WO2006030656A1 - Procédé servant à purifier du chlorure d'éthyle et procédé servant à produire du fluoroéthane en utilisant celui-ci - Google Patents

Procédé servant à purifier du chlorure d'éthyle et procédé servant à produire du fluoroéthane en utilisant celui-ci Download PDF

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Publication number
WO2006030656A1
WO2006030656A1 PCT/JP2005/016155 JP2005016155W WO2006030656A1 WO 2006030656 A1 WO2006030656 A1 WO 2006030656A1 JP 2005016155 W JP2005016155 W JP 2005016155W WO 2006030656 A1 WO2006030656 A1 WO 2006030656A1
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WO
WIPO (PCT)
Prior art keywords
stabilizer
chloride
ethyl chloride
chlorinated
chill
Prior art date
Application number
PCT/JP2005/016155
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English (en)
Japanese (ja)
Inventor
Hiromoto Ohno
Yukio Nishiyama
Original Assignee
Showa Denko K.K.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Showa Denko K.K. filed Critical Showa Denko K.K.
Priority to JP2006535726A priority Critical patent/JP4953819B2/ja
Publication of WO2006030656A1 publication Critical patent/WO2006030656A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/38—Separation; Purification; Stabilisation; Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B63/00—Purification; Separation; Stabilisation; Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
    • C07C17/202—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction
    • C07C17/206—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction the other compound being HX
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/38—Separation; Purification; Stabilisation; Use of additives
    • C07C17/389—Separation; Purification; Stabilisation; Use of additives by adsorption on solids

Definitions

  • the present invention relates to a method for purifying chlorinated chlor and a fluorochemical using the method.
  • the present invention relates to a method for producing ethane.
  • Examples of methods for producing ethyl chloride include (1) a method in which hydrogen chloride is blown into a mixture of ethyl alcohol and zinc chloride when heated, and (2) a method in which aluminum chloride is used as a catalyst. Methods for adding chlorine to water .. Elementary chemicals (Chemical Dictionary 1 (Kyoritsu Shuppan)) are known.
  • a stabilizer is generally added, and a stabilizer of about several hundred mass ppm is added.
  • chloro chloride is hydrolyzed by moisture and alcohol.
  • fluoroeluene (CH 3 CH 2 F) produced using chlorinated chill as a raw material is attracting attention as a low-temperature refrigerant, for example, as an etching gas.
  • Chlorofluorocarbons CFCs
  • Hydrok ⁇ ⁇ Saturated and unsaturated compounds such as Fluorocarbons (HCFCs) are produced, and separation and purification are extremely difficult. .
  • the above method (2) uses flammable and explosive range ethylene as a raw material, so that the equipment cost for ensuring safety is large and has an economic problem.
  • the method of reacting chloro chloride and hydrogen fluoride as raw materials in the presence of a fluorination catalyst is, for example, when a catalyst mainly composed of trivalent dimethyl oxide is used. Acetylene and ethylene are produced by reactions, etc., and there are problems in safety and economics, leaving technical issues.
  • ethyl chloride which is one of the reaction raw materials, contains a stabilizer to suppress the generation of acid content.
  • stabilizers compounds having a single-mouth group include, for example, nitromethane, nitroen, cresol, nitrotoluene, and two-hole fenol.
  • stabilizers and moisture contained in ethyl chloride are undesirable because, for example, they cause deterioration in the activity of the fluorination catalyst used in the production of fluorethan and shorten the catalyst life. It is desirable not to be included.
  • the stabilizer may be removed before the reaction.
  • the conventional removal method such as fractional distillation has a problem that the operation is complicated and a large amount of cost is required.
  • the present invention has been made under such a background, and it is possible to remove stabilizers and moisture contained in chlorinated chill, which is easy to operate and industrially feasible. It is an object of the present invention to provide a purification method and a method for producing fluoroethane using the chlorinated chill obtained by this purification method.
  • a crude chlorinated chill containing a stabilizer and water or moisture has a mean pore diameter in the range of 3 to 11 A and / or a mean pore diameter. It has been found that the stabilizer and / or water content can be reduced by contacting in a liquid phase with a carbonaceous adsorbent having a range of 3.4 to 11 A.
  • the economy has advantages such as efficient and long catalyst life.
  • the present inventors have found that a typical method for producing fluoretane can be obtained, and have completed the present invention.
  • this invention consists of a matter shown by the following [1]-[14], for example.
  • a method for purifying chlorinated chloride which is characterized by bringing the carbonaceous adsorbent into contact with a liquid phase and reducing the stabilizer and / or moisture contained in the crude ethyl chloride.
  • the pressure at which the stabilizer and / or crude chlorinated chill containing water is brought into contact with the zeolite and / or the carbonaceous adsorbent is in the range of 0 to IMP a.
  • a stabilizer obtained by the purification method according to any one of the above [1] to [7] and Z or chilled chilled chloride with reduced moisture are used as raw materials.
  • step (2) is performed using chlorinated chill reduced to 20 mass pPm or less.
  • the fluorination catalyst used in the step (2) is Cu, M n
  • the fluorination catalyst used in the step (2) is a supported catalyst supported on activated carbon, according to any one of the above [9] to [13] Fluoroe evening production method.
  • the present invention it is possible to efficiently remove a stabilizer and moisture from a stabilizer and / or water-containing chlorinated chloride by a simple method, prevent deterioration of the catalyst, etc., and economically produce fluoretane.
  • the obtained fluorethan can be used as a low temperature refrigerant or etching gas.
  • the present inventor obtained an average of chlorinated chills containing stabilizers.
  • the amount of stabilizer can be reduced by contacting the zeolite with a pore size of 3 to 11 A and / or a carbonaceous adsorbent with an average pore size of 3.4 to 11 A in the liquid phase. I found out that I can do it.
  • the zeolite used in the method for purifying chlorinated chloride according to the present invention should have an average pore diameter of 3 to 11 A, preferably 3.4 to 10 A. Zeolite ⁇ with an average pore size greater than 11 A increases the adsorption amount of chlorinated chloride, and zeolite with an average pore size less than 3 A has a smaller ability to adsorb stabilizers. Yes.
  • the zeolite has a Si (silica) A 1 (aluminum) ratio of 2 or less, and when the S i ZA l ratio is greater than 2, the stabilizer may not be selectively adsorbed.
  • Zeolites include molecular sieves 4 A (MS—4 A), molecular sieves 5 A (MS—5 A), molecular sieves 1 OA (MS— 1 OA) and molecular sieves 1 3 X (S-1 3 X) is preferably at least one selected from the group consisting of
  • the water content in ethyl chloride can be reduced at the same time. When heated while containing water, hydrolysis occurs, so it is preferable to reduce the water content.
  • the water content in ethyl chloride is preferably 20 mass ppm or less.
  • Carbonaceous adsorbents preferably have an average pore diameter of 3.4 to 11 A, and carbonaceous adsorbents with an average pore diameter greater than 11 A increase the amount of adsorption of chlorinated chloro chloride.
  • a carbonaceous adsorbent with a pore size smaller than 3.4 A is not preferred because it reduces the ability to adsorb stabilizers.
  • molecular sieve force 1 Bon 4 A and Z or molecular sieve carbon 5 A is preferable.
  • the zeolite and the carbonaceous adsorbent are not particularly limited, but considering that the moisture in the ethyl chloride is also reduced, the mixing ratio is preferably a ratio rich in zeolite.
  • the adsorbent is preferably distributed continuously on a fixed bed, and the liquid-based space velocity (LHSV) Can be selected appropriately depending on the stabilizer concentration and the amount of chlorinated chill.
  • LHSV liquid-based space velocity
  • the range of 1 to 80 H r -1 is preferable.
  • two adsorption towers may be provided, and two towers may be switched to perform continuous purification.
  • the treatment temperature when purifying chloro chloride in the liquid phase is preferably in the range of 120 to + 60 ° C, more preferably in the range of 0 to 50 ° C. If the treatment temperature is higher than 60 ° C, the equipment cost may increase in terms of the heating and pressure resistance of the equipment, decomposition reactions, etc. may occur. This is not preferable.
  • the pressure is preferably in the range of 0 to I M Pa, more preferably in the range of 0 to 0.6 M Pa. When the pressure is greater than 1 M Pa, it is not economical in terms of the pressure resistance of the equipment.
  • the stabilizer and Z or moisture contained in the ethyl chloride can be reduced.
  • the purification method of the present invention is particularly preferably used when the stabilizer is a compound having a nitro group or a hydroxyl group, and examples of the compound having a nitro group include nitromethane, nitrogen, and nitrogen. Examples thereof include resole, nitrotoluene and nitrophenol. Examples of the compound having a hydroxyl group include phenol, cresol, 2,6-dibutyl-p-cresol and aminomethylphenol.
  • the chlorinated chill containing a stabilizer is brought into contact with the above zeolite and / or the above carbonaceous adsorbent in the liquid phase under the above conditions, and the total amount of the stabilizer is reduced to 20 mass ppm or less. You can get a chill.
  • the salt is reduced to 10 mass ppm or less in the total amount of the stabilizer, and further reduced to 5 ppm or less in the total amount of the stabilizer. It is also possible to obtain a chemical ester.
  • the method for producing fluoretane of the present invention comprises the following three steps:
  • the ethyl chloride obtained through the step (1) is preferably a chloride chill in which the total amount of the compound having a nitro group or a hydroxyl group is reduced to 20 mass ppm or less, and more preferably The total amount of the compound having a nitro group or a hydroxyl group is preferably reduced to 10 mass ppm or less, and particularly preferably the total amount of the compound having a nitro group or a hydroxyl group is reduced to 5 mass ppm or less. Good to have. Producing fluoretane from chlorinated chills with the total amount of compounds having a nitro group and a hydroxyl group reduced to 20 mass ppm or less can increase the life of the catalyst used in the production process and increase efficiency. It is possible to produce a mixture mainly containing fluoretane, both economically and economically.
  • the catalyst used in the manufacturing process is at least selected from the group consisting of Cu, Mn, Zn, Pb, Ag, Bi, Co, Fe, Ni and the same.
  • Fluorination catalysts containing one element which are preferably supported catalysts or bulk catalysts, for example generally halogen exchange reactions
  • the main component is lumped chromic oxide, which is the catalyst used for this purpose.
  • a type catalyst or a supported catalyst for example, one using alumina, aluminum fluoride, etc. as a carrier
  • acetylene or ethylene is produced by the dehalogenation reaction or dehydrogenation reaction as described above.
  • the metal loading is preferably 1% by mass or more.
  • activated carbon is impregnated with an aqueous solution of cobalt chloride, dried, heat-treated in an inert gas, and then reacted. It is preferable to activate with hydrogen fluoride before carrying out.
  • the reaction temperature is preferably from 100 to 350 ° C, more preferably from 150 to 300 ° C. When the reaction temperature is higher than 350 ° C, the amount of acetylene or the like that is a by-product may increase, and when it is lower than 100 ° C, the target reaction may not proceed.
  • the reaction pressure is preferably 0 to 1 MPa, and if it exceeds IMP a, equipment costs such as the pressure resistance of the apparatus increase, which is not economical.
  • the molar ratio of hydrogen fluoride to acetyl chloride is preferably 3 to 20; if it exceeds 20, it is not economical due to the increased amount of hydrogen fluoride. It is not economical because its life is short.
  • the mixture containing fluorethane obtained in the above reaction step is led to a distillation purification step, and at least 90% or more of hydrogen chloride and fluorethane are separated from the top of the column as a low boiling fraction in the distillation purification step. At least 95% of the unreacted hydrogen fluoride and acetyl chloride are separated from the bottom as a high boiling fraction. Hydrogen chloride and fluoretane separated from the top of the column are separated in a separate distillation tower, hydrogen chloride is used for other purposes, and the target fluoretane is purified and recovered as a product.
  • a commercially available chlorinated chill was analyzed with a gas chromatograph (column: complete set of pills / FID).
  • nitrogen (CH 3 N 0 2 ) contained 2 1 2 mass ppm, and a moisture meter The moisture content was analyzed by Sha type 1) and found to contain 52 mass ppm, and the purity of the salt chill was 99.95 mass%.
  • Activated carbon (Kuraray Chemical Co., Ltd., Kuraray Call 4 GA) is used as the catalyst carrier.
  • Ferric chloride (FeCl 3 '6 H 2 0) 3 2. Add 58.5 g of pure water to 7 g and heat to 50-60 ° C in a hot water bath to dissolve The solution was cooled to room temperature. To this, 57.977 g of the activated carbon that had been vacuum-dried at 120 ° C. for 3 hours as a pretreatment was crushed to absorb the entire amount of the solution. The wet activated carbon was then dried on a hot water bath at 90 and dried. Thereafter, the dried catalyst was dried in a dryer at 100 ° C. for 3 hours. Next, the catalyst was charged into an Inconel reactor, and the temperature was maintained at 230 ° C. while flowing nitrogen gas, and diluted with nitrogen. The catalyst was prepared by fluorination treatment (activation of the catalyst) under a hydrogen fluoride (HF) stream and then under a 100% hydrogen fluoride stream.
  • HF hydrogen fluoride
  • Activated carbon (Kuraray Chemical Co., Ltd., Kuraray Call 4 GA) is used as the catalyst carrier.
  • nitromethane which is a stabilizer in ethyl chloride, was reduced to 2 mass ppm, and the water content was 2 mass ppm or less.
  • a carbonaceous adsorbent [ 20 g of molecular sieve carbon 5 A (manufactured by Takeda Pharmaceutical Co., Ltd .: average pore diameter 5 A)] is filled, vacuum dried, and the chilled chill shown in raw material example 2 is cooled while cooling the cylinder. 80 g was charged and stirred occasionally while maintaining the temperature at 23 ° C. (room temperature). After about 5 hours, a part of the liquid phase was taken and analyzed by gas chromatography.
  • Example 2 The same operation and conditions as in Example 2 except that 20 g of carbonaceous adsorbent [activated carbon: granular white sword KL (manufactured by Takeda Pharmaceutical Co., Ltd .: average pore diameter 3 5 A)] was used as the adsorbent. Processed and analyzed.
  • carbonaceous adsorbent activated carbon: granular white sword KL (manufactured by Takeda Pharmaceutical Co., Ltd .: average pore diameter 3 5 A)
  • cresol a stabilizer in ethyl chloride
  • Example 5 The reaction was carried out under the same procedures and conditions as in Example 5 except that 80 ml of the catalyst shown in Catalyst Example 2 was charged as the catalyst. After the reaction started, the outlet gas was washed with an alkaline aqueous solution about 5 hours later. Analyzed by totography. The results are shown below.
  • Inconel 60 inch reactor with inner diameter 1 inch and length lm is filled with 60 ml of the catalyst shown in Catalyst Example 1, at a temperature of 180 ° and a pressure of 0.2 MPa while flowing nitrogen gas. Then, HF was supplied at 5 5. 3 8 NL / hr, and the supply of nitrogen gas was stopped. Thereafter, ethyl chloride (stabilizer: containing 2 1 2 mass ppm) shown in Raw Material Example 1 was fed at 4.6 2 N L / hr to start the reaction. About 6 hours after the start of the reaction, the outlet gas was washed with an alkaline aqueous solution and analyzed by gas chromatography. The results are shown below.
  • the present invention is industrially useful because it enables economical production of high-purity fluoretane and uses the obtained fluoretane as a low-temperature refrigerant as an etching gas.

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

Abstract

L’invention concerne un procédé servant à purifier du chlorure d'éthyle selon lequel on met en contact du chlorure d'éthyle brut contenant un stabilisant et/ou de l'humidité avec une zéolithe ayant une taille moyenne des pores de 3-11 µm et/ou avec un adsorbant en matière carbonée ayant une taille moyenne des pores de 3,4-11 µm dans une phase liquide pour réduire la quantité du stabilisant et/ou de l'humidité contenus dans le chlorure d'éthyle brut. L’invention concerne également un procédé servant à produire du fluoroéthane en utilisant le chlorure d'éthyle obtenu par un tel procédé de purification. Le procédé de purification permet d'enlever les stabilisants et l'humidité contenus dans du chlorure d'éthyle et on peut le mettre en oeuvre industriellement dans la mesure où les opérations du procédé sont faciles à réaliser.
PCT/JP2005/016155 2004-09-16 2005-08-29 Procédé servant à purifier du chlorure d'éthyle et procédé servant à produire du fluoroéthane en utilisant celui-ci WO2006030656A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2006535726A JP4953819B2 (ja) 2004-09-16 2005-08-29 塩化エチルの精製方法およびそれを用いるフルオロエタンの製造方法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2004-269668 2004-09-16
JP2004269668 2004-09-16

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WO2006030656A1 true WO2006030656A1 (fr) 2006-03-23

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JP (1) JP4953819B2 (fr)
TW (1) TW200616930A (fr)
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112105594A (zh) * 2018-05-07 2020-12-18 大金工业株式会社 1,2－二氟乙烯和/或1,1,2－三氟乙烷的制造方法

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112062652A (zh) * 2020-09-11 2020-12-11 浙江嘉华化工有限公司 一种氯乙烷精制的方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH05504138A (ja) * 1990-02-15 1993-07-01 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー ハロゲン交換フッ素化
JPH05506017A (ja) * 1990-03-20 1993-09-02 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー ハロゲン交換フッ素化
JPH05286875A (ja) * 1992-04-13 1993-11-02 Showa Denko Kk トリクロルエチレン中の安定剤の除去方法
JPH08310980A (ja) * 1995-05-18 1996-11-26 Showa Denko Kk フッ素化反応用ハロゲン化炭化水素

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2458819A (en) * 1944-09-23 1949-01-11 Standard Oil Dev Co Purifying alkyl halides

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH05504138A (ja) * 1990-02-15 1993-07-01 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー ハロゲン交換フッ素化
JPH05506017A (ja) * 1990-03-20 1993-09-02 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー ハロゲン交換フッ素化
JPH05286875A (ja) * 1992-04-13 1993-11-02 Showa Denko Kk トリクロルエチレン中の安定剤の除去方法
JPH08310980A (ja) * 1995-05-18 1996-11-26 Showa Denko Kk フッ素化反応用ハロゲン化炭化水素

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112105594A (zh) * 2018-05-07 2020-12-18 大金工业株式会社 1,2－二氟乙烯和/或1,1,2－三氟乙烷的制造方法
CN112105594B (zh) * 2018-05-07 2023-08-25 大金工业株式会社 1,2－二氟乙烯和/或1,1,2－三氟乙烷的制造方法

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JPWO2006030656A1 (ja) 2008-05-15
TW200616930A (en) 2006-06-01
JP4953819B2 (ja) 2012-06-13

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