WO2024252819A1 - Procédé de séparation de fluorure de vinylidène et procédé de production de fluorure de vinylidène - Google Patents

Procédé de séparation de fluorure de vinylidène et procédé de production de fluorure de vinylidène Download PDF

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Publication number
WO2024252819A1
WO2024252819A1 PCT/JP2024/016135 JP2024016135W WO2024252819A1 WO 2024252819 A1 WO2024252819 A1 WO 2024252819A1 JP 2024016135 W JP2024016135 W JP 2024016135W WO 2024252819 A1 WO2024252819 A1 WO 2024252819A1
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Prior art keywords
vinylidene fluoride
vdf
methane
gas
molar amount
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Ceased
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PCT/JP2024/016135
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English (en)
Japanese (ja)
Inventor
覚人 三竹
英史 塩田
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AGC Inc
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Asahi Glass Co Ltd
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Publication date
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Priority to JP2025525985A priority Critical patent/JPWO2024252819A1/ja
Priority to CN202480037166.2A priority patent/CN121285538A/zh
Publication of WO2024252819A1 publication Critical patent/WO2024252819A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/38—Separation; Purification; Stabilisation; Use of additives
    • C07C17/383—Separation; Purification; Stabilisation; Use of additives by distillation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C21/00—Acyclic unsaturated compounds containing halogen atoms
    • C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
    • C07C21/18—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing fluorine

Definitions

  • the present disclosure relates to a method for separating vinylidene fluoride and a method for producing vinylidene fluoride.
  • Vinylidene fluoride is useful as a monomer for fluororesins.
  • Patent Document 1 describes a method for producing 2,3,3,3-tetrafluoropropene, which includes the steps of (a) supplying a mixture of chlorodifluoromethane and methyl chloride in a molar ratio of 3.2 to 4.7 into a reaction vessel, (b) supplying a heat transfer medium to the mixture of step (a) to produce a second mixture containing 2,3,3,3-tetrafluoropropene and methyl chloride, (c) drying the second mixture of step (b) to obtain an anhydrous second mixture, (d) contacting the anhydrous second mixture of step (c) with a molecular sieve having a pore size of 4 ⁇ to obtain a third mixture not containing methyl chloride, and (e) separating 2,3,3,3-tetrafluoropropene from the third mixture of step (d).
  • Patent Document 1 aims to separate and obtain 2,3,3,3-tetrafluoropropene, and does not anticipate separating vinylidene fluoride (VdF). Furthermore, Patent Document 1 does not focus on separating VdF from low-boiling-point gases (e.g., methane).
  • VdF vinylidene fluoride
  • One aspect of the present disclosure aims to provide a method for efficiently separating VdF from a mixed gas containing methane and VdF, and a method for producing VdF.
  • a method for separating vinylidene fluoride comprising a separation step of contacting a first gas containing methane and vinylidene fluoride with a first liquid containing at least one solvent selected from the group consisting of chloromethane, acetone, and 1-chloro-2,3,3-trifluoro-1-propene to obtain a second gas having a molar amount of vinylidene fluoride lower than that of the first gas relative to the total molar amount of methane and vinylidene fluoride, and a second liquid containing vinylidene fluoride and the solvent.
  • the solvent is at least one selected from the group consisting of chloromethane and acetone.
  • ⁇ 3> The method for separating vinylidene fluoride according to ⁇ 1> or ⁇ 2>, wherein when the first gas and the first liquid are contacted, a ratio of a molar amount of the solvent to a total molar amount of methane and vinylidene fluoride is 10 or more.
  • ⁇ 4> The method for separating vinylidene fluoride according to any one of ⁇ 1> to ⁇ 3>, wherein the content of methane is 5 mol % or more based on the total amount of the first gas.
  • ⁇ 5> The method for separating vinylidene fluoride according to any one of ⁇ 1> to ⁇ 4>, wherein the first gas further contains at least one selected from the group consisting of carbon monoxide and carbon dioxide.
  • the first gas originates from distillate A
  • ⁇ 7> The method for separating vinylidene fluoride according to ⁇ 6>, wherein in the distillation step, a distillate B is further obtained, the distillate B having a higher molar amount of vinylidene fluoride relative to a total molar amount of methane and vinylidene fluoride than the first composition.
  • ⁇ 8> The method for separating vinylidene fluoride according to ⁇ 6>, wherein the second liquid obtained in the separation step is supplied to a distillation step.
  • a method for separating VdF that efficiently separates VdF from a mixed gas containing methane and VdF, and a method for producing VdF are provided.
  • FIG. 1 is a diagram showing an example of the flow of materials in the method for producing VdF according to the present disclosure.
  • a numerical range indicated using “to” means a range that includes the numerical values before and after “to” as the minimum and maximum values, respectively.
  • the upper or lower limit value described in a certain numerical range may be replaced with the upper or lower limit value of another numerical range described in the present disclosure.
  • the upper or lower limit value described in a certain numerical range may be replaced with a value shown in the examples.
  • combinations of two or more preferred aspects are more preferred aspects.
  • the amount of each component means the total amount of the multiple substances, unless otherwise specified.
  • distillate refers to material that is distilled from the top of a distillation column
  • bottoms refers to material that is distilled from the bottom of a distillation column.
  • main component means that the amount of components other than the component in question is relatively small.
  • the amount of the "main component” is preferably 50 mol % or more of the total, more preferably 60 mol % or more, even more preferably 70 mol % or more, and most preferably 80 mol % or more.
  • the boiling point of a compound is a value at normal pressure, which is 1.013 ⁇ 10 5 Pa.
  • the method for separating VdF disclosed herein includes a separation step of contacting a first gas containing methane and VdF with a first liquid containing at least one solvent selected from the group consisting of chloromethane, acetone, and 1-chloro-2,3,3-trifluoro-1-propene to obtain a second gas in which the molar amount of VdF relative to the total molar amount of methane and VdF is lower than that of the first gas, and a second liquid containing VdF and the solvent.
  • VdF separation method allows VdF to be efficiently separated from a gas mixture containing methane and VdF.
  • VdF is produced, for example, using chlorodifluoromethane and chloromethane as raw materials.
  • a large amount of low-boiling-point gas e.g., methane
  • VdF tends to be entrained in the low-boiling-point gas, which tends to reduce the recovery amount of the target VdF.
  • VdF can be transferred from the gas phase to the liquid phase, and VdF can be efficiently separated from a gas mixture containing VdF and methane.
  • the generated gases described in Patent Document 1 include VdF and methane, but there is no mention of the above solvent.
  • the VdF separation method disclosed herein involves contacting a first gas containing methane and VdF with a first liquid containing a solvent to obtain a second gas having a lower VdF content than the first gas, and a second liquid containing VdF and the solvent.
  • the first gas containing methane and VdF may contain other components other than methane and VdF, and the other components include, for example, fluoroolefins other than VdF, ethylene, acetylene, chloromethane, carbon monoxide, and carbon dioxide.
  • the first gas contains a low boiling point gas such as carbon monoxide or carbon dioxide
  • VdF is more likely to be entrained in the low boiling point gas, and the amount of VdF recovered tends to decrease further.
  • the entrainment of VdF in the low boiling point gas can be suppressed by contacting the first gas with the first liquid described below.
  • the first gas further contains at least one species selected from the group consisting of carbon monoxide and carbon dioxide, the effect of suppressing the entrainment of VdF in the low boiling point gas is high.
  • the methane content is, for example, 5 mol% or more, or may be 10 mol% or more, or may be 20 mol% or more, relative to the total amount of the first gas.
  • the upper limit of the methane content is, for example, 40 mol%.
  • VdF When the methane content is 5 mol% or more, VdF is more likely to be entrained in the low boiling point gas, and the amount of VdF recovered tends to decrease further.
  • the entrainment of VdF in the low boiling point gas can be suppressed by contacting the first gas with the first liquid described below.
  • the methane content relative to the total amount of the first gas is 5 mol% or more, the effect of suppressing the entrainment of VdF in the low boiling point gas is high.
  • the VdF content is, for example, 10 mol% or more, or may be 20 mol% or more, or may be 30 mol% or more, relative to the total amount of the first gas.
  • the upper limit of the VdF content is, for example, 50 mol%.
  • the molar ratio of VdF to methane is not particularly limited. From the viewpoint of production efficiency, the ratio of the molar amount of methane to the molar amount of VdF (i.e., the molar ratio) is preferably 1/5 or less, more preferably 1/10 or less, and even more preferably 1/15 or less.
  • the first gas can be, for example, a reaction product containing VdF obtained by reacting various raw materials for the purpose of producing VdF.
  • the first liquid contains at least one solvent (hereinafter also referred to as the "specific solvent") selected from the group consisting of chloromethane, acetone, and 1-chloro-2,3,3-trifluoro-1-propene.
  • the specific solvent selected from the group consisting of chloromethane, acetone, and 1-chloro-2,3,3-trifluoro-1-propene.
  • the first liquid may contain components other than the specific solvent, but the content of components other than the specific solvent is preferably 5 mol % or less, and it is more preferable for the first liquid to consist only of the specific solvent.
  • the specific solvent is preferably at least one selected from the group consisting of chloromethane and acetone, because of its excellent VdF separation properties, and chloromethane or acetone is more preferable.
  • the ratio of the molar amount of the specific solvent to the total molar amount of methane and VdF is preferably 10 or more, and more preferably 15 or more.
  • the upper limit of the above ratio is, for example, 25.
  • specific solvent/(methane+VdF) represents the molar ratio of the amount of specific solvent supplied to the absorption tower to the total amount of methane and VdF supplied to the absorption tower.
  • the method of contacting the first gas containing methane and VdF with the specific solvent is not particularly limited.
  • the second gas has a lower molar amount of VdF relative to the total molar amount of methane and VdF than the first gas.
  • the second liquid contains VdF and a specific solvent. That is, in the VdF separation method of the present disclosure, by using the specific solvent, a part of the VdF contained in the first gas can be transferred to the second liquid, and VdF can be efficiently separated.
  • the method for separating VdF of the present disclosure further includes a distillation step of distilling a first composition containing VdF, methane, and a specific solvent to obtain a distillate A containing methane and VdF and a bottom product containing the specific solvent as a main component, respectively.
  • the first gas in the separation step is derived from the distillate A
  • the first liquid in the separation step is derived from the bottom product.
  • the distillation process can be carried out using a commonly used distillation apparatus, for example, a distillation tower such as a plate tower, a packed tower, etc.
  • a distillation tower such as a plate tower, a packed tower, etc.
  • Various conditions of the distillation process for example, the operating temperature, operating pressure, reflux ratio, total number of stages in the distillation tower, position of the charging stage, position of the solvent supply stage, etc., are not particularly limited and can be appropriately selected to achieve the desired separation.
  • the number of stages of the distillation tower can be, for example, 1 to 100, and from the viewpoint of obtaining VdF with high purity, 30 or more is preferable, and 50 or more is more preferable. Since VdF has a low boiling point, it is preferable to distill it under pressure, for example, at a pressure of 0 to 5 MPaG (gauge pressure).
  • the temperatures at the top and bottom of the distillation tower are determined according to the operating pressure and the composition of the distillate and bottom products.
  • the temperature at the top of the tower be -60 to 100°C and the temperature at the bottom of the tower be -10 to 300°C.
  • Distillation can be performed in either a batch or continuous manner, and in some cases it can also be performed in a semi-continuous manner in which the distillate and bottom products are intermittently withdrawn or intermittently charged.
  • the first composition is distilled to obtain a distillate A containing methane and VdF and a bottoms product containing the specific solvent as a main component.
  • Distillate A preferably has a lower molar amount of VdF relative to the total molar amount of methane and VdF than the first composition.
  • distillation process it is preferable to further obtain a distillate B in which the molar amount of VdF relative to the total molar amount of methane and VdF is higher than that of the first composition.
  • Distillate B has a higher purity of VdF than the first composition, but distillate B may be further distilled to increase the purity of VdF.
  • the first gas in the above separation process is derived from distillate A.
  • the first gas is derived from distillate A means that the first gas is a gas obtained from distillate A.
  • the first gas may be distillate A itself, or the first gas may be a gas after distillate A has been subjected to any treatment.
  • the first gas may be a gas after any component has been added to distillate A.
  • the any component may be a component contained in distillate A, or may be a component other than the component contained in distillate A.
  • the first gas may be a gas after at least a portion of the components contained in distillate A has been removed from distillate A.
  • the first liquid in the separation process is derived from the bottom product.
  • the first liquid is derived from the bottom product means that the first liquid is a liquid obtained from the bottom product.
  • the first liquid may be the bottom product itself, or the first liquid may be a liquid obtained after the bottom product has been subjected to any processing.
  • the first liquid may be a liquid obtained after any component has been added to the bottom product.
  • the any component may be a component contained in the bottom product, or a component other than the components contained in the bottom product.
  • the first liquid may be a liquid obtained after at least a portion of the components contained in the bottom product has been removed from the bottom product.
  • the first gas and first liquid obtained by distilling the first composition are used in the separation process, and after obtaining the second liquid in the separation process, the second liquid is supplied to the distillation process, thereby suppressing the loss of VdF due to entrainment with methane (reduction in the amount of VdF recovered).
  • the method for producing VdF disclosed herein includes a distillation step of distilling a second composition containing methane and VdF to obtain a distillate C having a lower molar amount of VdF relative to the total molar amount of methane and VdF than the second composition, and a distillate D having a higher molar amount of VdF relative to the total molar amount of methane and VdF than the second composition; a separation step of contacting distillate C with a first liquid containing a specific solvent to obtain a second liquid containing VdF and the specific solvent; a step of supplying the second liquid obtained in the separation step to the distillation step; and a purification step of purifying distillate D to obtain VdF.
  • the preferred embodiment of the separation step in the VdF manufacturing method of the present disclosure is the same as the preferred embodiment of the separation step in the VdF separation method described above.
  • the purification process may involve multiple distillations.
  • the method for producing VdF disclosed herein preferably further includes a step of reacting chloromethane with chlorodifluoromethane to obtain a second composition containing methane and VdF.
  • a diluent When reacting chloromethane with chlorodifluoromethane, a diluent may be used.
  • An example of the diluent is water vapor.
  • a second composition G containing methane and VdF is produced in the reactor T, and the second composition G is supplied to a distillation column M1.
  • a distillate C in which the molar amount of VdF relative to the total molar amount of methane and VdF is lower than that of the second composition G, is extracted from the top side of the distillation column M1.
  • a distillate D in which the molar amount of VdF relative to the total molar amount of methane and VdF is higher than that of the second composition G, is extracted from the middle stage of the distillation column M1.
  • the distillate C and the specific solvent S are supplied to an absorption tower M2.
  • a second liquid E containing VdF and the specific solvent is extracted from the bottom side of the absorption tower M2.
  • the second liquid E is supplied together with the second composition G to the distillation column M1.
  • the distillate C extracted from the distillation column M1 is supplied to the absorption column M2 and then returned to the distillation column M1, thereby making it possible to reduce the loss rate of VdF.
  • a bottom product F mainly composed of the specific solvent may be extracted from the bottom side of the distillation column M1, and the bottom product F may be purified by distillation or the like.
  • the bottom product F mainly composed of the specific solvent may be purified, and the high-purity specific solvent may be supplied to the absorption column M2.
  • Examples 1 to 3 are comparative examples, and Examples 4 to 6 are working examples.
  • AS-300 As the solvent, the compounds shown in Table 1 were used. In Example 1, no extraction solvent was used. In Table 1, details of "AS-300” are as follows. AS-300: Product name "AS-300", manufactured by AGC Co., Ltd. A mixture of 1-chloro-2,3,3-trifluoro-1-propene (E) and 1-chloro-2,3,3-trifluoro-1-propene (Z).
  • the relative volatility Rv of VdF to methane is expressed by the following formula.
  • Rv (molar fraction of VdF in the gas phase / mole fraction of VdF in the liquid phase) / (molar fraction of methane in the gas phase / mole fraction of methane in the liquid phase)
  • the relative volatility Rv of VdF to methane is measured as follows. The prepared first mixture and, if necessary, an extraction solvent were poured into a pressure-resistant autoclave equipped with a pressure gauge. The temperature was adjusted so that the pressure was about 1.0 MPaG, and the mixture was held for one day to stabilize the composition inside the autoclave.
  • solvent/(VdF+methane) means the molar amount of the solvent relative to the total molar amount of VdF and methane contained in the supply gas.
  • Method/VdF in the bottom product means the ratio (%) of the molar amount of methane to the molar amount of VdF contained in the bottom product.
  • 0.00 means a very small value that is less than 0.005.
  • Examples 11 to 15 it was found that the VdF loss rate could be reduced by using chloromethane as a solvent.
  • the ratio of the molar amount of the solvent to the total molar amount of methane and VdF was 10 or more, it was found that the VdF loss rate could be reduced to 5% or less.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Procédé de séparation de fluorure de vinylidène comprenant une étape de séparation au cours de laquelle un premier gaz contenant du méthane et du fluorure de vinylidène est mis en contact avec un premier liquide contenant au moins un solvant choisi dans le groupe constitué par le chlorométhane, l'acétone et le 1-chloro-2,3,3-trifluoro-1-propène pour obtenir un second liquide contenant du fluorure de vinylidène et le solvant, et un second gaz ayant par rapport au premier gaz une quantité molaire inférieure de fluorure de vinylidène rapportée à la quantité molaire totale de méthane et de fluorure de vinylidène.
PCT/JP2024/016135 2023-06-08 2024-04-24 Procédé de séparation de fluorure de vinylidène et procédé de production de fluorure de vinylidène Ceased WO2024252819A1 (fr)

Priority Applications (2)

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JP2025525985A JPWO2024252819A1 (fr) 2023-06-08 2024-04-24
CN202480037166.2A CN121285538A (zh) 2023-06-08 2024-04-24 偏氟乙烯的分离方法和偏氟乙烯的制造方法

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JP2023-095062 2023-06-08
JP2023095062 2023-06-08

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013137409A1 (fr) * 2012-03-14 2013-09-19 旭硝子株式会社 Procédé de production de 2,3,3,3-tétrafluoropropène et de 1,1-difluoroéthylène
WO2013137408A1 (fr) * 2012-03-14 2013-09-19 旭硝子株式会社 Procédé de production de 2,3,3,3-tétrafluoropropène
WO2015072305A1 (fr) * 2013-11-14 2015-05-21 旭硝子株式会社 Procédé de séparation de fluorure de vinylidène et de trifluorométhane et procédé de production de fluorure de vinylidène
CN110818529A (zh) * 2019-10-11 2020-02-21 江苏梅兰化工有限公司 一种制备高纯偏氟乙烯的新工艺

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013137409A1 (fr) * 2012-03-14 2013-09-19 旭硝子株式会社 Procédé de production de 2,3,3,3-tétrafluoropropène et de 1,1-difluoroéthylène
WO2013137408A1 (fr) * 2012-03-14 2013-09-19 旭硝子株式会社 Procédé de production de 2,3,3,3-tétrafluoropropène
WO2015072305A1 (fr) * 2013-11-14 2015-05-21 旭硝子株式会社 Procédé de séparation de fluorure de vinylidène et de trifluorométhane et procédé de production de fluorure de vinylidène
CN110818529A (zh) * 2019-10-11 2020-02-21 江苏梅兰化工有限公司 一种制备高纯偏氟乙烯的新工艺

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