CN104072358A - Method for preparing 3,4,5,6-tetrafluorophthalic acid - Google Patents
Method for preparing 3,4,5,6-tetrafluorophthalic acid Download PDFInfo
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- CN104072358A CN104072358A CN201410317287.0A CN201410317287A CN104072358A CN 104072358 A CN104072358 A CN 104072358A CN 201410317287 A CN201410317287 A CN 201410317287A CN 104072358 A CN104072358 A CN 104072358A
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- pressure
- ptfe phthalate
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/06—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid amides
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/62—Preparation of compounds containing amino groups bound to a carbon skeleton by cleaving carbon-to-nitrogen, sulfur-to-nitrogen, or phosphorus-to-nitrogen bonds, e.g. hydrolysis of amides, N-dealkylation of amines or quaternary ammonium compounds
Abstract
The invention provides a method for preparing a 3,4,5,6-tetrafluorophthalic acid. N-methyl tetrafluorophthalimide is subjected to catalytic hydrolysis by a catalyst to generate the 3,4,5,6-tetrafluorophthalic acid at the pressure of 0.5-3.0kg/cm<2> and the temperature of 106-140 DEG C. By adopting the technical scheme disclosed by the invention, waste sulfuric acid is avoided, the reacted by-product methylamine can be applied to recovering and preparing the raw material N-methyl tetrafluorophthalimide, the pressure to the environment is greatly relieved, and the production cost is also significantly reduced when the yield of the product is improved.
Description
Technical field
The invention belongs to the field of chemical synthesis, be specifically related to a kind of green clean 3,4,5,6-ptfe phthalate preparation method.
Background technology
3,4,5,6-ptfe phthalate, for preparing the key intermediate of the fluoroquinolone antibiotics such as Ofloxacine USP 23, the numbering of structural formula and carbon is as follows:
As " a kind of 2,3,4, the preparation of 5-phenyl tetrafluoride formyl chloride " (CN102627553A) described in, its synthetic method is that N-methyl tetrafluoro phthalic imidine (1) is hydrolyzed and makes 3,4,5 in aqueous sulfuric acid, 6-ptfe phthalate (2), its chemical equation is as follows:
Adopt this technique, raw material supply is secure, and processing condition are gentleer, and yield, in 85% left and right, is relatively applicable to suitability for industrialized production.But can produce in process of production the Waste Sulfuric Acid aqueous solution that a large amount of very unmanageable concentration is 50% left and right, wastewater treatment difficulty is very large, and cost is very high, has restricted its application in suitability for industrialized production.
Summary of the invention
In order to solve the technological deficiency of above-mentioned existence, the object of this invention is to provide a kind of preparation method of 3,4,5,6-ptfe phthalate, avoided the generation of unmanageable Waste Sulfuric Acid, and yield also increases.
In order to realize above-mentioned technical purpose, the present invention has adopted following technical scheme:
A kind of 3,4,5,6-ptfe phthalate preparation method, by N-methyl tetrafluoro phthalic imidine (1) at 0.5～3.0kg/cm
2pressure and the temperature of 106～140 DEG C under generate 3,4,5,6-ptfe phthalate (2) through catalyst hydrolysis.
Chemical equation is as follows:
Preferably, N-methyl tetrafluoro phthalic imidine is at 1.5～2.5kg/cm
2pressure and the temperature of 115～135 DEG C under hydrolysis generate 3,4,5,6-ptfe phthalate.
Described catalyzer is tosic acid, and the consumption of tosic acid is 0.5～1.0% of N-methyl tetrafluoro phthalic imidine quality.
Described N-methyl tetrafluoro phthalic imidine is 1:2～3 with the charging capacity ratio of water.
The present invention is owing to having adopted technique scheme, avoided the generation of Waste Sulfuric Acid, the by product methylamine of reaction can, for reclaiming raw materials N-methyl tetrafluoro phthalic imidine, alleviate the pressure to environment greatly, when product yield improves, production cost also significantly reduces.
Brief description of the drawings
Fig. 1 be the embodiment of the present invention 1 prepare 3,4,5, the nuclear-magnetism carbon spectrogram of 6-ptfe phthalate, wherein a figure is nuclear-magnetism carbon spectrum full figure, b figure is the partial enlarged drawing of chemical shift 110～170,118.1 is C-1, the chemical shift of C-2; 144.9 is C-3, the chemical shift of C-6; 141.4 is C-4, the chemical shift of C-5; 162.7 is C-7, and the chemical shift of C-8 is in full accord with standard spectrogram.
Embodiment
The following specific embodiments of the present invention is to make a detailed explanation.
Embodiment 1:
In hydrolysis autoclave pressure, add 100 kilograms of N-methyl tetrafluoro phthalic imidines, 300 kg of water, 0.8 kilogram of tosic acid, at pressure 0.4kg/cm
2, 102 DEG C of Water Under solutions of temperature, are cooled to 10 DEG C of left and right after middle control is qualified, stirring and crystallizing 2 hours, and whizzer is centrifugal, and 3,4,5,6-ptfe phthalate is dried and obtained to filter cake, yield 80.7%.
Embodiment 2:
In hydrolysis autoclave pressure, add 100 kilograms of N-methyl tetrafluoro phthalic imidines, 220 kg of water, 0.8 kilogram of tosic acid, at pressure 2.0kg/cm
2, 125 DEG C of Water Under solutions of temperature, are cooled to 10 DEG C of left and right after middle control is qualified, stirring and crystallizing 2 hours, and whizzer is centrifugal, and 3,4,5,6-ptfe phthalate is dried and obtained to filter cake, yield 93.5%.
Embodiment 3:
In hydrolysis autoclave pressure, add 100 kilograms of N-methyl tetrafluoro phthalic imidines, 200 kg of water, 0.8 kilogram of tosic acid, at pressure 3.2kg/cm
2, 145 DEG C of Water Under solutions of temperature, are cooled to 10 DEG C of left and right after middle control is qualified, stirring and crystallizing 2 hours, and whizzer is centrifugal, and 3,4,5,6-ptfe phthalate is dried and obtained to filter cake, yield 79.6%.
Embodiment 4:
In hydrolysis autoclave pressure, add 100 kilograms of N-methyl tetrafluoro phthalic imidines, 220 kg of water, 0.45 kilogram of tosic acid, at pressure 2.0kg/cm
2, 125 DEG C of Water Under solutions of temperature, are cooled to 10 DEG C of left and right after middle control is qualified, stirring and crystallizing 2 hours, and whizzer is centrifugal, and 3,4,5,6-ptfe phthalate is dried and obtained to filter cake, yield 80.4%.
Embodiment 5:
In hydrolysis autoclave pressure, add 100 kilograms of N-methyl tetrafluoro phthalic imidines, 220 kg of water, 1.8 kilograms of tosic acid, at pressure 2.0kg/cm
2, 125 DEG C of Water Under solutions of temperature, after middle control is qualified, are cooled to 10 DEG C of left and right, stirring and crystallizing 2h, and whizzer is centrifugal, and 3,4,5,6-ptfe phthalate is dried and obtained to filter cake, yield 92.9%.
From to embodiment 4 and embodiment 5, when pressure and temperature is while being preferred, the input amount of tosic acid is lower than 0.5% of N-methyl tetrafluoro phthalic imidine quality, and reaction yield reduces; The input amount of tosic acid is higher than 1.0% of N-methyl tetrafluoro phthalic imidine quality, and yield does not have considerable change, and unnecessary tosic acid can be to environment build-up of pressure on the contrary.
Above-mentioned embodiment is to be the restriction that this patent is comprised to scope in order better to make those skilled in the art can understand this patent, can not to be interpreted as; As long as any being equal to done according to spirit that this patent discloses changes or modify, all fall into the scope that this patent comprises.
Claims (5)
1. one kind 3,4,5, the preparation method of 6-ptfe phthalate, is characterized in that: by N-methyl tetrafluoro phthalic imidine at 0.5 ~ 3.0kg/cm
2pressure and the temperature of 106 ~ 140 DEG C under generate 3,4,5,6-ptfe phthalate through catalyst hydrolysis.
2. according to claim 1 a kind of 3,4,5, the preparation method of 6-ptfe phthalate, is characterized in that: N-methyl tetrafluoro phthalic imidine is at 1.5 ~ 2.5kg/cm
2pressure and the temperature of 115 ~ 135 DEG C under hydrolysis generate 3,4,5,6-ptfe phthalate.
3. according to claim 1 a kind of 3,4,5, the preparation method of 6-ptfe phthalate, is characterized in that: described catalyzer is tosic acid.
4. according to claim 3 a kind of 3,4,5, the preparation method of 6-ptfe phthalate, is characterized in that: the consumption of tosic acid is 0.5 ~ 1.0% of N-methyl tetrafluoro phthalic imidine quality.
5. according to claim 1 a kind of 3,4,5, the preparation method of 6-ptfe phthalate, is characterized in that: N-methyl tetrafluoro phthalic imidine with the charging capacity of water than being 1:2 ~ 3.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410317287.0A CN104072358A (en) | 2014-07-04 | 2014-07-04 | Method for preparing 3,4,5,6-tetrafluorophthalic acid |
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| Application Number | Priority Date | Filing Date | Title |
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| CN201410317287.0A CN104072358A (en) | 2014-07-04 | 2014-07-04 | Method for preparing 3,4,5,6-tetrafluorophthalic acid |
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| CN201410317287.0A Pending CN104072358A (en) | 2014-07-04 | 2014-07-04 | Method for preparing 3,4,5,6-tetrafluorophthalic acid |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105693507A (en) * | 2016-03-18 | 2016-06-22 | 浙江大学 | Synthesis method of 3, 4, 5, 6-tetrafluorophthalic acid |
| CN107778160A (en) * | 2016-10-29 | 2018-03-09 | 江苏沙星化工有限公司 | A kind of preparation method of 3,4,5,6 ptfe phthalate |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102627553A (en) * | 2012-03-21 | 2012-08-08 | 浙江沙星医药化工有限公司 | Preparation method of 2,3,4,5-tetrafluorobenzoyl chloride |
-
2014
- 2014-07-04 CN CN201410317287.0A patent/CN104072358A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102627553A (en) * | 2012-03-21 | 2012-08-08 | 浙江沙星医药化工有限公司 | Preparation method of 2,3,4,5-tetrafluorobenzoyl chloride |
Non-Patent Citations (2)
| Title |
|---|
| LAWRENCE B. FERTEL: "Process Improvements in the Synthesis of 2,4,5-Trifluorobenzoic Acid. Selective Hydrodefluorination of Tetrafluorophthalimides", 《ORGANIC PROCESS RESEARCH & DEVELOPMENT》 * |
| 蔡星伟等: "2,3,4,5-四氟苯甲酸的制备", 《化学工业与工程》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105693507A (en) * | 2016-03-18 | 2016-06-22 | 浙江大学 | Synthesis method of 3, 4, 5, 6-tetrafluorophthalic acid |
| CN105693507B (en) * | 2016-03-18 | 2018-04-06 | 浙江大学 | The synthetic method of 3,4,5,6 ptfe phthalates |
| CN107778160A (en) * | 2016-10-29 | 2018-03-09 | 江苏沙星化工有限公司 | A kind of preparation method of 3,4,5,6 ptfe phthalate |
| CN107778160B (en) * | 2016-10-29 | 2021-06-18 | 江苏沙星化工有限公司 | Preparation method of 3,4,5, 6-tetrafluorophthalic acid |
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