, resulting in the production of colored substances such as polymers having many double bonds, which causes the olefin sulfonic acid or a salt thereof to become colored.

[0011] In either case, it is believed that the cause of the discoloration is different from the "carbonaceous solid dirt" described as a problem in Patent Document 1 or Patent Document 2.

[0012] The present invention relates to a method for producing an olefin sulfonic acid or a salt thereof, which can suppress deterioration in the hue of the olefin sulfonic acid or a salt thereof. [Means for solving the problem]

[0013] As a result of extensive research, the present inventors have found that the above-mentioned problems can be solved by sulfonating or sulfate-esterifying various organic compound raw materials in a specific order.

[0014] That is, the present invention relates to a process for producing ... After step A, a step (step B) of reacting alcohol with sulfur trioxide in the reaction apparatus and removing the reaction product; After step B, a sulfonation step (step C) is included in which an olefin is reacted with sulfur trioxide in the reactor to obtain an olefin sulfonate. The present invention relates to a method for producing an olefin sulfonic acid or a salt thereof.

[0015] That is, according to the present invention, in a continuous surfactant production method including the production of one or more surfactants selected from alkyl ether sulfuric acid, alkyl benzene sulfonic acid, and salts thereof (step A), the production of one or more surfactants selected from alkyl sulfuric acid and salts thereof (step B), and the production of olefin sulfonic acid or a salt thereof (step C), after the step A, the sulfonation step C is carried out subsequent to the step B using the same reaction apparatus used in these steps, thereby making it possible to produce an olefin sulfonic acid or a salt thereof having a good hue.

[0016] Furthermore, if the sulfonation step C is carried out immediately after the step A, the alkyl ether, etc., which is the raw material of step A, will be mixed into the olefin, which is the raw material of the sulfonation step C, and since the alkyl ether, etc. has poor compatibility with the olefin, or since the alkyl ether, etc. and the olefin have different reactivities with sulfur trioxide, the olefin containing the alkyl ether, etc. will easily clog the piping, which is considered to cause a disruption in the production process. On the other hand, according to the production method of the present invention, by providing step B between step A and the sulfonation step C, the alkyl ether, etc. will not easily be mixed into the olefin, and therefore the continuous production process will not easily be disrupted. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0017] <Process A> In step A, one or more selected from alkyl ether and alkyl benzene are reacted with sulfur trioxide in a reactor, and a reaction product is taken out. After step A, other steps may be included, or step B may be performed without including other steps.

[0018] The alkyl ether is not particularly limited, and examples thereof include compounds represented by the following general formula (1-1).

[0019] R 1 -(OA) p -OH (1-1) (In the formula, R 1 is an alkyl group, A is an alkylene group having 2 to 4 carbon atoms, and p is the number of OA.

[0020] R 1The alkyl group is not particularly limited, and is, for example, an alkyl group having 8 to 24 carbon atoms. Specific examples of the alkyl group include linear alkyl groups such as octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, icosyl, henicosyl, docosyl, tricosyl, and tetracosyl groups; and branched alkyl groups such as isooctyl, 2-ethylhexyl, isononyl, isodecyl, isoundecyl, isododecyl, isotridecyl, isotetradecyl, isopentadecyl, isohexadecyl, isoheptadecyl, isooctadecyl, isononadecyl, isoicosyl, isohenicosyl, isodocosyl, isotricosyl, and isotetracosyl groups.

[0021] The number p of OA is not particularly limited, and may be, for example, an integer of 1 to 20, or a real number of 0.5 to 20 indicating an average number.

[0022] By reacting the compound represented by the above general formula (1-1) with sulfur trioxide, the alkyl ether is converted into a sulfate ester, and an alkyl ether sulfate represented by the following general formula (1-2) is obtained.

[0023] R 1 -(OA) p -OSO3H (1-2) (In the formula, R 1 , A and p are the same as above.

[0024] The alkylbenzene is not particularly limited, but examples thereof include compounds represented by the following general formula (2-1).

[0025] R 2 -Ph (2-1) (In the formula, R 2 is an alkyl group, and Ph is a phenyl group which may have a substituent.

[0026] R 2The alkyl group in is not particularly limited, but is, for example, an alkyl group having 8 to 24 carbon atoms. 1 The straight chain alkyl group and the branched alkyl group described above are included.

[0027] The substituent that Ph may have is not particularly limited, and examples thereof include an alkyl group having 1 to 3 carbon atoms, a hydroxyl group, and a phenoxy group.

[0028] By reacting the alkylbenzene represented by the above general formula (2-1) with sulfur trioxide, the alkylbenzene is sulfonated to obtain an alkylbenzenesulfonic acid represented by the following general formula (2-2).

[0029] R 2 -Ph-SO3H (2-2) (In the formula, R 2 and Ph are the same as above.)

[0030] The sulfur trioxide used in step A is not particularly limited, but is preferably sulfur trioxide gas from the viewpoint of improving reactivity. The sulfur trioxide gas used in step A is not particularly limited, but it is preferable to use sulfur trioxide gas diluted with an inert gas such as air or nitrogen to about 1 to 30% by volume, preferably 1.5% by volume or more and 10% by volume or less.

[0031] The reaction apparatus is not particularly limited, and may be a batch reaction apparatus or a continuous reaction apparatus, but from the viewpoint of improving productivity, a continuous reaction apparatus is preferable. As the continuous reaction apparatus, for example, a reactor equipped with a tank reactor, a falling film reactor, a rising film reactor, a tubular gas-liquid mixed phase flow reactor, or the like, is used. From the viewpoint of reacting a liquid such as the alkyl ether, the alkylbenzene, the alcohol or the olefin described below with gaseous sulfur trioxide, a preferred reactor is a thin film reactor equipped with an external jacket.

[0032] In the reaction of the alkyl ether with sulfur trioxide, the amount of sulfur trioxide used per mole of alkyl ether is preferably 0.900 moles or more, more preferably 0.920 moles or more, and even more preferably 0.940 moles or more from the viewpoint of improving the yield of alkyl ether sulfuric acid, and is preferably 1.040 moles or less, more preferably 1.020 moles or less, and even more preferably 1.000 moles or less from the viewpoint of producing a sulfate ester salt having a good hue and a small amount of inorganic salts. In addition, when a thin-film reactor equipped with an external jacket is used, the temperature of the cooling water passed through the jacket at the upper stage of the reactor is preferably 20° C. or more, more preferably 30° C. or more, and even more preferably 35° C. or more from the viewpoint of improving the yield of alkyl ether sulfuric acid, and is preferably 70° C. or less, more preferably 60° C. or less from the viewpoint of producing a sulfate ester salt having a good hue and a small amount of inorganic salts. The temperature of the cooling water passed through the jacket at the lower stage of the reactor is preferably 0° C. or higher, more preferably 5° C. or higher, from the viewpoint of improving the yield of alkyl ether sulfate, and is preferably 40° C. or lower, more preferably 30° C. or lower, and even more preferably 25° C. or lower, from the viewpoint of producing a sulfate ester salt having a good hue and a small amount of inorganic salts.

[0033] The amount of sulfur trioxide used per mole of the alkyl ether can also be controlled by the flow rates of the raw material (alkyl ether) and sulfur trioxide gas fed into the reactor. In this case, it is necessary to use sulfur trioxide gas whose concentration is controlled to a constant level. By controlling the sulfur trioxide gas concentration to a constant level, the flow rate ratio (raw material flow rate / sulfur trioxide gas flow rate) can be converted into the molar ratio used (molar amount of raw material / molar amount of sulfur trioxide gas).

[0034] In addition, in the reaction between the alkylbenzene and sulfur trioxide, the amount of sulfur trioxide used per mole of alkylbenzene is preferably 0.950 moles or more, more preferably 0.970 moles or more, and even more preferably 0.990 moles or more from the viewpoint of improving the yield of alkylbenzenesulfonic acid, and is preferably 1.090 moles or less, more preferably 1.070 moles or less, and even more preferably 1.050 moles or less from the viewpoint of producing a sulfonated product having a good hue. In addition, when a thin-film reactor equipped with an external jacket is used, the temperature of the cooling water passed through the jacket at the upper stage of the reactor is preferably 0° C. or more, more preferably 3° C. or more, and even more preferably 5° C. or more from the viewpoint of improving the yield of alkylbenzenesulfonic acid, and is preferably 60° C. or less, more preferably 50° C. or less from the viewpoint of producing a sulfonated product having a good hue. The temperature of the cooling water passed through the jacket at the lower stage of the reactor is preferably 0° C. or higher, more preferably 3° C. or higher, from the viewpoint of improving the yield of alkylbenzenesulfonic acid, and is preferably 40° C. or lower, more preferably 30° C. or lower, and even more preferably 25° C. or lower, from the viewpoint of producing a sulfonated product having a good hue.

[0035] The amount of sulfur trioxide used per mole of alkylbenzene can also be controlled by the flow rates of the raw material (alkylbenzene) and sulfur trioxide gas fed into the reactor. In this case, it is necessary to use sulfur trioxide gas whose concentration is controlled to a constant level. By controlling the sulfur trioxide gas concentration to a constant level, the flow rate ratio (flow rate of raw material / flow rate of sulfur trioxide gas) can be converted into the molar ratio used (molar amount of raw material / molar amount of sulfur trioxide gas).

[0036] The resulting alkyl ether sulfate, alkyl benzene sulfonate, or mixture thereof may be used as an anionic surfactant as it is, or may be neutralized with an alkali compound to form an alkyl ether sulfate represented by the following general formula (1-3), an alkyl benzene sulfonate represented by the following general formula (2-3), or a mixture thereof, which may be used as an anionic surfactant.

[0037] {R 1-(OA) p --OSO3} m M (1-3) (In the formula, R 1 , A and p are the same as above. M is a cation, and m is the valence of M.

[0038] {R 2 -Ph-SO3} m M (2-3) (In the formula, R 2 and Ph are the same as above. M is a cation, and m is the valence of M.

[0039] The cation of M is not particularly limited, and examples thereof include alkali metal ions, alkaline earth metal ions, and ammonium ions. Examples of alkali metal ions include sodium ions and potassium ions. Examples of alkaline earth metal ions include magnesium ions and calcium ions. Examples of ammonium ions include alkanol ammonium and alkyl ammonium. Examples of alkanol ammonium include monoalkanol ammonium such as monoethanol ammonium, dialkanol ammonium such as diethanol ammonium, and trialkanol ammonium such as triethanol ammonium. Examples of alkyl ammonium include monoalkyl ammonium, dialkyl ammonium, trialkyl ammonium, and tetraalkyl ammonium.

[0040] Step A may be one step of a method for producing one or more compounds selected from alkyl ether sulfuric acid, alkyl benzene sulfonic acid, and salts thereof.

[0041] <Process B> Step B is a step of reacting alcohol with sulfur trioxide in the reaction apparatus after step A and taking out a reaction product. After step B, step C may be carried out without or with another step within a range that does not affect the quality of the olefin sulfonic acid or a salt thereof produced in step C. It is preferable to carry out step C without including another step.

[0042] The alcohol is not particularly limited, and examples thereof include compounds represented by the following general formula (3-1).

[0043] R 3 -OH (3-1) (In the formula, R 3 is an alkyl group.

[0044] R 3 The alkyl group in is not particularly limited, but is, for example, an alkyl group having 8 to 24 carbon atoms. 1 The straight chain alkyl group and the branched alkyl group described above are included.

[0045] By reacting the alcohol represented by the above general formula (3-1) with sulfur trioxide, the alcohol is converted into a sulfate ester to obtain an alkyl sulfate represented by the following general formula (3-2).

[0046] R 3 -OSO3H (3-2) (In the formula, R 3 is the same as above.)

[0047] The sulfur trioxide used in step B is not particularly limited, and may be the same as or different from the sulfur trioxide used in step A. From the viewpoint of improving reactivity, the sulfur trioxide used in step B is preferably sulfur trioxide gas. When sulfur trioxide gas is used in steps A and B, from the viewpoint of improving reactivity, the sulfur trioxide gas used in step B may be the same as the gas used in step A, or may be a gas with a different dilution degree.

[0048] The reaction apparatus used in the above step A is used.

[0049] In the reaction of the alcohol with sulfur trioxide, the amount of sulfur trioxide used per mole of alcohol is preferably 0.910 moles or more, more preferably 0.930 moles or more, and even more preferably 0.950 moles or more from the viewpoint of improving the yield of alkyl sulfuric acid, and is preferably 1.050 moles or less, more preferably 1.030 moles or less, and even more preferably 1.010 moles or less from the viewpoint of producing a sulfate ester salt having a good hue and a small amount of inorganic salts. In addition, when a thin-film reactor equipped with an external jacket is used, the temperature of the cooling water passed through the jacket at the upper stage of the reactor is preferably 20° C. or more, more preferably 30° C. or more, and even more preferably 35° C. or more from the viewpoint of improving the yield of alkyl sulfuric acid, and is preferably 70° C. or less, more preferably 60° C. or less from the viewpoint of producing a sulfate ester salt having a good hue and a small amount of inorganic salts. The temperature of the cooling water passed through the jacket at the lower stage of the reactor is preferably 0° C. or higher, more preferably 5° C. or higher, from the viewpoint of improving the yield of alkyl sulfuric acid, and is preferably 40° C. or lower, more preferably 30° C. or lower, and even more preferably 25° C. or lower, from the viewpoint of producing a sulfate ester salt having a good hue and a small amount of inorganic salts.

[0050] The amount of sulfur trioxide used per mole of alcohol can also be controlled by the flow rates of the raw material (alcohol) and sulfur trioxide gas fed into the reaction apparatus. In this case, it is necessary to use sulfur trioxide gas whose concentration is controlled to a constant level. By controlling the sulfur trioxide gas concentration to a constant level, the flow rate ratio (raw material flow rate / sulfur trioxide gas flow rate) can be converted into the molar ratio (molar amount of raw material / molar amount of sulfur trioxide gas) used.

[0051] The resulting alkyl sulfate may be used as an anionic surfactant as it is, or may be neutralized with an alkali compound to form an alkyl sulfate salt represented by the following general formula (3-3), which may then be used as an anionic surfactant.

[0052] {R 3 --OSO3}m M (3-3) (In the formula, R 3 , M and m are the same as above.

[0053] Step B may be one step of a method for producing one or more compounds selected from alkyl sulfuric acids and salts thereof.

[0054] [Method of producing olefin sulfonic acid or its salt] The method for producing an olefin sulfonic acid or a salt thereof of the present invention includes a sulfonation step C of reacting an olefin with sulfur trioxide to obtain an olefin sulfonate, and is characterized in that the sulfonation step C is carried out in the reaction apparatus after the step A and subsequent to the step B.

[0055] <Sulfonation step C> The sulfonation step C is a step in which an olefin is reacted with sulfur trioxide in the reaction apparatus to sulfonate the olefin to produce an olefin sulfonate.

[0056] The olefin is not particularly limited, and examples thereof include α-olefins and internal olefins. Here, α-olefins are olefins in which the double bond is present at the end of the carbon chain, i.e., the double bond is present at the 1st position of the carbon chain. Furthermore, internal olefins are olefins in which the double bond is present inside the carbon chain, i.e., the double bond is present at the 2nd or higher position of the carbon chain. These may be used alone or in combination of two or more.

[0057] The carbon number of the olefin such as an α-olefin or an internal olefin is preferably 10 or more, more preferably 12 or more, and even more preferably 14 or more, from the viewpoint of improving the cleaning performance when the olefin sulfonic acid and its salt are used as an anionic surfactant, and is preferably 22 or less, and more preferably 18 or less.

[0058] The olefin is preferably an internal olefin from the viewpoint of improving the cleaning performance when the olefin sulfonic acid or a salt thereof is used as an anionic surfactant. From the viewpoint of improving the cleaning performance and foaming performance when the internal olefin sulfonic acid or a salt thereof is used as an anionic surfactant, the internal olefin preferably contains 48 mass% or less, more preferably 35 mass% or less, of olefins having a double bond at the 2-position, and from the viewpoint of improving the productivity of the internal olefin, the internal olefin preferably contains 10 mass% or more, more preferably 15 mass% or more.

[0059] In the present invention, the olefin sulfonic acid is a sulfonated product obtained by sulfonating the above-mentioned olefin.

[0060] In the present invention, the olefin sulfonate is a sulfonate obtained by sulfonating the olefin and then neutralizing it. That is, when the olefin is sulfonated, it is converted into a sultone and an olefin sulfonic acid, which are further converted into a hydroxysulfonate and an olefin sulfonate in a neutralization step or the like. The obtained product is mainly a mixture of these. In the present invention, these products and the mixture thereof are collectively referred to as olefin sulfonate.

[0061] In the present invention, the internal olefin sulfonic acid is a sulfonated product obtained by sulfonating the internal olefin.

[0062] In the present invention, the internal olefin sulfonate is a sulfonate obtained by sulfonating the internal olefin and further neutralizing it. That is, when the internal olefin is sulfonated, it is converted into β-sultone, γ-sultone, and olefin sulfonic acid, which are further converted into hydroxysulfonate and olefin sulfonate in a neutralization step or the like. The obtained product is mainly a mixture of these. In the present invention, these products and the mixture thereof are collectively referred to as internal olefin sulfonate.

[0063] The olefins can be produced by known methods, for example, the methods described in WO 2011 / 052732.

[0064] The olefin is reacted with sulfur trioxide to sulfonate the olefin, thereby obtaining an olefin sulfonate.

[0065] The sulfur trioxide used in the sulfonation step C is not particularly limited, and may be the same as or different from the sulfur trioxide used in the step A or the step B. The sulfur trioxide used in the sulfonation step C is preferably sulfur trioxide gas from the viewpoint of improving reactivity. When sulfur trioxide gas is used in the step A and the sulfonation step C, or in the step B and the sulfonation step C, the sulfur trioxide gas used in the sulfonation step C may be the same as the gas used in the step A or the step B, or may be a gas with a different dilution degree, from the viewpoint of improving reactivity.

[0066] The reaction apparatus used in the above steps A and B is used.

[0067] In the sulfonation step C, the amount of sulfur trioxide used per mole of olefin is preferably 0.920 moles or more, more preferably 0.940 moles or more, and even more preferably 0.960 moles or more from the viewpoint of improving the yield of olefinsulfonic acid, and is preferably 1.060 moles or less, more preferably 1.040 moles or less, and even more preferably 1.020 moles or less from the viewpoint of producing a sulfonate salt having a good hue and a small amount of inorganic salts. When a thin-film reactor equipped with an external jacket is used, the temperature of the cooling water passed through the jacket at the upper stage of the reactor is preferably 0° C. or more, more preferably 3° C. or more, and even more preferably 5° C. or more from the viewpoint of improving the yield of olefinsulfonic acid, and is preferably 50° C. or less, more preferably 40° C. or less from the viewpoint of producing a sulfonate salt having a good hue and a small amount of inorganic salts. The temperature of the cooling water passed through the jacket at the lower stage of the reactor is preferably 0° C. or higher, more preferably 3° C. or higher, from the viewpoint of improving the yield of olefin sulfonic acid, and is preferably 40° C. or lower, more preferably 30° C. or lower, and even more preferably 25° C. or lower, from the viewpoint of producing a sulfonate ester salt having a good hue and a small amount of inorganic salts.

[0068] The amount of sulfur trioxide used per mole of olefin can also be controlled by the flow rates of the raw material (olefin) and sulfur trioxide gas fed into the reactor. In this case, it is necessary to use sulfur trioxide gas whose concentration is controlled to a constant level. By controlling the sulfur trioxide gas concentration to a constant level, the flow rate ratio (flow rate of raw material / flow rate of sulfur trioxide gas) can be converted into the molar ratio (molar amount of raw material / molar amount of sulfur trioxide gas) used.

[0069] The resulting olefin sulfonate (olefin sulfonic acid) may be used as an anionic surfactant as it is, or may be neutralized with an alkali compound to form an olefin sulfonate salt, which may then be used as an anionic surfactant.

[0070] <Neutralization process of olefin sulfonate> The method for producing an olefin sulfonic acid or a salt thereof of the present invention may include a step of mixing the olefin sulfonated product obtained in the sulfonation step C with an alkali compound to produce a neutralized product.

[0071] The alkali compound used for neutralization may be an inorganic alkali compound or an organic alkali compound. As the inorganic alkali compound, for example, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, and alkali metal carbonates such as sodium carbonate and potassium carbonate can be used. As the organic alkali compound, for example, an amine compound having 1 to 6 carbon atoms such as ammonia and 2-aminoethanol can be used.

[0072] From the viewpoints of availability and economy, the alkaline compound used for neutralization is preferably an inorganic alkaline compound, more preferably an alkali metal hydroxide, still more preferably at least one selected from sodium hydroxide and potassium hydroxide, and even more preferably sodium hydroxide.

[0073] The alkaline compound used for neutralization is preferably used as an alkaline aqueous solution from the viewpoint of improving handling. The concentration of the alkaline aqueous solution is preferably 1% by mass or more, more preferably 4.5% by mass or more, even more preferably 7% by mass or more, still more preferably 10% by mass or more, and even more preferably 12% by mass or more from the viewpoint of economic efficiency and suppressing the generation of impurities such as internal olefins and inorganic salts. Also, from the viewpoint of improving productivity in the hydrolysis step, it is preferably 30% by mass or less, more preferably 25% by mass or less, even more preferably 23% by mass or less, still more preferably 20% by mass or less, and even more preferably 15% by mass or less.

[0074] The amount of the alkali compound added is preferably 1 molar or more, more preferably 1.03 molar or more, relative to the sulfonic acid groups of the olefin sulfonation product, from the viewpoint of suppressing the formation of impurities such as olefins, inorganic salts, etc. and from the viewpoint of improving reactivity, and is preferably 2.5 molar or less, more preferably 2.0 molar or less, and even more preferably 1.5 molar or less, from the viewpoint of economy and suppressing the formation of impurities such as internal olefins, inorganic salts, etc.

[0075] In the neutralization step, the concentration of the olefin sulfonate in the mixture is preferably 15% by mass or more, more preferably 30% by mass or more, even more preferably 40% by mass or more, still more preferably 45% by mass or more, still more preferably 48% by mass or more, and still more preferably 50% by mass or more from the viewpoint of suppressing the generation of impurities such as olefins and inorganic salts due to the decomposition reaction of the olefin sulfonate, and is preferably 75% by mass or less, more preferably 70% by mass or less, still more preferably 65% ​​by mass or less, and still more preferably 60% by mass or less from the viewpoint of suppressing the heat of neutralization. Here, the concentration of the olefin sulfonate in the neutralization step is the sum of the concentration of the unneutralized olefin sulfonate and the concentration of the neutralized olefin sulfonate converted into the olefin sulfonate.

[0076] In the neutralization step, the temperature when the olefin sulfonation product is mixed with the alkaline aqueous solution and the temperature during the neutralization reaction are 40° C. or lower, preferably 35° C. or lower, more preferably 30° C. or lower, and even more preferably 25° C. or lower, from the viewpoint of suppressing the production of impurities such as internal olefins and inorganic salts due to side reactions, and are preferably 0° C. or higher, more preferably 10° C. or higher, even more preferably 15° C. or higher, and even more preferably 20° C. or higher, from the viewpoint of improving reactivity.

[0077] In the neutralization step, any type of mixer may be used as long as it can efficiently mix the olefin sulfonated product and the alkaline aqueous solution and apply shear force to the oily material. Examples of such mixers include static mixers, collision mixers, impeller mixers, and vibration mixers. Examples of static mixers include a static mixer manufactured by Noritake. Examples of impingement mixers include a high-pressure emulsifier manufactured by Nanomizer. Examples of impeller mixers include a Milder manufactured by Matsubo and a Homoxer manufactured by Primix. Among these, impeller mixers are preferred from the viewpoint of equipment cost.

[0078] From the viewpoint of suppressing the production of by-products and improving productivity, the neutralization step is preferably carried out by a so-called continuous method in which the olefin sulfonated product and the alkaline aqueous solution are added while circulating the reaction liquid using a loop reactor, and the reaction liquid is simultaneously withdrawn.

[0079] In the neutralization step, the neutralization time is preferably 5 minutes or more, more preferably 10 minutes or more, and even more preferably 15 minutes or more from the viewpoint of sufficiently carrying out the neutralization reaction, and is preferably 100 minutes or less, more preferably 50 minutes or less, and even more preferably 20 minutes or less from the viewpoint of improving productivity.

[0080] In the case of a continuous method, the neutralization time can be expressed as an average residence time obtained by dividing the volume of the loop reactor by the total amount of the internal olefin sulfonate and the aqueous alkaline solution added per unit time. The average residence time is preferably 8 minutes or more, more preferably 10 minutes or more, and even more preferably 12 minutes or more from the viewpoint of suppressing neutralization heat, and is preferably 60 minutes or less, more preferably 30 minutes or less, more preferably 20 minutes or less, and even more preferably 15 minutes or less from the viewpoint of improving productivity. In addition, in the case of a continuous method, the circulation ratio of the reaction liquid is preferably 3 times or more, more preferably 6 times or more, and even more preferably 9 times or more from the viewpoint of improving reactivity, and is preferably 30 times or less, more preferably 20 times or less, and even more preferably 15 times or less from the viewpoint of suppressing a pressure rise in the reactor. Here, the circulation ratio is the ratio of the total content volume circulating in the reactor to the flow rate input into the reactor, and is expressed as (total circulation amount in the reactor) / (input amount into the reactor).

[0081] In the neutralization step, water-soluble organic solvents such as alcohol and acetone, and surfactants such as polyoxyethylene alkyl ether can be allowed to coexist. Such coexisting substances are preferably not used because they may deteriorate during the neutralization reaction, remain in the final product, or impose a burden on the purification step, and when used, are preferably used in an amount of 20% by mass or less in the mixed liquid, more preferably 10% by mass or less, even more preferably 2% by mass or less, and even more preferably 1% by mass or less.

[0082] The neutralization product obtained in the step of neutralizing the olefin sulfonation product may be further subjected to hydrolysis.

[0083] <Hydrolysis process> The method for producing an olefin sulfonic acid or a salt thereof of the present invention may include a hydrolysis step of hydrolyzing the neutralization product.

[0084] In the hydrolysis step, the temperature during hydrolysis is preferably 120° C. or higher, more preferably 140° C. or higher, and even more preferably 160° C. or higher, from the viewpoint of improving reactivity, and is preferably 220° C. or lower, more preferably 180° C. or lower, from the viewpoint of suppressing decomposition of the product.

[0085] The hydrolysis reaction may be carried out in a batch reactor or in a continuous reactor.

[0086] The treatment time for the hydrolysis step is preferably 30 minutes or more, more preferably 45 minutes or more, from the viewpoint of completing the reaction, and is preferably 4 hours or less, more preferably 3 hours or less, even more preferably 2 hours or less, and still more preferably 90 minutes or less, from the viewpoint of improving productivity.

[0087] The concentration of the olefin sulfonate aqueous solution obtained by the hydrolysis step is preferably 15 mass% or more, more preferably 30 mass% or more, even more preferably 40 mass% or more, still more preferably 45 mass% or more, still more preferably 48 mass% or more, and still more preferably 50 mass% or more, from the viewpoint of improving the productivity, and is preferably 75 mass% or less, more preferably 70 mass% or less, still more preferably 65 mass% or less, and still more preferably 60 mass% or less, from the viewpoint of improving the viscosity of the aqueous solution, etc.

[0088] The olefin sulfonic acid or a salt thereof can be used for various applications as it is, but may be further purified by desalting, decolorization, etc.

[0089] The olefin sulfonic acid or a salt thereof produced by the sulfonation step following the step B after the step A has a very good color compared to those produced by conventional methods.

[0090] The present invention and preferred embodiments thereof are described below.

[0091] <1> a step of reacting one or more selected from an alkyl ether and an alkyl benzene with sulfur trioxide in a reactor and extracting a reaction product (step A); After step A, a step (step B) of reacting alcohol with sulfur trioxide in the reaction apparatus and removing the reaction product; After step B, a sulfonation step (step C) is included in which an olefin is reacted with sulfur trioxide in the reactor to obtain an olefin sulfonate. A method for producing olefin sulfonic acid or a salt thereof. <2> The alkyl ether is represented by the following general formula (1-1): <1> 2. A method for producing the olefin sulfonic acid or a salt thereof according to claim 1 . R 1 -(OA) p -OH (1-1) (In the formula, R 1 is an alkyl group, A is an alkylene group having 2 to 4 carbon atoms, and p is the number of OA. <3> R 1 is an alkyl group having 8 to 24 carbon atoms; <2> 2. A method for producing the olefin sulfonic acid or a salt thereof according to claim 1 . <4> The number p of OA is an integer of 1 to 20, or a real number of 0.5 to 20 indicating an average number; <2> or <3> 2. A method for producing the olefin sulfonic acid or a salt thereof according to claim 1 . <5> The alkylbenzene is represented by the following general formula (2-1): <1> ~ <4> 13. A method for producing the olefin sulfonic acid or a salt thereof according to claim 12. R 2 -Ph (2-1) (In the formula, R 2 is an alkyl group, and Ph is a phenyl group which may have a substituent. <6> R 2 is an alkyl group having 8 to 24 carbon atoms; <5> 2. A method for producing the olefin sulfonic acid or a salt thereof according to claim 1 . <7> The substituent that may be contained in Ph is, for example, an alkyl group having 1 to 3 carbon atoms, a hydroxyl group, a phenoxy group, etc. <5> or <6> 2. A method for producing the olefin sulfonic acid or a salt thereof according to claim 1 . <8> The alcohol is represented by the following general formula (3-1): <1> ~ <7> 13. A method for producing the olefin sulfonic acid or a salt thereof according to claim 12. R 3 -OH (3-1) (In the formula, R 3 is an alkyl group. <9> R 3 is an alkyl group having 8 to 24 carbon atoms; <8> 2. A method for producing the olefin sulfonic acid or a salt thereof according to claim 1 . <10> The sulfur trioxide used in step A is preferably sulfur trioxide gas. <1> ~ <9> 13. A method for producing the olefin sulfonic acid or a salt thereof according to claim 12. <11> The sulfur trioxide gas used in the step A is diluted with an inert gas such as air or nitrogen to about 1 to 30% by volume, preferably 1.5% by volume or more and 10% by volume or less. <10> 2. A method for producing the olefin sulfonic acid or a salt thereof according to claim 1 . <12> The reaction apparatus may be a batch reaction apparatus or a continuous reaction apparatus, and is preferably a continuous reaction apparatus, such as a tank reactor; a thin film reactor such as a falling film reactor, a rising film reactor, and a tubular gas-liquid mixed phase flow reactor; <1> ~ <11> 13. A method for producing the olefin sulfonic acid or a salt thereof according to claim 12. <13> The step A is one step of a method for producing one or more compounds selected from alkyl ether sulfuric acid, alkyl benzene sulfonic acid, and salts thereof. <1> ~ <12> 13. A method for producing the olefin sulfonic acid or a salt thereof according to claim 12. <14> The sulfur trioxide used in step B is the same as or different from the sulfur trioxide used in step A. Also, when sulfur trioxide gas is used in steps A and B, the sulfur trioxide gas used in step B is the same as the gas used in step A or is a gas with a different dilution degree. <1> ~ <13> 13. A method for producing the olefin sulfonic acid or a salt thereof according to claim 12. <15> The step B is one step of a method for producing one or more compounds selected from alkyl sulfuric acid and salts thereof. <1> ~ <14> 3. A method for producing an olefin sulfonic acid or a salt thereof according to any one of the preceding claims. <16> The olefin is an α-olefin or an internal olefin; <1> ~ <15> 13. A method for producing the olefin sulfonic acid or a salt thereof according to claim 12. <17> The number of carbon atoms in the olefin is preferably 10 or more, more preferably 12 or more, and even more preferably 14 or more, and is preferably 22 or less, and more preferably 18 or less. <1> ~ <16> 13. A method for producing the olefin sulfonic acid or a salt thereof according to claim 12. <18> The olefin is an internal olefin. <1> ~ <17> 13. A method for producing the olefin sulfonic acid or a salt thereof according to claim 12. <19> The sulfur trioxide used in the sulfonation step C is the same as or different from the sulfur trioxide used in the step A or the step B, and when sulfur trioxide gas is used in the step A and the sulfonation step C, or in the step B and the sulfonation step C, the sulfur trioxide gas used in the sulfonation step C is the same gas as the gas used in the step A or the step B, or is a gas with a different dilution degree. <1> ~ <18> 13. A method for producing the olefin sulfonic acid or a salt thereof according to claim 12. <20> In the sulfonation step C, the amount of sulfur trioxide used per mole of olefin is preferably 0.920 moles or more, more preferably 0.940 moles or more, even more preferably 0.960 moles or more, and is preferably 1.060 moles or less, more preferably 1.040 moles or less, even more preferably 1.020 moles or less. <1> ~ <19> 13. A method for producing the olefin sulfonic acid or a salt thereof according to claim 12. <21> In the sulfonation step C, the temperature of the cooling water passed through the jacket at the upper stage of the reactor is preferably 0° C. or higher, more preferably 3° C. or higher, and even more preferably 5° C. or higher, and is preferably 50° C. or lower, and more preferably 40° C. or lower. <1> ~ <20> 13. A method for producing the olefin sulfonic acid or a salt thereof according to claim 12. <22> In the sulfonation step C, the temperature of the cooling water passed through the jacket at the lower stage of the reactor is preferably 0° C. or higher, more preferably 3° C. or higher, and is preferably 40° C. or lower, more preferably 30° C. or lower, and even more preferably 25° C. or lower. <1> ~ <21> 13. A method for producing the olefin sulfonic acid or a salt thereof according to claim 12. <23> A neutralization step of mixing the olefin sulfonated product obtained in the sulfonation step C with an alkali compound to produce a neutralization product. <1> ~ <22> 13. A method for producing the olefin sulfonic acid or a salt thereof according to claim 12. <24> The alkali compound is an inorganic alkali compound or an organic alkali compound. Examples of the inorganic alkali compound include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, and alkali metal carbonates such as sodium carbonate and potassium carbonate. Examples of the organic alkali compound include amine compounds having 1 to 6 carbon atoms, such as ammonia and 2-aminoethanol. <23> 2. A method for producing the olefin sulfonic acid or a salt thereof according to claim 1 . <25> The alkali compound is preferably an inorganic alkali compound, more preferably an alkali metal hydroxide, even more preferably at least one selected from sodium hydroxide and potassium hydroxide, and even more preferably sodium hydroxide. <23> 2. A method for producing the olefin sulfonic acid or a salt thereof according to claim 1 . <26> The alkaline compound is preferably used as an alkaline aqueous solution, and the concentration of the alkaline aqueous solution is preferably 1% by mass or more, more preferably 4.5% by mass or more, even more preferably 7% by mass or more, still more preferably 10% by mass or more, still more preferably 12% by mass or more, and is preferably 30% by mass or less, more preferably 25% by mass or less, still more preferably 23% by mass or less, still more preferably 20% by mass or less, and still more preferably 15% by mass or less. <23> ~ <25> 13. A method for producing the olefin sulfonic acid or a salt thereof according to claim 12. <27> The amount of the alkali compound added is preferably 1 mole or more, more preferably 1.03 mole or more, and is preferably 2.5 mole or less, more preferably 2.0 mole or less, and even more preferably 1.5 mole or less, based on the sulfonic acid groups of the olefin sulfonation product. <23> ~ <26> 13. A method for producing the olefin sulfonic acid or a salt thereof according to claim 12. <28> The neutralization step is carried out in a continuous process. <23> ~ <27> 13. A method for producing the olefin sulfonic acid or a salt thereof according to claim 12. <29> Further, the method includes a hydrolysis step of hydrolyzing the neutralization product. <23> ~ <28> 13. A method for producing the olefin sulfonic acid or a salt thereof according to claim 12. <30> In the hydrolysis step, the temperature during hydrolysis is preferably 120° C. or higher, more preferably 140° C. or higher, even more preferably 160° C. or higher, and is preferably 220° C. or lower, more preferably 180° C. or lower. <29> 2. A method for producing the olefin sulfonic acid or a salt thereof according to claim 1 . <31> The hydrolysis step may be carried out in a batch reactor or in a continuous reactor. <29> or <30> 2. A method for producing the olefin sulfonic acid or a salt thereof according to claim 1 . <32> Furthermore, purification such as desalting and decolorization of the olefin sulfonic acid or its salt is performed. <1> ~ <31> 13. A method for producing the olefin sulfonic acid or a salt thereof according to claim 12. <33> The method for producing one or more compounds selected from alkyl ether sulfuric acid, alkylbenzene sulfonic acid, and salts thereof, wherein the step A is one step of a method for producing one or more compounds selected from alkyl ether sulfuric acid, alkylbenzene sulfonic acid, and salts thereof. <34> The method for producing one or more compounds selected from alkyl sulfuric acid and salts thereof, wherein the step B is one step of a method for producing one or more compounds selected from alkyl sulfuric acid and salts thereof. EXAMPLES

[0092] The present invention will be specifically described below based on examples. In addition, unless otherwise specified in the table, the content of each component is expressed as mass %. In addition, the evaluation and measurement methods are as follows.

[0093] <Method for evaluating the color of internal olefin sulfonic acid> The produced internal olefin sulfonic acid (IOS) was diluted 5 times by mass with ethanol to prepare an ethanol solution containing 20% ​​by mass of internal olefin sulfonic acid. The prepared ethanol solution was placed in a glass cell with an optical path length of 10 mm, and the absorbance at a wavelength of 420 nm was measured using a spectrophotometer "UV-1800" (manufactured by Shimadzu Science Co., Ltd.). The obtained absorbance was multiplied by 1000 to obtain the Klett value, which represents the hue.

[0094] <Method for measuring the position of double bonds in internal olefins> The double bond positions of the internal olefins were measured by gas chromatography (hereafter abbreviated as GC). Specifically, the internal olefins were reacted with dimethyl disulfide to form dithiolated derivatives, and each component was then separated by GC. The double bond positions of the internal olefins were determined from the peak areas of each. The equipment and analytical conditions used for the measurements were as follows: GC equipment "HP6890" (manufactured by Hewlett Packard), column "Ultra-Alloy-1HT capillary column" (30m x 250μm x 0.15μm, manufactured by Frontier Labs), detector (hydrogen flame ionization detector (FID)), injection temperature 300℃, detector temperature 350℃, He flow rate 4.6mL / min.

[0095] Manufacturing Example 1 Synthesis of alkyl ethoxylates 995g of linear alcohol "Kalcol 2098" (Kao Corporation) with 12 carbon atoms and 3.0g of KOH were charged into an autoclave equipped with a stirrer, temperature controller, and automatic feeder, and dehydration was carried out for 30 minutes at 110°C and 1.3kPa. After dehydration, nitrogen replacement was carried out, and the temperature was raised to 150°C, and 471g of ethylene oxide was charged. An addition reaction and maturation were carried out at 150°C. Then, after cooling to 80°C, 3.3g of acetic acid was added to the autoclave. After stirring for 30 minutes at 80°C, the mixture was discharged to obtain an alkyl ethoxylate (average EO 2.0 moles added).

[0096] Manufacturing Example 2 Synthesis of internal olefin with carbon number of 16 (C2 position 30.7% by mass) A flask equipped with a stirrer was charged with 7000g (28.9 moles) of 1-hexadecanol "Kalcol 6098" (Kao Corporation) and 700g (10% by mass based on the raw material alcohol) of γ-alumina (STREM Chemicals, Inc.) as a solid acid catalyst, and the reaction was carried out for 3 hours at 280°C while circulating nitrogen (7000mL / min.) through the system under stirring. After the reaction was completed, the alcohol conversion rate was 100%, and the C16 internal olefin purity was 99.6%. The obtained crude internal olefin was transferred to a distillation flask and distilled at 136-160°C / 4.0mmHg to obtain an internal olefin with a carbon number of 16 and an olefin purity of 100%. The double bond distribution of the obtained internal olefin was 0.6 mass% at C1, 30.7 mass% at C2, 26.1 mass% at C3, 18.8 mass% at C4, 10.5 mass% at C5, 6.7 mass% at C6, and 6.6 mass% in total at C7 and C8.

[0097] Production Example 3 Synthesis of internal olefin with carbon number of 18 (C2 position 25.0 mass%) A flask equipped with a stirrer was charged with 7000g (25.9 moles) of 1-octadecanol "Kalcol 8098" (Kao Corporation) and 700g (10% by mass based on the raw material alcohol) of γ-alumina (STREM Chemicals, Inc.) as a solid acid catalyst, and the reaction was carried out for 10 hours at 280°C while circulating nitrogen (7000mL / min.) through the system under stirring. After the reaction was completed, the alcohol conversion rate was 100%, and the C18 internal olefin purity was 98.2%. The obtained crude internal olefin was transferred to a distillation flask and distilled at 148-158°C / 0.5mmHg to obtain an internal olefin with a carbon number of 18 and an olefin purity of 100%. The double bond distribution of the obtained internal olefin was 0.5 mass% at C1, 25.0 mass% at C2, 22.8 mass% at C3, 19.1 mass% at C4, 14.0 mass% at C5, 7.4 mass% at C6, 5.4 mass% at C7, and 5.8 mass% in total at C8 and C9.

[0098] Production Example 4 Preparation of internal olefin with carbon numbers of 16 / 18 (mass ratio 79.3 / 20.7) 15 kg of a C16 / C18 internal olefin (mass ratio 79.3 / 20.7) was obtained by mixing 11.9 kg of the internal olefin having 16 carbon atoms synthesized in Production Example 2 and 3.1 kg of the internal olefin having 18 carbon atoms synthesized in Production Example 3. The double bond distribution of the obtained internal olefin was 0.6 mass% at C1, 29.5 mass% at C2, 25.4 mass% at C3, 18.9 mass% at C4, 11.2 mass% at C5, 6.9 mass% at C6, 3.7 mass% at C7, and 3.8 mass% in total at C8 and C9.

[0099] Example 1 A thin-film reactor with an external jacket having an inner diameter of 14 mm and a length of 4 m, which had been washed with water and dried with heated air, was used. The temperature of the cooling water passing through the jacket at the upper stage of the reactor was 40°C, and the temperature of the cooling water passing through the jacket at the lower stage of the reactor was 20°C. The alkyl ethoxylate obtained in Production Example 1 was allowed to flow down as a thin film along the wall of the reactor as a raw material, and sulfur trioxide gas diluted to 2.0% by volume with dehumidified air was added to the reactor to carry out a sulfuric acid esterification reaction for 2 hours to obtain alkyl ether sulfate (AES) (Step A). ​​The AES obtained in Step A was taken out of the reactor. Here, 0.97 moles of sulfur trioxide were used per mole of alkyl ethoxylate. Next, the raw material was switched to a linear alcohol having 12 carbon atoms, "Kalcol 2098" (manufactured by Kao Corporation), and a sulfate esterification reaction was carried out for 2 hours to obtain alkyl sulfate (AS) (Step B). The AS obtained in Step B was taken out from the reactor. Here, 0.98 moles of sulfur trioxide were used per mole of linear alcohol having 12 carbon atoms, and the temperature of the cooling water passed through the jacket at the upper stage of the reactor was set to 40°C, and the temperature of the cooling water passed through the jacket at the lower stage of the reactor was set to 20°C. Thereafter, the raw material was switched to the internal olefin obtained in Production Example 4, and the sulfonation reaction was carried out for 2 hours to obtain internal olefin sulfonic acid (IOS) (sulfonation step C). Here, 1.01 mol of sulfur trioxide was used per mol of the internal olefin, and the temperatures of the cooling water passed through the upper and lower jackets of the reactor were both set to 10°C. All the raw materials were fed at a constant rate of 75 g / min. The IOS color immediately after the feedstock was switched to internal olefins and after 2 hours of operation were evaluated by the above method. The evaluation results are shown in Table 1.

[0100] Example 2 Step A, step B, and sulfonation step C were carried out in the same manner as in Example 1, except that in step A, linear alkylbenzene "Alkene L" (manufactured by JX Nippon Oil & Energy Corporation) was supplied instead of alkyl ethoxylate, 1.04 moles of sulfur trioxide was used per mole of linear alkylbenzene, and the temperatures of the cooling water passed through the upper and lower jackets of the reactor were both set to 10°C to carry out the sulfonation reaction to obtain alkylbenzene sulfonic acid (LAS). The IOS color immediately after the feedstock was switched to internal olefins and after 2 hours of operation were evaluated by the above method. The evaluation results are shown in Table 1.

[0101] Comparative Example 1 Step A and the sulfonation step C were carried out in the same manner as in Example 1, except that step B was not carried out. The IOS color immediately after the feedstock was switched to internal olefins and after 2 hours of operation were evaluated by the above method. The evaluation results are shown in Table 1.

[0102] Comparative Example 2 Step A and the sulfonation step C were carried out in the same manner as in Example 2, except that step B was not carried out. The IOS color immediately after the feedstock was switched to internal olefins and after 2 hours of operation were evaluated by the above method. The evaluation results are shown in Table 1.

[0103] Reference example 1 The reactor described in Example 1 was washed with water and dried with heated air. Then, the internal olefin obtained in Production Example 4 was allowed to flow down along the wall of the reactor in the form of a thin film, and sulfur trioxide gas diluted with dehumidified air was added to the reactor to carry out a sulfonation reaction for 2 hours to obtain internal olefin sulfonic acid (IOS). Here, 1.01 mol of sulfur trioxide was used per mol of the internal olefin, and the temperature of the cooling water passed through the jackets at the upper and lower stages of the reactor was both 10°C. The IOS hue immediately after the start of sulfonation and after 2 hours of operation were evaluated by the above method. The evaluation results are shown in Table 1.

[0104] [Table 1] [Industrial Applicability]

[0105] The olefin sulfonic acid or a salt thereof of the present invention can be suitably used as a surfactant in cleaning agents and the like.

Claims

1. A step of reacting one or more selected from an alkyl ether and an alkyl benzene with sulfur trioxide in a reactor and extracting a reaction product (step A); After step A, a step (step B) of reacting alcohol with sulfur trioxide in the reaction apparatus and removing the reaction product; After step B, a sulfonation step (step C) is performed in which an olefin is reacted with sulfur trioxide in the reactor to obtain an olefin sulfonate. A method for producing olefin sulfonic acid or a salt thereof.

2. The method for producing an olefin sulfonic acid or a salt thereof according to claim 1, wherein the alkyl ether is represented by the following general formula (1-1): 2 １ -(9) ｐ -92 (1-1) (In the formula, R １ is an alkyl group, A is an alkylene group having 2 to 4 carbon atoms, and p is the number of OA.

3. The method for producing an olefin sulfonic acid or a salt thereof according to claim 1 or 2, wherein the alkylbenzene is represented by the following general formula (2-1): R ２ -Ph (2-1) (In the formula, R ２ is an alkyl group, and Ph is a phenyl group which may have a substituent.

4. The method for producing an olefin sulfonic acid or a salt thereof according to any one of claims 1 to 3, wherein the alcohol is represented by the following general formula (3-1): R ３ -OH (3-1) (In the formula, R ３ is an alkyl group.)

5. The method for producing an olefin sulfonic acid or a salt thereof according to any one of claims 1 to 4, wherein the olefin has 10 or more and 22 or less carbon atoms.

6. The method for producing an olefin sulfonic acid or a salt thereof according to any one of claims 1 to 5, wherein the olefin is an internal olefin.

7. The method for producing an olefin sulfonic acid or a salt thereof according to any one of claims 1 to 6, wherein the sulfur trioxide used in the step A is sulfur trioxide gas.

8. The method for producing an olefin sulfonic acid or a salt thereof according to any one of claims 1 to 7, wherein the sulfur trioxide used in the step B is sulfur trioxide gas.

9. The method for producing an olefin sulfonic acid or a salt thereof according to any one of claims 1 to 8, wherein the sulfur trioxide used in the sulfonation step C is sulfur trioxide gas.

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