CN102329237A - Production process of 2-chloro-5-nitrobenzoic acid - Google Patents
Production process of 2-chloro-5-nitrobenzoic acid Download PDFInfo
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- CN102329237A CN102329237A CN201110174759A CN201110174759A CN102329237A CN 102329237 A CN102329237 A CN 102329237A CN 201110174759 A CN201110174759 A CN 201110174759A CN 201110174759 A CN201110174759 A CN 201110174759A CN 102329237 A CN102329237 A CN 102329237A
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- chloro
- acid
- nitrobenzoic acid
- nitrobenzoic
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Abstract
The invention relates to a production process of 2-chloro-5-nitrobenzoic acid. The production process is characterized in that 2-chloro-5-nitrobenzoic acid is prepared by the process steps of nitration, alkali dissolution, acid precipitation and the like based on o-chlorobenzoic acid as a raw material; and when nitration is carried out, concentrated sulfuric acid and o-chlorobenzoic acid are added in a nitration kettle in a weight ratio of (3.5-4.5):1 and reaction amount of nitric acid is dropwise added for reaction, so that a crude product is prepared; water and an alkali liquid are added in the crude product so as to carry out alkali dissolution; and acid precipitation is carried out on filtrate so as to obtain the finished product. The production process provided by the invention has reasonable design and strong operability, the purity of the prepared product is high, the chromatographic purity of the product is not less than 99.5%, the yield of the product is above 85%, and the requirement of industrial application can be met.
Description
Technical field
The present invention relates to a kind of technology of the 2-of preparation chloro-5-nitrobenzoic acid.
Background technology
The method for preparing 2-chloro-5-nitrobenzoic acid in the prior art is to adopt the nitrated back of 0-chloro-benzoic acid purified method; But owing to produce more 2-chloro-3-nitrobenzoic acid isomer when nitrated; Adopt conventional process for purification to be difficult to reach higher purity; Generally can only be controlled at about 99.0%, can't satisfy the needs of use.
Summary of the invention
Technical problem to be solved by this invention is the deficiency to prior art, and the production technique of the high 2-chloro-5-nitrobenzoic acid of a kind of technology product purity more reasonable, that produced is provided.
Technical problem to be solved by this invention is to realize through following technical scheme.The present invention is a kind of production technique of 2-chloro-5-nitrobenzoic acid, is characterized in that its step is following:
(1) nitrated: with the vitriol oil and 0-chloro-benzoic acid by weight 3.5～4.5: 1 drops into nitrating pot; The nitric acid of dropwise reaction amount, controlled temperature are at 30～40 ℃, after dropwising; More than the insulation 2h; The elutriation still is gone in the residual back discharging of the no 0-chloro-benzoic acid of thin-layer chromatography inspection of taking a sample, and 2-chloro-5-nitrobenzoic acid and 2-chloro-3-nitrobenzoyl acid crystal that reaction generates are separated out, and get bullion after the centrifuging;
(2) alkali dissolves: bullion is dropped into alkali dissolve still; The water that adds 3.5～4.5 times of amounts of bullion weight; Stirring is warming up to 60～70 ℃; Dropwise liquid is to pH=7.5, and 2-chloro-5-nitrobenzoic acid and the dissolving of 2-chloro-3-nitrobenzoic acid generate 2-chloro-5-nitrobenzoic acid sodium and 2-chloro-3-nitrobenzoic acid sodium with the NaOH reaction; Add proper amount of active carbon press filtration decolouring, must filtrate;
(3) acid out: will filtrate and drop into the acid out still; Drip mass concentration and be 50% salpeter solution to pH=2～3, be warming up to boiling, keep naturally cooling to 38～42 ℃ behind the 1h at least; 2-chloro-5-nitrobenzoic acid is separated out; Centrifugal, washing in 0.06MP, 80～90 ℃ of oven dry down, get finished product with the bipyramid Vacuumdrier.
The main chemical reactions equation that relates in the production process is following:
1, nitration reaction:
2, alkali dissolves reaction:
2-chloro-5-nitrobenzoic acid+2-chloro-3-nitrobenzoic acid+2NaOH → 2-chloro-5-nitrobenzoic acid sodium+2-chloro-3-nitrobenzoic acid sodium+2H
2O.
3, acid precipitation reaction:
2-chloro-5-nitrobenzoic acid sodium+2-chloro-3-nitrobenzoic acid sodium+2HNO
3→ 2-chloro-5-nitrobenzoic acid+2-chloro-3-nitrobenzoic acid+2NaNO
3
Through test determination, nitrated workshop section transformation efficiency is about 92% in the technology of the present invention, the ratio of the 2-chloro-5-nitrobenzoic acid that generates and 2-chloro-3-nitrobenzoic acid be about 95: 5; It is 96% that alkali dissolves workshop section's transformation efficiency; Acid out workshop section transformation efficiency is 98%.
Compared with prior art, the advantage of the present invention's technology is: process step design of the present invention is more reasonable, workable, and prepared product gas purity is higher, and its chromatographic purity is not less than 99.5%, and yield is more than 85%; Can satisfy the needs of industrial application.
Embodiment
Below, further describe concrete technical scheme of the present invention, so that those skilled in the art understands the present invention further, and do not constitute restriction to its right.
Embodiment 1, a kind of production technique of 2-chloro-5-nitrobenzoic acid, and its step is following:
(1) nitrated: the vitriol oil and 0-chloro-benzoic acid were dropped into nitrating pot by weight 3.5: 1; The nitric acid of dropwise reaction amount, controlled temperature are at 30 ℃, after dropwising; More than the insulation 2h; The elutriation still is gone in the residual back discharging of the no 0-chloro-benzoic acid of thin-layer chromatography inspection of taking a sample, and 2-chloro-5-nitrobenzoic acid and 2-chloro-3-nitrobenzoyl acid crystal that reaction generates are separated out, and get bullion after the centrifuging;
(2) alkali dissolves: bullion is dropped into alkali dissolve still; The water that adds 3.5 times of amounts of bullion weight; Stirring is warming up to 60 ℃; Dropwise liquid is to pH=7.5, and 2-chloro-5-nitrobenzoic acid and the dissolving of 2-chloro-3-nitrobenzoic acid generate 2-chloro-5-nitrobenzoic acid sodium and 2-chloro-3-nitrobenzoic acid sodium with the NaOH reaction; Add proper amount of active carbon press filtration decolouring, must filtrate;
(3) acid out: will filtrate and drop into the acid out still; Drip mass concentration and be 50% salpeter solution to pH=2, be warming up to boiling, keep naturally cooling to 38 ℃ behind the 1h at least; 2-chloro-5-nitrobenzoic acid is separated out; Centrifugal, washing in 0.06MP, 80 ℃ of oven dry down, get finished product with the bipyramid Vacuumdrier;
Through detecting, the chromatographic purity of the finished product that present embodiment makes is 99.5%, and yield is 85%.
Embodiment 2, a kind of production technique of 2-chloro-5-nitrobenzoic acid, and its step is following:
(1) nitrated: the vitriol oil and 0-chloro-benzoic acid were dropped into nitrating pot by weight 4.5: 1; The nitric acid of dropwise reaction amount, controlled temperature are at 40 ℃, after dropwising; More than the insulation 2h; The elutriation still is gone in the residual back discharging of the no 0-chloro-benzoic acid of thin-layer chromatography inspection of taking a sample, and 2-chloro-5-nitrobenzoic acid and 2-chloro-3-nitrobenzoyl acid crystal that reaction generates are separated out, and get bullion after the centrifuging;
(2) alkali dissolves: bullion is dropped into alkali dissolve still; The water that adds 4.5 times of amounts of bullion weight; Stirring is warming up to 70 ℃; Dropwise liquid is to pH=7.5, and 2-chloro-5-nitrobenzoic acid and the dissolving of 2-chloro-3-nitrobenzoic acid generate 2-chloro-5-nitrobenzoic acid sodium and 2-chloro-3-nitrobenzoic acid sodium with the NaOH reaction; Add proper amount of active carbon press filtration decolouring, must filtrate;
(3) acid out: will filtrate and drop into the acid out still; Drip mass concentration and be 50% salpeter solution to pH=3, be warming up to boiling, keep naturally cooling to 42 ℃ behind the 1h at least; 2-chloro-5-nitrobenzoic acid is separated out; Centrifugal, washing in 0.06MP, 90 ℃ of oven dry down, get finished product with the bipyramid Vacuumdrier.
Through detecting, the chromatographic purity of the finished product that present embodiment makes is 99.6%, and yield is 85.5%.
Embodiment 3, a kind of production technique of 2-chloro-5-nitrobenzoic acid, and its step is following:
(1) nitrated: the vitriol oil and 0-chloro-benzoic acid were dropped into nitrating pot by weight 4: 1; The nitric acid of dropwise reaction amount, controlled temperature are at 35 ℃, after dropwising; More than the insulation 2h; The elutriation still is gone in the residual back discharging of the no 0-chloro-benzoic acid of thin-layer chromatography inspection of taking a sample, and 2-chloro-5-nitrobenzoic acid and 2-chloro-3-nitrobenzoyl acid crystal that reaction generates are separated out, and get bullion after the centrifuging;
(2) alkali dissolves: bullion is dropped into alkali dissolve still; The water that adds 4 times of amounts of bullion weight stirs and is warming up to 65 ℃, and dropwise liquid is to pH=7.5; 2-chloro-5-nitrobenzoic acid and the dissolving of 2-chloro-3-nitrobenzoic acid generate 2-chloro-5-nitrobenzoic acid sodium and 2-chloro-3-nitrobenzoic acid sodium with the NaOH reaction; Add proper amount of active carbon press filtration decolouring, must filtrate;
(3) acid out: will filtrate and drop into the acid out still; Drip mass concentration and be 50% salpeter solution to pH=2.5, be warming up to boiling, keep naturally cooling to 40 ℃ behind the 1h at least; 2-chloro-5-nitrobenzoic acid is separated out; Centrifugal, washing in 0.06MP, 85 ℃ of oven dry down, get finished product with the bipyramid Vacuumdrier;
Through detecting, the chromatographic purity of the finished product that present embodiment makes is 99.65%, and yield is 86%.
Claims (1)
1. the production technique of a 2-chloro-5-nitrobenzoic acid is characterized in that its step is following:
(1) nitrated: with the vitriol oil and 0-chloro-benzoic acid by weight 3.5 ~ 4.5: 1 drops into nitrating pot; The nitric acid of dropwise reaction amount, controlled temperature are at 30 ~ 40 ℃, after dropwising; More than the insulation 2h; The elutriation still is gone in the residual back discharging of the no 0-chloro-benzoic acid of thin-layer chromatography inspection of taking a sample, and 2-chloro-5-nitrobenzoic acid and 2-chloro-3-nitrobenzoyl acid crystal that reaction generates are separated out, and get bullion after the centrifuging;
(2) alkali dissolves: bullion is dropped into alkali dissolve still; The water that adds 3.5 ~ 4.5 times of amounts of bullion weight; Stirring is warming up to 60 ~ 70 ℃; Dropwise liquid is to pH=7.5, and 2-chloro-5-nitrobenzoic acid and the dissolving of 2-chloro-3-nitrobenzoic acid generate 2-chloro-5-nitrobenzoic acid sodium and 2-chloro-3-nitrobenzoic acid sodium with the NaOH reaction; Add proper amount of active carbon press filtration decolouring, must filtrate;
(3) acid out: will filtrate and drop into the acid out still; Drip mass concentration and be 50% salpeter solution to pH=2 ~ 3, be warming up to boiling, keep naturally cooling to 38 ~ 42 ℃ behind the 1h at least; 2-chloro-5-nitrobenzoic acid is separated out; Centrifugal, washing in 0.06MP, 80 ~ 90 ℃ of oven dry down, get finished product with the bipyramid Vacuumdrier.
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| CN201110174759A CN102329237A (en) | 2011-06-24 | 2011-06-24 | Production process of 2-chloro-5-nitrobenzoic acid |
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| CN201110174759A CN102329237A (en) | 2011-06-24 | 2011-06-24 | Production process of 2-chloro-5-nitrobenzoic acid |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106397209A (en) * | 2016-08-30 | 2017-02-15 | 枣阳凤泽精细化工有限公司 | Preparation method of 2-chloride-5-nitrobenzoic acid |
| CN109096165A (en) * | 2018-08-28 | 2018-12-28 | 临沂华毅医药股份有限公司 | A kind of refining plant and technique of dithiodibenzoic acid |
Citations (5)
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| US3534089A (en) * | 1964-07-15 | 1970-10-13 | Chemische Werke Witten Gmbh | Process for the purification of para-hydroxymethylbenzoic acid |
| JPS63159353A (en) * | 1986-12-23 | 1988-07-02 | Central Glass Co Ltd | Nitro-substituted 4-trifluoromethylbenzoic acid and production thereof |
| CN1132197A (en) * | 1995-03-25 | 1996-10-02 | 上海中西药业股份有限公司 | 3,3'-azo-bi-(6-hydroxy benzoic acid) |
| CN1364754A (en) * | 2001-01-09 | 2002-08-21 | 中南大学 | Poly-basic aromatic carboxylic acid for flotation and its preparing method |
| CN1373117A (en) * | 2002-02-21 | 2002-10-09 | 泰兴市化工七厂 | Process for purifying hihg-content o-methylbenzoic acid |
-
2011
- 2011-06-24 CN CN201110174759A patent/CN102329237A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3534089A (en) * | 1964-07-15 | 1970-10-13 | Chemische Werke Witten Gmbh | Process for the purification of para-hydroxymethylbenzoic acid |
| JPS63159353A (en) * | 1986-12-23 | 1988-07-02 | Central Glass Co Ltd | Nitro-substituted 4-trifluoromethylbenzoic acid and production thereof |
| CN1132197A (en) * | 1995-03-25 | 1996-10-02 | 上海中西药业股份有限公司 | 3,3'-azo-bi-(6-hydroxy benzoic acid) |
| CN1364754A (en) * | 2001-01-09 | 2002-08-21 | 中南大学 | Poly-basic aromatic carboxylic acid for flotation and its preparing method |
| CN1373117A (en) * | 2002-02-21 | 2002-10-09 | 泰兴市化工七厂 | Process for purifying hihg-content o-methylbenzoic acid |
Non-Patent Citations (2)
| Title |
|---|
| 纪明中: "对硝基苯乙酮生产中废渣的回收", 《辽宁化工》 * |
| 贾建洪 等: "5-硝基水杨酸的合成新工艺研究", 《浙江工业大学学报》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106397209A (en) * | 2016-08-30 | 2017-02-15 | 枣阳凤泽精细化工有限公司 | Preparation method of 2-chloride-5-nitrobenzoic acid |
| CN109096165A (en) * | 2018-08-28 | 2018-12-28 | 临沂华毅医药股份有限公司 | A kind of refining plant and technique of dithiodibenzoic acid |
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Application publication date: 20120125 |