WO2024139502A1 - 一种高白度低杂质含量的聚芳醚及其制备方法 - Google Patents
一种高白度低杂质含量的聚芳醚及其制备方法 Download PDFInfo
- Publication number
- WO2024139502A1 WO2024139502A1 PCT/CN2023/123326 CN2023123326W WO2024139502A1 WO 2024139502 A1 WO2024139502 A1 WO 2024139502A1 CN 2023123326 W CN2023123326 W CN 2023123326W WO 2024139502 A1 WO2024139502 A1 WO 2024139502A1
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- WO
- WIPO (PCT)
- Prior art keywords
- sodium
- solvent
- polyarylether
- whiteness
- resin
- Prior art date
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- 229920000090 poly(aryl ether) Polymers 0.000 title claims abstract description 63
- 238000002360 preparation method Methods 0.000 title claims abstract description 21
- 239000002904 solvent Substances 0.000 claims abstract description 106
- 229920005989 resin Polymers 0.000 claims abstract description 77
- 239000011347 resin Substances 0.000 claims abstract description 77
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 72
- 239000012752 auxiliary agent Substances 0.000 claims abstract description 51
- 238000000605 extraction Methods 0.000 claims abstract description 47
- 238000005406 washing Methods 0.000 claims abstract description 47
- 239000012535 impurity Substances 0.000 claims abstract description 40
- 238000000034 method Methods 0.000 claims abstract description 40
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims abstract description 20
- 238000006297 dehydration reaction Methods 0.000 claims abstract description 14
- 239000000463 material Substances 0.000 claims abstract description 12
- 238000004064 recycling Methods 0.000 claims abstract description 12
- 238000000746 purification Methods 0.000 claims abstract description 10
- 239000011780 sodium chloride Substances 0.000 claims abstract description 10
- 239000007788 liquid Substances 0.000 claims description 56
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 54
- 238000002386 leaching Methods 0.000 claims description 43
- 238000011084 recovery Methods 0.000 claims description 41
- 239000000047 product Substances 0.000 claims description 30
- 238000000926 separation method Methods 0.000 claims description 29
- 239000007787 solid Substances 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 239000011259 mixed solution Substances 0.000 claims description 22
- 239000000243 solution Substances 0.000 claims description 20
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 18
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- 239000000654 additive Substances 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- 230000009471 action Effects 0.000 claims description 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 238000001704 evaporation Methods 0.000 claims description 12
- 230000008020 evaporation Effects 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000005416 organic matter Substances 0.000 claims description 12
- XKMRRTOUMJRJIA-UHFFFAOYSA-N ammonia nh3 Chemical compound N.N XKMRRTOUMJRJIA-UHFFFAOYSA-N 0.000 claims description 11
- 239000011734 sodium Substances 0.000 claims description 11
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 10
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 10
- 230000000996 additive effect Effects 0.000 claims description 10
- 239000000872 buffer Substances 0.000 claims description 10
- 229910052708 sodium Inorganic materials 0.000 claims description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- -1 dichloro aromatic compound Chemical class 0.000 claims description 9
- 238000005868 electrolysis reaction Methods 0.000 claims description 9
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 8
- 230000018044 dehydration Effects 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 239000007800 oxidant agent Substances 0.000 claims description 8
- 230000001590 oxidative effect Effects 0.000 claims description 8
- 229920000412 polyarylene Polymers 0.000 claims description 8
- 238000006116 polymerization reaction Methods 0.000 claims description 8
- 239000002994 raw material Substances 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 8
- 239000012043 crude product Substances 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical group [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims description 5
- 230000005540 biological transmission Effects 0.000 claims description 5
- 238000004821 distillation Methods 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 230000003647 oxidation Effects 0.000 claims description 5
- 238000007254 oxidation reaction Methods 0.000 claims description 5
- 239000007921 spray Substances 0.000 claims description 5
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 claims description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 4
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 4
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 4
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 claims description 4
- HTXDPTMKBJXEOW-UHFFFAOYSA-N dioxoiridium Chemical compound O=[Ir]=O HTXDPTMKBJXEOW-UHFFFAOYSA-N 0.000 claims description 4
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 claims description 4
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims description 4
- 229910000457 iridium oxide Inorganic materials 0.000 claims description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 4
- MRELNEQAGSRDBK-UHFFFAOYSA-N lanthanum(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[La+3].[La+3] MRELNEQAGSRDBK-UHFFFAOYSA-N 0.000 claims description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 claims description 4
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 claims description 4
- 229940074404 sodium succinate Drugs 0.000 claims description 4
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 claims description 4
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 claims description 3
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 3
- GPAPPPVRLPGFEQ-UHFFFAOYSA-N 4,4'-dichlorodiphenyl sulfone Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC=C(Cl)C=C1 GPAPPPVRLPGFEQ-UHFFFAOYSA-N 0.000 claims description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 claims description 3
- PZYDAVFRVJXFHS-UHFFFAOYSA-N n-cyclohexyl-2-pyrrolidone Chemical compound O=C1CCCN1C1CCCCC1 PZYDAVFRVJXFHS-UHFFFAOYSA-N 0.000 claims description 3
- 235000015497 potassium bicarbonate Nutrition 0.000 claims description 3
- 229910000028 potassium bicarbonate Inorganic materials 0.000 claims description 3
- 239000011736 potassium bicarbonate Substances 0.000 claims description 3
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 3
- 229910001925 ruthenium oxide Inorganic materials 0.000 claims description 3
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 claims description 3
- KYKFCSHPTAVNJD-UHFFFAOYSA-L sodium adipate Chemical compound [Na+].[Na+].[O-]C(=O)CCCCC([O-])=O KYKFCSHPTAVNJD-UHFFFAOYSA-L 0.000 claims description 3
- 239000001601 sodium adipate Substances 0.000 claims description 3
- 235000011049 sodium adipate Nutrition 0.000 claims description 3
- BTURAGWYSMTVOW-UHFFFAOYSA-M sodium dodecanoate Chemical compound [Na+].CCCCCCCCCCCC([O-])=O BTURAGWYSMTVOW-UHFFFAOYSA-M 0.000 claims description 3
- 229940082004 sodium laurate Drugs 0.000 claims description 3
- YFMKTVBRLDLWIQ-JEDNCBNOSA-N (2s)-2,6-diaminohexanoic acid;potassium Chemical compound [K].NCCCC[C@H](N)C(O)=O YFMKTVBRLDLWIQ-JEDNCBNOSA-N 0.000 claims description 2
- SCWWKKUJPHRBRV-JEDNCBNOSA-N (2s)-2,6-diaminohexanoic acid;sodium Chemical compound [Na].NCCCC[C@H](N)C(O)=O SCWWKKUJPHRBRV-JEDNCBNOSA-N 0.000 claims description 2
- XAZKFISIRYLAEE-UHFFFAOYSA-N 1,3-dimethylcyclopentane Chemical compound CC1CCC(C)C1 XAZKFISIRYLAEE-UHFFFAOYSA-N 0.000 claims description 2
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 claims description 2
- AEQDJSLRWYMAQI-UHFFFAOYSA-N 2,3,9,10-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline Chemical compound C1CN2CC(C(=C(OC)C=C3)OC)=C3CC2C2=C1C=C(OC)C(OC)=C2 AEQDJSLRWYMAQI-UHFFFAOYSA-N 0.000 claims description 2
- CHHHXKFHOYLYRE-UHFFFAOYSA-M 2,4-Hexadienoic acid, potassium salt (1:1), (2E,4E)- Chemical compound [K+].CC=CC=CC([O-])=O CHHHXKFHOYLYRE-UHFFFAOYSA-M 0.000 claims description 2
- CYDQOEWLBCCFJZ-UHFFFAOYSA-N 4-(4-fluorophenyl)oxane-4-carboxylic acid Chemical compound C=1C=C(F)C=CC=1C1(C(=O)O)CCOCC1 CYDQOEWLBCCFJZ-UHFFFAOYSA-N 0.000 claims description 2
- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 claims description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 2
- QZKRHPLGUJDVAR-UHFFFAOYSA-K EDTA trisodium salt Chemical compound [Na+].[Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O QZKRHPLGUJDVAR-UHFFFAOYSA-K 0.000 claims description 2
- 239000012028 Fenton's reagent Substances 0.000 claims description 2
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 2
- LEVWYRKDKASIDU-IMJSIDKUSA-N L-cystine Chemical compound [O-]C(=O)[C@@H]([NH3+])CSSC[C@H]([NH3+])C([O-])=O LEVWYRKDKASIDU-IMJSIDKUSA-N 0.000 claims description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- ZWXPDGCFMMFNRW-UHFFFAOYSA-N N-methylcaprolactam Chemical compound CN1CCCCCC1=O ZWXPDGCFMMFNRW-UHFFFAOYSA-N 0.000 claims description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 2
- 239000004283 Sodium sorbate Substances 0.000 claims description 2
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 claims description 2
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 claims description 2
- 229910001863 barium hydroxide Inorganic materials 0.000 claims description 2
- UCVMQZHZWWEPRC-UHFFFAOYSA-L barium(2+);hydrogen carbonate Chemical compound [Ba+2].OC([O-])=O.OC([O-])=O UCVMQZHZWWEPRC-UHFFFAOYSA-L 0.000 claims description 2
- AYJRCSIUFZENHW-DEQYMQKBSA-L barium(2+);oxomethanediolate Chemical compound [Ba+2].[O-][14C]([O-])=O AYJRCSIUFZENHW-DEQYMQKBSA-L 0.000 claims description 2
- 229940050390 benzoate Drugs 0.000 claims description 2
- 239000011575 calcium Substances 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- NKWPZUCBCARRDP-UHFFFAOYSA-L calcium bicarbonate Chemical compound [Ca+2].OC([O-])=O.OC([O-])=O NKWPZUCBCARRDP-UHFFFAOYSA-L 0.000 claims description 2
- 229910000020 calcium bicarbonate Inorganic materials 0.000 claims description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 2
- 238000005119 centrifugation Methods 0.000 claims description 2
- 229910000420 cerium oxide Inorganic materials 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 229960003067 cystine Drugs 0.000 claims description 2
- JCCYXJAEFHYHPP-OLXYHTOASA-L dilithium;(2r,3r)-2,3-dihydroxybutanedioate Chemical compound [Li+].[Li+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O JCCYXJAEFHYHPP-OLXYHTOASA-L 0.000 claims description 2
- ZPJGNHUPXGDASP-UHFFFAOYSA-L dilithium;hexanedioate Chemical compound [Li+].[Li+].[O-]C(=O)CCCCC([O-])=O ZPJGNHUPXGDASP-UHFFFAOYSA-L 0.000 claims description 2
- YNQRWVCLAIUHHI-UHFFFAOYSA-L dilithium;oxalate Chemical compound [Li+].[Li+].[O-]C(=O)C([O-])=O YNQRWVCLAIUHHI-UHFFFAOYSA-L 0.000 claims description 2
- VIQSRHWJEKERKR-UHFFFAOYSA-L disodium;terephthalate Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=C(C([O-])=O)C=C1 VIQSRHWJEKERKR-UHFFFAOYSA-L 0.000 claims description 2
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 claims description 2
- DLFDEDJIVYYWTB-UHFFFAOYSA-N dodecyl(dimethyl)azanium;bromide Chemical compound Br.CCCCCCCCCCCCN(C)C DLFDEDJIVYYWTB-UHFFFAOYSA-N 0.000 claims description 2
- YXQMBBJITUIBDQ-UHFFFAOYSA-M dodecyl(triethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](CC)(CC)CC YXQMBBJITUIBDQ-UHFFFAOYSA-M 0.000 claims description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 2
- MGZTXXNFBIUONY-UHFFFAOYSA-N hydrogen peroxide;iron(2+);sulfuric acid Chemical compound [Fe+2].OO.OS(O)(=O)=O MGZTXXNFBIUONY-UHFFFAOYSA-N 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 2
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 229940031993 lithium benzoate Drugs 0.000 claims description 2
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 claims description 2
- 229910052808 lithium carbonate Inorganic materials 0.000 claims description 2
- 229910001386 lithium phosphate Inorganic materials 0.000 claims description 2
- WAHQBNXSPALNEA-UHFFFAOYSA-L lithium succinate Chemical compound [Li+].[Li+].[O-]C(=O)CCC([O-])=O WAHQBNXSPALNEA-UHFFFAOYSA-L 0.000 claims description 2
- 229960004254 lithium succinate Drugs 0.000 claims description 2
- LDJNSLOKTFFLSL-UHFFFAOYSA-M lithium;benzoate Chemical compound [Li+].[O-]C(=O)C1=CC=CC=C1 LDJNSLOKTFFLSL-UHFFFAOYSA-M 0.000 claims description 2
- HQRPHMAXFVUBJX-UHFFFAOYSA-M lithium;hydrogen carbonate Chemical compound [Li+].OC([O-])=O HQRPHMAXFVUBJX-UHFFFAOYSA-M 0.000 claims description 2
- QWDJLDTYWNBUKE-UHFFFAOYSA-L magnesium bicarbonate Chemical compound [Mg+2].OC([O-])=O.OC([O-])=O QWDJLDTYWNBUKE-UHFFFAOYSA-L 0.000 claims description 2
- 229910000022 magnesium bicarbonate Inorganic materials 0.000 claims description 2
- 235000014824 magnesium bicarbonate Nutrition 0.000 claims description 2
- 239000002370 magnesium bicarbonate Substances 0.000 claims description 2
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 claims description 2
- 239000001095 magnesium carbonate Substances 0.000 claims description 2
- 229910000021 magnesium carbonate Inorganic materials 0.000 claims description 2
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims description 2
- 239000000347 magnesium hydroxide Substances 0.000 claims description 2
- 229910001862 magnesium hydroxide Inorganic materials 0.000 claims description 2
- VGGNVBNNVSIGKG-UHFFFAOYSA-N n,n,2-trimethylaziridine-1-carboxamide Chemical compound CC1CN1C(=O)N(C)C VGGNVBNNVSIGKG-UHFFFAOYSA-N 0.000 claims description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 2
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 claims description 2
- SIWVEOZUMHYXCS-UHFFFAOYSA-N oxo(oxoyttriooxy)yttrium Chemical compound O=[Y]O[Y]=O SIWVEOZUMHYXCS-UHFFFAOYSA-N 0.000 claims description 2
- AVTYONGGKAJVTE-OLXYHTOASA-L potassium L-tartrate Chemical compound [K+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O AVTYONGGKAJVTE-OLXYHTOASA-L 0.000 claims description 2
- 235000011056 potassium acetate Nutrition 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- 235000011181 potassium carbonates Nutrition 0.000 claims description 2
- 239000004302 potassium sorbate Substances 0.000 claims description 2
- 235000010241 potassium sorbate Nutrition 0.000 claims description 2
- 229940069338 potassium sorbate Drugs 0.000 claims description 2
- 239000001472 potassium tartrate Substances 0.000 claims description 2
- 229940111695 potassium tartrate Drugs 0.000 claims description 2
- 235000011005 potassium tartrates Nutrition 0.000 claims description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
- 229940083542 sodium Drugs 0.000 claims description 2
- HELHAJAZNSDZJO-OLXYHTOASA-L sodium L-tartrate Chemical compound [Na+].[Na+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O HELHAJAZNSDZJO-OLXYHTOASA-L 0.000 claims description 2
- 239000001632 sodium acetate Substances 0.000 claims description 2
- 235000017281 sodium acetate Nutrition 0.000 claims description 2
- 239000000661 sodium alginate Substances 0.000 claims description 2
- 235000010413 sodium alginate Nutrition 0.000 claims description 2
- 229940005550 sodium alginate Drugs 0.000 claims description 2
- 239000004299 sodium benzoate Substances 0.000 claims description 2
- 235000010234 sodium benzoate Nutrition 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- 239000001509 sodium citrate Substances 0.000 claims description 2
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 claims description 2
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 claims description 2
- 239000000176 sodium gluconate Substances 0.000 claims description 2
- 235000012207 sodium gluconate Nutrition 0.000 claims description 2
- 229940005574 sodium gluconate Drugs 0.000 claims description 2
- OABYVIYXWMZFFJ-ZUHYDKSRSA-M sodium glycocholate Chemical compound [Na+].C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCC([O-])=O)C)[C@@]2(C)[C@@H](O)C1 OABYVIYXWMZFFJ-ZUHYDKSRSA-M 0.000 claims description 2
- 239000001540 sodium lactate Substances 0.000 claims description 2
- 235000011088 sodium lactate Nutrition 0.000 claims description 2
- 229940005581 sodium lactate Drugs 0.000 claims description 2
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 claims description 2
- ZNCPFRVNHGOPAG-UHFFFAOYSA-L sodium oxalate Chemical compound [Na+].[Na+].[O-]C(=O)C([O-])=O ZNCPFRVNHGOPAG-UHFFFAOYSA-L 0.000 claims description 2
- 229940039790 sodium oxalate Drugs 0.000 claims description 2
- 239000001488 sodium phosphate Substances 0.000 claims description 2
- 229910000162 sodium phosphate Inorganic materials 0.000 claims description 2
- LROWVYNUWKVTCU-STWYSWDKSA-M sodium sorbate Chemical compound [Na+].C\C=C\C=C\C([O-])=O LROWVYNUWKVTCU-STWYSWDKSA-M 0.000 claims description 2
- 235000019250 sodium sorbate Nutrition 0.000 claims description 2
- ZDQYSKICYIVCPN-UHFFFAOYSA-L sodium succinate (anhydrous) Chemical compound [Na+].[Na+].[O-]C(=O)CCC([O-])=O ZDQYSKICYIVCPN-UHFFFAOYSA-L 0.000 claims description 2
- 239000001433 sodium tartrate Substances 0.000 claims description 2
- 229960002167 sodium tartrate Drugs 0.000 claims description 2
- 235000011004 sodium tartrates Nutrition 0.000 claims description 2
- KSVSZLXDULFGDQ-UHFFFAOYSA-M sodium;4-aminobenzenesulfonate Chemical compound [Na+].NC1=CC=C(S([O-])(=O)=O)C=C1 KSVSZLXDULFGDQ-UHFFFAOYSA-M 0.000 claims description 2
- KVCGISUBCHHTDD-UHFFFAOYSA-M sodium;4-methylbenzenesulfonate Chemical compound [Na+].CC1=CC=C(S([O-])(=O)=O)C=C1 KVCGISUBCHHTDD-UHFFFAOYSA-M 0.000 claims description 2
- CLUHWBURHNNGPK-UHFFFAOYSA-M sodium;6-aminohexanoate Chemical compound [Na+].NCCCCCC([O-])=O CLUHWBURHNNGPK-UHFFFAOYSA-M 0.000 claims description 2
- NMTDPTPUELYEPL-UHFFFAOYSA-M sodium;heptanoate Chemical compound [Na+].CCCCCCC([O-])=O NMTDPTPUELYEPL-UHFFFAOYSA-M 0.000 claims description 2
- ASYWCBYOOVDHBB-UHFFFAOYSA-J tetralithium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Li+].[Li+].[Li+].[Li+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O ASYWCBYOOVDHBB-UHFFFAOYSA-J 0.000 claims description 2
- JZBRFIUYUGTUGG-UHFFFAOYSA-J tetrapotassium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [K+].[K+].[K+].[K+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O JZBRFIUYUGTUGG-UHFFFAOYSA-J 0.000 claims description 2
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 claims description 2
- 239000004408 titanium dioxide Substances 0.000 claims description 2
- TWQULNDIKKJZPH-UHFFFAOYSA-K trilithium;phosphate Chemical compound [Li+].[Li+].[Li+].[O-]P([O-])([O-])=O TWQULNDIKKJZPH-UHFFFAOYSA-K 0.000 claims description 2
- FYZXEMANQYHCFX-UHFFFAOYSA-K tripotassium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxymethyl)amino]acetate Chemical compound [K+].[K+].[K+].OC(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O FYZXEMANQYHCFX-UHFFFAOYSA-K 0.000 claims description 2
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 claims description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 1
- 230000008569 process Effects 0.000 abstract description 9
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 239000002131 composite material Substances 0.000 abstract description 2
- 229920000642 polymer Polymers 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 229920001169 thermoplastic Polymers 0.000 abstract description 2
- 239000004416 thermosoftening plastic Substances 0.000 abstract description 2
- 230000006978 adaptation Effects 0.000 abstract 1
- 238000001914 filtration Methods 0.000 description 12
- 239000004734 Polyphenylene sulfide Substances 0.000 description 9
- 229920000069 polyphenylene sulfide Polymers 0.000 description 9
- 239000006227 byproduct Substances 0.000 description 6
- 238000002329 infrared spectrum Methods 0.000 description 4
- 239000012066 reaction slurry Substances 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 238000006068 polycondensation reaction Methods 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229910052979 sodium sulfide Inorganic materials 0.000 description 2
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical group C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 description 1
- OKISUZLXOYGIFP-UHFFFAOYSA-N 4,4'-dichlorobenzophenone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=C(Cl)C=C1 OKISUZLXOYGIFP-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000009388 chemical precipitation Methods 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000002920 hazardous waste Substances 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229940035429 isobutyl alcohol Drugs 0.000 description 1
- 239000010808 liquid waste Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000012434 nucleophilic reagent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000110 poly(aryl ether sulfone) Polymers 0.000 description 1
- 229920001955 polyphenylene ether Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 239000002910 solid waste Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000004763 sulfides Chemical class 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
- C08G75/0204—Polyarylenethioethers
- C08G75/025—Preparatory processes
- C08G75/0259—Preparatory processes metal hydrogensulfides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
- C08G75/0204—Polyarylenethioethers
- C08G75/0227—Polyarylenethioethers derived from monomers containing two or more aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
- C08G75/0204—Polyarylenethioethers
- C08G75/025—Preparatory processes
- C08G75/0254—Preparatory processes using metal sulfides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
- C08G75/0204—Polyarylenethioethers
- C08G75/0277—Post-polymerisation treatment
- C08G75/0281—Recovery or purification
Definitions
- the invention relates to a polyarylether with high whiteness and low impurity content and a preparation method thereof, belonging to the field of polymer synthesis.
- the main production method of polyarylether is: using auxiliary agents, nucleophilic reagents (such as sulfides), dihalogenated aromatic compounds and polar solvents as raw materials, carrying out solution polycondensation, separating the reaction mixture into solid and liquid after the reaction, and purifying the crude resin product by washing with water.
- the process flow is long and the amount of water used in this process is large.
- the subsequent solvent is generally recovered by distillation separation, which leads to high energy consumption in the subsequent solvent recovery process and low purity of the recovered solvent.
- the solvent and volatile content contained in the resin are high, and the resin is impure, which makes the resin dark in color, produces bubbles or defects after being processed into products, affecting the comprehensive performance of the final product.
- Sodium chloride electrolysis After the treatment in step 4), a qualified sodium chloride aqueous solution is obtained, which is placed in an electrolytic cell and converted into sodium hydroxide, chlorine and hydrogen under the action of an electrolytic catalyst; the sodium hydroxide is sold as caustic soda or used in the front-end polymerization reaction of polyarylether resin, the chlorine is used to produce the raw materials p-dichlorobenzene or 4,4'-dichlorodiphenyl sulfone in the production of polyarylether (such as typical resins such as polyphenylene sulfide, polyarylether sulfone, etc.), and the hydrogen is recycled as a clean energy;
- polyarylether such as typical resins such as polyphenylene sulfide, polyarylether sulfone, etc.
- the method of step 1) is: adding the sulfide, the auxiliary agent and the solvent into a reaction kettle, and carrying out a dehydration reaction at a temperature of 140 to 230° C. for 0.5 to 3 hours under nitrogen protection to obtain a dehydrated reaction solution, and the removed solvent-containing mixed liquid is sent to a dehydration condensate tank for combined centralized treatment; when the temperature of the above reaction solution drops to 80 to 180° C., adding a dichloro aromatic compound, reacting at a temperature of 150 to 230° C. for 0.5 to 8 hours, and then maintaining at a temperature of 230 to 280° C. for 0.5 to 10 hours to obtain a reaction product mixed liquid.
- the structural formula of the dihalogenated aromatic compound is Cl-Ar-Cl, wherein:
- the solvent is at least one of formamide, acetamide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, N,N-dimethylpropylene urea, 1,3-dimethyl-2-imidazolidinone, N-cyclohexylpyrrolidone, hexamethylphosphoric triamide, cyclopentane, diphenyl sulfone, ⁇ -caprolactam, dimethyl sulfoxide, dimethyl sulfone, quinoline, isoquinoline, 2,4-dimethylcyclopentane or N-methylcaprolactam; or the solvent is a high-purity solvent with a purity of ⁇ 99% recovered in step 3) of the preparation method.
- the auxiliary agent is lithium hydroxide, sodium hydroxide, potassium hydroxide, magnesium hydroxide, Calcium, barium hydroxide, aluminum hydroxide, lithium carbonate, sodium carbonate, potassium carbonate, magnesium carbonate, calcium carbonate, barium carbonate, lithium bicarbonate, sodium bicarbonate, potassium bicarbonate, magnesium bicarbonate, calcium bicarbonate, barium bicarbonate, lithium acetate, sodium acetate, potassium acetate, lithium benzoate, sodium benzoate, lithium ethylenediaminetetraacetate, sodium ethylenediaminetetraacetate, trisodium ethylenediaminetetraacetate, potassium ethylenediaminetetraacetate, tripotassium ethylenediaminetetraacetate, sodium dodecylbenzenesulfonate, sodium p-toluene benzoate, lithium p-toluene benzoate, sodium terephthalate, sodium terephthalate, sodium p-toluen
- the extractant is any one of chloroform, dichloromethane, tetrachloroethane, carbon tetrachloride, cyclohexane, ethyl acetate, butyl acetate or isopropyl ether.
- step 4) of the above method the method of using an auxiliary agent extracting agent to recover and separate the auxiliary agent is as follows: 100 parts of the crude solid resin product obtained in step 3) and 300-3000 parts of the auxiliary agent extracting agent are added to an auxiliary agent extractor for continuous spray countercurrent transmission extraction, the rotation speed of the extractor is 2-30 r/min, the extraction temperature is 20-80° C., and the extraction time is 1-60 min; the resin after extraction is discharged from the upper outlet of the extractor into a centrifuge for solid-liquid separation, and the liquid extracting agent is sent to a feed buffer tank of a multiple-effect evaporator; the liquid part after extraction overflows from the lower outlet of the extractor and is also sent to the feed buffer tank of the multiple-effect evaporator, and then sent to the multiple-effect evaporator for evaporation at 40-90° C. and a vacuum degree of 0.04-0.09 MPa, the liquid after multiple-effect evaporation is recovered and used directly as the next
- the auxiliary leaching agent is at least one of methanol, ethanol, propanol, ethylene glycol, propylene glycol, glycerol, isopropanol, isobutanol, tert-butanol, n-butanol, n-pentanol, isopentanol, n-hexanol, n-heptanol, n-octanol, isooctyl alcohol, acetone, butanone, cyclopentanone, cyclohexanone, chloroform, dichloromethane, tetrachloroethane or carbon tetrachloride.
- the washing water oxidant is at least one of hydrogen peroxide, ozone, Fenton's reagent or ferric chloride.
- the whiteness of the polyarylether is ⁇ 85.
- the impurity content of the polyarylether is ⁇ 12ppm.
- the purity of the polyarylether is ⁇ 99.9%.
- the purity and whiteness of the obtained resin are greatly improved compared with the traditional process, with a whiteness of ⁇ 85; the impurity content (including volatile components and ash) is ⁇ 12ppm; it is more conducive to the purification of the product and to adapt to the application requirements of subsequent high-end fields.
- a high-grade resin it fills the domestic gap and is used to prepare high-quality parts such as special materials for thermoplastic composite materials for large aircraft, special materials for radar and some parts of stealth aircraft, etc., so as to reduce costs and improve efficiency.
- the present invention can directly use high-temperature filtration solvent or extraction recovery solvent as the reaction solvent, without the need for subsequent dehydration and other refining processes, and the process flow is short; and in the extraction process, extraction and separation are combined into one, the operation is flexible and easy to control, the extractant is an organic matter with small specific heat and low boiling point, the recovery rate is high, the energy consumption is low, and the cost is saved.
- FIG. 1 is an infrared spectrum of the polyphenylene sulfide resin obtained in Example 1.
- FIG. 2 is an infrared spectrum of the polyphenylene sulfide ketone resin obtained in Example 2.
- the invention discloses a resource-recyclable high-purity polyarylether and a preparation method thereof.
- the invention is characterized in that sulfide and dichloro aromatic compound are used as raw materials, and the resin is purified and the solvent is recovered through a solution polycondensation reaction and a subsequent extraction process, and an organic solvent is leached to recover the auxiliary agent; ultrapure polyarylether (purity ⁇ 99.99%) is obtained, the whiteness of the obtained polyarylether resin is ⁇ 85, and the impurity content (including volatile matter and ash) is ⁇ 12ppm; and the entire preparation process realizes the complete recycling of solvents, auxiliary agents and by-product salts, which is green, environmentally friendly, and reduces costs and improves efficiency.
- auxiliary agent 400-6000 parts of solvent and 56-360 parts of sulfide are added into a reaction kettle, and dehydrated at 140-230°C for 0.5-3h under nitrogen protection to obtain a dehydrated reaction solution.
- temperature of the solution drops to 80-180°C
- 114-600 parts of dichloro aromatic compound are added, and the reaction is carried out at 150-230°C for 0.5-8h, and then the temperature is maintained at 230-280°C for 0.5-10h, and the temperature is lowered to 150-220°C, and high-temperature filtration is performed to recover part of the solvent in the reaction slurry.
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyethers (AREA)
Abstract
本发明涉及一种高白度低杂质含量的聚芳醚及其制备方法,属于高分子合成领域。本发明提供一种高白度低杂质含量聚芳醚的制备方法,所述制备方法包括如下步骤:1)脱水反应;2)第一次回收溶剂;3)萃取法回收溶剂及树脂纯化;4)助剂回收、树脂洗涤及洗水提纯;5)氯化钠电解。利用本发明方法,能够使得所得树脂纯度及白度相对传统工艺得到极大的提升,白度≥85;杂质含量(包括挥发份、灰分)≤12ppm;更利于产品的纯化及适应后续高端领域的应用要求,作为高品级树脂填补国内空白,用于制备高品质制件如大飞机专用热塑性复合材料专用料、雷达、隐形飞机部分零部件专用料等,做到降本提效。
Description
本发明涉及一种高白度低杂质含量的聚芳醚及其制备方法,属于高分子合成领域。
聚芳醚主要包括如聚苯硫醚、聚苯硫醚酯、聚苯硫醚酮、聚苯硫醚砜、聚苯硫醚酰胺、聚苯醚硫醚、聚苯硫醚酰亚胺,由于其耐腐蚀、高温以及优良的电性能、机械性能和尺寸稳定性,被广泛用于航天航空和电子技术方面。
其中,聚芳醚的主要生产方法为:采用助剂、亲核试剂(如硫化物)、二卤代芳香化合物和极性溶剂为原料,进行溶液缩聚,反应后对反应混合液进行固液分离,树脂粗产品采用水洗的方法进行纯化,工艺流程长,且此过程中的用水量大,而后续溶剂一般采用精馏分离的方式回收,从而导致后续溶剂回收过程中能耗高,且回收溶剂的纯度不高;树脂中包裹的溶剂、挥发份高,树脂不纯,进而使得树脂加工成产品后颜色深、产生泡孔或缺陷,影响最终制件的综合性能。此外,所涉及到的助剂分离、回收也是在水溶液中进行,使得其回收过程能耗高,纯度不高,且一般需进行化学沉淀法回收分离后,再进行额外第二步的反应才能得到最终的反应所需助剂,整个过程流程长,设备投入多,而导致聚芳醚类产品长期以来生产成本居高不下;更重要的是其废水、废渣往往不易完全分离开,如副产NaCl由于含有大量的氨氮和有机物,而无法进行后续循环利用,导致产生大量危废,成本高,且环境压力大,不利于大规模工业生产。
发明内容
针对上述缺陷,本发明提供一种资源可循环的高白度低杂质含量的聚芳醚的制备方法,其特点是采用硫化物与二氯代芳香化合物为原料,通过溶液缩聚反应及高温过滤、萃取工艺进行纯化及溶剂回收、有机溶剂浸取回收助剂制备得到了资源可循环的高纯度高白度低杂质含量的聚芳醚;此外,通过上述一系列纯化方法,所得含盐废水经深度氧化处理能够实现脱除有机物及氨氮,进而在电解催化剂的作用下进行电解,制得的烧碱、氯气进入前置聚合反应及二氯代单体的制备,氢气作为清洁能源循环使用,从而实现了资源完全循环,产品提质提效。
本发明的技术方案:
本发明要解决的技术问题是提供一种高白度低杂质含量聚芳醚的制备方法,所述制备方法包括如下步骤:
1)脱水反应:将硫化物、助剂和溶剂加入反应釜中,氮气或惰性气体保护下,脱水反应得到脱水后的反应溶液,脱除的含溶剂混合液体送入脱水冷凝液罐合并集中处理;脱水后的反应溶液降温后与二氯代芳香化合物反应得反应产物混合液;
2)第一次回收溶剂:步骤1)所得反应产物混合液于150~220℃下通过高温过滤,回收反应产物混合液中的部分溶剂,将回收的溶剂输送至溶剂回收槽,直接用于下一批次物料聚合;
3)萃取法回收溶剂及树脂纯化:将步骤2)过滤后物料降温至10~160℃送至萃取釜,分批次加入萃取剂,密闭条件下于温度10~160℃、压力0~1MPa下分批次萃取剩余溶剂;萃取后的混合溶液经过滤后送入富萃取剂混合液槽,并将其按比例与步骤1)中的含溶剂混合液进行混合,再经离心萃取或逆流塔式萃取;然后分别将含溶剂和萃取剂的混合液送至溶剂/萃取剂槽,水送至洗水槽;并将含溶剂和萃取剂的混合液进行精馏分离,分别回收萃取剂和溶剂,循环利用;
4)助剂回收、树脂洗涤及洗水提纯:经步骤3)处理后得到的固体树脂粗产品采用助剂浸取剂进行助剂的回收和分离;浸取完成后的液体进行多效蒸发,液体回收作为下一批助剂浸取剂使用,固体则为回收的助剂,无需后处理可直接使用;浸取完成后的固体树脂粗产品采用脱盐水或上一批次产品的洗水进行逆流水洗和固液分离,分离后的含水聚芳醚树脂通过真空干燥获得高白度低杂质含量的聚芳醚;而洗水则送至洗水槽与步骤3)中萃取分离水合并再加入氧化剂进行氧化处理,去除洗水中的有机物及氨氮杂质,使其达到电解的工况要求;
5)氯化钠电解:经步骤4)处理后得到合格的氯化钠水溶液,置于电解槽内,在电解催化剂的作用下,转化生成氢氧化钠、氯气及氢气;氢氧化钠作为烧碱出售或用于聚芳醚树脂的前端聚合反应,氯气用于生产聚芳醚中(如典型树脂如聚苯硫醚、聚芳硫醚砜等)的生产用原料对二氯苯或4,4’-二氯二苯砜,氢气作为清洁能源循环使用;
其中,各原料由以下重量份的组分组成:
进一步,上述制备方法中,步骤1)的方法为:将硫化物、助剂和溶剂加入反应釜中,氮气保护下,于温度140~230℃脱水反应0.5~3h,得到脱水后的反应溶液,脱除的含溶剂混合液体送入脱水冷凝液罐合并集中处理;待上述反应溶液温度降至80~180℃时,加入二氯代芳香化合物,于温度150~230℃下反应0.5~8h,再在温度230~280℃保持0.5~10h,得到反应产物混合液。
进一步,所述硫化物选自下述化合物:
Na2S或NaHS中的任一种;
所述二卤代芳香化合物的结构式为Cl-Ar-Cl,其中,
中的至少一种,其中,m=2、4、6、8或10。
进一步,步骤1)中,所述溶剂为甲酰胺、乙酰胺、N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基吡咯烷酮、N,N-二甲基丙烯基脲、1,3-二甲基-2-咪唑啉酮、N-环己基吡咯烷酮、六甲基磷酰三胺、环丁砜、二苯砜、ε-己内酰胺、二甲基亚砜、二甲基砜、喹啉、异喹啉、2,4-二甲基环丁砜或N-甲基己内酰胺中的至少一种;或所述溶剂为制备方法中步骤3)回收的纯度≥99%的高纯度溶剂。
进一步,步骤1)中,所述助剂为氢氧化锂、氢氧化钠、氢氧化钾、氢氧化镁、氢氧化
钙、氢氧化钡、氢氧化铝、碳酸锂、碳酸钠、碳酸钾、碳酸镁、碳酸钙、碳酸钡、碳酸氢锂、碳酸氢钠、碳酸氢钾、碳酸氢镁、碳酸氢钙、碳酸氢钡、乙酸锂、乙酸钠、乙酸钾、苯甲酸锂、苯甲酸钠、乙二胺四乙酸锂、乙二胺四乙酸钠、乙二胺四乙酸三钠、乙二胺四乙酸钾、乙二胺四乙酸三钾、十二烷基苯磺酸钠、对甲基苯甲酸钠、对甲基苯甲酸锂、对苯二甲酸钠、对苯二甲酸钠、对甲基苯磺酸钠、对氨基苯磺酸钠、草酸钠、草酸锂、丁二酸钠、丁二酸锂、己二酸钠、己二酸锂、氯化锂、磷酸钠、磷酸锂、酒石酸钠、酒石酸锂、酒石酸钾、海藻酸钠、葡萄糖酸钠、乳酸钠、山梨酸钠、山梨酸钾、赖氨酸钠、赖氨酸钾、胱氨酸钠、6-氨基己酸钠、庚糖酸钠、月桂酸钠、柠檬酸钠、甘胆酸钠、二辛基琥珀酸钠、乙二胺四甲叉磷酸钠、二乙烯三胺五甲叉膦酸钠、胺三甲叉磷酸钠、十二烷基三乙基氯化铵、十二烷基二甲基溴化铵或硬脂酸钠中的至少一种;
进一步,上述制备方法的步骤3)中,萃取后的混合溶液与步骤1)中的含溶剂混合液的体积比为:1~5份:1~3份。
进一步,步骤3)中,所述萃取剂为三氯甲烷、二氯甲烷、四氯乙烷、四氯化碳、环己烷、乙酸乙酯、乙酸丁酯或异丙醚中的任一种。
进一步,步骤3)中,分批次指分1~5批次。
进一步,上述方法的步骤4)中,采用助剂浸取剂进行助剂的回收和分离的方法为:将步骤3)得到的固体树脂粗产品100份、300~3000份助剂浸取剂加入助剂浸取器中进行连续喷雾逆流传输浸取,浸取器的转速为2~30r/min,浸取温度为20~80℃,浸取时间为1~60min;浸取后的树脂从浸取器的上口出料进入离心机进行固液分离,液体浸取剂送至多效蒸发器进料缓冲槽;浸取后的液体部分从浸取器的下口溢流出,也送至多效蒸发器进料缓冲槽,再将其送入多效蒸发器于40~90℃,真空度0.04~0.09MPa进行蒸发,多效蒸发后的液体回收作为下一批助剂浸取剂直接使用,多效蒸发后的固体则回收作为助剂直接使用。
进一步,上述方法的步骤4)中,浸取完成后的固体树脂粗产品采用3~5次、每次300~1000份脱盐水或上一批次产品的洗水进行逆流水洗、固液分离,以去除产物中包裹的盐和极少量助剂,分离后的含水聚芳醚树脂在温度80~120℃、真空度0.03~0.095MPa干燥1~12h,获得资源可循环高纯度聚芳醚树脂;而洗水则送至洗水槽与步骤3)中萃取分离水合并在氧化剂的作用下进行室温~60℃氧化处理,去除洗水中的有机物及氨氮杂质,达到电解纯度要求。
进一步,上述方法中的步骤4)中,所述助剂浸取剂为甲醇、乙醇、丙醇、乙二醇、丙二醇、丙三醇、异丙醇、异丁醇、叔丁醇、正丁醇、正戊醇、异戊醇、正己醇、正庚醇、正辛醇、异辛醇、丙酮、丁酮、环戊酮、环己酮、三氯甲烷、二氯甲烷、四氯乙烷或四氯化碳中的至少一种。
进一步,上述方法中的步骤5)中,所述洗水氧化剂为双氧水、臭氧、芬顿试剂或氯化铁中的至少一种。
进一步,上述方法中的步骤5)中,所述氯化钠水溶液电解催化剂为氧化钌、氧化钇、氧化铈、氧化镧、二氧化钛或氧化铱中的至少一种。
本发明要解决的第二个技术问题是提供一种聚芳醚,其采用上述方法制得。
进一步,所述聚芳醚的白度≥85。
进一步,所述聚芳醚的杂质含量≤12ppm。
进一步,所述聚芳醚的纯度≥99.9%。
本发明中,所述原料份数除特殊说明外,均为重量份数。
本发明的有益效果:
1、本发明聚芳醚树脂制备过程中采用特定的萃取剂和萃取方式对过滤溶剂后的树脂进行萃取纯化,一举两用,既可以把树脂中包裹的溶剂回收回来,提升溶剂的回收率;同时有效地防止了树脂粗产品中所包裹的热敏性物质如溶剂的氧化和逸散,且利用萃取剂与溶剂和树脂分子达到分子级别的交换,可以将树脂中包裹的挥发份充分洗脱、置换出来;从而使得所得树脂纯度及白度相对传统工艺得到极大的提升,白度≥85;杂质含量(包括挥发份、灰分)≤12ppm;更利于产品的纯化及适应后续高端领域的应用要求,作为高品级树脂填补国内空白,用于制备高品质制件如大飞机专用热塑性复合材料专用料、雷达、隐形飞机部分零部件专用料等,做到降本提效。
2、本发明树脂经萃取剂萃取过程中,其助剂也一并得以纯化,使得后续助剂的回收工艺更为简化,助剂的回收率高且回收的助剂纯度高达99.5%,可不经任何处理直接回用。
3、本发明可直接使用高温过滤溶剂或萃取回收溶剂作为反应用溶剂,无需进行后续脱水等精制过程,工艺流程短;且萃取过程中萃取和分离合二为一,操作弹性大,易于控制,萃取剂为比热小、沸点低的有机物,回收率高,能耗低,节约成本。
4、本发明相对于传统聚芳醚制备工艺,后续废液及固废的功能清晰、组分均相互分离并深度纯化处理,各副产组分分离彻底、纯度高,尤其是副产NaCl,脱除氨氮和有机物的工艺,通过电解的方法几乎完全回收循环再利用,三废排放量极低,环保压力小;这是现有技术中生产。
图1为实施例1所得聚苯硫醚树脂的红外光谱图。
图2为实施例2所得聚苯硫醚酮树脂的红外光谱图。
本发明公开了一种资源可循环高纯度聚芳醚及其制备方法,其特点是采用硫化物与二氯代芳香化合物为原料,通过溶液缩聚反应及后续萃取工艺对树脂进行纯化及溶剂回收、有机溶剂浸取回收助剂的方法;得到超纯聚芳醚(纯度≥99.99%),所得聚芳醚树脂白度≥85,杂质含量(包括挥发份、灰分)≤12ppm;并且整个制备过程实现了溶剂、助剂及副产盐的彻底循环使用,绿色环保,降本提效。
本发明资源可循环高纯度聚芳醚可采用下述具体实施方式制得:
将0.1~500份助剂,400~6000份溶剂和56~360份硫化物加入反应釜中,在氮气保护下,于温度140~230℃脱水反应0.5~3h,得到脱水后的反应溶液,待上述溶液温度降至80~180℃时,加入114~600份二氯代芳香化合物,在温度150~230℃反应0.5~8h,再在温度230~280℃保持0.5~10h,降温至150~220℃,进行高温过滤,回收反应浆液中的部分溶剂,并输送至溶剂回收槽;过滤后物料降温至10~160℃送至萃取釜,分批加入萃取剂密闭条件下于温度10~160℃、压力0~1MPa下经1-5次萃取剩余溶剂;萃取后的混合溶液经过滤后送入富萃取剂混合液槽,并将其按体积比例1~5份:与步骤1)中的含溶剂混合液1~3份进行混合离心萃取或逆流塔式萃取,分别将含溶剂和萃取剂的混合液送至溶剂/萃取剂槽,水送至洗水槽;并将含溶剂和萃取剂的混合液进行精馏分离,分别回收萃取剂和溶剂,循环利用;经过滤、萃取后的固体树脂粗产品(主要为盐和助剂,几乎不含溶剂)采用300~3000份助剂浸取剂进行助剂回收及分离,浸取完后的液体进行多效蒸发,液体回收作为下一批料助剂浸取剂使用,固体则为回收的助剂,无需后处理可直接使用;浸取完后的固体树脂粗产品采用3~5次、每次300~1000份脱盐水或上一批次产品的洗水进行逆流水洗、固液分离,以去除产物中包裹的盐和极少量助剂,分离后的含水聚芳醚树脂在温度80~120℃、真空度0.03~0.095MPa干燥1~12h,获得纯化聚芳醚树脂,所得树脂白度≥85,杂质含量(包括挥发份、灰分)≤12ppm;而洗水则送至洗水槽与步骤3)中萃取分离水合并在氧化剂的作用下进行室温~60℃氧化处理,去除洗水中的有机物及氨氮杂质,在电解槽内及电解催化剂的作用下,高效转化,生成氢氧化钠、氯气及氢气。
现有公开的聚芳醚树脂及其制备方法的专利申请或专利中,都存在白度较低、或纯度较低、或杂质含量较高、或溶剂回收率较低、或助剂与溶剂的回收一很难区分开等缺陷,如“申请号为2013104328307、发明名称为一种聚芳硫醚及其制备方法”的发明中,所得聚芳硫醚树脂的白度只有60~70,杂质含量(包括挥发份、灰分)为200~2000ppm;“申请号为2013106908646、发明名称为一种高纯度自催化聚芳硫醚及其制备方法”的发明中,溶剂回收率最高只有94%,所得聚芳硫醚树脂白度为70,杂质含量(包括挥发份、灰分)为150ppm;“申请号为“2016103482486、发明名称为一种环保经济型聚芳醚及其制备方法”的发明中,其
制备过程中必须对富集溶剂后的洗水采用萃取-精馏法再进一步回收溶剂,并且所得聚芳硫醚树脂的白度只有55~70,杂质含量为200~300ppm;申请号为“2016105274115、发明名称为一种粒度分布窄的高白度聚芳硫醚及其制备方法”的发明中,所得聚芳硫醚树脂的杂质含量为200~400ppm,溶剂回收率最高为85~90%;并且上述公开的申请中均未实现聚芳醚树脂制备过程中将助剂与溶剂的回收区分开来并且达到助剂回收率和回收助剂纯度、溶剂回收率和回收溶剂纯度均很高的效果。
本发明首次将萃取及催化电解技术同时引入聚芳醚树脂的制备过程中,并且采用“通过高温过滤的方式回收部分溶剂——萃取回收剩余溶剂——回收助剂纯化树脂——副产氯化钠催化电解循环利用”的工艺,得到了高纯度(纯度≥99.99%)高白度(白度≥85)的高品质聚芳醚树脂,最终杂质含量极低(杂质含量(包括挥发份、灰分)≤12ppm);并且整个制备过程中溶剂回收率、助剂回收率均较高,回收得到的溶剂、助剂及萃取剂纯度也均较高,同时实现了副产氯化钠的高值循环利用,有助于聚芳醚产业的大规模、高质量发展。
下面通过实施例对本发明进行具体的描述,有必要在此指出的是本实施例只用于对本发明进行进一步说明,不能理解为对本发明保护范围的限制,该领域的技术熟练人员可以根据上述本发明的内容作出一些非本质的改进和调整。
实施例1
将50kg氢氧化钠、60kg乙酸锂,800kg 1,3-二甲基-2-咪唑啉酮和117.5kg含水硫氢化钠,在氮气保护下,于温度210℃脱水反应0.5h,得到脱水后的反应溶液,待上述溶液温度降至170℃时,加入147kg对二氯苯,在温度230℃反应1h,再在温度260℃保持6h,降温至200℃,进行一次高温过滤,回收反应浆液中的部分溶剂,并输送至溶剂回收槽;过滤后物料降温至160℃送至萃取釜,分批加入萃取剂乙酸乙酯500kg,密闭条件下于温度30℃、常压下经5次萃取剩余溶剂;萃取后的混合溶液经过滤后送入富萃取剂混合液槽,并将其按体积比例5:1与步骤1)中的含溶剂混合液进行混合离心萃取,分别将含溶剂和萃取剂的混合液送至溶剂/萃取剂槽,水送至洗水槽;并将含溶剂和萃取剂的混合液进行精馏分离,分别回收萃取剂和溶剂,循环利用;将上述萃取过滤后的含助剂固体树脂粗产品100kg、800kg异丙醇加入助剂浸取器中进行连续喷雾逆流传输浸取,浸取器的转速为6r/min,浸取温度为50℃,浸取时间为10min,浸取后的树脂从浸取器的上口出料进入离心机进行固液分离,液体浸取剂送至多效蒸发器进料缓冲槽;浸取后的液体部分从浸取器的下口溢流出,也送至多效蒸发器进料缓冲槽,再将其送入多效蒸发器于90℃,真空度0.06MPa进行蒸发,分别回收纯净的固体助剂及液体助剂浸取剂,无需后处理可直接循环使用;浸取完后的固体树脂粗产品采用5次、每次400kg脱盐水或上一批次产品的洗水进行逆流水洗、固液分离,以去除产物中包裹的盐和
极少量助剂,分离后的含水聚芳醚树脂在温度120℃、真空度0.06MPa干燥10h,获得纯化聚芳醚树脂,其产率为97.4%,特性粘数[η]=0.39(粘度测试溶剂为1-氯代萘),溶剂回收率为99.6%,助剂回收率为99.2%,红外光谱测试结果如图1所示。所得聚芳醚树脂的纯度为99.99%,白度为86,杂质含量为12ppm;而洗水则送至洗水槽与萃取分离水合并在10kg氧化剂双氧水的作用下进行60℃氧化处理,去除洗水中的有机物及氨氮杂质,在电解槽内及电解催化剂氧化钌的作用下,进行高效转化,生成氢氧化钠、氯气及氢气,氢氧化钠用于聚合脱水工段,氯气用于制备二卤代芳香单体,氢气作为清洁能源循环使用。
实施例2
将2kg氢氧化钠、42kg月桂酸钠,2500kg环丁砜和N-甲基吡咯烷酮(1:2)和180kg含水硫化钠,在氮气保护下,于温度200℃脱水反应3h,得到脱水后的反应溶液,待上述溶液温度降至120℃时,加入252kg 4,4’-二氯二苯甲酮,在温度210℃反应0.5h,再在温度260℃保持6h,降温至215℃,进行一次高温过滤,回收反应浆液中的部分溶剂,并输送至溶剂回收槽;过滤后物料降温至10℃送至萃取釜,分批加入萃取剂三氯甲烷400kg,密闭条件下于温度20℃、常压下经4次萃取剩余溶剂;萃取后的混合溶液经过滤后送入富萃取剂混合液槽,并将其按体积比例4:3与步骤1)中的含溶剂混合液进行混合离心萃取,分别将含溶剂和萃取剂的混合液送至溶剂/萃取剂槽,水送至洗水槽;并将含溶剂和萃取剂的混合液进行精馏分离,分别回收萃取剂和溶剂,循环利用;将上述萃取过滤后的含助剂固体树脂粗产品100kg、1800kg三氯甲烷加入助剂浸取器中进行连续喷雾逆流传输浸取,浸取器的转速为8r/min,浸取温度为20℃,浸取时间为10min,浸取后的树脂从浸取器的上口出料进入离心机进行固液分离,液体浸取剂送至多效蒸发器进料缓冲槽;浸取后的液体部分从浸取器的下口溢流出,也送至多效蒸发器进料缓冲槽,再将其送入多效蒸发器于40℃,真空度0.06MPa进行蒸发,分别回收纯净的固体助剂及液体助剂浸取剂,无需后处理可直接循环使用;浸取完后的固体树脂粗产品采用5次、每次400kg脱盐水或上一批次产品的洗水进行逆流水洗、固液分离,以去除产物中包裹的盐和极少量助剂,分离后的含水聚芳醚树脂在温度120℃、真空度0.08MPa干燥10h,获得纯化聚芳醚树脂,其产率为95.8%,特性粘数[η]=0.84(粘度测试溶剂为浓硫酸),溶剂回收率为99.7%,助剂回收率为99.3%,红外光谱测试结果如图2所示。所得聚芳醚树脂的纯度为99.99%,白度为85,杂质含量为11ppm;而洗水则送至洗水槽与萃取分离水合并在2kg臭氧+18kg双氧水的作用下进行50℃氧化处理,去除洗水中的有机物及氨氮杂质,在电解槽内及电解催化剂氧化铱的作用下,进行高效转化,生成氢氧化钠、氯气及氢气,氢氧化钠用于聚合脱水工段,氯气用于制备二卤代芳香单体,氢气作为清洁能源循环使用。
实施例3
将200kg碳酸氢钾、80kg己二酸钠,2000kg N-环己基吡咯烷酮和127kg含水硫氢化钠,在氮气保护下,于温度180℃脱水反应3h,得到脱水后的反应溶液,待上述溶液温度降至160℃时,加入287kg 4,4’-二氯二苯砜,在温度190℃反应6h,再在温度230℃保持6h,降温至210℃,进行一次高温过滤,回收反应浆液中的部分溶剂,并输送至溶剂回收槽;过滤后物料继续降温至30℃送至萃取釜,分批加入萃取剂乙酸丁酯400kg,密闭条件下于温度20℃、常压下经4次萃取剩余溶剂;萃取后的混合溶液经过滤后送入富萃取剂混合液槽,并将其按体积比例3:2与步骤1)中的含溶剂混合液进行混合离心萃取,分别将含溶剂和萃取剂的混合液送至溶剂/萃取剂槽,水送至洗水槽;并将含溶剂和萃取剂的混合液进行精馏分离,分别回收萃取剂和溶剂,循环利用;将上述萃取过滤后的含助剂固体树脂粗产品100kg、1200kg异丁醇加入助剂浸取器中进行连续喷雾逆流传输浸取,浸取器的转速为16r/min,浸取温度为70℃,浸取时间为20min,浸取后的树脂从浸取器的上口出料进入离心机进行固液分离,液体浸取剂送至多效蒸发器进料缓冲槽;浸取后的液体部分从浸取器的下口溢流出,也送至多效蒸发器进料缓冲槽,再将其送入多效蒸发器于65℃,真空度0.09MPa进行蒸发,分别回收纯净的固体助剂及液体助剂浸取剂,无需后处理可直接循环使用;浸取完后的固体树脂粗产品采用5次、每次350kg脱盐水或上一批次产品的洗水进行逆流水洗、固液分离,以去除产物中包裹的盐和极少量助剂,分离后的含水聚芳醚树脂在温度110℃、真空度0.085MPa干燥6h,获得纯化聚芳醚树脂,其产率为98.8%,特性粘数[η]=0.67(粘度测试溶剂为N-甲基吡咯烷酮),溶剂回收率为99.8%,助剂回收率为99.9%,所得聚芳醚树脂的纯度为99.98%,白度为85,杂质含量为12ppm;而洗水则送至洗水槽与萃取分离水合并在2kg臭氧+35kg双氧水的作用下进行50℃氧化处理,去除洗水中的有机物及氨氮杂质,在电解槽内及电解催化剂氧化铱的作用下,进行高效转化,生成氢氧化钠、氯气及氢气,氢氧化钠用于聚合脱水工段,氯气用于制备二卤代芳香单体,氢气作为清洁能源循环使用。
尽管上面结合实施例描述了本发明,但是本领域技术人员应该清楚,在不脱离权利要求的精神和范围的情况下,可以对上述实施例进行各种修改。
Claims (10)
- 一种高白度低杂质含量聚芳醚的制备方法,其特征在于,所述制备方法包括如下步骤:1)脱水反应:将硫化物、助剂和溶剂加入反应釜中,氮气或惰性气体保护下,脱水反应得到脱水后的反应溶液,脱除的含溶剂混合液体送入脱水冷凝液罐合并集中处理;脱水后的反应溶液降温后与二氯代芳香化合物反应得反应产物混合液;2)第一次回收溶剂:步骤1)所得反应产物混合液于150~220℃下通过高温过滤,回收反应产物混合液中的部分溶剂,将回收的溶剂输送至溶剂回收槽,直接用于下一批次物料聚合;3)萃取法回收溶剂及树脂纯化:将步骤2)过滤后物料降温至10~160℃送至萃取釜,分批次加入萃取剂,密闭条件下于温度10~160℃、压力0~1MPa下分批次萃取剩余溶剂;萃取后的混合溶液经过滤后送入富萃取剂混合液槽,并将其与步骤1)中的含溶剂混合液进行混合,再经离心萃取或逆流塔式萃取;然后分别将含溶剂和萃取剂的混合液送至溶剂/萃取剂槽,水送至洗水槽;并将含溶剂和萃取剂的混合液进行精馏分离,分别回收萃取剂和溶剂,循环利用;4)助剂回收、树脂洗涤及洗水提纯:经步骤3)处理后得到的固体树脂粗产品采用助剂浸取剂进行助剂的回收和分离;浸取完成后的液体进行多效蒸发,液体回收作为下一批助剂浸取剂使用,固体则为回收的助剂,无需后处理可直接使用;浸取完成后的固体树脂粗产品采用脱盐水或上一批次产品的洗水进行逆流水洗和固液分离,分离后的含水聚芳醚树脂通过真空干燥获得高白度低杂质含量的聚芳醚;而洗水则送至洗水槽与步骤3)中萃取分离水合并再加入氧化剂进行氧化处理,去除洗水中的有机物及氨氮杂质,使其达到电解的工况要求;5)氯化钠电解:经步骤4)处理后得到合格的氯化钠水溶液,置于电解槽内,在电解催化剂的作用下,转化生成氢氧化钠、氯气及氢气;氢氧化钠作为烧碱出售或用于聚芳醚树脂的前端聚合反应,氯气用于生产聚芳醚中的生产用原料对二氯苯或4,4’-二氯二苯砜,氢气作为清洁能源循环使用;其中,各原料由以下重量份的组分组成:
- 根据权利要求1所述的一种高白度低杂质含量聚芳醚的制备方法,其特征在于,步骤1)的方法为:将硫化物、助剂和溶剂加入反应釜中,氮气保护下,于温度140~230℃脱水反应0.5~3h,得到脱水后的反应溶液,脱除的含溶剂混合液体送入脱水冷凝液罐合并集中处理;待反应溶液温度降至80~180℃时,加入二氯代芳香化合物,于温度150~230℃下反应0.5~8h,再在温度230~280℃保持0.5~10h,得到反应产物混合液。
- 根据权利要求1或2所述的一种高白度低杂质含量聚芳醚的制备方法,其特征在于,所述硫化物选自下述化合物:Na2S或NaHS中的任一种;所述二氯代芳香化合物的结构式为Cl-Ar-Cl,其中,
中的至少一种,其中,m=2、4、6、8或10;进一步,步骤1)中,所述溶剂为甲酰胺、乙酰胺、N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基吡咯烷酮、N,N-二甲基丙烯基脲、1,3-二甲基-2-咪唑啉酮、N-环己基吡咯烷酮、六甲基磷酰三胺、环丁砜、二苯砜、ε-己内酰胺、二甲基亚砜、二甲基砜、喹啉、异喹啉、2,4-二甲基环丁砜或N-甲基己内酰胺中的至少一种;或所述溶剂为制备方法中步骤3)回收的纯度≥99%的高纯度溶剂;进一步,步骤1)中,所述助剂为氢氧化锂、氢氧化钠、氢氧化钾、氢氧化镁、氢氧化 钙、氢氧化钡、氢氧化铝、碳酸锂、碳酸钠、碳酸钾、碳酸镁、碳酸钙、碳酸钡、碳酸氢锂、碳酸氢钠、碳酸氢钾、碳酸氢镁、碳酸氢钙、碳酸氢钡、乙酸锂、乙酸钠、乙酸钾、苯甲酸锂、苯甲酸钠、乙二胺四乙酸锂、乙二胺四乙酸钠、乙二胺四乙酸三钠、乙二胺四乙酸钾、乙二胺四乙酸三钾、十二烷基苯磺酸钠、对甲基苯甲酸钠、对甲基苯甲酸锂、对苯二甲酸钠、对苯二甲酸钠、对甲基苯磺酸钠、对氨基苯磺酸钠、草酸钠、草酸锂、丁二酸钠、丁二酸锂、己二酸钠、己二酸锂、氯化锂、磷酸钠、磷酸锂、酒石酸钠、酒石酸锂、酒石酸钾、海藻酸钠、葡萄糖酸钠、乳酸钠、山梨酸钠、山梨酸钾、赖氨酸钠、赖氨酸钾、胱氨酸钠、6-氨基己酸钠、庚糖酸钠、月桂酸钠、柠檬酸钠、甘胆酸钠、二辛基琥珀酸钠、乙二胺四甲叉磷酸钠、二乙烯三胺五甲叉膦酸钠、胺三甲叉磷酸钠、十二烷基三乙基氯化铵、十二烷基二甲基溴化铵或硬脂酸钠中的至少一种。 - 根据权利要求1~3任一项所述的一种高白度低杂质含量聚芳醚的制备方法,其特征在于,步骤3)中,萃取后的混合溶液与步骤1)中的含溶剂混合液的体积比为:1~5份:1~3份。
- 根据权利要求1~4任一项所述的一种高白度低杂质含量聚芳醚的制备方法,其特征在于,步骤3)中,所述萃取剂为三氯甲烷、二氯甲烷、四氯乙烷、四氯化碳、环己烷、乙酸乙酯、乙酸丁酯或异丙醚中的任一种。
- 根据权利要求1~5任一项所述的一种高白度低杂质含量聚芳醚的制备方法,其特征在于,步骤4)中,采用助剂浸取剂进行助剂的回收和分离的方法为:将步骤3)得到的固体树脂粗产品100份、300~3000份助剂浸取剂加入助剂浸取器中进行连续喷雾逆流传输浸取,浸取器的转速为2~30r/min,浸取温度为20~80℃,浸取时间为1~60min;浸取后的树脂从浸取器的上口出料进入离心机进行固液分离,液体浸取剂送至多效蒸发器进料缓冲槽;浸取后的液体部分从浸取器的下口溢流出,也送至多效蒸发器进料缓冲槽,再将其送入多效蒸发器于40~90℃,真空度0.04~0.09MPa进行蒸发,多效蒸发后的液体回收作为下一批助剂浸取剂直接使用,多效蒸发后的固体则回收作为助剂直接使用。
- 根据权利要求1~6任一项所述的一种高白度低杂质含量聚芳醚的制备方法,其特征在于,步骤4)中,浸取完成后的固体树脂粗产品采用3~5次、每次300~1000份脱盐水或上一批次产品的洗水进行逆流水洗、固液分离,以去除产物中包裹的盐和极少量助剂,分离后的含水聚芳醚树脂在温度80~120℃、真空度0.03~0.095MPa干燥1~12h,获得高白度低杂质含量聚芳醚树脂;而洗水则送至洗水槽与步骤3)中萃取分离水合并在氧化剂的作用下进行室温~60℃氧化处理,去除洗水中的有机物及氨氮杂质,达到电解纯度要求。
- 根据权利要求1~7任一项所述的一种高白度低杂质含量聚芳醚的制备方法,其特征 在于,步骤4)中,所述助剂浸取剂为甲醇、乙醇、丙醇、乙二醇、丙二醇、丙三醇、异丙醇、异丁醇、叔丁醇、正丁醇、正戊醇、异戊醇、正己醇、正庚醇、正辛醇、异辛醇、丙酮、丁酮、环戊酮、环己酮、三氯甲烷、二氯甲烷、四氯乙烷或四氯化碳中的至少一种;进一步,步骤5)中,所述氧化剂为双氧水、臭氧、芬顿试剂或氯化铁中的至少一种;进一步,步骤5)中,所述电解催化剂为氧化钌、氧化钇、氧化铈、氧化镧、二氧化钛或氧化铱中的至少一种。
- 一种聚芳醚,其特征在于,所述聚芳醚采用权利要求1~8任一项所述的方法制得。
- 根据权利要求9所述的聚芳醚,其特征在于,所述聚芳醚的白度≥85;和/或:所述聚芳醚的杂质含量≤12ppm;和/或:所述聚芳醚的纯度≥99.9%。
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