CN114874092A - Method for preparing sodium salicylate through sodium phenolate carboxylation reaction - Google Patents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/15—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction of organic compounds with carbon dioxide, e.g. Kolbe-Schmitt synthesis
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
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Abstract
The invention relates to a method for preparing sodium salicylate by carboxylation reaction of sodium phenate, which takes acetone as a solvent and sodium phenate and carbon dioxide as raw materials, the sodium phenate is dissolved in the acetone to prepare sodium phenate solution, the sodium phenate and the carbon dioxide generate carboxylation reaction in an efficient gas-liquid dispersion mixing reactor, and the sodium salicylate is obtained by decompression flash evaporation and gas-solid separation of the reacted materials. Acetone is used as a solvent for the carboxylation reaction of the sodium phenolate, so that the carboxylation reaction of the sodium phenolate and carbon dioxide is changed from the traditional gas-solid multiphase reaction into the gas-liquid multiphase reaction, and meanwhile, the gas-liquid ratio is improved and the conversion per pass is also improved by adopting a high-efficiency gas-liquid dispersion mixing reactor. The unit operation processes of the invention are all sealed circulation systems, the whole process is safe and environment-friendly, and the solvent can be recycled, thus the invention is a clean production process for continuously producing sodium salicylate.
Description
Technical Field
The invention relates to a method for preparing sodium salicylate by carboxylation reaction of sodium phenolate in acetone solution, which is a process technology for preparing sodium salicylate by taking sodium phenolate and carbon dioxide as raw materials. Firstly, sodium phenate is dissolved in solvent acetone to prepare sodium phenate solution, then the obtained sodium phenate solution and carbon dioxide are subjected to gas-liquid phase carboxylation reaction in a high-efficiency gas-liquid dispersion mixing reactor, and the materials after the reaction are subjected to reduced pressure flash evaporation separation to obtain the sodium salicylate. Belongs to the technical field of fine chemical engineering and chemical engineering.
Background
1. Salicylic acid sodium salt
Sodium salicylate (also known as sodium o-hydroxybenzoate, 2-hydroxybenzoic acid monosodium salt, sodium salicylate and sodium salicylate), and its molecular formula is C 7 H 5 NaO 3 White flaky crystal or powder with molecular weight of 160.1 and melting point of 160-166 ℃. Odorless and turns pink after exposure to light. Is easily soluble in water, ethanol and glycerol, and 1g of sodium salicylate is dissolved in 0.9ml of water, 9.2ml of ethanol and 4ml of glycerol. Practically insoluble in ether, chloroform and benzene. The aqueous solution is slightly acidic, and the pH value is 5-6.
2. The prior gas-solid phase carboxylation reaction process for synthesizing sodium salicylate and the main problems existing in the prior process
The existing process for preparing sodium salicylate by using sodium phenolate and carbon dioxide as raw materials adopts Koble-Skhmitt reaction, and the gas-solid phase carboxylation reaction process technology is carried out on sodium phenolate solid and carbon dioxide gas under the conditions of reaction temperature controlled below 130 ℃ and pressurization.
The carboxylation reaction mainly has the following problems:
(1) contradiction between carboxylation reaction rate and selectivity: the carboxylation reaction is exothermic, the rate of Koble-Skhmit carboxylation reaction is increased along with the reaction temperature, and the rate of side reactions such as the generation of sodium p-hydroxybenzoate is also increased along with the increase of the reaction temperature. Therefore, there is a contradiction between the carboxylation reaction rate and selectivity, and how to realize the rapid and effective reaction of the gas phase reactant carbon dioxide and the sodium phenolate under the condition of high selectivity is a common technical problem.
(2) Gas-solid phase reaction system: in the process of generating sodium salicylate through carboxylation reaction of sodium phenate and carbon dioxide, the carbon dioxide is a gas-phase material, the sodium phenate is a solid-phase material, and the gas-solid-phase reaction system is a gas-solid-phase reaction system, so that the problems of small reaction rate, long reaction time, difficulty in heat transfer in the reaction process, easiness in local overheating to generate byproducts and the like are necessarily existed.
(3) The reaction selectivity is low, resulting in poor product quality: byproducts such as sodium p-hydroxybenzoate and the like are easily generated in the reaction process, and the product is difficult to separate and refine, so that the high-quality salicylic acid is difficult to prepare from the sodium salicylate.
(4) The preparation problem of fine-particle sodium phenolate is as follows: in order to increase the rate of sodium salicylate generation by carboxylation reaction of sodium phenolate and carbon dioxide, the method of reducing sodium phenolate particles is the most effective method for increasing carboxylation reaction speed and conversion rate, and in order to prepare fine sodium phenolate, the technical problem of preparing fine sodium phenolate particles is inevitably existed.
(5) Control of continuous steady state operation is difficult: because carbon dioxide and sodium phenolate are a gas-solid phase exothermic reaction system, the problems of reaction operation process control and reactor operation instability inevitably exist. Therefore, the intermittent operation mode is mainly used at present.
(6) The process safety and reliability are poor: the reactant sodium phenolate is easy to combust and explode after being dehydrated into dry powder, and the potential safety hazard of combustion and explosion exists in the preparation process of fine particle sodium phenolate.
Therefore, the development of a new process technology for preparing sodium salicylate through continuous carboxylation reaction of sodium phenolate and carbon dioxide is an urgent technical problem to be solved.
Disclosure of Invention
The invention provides a method for preparing sodium salicylate by carboxylation reaction of sodium phenolate in acetone solution.
The technical scheme for realizing the aim is as follows: a method for preparing sodium salicylate by carboxylation reaction of sodium phenate, which takes acetone as a solvent, sodium phenate and carbon dioxide as raw materials, adopts an efficient gas-liquid dispersion mixing reactor, and the sodium phenate and the carbon dioxide undergo gas-liquid phase carboxylation reaction to obtain the sodium salicylate, and comprises the following specific steps:
(1) solution preparation: in sodium phenolate solution preparation equipment, dissolving sodium phenolate in an organic solvent acetone to prepare a sodium phenolate solution;
(2) carboxylation reaction: in a high-efficiency gas-liquid dispersion mixing reactor, carrying out gas-liquid dispersion mixing on sodium phenolate solution and carbon dioxide, carrying out carboxylation reaction on the sodium phenolate and the carbon dioxide to generate sodium salicylate, and feeding the reacted materials to the next step;
(3) decompression flash evaporation: in a decompression flash evaporation device, performing decompression flash evaporation operation on the material subjected to the carboxylation reaction in the previous step, condensing and performing gas-liquid separation on a gas-phase material obtained by decompression flash evaporation to obtain acetone and carbon dioxide for recycling, and allowing other materials to enter the next step;
(4) gas-solid separation: and (3) in a gas-solid separation device, carrying out gas-solid separation on the material obtained in the last step, wherein the solid-phase material is the sodium salicylate.
Furthermore, in the sodium phenolate solution prepared in the first step, the volume ratio of the mass of the sodium phenolate to the volume of the acetone is 1.0kg: 4.0L-1.0 kg: 10.0L.
Further, the efficient gas-liquid dispersion mixing equipment in the second step of sodium phenolate carboxylation reaction process is any one of a static mixer, a jet mixer and a Venturi mixer, the molar ratio of sodium phenolate to carbon dioxide in the carboxylation reaction is 1.0: 1.2-1.0: 2.0, the reaction pressure is 0.4 MPa-0.8 MPa, and the reaction temperature is 80-120 ℃.
Further, the equipment for pressure reduction and flash evaporation in the third step is any one of a flash tank, a flash cooler or a flash tower, and the absolute pressure of operation is 0.02 MPa-0.08 MPa.
The sodium salicylate is prepared by the method mainly based on the following characteristics:
(1) the method fully utilizes the characteristic that acetone is a good solvent of sodium phenolate: the sodium phenolate has certain solubility in acetone, and the solubility of the sodium phenolate in the acetone is increased along with the increase of the temperature, and the solubility of the sodium phenolate in the acetone is about 22.0g/100ml under the condition of normal pressure reflux. By utilizing the characteristic that sodium phenolate is easily dissolved in acetone, in the carboxylation reaction process, a gas-liquid reaction is adopted to improve the rate and the selectivity of the carboxylation reaction.
(2) The efficient dispersion and mixing characteristics of the efficient gas-liquid mixer are fully utilized: static mixers, jet mixers, venturi mixers and the like can effectively realize the mixing of heterogeneous systems. By adopting the high-efficiency dispersion mixing technology, the gas-liquid ratio of the reaction of the carbon dioxide and the sodium phenolate can be improved, the micro-mixing of a gas phase and a liquid phase is realized, the gas-liquid contact specific surface area is improved, micro-bubbles and liquid drops with certain stability are formed, and the gas-liquid dispersion mixing speed and efficiency are remarkably improved in the aspect of dynamics.
(3) The characteristics of heat and mass simultaneous transfer and high transfer rate of the decompression flash equipment are fully utilized: the decompression flash process has the characteristic of simultaneous heat and mass transfer, and the heat and mass transfer rate is high.
The main process equipment for realizing the invention is as follows: high-efficiency gas-liquid dispersion mixing reactor, reduced pressure flash evaporation equipment, gas-solid separation equipment and the like.
The advantages of the invention are embodied in that:
(1) acetone is used as a solvent for the carboxylation reaction of the sodium phenolate, so that the carboxylation reaction of the sodium phenolate and the carbon dioxide is changed from the traditional gas-solid multiphase reaction into the gas-liquid multiphase reaction, the method has the remarkable advantages of high reaction efficiency and reaction conversion efficiency, and the preparation problem of the fine sodium phenolate particles is fundamentally solved.
(2) By adopting high-efficiency gas-liquid dispersion mixing equipment such as a static mixer, an injection mixer, a Venturi mixer and the like, the contradiction between the improvement of the gas-liquid ratio and the improvement of the single-pass conversion rate is solved from the aspect of dynamics, and the contradiction between the improvement of the gas-liquid ratio and the improvement of the single-pass conversion rate is fundamentally solved.
(3) The adoption of the reduced pressure flash evaporation equipment creates favorable conditions for the rapid cooling of the reacted materials and the rapid removal of the solvent, and fundamentally solves the technical problems of the design of an industrial scale reactor and the rapid cooling of the reacted materials and the rapid removal of the solvent in the continuous operation.
(4) Easy to realize continuous operation. The gas-liquid dispersion mixing, decompression flash evaporation and solid-liquid separation technology can be continuously operated, and compared with intermittent operation, the continuous operation has the outstanding advantages that the product quality is stable and easy to control, thereby creating favorable conditions for later separation and refining.
(5) The recycling of the solvent is realized. The acetone is adopted to dissolve the sodium phenolate, so that the carboxylation reaction of the sodium phenolate and the carbon dioxide is changed from the traditional gas-solid multiphase reaction into the gas-liquid multiphase reaction, and the solvent acetone can be separated and recovered, thereby realizing the recycling of the solvent acetone.
(6) High-efficiency equipment such as a high-efficiency gas-liquid dispersion mixing reactor, reduced-pressure flash evaporation equipment and the like is adopted, and rapid heat and mass transfer is realized.
The unit operation processes of the invention are all sealed circulation systems, the whole process is safe and environment-friendly, meets the requirements of clean production and the concept of green chemical industry, and is a green new method suitable for continuously producing sodium salicylate.
Detailed Description
The present invention will be described in further detail with reference to examples.
Example one
A method for preparing sodium salicylate by carboxylation reaction of sodium phenate, which takes acetone as a solvent, sodium phenate and carbon dioxide as raw materials, adopts an efficient gas-liquid dispersion mixing reactor, and the sodium phenate and the carbon dioxide undergo gas-liquid phase carboxylation reaction to obtain the sodium salicylate, and comprises the following steps:
(1) solution preparation: dissolving sodium phenolate in acetone in a stirring kettle to prepare a sodium phenolate solution, wherein the volume ratio of the mass of the sodium phenolate in the solution to the volume of the acetone is 1.0kg: 4.0L;
(2) and (3) carboxylation reaction: in a static mixer, carrying out gas-liquid dispersion mixing on sodium phenolate solution and carbon dioxide, wherein the molar ratio of sodium phenolate to carbon dioxide is 1.0:2.0, the reaction pressure is 0.8MPa, the sodium phenolate and the carbon dioxide are subjected to carboxylation reaction at the reaction temperature of 120 ℃ to generate sodium salicylate, and the reacted materials enter the next step;
(3) decompression flash evaporation: in a flash tank, performing reduced pressure flash evaporation operation on the material subjected to the carboxylation reaction in the previous step, wherein the absolute pressure of the operation is 0.08MPa, condensing and performing gas-liquid separation on a gas-phase material obtained by reduced pressure flash evaporation to obtain acetone and carbon dioxide for recycling, and allowing other materials to enter the next step;
(4) gas-solid separation: and (3) in a gas-solid separation device, carrying out gas-solid separation on the material obtained in the last step, wherein the solid-phase material is the sodium salicylate.
Example two
A method for preparing sodium salicylate by carboxylation reaction of sodium phenate, which takes acetone as a solvent, sodium phenate and carbon dioxide as raw materials, adopts an efficient gas-liquid dispersion mixing reactor, and the sodium phenate and the carbon dioxide undergo gas-liquid phase carboxylation reaction to obtain the sodium salicylate, and comprises the following steps:
(1) solution preparation: dissolving sodium phenolate in acetone in a stirring kettle to prepare a sodium phenolate solution, wherein the volume ratio of the mass of the sodium phenolate in the solution to the volume of the acetone is 1.0kg: 8.0L;
(2) and (3) carboxylation reaction: in a jet mixer, carrying out gas-liquid dispersion mixing on sodium phenolate solution and carbon dioxide, wherein the molar ratio of sodium phenolate to carbon dioxide is 1.0:1.6, the reaction pressure is 0.6MPa, the sodium phenolate and carbon dioxide are subjected to carboxylation reaction at the reaction temperature of 100 ℃ to generate sodium salicylate, and the reacted materials enter the next step;
(3) decompression flash evaporation: in a flash evaporation cooler, performing reduced pressure flash evaporation operation on the material subjected to the carboxylation reaction in the previous step, wherein the absolute pressure of the operation is 0.06MPa, condensing and performing gas-liquid separation on a gas-phase material obtained by reduced pressure flash evaporation to obtain acetone and carbon dioxide for recycling, and feeding other materials to the next step;
(4) gas-solid separation: and (3) in a gas-solid separation device, carrying out gas-solid separation on the material obtained in the last step, wherein the solid-phase material is the sodium salicylate.
EXAMPLE III
A method for preparing sodium salicylate by carboxylation reaction of sodium phenate, which takes acetone as a solvent, sodium phenate and carbon dioxide as raw materials, adopts an efficient gas-liquid dispersion mixing reactor, and the sodium phenate and the carbon dioxide undergo gas-liquid phase carboxylation reaction to obtain the sodium salicylate, and comprises the following steps:
(1) solution preparation: dissolving sodium phenolate in acetone in a stirring kettle to prepare a sodium phenolate solution, wherein the volume ratio of the mass of the sodium phenolate in the solution to the volume of the acetone is 1.0kg: 10.0L;
(2) and (3) carboxylation reaction: in a Venturi mixer, carrying out gas-liquid dispersion mixing on sodium phenolate solution and carbon dioxide, wherein the molar ratio of sodium phenolate to carbon dioxide is 1.0:2.0, the reaction pressure is 0.4MPa, the sodium phenolate and the carbon dioxide are subjected to carboxylation reaction at the reaction temperature of 80 ℃ to generate sodium salicylate, and the reacted materials enter the next step;
(3) decompression flash evaporation: in a flash tower, performing reduced pressure flash evaporation operation on the material subjected to the carboxylation reaction in the previous step, wherein the absolute pressure of the operation is 0.08MPa, condensing and performing gas-phase separation on the gas-phase material obtained by reduced pressure flash evaporation to obtain acetone and carbon dioxide for recycling, and allowing other materials to enter the next step;
(4) gas-solid separation: and (3) in a gas-solid separation device, carrying out gas-solid separation on the material obtained by the reduced pressure flash evaporation in the last step, wherein the solid-phase material is the sodium salicylate.
Besides the above examples, the present invention has many embodiments, and all the technical solutions using equivalent or equivalent substitution are within the protection scope of the present invention.
Claims (4)
1. A method for preparing sodium salicylate by carboxylation reaction of sodium phenate, which takes acetone as a solvent, sodium phenate and carbon dioxide as raw materials, adopts an efficient gas-liquid dispersion mixing reactor, and the sodium phenate and the carbon dioxide undergo gas-liquid phase carboxylation reaction to obtain the sodium salicylate, and is characterized by comprising the following steps:
(1) solution preparation: in sodium phenolate solution preparation equipment, dissolving sodium phenolate in an organic solvent acetone to prepare a sodium phenolate solution;
(2) and (3) carboxylation reaction: in a high-efficiency gas-liquid dispersion mixing reactor, carrying out gas-liquid dispersion mixing on sodium phenolate solution and carbon dioxide, carrying out carboxylation reaction on the sodium phenolate and the carbon dioxide to generate sodium salicylate, and feeding the reacted materials to the next step;
(3) decompression flash evaporation: in a decompression flash evaporation device, performing decompression flash evaporation operation on the material subjected to the carboxylation reaction in the previous step, condensing and performing gas-liquid separation on a gas-phase material obtained by decompression flash evaporation to obtain acetone and carbon dioxide for recycling, and allowing other materials to enter the next step;
(4) gas-solid separation: and (3) in a gas-solid separation device, carrying out gas-solid separation on the material obtained in the last step, wherein the solid-phase material is the sodium salicylate.
2. The method of claim 1, wherein the carboxylation reaction of sodium phenolate in acetone solution is carried out by: in the sodium phenolate solution prepared in the first step, the volume ratio of the mass of the sodium phenolate to the volume of the acetone is 1.0kg: 4.0L-1.0 kg: 10.0L.
3. The method of claim 1, wherein the carboxylation reaction of sodium phenolate in acetone solution to prepare sodium salicylate comprises: the efficient gas-liquid dispersion mixing equipment in the carboxylation reaction process of the sodium phenolate in the second step is any one of a static mixer, a jet mixer and a Venturi mixer, the molar ratio of the sodium phenolate to the carbon dioxide in the carboxylation reaction is 1.0: 1.2-1.0: 2.0, the reaction pressure is 0.4 MPa-0.8 MPa, and the reaction temperature is 80-120 ℃.
4. The method of claim 1, wherein the carboxylation reaction of sodium phenolate in acetone solution is carried out by: and the third step of decompression flash evaporation, wherein the equipment is any one of a flash tank, a flash cooler or a flash tower, and the absolute pressure of the operation is 0.02 MPa-0.08 MPa.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB949988A (en) * | 1960-06-17 | 1964-02-19 | Dow Chemical Co | Preparation of salcicylic acid and its alkali metal salts |
| CN107141215A (en) * | 2017-05-11 | 2017-09-08 | 镇江高鹏药业有限公司 | A kind of salicylic acid preparation method of environmental protection in high yield |
| CN110041189A (en) * | 2019-04-28 | 2019-07-23 | 东南大学 | It is a kind of to prepare salicylic technique using microchannel continuous flow reactor |
| CN112341335A (en) * | 2020-11-24 | 2021-02-09 | 江苏宏邦化工科技有限公司 | Synthesis method of methyl salicylate |
-
2022
- 2022-06-13 CN CN202210664795.0A patent/CN114874092A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB949988A (en) * | 1960-06-17 | 1964-02-19 | Dow Chemical Co | Preparation of salcicylic acid and its alkali metal salts |
| CN107141215A (en) * | 2017-05-11 | 2017-09-08 | 镇江高鹏药业有限公司 | A kind of salicylic acid preparation method of environmental protection in high yield |
| CN110041189A (en) * | 2019-04-28 | 2019-07-23 | 东南大学 | It is a kind of to prepare salicylic technique using microchannel continuous flow reactor |
| CN112341335A (en) * | 2020-11-24 | 2021-02-09 | 江苏宏邦化工科技有限公司 | Synthesis method of methyl salicylate |
Non-Patent Citations (1)
| Title |
|---|
| 郑穹 等: "《化学反应工程》", vol. 1, 兵器工业出版社, pages: 150 - 151 * |
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