WO2024253099A1 - Procédé de fabrication de fluoromonomère - Google Patents

Procédé de fabrication de fluoromonomère Download PDF

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Publication number
WO2024253099A1
WO2024253099A1 PCT/JP2024/020403 JP2024020403W WO2024253099A1 WO 2024253099 A1 WO2024253099 A1 WO 2024253099A1 JP 2024020403 W JP2024020403 W JP 2024020403W WO 2024253099 A1 WO2024253099 A1 WO 2024253099A1
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Prior art keywords
fluoromonomer
producing
fluoropolymer
heating furnace
corrosion potential
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PCT/JP2024/020403
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English (en)
Japanese (ja)
Inventor
智行 藤田
貴行 酒井
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AGC Inc
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Asahi Glass Co Ltd
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Priority to JP2025526119A priority Critical patent/JPWO2024253099A1/ja
Publication of WO2024253099A1 publication Critical patent/WO2024253099A1/fr
Anticipated expiration legal-status Critical
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/361—Preparation of halogenated hydrocarbons by reactions involving a decrease in the number of carbon atoms
    • C07C17/367—Preparation of halogenated hydrocarbons by reactions involving a decrease in the number of carbon atoms by depolymerisation
    • 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
    • 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
    • C07C21/185—Tetrafluoroethene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C23/00—Compounds containing at least one halogen atom bound to a ring other than a six-membered aromatic ring
    • C07C23/02—Monocyclic halogenated hydrocarbons
    • C07C23/06—Monocyclic halogenated hydrocarbons with a four-membered ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J11/00—Recovery or working-up of waste materials
    • C08J11/04—Recovery or working-up of waste materials of polymers
    • C08J11/10—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation
    • C08J11/16—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with inorganic material

Definitions

  • the present invention relates to a method for producing a fluoromonomer.
  • Patent Document 1 discloses a method for obtaining fluoroolefins by pyrolyzing a fluoropolymer in the presence of water vapor using a rotary kiln.
  • the present invention was made in consideration of the above problems, and aims to provide a method for producing fluoromonomers that is less likely to cause corrosion of the inner walls of the heating furnace.
  • a method for producing a fluoromonomer comprising heating a fluoropolymer in a heating furnace to pyrolyze the fluoropolymer to obtain a fluoromonomer
  • a method for producing a fluoromonomer characterized in that a second member exhibiting a corrosion potential lower than the corrosion potential of a first member constituting the inner wall surface of the heating furnace is present in the heating furnace, and the fluoropolymer is thermally decomposed.
  • [3] The method for producing a fluoromonomer according to [1] or [2], wherein the second member contains at least one selected from the group consisting of aluminum, iron, copper, zinc, and magnesium.
  • [4] The method for producing a fluoromonomer according to any one of [1] to [3], wherein the fluoropolymer comprises at least one selected from the group consisting of polytetrafluoroethylene, tetrafluoroethylene copolymers, polychlorotrifluoroethylene, polyvinylidene fluoride, polyvinyl fluoride, vinylidene fluoride-hexafluoropropylene copolymers, and perfluoropolyether rubber.
  • [5] The method for producing a fluoromonomer according to any one of [1] to [4], wherein the heating furnace is a rotary kiln.
  • [6] The method for producing a fluoromonomer according to any one of [1] to [5], wherein the corrosion potential of the first member is greater than ⁇ 0.3 V and not greater than 0.3 V, and the corrosion potential of the second member is ⁇ 2.0 to ⁇ 0.3 V.
  • [7] The method for producing a fluoromonomer according to any one of [1] to [6], wherein the ratio of the total surface area of the second member to the total surface area of the inner wall surface of the heating furnace is 1.0 to 20.0%.
  • [8] The method for producing a fluoromonomer according to any one of [1] to [7], wherein the heating temperature during heating of the fluoropolymer is 300° C. or higher and 800° C. or lower.
  • the present invention provides a method for producing fluoromonomers that is less susceptible to corrosion of the inner walls of the heating furnace.
  • FIG. 1 is a schematic side view showing an example of a thermal decomposition apparatus used in the method for producing a fluoromonomer of the present invention.
  • a numerical range expressed using “to” means a range that includes the numerical values before and after “to” as the lower and upper limits.
  • the term “unit” refers collectively to an atomic group derived from one molecule of a monomer that is formed directly by polymerization of the monomer, and an atomic group obtained by chemically converting a part of the atomic group.
  • a "unit based on a monomer” will also be simply referred to as a "unit”.
  • the method for producing a fluoromonomer of the present invention (hereinafter also referred to as "the present production method") is a method for producing a fluoromonomer, which comprises heating a fluoropolymer in a heating furnace and pyrolyzing the fluoropolymer to obtain a fluoromonomer, and in which a second member having a corrosion potential lower than the corrosion potential of a first member constituting the inner wall surface of the heating furnace is present in the heating furnace to pyrolyze the fluoropolymer.
  • the present production method is suitable for recycling the fluoropolymer.
  • the fluorine-containing polymer is not particularly limited as long as it is a polymer containing fluorine atoms, and may be a resin or a rubber.
  • the fluoropolymer may be one obtained from waste materials containing a fluoropolymer.
  • the fluoropolymer preferably contains at least one selected from the group consisting of polytetrafluoroethylene (hereinafter also referred to as "PTFE”), tetrafluoroethylene copolymer, polychlorotrifluoroethylene (hereinafter also referred to as "PCTFE”), polyvinylidene fluoride (hereinafter also referred to as "PVdF”), polyvinyl fluoride (hereinafter also referred to as "PVF”), vinylidene fluoride-hexafluoropropylene copolymer (hereinafter also referred to as "FKM”), and perfluoropolyether rubber.
  • PTFE polytetrafluoroethylene
  • PCTFE polychlorotrifluoroethylene
  • PVdF polyvinylidene fluoride
  • PVdF polyvinyl fluoride
  • FKM vinylidene fluoride-hexafluoropropylene copolymer
  • FKM vinyli
  • tetrafluoroethylene copolymers include tetrafluoroethylene-ethylene copolymer (hereinafter also referred to as "ETFE”), tetrafluoroethylene-hexafluoropropylene copolymer (hereinafter also referred to as "FEP”), tetrafluoroethylene-propylene copolymer (hereinafter also referred to as "FEPM”), and tetrafluoroethylene-perfluoroalkyl vinyl ether copolymer.
  • ETFE tetrafluoroethylene-ethylene copolymer
  • FEP tetrafluoroethylene-hexafluoropropylene copolymer
  • FEPM tetrafluoroethylene-propylene copolymer
  • tetrafluoroethylene-perfluoroalkyl vinyl ether copolymer tetrafluoroethylene-perfluoroalkyl vinyl ether copolymer.
  • tetrafluoroethylene-perfluoroalkyl vinyl ether copolymer a copolymer in which the ratio of tetrafluoroethylene units (hereinafter also referred to as "TFE units”) and perfluoroalkyl vinyl ether units (hereinafter also referred to as "PAVE units”) to the total of PAVE units is 0.1 mol % or more and less than 20 mol % (hereinafter also referred to as "PFA”), and a copolymer in which the ratio of PAVE units is 20 to 70 mol % (hereinafter also referred to as "FFKM”) are preferred.
  • TFE units tetrafluoroethylene units
  • PAVE units perfluoroalkyl vinyl ether units
  • PFA may be a copolymer consisting of only TFE units and PAVE units, or may contain one or more units based on other monomers other than these.
  • specific examples of other monomers include other fluorine monomers (e.g., hexafluoropropylene) and monomers having an oxygen-containing polar group (e.g., 5-norbornene-2,3-dicarboxylic anhydride).
  • FFKM may be a copolymer consisting of only TFE units and PAVE units, or may contain one or more units based on other monomers other than these.
  • Other monomers include units based on a monomer having a fluorine atom and a nitrile group, and units based on a monomer having a fluorine atom and multiple vinyl groups.
  • the form of the fluoropolymer is not particularly limited, but is preferably in the form of a sheet or granules in order to further improve the pyrolysis efficiency.
  • the size of the fluoropolymer is preferably 1 to 10 mm, more preferably 2 to 5 mm, in order to further improve the effects of the present invention.
  • the size of the fluoropolymer means the thickness when the fluoropolymer is in the form of a sheet, and means the average particle size based on a sieve when the fluoropolymer is in the form of granules. The thickness can be measured with a thickness gauge or the like, and the particle size can be measured with a sieve having various openings.
  • the fluoropolymer may be previously subjected to a pulverization treatment, cutting treatment or the like so as to have the above-mentioned size.
  • a pyrolysis apparatus 1 shown in Fig. 1 As an example of a pyrolysis apparatus including a heating furnace used in the present production method, a pyrolysis apparatus 1 shown in Fig. 1 will be described in detail.
  • Fig. 1 is a schematic side view showing an example of a pyrolysis apparatus usable in the present production method, and shows a part of its internal structure.
  • the pyrolysis device 1 has a hopper 10 capable of storing raw material (such as a fluoropolymer), a cylindrical rotary kiln 20 into which the raw material is supplied, a recovery container 30 connected to the rotary kiln 20 and for recovering pyrolysis products of the raw material (such as a fluoromonomer) and residues, a first member 40 that forms the inner wall surface of the rotary kiln 20, and a second member 50 that is arranged inside the rotary kiln 20.
  • raw material such as a fluoropolymer
  • a cylindrical rotary kiln 20 into which the raw material is supplied
  • a recovery container 30 connected to the rotary kiln 20 and for recovering pyrolysis products of the raw material (such as a fluoromonomer) and residues
  • a first member 40 that forms the inner wall surface of the rotary kiln 20
  • a second member 50 that is arranged inside the rotary kiln 20.
  • the rotary kiln 20 has a rotating means (not shown) for rotating the rotary kiln 20, and a heating means (not shown) for heating the raw materials supplied inside the rotary kiln 20.
  • a stirring means may be provided inside the rotary kiln 20 to improve the efficiency of pyrolysis of the raw materials.
  • the first member 40 is a member that constitutes the inner wall surface of the rotary kiln 20, and may constitute all or part of the inner wall surface.
  • the corrosion potential of the first member 40 is preferably greater than ⁇ 0.3 V and equal to or less than 0.3 V, and more preferably greater than ⁇ 0.3 V and equal to or less than 0.2 V.
  • the corrosion potential is a value (V vs. SCE) measured in seawater using an electrochemical measuring device (for example, "Electrochemical Measuring System HZ-5000" manufactured by Hokuto Denko Corporation).
  • the measurement conditions are a saturated calomel electrode (SEC) as the reference electrode, a flow rate of 2.4 to 4.0 m/s, and a temperature of 11 to 27° C.
  • the first member 40 constituting the inner wall surface of the rotary kiln 20 is not particularly limited, but preferably contains at least one selected from the group consisting of nickel and chromium, and may be an alloy of these.
  • the member containing at least one selected from the group consisting of nickel and chromium include stainless steel and heat-resistant steel.
  • Stainless steels include SUS302, 304, 316, 317, 321, 347, 410, 416 and 430, as well as Alloy 20.
  • heat-resistant steels include SUH309, 310, 330, 660, 661, SUH21, 409, 409L, and 446.
  • Alloys include nickel-chromium alloys such as K-500, Alloy B, C, 825, 20, 400 and 600.
  • the second member 50 is a member that exhibits a corrosion potential lower than the corrosion potential of the first member 40, and the second member 50 makes the first member 40 less susceptible to corrosion even when the fluoropolymer is thermally decomposed.
  • the corrosion potential of the second member 50 is preferably ⁇ 2.0 to ⁇ 0.3V, and more preferably ⁇ 1.1 to ⁇ 0.5V.
  • the corrosion potential of the second member 50 is measured in the same manner as the corrosion potential of the first member 40 described above.
  • the second member 50 is not particularly limited, but preferably contains at least one selected from the group consisting of aluminum, iron, copper, zinc, and magnesium, and may be an alloy of these. Iron and iron alloys include cast iron and mild steel.
  • the shape of the second member 50 may be any of a granule, a polyhedron, a pyramid, a double pyramid, a frustum, a cylinder, and an ellipsoid, and second members 50 of two or more different shapes may be used in combination.
  • the second member 50 may be present in the heating furnace, and there is no particular limitation on the arrangement of the second member 50.
  • the second member may be placed in contact with the inner wall surface of the heating furnace as shown in Fig. 1, or may be fixed to the first member 40 via a fixing member (not shown).
  • Specific examples of methods for disposing the second member 50 on the inner wall surface (first member 40) of the heating furnace include a method of directly welding the second member 50 to the inner wall surface of the heating furnace, a method of screwing the second member 50, a method of fixing the second member 50 to the inner wall surface of the heating furnace via a mounting hook, a method of providing a protrusion on part of the inner wall surface of the heating furnace and fixing the second member 50 to the protrusion, and combinations of these.
  • the ratio of the total surface area of the second member 50 to the total surface area of the inner wall surface of the heating furnace is preferably 1.0 to 20.0%, and more preferably 5.0 to 15.0%, in terms of being able to suppress corrosion of the first member 40.
  • the corrosion potential difference which represents the absolute value of the difference between the corrosion potential of the first member 40 and the corrosion potential of the second member 50, is preferably 0.1 to 2.3 V, and more preferably 0.2 to 1.5 V, in order to suppress corrosion of the first member 40.
  • the raw materials supplied to and temporarily stored inside the hopper 10 are transported by a conveyor 12 provided at a position adjacent to the hopper 10, and are supplied to the inside of the rotary kiln 20 via a feed chute 14 connected to the rotary kiln 20.
  • steam preferably superheated steam
  • the steam supplied into the charging chute is blown into the rotary kiln 20 through the charging chute.
  • FIG. 1 an example in which the steam supply pipe 16 is connected to the charging chute 14 is shown, but the present invention is not limited to this, and the steam supply pipe 16 may be directly connected to the rotary kiln 20.
  • the raw materials supplied to the inside of the rotary kiln 20 are heated by the heating means and stirred by the rotation of the rotary kiln 20.
  • the raw materials are pyrolyzed inside the rotary kiln 20, and the pyrolyzed products of the raw materials are sent to a recovery container 30.
  • the gas components of the pyrolyzed products of the raw materials are recovered via a gas recovery pipe 32, and the solid components of the pyrolyzed products of the raw materials are recovered from inside the recovery container 30.
  • the heating temperature of the fluoropolymer is preferably 300° C. or higher, more preferably 350° C. or higher, and even more preferably 400° C. or higher, from the viewpoint of improving the efficiency of thermal decomposition of the fluoropolymer.
  • the heating temperature of the fluoropolymer is preferably lower from the viewpoint of the design temperature of the equipment, and is preferably 800° C. or lower, more preferably 700° C. or lower, and even more preferably 600° C. or lower.
  • the pyrolysis of the fluoropolymer can be carried out by using a known heating device, but it is preferably carried out by using a rotary kiln in view of the superior effect of the present invention.
  • the rotary kiln is a rotary furnace, and in this production method, for example, the apparatus described in Japanese Patent No. 4,010,300 or the apparatus described in Japanese Patent No. 4,357,999 can be used.
  • fluoromonomers obtainable by this production method include tetrafluoroethylene (hereinafter also referred to as "TFE”), hexafluoropropylene (hereinafter also referred to as "HFP”), octafluorocyclobutane (hereinafter also referred to as “c-318"), vinylidene fluoride, vinyl fluoride, chlorotrifluoroethylene, perfluoroalkyl vinyl ether, and mixtures of two or more of these.
  • TFE tetrafluoroethylene
  • HFP hexafluoropropylene
  • c-318 octafluorocyclobutane
  • vinylidene fluoride vinyl fluoride
  • chlorotrifluoroethylene perfluoroalkyl vinyl ether
  • Example 1 to 4 are working examples
  • Example 5 is a comparative example.
  • the present invention is not limited to these examples.
  • PTFE polytetrafluoroethylene
  • PFA tetrafluoroethylene-perfluoroalkyl vinyl ether copolymer
  • the corrosion potentials of the first member and the second member were measured by the method described above. As a result, the corrosion potential of the second member was lower than the corrosion potential of the first member. Specifically, the corrosion potential of SUS304 was ⁇ 0.1 V, the corrosion potential of Alloy C was 0 V, and the corrosion potential of cast iron was ⁇ 0.7 V.
  • Example 1 In the rotary kiln of the pyrolysis device, a columnar cast iron (15 mm x 15 mm x 250 mm, 9.8% of the total surface area of the inner wall of the rotary kiln) was used as the second member, and one side of the second member (15 mm x 250 mm) was placed in contact with the surface of the first member ( Figure 1). After that, 300 g of PTFE was introduced into the rotary kiln, and the inside of the rotary kiln was heated to 600 ° C. Then, 300 g / h of PTFE and 1000 g / h of steam were supplied to the inside of the rotary kiln to perform pyrolysis of PTFE.
  • the rotation speed of the rotary kiln during pyrolysis was 5 rpm. After the operation was continued for 100 hours, the amount of solid matter recovered from the rotary kiln and the recovery vessel was weighed, and the conversion rate of PTFE was calculated from the input amount. The results are shown in Table 1. In addition, the gas generated during the operation was measured by gas chromatography, and TFE, HFP, and c-318 were detected. The selectivity of each component is shown in Table 1. After the above operation, the first member and the second member were collected to check for the presence or absence of corrosion and the amount of reduction in the second member (the amount of mass reduction before and after the above operation). The results are shown in Table 1.
  • Examples 2 to 4 As shown in Table 1, pyrolysis and analysis were carried out in the same manner as in Example 1, except that the shapes and materials of the raw materials, the first member, and the second member were changed.
  • Example 5 Except for not using the second member, the pyrolysis and analysis of PTFE were carried out in the same manner as in Example 1. As a result, discoloration (corrosion) was confirmed in about 30% of the total surface area of the inner wall surface (first member) of the rotary kiln.
  • surface area ratio indicates the ratio of the total surface area of the second member to the total surface area of the inner wall surface of the heating furnace (surface area of the first member).

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Sustainable Development (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

L'invention fournit un procédé de fabrication de fluoromonomère selon lequel la corrosion de la paroi interne d'un four est peu susceptible de s'étendre.　Plus précisément, l'invention concerne un procédé de fabrication de fluoromonomère selon lequel un polymère fluoré est chauffé à l'intérieur du four, et soumis à une pyrolyse, et un fluoromonomère est ainsi obtenu. Ce procédé de fabrication de fluoromonomère est caractéristique en ce qu'un second élément présentant un potentiel de corrosion inférieur au potentiel de corrosion d'un premier élément configurant une face paroi interne du four, est présent à l'intérieur du four, et la pyrolyse du polymère fluoré est effectuée.
PCT/JP2024/020403 2023-06-09 2024-06-04 Procédé de fabrication de fluoromonomère Pending WO2024253099A1 (fr)

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JP2025526119A JPWO2024253099A1 (fr) 2023-06-09 2024-06-04

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JP2023-095624 2023-06-09
JP2023095624 2023-06-09

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WO2024253099A1 true WO2024253099A1 (fr) 2024-12-12

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Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH05503736A (ja) * 1990-03-01 1993-06-17 ヘキスト・アクチェンゲゼルシャフト カルボン酸塩化物を製造する際の金属性構造材料の腐食を防止する方法
JPH1096092A (ja) * 1996-09-24 1998-04-14 Togo Seisakusho:Kk 亜鉛入り防食材料
WO2003074456A1 (fr) * 2002-03-01 2003-09-12 Daikin Industries, Ltd. Procede de production de monomere fluore
JP2004346000A (ja) * 2003-05-21 2004-12-09 Taiyo Kogyo Corp ケミカルリサイクル方法
JP2005068253A (ja) * 2003-08-21 2005-03-17 Nippon Light Metal Co Ltd 鋼製部材防蝕用塗料
JP2007162130A (ja) * 2005-11-15 2007-06-28 Meisei Ind Co Ltd 暗中で使用される金属用の防食被膜、暗中での金属の防食方法および複合被膜
CN101462925A (zh) * 2009-01-14 2009-06-24 中化国际（苏州）新材料研发有限公司 一种聚四氟乙烯热裂解制备四氟乙烯的方法

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH05503736A (ja) * 1990-03-01 1993-06-17 ヘキスト・アクチェンゲゼルシャフト カルボン酸塩化物を製造する際の金属性構造材料の腐食を防止する方法
JPH1096092A (ja) * 1996-09-24 1998-04-14 Togo Seisakusho:Kk 亜鉛入り防食材料
WO2003074456A1 (fr) * 2002-03-01 2003-09-12 Daikin Industries, Ltd. Procede de production de monomere fluore
JP2004346000A (ja) * 2003-05-21 2004-12-09 Taiyo Kogyo Corp ケミカルリサイクル方法
JP2005068253A (ja) * 2003-08-21 2005-03-17 Nippon Light Metal Co Ltd 鋼製部材防蝕用塗料
JP2007162130A (ja) * 2005-11-15 2007-06-28 Meisei Ind Co Ltd 暗中で使用される金属用の防食被膜、暗中での金属の防食方法および複合被膜
CN101462925A (zh) * 2009-01-14 2009-06-24 中化国际（苏州）新材料研发有限公司 一种聚四氟乙烯热裂解制备四氟乙烯的方法

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