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WO2018155069A1 - Procédé de production d'éther 1,2,2,2-tétrafluoroéthyl difluorométhyle (desflurane) - Google Patents

Procédé de production d'éther 1,2,2,2-tétrafluoroéthyl difluorométhyle (desflurane) Download PDF

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Publication number
WO2018155069A1
WO2018155069A1 PCT/JP2018/002377 JP2018002377W WO2018155069A1 WO 2018155069 A1 WO2018155069 A1 WO 2018155069A1 JP 2018002377 W JP2018002377 W JP 2018002377W WO 2018155069 A1 WO2018155069 A1 WO 2018155069A1
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Prior art keywords
reaction
desflurane
antimony
ether
formula
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PCT/JP2018/002377
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English (en)
Japanese (ja)
Inventor
健史 細井
峰男 渡辺
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Central Glass Co Ltd
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Central Glass Co Ltd
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/06—Halogens; Compounds thereof
    • B01J27/08—Halides
    • B01J27/10—Chlorides
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/06—Halogens; Compounds thereof
    • B01J27/08—Halides
    • B01J27/12—Fluorides
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/06—Halogens; Compounds thereof
    • B01J27/135—Halogens; Compounds thereof with titanium, zirconium, hafnium, germanium, tin or lead
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C07C41/22—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of halogens; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/04—Saturated ethers
    • C07C43/12—Saturated ethers containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B61/00—Other general methods

Definitions

  • 1,2,2,2-tetrafluoroethyl difluoromethyl ether is an important inhalation anesthetic known as desflurane.
  • the inhalation anesthetic has a very low in vivo metabolic rate and is widely used as a safe and gentle drug for the living body.
  • the present inventors have obtained very useful knowledge that, by adopting specific reaction conditions (reaction substrate, reaction reagent, catalyst), desflurane can be synthesized in an extremely small number of steps as compared with conventional production methods. Obtained.
  • the present inventors used fluoral (2,2,2-trifluoroacetaldehyde) or an equivalent thereof as a starting material when synthesizing desflurane, and by reacting chloroform and hydrogen fluoride in the presence of a catalyst, When examination which manufactures desflurane was performed, desflurane was not produced
  • chloral is reacted with chloroform and hydrogen fluoride in the presence of a Lewis acid catalyst to induce 2,2,2-trichloro-1-fluoroethyldifluoromethyl ether, followed by fluorination to produce desflurane.
  • a Lewis acid catalyst to induce 2,2,2-trichloro-1-fluoroethyldifluoromethyl ether, followed by fluorination to produce desflurane.
  • Second step Antimony, tantalum, niobium, molybdenum in the gas phase with respect to 1-fluoro-2,2,2-trichloroethyldifluoromethyl ether represented by the formula [2] obtained in the first step Represented by the formula [3] by reacting hydrogen fluoride in the presence of a metal halide-supported catalyst in which a metal halide containing at least one metal selected from the group consisting of tin, titanium and titanium is supported on activated carbon.
  • a metal halide-supported catalyst in which a metal halide containing at least one metal selected from the group consisting of tin, titanium and titanium is supported on activated carbon.
  • the Lewis acid catalyst used in the first step is boron (III), tin (II), tin (IV), titanium (IV), zinc (II), aluminum (III), antimony (III), and antimony (V).
  • the manufacturing method of the invention 1 which is a metal halide containing at least one metal selected from the group consisting of:
  • Invention 3 Invention 1 or the Lewis acid catalyst used in the first step is at least one metal halide selected from the group consisting of boron trifluoride (III), tin tetrachloride (IV), and antimony pentachloride (V) 2. The production method according to 2.
  • 1,2,2,2-tetrafluoroethyldifluoromethyl is obtained by using the easily described chloral as a starting material and passing through the steps described above using various reagents that are safe to handle.
  • the effect is that ether (desflurane) can be produced efficiently.
  • the method for producing 1,2,2,2-tetrafluoroethyldifluoromethyl ether (desflurane) of the present invention includes the following steps (from the first step to the second step).
  • Second step Antimony, tantalum, niobium, molybdenum in the gas phase with respect to 1-fluoro-2,2,2-trichloroethyldifluoromethyl ether represented by the formula [2] obtained in the first step Represented by the formula [3] by reacting hydrogen fluoride in the presence of a metal halide-supported catalyst in which a metal halide containing at least one metal selected from the group consisting of tin, titanium and titanium is supported on activated carbon.
  • a metal halide-supported catalyst in which a metal halide containing at least one metal selected from the group consisting of tin, titanium and titanium is supported on activated carbon.
  • the first step is a reaction represented by the formula [2] by reacting 2,2,2-trichloroacetaldehyde represented by the formula [1] with chloroform and hydrogen fluoride in the presence of a Lewis acid catalyst. This is a step of obtaining fluoro-2,2,2-trichloroethyl difluoromethyl ether.
  • the amount of chloroform used in this step is usually 1.0 equivalent or more with respect to chloral, and in order to allow the reaction to proceed smoothly, it is preferable to use 1.0 equivalent to 20.0 equivalent. In view of the treatment operation after the reaction, 1.0 equivalent to 3.0 equivalent is particularly preferable.
  • the Lewis acid catalyst used in this step is a metal halide containing at least one metal selected from the group consisting of boron, tin, titanium, zinc, aluminum, and antimony.
  • the metal halide to be used is preferably a high valence metal halide, that is, a metal halide having the highest possible valence.
  • a thermally or chemically stable solvent can be suitably used as the reaction solvent.
  • fluorous solvents such as perfluorobutane, perfluoropentane, perfluorohexane, and perfluoroheptane can be used. These reaction solvents can be used alone or in combination.
  • this step by using an excessive amount of chloroform as a reaction substrate, it can be used as a reaction reagent, and at the same time, it can be expected to function as a reaction solvent that facilitates the reaction.
  • side reaction such as temporary fluorination may occur in the reaction system of chloroform which is also a reaction substrate.
  • chlorofluoromethane (HCFC-21) or chlorodifluoromethane (HCFC-22) which are fluorinated products of chloroform, may be produced temporarily, the reaction with chloral proceeds and the purpose of this process is finally reached. Since it is thought that it converges to 2,2,2-trichloro-1-fluoroethyldifluoromethyl ether, which is a product, the side reaction of chloroform in this step is not particularly a problem.
  • this step it is possible to carry out the reaction without using a reaction solvent.
  • the temperature condition in this step may be performed in the range of +25 to + 200 ° C., usually +50 to + 180 ° C., and particularly preferably +100 to + 150 ° C.
  • the pressure condition in this step may be in the range of 0.1 MPa (absolute pressure, hereinafter the same in the present specification) to 10.0 MPa, usually 1.0 MPa to 7.0 MPa, particularly 1.0 MPa. 5.0 MPa is more preferable. Therefore, a pressure resistant reaction vessel made of a material such as stainless steel (SUS), a tetrafluoroethylene / perfluoroalkyl vinyl ether copolymer (PFA) or a polytetrafluoroethylene (PTFE) having anticorrosion performance against hydrogen fluoride, etc. A pressure-resistant reaction vessel lined with resin can be used.
  • SUS stainless steel
  • PFA tetrafluoroethylene / perfluoroalkyl vinyl ether copolymer
  • PTFE polytetrafluoroethylene
  • the reaction time in this step is usually within 48 hours, but depending on the reaction conditions due to the amount of chloral and hydrogen fluoride used, gas chromatography, thin layer chromatography, liquid chromatography, nuclear magnetics It is preferable that the progress of the reaction is traced by an analytical means such as resonance, and the point of time when the starting substrate has almost disappeared is the end point of the reaction.
  • the target 2,2,2-trichloro-1-fluoroethyldifluoromethyl ether of the formula [2] can be easily obtained by carrying out a normal purification operation on the reaction end solution. Obtainable.
  • the target product can be purified to a higher chemical purity product by activated carbon treatment, distillation, recrystallization, column chromatography and the like, if necessary.
  • This step is performed by using a reactor made of a material substantially inert to hydrogen fluoride and introducing chloral into the reaction zone filled with the catalyst under temperature control.
  • the reaction vessel used in this step is usually tubular and made of metal such as stainless steel, Hastelloy TM , platinum, tetrafluoroethylene resin, chloro-trifluoroethylene resin, vinylidene fluoride resin It is preferable to use a reaction vessel that is lined with a PFA resin or the like and can sufficiently react even under normal pressure or under pressure.
  • the metal halide used for catalyst preparation is preferably a high-valence metal halide, that is, a halide having the highest valence that can be usually obtained. Therefore, as the high valent metal in the halide, antimony (V: an oxidation number; the same applies hereinafter)), tin (IV), titanium (IV), niobium (V), tantalum (V), molybdenum (V ) Is preferred. Of these metals, antimony and tantalum are preferable, and antimony is particularly preferable.
  • Preparation method is not particularly limited as long as the metal halide adheres to the activated carbon.
  • a compound that is liquid near room temperature for example, antimony pentachloride, tin tetrachloride, or titanium tetrachloride
  • a treatment with a basic aqueous solution, acid or hot water described below, or a pretreatment for dehydration treatment was performed as necessary. It can be directly attached to the activated carbon by a method such as dropping, spraying or dipping.
  • the activated carbon is immersed in a solution in which the compound is dissolved in a solvent, or impregnated, or attached to the activated carbon by a method such as spraying.
  • the activated carbon attached with the metal compound thus obtained is dried by heating or / and reducing the pressure, and then the activated carbon attached with the metal halide is heated under hydrogen fluoride, chlorine, hydrogen chloride, fluoride chloride.
  • a catalyst is prepared by contacting with a hydrocarbon or the like. In particular, when antimony pentachloride is supported, treatment with 1 equivalent or more of chlorine at 100 ° C. or higher is desirable for activating the catalyst.
  • the solvent used in this step may be any solvent that can dissolve the metal halide and does not decompose the metal halide.
  • lower alcohols referred to as alcohols having a linear or branched alkyl group having 1 to 6 carbon atoms or alcohols having a cyclic alkyl group having 3 to 6 carbon atoms
  • Ethers referred to as alcohols having a linear or branched alkyl group having 1 to 6 carbon atoms or alcohols having a cyclic alkyl group having 3 to 6 carbon atoms
  • Ethers referred to as alcohols having a linear or branched alkyl group having 1 to 6 carbon atoms or alcohols having a cyclic alkyl group having 3 to 6 carbon atoms
  • ketones referred to as ketones, aromatic compounds, esters, chlorinated solvents, fluorinated solvents, and the like.
  • the amount of the metal halide used in the preparation of the catalyst used in this step on the activated carbon is 0.1 to 500 parts by mass, preferably 1 to 250 parts by mass with respect to 100 parts by mass of the activated carbon. .
  • catalyst activity can also be adjusted combining 2 or more types of metals.
  • antimony halide especially antimony pentachloride
  • other niobium compounds especially niobium pentachloride
  • tantalum compounds especially tantalum pentachloride
  • tin, titanium, niobium, tantalum, molybdenum halides It is good to combine.
  • the atomic ratio of the minor component metal / major component metal may not include the minor component metal, but may be 50/50 to 0/100, and preferably 30/70 to 0/100.
  • Activated carbon used as a carrier is plant based on wood, charcoal, coconut shell charcoal, palm kernel charcoal, bare ash, etc., coal based on peat, lignite, lignite, bituminous coal, anthracite, etc., petroleum residue, oil car
  • petroleum-based or synthetic resin-based such as carbonized polyvinylidene chloride using Bonn as a raw material.
  • activated carbon manufactured from bituminous coal BPL granular activated carbon manufactured by Toyo Calgon
  • coconut shell charcoal granular white birch GX, SX, CX, XRC manufactured by Takeda Pharmaceutical Co., Ltd., Toyo Calgon
  • PCB PCB
  • the shape and size are usually used in a granular form, but may be adapted to a reactor such as a sphere, fiber, powder or honeycomb.
  • the catalyst used in this step is in contact with hydrogen fluoride and / or chlorine.
  • supplying chlorine, fluorinated chlorinated or chlorinated hydrocarbon into the reactor during the reaction is effective for extending the catalyst life, improving the reaction rate, and the reaction yield.
  • introduction of chlorine is preferable for improving and maintaining the catalytic activity, and it is desirable to bring about 0.1 to 10 mol with respect to 100 mol of 2,2,2-trichloro-1-fluoroethyldifluoromethyl ether as a raw material.
  • the fluorination reaction proceeds by circulating hydrogen fluoride in the gas phase.
  • the catalyst retention method can be any type such as fixed bed, fluidized bed, moving bed, etc. Although it does not matter, it is convenient and preferable to carry out on a fixed bed.
  • the molar ratio of 1-fluoro-2,2,2-trichloroethyldifluoromethyl ether: hydrogen fluoride supplied to the reaction zone can vary depending on the reaction temperature, but is from 1:50 to 1: 2. : 30 to 1: 4 is preferable, and 1:20 to 1: 5 is more preferable.
  • the hydrogen fluoride is in an excessive amount, the reduction of the organic matter throughput and the separation of the mixture of the unreacted hydrogen fluoride discharged from the reaction system and the product are hindered.
  • reaction conversion rate falls and the yield of a target object falls.
  • reaction pressure was purged to 0.1 MPa, and 200 g of ion exchanged water was added to the reaction solution while paying attention to heat generation to stop the reaction. Subsequently, after washing with water, separation of two layers was performed to obtain 99 g of a crude reaction product.
  • bis-1,4-trifluorobenzene was used as an internal standard, and the quantitative value of the target product by 19 F-NMR was calculated. As a result, 25.8 g of 1-fluoro-2,2 , 2-trichloroethyl difluoromethyl ether was confirmed to be contained. In this case, the quantitative yield of the target product was 35%.
  • Example 2 In a 50 ml stainless steel (SUS) autoclave reactor equipped with a pressure gauge, thermometer, PTFE stirrer, 5 g (33.9 mmol) of chloral, 13.6 g (680 mmol) of hydrogen fluoride, 8.1 g of chloroform ( 68.0 mmol), and 0.481 g (3.39 mmol) of boron trifluoride diethyl ether complex were weighed out. After raising the internal temperature to 150 ° C., the reaction pressure was controlled at around 4.0 MPa while purging the by-produced hydrogen chloride gas, and the reaction was continued for 12 hours. After completion of the reaction, the reaction pressure was purged to 0.1 MPa, and the reaction solution was sampled.
  • SUS stainless steel
  • Example 3 In a 50 ml stainless steel (SUS) autoclave reactor equipped with a pressure gauge, thermometer, PTFE stirrer, 5 g (33.9 mmol) of chloral, 13.6 g (680 mmol) of hydrogen fluoride, 8.1 g of chloroform ( 68.0 mmol), and 1.01 g (3.39 mmol) of antimony pentachloride were weighed out. After the temperature was raised to an internal temperature of 150 ° C., the reaction pressure was controlled at around 4.0 MPa while purging the by-produced hydrogen chloride gas, and the reaction was continued for 8 hours. After completion of the reaction, the reaction pressure was purged to 0.1 MPa, and the reaction solution was sampled.
  • SUS stainless steel
  • Example 4 A gas phase reactor (made of SUS316L, diameter 2.5 cm, length 40 cm) composed of a cylindrical reaction tube equipped with an electric furnace was filled with 50 mL of the catalyst prepared in the preparation example as a catalyst. While flowing chlorine gas at a flow rate of about 3 mL / min, the temperature of the reaction tube was raised to 120 ° C., and hydrogen fluoride was introduced at a rate of about 0.1 g / min over 1 hour. Next, 1-fluoro-2,2,2-trichloroethyl difluoromethyl ether (90.2 GC area%) as a raw material was started to be supplied to the reaction tube at a rate of about 0.1 g / min (contact time 15 seconds).
  • a gas phase reactor (made of SUS316L, diameter 2.5 cm, length 40 cm) composed of a cylindrical reaction tube equipped with an electric furnace was filled with 50 mL of aluminum fluoride (AlF 3 ) as a catalyst. While flowing nitrogen gas at a flow rate of about 10 mL / min, the temperature of the reaction tube was raised to 180 ° C., and hydrogen fluoride was introduced at a rate of about 0.1 g / min over 1 hour. Next, 1-fluoro-2,2,2-trichloroethyl difluoromethyl ether (90.2 GC%) as a raw material was started to be fed to the reaction tube at a rate of about 0.1 g / min (contact time 14 seconds).
  • AlF 3 aluminum fluoride
  • 1,2,2,2-tetrafluoroethyl difluoromethyl ether can be used as an inhalation anesthetic.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

L'invention concerne un procédé par lequel l'éther 1-fluoro-2,2,2-trichloroéthyl difluorométhyle, qui est utile en tant qu'intermédiaire pour la synthèse de desflurane, est commodément obtenu à l'aide de chloral peu coûteux en tant que matériau de départ et en réagissant avec du chloroforme et du fluorure d'hydrogène en présence d'un catalyseur de type acide de Lewis. L'éther 1-fluoro-2,2,2-trichloroéthyl difluorométhyle est ensuite dérivé du desflurane par réaction avec du fluorure d'hydrogène dans la phase gazeuse en présence d'un catalyseur d'halogénure métallique supporté dans lequel un halogénure métallique contenant au moins un métal choisi dans le groupe constitué par l'antimoine, le tantale, le niobium, le molybdène, l'étain et le titane est supporté sur du charbon actif. Le procédé de l'invention peut produire de manière efficace du desflurane par un procédé court.
PCT/JP2018/002377 2017-02-24 2018-01-26 Procédé de production d'éther 1,2,2,2-tétrafluoroéthyl difluorométhyle (desflurane) Ceased WO2018155069A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2017-033257 2017-02-24
JP2017033257A JP2018138527A (ja) 2017-02-24 2017-02-24 １，２，２，２−テトラフルオロエチルジフルオロメチルエーテル（デスフルラン）の製造方法

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WO2018155069A1 true WO2018155069A1 (fr) 2018-08-30

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CN115477570A (zh) * 2021-05-30 2022-12-16 山东新时代药业有限公司 一种地氟烷的合成方法

Citations (1)

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Publication number Priority date Publication date Assignee Title
CN105753638A (zh) * 2014-12-13 2016-07-13 西安近代化学研究所 2,3,3,3-四氟丙烯的合成方法

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105753638A (zh) * 2014-12-13 2016-07-13 西安近代化学研究所 2,3,3,3-四氟丙烯的合成方法

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
HUDLICKY, TOMAS ET AL.: "Practical preparation of potentially anesthetic fluorinated ethyl methyl ethers by means of bromine trifluoride and other methods", JOURNAL OF FLUORINE CHEMISTRY, vol. 102, 2000, pages 363 - 367, XP004193168 *
SIVARAMAKRISHNAN, HARIHARAN ET AL.: "The Preparation of Desflurane by the Vapor-Phase Fluorination of Isoflurane", ORGANIC PROCESS RESEARCH & DEVELOPMENT, vol. 15, no. 3, 15 March 2011 (2011-03-15), pages 585 - 592, XP055532327 *

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