CN101195593A - Industrial production method of alkylbenzene sulfonyl chloride - Google Patents
Industrial production method of alkylbenzene sulfonyl chloride Download PDFInfo
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- CN101195593A CN101195593A CNA200710044413XA CN200710044413A CN101195593A CN 101195593 A CN101195593 A CN 101195593A CN A200710044413X A CNA200710044413X A CN A200710044413XA CN 200710044413 A CN200710044413 A CN 200710044413A CN 101195593 A CN101195593 A CN 101195593A
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- Prior art keywords
- sulfonyl chloride
- alkylbenzene
- chlorosulfonic acid
- reaction
- acid
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- 238000000034 method Methods 0.000 title claims abstract description 20
- -1 alkylbenzene sulfonyl chloride Chemical class 0.000 title claims abstract description 9
- 238000009776 industrial production Methods 0.000 title claims description 5
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims abstract description 36
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims abstract description 25
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims abstract description 25
- 238000004519 manufacturing process Methods 0.000 claims abstract description 20
- 239000007788 liquid Substances 0.000 claims abstract description 17
- 239000002904 solvent Substances 0.000 claims abstract description 17
- 238000005660 chlorination reaction Methods 0.000 claims abstract description 8
- 125000002252 acyl group Chemical group 0.000 claims abstract description 7
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000002253 acid Substances 0.000 claims abstract description 6
- 150000001335 aliphatic alkanes Chemical class 0.000 claims abstract description 3
- 150000004996 alkyl benzenes Chemical class 0.000 claims description 22
- 238000006277 sulfonation reaction Methods 0.000 claims description 12
- 229940057995 liquid paraffin Drugs 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 230000003301 hydrolyzing effect Effects 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 239000003208 petroleum Substances 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 239000000047 product Substances 0.000 abstract description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract description 8
- 239000000126 substance Substances 0.000 abstract description 4
- 238000010924 continuous production Methods 0.000 abstract description 3
- 239000007795 chemical reaction product Substances 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 abstract 4
- 150000005826 halohydrocarbons Chemical class 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000002699 waste material Substances 0.000 description 7
- 238000001816 cooling Methods 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- SNHOURMNEXCAJV-UHFFFAOYSA-N sulfuryl dichloride;toluene Chemical compound ClS(Cl)(=O)=O.CC1=CC=CC=C1 SNHOURMNEXCAJV-UHFFFAOYSA-N 0.000 description 1
- 239000002912 waste gas Substances 0.000 description 1
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Abstract
The invention relates to an industrialized production process of alkyl benzenesulfonyl chloridebenzene sulfonyl chloride, which uses tubular reactor to continuously or kettle-type intermittently sulfonate alkyl benzene and liquid sulfur trioxide in the solvent as liquid sulfur dioxide, liquid wax, ligarine, and halohydrocarbon of C1-C4, 90-120# solvent oil and alkane of C4-C8 or the like, directly treats the reaction product and chlorosulfonic acid with acyl chlorination via a tubular reactor continuously or a kettle intermittently, to generate alkyl benzenesulfonyl chloridebenzene sulfonyl chloride, washes alkyl benzenesulfonyl chloridebenzene sulfonyl chloride, removes acid, and desolventizes to generate product alkyl benzenesulfonyl chloridebenzene sulfonyl chloride. The invention avoids generating hydrochloride gas, to support tube continuous production, reduce dangerous chemical in production system, reduce equipment investment, and improve economic benefit, which replaces chlorosulfonic acid with sulfur trioxide to process sulphonation to realize clean production and reduce material cost.
Description
Technical Field
The invention relates to an industrial production method of alkyl benzene sulfonyl chloride, in particular to a novel process for continuously or intermittently producing alkyl benzene sulfonyl chloride by utilizing liquid sulfur trioxide and chlorosulfonic acid in a solvent.
Background
Alkyl benzene sulfonyl chloride generated by the chlorosulfonation reaction of alkyl benzene (benzene, toluene, ethylbenzene and the like) is an important fine chemical product, is an important intermediate in the industries of medicines, dyes, pigments and plastic auxiliaries and has very wide application.
There are several methods for industrially producing alkylbenzenesulfonyl chloride, but most of them are formed by reacting alkylbenzene with excess chlorosulfonic acid and then hydrolyzing excess chlorosulfonic acid, but different auxiliaries such as phosphorus oxychloride, inorganic ammonium salts, alkali metals or alkaline earth metals, etc. are added during sulfonation in consideration of the amount of isomers, and there are some changes in reaction temperature and hydrolysis manner, etc. in the related art, see german patent DE 1172258, DE1112978, US patent US3686300, japanese patent JP 56-46860, chinese patent CN1824649, CN1405151, CN1049213C, CN1436773A, etc.
In the process flow (figure 1) of the traditional process, alkylbenzene directly reacts with excessive chlorosulfonic acid, so that a large amount of waste sulfuric acid and waste hydrochloric acid are generated, the treatment is difficult, and the three wastes are polluted greatly; the separation of the materials and the waste acid is difficult in the later period; meanwhile, the use of a large amount of chlorosulfonic acid causes the synthesis cost to be overhigh and the production lacks competitiveness; in the large-scale production process, the safety of the production apparatus is very poor due to the use of a large amount of chlorosulfonic acid in the batch reaction system.
Disclosure of Invention
The invention aims to provide an industrial production process of alkyl benzene sulfonyl chloride, which aims to reduce the pollution to the environment, improve the safety of a production device and reduce the production cost.
The technical scheme of the invention is as follows:
1) and (3) sulfonation reaction: in the presence of a solvent, under the condition of-20-80 ℃, continuously sulfonating by using a pipeline reactor or intermittently sulfonating in a kettle way;
2) acyl chlorination reaction: and (2) directly reacting the product generated in the sulfonation reaction 1) with chlorosulfonic acid, performing acyl chlorination reaction continuously or intermittently in a kettle manner by using a pipeline reactor at the temperature of-20-80 ℃ to generate alkylbenzene sulfonylchloride, hydrolyzing slightly excessive chlorosulfonic acid, and then separating acid and desolventizing to generate alkylbenzene sulfonyl chloride.
The substituent on the benzene ring of the alkylbenzene is alkyl containing 0-10 carbon atoms.
The solvent in the sulfonation reaction 1) of the preparation method comprises liquid sulfur dioxide, liquid paraffin, petroleum ether and C1～C4Halogenated hydrocarbon, 90-120 # solvent oil or C4～C8An alkane; the weight percentage concentration of the liquid sulfur trioxide is 1-100%, the weight percentage concentration of the alkylbenzene is 1-100%, and the molar ratio of the alkylbenzene to the liquid sulfur trioxide is 1: 0.5-2.5.
The dosage of chlorosulfonic acid in the acyl chlorination reaction 2) is as follows: the molar ratio of the alkylbenzene to the chlorosulfonic acid is 1: 0.5-3.5.
The process flow of the production process of the alkylbenzene sulfonyl chloride is shown in figure 2, and the reaction formula is as follows
Through the pipeline continuous production, the dangerous chemical substances of the production system can be greatly reduced, the intrinsic safety of the system is realized, the investment of the device is reduced, and the economic benefit is improved. By replacing part of chlorosulfonic acid with liquid sulfur trioxide, not only can the production cost be greatly reduced, but also the discharge of waste acid and waste gas can be greatly reduced, and the purpose of emission reduction is achieved.
The solvent participates in the reaction, so that the whole process is liquefied, the possibility is provided for the pipeline continuous process, and the direct separation of waste acid can be directly realized.
Meanwhile, the preparation method can realize the byproduct of the alkylbenzene sulfonic acid, and greatly improve the operation efficiency of the device.
The invention has the beneficial effects that:
the invention uses liquid-phase sulfur trioxide as a sulfonating agent instead, which is the most economic synthesis mode in organic synthesis, does not produce any pollution, only connects sulfur trioxide to a benzene ring, is a green clean synthesis process, and is qualitatively leap compared with the traditional sulfonation by using chlorosulfonic acid. The product alkyl benzene sulfonic acid further reacts with chlorosulfonic acid without generating hydrogen chloride gas, and completely without generating waste hydrochloric acid, and the byproduct sulfuric acid is greatly reduced compared with the traditional process, thereby having obvious clean production characteristics. Meanwhile, the energy consumption is greatly reduced due to the adoption of the pipelining reaction. The sulfur trioxide has relatively small molecular weight and the price is less than half of that of chlorosulfonic acid, so that the sulfur trioxide is used for substituting chlorosulfonic acid for sulfonation, thereby greatly reducing the production cost. In addition, the use of the solvent in the new process greatly reduces the activity of the liquid sulfur trioxide, makes direct sulfonation possible and improves the yield. Meanwhile, the solvent can directly play a part of positioning role along with the change of the proportion of the solvent.
The production process of the invention has no hydrogen chloride gas generated in the whole reaction process, can realize pipeline continuous reaction, has stable production and easy control, and has less amount of dangerous chemicals stored in a system with the same production scale and good intrinsic safety. The method avoids the defects of poor intrinsic safety and high energy consumption caused by the adoption of intermittent reaction, difficulty in production control, more unorganized hydrogen chloride emission, and large amount of dangerous chemicals stored in a system with the same production scale in the traditional process.
Drawings
FIG. 1: a flow chart of the traditional production process of alkyl benzene sulfonyl chloride.
FIG. 2: the invention relates to a production process flow chart of alkyl benzene sulfonyl chloride.
Detailed Description
The present invention is further illustrated by the following examples, which are not intended to limit the scope of the invention.
Example 1
Cooling a benzene (liquid paraffin) solution with the flow rate of 39kg/h and the concentration of 20% by a metering pump, then injecting the cooled benzene (liquid paraffin) solution and a liquid sulfur trioxide (liquid paraffin) solution with the flow rate of 16kg/h and the concentration of 50% after pre-cooling into a 500ml four-neck flask continuous sulfonation pipeline reactor with a stirrer, a thermometer and a charging opening, and controlling the temperature to react at 50-60 ℃. The reacted feed liquid and chlorosulfonic acid with the flow rate of 11.6kg/h enter a continuous chlorination pipeline reactor together, the reaction temperature is controlled to be 60-70 ℃, the reaction product enters a continuous desolventizing system after the reaction is finished, and the product enters a crystallization system after the solvent is removed to separate a benzenesulfonyl chloride product with the purity of 16.4kg/h, wherein the product purity is 97%, and the yield is 90.1%.
Example 2
Adding 920kg of toluene and 500kg of chloroform into a 3000L reaction kettle with a stirrer, a thermometer and a charging hole, starting stirring, dropping 1600kg of liquid sulfur trioxide/chloroform solution (wherein the concentration of sulfur trioxide is 50%) at the temperature of 60-70 ℃, keeping the temperature for 1 hour after dropping, then adding 1160kg of chlorosulfonic acid at the temperature of 60-70 ℃, and keeping the temperature for 1 hour after dropping and heating to 70-80 ℃. Cooling to 20 deg.C, adding small amount of water, washing, layering, and desolventizing solvent layer to obtain 1860kg of methyl benzenesulfonyl chloride product with purity of 95% and yield of 92.8%.
Example 3
Adding 10 g of liquid paraffin into a 500ml four-neck flask with a stirrer, a thermometer and a charging hole, starting stirring, then simultaneously dropwise adding 0.1mol of benzene and 0.05mol of liquid sulfur trioxide (containing 10 g of liquid paraffin), controlling the temperature to be minus 20-0 ℃ for reaction, after dropwise adding, keeping the temperature for 2 hours, then adding 0.35mol of chlorosulfonic acid at minus 20 ℃, after dropwise adding, heating to 60-70 ℃ and keeping the temperature for 2 hours. Cooling to 20 deg.c, washing with small amount of water, layering, and desolventizing in solvent layer to obtain benzenesulfonyl chloride product 16.4 g, purity 97% and yield 90.1%.
Example 4
Adding 0.1mol of toluene (containing 5 g of chloroform) into a 500ml four-neck flask with a stirrer, a thermometer and a charging hole, starting stirring, dropping 0.25mol of liquid sulfur trioxide (containing 100 g of chloroform) at the temperature of 60-80 ℃, keeping the temperature for 1 hour after dropping, then adding 0.05mol of chlorosulfonic acid at the temperature of 60-70 ℃, and keeping the temperature for 1 hour after dropping and heating to-20-0 ℃. Cooling to 20 ℃, adding a small amount of water for washing, layering, and desolventizing a solvent layer to obtain 18.6 g of the methyl benzene sulfonyl chloride product with the purity of 95% and the yield of 92.8%.
Claims (5)
1. An industrial production method of alkyl benzene sulfonyl chloride comprises the following steps:
1) and (3) sulfonation reaction: in the presence of a solvent, under the condition of-20-80 ℃, continuously sulfonating by using a pipeline reactor or intermittently sulfonating in a kettle way;
2) acyl chlorination reaction: and (2) directly reacting the product generated in the sulfonation reaction 1) with chlorosulfonic acid, performing acyl chlorination reaction continuously or intermittently in a kettle manner by using a pipeline reactor at the temperature of-20-80 ℃ to generate alkylbenzene sulfonyl chloride, hydrolyzing slightly excessive chlorosulfonic acid, and then separating acid and desolventizing to generate alkylbenzene sulfonyl chloride.
2. The method of claim 1, wherein the substituent on the benzene ring of the alkylbenzene is an alkyl group having 0 to 10 carbons.
3. The method of claim 1, wherein the solvent used in sulfonation 1) comprises liquid sulfur dioxide, liquid paraffin, petroleum ether, C1～C4Halogenated hydrocarbon, 90-120 # solvent oil or C4～C8An alkane.
4. The method of claim 1, wherein the liquid sulfur trioxide in the sulfonation reaction 1) is at a concentration of 1 to 100 wt%, the alkylbenzene is at a concentration of 1 to 100 wt%, and the molar ratio of the alkylbenzene to the liquid sulfur trioxide is 1: 0.5 to 2.5.
5. The industrial process for preparing alkylbenzene sulfonic acid chloride according to claim 1, wherein the dosage of chlorosulfonic acid in the acyl chlorination reaction 2) is as follows: the molar ratio of the alkylbenzene to the chlorosulfonic acid is 1: 0.5-3.5.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200710044413XA CN101195593B (en) | 2007-07-31 | 2007-07-31 | Industrial production method of alkylbenzene sulfonyl chloride |
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| CN200710044413XA CN101195593B (en) | 2007-07-31 | 2007-07-31 | Industrial production method of alkylbenzene sulfonyl chloride |
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| CN101195593A true CN101195593A (en) | 2008-06-11 |
| CN101195593B CN101195593B (en) | 2010-12-08 |
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102489488A (en) * | 2011-11-14 | 2012-06-13 | 锦州开元石化有限责任公司 | Process for recycling alkylbenzene sulfonate filter residues |
| CN102746199A (en) * | 2012-07-13 | 2012-10-24 | 江苏丰山集团有限公司 | Method for recovering paratoluensulfonyl chloride from waste water generated by producing aryloxy phenoxy propionic acid herbicide |
| CN103304451A (en) * | 2013-05-13 | 2013-09-18 | 台州市前进化工有限公司 | Preparation method of aromatic hydrocarbon sulfonyl chloride derivative |
| CN111377837A (en) * | 2020-03-18 | 2020-07-07 | 湖南吴赣药业有限公司 | Green synthesis method of p-acetamido-benzenesulfonyl chloride |
| CN111718286A (en) * | 2020-07-23 | 2020-09-29 | 邓博天 | Industrial production method of aromatic hydrocarbon sulfonyl chloride with power supply group |
| CN113277965A (en) * | 2021-05-21 | 2021-08-20 | 金华双宏化工有限公司 | Method for continuously synthesizing paratoluensulfonyl chloride by using microchannel reactor |
| CN113582883A (en) * | 2021-08-03 | 2021-11-02 | 金华双宏化工有限公司 | Method for continuously synthesizing p-toluenesulfonyl chloride |
| CN115710204A (en) * | 2022-11-21 | 2023-02-24 | 金华双宏化工有限公司 | Method for continuously synthesizing benzene sulfonyl chloride |
| CN116769493A (en) * | 2023-05-11 | 2023-09-19 | 大庆轩隆化工有限公司 | Petroleum alkylbenzene sulfonate surfactant for oil displacement and preparation method thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN86105852A (en) * | 1986-07-14 | 1988-02-03 | 吉林化工学院 | The production method of heavy alkylbenzene sulfonic acid |
-
2007
- 2007-07-31 CN CN200710044413XA patent/CN101195593B/en active Active
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102489488A (en) * | 2011-11-14 | 2012-06-13 | 锦州开元石化有限责任公司 | Process for recycling alkylbenzene sulfonate filter residues |
| CN102746199A (en) * | 2012-07-13 | 2012-10-24 | 江苏丰山集团有限公司 | Method for recovering paratoluensulfonyl chloride from waste water generated by producing aryloxy phenoxy propionic acid herbicide |
| CN103304451A (en) * | 2013-05-13 | 2013-09-18 | 台州市前进化工有限公司 | Preparation method of aromatic hydrocarbon sulfonyl chloride derivative |
| CN111377837A (en) * | 2020-03-18 | 2020-07-07 | 湖南吴赣药业有限公司 | Green synthesis method of p-acetamido-benzenesulfonyl chloride |
| CN111718286A (en) * | 2020-07-23 | 2020-09-29 | 邓博天 | Industrial production method of aromatic hydrocarbon sulfonyl chloride with power supply group |
| CN113277965A (en) * | 2021-05-21 | 2021-08-20 | 金华双宏化工有限公司 | Method for continuously synthesizing paratoluensulfonyl chloride by using microchannel reactor |
| CN113582883A (en) * | 2021-08-03 | 2021-11-02 | 金华双宏化工有限公司 | Method for continuously synthesizing p-toluenesulfonyl chloride |
| CN113582883B (en) * | 2021-08-03 | 2022-11-04 | 金华双宏化工有限公司 | Method for continuously synthesizing p-toluenesulfonyl chloride |
| CN115710204A (en) * | 2022-11-21 | 2023-02-24 | 金华双宏化工有限公司 | Method for continuously synthesizing benzene sulfonyl chloride |
| CN115710204B (en) * | 2022-11-21 | 2024-01-09 | 金华双宏化工有限公司 | Method for continuously synthesizing benzenesulfonyl chloride |
| CN116769493A (en) * | 2023-05-11 | 2023-09-19 | 大庆轩隆化工有限公司 | Petroleum alkylbenzene sulfonate surfactant for oil displacement and preparation method thereof |
| CN116769493B (en) * | 2023-05-11 | 2024-06-21 | 大庆轩隆化工有限公司 | Petroleum alkylbenzene sulfonate surfactant for oil displacement and preparation method thereof |
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Effective date of registration: 20241031 Address after: No. 2288, Zhapu Binhai Avenue, Jiaxing City, Zhejiang Province, 314201 Patentee after: ZHEJIANG JIAHUA ENERGY CHEMICAL INDUSTRY CO.,LTD. Country or region after: China Address before: 314201 room 318, building 1, south side of Zhongshan Road and west side of Washan Road, Jiaxing Port Area, Jiaxing City, Zhejiang Province Patentee before: Zhejiang Jiafu New Material Technology Co.,Ltd. Country or region before: China |