CN105130846A - Methyl 3-(cyanomethyl)benzoate synthetic method - Google Patents
Methyl 3-(cyanomethyl)benzoate synthetic method Download PDFInfo
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- CN105130846A CN105130846A CN201510533494.4A CN201510533494A CN105130846A CN 105130846 A CN105130846 A CN 105130846A CN 201510533494 A CN201510533494 A CN 201510533494A CN 105130846 A CN105130846 A CN 105130846A
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Abstract
The invention discloses a methyl 3-(cyanomethyl)benzoate synthetic method. The method comprises the following steps: taking m-toluic acid as a starting material, adding sulphone chloride for an acylation reaction, and flowing into liquid chlorine for a chlorination reaction, adding non-aqueous methanol dropwise for an esterification reaction to prepare ester, adding toluene and sodium cyanide into a cyanation reaction still, raising the temperature for backflow, adding the ester dropwise, carrying out backflow for 2 hours to prepare the methyl 3-(cyanomethyl)benzoate, and after the reaction, adding water to extract the methyl 3-(cyanomethyl)benzoate. The methyl 3-(cyanomethyl)benzoate synthetic method is high in yield, avoids serious three-waste pollution, and is suitable for industrial production.
Description
Technical field
The present invention relates to pharmaceutical chemistry technical field, particularly a cyanogen methyl-toluate synthetic method.
Background technology
Ketoprofen BP 93 is a kind of excellent anti-inflammatory analgesic, with a cyanogen methyl-toluate for starting raw material synthesis Ketoprofen BP 93 is an economy and eco-friendly route, but cyanogen methyl-toluate complex manufacturing between tradition, cost is higher, and yield is lower.For this reason, market is badly in need of a kind of simple to operate, with low cost and can industrial cyanogen methyl-toluate synthetic method.The present inventor's innovation and creation this application technology.
Summary of the invention
The object of the present invention is to provide that a kind of yield is high, cost is low, recycled, environmental protection, be applicable to industrial cyanogen methyl-toluate synthetic method.
The object of the invention is to be achieved through the following technical solutions:
Between cyanogen methyl-toluate synthetic method, take m-methyl benzoic acid as starting raw material, its synthetic route is as follows:
Its concrete steps are as follows:
A): by m-methyl benzoic acid (I) suction acylation kettle, add excess thionyl chloride acylation reaction, under 60-100 DEG C of condition, make acylate---m-methyl benzoyl formyl chloride (II).The sulfur oxychloride that Distillation recovery is excessive;
B): by m-methyl benzoyl formyl chloride (II) suction chlorination tank, temperature controls, under 110-170 DEG C of condition, to pass into liquid chlorine, control the 4.6%-22.9% that liquid chlorine intake is m-methyl benzoyl formyl chloride weight, obtain chloromethyl benzoic acid chlorides between part (III).
C): drip anhydrous methanol in chloromethyl benzoic acid chlorides (III) suction esterifying kettle between inciting somebody to action, under 30-65 DEG C of condition, carry out esterification make carboxylate---m-chloro methyl-toluate (IV); Esterification again in excessive methyl alcohol to esterifying kettle is steamed after esterification completes;
D): solvent methanol, quaternary ammonium salt catalyst, sodium cyanide are added cyanogenation still, be warming up to backflow, drip m-chloro methyl-toluate (IV), under 35-90 DEG C of condition, namely backflow makes a cyanogen methyl-toluate (V) for 0.5-3 hours, steams solvent methanol and recycles;
E): reaction terminate after, cooling, add water, toluene extraction between cyanogen methyl-toluate (V), steam solvent toluene and recycle, underpressure distillation collect finished product.
Cyanogen methyl-toluate synthetic method between as above, is characterized in that: the HCl tail gas produced in described step a), step b) and step c) is absorbed by water makes byproduct hydrochloric acid, the SO produced in described step a)
2tail gas passes into sodium hydroxide solution and makes byproduct S-WAT with for sale or separately use it for anything else.
Cyanogen methyl-toluate synthetic method between as above, is characterized in that: by the excessive sulfur oxychloride of Distillation recovery acidylate again to acylation kettle in described step a), make raw material reaction thing m-methyl benzoic acid (I) complete reaction.
Cyanogen methyl-toluate synthetic method between as above, be is characterized in that: had neither part nor lot in chlorination again in the m-methyl benzoyl formyl chloride (II) to chlorination tank of reaction in described step b) by Distillation recovery.
Cyanogen methyl-toluate synthetic method between as above, is characterized in that: in described step c), esterification steams esterification again in excessive methyl alcohol to esterifying kettle after completing.
Cyanogen methyl-toluate synthetic method between as above, is characterized in that: after described step d) reaction terminates, distilling off solvent methyl alcohol recycles to cyanogenation still.
Cyanogen methyl-toluate synthetic method between as above, is characterized in that: in described step e) after extraction, and the circulation of distilling off solvent toluene participates in extraction.
Cyanogen methyl-toluate synthetic method between as above, is characterized in that: the waste water in described step e) after pyrolytic decomposition again through biochemical treatment harmless emission to sewage collecting station.
The present invention, by control temperature and liquid chlorine intake, acidylates thing and is partially converted into muriate---and a chloromethyl benzoic acid chlorides, does not have impurity in a chloromethyl benzoic acid chlorides substantially.Because under high liquid chlorine intake state, a dichloromethyl Benzoyl chloride or a trichloromethyl Benzoyl chloride non-targeted impurity can be caused to produce in a large number, be unfavorable for the carrying out of subsequent reactions.Distillation recovery has neither part nor lot in m-methyl benzoyl formyl chloride chlorination again to chlorination tank of reaction, finally obtains chloromethyl benzoic acid chlorides between high-quality.
Reaction conditions of the present invention is gentle, and simple to operate, Matter Transfer is applied mechanically, and cost is low, and yield is high, and quality is good, environmental friendliness, is applicable to suitability for industrialized production.In the present invention, within the reaction times can foreshorten to 2 hours by quaternary ammonium salt catalyst.By control temperature and liquid chlorine intake, acidylate thing and be partially converted into a chloromethyl benzoic acid chlorides, block side reaction and produce dichloromethyl Benzoyl chloride or a trichloromethyl Benzoyl chloride generation between non-targeted impurity.
Accompanying drawing explanation
Fig. 1 is FB(flow block) of the present invention.
Embodiment
Embodiment 1:
As Fig. 1, a cyanogen methyl-toluate synthetic method, take m-methyl benzoic acid as starting raw material, its synthetic route is as follows:
Its concrete steps are as follows:
A): by 400 parts of m-methyl benzoic acid (I) suction chlorination tanks, add 410 parts of sulfur oxychlorides, under 70 DEG C of conditions, acylation reaction makes m-methyl benzoyl formyl chloride (II), and yield is 90-97%;
B): by m-methyl benzoyl formyl chloride (II) suction chlorination tank, the liquid chlorine of m-methyl benzoyl formyl chloride weight 4.6% is passed under keeping 125 DEG C of conditions, acidylate thing and be partially converted into muriate (III), Distillation recovery has neither part nor lot in m-methyl benzoyl formyl chloride chlorination again to chlorination tank of reaction, until finally obtain chloromethyl benzoic acid chlorides between high-quality (III);
C): drip 80 parts of anhydrous methanols in muriate (III) suction esterifying kettle, carry out esterification 40 DEG C of conditions and make carboxylate (IV), after esterification completes, steam excessive methyl alcohol; Yield is 89-96%;
D): solvent methanol, 15 parts of chlorinating benzyl triethylamines, 144 parts of sodium cyanides are added cyanogenation still, be warming up to backflow, dropping carboxylate (IV) refluxes and within 0.5 hour, makes a cyanogen methyl-toluate (V) under 80 DEG C of conditions, steams solvent methanol and recycles;
E): reaction terminate after, cooling, add water, toluene extraction between cyanogen methyl-toluate (V), steam solvent toluene and recycle, underpressure distillation collect finished product.Yield is 87-93%;
Wherein, the HCl tail gas produced in step a), step b) and step c) is absorbed by water and makes byproduct hydrochloric acid, the SO produced in step a)
2tail gas passes into sodium hydroxide solution and makes byproduct S-WAT with for sale or separately use it for anything else.By the excessive sulfur oxychloride of Distillation recovery acidylate again to acylation kettle in step a).Had neither part nor lot in chlorination again in the m-methyl benzoyl formyl chloride (II) to chlorination tank of reaction by Distillation recovery in step b).In step c), esterification steams esterification again in excessive methyl alcohol to esterifying kettle after completing.Add quaternary ammonium salt in step d) the reaction times to be shortened.After step d) reaction terminates, distilling off solvent methyl alcohol recycles to cyanogenation still.In step e) after extraction, the circulation of distilling off solvent toluene participates in extraction.Waste water in step e) after pyrolytic decomposition again through biochemical treatment harmless emission to sewage collecting station.
Embodiment 2:
As Fig. 1, a cyanogen methyl-toluate synthetic method, take m-methyl benzoic acid as starting raw material, its synthetic route is as follows:
Its concrete steps are as follows:
A): by 400 parts of m-methyl benzoic acid (I) suction chlorination tanks, add 370 parts of sulfur oxychlorides, under 80 DEG C of conditions, acylation reaction makes m-methyl benzoyl formyl chloride (II), and yield is 90-97%;
B): by m-methyl benzoyl formyl chloride (II) suction chlorination tank, the liquid chlorine of m-methyl benzoyl formyl chloride weight 13.8% is passed under keeping 145 DEG C of conditions, acidylate thing and be partially converted into muriate (III), Distillation recovery has neither part nor lot in m-methyl benzoyl formyl chloride chlorination again to chlorination tank of reaction, until finally obtain chloromethyl benzoic acid chlorides between high-quality (III);
C): drip 80 parts of anhydrous methanols in muriate (III) suction esterifying kettle, carry out esterification 60 DEG C of conditions and make carboxylate (IV), steam excessive methyl alcohol after esterification completes, yield is 89-96%;
D): 165 parts of solvent methanols, 15 parts of Tetrabutyl amonium bromides, 144 parts of sodium cyanides are added cyanogenation still, be warming up to backflow, dropping carboxylate (IV) refluxes and within 2 hours, makes a cyanogen methyl-toluate (V) under 65 DEG C of conditions, steams solvent methanol and recycles;
E): reaction terminate after, cooling, add water, toluene extraction between cyanogen methyl-toluate (V), steam solvent toluene and recycle, underpressure distillation collect finished product.Yield is 87-93%; Under with embodiment 1.
Embodiment 3:
As Fig. 1, a cyanogen methyl-toluate synthetic method, take m-methyl benzoic acid as starting raw material, its synthetic route is as follows:
Its concrete steps are as follows:
A): by 400 parts of m-methyl benzoic acid (I) suction chlorination tanks, add 380 parts of sulfur oxychlorides, under 60 DEG C of conditions, acylation reaction makes m-methyl benzoyl formyl chloride (II), and yield is 90-97%;
B): by m-methyl benzoyl formyl chloride (II) suction chlorination tank, the liquid chlorine of m-methyl benzoyl formyl chloride weight 17.8% is passed under keeping 170 DEG C of conditions, acidylate thing and be partially converted into muriate (III), Distillation recovery has neither part nor lot in m-methyl benzoyl formyl chloride chlorination again to chlorination tank of reaction, until finally obtain chloromethyl benzoic acid chlorides between high-quality (III);
C): in muriate (III) suction esterifying kettle, drip 80-120 part anhydrous methanol, carry out esterification 35 DEG C of conditions and make carboxylate (IV), after esterification completes, steam excessive methyl alcohol; Yield is 89-96%;
D): by 165 parts of solvent methanols, 15 parts of 4-butyl ammonium hydrogen sulfates (TBAB), 145 parts of sodium cyanides add cyanogenation still, be warming up to backflow, dropping carboxylate (IV) refluxes and within 3 hours, makes a cyanogen methyl-toluate (V) under 35 DEG C of conditions, steams solvent methanol and recycles;
E): reaction terminate after, cooling, add water, toluene extraction between cyanogen methyl-toluate (V), steam solvent toluene and recycle, underpressure distillation collect finished product.Yield is 87-93%; Under with embodiment 1.
Embodiment 4:
As Fig. 1, a cyanogen methyl-toluate synthetic method, take m-methyl benzoic acid as starting raw material, its synthetic route is as follows:
Its concrete steps are as follows:
A): by 400 parts of m-methyl benzoic acid (I) suction chlorination tanks, add 400 parts of sulfur oxychlorides acylation reaction under 100 DEG C of conditions and make m-methyl benzoyl formyl chloride (II), yield is 90-97%;
B): by m-methyl benzoyl formyl chloride (II) suction chlorination tank, the liquid chlorine of m-methyl benzoyl formyl chloride weight 22.9% is passed under keeping 110 DEG C of conditions, acidylate thing and be partially converted into muriate (III), Distillation recovery has neither part nor lot in m-methyl benzoyl formyl chloride chlorination again to chlorination tank of reaction, until finally obtain chloromethyl benzoic acid chlorides between high-quality (III);
C): in muriate (III) suction esterifying kettle, drip 80-120 part anhydrous methanol, carry out esterification 50 DEG C of conditions and make carboxylate (IV), after esterification completes, steam excessive methyl alcohol; Yield is 89-96%;
D): by 165 parts of solvent methanols, 15 parts of tri-n-octyl methyl ammonium chlorides or Dodecyl trimethyl ammonium chloride.144 parts of sodium cyanides add cyanogenation still, are warming up to backflow, and dropping carboxylate (IV) refluxes and within 1 hour, makes a cyanogen methyl-toluate (V) under 65 DEG C of conditions, steams solvent methanol and recycles;
E): reaction terminate after, cooling, add water, toluene extraction between cyanogen methyl-toluate (V), steam solvent toluene and recycle, underpressure distillation collect finished product.Yield is 85-93%; Under with embodiment 1.
The invention is not restricted to above-described embodiment.
Claims (9)
1. a cyanogen methyl-toluate synthetic method,
It is characterized in that:
A) by m-methyl benzoic acid (I) suction acylation kettle, add excess thionyl chloride, make raw material reaction thing m-methyl benzoic acid (I) complete reaction;
Acylation reaction generates acylate (m-methyl benzoyl formyl chloride) (II);
B) by m-methyl benzoyl formyl chloride (II) suction chlorination tank, pass into liquid chlorine and carry out chlorination reaction, control temperature and liquid chlorine intake, obtain chloromethyl benzoic acid chlorides between part) (III);
C) drip anhydrous methanol in chloromethyl benzoic acid chlorides (III) suction esterifying kettle between general, esterification generates carboxylate (m-chloro methyl-toluate) (IV);
D) solvent methanol, quaternary ammonium salt catalyst and sodium cyanide are added cyanogenation still, be warming up to backflow, then drip m-chloro methyl-toluate (IV) backflow and within 0.5-3 hours, namely make a cyanogen methyl-toluate (V); After reaction terminates, add toluene, water extraction, finished product (V) is collected in underpressure distillation;
E) finished product is collected in cyanogen methyl-toluate (V) underpressure distillation between d) obtaining.
2. according to claim 1 cyanogen methyl-toluate synthetic method, is characterized in that: the HCl tail gas produced in described step a), step b) and step c) is absorbed by water makes byproduct hydrochloric acid, the SO produced in described step a)
2tail gas passes into sodium hydroxide solution and makes byproduct S-WAT.
3. according to claim 1 cyanogen methyl-toluate synthetic method, is characterized in that: by the excessive sulfur oxychloride of Distillation recovery acidylate again to acylation kettle in described step a).
4. according to claim 1 cyanogen methyl-toluate synthetic method, it is characterized in that: in described step b), temperature controls at 110-170 DEG C; Liquid chlorine intake is the 4.6%-22.9% of m-methyl benzoyl formyl chloride weight of material.
5. according to claim 1 cyanogen methyl-toluate synthetic method, is characterized in that: had neither part nor lot in chlorination again in the m-methyl benzoyl formyl chloride (II) to chlorination tank of reaction in described step b) by Distillation recovery.
6. according to claim 1 cyanogen methyl-toluate synthetic method, is characterized in that: in described step c), esterification steams esterification again in excessive methyl alcohol to esterifying kettle after completing.
7. according to claim 1 cyanogen methyl-toluate synthetic method, is characterized in that: after described step d) reaction terminates, distilling off solvent methyl alcohol recycles to cyanogenation still.
8. according to claim 1 cyanogen methyl-toluate synthetic method, is characterized in that: in described step d) after extraction, and the circulation of distilling off solvent toluene participates in extraction.
9. according to claim 1 cyanogen methyl-toluate synthetic method, is characterized in that: the waste water in described step d) after pyrolytic decomposition again through biochemical treatment harmless emission to sewage collecting station.
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106928092A (en) * | 2017-02-28 | 2017-07-07 | 上海微巨实业有限公司 | The preparation method of one inter-species cyanogen methyl toluate |
| CN107400052A (en) * | 2017-07-21 | 2017-11-28 | 淄博飞源化工有限公司 | A kind of o-, m-, to trifluoromethyl benzoic acid methyl ester synthetic method |
| CN110156718A (en) * | 2019-06-21 | 2019-08-23 | 科迈化工股份有限公司 | A method of using liquid chlorine as oxidant continuous production accelerator D CBS |
| CN110818555A (en) * | 2019-11-18 | 2020-02-21 | 怀化泰通新材料科技有限公司 | Preparation method of 2-4-6-trimethylbenzoyl chloride |
| CN110818557A (en) * | 2019-11-13 | 2020-02-21 | 江苏快达农化股份有限公司 | Synthesis method of o-chloromethyl benzoyl chloride |
| CN111675631A (en) * | 2020-06-24 | 2020-09-18 | 湖北仙盛科技股份有限公司 | Synthesis process of cyano ketoprofen |
| CN111909024A (en) * | 2019-05-08 | 2020-11-10 | 金凯(辽宁)化工有限公司 | Preparation method of 4-formylbenzoic acid |
| CN116143656A (en) * | 2023-02-22 | 2023-05-23 | 湖北仙盛科技股份有限公司 | Preparation method of m-cyano methyl benzoate |
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Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106928092A (en) * | 2017-02-28 | 2017-07-07 | 上海微巨实业有限公司 | The preparation method of one inter-species cyanogen methyl toluate |
| CN106928092B (en) * | 2017-02-28 | 2019-02-15 | 上海微巨实业有限公司 | The preparation method of one inter-species cyanogen methyl toluate |
| CN107400052A (en) * | 2017-07-21 | 2017-11-28 | 淄博飞源化工有限公司 | A kind of o-, m-, to trifluoromethyl benzoic acid methyl ester synthetic method |
| CN107400052B (en) * | 2017-07-21 | 2020-05-01 | 淄博飞源化工有限公司 | Synthesis method of methyl o-, m-and p-trifluoromethylbenzoate |
| CN111909024A (en) * | 2019-05-08 | 2020-11-10 | 金凯(辽宁)化工有限公司 | Preparation method of 4-formylbenzoic acid |
| CN111909024B (en) * | 2019-05-08 | 2022-08-02 | 金凯(辽宁)生命科技股份有限公司 | Preparation method of 4-formylbenzoic acid |
| CN110156718A (en) * | 2019-06-21 | 2019-08-23 | 科迈化工股份有限公司 | A method of using liquid chlorine as oxidant continuous production accelerator D CBS |
| CN110818557A (en) * | 2019-11-13 | 2020-02-21 | 江苏快达农化股份有限公司 | Synthesis method of o-chloromethyl benzoyl chloride |
| CN110818555A (en) * | 2019-11-18 | 2020-02-21 | 怀化泰通新材料科技有限公司 | Preparation method of 2-4-6-trimethylbenzoyl chloride |
| CN111675631A (en) * | 2020-06-24 | 2020-09-18 | 湖北仙盛科技股份有限公司 | Synthesis process of cyano ketoprofen |
| CN116143656A (en) * | 2023-02-22 | 2023-05-23 | 湖北仙盛科技股份有限公司 | Preparation method of m-cyano methyl benzoate |
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Inventor after: Yuan Hua Inventor after: Wu Yuanxin Inventor after: Du Zhiping Inventor after: Shao Xinhua Inventor after: He Zhengjiang Inventor after: Xu Yahua Inventor after: Xu Baohua Inventor before: Shao Xinhua Inventor before: He Zhengjiang Inventor before: Xu Yahua Inventor before: Xu Baohua |
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Effective date of registration: 20160602 Address after: 430073, No. 693 hung Chu street, Hubei, Wuhan Applicant after: Wuhan Institute of Technology Applicant after: Hubei Sheng Sheng Polytron Technologies Inc Address before: What village 433000 Chong town mayor Xiantao in Hubei Province Applicant before: Hubei Xiansheng Technology Co., Ltd. |
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Application publication date: 20151209 |