CN107176917A - A kind of method for preparing dimethylamino sulfonic acid chloride - Google Patents
A kind of method for preparing dimethylamino sulfonic acid chloride Download PDFInfo
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- CN107176917A CN107176917A CN201710331141.5A CN201710331141A CN107176917A CN 107176917 A CN107176917 A CN 107176917A CN 201710331141 A CN201710331141 A CN 201710331141A CN 107176917 A CN107176917 A CN 107176917A
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- sulfonic acid
- acid chloride
- chloride
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
Abstract
The invention discloses a kind of method for preparing dimethylamino sulfonic acid chloride, it is related to technical field of organic synthesis, in dry conditions, dimethylamine gas is passed through in sulfonic acid chloride liquid, rear back flow reaction is led to clarification, reaction cools after terminating, and obtains front-end volatiles through air-distillation, then obtains product dimethylaminosulfonyl chloride through water pump vacuum distillation.The average purity of product dimethylaminosulfonyl chloride of the present invention reaches more than 97%, and highest molar yield ensures the yield and purity of product close to 80% while the reaction time is shortened, so that the synthetic method is suitable to large-scale production.
Description
Technical field：
The present invention relates to technical field of organic synthesis, and in particular to a kind of method for preparing dimethylamino sulfonic acid chloride.
Background technology：
Dimethylamino sulfonic acid chloride is the important source material for preparing cyazofamid, the Field information pair of cyazofamid (120116-88-3)
Late blight and downy mildew have high prevention effect, and dosage is lower than other bactericide 2~38 times, and the medication phase is flexible, hold
The effect phase is long.At this stage, the method for dimethylamino sulfonic acid chloride is prepared using sulfonic acid chloride, dimethylamine hydrochloride as material, and mixing backflow is produced
A large amount of hydrogen chloride gas, there is certain corrosion to production equipment, do not meet green chemical concept, and low yield, and production cost is expensive,
It is unsuitable for large-scale production.
The content of the invention：
The technical problems to be solved by the invention are to provide a kind of higher, with low cost yield, stable process conditions, behaviour
Make simply, suitable for the method for preparing dimethylaminosulfonyl chloride of large-scale production.
The technical problems to be solved by the invention are realized using following technical scheme：
A kind of method for preparing dimethylamino sulfonic acid chloride, specific preparation process is：In dry conditions, by dimethylamine gas
It is passed through in sulfonic acid chloride liquid, has led to rear back flow reaction to clarification, reaction cools after terminating, and obtains front-end volatiles through air-distillation, then
Product dimethylaminosulfonyl chloride is obtained through water pump vacuum distillation.
The temperature that is passed through of the dimethylamine gas is 10-20 DEG C.
The air-distillation temperature of the front-end volatiles is 80-90 DEG C.
The beneficial effects of the invention are as follows：
(1) preparation method is not related to high-temperature high-voltage reaction, and process safety is stable, suitable for large-scale production；
(2) characteristic being in a liquid state using sulfonic acid chloride, substitutes dimethylamine hydrochloride, while without adding reaction with dimethylamine gas
Solvent, significantly improves the conversion ratio of dimethylamine, and avoids the generation of a large amount of hydrogen chloride gas, and the synthetic method meets green
The theory of colour chemistry, reduces the harm of environmental pollution, and has saved production cost；
(3) average purity of product dimethylaminosulfonyl chloride reaches more than 97%, and highest molar yield is close to 80%, in contracting
Ensure the yield and purity of product while short reaction time, so that the synthetic method is suitable to large-scale production.
Embodiment：
In order that the technical means, the inventive features, the objects and the advantages of the present invention are easy to understand, tie below
Specific embodiment is closed, the present invention is expanded on further.
Embodiment 1
Sulfonic acid chloride is put into 2L three-necked flasks, front and rear setting buffer unit, rear portion fluid-tight, water-bath cools to 10-20 DEG C,
Dimethylamine is passed through to system, system releases heat, maintains the temperature at 40-50 DEG C.Below 60 DEG C of maximum temperature.Electronic balance claims
Weight, stops being passed through stopping reaction after (duration of ventilation 4h) continuation stirring, 10min and (is increased weight in reaction bulb of actually weighing during 440g
420g), oil bath slowly heats up, 75 DEG C backflow stay overnight (salt slowly dissolves clarification in system temperature-rise period, there is a large amount of sour gas,
Connecing device for recovering tail gas) system still clarifies, and weigh 1000g, 80 DEG C of -90 DEG C of distillations of normal pressure, obtains about 200g cuts, water pump subtracts
Pressure distills to obtain product 650g, purity 96%.Separated out in still-process without solid, the last residual 140g of kettle, in terms of dimethylamine, mole receipts
Rate 46.33%.
Embodiment 2
Sulfonic acid chloride is put into 2L three-necked flasks, front and rear setting buffer unit, rear portion fluid-tight, cryosel cools to 0-10 DEG C,
Dimethylamine is passed through to system, system releases heat, maintains the temperature at 40-50 DEG C.Below 50 DEG C of maximum temperature.Electronic balance claims
Weight, stops being passed through stopping reaction after (duration of ventilation 4h) continuation stirring, 10min and (is increased weight in reaction bulb of actually weighing during 440g
420g), oil bath slowly heats up, 75 DEG C backflow stay overnight (salt slowly dissolves clarification in system temperature-rise period, there is a large amount of sour gas,
Connecing device for recovering tail gas) system still clarifies, and weigh 1100g, 80 DEG C of -90 DEG C of distillations of normal pressure, obtains about 150g cuts, water pump subtracts
Pressure distills to obtain product 800g, purity 97.2%.In still-process without solid separate out, the last residual 120g of kettle in terms of dimethylamine, mole
Yield 56.97%.
Embodiment 3
Sulfonic acid chloride is put into 2L three-necked flasks, front and rear setting buffer unit, rear portion fluid-tight, cryosel cools to 0-10 DEG C,
Dimethylamine is passed through to system, system releases heat, maintains the temperature at 10-20 DEG C.Below 30 DEG C of maximum temperature.Electronic balance claims
Weight, stops being passed through stopping reaction after (duration of ventilation 4h) continuation stirring, 10min and (is increased weight in reaction bulb of actually weighing during 440g
420g), oil bath slowly heats up, 75 DEG C backflow stay overnight (salt slowly dissolves clarification in system temperature-rise period, there is a large amount of sour gas,
Connecing device for recovering tail gas) system still clarifies, and weigh 1384g, 80 DEG C of -90 DEG C of distillations of normal pressure, obtains about 71g cuts, water pump subtracts
Pressure distills to obtain product 1116g, purity 98%.Separated out in still-process without solid, the last residual 93g of kettle, in terms of dimethylamine, mole receipts
Rate 79.8%.
The general principle and principal character and advantages of the present invention of the present invention has been shown and described above.The technology of the industry
Personnel are it should be appreciated that the present invention is not limited to the above embodiments, and the simply explanation described in above-described embodiment and specification is originally
The principle of invention, without departing from the spirit and scope of the present invention, various changes and modifications of the present invention are possible, these changes
Change and improvement all fall within the protetion scope of the claimed invention.The claimed scope of the invention by appended claims and its
Equivalent thereof.
Claims (3)
1. a kind of method for preparing dimethylamino sulfonic acid chloride, it is characterised in that specifically preparation process is：In dry conditions, will
Dimethylamine gas is passed through in sulfonic acid chloride liquid, has led to rear back flow reaction to clarification, reaction cools after terminating, and is obtained through air-distillation
Front-end volatiles, then obtain product dimethylaminosulfonyl chloride through water pump vacuum distillation.
2. the method according to claim 1 for preparing dimethylamino sulfonic acid chloride, it is characterised in that：The dimethylamine gas
Temperature is passed through for 10-20 DEG C.
3. the method according to claim 1 for preparing dimethylamino sulfonic acid chloride, it is characterised in that：The normal pressure of the front-end volatiles
Vapo(u)rizing temperature is 80-90 DEG C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710331141.5A CN107176917A (en) | 2017-05-11 | 2017-05-11 | A kind of method for preparing dimethylamino sulfonic acid chloride |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710331141.5A CN107176917A (en) | 2017-05-11 | 2017-05-11 | A kind of method for preparing dimethylamino sulfonic acid chloride |
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| CN107176917A true CN107176917A (en) | 2017-09-19 |
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| CN201710331141.5A Pending CN107176917A (en) | 2017-05-11 | 2017-05-11 | A kind of method for preparing dimethylamino sulfonic acid chloride |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109896984A (en) * | 2019-03-27 | 2019-06-18 | 南通宝凯化工有限公司 | A kind of production technology of dimethylaminosulfonyl chloride |
| CN109912476A (en) * | 2019-03-27 | 2019-06-21 | 南通宝凯化工有限公司 | A kind of production technology of isopropylamino sulfonic acid chloride |
| CN111018762A (en) * | 2019-12-13 | 2020-04-17 | 焦宏典 | Production process of dimethylamino sulfonyl chloride |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1493486A1 (en) * | 1965-07-09 | 1969-11-13 | Basf Ag | Process for the production of organic amido derivatives of sulfuric acid |
| SU542393A1 (en) * | 1975-01-06 | 1981-09-07 | Ордена Трудового Красного Знамени Институт Органического Синтеза Ан Латсср | Method of preparing dimethylaminosulfochloride |
| JPH03127769A (en) * | 1989-10-14 | 1991-05-30 | Ishihara Sangyo Kaisha Ltd | Preparation of dimethylsulfamoyl chloride |
| US5194446A (en) * | 1989-06-12 | 1993-03-16 | A. H. Robins Company, Incorporated | Compounds having one or more aminosulfaonyloxy radicals useful as pharmaceuticals |
| CN1154699A (en) * | 1994-08-09 | 1997-07-16 | 辉瑞研究开发公司 | (Azetidin-1-ylalkyl) lactams as tachykinin antagonists |
-
2017
- 2017-05-11 CN CN201710331141.5A patent/CN107176917A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1493486A1 (en) * | 1965-07-09 | 1969-11-13 | Basf Ag | Process for the production of organic amido derivatives of sulfuric acid |
| SU542393A1 (en) * | 1975-01-06 | 1981-09-07 | Ордена Трудового Красного Знамени Институт Органического Синтеза Ан Латсср | Method of preparing dimethylaminosulfochloride |
| US5194446A (en) * | 1989-06-12 | 1993-03-16 | A. H. Robins Company, Incorporated | Compounds having one or more aminosulfaonyloxy radicals useful as pharmaceuticals |
| JPH03127769A (en) * | 1989-10-14 | 1991-05-30 | Ishihara Sangyo Kaisha Ltd | Preparation of dimethylsulfamoyl chloride |
| CN1154699A (en) * | 1994-08-09 | 1997-07-16 | 辉瑞研究开发公司 | (Azetidin-1-ylalkyl) lactams as tachykinin antagonists |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109896984A (en) * | 2019-03-27 | 2019-06-18 | 南通宝凯化工有限公司 | A kind of production technology of dimethylaminosulfonyl chloride |
| CN109912476A (en) * | 2019-03-27 | 2019-06-21 | 南通宝凯化工有限公司 | A kind of production technology of isopropylamino sulfonic acid chloride |
| CN111018762A (en) * | 2019-12-13 | 2020-04-17 | 焦宏典 | Production process of dimethylamino sulfonyl chloride |
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Application publication date: 20170919 |