CN102746078A - Preparation method for organic sulfonic acid compound - Google Patents
Preparation method for organic sulfonic acid compound Download PDFInfo
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Abstract
The present invention discloses a preparation method for an organic sulfonic acid compound. An organic sulfonate can react with a soluble silver salt to produce an insoluble organic silver sulfonate precipitate; after filtration, a halogen acid is added to the organic silver sulfonate precipitate, and halogen ions react with silver ions to produce a low solubility silver halide precipitate; filtration is performed to remove the insoluble silver halide; and the resulting filtrate is distilled to remove the solvent to obtain the organic sulfonic acid compound. With the present invention, the case of difficult acidification of the organic sulfonate having poor dissolubility in water at the normal temperature is overcome, and the method is applicable for most of the organic sulfonates, and can be applied in fields of surfactant synthesis, water-soluble dye synthesis, ion exchange resin synthesis, medicine synthesis, food additive synthesis, and the like.
Description
Technical field
The present invention relates to a kind of preparation method of organic sulfonic acid compounds.Particularly relate to a kind of method for preparing the organic sulfonic acid compounds from organic sulfonate.
Background technology
The organic sulfonic acid compounds; Generally have characteristics such as water-soluble, acid, emulsification, moistening and foaming; Can be widely used in synthetic surfactant, water-soluble dye, flavouring agent, ion exchange resin and some medicines; Sulfonic group can also further be converted into groups such as hydroxyl, amino, sulphonamide simultaneously, is the important intermediate in the Fine Chemical Industry, and is therefore closely related with our life.The preparation method of organic sulfonic acid compounds commonly used has:
1. the aromatics and the vitriol oil, oleum, sulphur trioxide, chlorsulfonic acid reaction obtain aryl sulfonic acid compounds (CN 101723858A), and this reaction is that reversible reaction need be used a large amount of vitriol oils or the moisture constantly removed wherein just can reach good productive rate.
2. aliphatic hydrocarbon obtains the fatty group sulfonic compound through the sulphonating agent sulfonation; Sulphonating agent commonly used has (US 3479398) such as oleum, sulphur trioxide, sulfurous gas, chlorsulfonic acids; Because the various c h bonds in the aliphatic hydrocarbon all sulfonation reaction can take place, therefore be difficult to obtain single fatty group sulfoacid compound.
3. organic compounds containing sulfur such as mercaptan, thioether, disulphide, lsothiocyanates etc. obtain the organic sulfonic acid compounds through peroxo-, and oxygenant commonly used is (CN 1165136A) such as hydrogen peroxide, bromine water, potassium permanganate, concentrated nitric acid, chromic acid.
4. organic SULPHURYL CHLORIDE obtains the organic sulfonic acid compound through heating hydrolysis.This method requires the water-soluble relatively good of raw material, and equipment acidproof (US 2228598).
5. aldehyde, ketone, epoxy alkane etc. obtain hydroxyl sulfoacid sodium with the S-WAT addition, and the acidified processing of this sodium sulfonate obtains hydroxyl sulfoacid compounds (J.Am.Chem.Soc.1954,4094).
6. alkene or alkynes and sodium sulfite anhy 96 addition obtain organic sulfonic acid sodium, the acidified organic sulfonic acid compound (US 3150169) that obtains of this sodium sulfonate.
7. halohydrocarbon and S-WAT generation substitution reaction obtain organic sulfonic acid sodium, and the further acidifying of organic sulfonic acid sodium obtains organic sulfonic acid compound (CN 101875623A).
The souring method that organic sulfonate is commonly used is: in the aqueous solution of organic sulfonate, feed strong acid (vitriol oil or hydrochloric acid gas) acidifying (CN 101219975A); Perhaps obtain organic sulfonic acid compound (J.Am.Chem.Soc.1959,2997) through the ion exchange resin acidifying then with organic sulfonate is soluble in water.Utilize strong acid acidifying method, the amount ratio of acid is bigger, requires equipment that stronger acid-resistant corrosion is arranged, and the meeting of aftertreatment simultaneously produces a large amount of inorganic salt, obtain relatively difficulty of the higher organic sulfonic acid of purity.Utilize ion-exchange-resin process acidifying cleaning easy; But treatment capacity is limited; Scale operation is restricted; Utilize under the ion-exchange-resin process acidifying requirement organic sulfonate room temperature solvability in water better on the other hand, then be difficult to carry out acidifying for the organic sulfonate that solubleness is low in water under the room temperature.
Summary of the invention
In order to overcome above-mentioned defective of the prior art, the invention provides a kind of preparation method of organic sulfonic acid compounds.This method has overcome some organic sulfonates owing to poorly soluble in water is difficult to the situation that acidifying becomes the organic sulfonic acid compounds, can both be suitable for for most organic sulfonate.
The objective of the invention is to realize through following technical scheme:
A kind of preparation method of organic sulfonic acid compounds contains and has the following steps:
(1) uses organic sulfonate and the silver salt shown in the formula I to be dissolved in the solvent, obtain organic sulfonic acid silver after the reaction;
(2) in step (1), add the haloid acid reaction in the organic sulfonic acid silver of gained, remove insolubles, obtain the organic sulfonic acid compounds shown in the formula II;
G-SO
3M G-SO
3H
(formula I) (formula II)
Wherein: group G is a kind of in alkyl, aryl, heterocyclic radical, substituted alkyl, substituted aryl or the substituted heterocyclic radical; Substituting group is one or more in the substituted radical of carbon containing, fluorine, chlorine, bromine, iodine, oxygen, sulphur, nitrogen, phosphorus or silicon; Be preferably methyl, ethyl, propyl group, sec.-propyl, butyl, fluorine, chlorine, bromine, iodine, trifluoromethyl, trifluoroethyl, trichloromethyl, hydroxyl, carboxyl, ester group, aldehyde radical, methoxyl group, oxyethyl group, sulfydryl, thioether group, sulphur NCO, nitro, amino, N, one or more in N-dimethylamino, cyanic acid, phosphate, the phosphate-based or siloyl group; M is: basic metal, earth alkali metal or subgroup metal; Said silver salt is a soluble silver salt.
Group G is preferably a kind of in alkyl, aryl, substituted alkyl or the substituted aryl; Group G further is preferably relatively poor alkyl, aryl, substituted alkyl or the substituted aryl of its sulphonate solvability in water under the normal temperature; As: dodecyl, tetradecyl, fluoro nonyl, trimethyl silicon based hexyl, diphenyl-methyl, benzyl, cyclohexyl, 6-methoxyl group hexyl, chloro decyl, N, N-dimethyl-g alkyl, 4-p-methoxy-phenyl, xenyl, 4-tert-butyl-phenyl, triethyl phenyl, trifluoromethyl or tetramethylphenyl etc.
Wherein, when M is basic metal, be preferably lithium, sodium, potassium or caesium; When M is earth alkali metal, be preferably magnesium, calcium, strontium or barium; When M is the subgroup metal, be preferably iron, copper or zinc.
Because the silver salt of solubility helps silver ions and the sulfonate ion reaction generates organic sulfonic acid silver deposition.Used soluble silver salt among the present invention is preferably Silver Nitrate, tachyol, silver perchlorate, Silver monoacetate or two ammoniums and closes in the silver one or more.Consider complicacy, and the problem of by product aftertreatment, further be preferably Silver Nitrate, tachyol, silver perchlorate, Silver monoacetate or two ammoniums among the present invention and close a kind of in the silver at the aspects such as calculating of charging capacity.
Used solvent is one or more in water or the polar organic solvent among the present invention; Wherein, consider to have fat-soluble organic group and water miscible sulfonate groups in the organic sulfonate that the solvent of therefore being selected for use must have solvability preferably to these two kinds of groups under the condition of normal temperature or heating, the solubleness of raw material is increased.Polar organic solvent among the present invention is preferably methyl alcohol, ethanol, propyl alcohol, Virahol, butanols, acetone, methyl ethyl ketone, ETHYLE ACETATE, ether, methyl ethyl ether, acetonitrile, THF, 1; 4-dioxane, N; In dinethylformamide, DMAC N,N, DMSO 99.8MIN., formic acid, acetate, Nitromethane 99Min., terepthaloyl moietie, Ucar 35, USP Kosher or the glycol ether one or more.Polar organic solvent further is preferably methyl alcohol, ethanol, Virahol, terepthaloyl moietie, acetone, acetonitrile, THF, 1,4-dioxane, DMSO 99.8MIN., N, one or more in dinethylformamide or the DMAC N,N.
The temperature of organic sulfonate and silver salt reaction is preferably 0-200 ℃ in the step of the present invention (1), and further preferred temperature of reaction is 20-150 ℃.Because temperature is lower than 0 ℃, it is slow speed of response to occur, the situation that yield is low; When temperature is higher than 200 ℃, solvent boiling point may occurs and not reach, the situation that solvent is evaporated.Suitable heating can improve the solubleness of raw material, adds the speed of fast response.
The time of organic sulfonate and silver salt reaction is preferably 1 minute to 48 hours in the step of the present invention (1), and the further preferred reaction times is 5 minutes to 10 hours.
In the step of the present invention (1) in the theoretical feed ratio of organic sulfonate and silver salt and the organic sulfonate valency of salt ion relevant; Can make the fully reaction of organic sulfonic acid silver for the excessive slightly silver salt of the relatively poor organic sulfonate of solvability, excessive greatly silver salt then is a kind of waste.Therefore the molar ratio of organic sulfonate and silver salt total amount is preferably 1: (1-5), further preferred feed ratio is 1: (1-2).
When organic sulfonic acid silver was lower than 0 ℃ with the haloid acid temperature of reaction in the step of the present invention (2), it was slow speed of response to occur, the situation that yield is low; Temperature is higher than 200 ℃, most of solvent may occur and be evaporated easily, the situation that organic sulfonic acid decomposes easily.Therefore organic sulfonic acid silver is preferably 0-200 ℃ with the temperature of haloid acid reaction, and further preferred temperature of reaction is 20-150 ℃.
Organic sulfonic acid silver is 1 minute to 48 hours with the time of haloid acid reaction in the step of the present invention (2), and the preferred reaction times is 15 minutes to 10 hours.Reaction times, too short reaction was insufficient, and the reaction times, long influence to reaction yield was little.
Organic sulfonic acid silver is preferably 1 with the molar ratio of haloid acid total amount in the step of the present invention (2): (1-50), further preferred feed ratio is 1: (1-10).
The used haloid acid of the present invention is one or more in hydrochloric acid, Hydrogen bromide or the hydroiodic acid HI.Hydrofluoric acid in the haloid acid is gas, and tachyol is solvable, therefore can not be used for reaching the purpose for preparing the organic sulfonic acid compounds with the reaction of organic sulfonic acid silver.Hydrochloric acid, Hydrogen bromide or hydroiodic acid HI can generate Silver monochloride, Silver monobromide or the Silver monoiodide of indissoluble with the silver ions reaction, therefore can obtain the organic sulfonic acid compounds.
The present invention utilizes the solubleness of organic sulfonic acid silver less; At first organic sulfonic acid silver is precipitated out; Utilize the silver halide solubleness lower principle more silver-colored then than organic sulfonic acid; In organic sulfonic acid silver, add haloid acid, silver ions is cemented out the silver halide precipitation that forms indissoluble, obtain corresponding organic sulfonic acid compounds simultaneously.
Can use the present invention for most of organic sulfonate acidifying for the organic sulfonic acid compounds; Especially under the normal temperature in water poorly soluble organic sulfonate; When being difficult to, use the present invention also can obtain corresponding organic sulfonic acid compounds with direct acidization or ion-exchange-resin process acidifying.
The organic sulfonic acid compounds of the present invention's preparation can be applied to fields such as synthetic surfactant, water-soluble dye, ion exchange resin, medicine, high molecular polymer.
Embodiment
Solvent, soluble silver salt, organic sulfonate used among the embodiment be analytically pure product, purchases in traditional Chinese medicines group.
Water is deionized water, utilizes the ion exchange resin self-control.
Product among the embodiment
1H NMR adopts JEOL 400MHz nuclear-magnetism to measure, and measures the solvent of usefulness and selects for use deuterochloroform, deuterated methanol or deuterium for water.
Through embodiment the present invention is further explained below, but the present invention is not limited in embodiment.
The preparation of 1: ten seven fluorine decane of embodiment sulfonic acid
17 fluorine decane sodium sulfonate 200mg are dissolved in the 15ml methyl alcohol; Silver Nitrate 74mg is dissolved in 10ml methyl alcohol; Add in the 17 fluorine decane sodium sulfonate solution silver nitrate solution and constantly stirring, the adularescent solid is separated out gradually, and cooling off and in reaction solution, adding the about 30ml of entry gradually has more deposition to produce.Filtration obtains little yellow solid, in this solid, adds 1mol/L hydrochloric acid soln 5ml, is heated to 50 ℃ and stirs 5 hours, removes by filter insoluble solid wherein, and filtrate steaming removal solvent gets 17 fluorine decane sulfonic acid.
1H?NMR(400MHz，CD
3OD)δ2.58-2.72(m，2H)，2.99-3.03(m，2H)
Embodiment 2: the preparation of dodecyl sodium sulfonate
In the 30ml deionized water, add in the 2.72g sodium laurylsulfonate, heat this suspension liquid to 70 ℃, after 20 minutes, the sodium laurylsulfonate solid dissolves fully, and solution becomes must be clarified.1.7g Silver Nitrate solid is dissolved in the 50ml deionized water, then this silver nitrate solution is added in the sodium dodecyl sulfate solution while hot, behind the generation white precipitate, this reaction soln continues heating 2 hours at 70 ℃.Utilize centrifugal separation to obtain white solid.This solid is hanged turbid in the 20ml deionized water, and is heated to 70 ℃. in suspension liquid, slowly add the aqueous hydrochloric acid of 1mol/L.After regulating pH value to 1, cooling reaction liquid filters to room temperature, and the water in the filtrating is removed in underpressure distillation, obtains 1.21g dodecyl sodium sulfonate (yield 44%).
1H?NMR(400MHz，D
2O)δ0.85-0.86(m，3H)，1.28-1.38(m，18H)，1.73(br，2H)，2.83-2.85(br，2H)
The preparation of embodiment 3:2-p diethylaminobenzoic acid ester group ethyl sulfonic acid
2-p diethylaminobenzoic acid ester group ethyl sulfonic acid lithium 252mg is dissolved in 10ml water, and Silver monoacetate 167mg is dissolved in the 10ml water, both is mixed stirring adularescent solid separate out; Continue to stir 2 hours; Filtration obtains white solid, in this white solid, adds 1mol/L hydrochloric acid 10ml, is heated to 50 ℃ and stirs 2 hours; Remove by filter insoluble solids, filtrate steaming removal solvent obtains 2-p diethylaminobenzoic acid ester group ethyl sulfonic acid.
1H?NMR(400MHz，CDCl
3)δ1.05(t，J＝6.4Hz，6H)，1.98(m，2H)，2.75(m，2H)，3.93(m，4H)
The preparation of 4: two benzene methanesulfonic acids of embodiment
Hexichol methanesulfonic sodium 270mg, tachyol 127mg is dissolved in respectively in the 20ml methyl alcohol; Mix back adularescent solid and separate out, stirring at room 2 hours is filtered and is obtained white solid; In this white solid, add lmol/L Hydrogen bromide 5ml; Be heated to 50 ℃ and stirred 3 hours, remove by filter insoluble solids, filtrate steaming removal solvent obtains two benzene methanesulfonic acids.
1H?NMR(400MHz，CDCl
3)δ5.24(s，1H)，7.16(m，6H)，7.44(m，4H)
The preparation of embodiment 5:3-TMS propanesulfonic acid
3-TMS propanesulfonic acid potassium 234mg, Silver Nitrate 170mg is dissolved in respectively in the 30ml acetonitrile; Mix back adularescent solid and separate out, stirring at room 2 hours is filtered and is obtained white solid; In white solid, add lmol/L Hydrogen bromide 10ml, be heated to 40 ℃ and stirred 4 hours, be cooled to room temperature; Remove by filter insoluble solids, filtrate steaming removal solvent obtains 3-TMS propanesulfonic acid.
1H?NMR(400MHz，D
2O)δ0.009(s，9H)，0.62(t，J＝8.4Hz，2H)，1.73-1.81(m，2H)，2.91(t，J＝8.0Hz，2H)
Embodiment 6:1, the preparation of the hot disulfonic acid of 8-
1, the hot sodium disulfonate 272mg of 8-, tachyol 254mg; Room temperature is mixed with white insoluble solid and separates out in 20ml water, continue to stir 2 hours, filters and obtains white solid; In white solid, add 2mol/L hydrochloric acid soln 5ml, be heated to 60 ℃ and stirred 3 hours, be cooled to 0 ℃; Remove by filter insoluble solids, filtrate steaming removal solvent obtains 1, the hot disulfonic acid of 8-.
1H?NMR(400MHz，D
2O)δ1.32-1.46(m，8H)，1.68-1.76(m，4H)，2.89(t，J＝8.0Hz，4H)
The preparation of embodiment 7:4-methylthio group fourth sulfonic acid
4-methylthio group fourth sodium sulfonate 206mg, Silver Nitrate 170mg is dissolved in the 20ml acetonitrile respectively; There is insoluble white solid to separate out after the mixing; Stirring at room 2 hours is filtered the back and in white solid, is added 1mol/L hydrochloric acid 3ml, is heated to 60 ℃ and stirs 2 hours; Remove by filter insoluble solids, filtrate steaming removal solvent obtains 4-methylthio group fourth sulfonic acid.
1H?NMR(400MHz，CDCl
3)δ1.68(2H，m)，1.79(2H，m)，2.09(3H，s)，2.54(2H，m)，2.88(2H，m)
Embodiment 8: the preparation of O-phthalic sulfonic acid
O-phthalic sodium sulfonate 310mg is dissolved in 20ml ethanol, and Silver Nitrate 340mg is dissolved in the 35ml acetonitrile, and both are mixed stirring; There is insoluble white solid to separate out, is heated to 70 ℃ and stirred 30 minutes, to wherein adding entry 20ml; Filtration obtains white solid, in this solid, adds 2mol/L hydrochloric acid 10ml, is heated to 100 ℃ and stirs 2h; Remove by filter insoluble solids, filtrate decompression distillation removes desolvates and residual hydrochloric acid obtains O-phthalic sulfonic acid.
1H?NMR(400MHz，CD
3OD)δ4.31(s，4H)，7.29-7.32(m，4H)
Embodiment 9:1,3, the preparation of 5-triethylbenzene sulfonic acid
1,3,5-triethylbenzene calcium sulphonate 520mg is dissolved in the 30ml acetone, and Silver monoacetate 340mg is dissolved in the 40ml acetone; Both mixing are heated with stirring to 50 ℃ and stirred 2 hours, and the adularescent solid is separated out, and in reaction solution, add 30ml water; Filtration obtains white solid, and the hydrochloric acid 5ml and the 5ml acetone that in white solid, add 1mol/L are heated to 60 ℃ of stirring 2h, remove by filter insoluble solid; Filtrate steaming removal solvent obtains 1,3,5-triethylbenzene sulfonic acid.
1H?NMR(400MHz，CDCl
3)δ1.08(6H，t，J＝7.8Hz)，1.18(3H，t，J＝7.4Hz)，2.54(2H，m)，2.94(4H，m)，6.86(2H，s).
Comparative Examples 1:
456 gram 27.6% sodium sulfite solutions and 142 gram methyl iodide are joined in the autoclave of 1L, be heated to 60 ℃, stirred 2.5 hours.Stop heating, extract reaction solution out, revolve to steam and remove till the solid of moisture to Baise.Add 300ml concentrated hydrochloric acid (～35%), stir, produce a large amount of white precipitates, hold over night leaches salt, gets yellow solution.This solution is revolved steaming eliminate moisture content, underpressure distillation is 167 ℃ in temperature; Pressure is under the condition of 1.33kPa, collects colourless transparent liquid 93.1 grams, productive rate 97.1%; Purity>=99.5%, maximum chloride ion content≤5 μ g/ml, maximum sulfate ion content≤10 μ g/ml.(CN101875623A)
Comparative Examples 2:
The ammonium sulfite solution that the use pump is squeezed into 1.9 tons of concentration in 3000 liters of reaction kettles be 35% (wt%); Open stirring and be warming up to 90 ± 2 ℃; Keep this temperature and in 3 hours, drip 330 kilograms of methyl-sulfates, behind the dropping methyl-sulfate, isothermal reaction is 2 hours under said temperature; Reaction finishes the back intensification distillation methyl alcohol that water outlet and side reaction produced, and reaction solution is slowly joined contain 370 kilograms of Ca (OH) then
2Emulsion (moisture about 1 ton) in, have this moment a large amount of ammonias to generate, stir to distill down and be blown into air and remove ammonia, ammonia reclaims also and SO through the ammonia absorber water
2Prepared in reaction ammonium sulphite aqueous solution recycled, with the centrifuging of still kettle raffinate cooling back, and with 100 kg of water with filter cake washing 2 times; Filtrating and washing lotion merge, to wherein slowly dripping 220 kilograms of vitriol oils and stirring reaction solution centrifuging 0.5 hour; With filter cake washing 2 times, filtrating and washing lotion merge with 60 kg of water, and underpressure distillation goes out most water; The concentration kettle raffinate obtains methylsulphonic acid through underpressure distillation again, and product is a colourless transparent liquid, Cl
-Ion content equals 0ppm, SO
4 2-Ion content is less than 10ppm, and the still kettle raffinate is circulated to together distillation in the next batch acid adjustment liquid, and the average yield of methylsulphonic acid product is 84% (pressing methyl-sulfate calculates).(CN1810780A)
Comparing embodiment and Comparative Examples 1 can know that Comparative Examples 1 makes the sodium ion in the solution separate out with the form of sodium-chlor through in sulfonate solution, adding excessive concentrated hydrochloric acid, and solution obtains methylsulfonic acid through underpressure distillation again.High boiling sulfonic acid uses the method for Comparative Examples 1 to be difficult to purifying, uses the method for embodiment then can realize.
Comparing embodiment and Comparative Examples 2 can be known; Comparative Examples 2 is used and can be formed sedimentary calcium hydroxide processing reaction liquid with sulfate ion; Remove by filter the calcium sulfate that is insoluble in water, calcium sulphonate soluble in water in the filtrating is passed through vitriolization again, obtains methylsulphonic acid through underpressure distillation at last.High boiling sulfonic acid uses this method to be difficult to obtain sulfonic acid through underpressure distillation, uses the method for embodiment then can realize.
Claims (8)
1. the preparation method of an organic sulfonic acid compounds is characterized in that: contain and have the following steps:
(1) uses organic sulfonate and the silver salt shown in the formula I to be dissolved in the solvent, obtain organic sulfonic acid silver after the reaction;
(2) in step (1), add the haloid acid reaction in the organic sulfonic acid silver of gained, remove insolubles, obtain the organic sulfonic acid compounds shown in the formula II;
G-SO
3M G-SO
3H
(formula I) (formula II)
Wherein: group G is a kind of in alkyl, aryl, heterocyclic radical, substituted alkyl, substituted aryl or the substituted heterocyclic radical, and substituting group is one or more in the substituted radical of carbon containing, fluorine, chlorine, bromine, iodine, oxygen, sulphur, nitrogen, phosphorus or silicon; M is: basic metal, earth alkali metal or subgroup metal; Said silver salt is a soluble silver salt.
2. according to the preparation method of the described organic sulfonic acid compounds of claim 1, it is characterized in that: described M is selected from a kind of in lithium, sodium, potassium, caesium, magnesium, calcium, strontium, barium, iron, copper or the zinc.
3. according to the preparation method of the described organic sulfonic acid compounds of claim 1, it is characterized in that: described solvent is one or more in water or the polar organic solvent.
4. according to the preparation method of the described organic sulfonic acid compounds of claim 3; It is characterized in that: described polar organic solvent is selected from methyl alcohol, ethanol, propyl alcohol, Virahol, butanols, acetone, methyl ethyl ketone, ETHYLE ACETATE, ether, methyl ethyl ether, acetonitrile, THF, 1; 4-dioxane, N; In dinethylformamide, DMAC N,N, DMSO 99.8MIN., formic acid, acetate, Nitromethane 99Min., terepthaloyl moietie, Ucar 35, USP Kosher or the glycol ether one or more.
5. according to the preparation method of the described organic sulfonic acid compounds of claim 1, it is characterized in that: described soluble silver salt is selected from Silver Nitrate, tachyol, silver perchlorate, Silver monoacetate or two ammoniums and closes in the silver one or more.
6. according to the preparation method of the described organic sulfonic acid compounds of claim 1, it is characterized in that: the temperature of reaction of step (1) is 0-200 ℃.
7. according to the preparation method of the described organic sulfonic acid compounds of claim 1, it is characterized in that: the temperature of reaction of step (2) is 0-200 ℃.
8. according to the preparation method of the described organic sulfonic acid compounds of claim 1, it is characterized in that: described haloid acid is one or more in hydrochloric acid, Hydrogen bromide or the hydroiodic acid HI.
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| CN104086463A (en) * | 2014-07-14 | 2014-10-08 | 河南豫辰精细化工有限公司 | Preparation method of 1,4-butyldisulfonic acid fine product and solution thereof |
| CN109535039A (en) * | 2018-12-18 | 2019-03-29 | 湖北优世达科技股份有限公司 | The method of one-step synthesis method perfluorohexylethyl sulfonic acid |
| CN114075125A (en) * | 2020-08-13 | 2022-02-22 | 上海漫关越水处理有限公司 | Long-chain alkyl fluorine-containing sulfonate ionic membrane compound for blocking water permeation of lithium-air battery |
| CN113666850A (en) * | 2021-06-18 | 2021-11-19 | 厦门威亮光学涂层技术有限公司 | Preparation method and application of organic sulfonic acid |
| WO2023123170A1 (en) * | 2021-12-30 | 2023-07-06 | 浙江海正药业股份有限公司 | Preparation method for 1,4-butanedisulfonic acid |
| CN115433109A (en) * | 2022-07-27 | 2022-12-06 | 厦门威亮光学涂层技术有限公司 | Preparation method of organic sulfonic acid amine salt |
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| CN118063356A (en) * | 2024-04-15 | 2024-05-24 | 南京师范大学 | Preparation method of high-purity sodium metasilicate/heptane sulfonate |
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Application publication date: 20121024 |