CN110950783A - Solid phase synthesis method of N-butyl benzene sulfonamide - Google Patents
Solid phase synthesis method of N-butyl benzene sulfonamide Download PDFInfo
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- CN110950783A CN110950783A CN201911160520.8A CN201911160520A CN110950783A CN 110950783 A CN110950783 A CN 110950783A CN 201911160520 A CN201911160520 A CN 201911160520A CN 110950783 A CN110950783 A CN 110950783A
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- solid
- carbonate
- hydroxide
- butylbenzenesulfonamide
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- C07C303/38—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reaction of ammonia or amines with sulfonic acids, or with esters, anhydrides, or halides thereof
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/42—Separation; Purification; Stabilisation; Use of additives
- C07C303/44—Separation; Purification
Abstract
The invention discloses a solid-phase synthesis method of N-butylbenzene sulfonamide, which comprises the following steps: feeding and reacting: performing solvent-free solid phase reaction on benzene sulfonyl chloride, n-butylamine raw materials and an inorganic alkaline compound; (2) and (3) suction filtration: separating and washing the reacted solid with an organic solvent, and combining the organic phases; (3) and (3) distillation and purification: and (3) carrying out reduced pressure distillation and purification on the combined organic phase under vacuum, and collecting 150-160 ℃/0.5mmHg fractions to obtain the N-butylbenzenesulfonamide. The method adopts benzene sulfonyl chloride, N-butylamine as raw materials and an inorganic alkaline compound to carry out solvent-free solid phase reaction to synthesize the N-butylbenzene sulfonamide, has the advantages of simple process, mild reaction conditions, high synthesis rate, safety and environmental protection, and the obtained N-butylbenzene sulfonamide has the advantages of high yield, high purity, good quality and wide market prospect.
Description
Technical Field
The invention relates to the technical field of chemical production, in particular to a solid-phase synthesis method of N-butylbenzene sulfonamide.
Background
N-butyl benzene sulfonamide (Cas: 3622-84-2) with molecular formula of C10H15NO2S, molecular weight 213.3, colorless transparent liquid at room temperature, boiling pointIt was 314 ℃.
N-butylbenzenesulfonamide is an important chemical intermediate, which is an excellent liquid plasticizer, mainly used in the fields of polyamide, cellulose resin and nylon plastics, on the one hand, and also used in the fields of latex adhesives, hot melt adhesives, printing inks and surface coatings, on the other hand.
The N-butylbenzene sulfonamide is generally synthesized by taking benzene sulfonyl chloride and N-butylamine as raw materials and tertiary amine such as triethylamine as an acid-binding agent as reported in literature. In the synthesis methods, a large amount of organic solvent and tertiary amine are used, the production cost is high, the treatment is complex, and the product quality is not high due to the residue of the tertiary amine, so the synthesis methods cannot be suitable for industrial production.
Currently, the industry also adopts benzene sulfonyl chloride and 3 equivalent N-butylamine as raw materials, a high-concentration sodium hydroxide solution as an acid-binding agent, a silicon-aluminum composite porous catalyst and ultrasonic waves as auxiliary means to produce the N-butylbenzene sulfonamide. The production method can avoid the residue of tertiary amine in the product; however, the high-concentration sodium hydroxide solution has strong alkalinity, so that the benzenesulfonyl chloride is hydrolyzed, and the reaction yield is low; in addition, the strong alkalinity of the sodium hydroxide solution inevitably generates a byproduct N-butyl diphenyl sulfimide (the structural formula is shown as the following), and the purity and the yield of the N-butyl benzene sulfonamide are reduced.
In view of that N-butyl benzene sulfonamide is an extremely important chemical raw material and has great market demand, it is very meaningful to find a novel synthesis process to improve reaction conditions, inhibit the generation of impurities, obtain a product with high yield and high purity, and realize the industrial production thereof, and has good economic and social benefits.
Disclosure of Invention
The invention mainly solves the technical problem of providing an N-butylbenzene sulfonamide solid phase synthesis method, which can solve the problems existing in the prior art for preparing N-butylbenzene sulfonamide.
In order to solve the technical problems, the invention adopts a technical scheme that: provides a solid-phase synthesis method of N-butylbenzenesulfonamide, which adopts a solvent-free solid-phase reaction method and comprises the following steps:
(1) feeding and reacting: adding n-butylamine and a solid inorganic alkaline compound into a container provided with a mechanical stirrer, a temperature measuring conduit, a spherical condenser pipe and a constant pressure funnel, heating to a reaction temperature, dropwise adding benzene sulfonyl chloride, preserving the temperature until the reaction is complete, and cooling;
(2) and (3) suction filtration: separating and washing the solid reacted in the step (1) by using an organic solvent, combining organic phases, and concentrating and recovering the organic solvent;
(3) and (3) distillation and purification: and (3) carrying out reduced pressure distillation purification on the organic phase combined in the step (2) under vacuum, and collecting 150-160 ℃/0.5mmHg fractions to obtain the N-butylbenzenesulfonamide.
In a preferred embodiment of the present invention, in the step (1), the n-butylamine, the solid inorganic basic compound and the benzenesulfonyl chloride are fed in a molar ratio of: 1: 1-1.2: 0.5-5.
In a preferred embodiment of the present invention, in the step (1), the dripping time of the benzenesulfonyl chloride is 30-60 min.
In a preferred embodiment of the present invention, in the step (1), the reaction conditions are as follows: the reaction temperature is 0-100 ℃; the reaction time is 45 min-4 h.
In a preferred embodiment of the present invention, the reaction temperature is 20 to 65 ℃.
In a preferred embodiment of the present invention, in the step (1), the conditions for completing the reaction are as follows: and detecting the reaction by using a gas phase until no raw material is left.
In a preferred embodiment of the present invention, in the step (1), the solid inorganic basic compound is one or more of sodium carbonate, potassium carbonate, strontium carbonate, lithium carbonate, calcium carbonate, barium carbonate, ammonium carbonate, copper carbonate, magnesium carbonate, zinc carbonate, manganese carbonate, sodium bicarbonate, potassium bicarbonate, copper hydroxycarbonate, calcium oxide, magnesium oxide, zinc oxide, iron oxide, copper oxide, aluminum oxide, manganese oxide, sodium hydroxide, potassium hydroxide, magnesium hydroxide, calcium hydroxide, iron hydroxide, copper hydroxide, zinc hydroxide, barium hydroxide, lithium hydroxide, aluminum hydroxide or cesium hydroxide.
In a preferred embodiment of the present invention, the solid inorganic basic compound is one or more of sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, calcium oxide, magnesium oxide, or zinc hydroxide.
In a preferred embodiment of the present invention, in the step (2), the organic solvent is chloroform.
In a preferred embodiment of the present invention, in the step (3), the reduced pressure distillation conditions are as follows: the temperature is 140-250 ℃ and the vacuum degree is 0.1-1 mmHg.
The invention has the beneficial effects that: the invention relates to a solid-phase synthesis method of N-butylbenzenesulfonamide, which adopts benzene sulfonyl chloride, N-butylamine as raw materials and inorganic alkaline compounds to carry out solvent-free solid-phase reaction to synthesize the N-butylbenzenesulfonamide.
Detailed Description
The following detailed description of the preferred embodiments of the present invention is provided to enable those skilled in the art to more readily understand the advantages and features of the present invention, and to clearly and unequivocally define the scope of the present invention.
The embodiment of the invention comprises the following steps:
the invention discloses a solid-phase synthesis method of N-butylbenzene sulfonamide, which comprises the following steps:
(1) feeding and reacting: in a container provided with a mechanical stirrer, a temperature measuring conduit, a spherical condenser tube and a constant pressure funnel, the feeding molar ratio of n-butylamine, a solid inorganic alkaline compound and benzenesulfonyl chloride is as follows: 1: 1-1.2: 0.5-5, adding n-butylamine and a solid inorganic alkaline compound, heating to a reaction temperature of 0-100 ℃, preferably 20-65 ℃, dropwise adding benzene sulfonyl chloride within 30-60 min, reacting for 45-4 min under heat preservation until no raw material is left (namely no benzene sulfonyl chloride is left) in gas phase detection, and cooling to stop reaction;
wherein the solid inorganic basic compound is one or more of sodium carbonate, potassium carbonate, strontium carbonate, lithium carbonate, calcium carbonate, barium carbonate, ammonium carbonate, copper carbonate, magnesium carbonate, zinc carbonate, manganese carbonate, sodium bicarbonate, potassium bicarbonate, basic copper carbonate, calcium oxide, magnesium oxide, zinc oxide, iron oxide, copper oxide, aluminum oxide, manganese oxide, sodium hydroxide, potassium hydroxide, magnesium hydroxide, calcium hydroxide, iron hydroxide, copper hydroxide, zinc hydroxide, barium hydroxide, lithium hydroxide, aluminum hydroxide or cesium hydroxide;
(2) and (3) suction filtration: separating and washing the solid coating reacted in the step (1) by using organic solvent chloroform, combining the organic phases, concentrating and recovering the chloroform for the next use;
(3) and (3) distillation and purification: and (3) carrying out reduced pressure distillation and purification on the organic phase combined in the step (2) under the vacuum conditions of the temperature of 140-250 ℃ and the vacuum degree of 0.1-1 mmHg, preferably the vacuum conditions of the temperature of 150-160 ℃ and the vacuum degree of 0.2-0.6 mmHg, and collecting 150-160 ℃/0.5mmHg fractions to obtain the N-butylbenzenesulfonamide.
Example 1
In a four-neck flask provided with a mechanical stirrer, a temperature measuring conduit, a spherical condenser tube and a constant pressure funnel, 73 g of butylamine and 60 g of sodium carbonate are added firstly; then heating and controlling the temperature of the reaction system to be 50 ℃, and dropwise adding 180 g of benzene sulfonyl chloride within 30 minutes; after the dropwise addition, the temperature is kept at 50 ℃ for reaction for 45 minutes, the gas phase detection reaction is complete, and the reaction is stopped after cooling.
The solid in the reaction mixture was separated and the solid was washed with 100 ml chloroform, the organic phases were combined and the chloroform was recovered by concentration and used directly for the next synthesis.
And (3) carrying out reduced pressure distillation and purification on the combined organic phase, and collecting 150-160 ℃/0.5mmHg fractions to obtain 210 g of the target product N-butylbenzenesulfonamide with the yield of 98.6%.
Example 2
Firstly adding 73 g of butylamine and 50 g of powdery sodium hydroxide solid into a four-neck flask provided with a mechanical stirrer, a temperature measuring conduit, a spherical condenser tube and a constant pressure funnel; then controlling the temperature of the reaction system to be lower than 15 ℃, and dropwise adding 200 g of benzene sulfonyl chloride within 45 minutes; after the dropwise addition, continuously stirring and reacting for 1 hour at 15 ℃, detecting the reaction in a gas phase completely, and cooling to stop the reaction;
the solid in the reaction mixture was separated and the solid was washed with 100 ml chloroform, the organic phases were combined and the chloroform was recovered by concentration and used directly for the next synthesis.
And (3) carrying out reduced pressure distillation and purification on the combined organic phase, and collecting 150-160 ℃/0.5mmHg fractions to obtain 160 g of the target product N-butylbenzenesulfonamide with the yield of 75%.
Example 3
In a four-neck flask equipped with a mechanical stirrer, a temperature measuring conduit, a spherical condenser tube and a constant pressure funnel, 73 g of n-butylamine, 30 g of powdery calcium oxide solid and 40 g of powdery calcium hydroxide solid are added; then heating and controlling the temperature of the reaction system to be 80 ℃, and dropwise adding 180 g of benzene sulfonyl chloride within 45 minutes under the condition of vigorous stirring; after the dropwise addition, the reaction is continued to be stirred at 80 ℃ for 1 hour, the reaction is detected to be complete in gas phase, and the reaction is stopped after cooling.
The solid in the reaction mixture was separated and the solid was washed with 100 ml chloroform, the organic phases were combined and the chloroform was recovered by concentration and used directly for the next synthesis.
And (3) carrying out reduced pressure distillation and purification on the combined organic phase, and collecting 150-160 ℃/0.5mmHg fractions to obtain 198 g of a target product N-butylbenzenesulfonamide with the yield of 93%.
Example 4
Firstly, 73 g of n-butylamine and 80 g of powdery magnesium oxide solid are added into a four-neck flask provided with a mechanical stirrer, a temperature measuring conduit, a spherical condenser tube and a constant pressure funnel; then heating and controlling the temperature of the reaction system to be 90 ℃, and dropwise adding 180 g of benzene sulfonyl chloride within 1 hour under vigorous stirring; after the dropwise addition, the reaction is continued to be stirred at 90 ℃ for 4 hours, the reaction is detected to be complete in gas phase, and the reaction is stopped after cooling.
The solid in the reaction mixture was separated and the solid was washed with 100 ml chloroform, the organic phases were combined and the chloroform was recovered by concentration and used directly for the next synthesis.
And (3) carrying out reduced pressure distillation and purification on the combined organic phase, and collecting 150-160 ℃/0.5mmHg fractions to obtain 209 g of the target product N-butylbenzenesulfonamide with the yield of 98%.
Example 5
Firstly, 73 g of n-butylamine and 80 g of powdery aluminum hydroxide solid are added into a four-neck flask provided with a mechanical stirrer, a temperature measuring conduit, a spherical condenser tube and a constant pressure funnel; then heating to 80 ℃ and carrying out micro-reflux on the system, stirring vigorously at the speed of 2000r/min, and dropwise adding 200 g of benzene sulfonyl chloride within 1 hour; and after the dropwise addition is finished, stirring and reacting for 4 hours under a micro-reflux state, detecting the reaction in a gas phase, and cooling to stop the reaction.
The solid in the reaction mixture was separated and the solid was washed with 100 ml chloroform, the organic phases were combined and the chloroform was recovered by concentration and used directly for the next synthesis.
And carrying out reduced pressure distillation and purification on the combined organic phase, and collecting 150-160 ℃/0.5mmHg fractions to obtain 188 g of the target product N-butylbenzenesulfonamide with the yield of 88%.
The N-butylbenzenesulfonamide obtained in the above examples is subjected to performance tests, and the results are as follows:
according to the experimental data, the raw materials of benzene sulfonyl chloride and N-butylamine are used for synthesizing the N-butylbenzene sulfonamide through solvent-free solid-phase reaction under the action of a solid inorganic alkaline compound serving as an acid-binding agent, so that the smooth proceeding of the reaction is ensured, the synthesis effect is good, the product N-butylbenzene sulfonamide is high in yield, high in purity and good in comprehensive quality, and the market demand for high-quality products is met.
The solid-phase synthesis method of the N-butylbenzene sulfonamide has the following advantages:
1. the synthesis process flow is simple, the synthesis speed is high, and the utilization rate of raw materials is high;
2. the reaction condition of the solid-phase reaction system is mild, safe, reliable, green and environment-friendly;
3. the obtained N-butyl benzene sulfonamide has high yield, high purity and good quality, and meets the market demand.
The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention, and various modifications and changes may be made by those skilled in the art. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (10)
1. A solid-phase synthesis method of N-butylbenzenesulfonamide is characterized by adopting a solvent-free solid-phase reaction method and comprising the following steps:
(1) feeding and reacting: adding n-butylamine and a solid inorganic alkaline compound into a container provided with a mechanical stirrer, a temperature measuring conduit, a spherical condenser pipe and a constant pressure funnel, heating to a reaction temperature, dropwise adding benzene sulfonyl chloride, preserving the temperature until the reaction is complete, and cooling;
(2) and (3) suction filtration: separating and washing the solid reacted in the step (1) by using an organic solvent, combining organic phases, and concentrating and recovering the organic solvent;
(3) and (3) distillation and purification: and (3) carrying out reduced pressure distillation purification on the organic phase combined in the step (2) under vacuum, and collecting 150-160 ℃/0.5mmHg fractions to obtain the N-butylbenzenesulfonamide.
2. The solid-phase synthesis method of N-butylbenzenesulfonamide according to claim 1, wherein in the step (1), the feeding molar ratio of N-butylamine, the solid inorganic basic compound and benzenesulfonyl chloride is 1: 1-1.2: 0.5-5.
3. The solid-phase synthesis method of N-butylbenzenesulfonamide according to claim 1, wherein in the step (1), the dripping time of the benzenesulfonyl chloride is 30-60 min.
4. The solid-phase synthesis method of N-butylbenzenesulfonamide according to claim 1, wherein in the step (1), the reaction conditions are as follows: the reaction temperature is 0-100 ℃; the reaction time is 45 min-4 h.
5. The solid-phase synthesis method of N-butylbenzenesulfonamide according to claim 4, wherein the reaction temperature is 20-65 ℃.
6. The solid-phase synthesis method of N-butylbenzenesulfonamide according to claim 1, wherein in the step (1), the reaction completion conditions are as follows: and detecting the reaction by using a gas phase until no raw material is left.
7. The solid-phase synthesis method of N-butylbenzenesulfonamide according to claim 1, wherein in the step (1), the solid inorganic basic compound is one or more of sodium carbonate, potassium carbonate, strontium carbonate, lithium carbonate, calcium carbonate, barium carbonate, ammonium carbonate, copper carbonate, magnesium carbonate, zinc carbonate, manganese carbonate, sodium bicarbonate, potassium bicarbonate, basic copper carbonate, calcium oxide, magnesium oxide, zinc oxide, iron oxide, copper oxide, aluminum oxide, manganese oxide, sodium hydroxide, potassium hydroxide, magnesium hydroxide, calcium hydroxide, iron hydroxide, copper hydroxide, zinc hydroxide, barium hydroxide, lithium hydroxide, aluminum hydroxide or cesium hydroxide.
8. The solid-phase synthesis method of N-butylbenzenesulfonamide according to claim 7, wherein the solid inorganic basic compound is one or more of sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, calcium oxide, magnesium oxide or zinc hydroxide.
9. The solid-phase synthesis method of N-butylbenzenesulfonamide according to claim 1, wherein in the step (2), the organic solvent is chloroform.
10. The solid-phase synthesis method of N-butylbenzenesulfonamide according to claim 1, wherein in the step (3), the reduced pressure distillation condition is: the temperature is 140-250 ℃ and the vacuum degree is 0.1-1 mmHg.
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| CN1762984A (en) * | 2005-09-30 | 2006-04-26 | 浙江大学 | Purification method for amide and sulfonylamine compound synthesized from liquid phase |
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| CN109020924A (en) * | 2018-10-24 | 2018-12-18 | 湖南农业大学 | Method for synthesizing benzene sulfonamide compound from benzene sulfonyl chloride compound and secondary amine through metal-free catalysis |
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2019
- 2019-11-23 CN CN201911160520.8A patent/CN110950783A/en active Pending
Patent Citations (5)
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| US4737522A (en) * | 1985-09-03 | 1988-04-12 | Bayer Aktiengesellschaft | N-sulphenylated benzenesulphonic acid amide fungicides |
| CN1038084A (en) * | 1989-04-29 | 1989-12-20 | 张标成 | The manufacture method of foamed concrete and goods thereof |
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| CN109020924A (en) * | 2018-10-24 | 2018-12-18 | 湖南农业大学 | Method for synthesizing benzene sulfonamide compound from benzene sulfonyl chloride compound and secondary amine through metal-free catalysis |
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