JP7258319B1 - フッ素原子含有ポリマーの分解方法、及びフッ素原子含有ポリマーの分解装置 - Google Patents
フッ素原子含有ポリマーの分解方法、及びフッ素原子含有ポリマーの分解装置 Download PDFInfo
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- 229920000642 polymer Polymers 0.000 title claims abstract description 77
- 229910052731 fluorine Inorganic materials 0.000 title claims abstract description 62
- 125000001153 fluoro group Chemical group F* 0.000 title claims abstract description 62
- 238000000034 method Methods 0.000 title claims abstract description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 44
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000001301 oxygen Substances 0.000 claims abstract description 11
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims description 40
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 27
- -1 fluoride ions Chemical class 0.000 abstract description 25
- 239000007787 solid Substances 0.000 abstract description 17
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract description 14
- 150000007514 bases Chemical class 0.000 abstract description 14
- 239000001569 carbon dioxide Substances 0.000 abstract description 7
- 229910002092 carbon dioxide Inorganic materials 0.000 abstract description 7
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract description 6
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 abstract description 6
- 238000000926 separation method Methods 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 16
- 239000002033 PVDF binder Substances 0.000 description 10
- 239000007789 gas Substances 0.000 description 10
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 10
- 238000000354 decomposition reaction Methods 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 7
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 7
- 229910001882 dioxygen Inorganic materials 0.000 description 7
- 239000002699 waste material Substances 0.000 description 7
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 5
- 229920000840 ethylene tetrafluoroethylene copolymer Polymers 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 2
- 229910001634 calcium fluoride Inorganic materials 0.000 description 2
- 229910001424 calcium ion Inorganic materials 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 229920002620 polyvinyl fluoride Polymers 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 2
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 1
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000010485 coping Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- JEGUKCSWCFPDGT-UHFFFAOYSA-N h2o hydrate Chemical compound O.O JEGUKCSWCFPDGT-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 239000002349 well water Substances 0.000 description 1
- 235000020681 well water Nutrition 0.000 description 1
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- B09—DISPOSAL OF SOLID WASTE; RECLAMATION OF CONTAMINATED SOIL
- B09B—DISPOSAL OF SOLID WASTE NOT OTHERWISE PROVIDED FOR
- B09B3/00—Destroying solid waste or transforming solid waste into something useful or harmless
- B09B3/40—Destroying solid waste or transforming solid waste into something useful or harmless involving thermal treatment, e.g. evaporation
- B09B3/45—Steam treatment, e.g. supercritical water gasification or oxidation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B09—DISPOSAL OF SOLID WASTE; RECLAMATION OF CONTAMINATED SOIL
- B09B—DISPOSAL OF SOLID WASTE NOT OTHERWISE PROVIDED FOR
- B09B5/00—Operations not covered by a single other subclass or by a single other group in this subclass
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- 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
- C08J11/14—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 steam or water
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- 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
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
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- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Environmental & Geological Engineering (AREA)
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- Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)
- Processing Of Solid Wastes (AREA)
Abstract
Description
以下、本発明のフッ素原子含有ポリマーの分解方法の一実施態様、及びフッ素原子含有ポリマーの分解装置の一実施形態について説明する。なお本発明は、以下の実施態様及び実施形態に何ら限定されるものでなく、本発明の範囲において適宜変更を加えて実施することが可能である。
上記本発明のフッ素原子含有ポリマーの分解方法を実現することのできる装置も本発明の一つである。この装置は、アルカリ金属水酸化物及びアルカリ土類金属水酸化物からなる群より選択される少なくとも1種の塩基性化合物の存在下、分解対象であるフッ素原子含有ポリマーを酸素含有雰囲気下にて170℃以上の亜臨界水に接触させるための反応容器を備えることを特徴とする。
試薬として市販されているPVDF粉末(ポリフッ化ビニリデン;フッ素原子含有率60.7質量%)30.0mgと、1.0M水酸化ナトリウム水溶液10mLを熱水リアクターに入れ、酸素ガスで0.5MPaまで加圧した後、150℃、200℃、250℃又は300℃で6時間反応させた。反応時の圧力は、1.2MPa(150℃)~9.1MPa(300℃)だった。なお、PVDF粉末30.0mg中に含まれるフッ素原子物質量は、959μmolである。反応終了後、内容物を室温まで冷却し、水相に生成したフッ化物イオンをイオンクロマトグラフィーで定量した。各反応温度でのフッ化物イオンの収量及び収率を表1に示すとともに、反応温度に対する収率のプロットを図1に示す。反応終了後、150℃で反応させたものについては反応溶液中に未反応のPDVFが観察され、200℃で反応させたものについては反応溶液が無色透明となり、その中に固体残渣は確認されなかった。250℃以上で反応させたものについては反応溶液中に黒色固体残渣が観察されたが、その量は少なかった。また、250℃のものでは反応溶液は無色透明だったが、300℃のものでは反応溶液が薄く褐色に着色していた。
加圧に用いた気体を酸素ガスに代えてアルゴンガスに変更したこと以外は実施例と同じ手順でPVDF粉末の分解を行った。各反応温度でのフッ化物イオンの収量及び収率を表2に示すとともに、反応温度に対する収率のプロットを図2に示す。全ての温度条件にて反応終了後の反応溶液は着色しており、150℃で薄い褐色に着色していたのをはじめ、温度が高くなるにつれてこの着色が濃くなっていき、300℃では墨汁のように全体が黒く着色していた。また、150℃で反応させたものについては反応溶液中に未反応のPDVFが観察され、200℃以上では反応溶液中に黒色の固体残渣が観察された。
Claims (3)
- 水酸化ナトリウム及び/又は水酸化カリウムの存在下、分解対象であるフッ素原子含有ポリマーを170℃以上250℃未満の亜臨界水に接触させる工程を含み、前記工程が酸素を含む雰囲気で行われることを特徴とするフッ素原子含有ポリマーの分解方法。
- 前記亜臨界水の温度が200℃以上250℃未満である請求項1記載のフッ素原子含有ポリマーの分解方法。
- 水酸化ナトリウム及び/又は水酸化カリウムの存在下、分解対象であるフッ素原子含有ポリマーを酸素含有雰囲気にて170℃以上250℃未満の亜臨界水に接触させるための反応容器を備えることを特徴とするフッ素原子含有ポリマーの分解装置。
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JP2021177521A JP7258319B1 (ja) | 2021-10-29 | 2021-10-29 | フッ素原子含有ポリマーの分解方法、及びフッ素原子含有ポリマーの分解装置 |
PCT/JP2022/039253 WO2023074550A1 (ja) | 2021-10-29 | 2022-10-21 | フッ素原子含有ポリマーの分解方法、及びフッ素原子含有ポリマーの分解装置 |
CN202280072668.XA CN118176248A (zh) | 2021-10-29 | 2022-10-21 | 含有氟原子的聚合物的分解方法及含有氟原子的聚合物的分解装置 |
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JP2001288480A (ja) | 2000-04-03 | 2001-10-16 | Mitsubishi Materials Corp | 廃プラスチックのガス化方法及びその装置 |
JP2014210826A (ja) | 2011-09-02 | 2014-11-13 | 旭硝子株式会社 | 含フッ素有機化合物の分解方法 |
JP2021155478A (ja) | 2020-03-25 | 2021-10-07 | 学校法人神奈川大学 | フッ素原子含有ポリマーの分解方法、及びフッ素原子含有ポリマーの分解装置 |
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JP2001288480A (ja) | 2000-04-03 | 2001-10-16 | Mitsubishi Materials Corp | 廃プラスチックのガス化方法及びその装置 |
JP2014210826A (ja) | 2011-09-02 | 2014-11-13 | 旭硝子株式会社 | 含フッ素有機化合物の分解方法 |
JP2021155478A (ja) | 2020-03-25 | 2021-10-07 | 学校法人神奈川大学 | フッ素原子含有ポリマーの分解方法、及びフッ素原子含有ポリマーの分解装置 |
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