CN105669498A - Method for synthetizing 2-naphthalene sulfonyl chloride by phosphorus oxychloride - Google Patents
Method for synthetizing 2-naphthalene sulfonyl chloride by phosphorus oxychloride Download PDFInfo
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- CN105669498A CN105669498A CN201610105276.5A CN201610105276A CN105669498A CN 105669498 A CN105669498 A CN 105669498A CN 201610105276 A CN201610105276 A CN 201610105276A CN 105669498 A CN105669498 A CN 105669498A
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- phosphorus oxychloride
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- sulfonic chloride
- naphthalic sulfonic
- naphthalene sulfonate
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- 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
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
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Abstract
The invention discloses a method for synthetizing 2-naphthalene sulfonyl chloride by phosphorus oxychloride. The method comprises the following steps: 1) successively adding 2-naphthalene sulfonic acid sodium salt and phosphorus oxychloride into a solvent to obtain reaction liquid a; 2) causing the reaction liquid a obtained in the step 1) to react for 4-12h at the temperature of 50-110DEG C to obtain mixed liquor b; 3) after the mixed liquor b obtained in the step 2) is continuously evaporated, successively cleaning, filtering, and carrying out reduced pressure distillation to obtain the 2-naphthalene sulfonyl chloride. The method has the advantages of simplicity in operation, small use amount of solvent, low cost, high product yield, high purity and convenience in solvent recovery, and environment pollution is greatly lightened.
Description
Technical field
The present invention relates to chemosynthesis technical field, specifically refer to the method for a kind of phosphorus oxychloride synthesis 2-naphthalic sulfonic chloride.
Background technology
Acyl chlorides is important organic synthesis intermediate, is important chlorination reagent in the production of chemical products such as agricultural chemicals, medicine, dyestuff, tensio-active agent, auxiliary agent etc.
2-naphthalic sulfonic chloride (2-Naphthalenesulfonylchloride) is important fine chemical product, is the important intermediate in the field of medicine, agricultural chemicals, material, fine chemicals, chemical reagent, and purposes is extensive.
General employing is that solvent made by dimethyl formamide (DMF) or chlorobenzene at present, and sulfur oxychloride makes chloride reagent synthesis 2-naphthalic sulfonic chloride. But, it is more difficult that dimethyl formamide (DMF) makes solvent recuperation, easily causes environmental pollution, is unfavorable for industrial production; Adopting chlorobenzene to make solvent, not only the product yield of 2-naphthalic sulfonic chloride is low, but also needs multiple organic solvent so that laboratory operating procedures is loaded down with trivial details, and product is difficult to purifying.
Summary of the invention
The object of the present invention is exactly the method being provided a kind of phosphorus oxychloride synthesis 2-naphthalic sulfonic chloride, and the method is simple to operate, and solvent load is few, cost is low, and product yield height, purity height, and convenient solvent reclaiming, greatly reduces environmental pollution.
For achieving the above object, the method for a kind of phosphorus oxychloride synthesis 2-naphthalic sulfonic chloride provided by the present invention, comprises the steps:
1) 2-sodium naphthalene sulfonate, phosphorus oxychloride are added in solvent successively, obtain reaction solution a;
2) by step 1) gained reaction solution a is when temperature is 50～110 DEG C, reaction 4～12h, obtains mixed solution b;
3) by step 2) gained mixed solution b continue evaporation after, more successively through washing, filter, underpressure distillation, obtain 2-naphthalic sulfonic chloride.
Preferably, the method for a kind of phosphorus oxychloride synthesis 2-naphthalic sulfonic chloride, comprises the following steps:
1) 2-sodium naphthalene sulfonate, phosphorus oxychloride are added in solvent successively, obtain reaction solution a;
2) by step 1) gained reaction solution a is when temperature is 60～90 DEG C, reaction 5～9h, obtains mixed solution b;
3) by step 2) gained mixed solution b continue evaporation after, more successively through washing, filter, underpressure distillation, obtain 2-naphthalic sulfonic chloride.
Further, described step 1) in, solvent is one or more in methylene dichloride, ethylene dichloride, chloroform, tetracol phenixin, phosphorus oxychloride.
Preferably, described solvent is phosphorus oxychloride.
Further, described step 1) in, the mol ratio of 2-sodium naphthalene sulfonate and phosphorus oxychloride is 2-sodium naphthalene sulfonate: phosphorus oxychloride=1:1～5.
Preferably, described step 1) in, the mol ratio of 2-sodium naphthalene sulfonate and phosphorus oxychloride is 2-sodium naphthalene sulfonate: phosphorus oxychloride=1:1.5～3.
Further, described step 1) in, the mol ratio of 2-sodium naphthalene sulfonate and solvent is 2-sodium naphthalene sulfonate: solvent=1:1～5.
Preferably, described step 1) in, the mol ratio of 2-sodium naphthalene sulfonate and solvent is 2-sodium naphthalene sulfonate: solvent=1:1.5～3.
Compared with prior art, tool of the present invention has the following advantages:
Its one, the present invention is simple to operate, and chloride reagent phosphorus oxychloride used is gentleer, phosphorus oxychloride not only can be used as chloride reagent, it is possible to as the solvent in reaction, avoids and adds other multiple organic solvents, product is easily separated, and substantially increases the purity of product;
Its two, raw materials cost of the present invention is low, and solvent species is few, and environmental pollution is little, and the receipts rate of product 2-naphthalic sulfonic chloride can reach more than 95%, substantially increases the receipts rate of product, therefore, has good industrial applications prospect.
Accompanying drawing explanation
Fig. 1 is the infrared spectrogram of the 2-naphthalic sulfonic chloride obtained by embodiment 1.
Embodiment
Below in conjunction with specific embodiment, the present invention is described in further detail.
Embodiment 1:
The present invention's phosphorus oxychloride synthesizes the method for 2-naphthalic sulfonic chloride, comprises the following steps:
1) by 346g (1.5mol) 2-sodium naphthalene sulfonate, the mixing of 690g (4.5mol) phosphorus oxychloride, reaction solution a is obtained;
2) by step 1) gained reaction solution a is when temperature is 70 DEG C, reaction 6h, obtains mixed solution b;
3) by step 2) after gained mixed solution b continues to steam unnecessary phosphorus oxychloride, more successively through washing, filter, underpressure distillation, obtain 2-naphthalic sulfonic chloride.
Through calculating, it is 95% that aforesaid method prepares the product yield of 2-naphthalic sulfonic chloride.
Embodiment 2:
The present invention's phosphorus oxychloride synthesizes the method for 2-naphthalic sulfonic chloride, comprises the following steps:
1) 346g (1.5mol) 2-sodium naphthalene sulfonate, 690g (4.5mol) phosphorus oxychloride are added in 3.0mol chloroform successively, obtain reaction solution a;
2) by step 1) gained reaction solution a is when temperature is 75 DEG C, reaction 6h, obtains mixed solution b;
3) by step 2) after gained mixed solution b continues to steam unnecessary phosphorus oxychloride and chloroform, more successively through washing, filter, underpressure distillation, obtain 2-naphthalic sulfonic chloride.
Through calculating, it is 94.3% that aforesaid method prepares the product yield of 2-naphthalic sulfonic chloride.
Embodiment 3:
The present invention's phosphorus oxychloride synthesizes the method for 2-naphthalic sulfonic chloride, comprises the following steps:
1) 346g (1.5mol) 2-sodium naphthalene sulfonate, 462g (3.0mol) phosphorus oxychloride are added in 3.5mol methylene dichloride successively, obtain reaction solution a;
2) by step 1) gained reaction solution a is when temperature is 80 DEG C, reaction 7h, obtains mixed solution b;
3) by step 2) after gained mixed solution b continues to steam unnecessary phosphorus oxychloride and methylene dichloride, more successively through washing, filter, underpressure distillation, obtain 2-naphthalic sulfonic chloride.
Through calculating, it is 93.7% that aforesaid method prepares the product yield of 2-naphthalic sulfonic chloride.
Embodiment 4:
The present invention's phosphorus oxychloride synthesizes the method for 2-naphthalic sulfonic chloride, comprises the following steps:
1) 230g (1.0mol) 2-sodium naphthalene sulfonate, 154g (1.0mol) phosphorus oxychloride are added in 2.5mol methylene dichloride successively, obtain reaction solution a;
2) by step 1) gained reaction solution a is when temperature is 80 DEG C, reaction 8h, obtains mixed solution b;
3) by step 2) after gained mixed solution b continues to steam unnecessary phosphorus oxychloride and methylene dichloride, more successively through washing, filter, underpressure distillation, obtain 2-naphthalic sulfonic chloride.
Through calculating, it is 93.5% that aforesaid method prepares the product yield of 2-naphthalic sulfonic chloride.
Embodiment 5:
The present invention's phosphorus oxychloride synthesizes the method for 2-naphthalic sulfonic chloride, comprises the following steps:
1) 346g (1.5mol) 2-sodium naphthalene sulfonate, 308g (2.0mol) phosphorus oxychloride are added 3.0mol tetracol phenixin successively, obtain reaction solution a;
2) by step 1) gained reaction solution a is when temperature is 60 DEG C, reaction 9h, obtains mixed solution b;
3) by step 2) after gained mixed solution b continues to steam unnecessary phosphorus oxychloride and tetracol phenixin, more successively through washing, filter, underpressure distillation, obtain 2-naphthalic sulfonic chloride.
Through calculating, it is 94.6% that aforesaid method prepares the product yield of 2-naphthalic sulfonic chloride.
Embodiment 6:
The present invention's phosphorus oxychloride synthesizes the method for 2-naphthalic sulfonic chloride, comprises the following steps:
1) just 230g (1.0mol) 2-sodium naphthalene sulfonate, 770g (5.0mol) phosphorus oxychloride add in 5.0mol ethylene dichloride successively, obtain reaction solution a;
2) by step 1) gained reaction solution a is when temperature is 110 DEG C, reaction 12h, obtains mixed solution b;
3) by step 2) after gained mixed solution b continues to steam unnecessary phosphorus oxychloride and ethylene dichloride, more successively through washing, filter, underpressure distillation, obtain 2-naphthalic sulfonic chloride.
Through calculating, it is 95.6% that aforesaid method prepares the product yield of 2-naphthalic sulfonic chloride.
Embodiment 7:
The present invention's phosphorus oxychloride synthesizes the method for 2-naphthalic sulfonic chloride, comprises the following steps:
1) by 346g (1.5mol) 2-sodium naphthalene sulfonate, the mixing of 770g (5mol) phosphorus oxychloride, reaction solution a is obtained;
2) by step 1) gained reaction solution a is when temperature is 50 DEG C, reaction 4h, obtains mixed solution b;
3) by step 2) after gained mixed solution b continues to steam unnecessary phosphorus oxychloride, more successively through washing, filter, underpressure distillation, obtain 2-naphthalic sulfonic chloride.
Through calculating, it is 93.8% that aforesaid method prepares the product yield of 2-naphthalic sulfonic chloride.
Embodiment 8:
The present invention's phosphorus oxychloride synthesizes the method for 2-naphthalic sulfonic chloride, comprises the following steps:
1) 346g (1.5mol) 2-sodium naphthalene sulfonate, 770g (5mol) phosphorus oxychloride are added in 2.25mol chloroform successively, obtain reaction solution a;
2) by step 1) gained reaction solution a is when temperature is 90 DEG C, reaction 9h, obtains mixed solution b;
3) by step 2) after gained mixed solution b continues to steam unnecessary phosphorus oxychloride and chloroform, more successively through washing, filter, underpressure distillation, obtain 2-naphthalic sulfonic chloride.
Through calculating, it is 95.8% that aforesaid method prepares the product yield of 2-naphthalic sulfonic chloride.
Embodiment 9: effect example
2-naphthalic sulfonic chloride prepared by embodiment 1 is carried out Infrared spectroscopy, sulfuryl chlorio vibration absorption peak has occurred as shown in Figure 1, obtain the good 2-naphthalic sulfonic chloride of homogeneity.
The above, be only the specific embodiment of the present invention, it should be noted that any those of ordinary skill in the art are in the technical scope disclosed by the present invention, and the change that can expect easily or replacement, all should be encompassed within protection scope of the present invention.
Claims (8)
1. one kind is synthesized the method for 2-naphthalic sulfonic chloride by phosphorus oxychloride, it is characterised in that, comprise the following steps:
1) 2-sodium naphthalene sulfonate, phosphorus oxychloride are added in solvent successively, obtain reaction solution a;
2) by step 1) gained reaction solution a is when temperature is 50～110 DEG C, reaction 4～12h, obtains mixed solution b;
3) by step 2) gained mixed solution b continue evaporation after, more successively through washing, filter, underpressure distillation, obtain 2-naphthalic sulfonic chloride.
2. the method for phosphorus oxychloride according to claim 1 synthesis 2-naphthalic sulfonic chloride, it is characterised in that, comprise the following steps:
1) 2-sodium naphthalene sulfonate, phosphorus oxychloride are added in solvent successively, obtain reaction solution a;
2) by step 1) gained reaction solution a is when temperature is 60～90 DEG C, reaction 5～9h, obtains mixed solution b;
3) by step 2) gained mixed solution b continue evaporation after, more successively through washing, filter, underpressure distillation, obtain 2-naphthalic sulfonic chloride.
3. the method for phosphorus oxychloride according to claim 1 and 2 synthesis 2-naphthalic sulfonic chloride, it is characterised in that, described step 1) in, solvent is one or more in methylene dichloride, ethylene dichloride, chloroform, tetracol phenixin, phosphorus oxychloride.
4. the method for phosphorus oxychloride according to claim 3 synthesis 2-naphthalic sulfonic chloride, it is characterised in that, described solvent is phosphorus oxychloride.
5. the method for phosphorus oxychloride according to claim 1 and 2 synthesis 2-naphthalic sulfonic chloride, it is characterised in that, described step 1) in, the mol ratio of 2-sodium naphthalene sulfonate and phosphorus oxychloride is 2-sodium naphthalene sulfonate: phosphorus oxychloride=1:1～5.
6. the method for phosphorus oxychloride according to claim 5 synthesis 2-naphthalic sulfonic chloride, it is characterised in that, described step 1) in, the mol ratio of 2-sodium naphthalene sulfonate and phosphorus oxychloride is 2-sodium naphthalene sulfonate: phosphorus oxychloride=1:1.5～3.
7. the method for phosphorus oxychloride according to claim 1 and 2 synthesis 2-naphthalic sulfonic chloride, it is characterised in that, described step 1) in, the mol ratio of 2-sodium naphthalene sulfonate and solvent is 2-sodium naphthalene sulfonate: solvent=1:1～5.
8. the method for phosphorus oxychloride according to claim 7 synthesis 2-naphthalic sulfonic chloride, it is characterised in that, described step 1) in, the mol ratio of 2-sodium naphthalene sulfonate and solvent is 2-sodium naphthalene sulfonate: solvent=1:1.5～3.
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102976988A (en) * | 2012-12-24 | 2013-03-20 | 三门峡奥科化工有限公司 | Synthesis technique of 2-thionaphthol |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102976988A (en) * | 2012-12-24 | 2013-03-20 | 三门峡奥科化工有限公司 | Synthesis technique of 2-thionaphthol |
Non-Patent Citations (2)
| Title |
|---|
| SHINSAKU FUJITA: "A Convenient Preparation of Arenesulfonyl Chlorides from Sodium Sulfonates and Phosphoryl Chloride/Sulfolane", 《SYNTHESIS》 * |
| 文光亚等: "荧光保幼激素N-3,4-亚甲二氧基-苯基-β-萘磺酰胺的合成", 《山西大学学报》 * |
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Application publication date: 20160615 |