WO2024198718A1 - Procédé de production en continu de chlorure de propionyle de haute pureté - Google Patents

Procédé de production en continu de chlorure de propionyle de haute pureté Download PDF

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Publication number
WO2024198718A1
WO2024198718A1 PCT/CN2024/075440 CN2024075440W WO2024198718A1 WO 2024198718 A1 WO2024198718 A1 WO 2024198718A1 CN 2024075440 W CN2024075440 W CN 2024075440W WO 2024198718 A1 WO2024198718 A1 WO 2024198718A1
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Prior art keywords
propionyl chloride
propionic acid
chloride
reaction
purity
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Chinese (zh)
Inventor
马海兵
安冉
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Yantai Tayho Advanced Materials Research Institute Co ltd
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Yantai Tayho Advanced Materials Research Institute Co ltd
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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
    • C07C51/58—Preparation of carboxylic acid halides
    • C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/58—Preparation of carboxylic acid halides
    • C07C51/64—Separation; Purification; Stabilisation; Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
    • C07C53/38—Acyl halides
    • C07C53/42—Acyl halides of acids containing three or more carbon atoms
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/584—Recycling of catalysts

Definitions

  • the invention belongs to the technical field of propionyl chloride production, and particularly relates to a continuous production method of high-purity propionyl chloride.
  • Propionyl chloride is an important organic synthesis intermediate, mainly used in the synthesis of fine chemicals such as medicines and pesticides.
  • a pharmaceutical intermediate propionyl chloride can produce naproxen, methyltoin, choleretic acid, etc.
  • As a pesticide intermediate it can produce the broad-spectrum herbicide propanil, and is used as a propionylating agent in organic synthesis.
  • the purity requirement for propionyl chloride is usually ⁇ 99%. Therefore, it is very necessary to develop an efficient, fast, environmentally friendly and low-cost method for producing propionyl chloride.
  • phosphorus trichloride method phosphorus trichloride method
  • phosgene method phosgene method
  • thionyl chloride method phosphorus trichloride method
  • phosphorus trichloride method and phosgene method are more common.
  • the Chinese patent application with publication number CN113999110A discloses: phosphorus trichloride and propionic acid are used to produce propionyl chloride by continuous method, but the raw materials are added in an intermittent method.
  • the yield of propionyl chloride is about 95% and the product purity is ⁇ 98%.
  • propionyl chloride is produced by phosphorus trichloride method
  • phosphorous acid is produced as a byproduct, causing environmental pollution.
  • propionyl chloride and phosphorous acid have similar boiling points and easily form an azeotropic mixture, propionyl chloride is not easy to be separated during the distillation process, which reduces the product quality and cannot be used as a pharmaceutical and pesticide intermediate.
  • Zhou Xiaoqian et al. introduced a process for synthesizing propionyl chloride using propionic acid and phosgene as raw materials under the action of a catalyst in the article "Research on the Synthesis of Propionyl Chloride by Phosgene Method" (Liaoning Chemical Industry, 2003, 32 (1): 9-11). This method is semi-continuous production with a yield of 99% and a product purity of ⁇ 98%.
  • the purity of the product obtained by the phosphorus trichloride method and the phosgene method is about 98%, which cannot meet the market's quality demand for high-purity propionyl chloride.
  • the phosgene method and the phosphorus trichloride method have certain shortcomings due to factors such as danger or limited production capacity.
  • thionyl chloride is a relatively safe chlorination agent.
  • the product is mainly gas, which can be separated from the system, which is conducive to the separation of the product.
  • thionyl chloride method is used to produce acyl chloride products, thionyl chloride is usually used as an excess raw material during the reaction. Therefore, if propionyl chloride is produced by the thionyl chloride method, thionyl chloride will exist in the propionyl chloride product because the boiling points of thionyl chloride and propionyl chloride are very close, resulting in reduced product quality.
  • the purpose of the present invention is to provide a continuous production method for high-purity propionyl chloride, which solves the technical problems that when the prior art adopts the thionyl chloride method to prepare propionyl chloride, the product is not easy to separate, resulting in low purity, low yield and a large amount of by-products that are harmful to the environment.
  • the present invention adopts the following technical solutions to achieve
  • the invention discloses a continuous production method of high-purity propionyl chloride, comprising the following steps:
  • the molar ratio of propionic acid to thionyl chloride is (1.05-1.5):1.
  • the added amount of ferric propionate is 0.4% to 1.6% of the mass of thionyl chloride.
  • step 2) the mixed solution undergoes three-stage reaction, the first-stage reaction temperature is -13 ⁇ 8°C, the second-stage reaction temperature is 8 ⁇ 26°C, and the third-stage reaction temperature is 26 ⁇ 45°C.
  • step 2) several stages of reaction are adjusted according to the reaction degree of thionyl chloride.
  • the number of reactor stages is reduced; when the reaction speed is slow and the thionyl chloride reacts incompletely, the number of reactor stages is increased.
  • the purification process adopts a continuous distillation method, including a primary distillation and a secondary distillation:
  • the crude propionyl chloride is heated to 82-91°C to vaporize the propionyl chloride, and then cooled and collected to obtain the finished propionyl chloride, as well as propionic acid and high-boiling substances;
  • the extraction temperature of the vaporized propionyl chloride is maintained at 77-81° C., and then the finished propionyl chloride is collected after being cooled to 25-35° C. through a condenser.
  • the extraction temperature of the vaporized propionic acid is maintained at 139-142° C., and then the finished propionic acid product is collected after being cooled to 30-40° C. through a condenser.
  • the number of the storage tanks is at least two, one storage tank is used as a receiving tank for crude propionyl chloride to ensure that the unreacted materials caused by abnormal feeding in the previous stages of reaction are fully reacted in the storage tank, and the other storage tank is used as a storage tank for the distillation process.
  • the number of the multi-stage distillation towers is at least two, thereby ensuring the purity of the prepared propionyl chloride.
  • the present invention has the following beneficial effects: the continuous production method of high-purity propionyl chloride disclosed in the present invention uses thionyl chloride and excess propionic acid as raw materials and ferric propionate as a reaction catalyst, and the obtained product propionyl chloride is easy to separate and purify due to the large boiling point difference with the excess propionic acid, and due to the catalytic effect of the trivalent iron ion in the reaction catalyst ferric propionate and the common ion effect of the propionate ion, the chlorination reaction of thionyl chloride and propionic acid is promoted more quickly, so that the present invention has the advantages of high purity and high yield of propionyl chloride.
  • the high-purity propionyl chloride prepared by this method can be used for the production of pesticides and medicines, and the unreacted propionic acid is recovered and transported to the reaction end for continuous reaction, so that the raw materials can be reused, thereby saving production costs.
  • Fig. 1 is a schematic diagram of the structure of a multi-stage reactor system capable of realizing the continuous production method of high-purity propionyl chloride of the present invention
  • V5-dosing tank R1-primary reactor; R2-secondary reactor; R3-tertiary reactor; V1-first storage tank; V2-second storage tank; V3-propionyl chloride finished product storage tank; V4-propionic acid finished product storage tank; T1-primary distillation tower; T2-secondary distillation tower.
  • a multistage reaction system capable of continuously producing high-purity propionyl chloride is constructed to realize the continuous production method of high-purity propionyl chloride of the present invention, comprising:
  • Batching tank V5 used to mix reaction raw materials and catalyst
  • a multi-stage reactor for performing several-stage reactions the following embodiments all take a three-stage reactor as an example, including a primary reactor R1, a secondary reactor R2 and a tertiary reactor R3;
  • the following embodiment includes two storage tanks connected in series, namely a first storage tank V1 and a second storage tank V2;
  • a multi-stage distillation tower for purifying crude propionyl chloride wherein the following embodiments all take a two-stage distillation tower as an example, namely a primary distillation tower T1 and a secondary distillation tower T2;
  • Finished product storage tanks including propionyl chloride finished product storage tank V3 and propionic acid finished product storage tank V4.
  • Thermometers are provided on the primary reactor R1, the secondary reactor R2, the tertiary reactor R3, the first storage tank V1, the second storage tank V2, and the primary distillation tower T1 and the secondary distillation tower T2 to monitor the temperature.
  • the number of stages of the reaction can be adjusted according to the reaction degree of thionyl chloride.
  • the reaction speed is fast, thionyl chloride can react completely, and the number of reactors can be reduced; when the reaction speed is slow, thionyl chloride does not react completely, and the number of reactors can be increased to ensure that thionyl chloride reacts completely.
  • a condenser is provided above each stage of the reactor, and a refrigerant is introduced into the condenser, and the temperature of the refrigerant is 5-8°C to prevent the volatilization loss of thionyl chloride or the product propionyl chloride.
  • the cooled thionyl chloride can be refluxed to the corresponding reactor, and the cooled propionyl chloride can be refluxed to the corresponding storage tank.
  • the uncooled byproducts hydrogen chloride and sulfur dioxide gas are absorbed by water and sodium hydroxide, respectively, to form byproducts hydrochloric acid and sodium bisulfite or sodium sulfite.
  • reaction catalyst iron propionate used in the present invention is prepared using iron hydroxide and propionic acid as raw materials, and the reaction equation is as follows:
  • the specific preparation process is: solid ferric hydroxide and propionic acid are mixed in a molar ratio of 1:8, heated under reflux for 5 hours, filtered to remove a small amount of unreacted ferric hydroxide solid, and then the filtrate is decompressed to remove water and propionic acid to obtain ferric propionate with a purity of 98%, which can be directly used as the reaction catalyst of the present invention.
  • ferric hydroxide can also be directly added to the mixture of propionic acid and thionyl chloride in an equal amount of trivalent iron to carry out a catalytic reaction.
  • a continuous production method for high-purity propionyl chloride comprises the following steps:
  • the prepared mixed solution is transported to the bottom inlet of the primary reactor R1 through a pipeline at a rate of 444 kg/h, and the temperature of the primary reactor R1 is maintained at -13 °C.
  • the reaction solution after the reaction in the primary reactor R1 flows out from the upper overflow port of the primary reactor R1 and is transported to the bottom inlet of the secondary reactor R2 through a pipeline, and the temperature of the secondary reactor R2 is maintained at 8 °C.
  • the reaction solution after the reaction in the secondary reactor R2 flows out from the upper overflow port of the secondary reactor R2 and is transported to the bottom inlet of the tertiary reactor R3 through a pipeline, and the temperature of the tertiary reactor R3 is maintained at 26 °C.
  • the crude propionyl chloride after the reaction in the tertiary reactor R3 flows out from the upper overflow port of the tertiary reactor R3 and is transported to the bottom inlet of the first storage tank V1 through a pipeline, and the temperature of the first storage tank V1 is maintained at 45 °C.
  • the crude propionyl chloride in the first storage tank V1 flows out from the upper overflow port of the first storage tank V1 and is transported to the bottom inlet of the second storage tank V2 through a pipeline, and the temperature of the second storage tank V2 is maintained at 45 °C, the liquid in the second storage tank V2 is used as the raw liquid for the distillation section; the storage temperature of the crude propionyl chloride not only ensures the further reaction of the unreacted reaction liquid in storage, but also ensures the heat required for subsequent distillation and purification.
  • the propionic acid and high-boiling substances at the bottom of the primary distillation tower T1 are continuously transported to the middle section of the secondary distillation tower T2 by a pump, heated to 153°C by a distillation tower reboiler, and propionic acid is vaporized to the top of the secondary distillation tower T2 for extraction, cooled to 30°C by a condenser, and the finished propionic acid is collected and stored in the finished propionic acid storage tank V4 as a synthetic raw material (transported back to the batching tank V5 through a pipeline) for reuse.
  • the high-boiling substances at the bottom of the secondary distillation tower T2 are continuously extracted by a pump as distillation residues; the top extraction temperature of the primary distillation tower T1 is maintained at 77 °C, and the top extraction temperature of the secondary distillation tower T2 is maintained at 139 °C.
  • a continuous production method for high-purity propionyl chloride comprises the following steps:
  • the prepared mixed solution is transported to the bottom inlet of the primary reactor R1 through a pipeline at a rate of 470.68 kg/h, and the temperature of the primary reactor R1 is maintained at 0 °C.
  • the reaction liquid after the reaction in the primary reactor R1 flows out from the upper overflow port of the primary reactor R1 and is transported to the bottom inlet of the secondary reactor R2 through a pipeline, and the temperature of the secondary reactor R2 is maintained at 17 °C.
  • the reaction liquid after the reaction in the secondary reactor R2 flows out from the upper overflow port of the secondary reactor R2 and is transported to the bottom inlet of the tertiary reactor R3 through a pipeline, and the temperature of the tertiary reactor R3 is maintained at 33 °C.
  • the crude propionyl chloride after the reaction in the tertiary reactor R3 flows out from the upper overflow port of the tertiary reactor R3 and is transported to the bottom inlet of the first storage tank V1 through a pipeline, and the temperature of the first storage tank V1 is maintained at 50 °C.
  • the crude propionyl chloride in the first storage tank V1 flows out from the upper overflow port of the first storage tank V1 and is transported to the bottom inlet of the second storage tank V2 through a pipeline, and the temperature of the second storage tank V2 is maintained at 50 °C, the liquid in the second storage tank V2 is used as the raw liquid for the distillation section;
  • the propionic acid and high-boiling substances at the bottom of the primary distillation tower T1 are continuously transported to the middle section of the secondary distillation tower T2 by a pump, heated to 155°C by a distillation tower reboiler, and propionic acid is vaporized to the top of the secondary distillation tower T2 for extraction, cooled to 35°C by a condenser, and the finished propionic acid is collected and stored in the finished propionic acid storage tank V4 as a synthetic raw material (transported back to the batching tank V5 through a pipeline) for reuse.
  • the high-boiling substances at the bottom of the secondary distillation tower T2 are continuously extracted by a pump as distillation residues; the extraction temperature of the top of the primary distillation tower T1 is maintained at 79 °C, and the top extraction temperature of the secondary distillation tower T2 is maintained at 140 °C.
  • a continuous production method for high-purity propionyl chloride comprises the following steps:
  • the prepared mixed solution is transported to the bottom inlet of the primary reactor R1 through a pipeline at a rate of 522.2 kg/h, and the temperature of the primary reactor R1 is maintained at 8°C.
  • the reaction solution after the reaction in the primary reactor R1 flows out from the upper overflow port of the primary reactor R1 and is transported to the bottom inlet of the secondary reactor R2 through a pipeline, and the temperature of the secondary reactor R2 is maintained at 26°C.
  • the reaction solution after the reaction in the secondary reactor R2 flows out from the upper overflow port of the secondary reactor R2 and is transported to the bottom inlet of the tertiary reactor R3 through a pipeline, and the temperature of the tertiary reactor R3 is maintained at 45°C.
  • the crude propionyl chloride after the reaction in the tertiary reactor R3 flows out from the upper overflow port of the tertiary reactor R3 and is transported to the bottom inlet of the first storage tank V1 through a pipeline, and the temperature of the first storage tank V1 is maintained at 60°C.
  • the crude propionyl chloride in the first storage tank V1 flows out from the upper overflow port of the first storage tank V1 and is transported to the bottom inlet of the second storage tank V2 through a pipeline, and the temperature of the second storage tank V2 is maintained at 60°C. °C, the liquid in the second storage tank V2 is used as the raw liquid for the distillation section;
  • the propionic acid and high-boiling substances at the bottom of the primary distillation tower T1 are continuously transported to the middle section of the secondary distillation tower T2 by a pump, heated to 153°C by a distillation tower reboiler, and propionic acid is vaporized to the top of the secondary distillation tower T2 for extraction, cooled to 40°C by a condenser, and the finished propionic acid is collected and stored in the finished propionic acid storage tank V4 as a synthetic raw material (transported back to the batching tank V5 through a pipeline) for reuse.
  • the high-boiling substances at the bottom of the secondary distillation tower T2 are continuously extracted by a pump as distillation residue; the extraction temperature of the top of the primary distillation tower T1 is maintained at 81 °C, and the top extraction temperature of the secondary distillation tower T2 is maintained at 142 °C.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un procédé de production en continu de chlorure de propionyle de haute pureté, qui appartient au domaine technique de la production de chlorure de propionyle. Le procédé résout les problèmes techniques de faible pureté et de faible rendement provoqués par la difficulté de séparation de produits et de dommages à l'environnement provoqués par un grand nombre de sous-produits dans l'état de la technique où le chlorure de propionyle est préparé au moyen d'un procédé de chlorure de thionyle. Dans le procédé, du chlorure de thionyle et un excès d'acide propionique sont utilisés en tant que matières premières, du propionate ferrique est utilisé en tant que catalyseur de réaction, et le produit préparé, c'est-à-dire le chlorure de propionyle, est facile à séparer et à purifier grâce à son point d'ébullition considérablement différent de celui d'un excès de l'acide propionique. Le chlorure de propionyle de haute pureté préparé à l'aide du procédé peut être utilisé dans la production de pesticides et de médicaments, et l'acide propionique n'ayant pas réagi est récupéré et transporté vers une extrémité de réaction pour une réaction en continu, de telle sorte que les matières premières peuvent être recyclées, ce qui permet d'économiser sur le coût de production.
PCT/CN2024/075440 2023-03-27 2024-02-02 Procédé de production en continu de chlorure de propionyle de haute pureté Ceased WO2024198718A1 (fr)

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CN202310300734.0 2023-03-27
CN202310300734.0A CN116023257B (zh) 2023-03-27 2023-03-27 一种高纯度丙酰氯的连续生产方法

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CN116023257B (zh) * 2023-03-27 2023-07-25 烟台泰和新材高分子新材料研究院有限公司 一种高纯度丙酰氯的连续生产方法
CN117720069B (zh) * 2023-12-13 2025-10-31 烟台泰和新材高分子新材料研究院有限公司 一种生产酰氯副产品盐酸的连续纯化方法及生产设备
CN119143598B (zh) * 2024-11-15 2025-03-11 烟台泰和新材高分子新材料研究院有限公司 一种高纯度酰氯类产品的制备方法
CN119390563A (zh) * 2025-01-02 2025-02-07 新华制药（寿光）有限公司 一种丙酰氯的连续化合成工艺

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