CN108463481B - 制备聚碳酸酯的方法 - Google Patents
制备聚碳酸酯的方法 Download PDFInfo
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- CN108463481B CN108463481B CN201680075234.XA CN201680075234A CN108463481B CN 108463481 B CN108463481 B CN 108463481B CN 201680075234 A CN201680075234 A CN 201680075234A CN 108463481 B CN108463481 B CN 108463481B
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- Prior art keywords
- carbonate
- bis
- dihydroxy
- hydroxyphenyl
- reaction
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- 229920000515 polycarbonate Polymers 0.000 title claims abstract description 30
- 239000004417 polycarbonate Substances 0.000 title claims abstract description 30
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 10
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims abstract description 42
- -1 diaryl carbonate Chemical compound 0.000 claims abstract description 42
- 238000006243 chemical reaction Methods 0.000 claims abstract description 36
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 19
- 239000002685 polymerization catalyst Substances 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 23
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical group C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 15
- 150000001491 aromatic compounds Chemical class 0.000 claims description 10
- 239000000654 additive Substances 0.000 claims description 3
- 230000000996 additive effect Effects 0.000 claims 1
- 239000003054 catalyst Substances 0.000 description 21
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 11
- 229930185605 Bisphenol Natural products 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 150000004703 alkoxides Chemical class 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- 229910052719 titanium Inorganic materials 0.000 description 4
- 239000010936 titanium Substances 0.000 description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229910052718 tin Inorganic materials 0.000 description 3
- 238000005809 transesterification reaction Methods 0.000 description 3
- LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-bis(diphenylphosphino)propane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 2
- XCZKKZXWDBOGPA-UHFFFAOYSA-N 2-phenylbenzene-1,4-diol Chemical compound OC1=CC=C(O)C(C=2C=CC=CC=2)=C1 XCZKKZXWDBOGPA-UHFFFAOYSA-N 0.000 description 2
- IJFXRHURBJZNAO-UHFFFAOYSA-N 3-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(O)=C1 IJFXRHURBJZNAO-UHFFFAOYSA-N 0.000 description 2
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- FNYDIAAMUCQQDE-UHFFFAOYSA-N 4-methylbenzene-1,3-diol Chemical compound CC1=CC=C(O)C=C1O FNYDIAAMUCQQDE-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 2
- GUUVPOWQJOLRAS-UHFFFAOYSA-N Diphenyl disulfide Chemical compound C=1C=CC=CC=1SSC1=CC=CC=C1 GUUVPOWQJOLRAS-UHFFFAOYSA-N 0.000 description 2
- 238000005618 Fries rearrangement reaction Methods 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 125000005233 alkylalcohol group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 125000005587 carbonate group Chemical group 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 150000005205 dihydroxybenzenes Chemical class 0.000 description 2
- YVSCCMNRWFOKDU-UHFFFAOYSA-N hexanedioic acid Chemical compound OC(=O)CCCCC(O)=O.OC(=O)CCCCC(O)=O YVSCCMNRWFOKDU-UHFFFAOYSA-N 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 238000000066 reactive distillation Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 2
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 2
- HTDIUWINAKAPER-UHFFFAOYSA-N trimethylarsine Chemical compound C[As](C)C HTDIUWINAKAPER-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- OERNJTNJEZOPIA-UHFFFAOYSA-N zirconium nitrate Chemical compound [Zr+4].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O OERNJTNJEZOPIA-UHFFFAOYSA-N 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- RYSXWUYLAWPLES-MTOQALJVSA-N (Z)-4-hydroxypent-3-en-2-one titanium Chemical compound [Ti].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O RYSXWUYLAWPLES-MTOQALJVSA-N 0.000 description 1
- YOBOXHGSEJBUPB-MTOQALJVSA-N (z)-4-hydroxypent-3-en-2-one;zirconium Chemical compound [Zr].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O YOBOXHGSEJBUPB-MTOQALJVSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- BNNBECJSDDMHFF-UHFFFAOYSA-N 2,2,3,3-tetramethylcyclobutane-1,1-diol Chemical compound CC1(C)CC(O)(O)C1(C)C BNNBECJSDDMHFF-UHFFFAOYSA-N 0.000 description 1
- FQXGHZNSUOHCLO-UHFFFAOYSA-N 2,2,4,4-tetramethyl-1,3-cyclobutanediol Chemical compound CC1(C)C(O)C(C)(C)C1O FQXGHZNSUOHCLO-UHFFFAOYSA-N 0.000 description 1
- CDQXVCNCQFXPSF-UHFFFAOYSA-N 2,3,5,6-tetrabromo-4-[1-(2,3,5,6-tetrabromo-4-hydroxyphenyl)cyclohexyl]phenol Chemical compound BrC1=C(Br)C(O)=C(Br)C(Br)=C1C1(C=2C(=C(Br)C(O)=C(Br)C=2Br)Br)CCCCC1 CDQXVCNCQFXPSF-UHFFFAOYSA-N 0.000 description 1
- VRXQOCASOOBADQ-UHFFFAOYSA-N 2,3,5,6-tetrabromo-4-[2-(2,3,5,6-tetrabromo-4-hydroxyphenyl)propan-2-yl]phenol Chemical compound BrC=1C(Br)=C(O)C(Br)=C(Br)C=1C(C)(C)C1=C(Br)C(Br)=C(O)C(Br)=C1Br VRXQOCASOOBADQ-UHFFFAOYSA-N 0.000 description 1
- DNFSJFZWNDZYHA-UHFFFAOYSA-N 2,3,5,6-tetrabromo-4-[3,3,5-trimethyl-1-(2,3,5,6-tetrabromo-4-hydroxyphenyl)cyclohexyl]phenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C(=C(Br)C(O)=C(Br)C=1Br)Br)C1=C(Br)C(Br)=C(O)C(Br)=C1Br DNFSJFZWNDZYHA-UHFFFAOYSA-N 0.000 description 1
- PBYLGADGYCTQOT-UHFFFAOYSA-N 2,3,5,6-tetrachloro-4-[1-(2,3,5,6-tetrachloro-4-hydroxyphenyl)cyclohexyl]phenol Chemical compound ClC1=C(Cl)C(O)=C(Cl)C(Cl)=C1C1(C=2C(=C(Cl)C(O)=C(Cl)C=2Cl)Cl)CCCCC1 PBYLGADGYCTQOT-UHFFFAOYSA-N 0.000 description 1
- JNSWTHTUMBCINC-UHFFFAOYSA-N 2,3,5,6-tetrachloro-4-[3,3,5-trimethyl-1-(2,3,5,6-tetrachloro-4-hydroxyphenyl)cyclohexyl]phenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C(=C(Cl)C(O)=C(Cl)C=1Cl)Cl)C1=C(Cl)C(Cl)=C(O)C(Cl)=C1Cl JNSWTHTUMBCINC-UHFFFAOYSA-N 0.000 description 1
- JRWCWHILGVMUTD-UHFFFAOYSA-N 2,6-dibromo-4-[1-(3,5-dibromo-4-hydroxyphenyl)-3,3,5-trimethylcyclohexyl]phenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C=C(Br)C(O)=C(Br)C=1)C1=CC(Br)=C(O)C(Br)=C1 JRWCWHILGVMUTD-UHFFFAOYSA-N 0.000 description 1
- XJFNFDUOEIPZNK-UHFFFAOYSA-N 2,6-dibromo-4-[1-(3,5-dibromo-4-hydroxyphenyl)cyclohexyl]phenol Chemical compound C1=C(Br)C(O)=C(Br)C=C1C1(C=2C=C(Br)C(O)=C(Br)C=2)CCCCC1 XJFNFDUOEIPZNK-UHFFFAOYSA-N 0.000 description 1
- HHWOEAFLIJITGC-UHFFFAOYSA-N 2,6-dichloro-4-[1-(3,5-dichloro-4-hydroxyphenyl)-3,3,5-trimethylcyclohexyl]phenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C=C(Cl)C(O)=C(Cl)C=1)C1=CC(Cl)=C(O)C(Cl)=C1 HHWOEAFLIJITGC-UHFFFAOYSA-N 0.000 description 1
- ANLICCDGDIUHJE-UHFFFAOYSA-N 2,6-dichloro-4-[1-(3,5-dichloro-4-hydroxyphenyl)cyclohexyl]phenol Chemical compound C1=C(Cl)C(O)=C(Cl)C=C1C1(C=2C=C(Cl)C(O)=C(Cl)C=2)CCCCC1 ANLICCDGDIUHJE-UHFFFAOYSA-N 0.000 description 1
- ALLIENKNQNBVMR-UHFFFAOYSA-N 2,6-dimethyl-4-(3,3,5-trimethylcyclohexyl)phenol Chemical compound C1C(C)(C)CC(C)CC1C1=CC(C)=C(O)C(C)=C1 ALLIENKNQNBVMR-UHFFFAOYSA-N 0.000 description 1
- VJJCPYIHQDQHLW-UHFFFAOYSA-N 2,6-ditert-butyl-4-[1-(3,5-ditert-butyl-4-hydroxyphenyl)-3,3,5-trimethylcyclohexyl]phenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C=C(C(O)=C(C=1)C(C)(C)C)C(C)(C)C)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VJJCPYIHQDQHLW-UHFFFAOYSA-N 0.000 description 1
- ROMMRTLCTSUNMY-UHFFFAOYSA-N 2,6-ditert-butyl-4-[1-(3,5-ditert-butyl-4-hydroxyphenyl)cyclohexyl]phenol Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(C2(CCCCC2)C=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 ROMMRTLCTSUNMY-UHFFFAOYSA-N 0.000 description 1
- QHPKIUDQDCWRKO-UHFFFAOYSA-N 2,6-ditert-butyl-4-[2-(3,5-ditert-butyl-4-hydroxyphenyl)propan-2-yl]phenol Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(C(C)(C)C=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 QHPKIUDQDCWRKO-UHFFFAOYSA-N 0.000 description 1
- BXGYYDRIMBPOMN-UHFFFAOYSA-N 2-(hydroxymethoxy)ethoxymethanol Chemical compound OCOCCOCO BXGYYDRIMBPOMN-UHFFFAOYSA-N 0.000 description 1
- RPLUVCHAAFRTMW-UHFFFAOYSA-N 2-bromo-4-[1-(3-bromo-4-hydroxy-5-methylphenyl)-3,3,5-trimethylcyclohexyl]-6-methylphenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C=C(Br)C(O)=C(C)C=1)C1=CC(C)=C(O)C(Br)=C1 RPLUVCHAAFRTMW-UHFFFAOYSA-N 0.000 description 1
- KPPIKGCTARUWAS-UHFFFAOYSA-N 2-bromo-4-[1-(3-bromo-4-hydroxy-5-methylphenyl)cyclohexyl]-6-methylphenol Chemical compound BrC1=C(O)C(C)=CC(C2(CCCCC2)C=2C=C(Br)C(O)=C(C)C=2)=C1 KPPIKGCTARUWAS-UHFFFAOYSA-N 0.000 description 1
- LTUNFYAQACHQPQ-UHFFFAOYSA-N 2-bromo-4-[1-(3-bromo-4-hydroxy-5-phenylphenyl)-3,3,5-trimethylcyclohexyl]-6-phenylphenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C=C(C(O)=C(Br)C=1)C=1C=CC=CC=1)C1=CC(Br)=C(O)C(C=2C=CC=CC=2)=C1 LTUNFYAQACHQPQ-UHFFFAOYSA-N 0.000 description 1
- MLVSCWXAPGXQPH-UHFFFAOYSA-N 2-bromo-4-[1-(3-bromo-4-hydroxy-5-phenylphenyl)cyclohexyl]-6-phenylphenol Chemical compound OC1=C(Br)C=C(C2(CCCCC2)C=2C=C(C(O)=C(Br)C=2)C=2C=CC=CC=2)C=C1C1=CC=CC=C1 MLVSCWXAPGXQPH-UHFFFAOYSA-N 0.000 description 1
- MDOOVKUOPDTSIM-UHFFFAOYSA-N 2-bromo-4-[1-(3-bromo-4-hydroxy-5-propan-2-ylphenyl)-3,3,5-trimethylcyclohexyl]-6-propan-2-ylphenol Chemical compound BrC1=C(O)C(C(C)C)=CC(C2(CC(C)(C)CC(C)C2)C=2C=C(C(O)=C(Br)C=2)C(C)C)=C1 MDOOVKUOPDTSIM-UHFFFAOYSA-N 0.000 description 1
- XQJRPVIHXKVMLV-UHFFFAOYSA-N 2-bromo-4-[1-(3-bromo-4-hydroxy-5-propan-2-ylphenyl)cyclohexyl]-6-propan-2-ylphenol Chemical compound BrC1=C(O)C(C(C)C)=CC(C2(CCCCC2)C=2C=C(C(O)=C(Br)C=2)C(C)C)=C1 XQJRPVIHXKVMLV-UHFFFAOYSA-N 0.000 description 1
- RGMJRYWGSRIVQU-UHFFFAOYSA-N 2-bromo-4-[1-(3-bromo-4-hydroxyphenyl)-3,3,5-trimethylcyclohexyl]phenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C=C(Br)C(O)=CC=1)C1=CC=C(O)C(Br)=C1 RGMJRYWGSRIVQU-UHFFFAOYSA-N 0.000 description 1
- AOJRBWSWENFQGS-UHFFFAOYSA-N 2-bromo-4-[1-(3-bromo-4-hydroxyphenyl)cyclohexyl]phenol Chemical compound C1=C(Br)C(O)=CC=C1C1(C=2C=C(Br)C(O)=CC=2)CCCCC1 AOJRBWSWENFQGS-UHFFFAOYSA-N 0.000 description 1
- IOQVTKBBXVJSDQ-UHFFFAOYSA-N 2-bromo-4-[1-(3-bromo-5-tert-butyl-4-hydroxyphenyl)-3,3,5-trimethylcyclohexyl]-6-tert-butylphenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C=C(C(O)=C(Br)C=1)C(C)(C)C)C1=CC(Br)=C(O)C(C(C)(C)C)=C1 IOQVTKBBXVJSDQ-UHFFFAOYSA-N 0.000 description 1
- MTXHQKMTAGXROL-UHFFFAOYSA-N 2-bromo-4-[1-(3-bromo-5-tert-butyl-4-hydroxyphenyl)cyclohexyl]-6-tert-butylphenol Chemical compound BrC1=C(O)C(C(C)(C)C)=CC(C2(CCCCC2)C=2C=C(C(O)=C(Br)C=2)C(C)(C)C)=C1 MTXHQKMTAGXROL-UHFFFAOYSA-N 0.000 description 1
- AKUCXWDJOMIBEH-UHFFFAOYSA-N 2-bromo-4-[2-(3-bromo-4-hydroxy-5-methylphenyl)propan-2-yl]-6-methylphenol Chemical compound BrC1=C(O)C(C)=CC(C(C)(C)C=2C=C(Br)C(O)=C(C)C=2)=C1 AKUCXWDJOMIBEH-UHFFFAOYSA-N 0.000 description 1
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- SDDLEVPIDBLVHC-UHFFFAOYSA-N Bisphenol Z Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)CCCCC1 SDDLEVPIDBLVHC-UHFFFAOYSA-N 0.000 description 1
- BBRVSQDNTQXUQA-UHFFFAOYSA-N CCC=C(C)OC(O)=O Chemical compound CCC=C(C)OC(O)=O BBRVSQDNTQXUQA-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical class OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- KLDXJTOLSGUMSJ-JGWLITMVSA-N Isosorbide Chemical compound O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-JGWLITMVSA-N 0.000 description 1
- 239000007836 KH2PO4 Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- KYPYTERUKNKOLP-UHFFFAOYSA-N Tetrachlorobisphenol A Chemical compound C=1C(Cl)=C(O)C(Cl)=CC=1C(C)(C)C1=CC(Cl)=C(O)C(Cl)=C1 KYPYTERUKNKOLP-UHFFFAOYSA-N 0.000 description 1
- GCTFWCDSFPMHHS-UHFFFAOYSA-M Tributyltin chloride Chemical compound CCCC[Sn](Cl)(CCCC)CCCC GCTFWCDSFPMHHS-UHFFFAOYSA-M 0.000 description 1
- XDODWINGEHBYRT-OCAPTIKFSA-N [(1s,2r)-2-(hydroxymethyl)cyclohexyl]methanol Chemical compound OC[C@H]1CCCC[C@H]1CO XDODWINGEHBYRT-OCAPTIKFSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- INNSZZHSFSFSGS-UHFFFAOYSA-N acetic acid;titanium Chemical compound [Ti].CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O INNSZZHSFSFSGS-UHFFFAOYSA-N 0.000 description 1
- 229910052910 alkali metal silicate Inorganic materials 0.000 description 1
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 description 1
- 229910052915 alkaline earth metal silicate Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- ILRRQNADMUWWFW-UHFFFAOYSA-K aluminium phosphate Chemical compound O1[Al]2OP1(=O)O2 ILRRQNADMUWWFW-UHFFFAOYSA-K 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- RBFQJDQYXXHULB-UHFFFAOYSA-N arsane Chemical compound [AsH3] RBFQJDQYXXHULB-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 1
- JKJWYKGYGWOAHT-UHFFFAOYSA-N bis(prop-2-enyl) carbonate Chemical compound C=CCOC(=O)OCC=C JKJWYKGYGWOAHT-UHFFFAOYSA-N 0.000 description 1
- 150000004648 butanoic acid derivatives Chemical class 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- DISYGAAFCMVRKW-UHFFFAOYSA-N butyl ethyl carbonate Chemical compound CCCCOC(=O)OCC DISYGAAFCMVRKW-UHFFFAOYSA-N 0.000 description 1
- FWBMVXOCTXTBAD-UHFFFAOYSA-N butyl methyl carbonate Chemical compound CCCCOC(=O)OC FWBMVXOCTXTBAD-UHFFFAOYSA-N 0.000 description 1
- VASVAWIFVXAQMI-UHFFFAOYSA-N butyl propyl carbonate Chemical compound CCCCOC(=O)OCCC VASVAWIFVXAQMI-UHFFFAOYSA-N 0.000 description 1
- WIHMDCQAEONXND-UHFFFAOYSA-M butyl-hydroxy-oxotin Chemical compound CCCC[Sn](O)=O WIHMDCQAEONXND-UHFFFAOYSA-M 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 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
- 229910052799 carbon Inorganic materials 0.000 description 1
- RAFKKJRZLDODKG-UHFFFAOYSA-N carbonic acid;propan-2-one Chemical compound CC(C)=O.OC(O)=O RAFKKJRZLDODKG-UHFFFAOYSA-N 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- QLVWOKQMDLQXNN-UHFFFAOYSA-N dibutyl carbonate Chemical compound CCCCOC(=O)OCCCC QLVWOKQMDLQXNN-UHFFFAOYSA-N 0.000 description 1
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- ZFTFAPZRGNKQPU-UHFFFAOYSA-N dicarbonic acid Chemical compound OC(=O)OC(O)=O ZFTFAPZRGNKQPU-UHFFFAOYSA-N 0.000 description 1
- FYIBPWZEZWVDQB-UHFFFAOYSA-N dicyclohexyl carbonate Chemical compound C1CCCCC1OC(=O)OC1CCCCC1 FYIBPWZEZWVDQB-UHFFFAOYSA-N 0.000 description 1
- AJHQRWJZHVBYLU-UHFFFAOYSA-N dicyclopentyl carbonate Chemical compound C1CCCC1OC(=O)OC1CCCC1 AJHQRWJZHVBYLU-UHFFFAOYSA-N 0.000 description 1
- ZEBJPYUECLCDRQ-UHFFFAOYSA-N didecyl carbonate Chemical compound CCCCCCCCCCOC(=O)OCCCCCCCCCC ZEBJPYUECLCDRQ-UHFFFAOYSA-N 0.000 description 1
- ZYKOICDLSSOLAN-UHFFFAOYSA-N diheptyl carbonate Chemical compound CCCCCCCOC(=O)OCCCCCCC ZYKOICDLSSOLAN-UHFFFAOYSA-N 0.000 description 1
- OKQDSOXFNBWWJL-UHFFFAOYSA-N dihexyl carbonate Chemical compound CCCCCCOC(=O)OCCCCCC OKQDSOXFNBWWJL-UHFFFAOYSA-N 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical group COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- PWEVMPIIOJUPRI-UHFFFAOYSA-N dimethyltin Chemical compound C[Sn]C PWEVMPIIOJUPRI-UHFFFAOYSA-N 0.000 description 1
- FHWFURWDUGYUMA-UHFFFAOYSA-N dinonyl carbonate Chemical compound CCCCCCCCCOC(=O)OCCCCCCCCC FHWFURWDUGYUMA-UHFFFAOYSA-N 0.000 description 1
- PKPOVTYZGGYDIJ-UHFFFAOYSA-N dioctyl carbonate Chemical compound CCCCCCCCOC(=O)OCCCCCCCC PKPOVTYZGGYDIJ-UHFFFAOYSA-N 0.000 description 1
- HSNQKJVQUFYBBY-UHFFFAOYSA-N dipentyl carbonate Chemical compound CCCCCOC(=O)OCCCCC HSNQKJVQUFYBBY-UHFFFAOYSA-N 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
- VUPKGFBOKBGHFZ-UHFFFAOYSA-N dipropyl carbonate Chemical compound CCCOC(=O)OCCC VUPKGFBOKBGHFZ-UHFFFAOYSA-N 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- PLONEVHFXDFSLA-UHFFFAOYSA-N ethyl hexanoate;tin(2+) Chemical compound [Sn+2].CCCCCC(=O)OCC PLONEVHFXDFSLA-UHFFFAOYSA-N 0.000 description 1
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 1
- CYEDOLFRAIXARV-UHFFFAOYSA-N ethyl propyl carbonate Chemical compound CCCOC(=O)OCC CYEDOLFRAIXARV-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- UAKLXJQIONWKQF-UHFFFAOYSA-N heptan-2-yl hydrogen carbonate Chemical compound CCCCCC(C)OC(O)=O UAKLXJQIONWKQF-UHFFFAOYSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- IBTAFYOTPNVGLR-UHFFFAOYSA-N heptyl methyl carbonate Chemical compound CCCCCCCOC(=O)OC IBTAFYOTPNVGLR-UHFFFAOYSA-N 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N hydroquinone methyl ether Natural products COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229960002479 isosorbide Drugs 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- AWNVVAMWLMUZOZ-UHFFFAOYSA-J magnesium;disodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Mg+2].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O AWNVVAMWLMUZOZ-UHFFFAOYSA-J 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- ZJTLZYDQJHKRMQ-UHFFFAOYSA-N menadiol Chemical compound C1=CC=CC2=C(O)C(C)=CC(O)=C21 ZJTLZYDQJHKRMQ-UHFFFAOYSA-N 0.000 description 1
- AEPIEBUZUWHMGG-UHFFFAOYSA-N methyl nonyl carbonate Chemical compound CCCCCCCCCOC(=O)OC AEPIEBUZUWHMGG-UHFFFAOYSA-N 0.000 description 1
- MKSDSFWGKQOBHN-UHFFFAOYSA-N methyl octyl carbonate Chemical compound CCCCCCCCOC(=O)OC MKSDSFWGKQOBHN-UHFFFAOYSA-N 0.000 description 1
- PAQGTCFSKWUKHW-UHFFFAOYSA-N methyl pentyl carbonate Chemical compound CCCCCOC(=O)OC PAQGTCFSKWUKHW-UHFFFAOYSA-N 0.000 description 1
- KKQAVHGECIBFRQ-UHFFFAOYSA-N methyl propyl carbonate Chemical compound CCCOC(=O)OC KKQAVHGECIBFRQ-UHFFFAOYSA-N 0.000 description 1
- 238000007479 molecular analysis Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical class C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 1
- XOOMNEFVDUTJPP-UHFFFAOYSA-N naphthalene-1,3-diol Chemical compound C1=CC=CC2=CC(O)=CC(O)=C21 XOOMNEFVDUTJPP-UHFFFAOYSA-N 0.000 description 1
- PCILLCXFKWDRMK-UHFFFAOYSA-N naphthalene-1,4-diol Chemical compound C1=CC=C2C(O)=CC=C(O)C2=C1 PCILLCXFKWDRMK-UHFFFAOYSA-N 0.000 description 1
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 1
- MNZMMCVIXORAQL-UHFFFAOYSA-N naphthalene-2,6-diol Chemical compound C1=C(O)C=CC2=CC(O)=CC=C21 MNZMMCVIXORAQL-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- OTLDLKLSNZMTTA-UHFFFAOYSA-N octahydro-1h-4,7-methanoindene-1,5-diyldimethanol Chemical compound C1C2C3C(CO)CCC3C1C(CO)C2 OTLDLKLSNZMTTA-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- ZLLNYWQSSYUXJM-UHFFFAOYSA-N phenol tetraphenylphosphanium Chemical compound C1(=CC=CC=C1)O.C1(=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 ZLLNYWQSSYUXJM-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- ORQWTLCYLDRDHK-UHFFFAOYSA-N phenylselanylbenzene Chemical compound C=1C=CC=CC=1[Se]C1=CC=CC=C1 ORQWTLCYLDRDHK-UHFFFAOYSA-N 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000004023 quaternary phosphonium compounds Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 229940065287 selenium compound Drugs 0.000 description 1
- 150000003343 selenium compounds Chemical class 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 229960002920 sorbitol Drugs 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical group 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
- GFZMLBWMGBLIDI-UHFFFAOYSA-M tetrabutylphosphanium;acetate Chemical compound CC([O-])=O.CCCC[P+](CCCC)(CCCC)CCCC GFZMLBWMGBLIDI-UHFFFAOYSA-M 0.000 description 1
- DFQPZDGUFQJANM-UHFFFAOYSA-M tetrabutylphosphanium;hydroxide Chemical compound [OH-].CCCC[P+](CCCC)(CCCC)CCCC DFQPZDGUFQJANM-UHFFFAOYSA-M 0.000 description 1
- TWRYZRQZQIBEIE-UHFFFAOYSA-N tetramethoxystannane Chemical compound [Sn+4].[O-]C.[O-]C.[O-]C.[O-]C TWRYZRQZQIBEIE-UHFFFAOYSA-N 0.000 description 1
- HYVDRSVZYMKTKG-UHFFFAOYSA-M tetramethylphosphanium;acetate Chemical compound CC([O-])=O.C[P+](C)(C)C HYVDRSVZYMKTKG-UHFFFAOYSA-M 0.000 description 1
- ZPRWYZRUPRQWKR-UHFFFAOYSA-M tetramethylphosphanium;formate Chemical compound [O-]C=O.C[P+](C)(C)C ZPRWYZRUPRQWKR-UHFFFAOYSA-M 0.000 description 1
- CRUVUWATNULHFA-UHFFFAOYSA-M tetramethylphosphanium;hydroxide Chemical compound [OH-].C[P+](C)(C)C CRUVUWATNULHFA-UHFFFAOYSA-M 0.000 description 1
- 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 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- XAZAQTBGMXGTBD-UHFFFAOYSA-N tributylarsane Chemical compound CCCC[As](CCCC)CCCC XAZAQTBGMXGTBD-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
- BPLUKJNHPBNVQL-UHFFFAOYSA-N triphenylarsine Chemical compound C1=CC=CC=C1[As](C=1C=CC=CC=1)C1=CC=CC=C1 BPLUKJNHPBNVQL-UHFFFAOYSA-N 0.000 description 1
- HVYVMSPIJIWUNA-UHFFFAOYSA-N triphenylstibine Chemical compound C1=CC=CC=C1[Sb](C=1C=CC=CC=1)C1=CC=CC=C1 HVYVMSPIJIWUNA-UHFFFAOYSA-N 0.000 description 1
- 239000012953 triphenylsulfonium Substances 0.000 description 1
- YDQFYRJRIUKWCQ-UHFFFAOYSA-N undecan-2-yl hydrogen carbonate Chemical compound CCCCCCCCCC(C)OC(O)=O YDQFYRJRIUKWCQ-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- JQOAZIZLIIOXEW-UHFFFAOYSA-N zinc;chromium(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[Cr+3].[Cr+3].[Zn+2] JQOAZIZLIIOXEW-UHFFFAOYSA-N 0.000 description 1
- 150000003754 zirconium Chemical class 0.000 description 1
- 229910052726 zirconium Inorganic materials 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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
- C08G64/30—General preparatory processes using carbonates
- C08G64/305—General preparatory processes using carbonates and alcohols
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- C—CHEMISTRY; METALLURGY
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Abstract
一种制备聚碳酸酯的方法,其包含使二羟基封端的碳酸酯和碳酸二芳酯在反应区中在聚合催化剂存在下在聚合条件下接触以产生聚碳酸酯。
Description
相关申请的引用
本申请要求2015年12月22日提交的美国临时专利申请第62/270723号的权益。
技术领域
本发明涉及一种由碳酸二烷酯和二羟基化合物制备寡聚物的方法。
背景技术
在本文中也被称为聚碳酸酯的芳香族聚碳酸酯是许多不同制造领域中广泛使用的原料。归因于材料的硬度和透明度,其可以应用于如汽车窗和光学透镜的多样的应用中。据相信,对聚碳酸酯的需求在未来几年将显著地增加,需要改进聚碳酸酯制备,特别是在效率和环境影响方面。
已知数种制备聚碳酸酯的方法。举例来说,在工业规模上应用包括使光气和2,2-双(4-羟苯基)丙烷(BPA)在相转移条件下反应的方法。然而,这种方法具有利用毒性组分光气和产生含氯化物的废弃物流的固有缺点。
一种不需要使用光气的不同方法是基于BPA与碳酸二烷酯或碳酸二芳酯的酯基转移。使用碳酸二烷酯具有以下缺点:在与双酚丙酮的酯基转移中,其在商业上合理的条件下反应性不足以形成足量的聚合聚碳酸酯。此外,所释放的烷基醇并不用于制备聚碳酸酯的方法的任何其它部分,并且使烷基醇再循环到碳酸二烷酯制备需要实质性纯化。
使用碳酸二芳酯、尤其碳酸二苯酯(DPC)具有以下优点:其反应性足以形成聚合聚碳酸酯。此外,在碳酸二苯酯与双酚丙酮反应以形成聚碳酸酯时释放苯酚,例如如美国专利第5589564号中所描述。可以转而将这一苯酚再循环到双酚丙酮或碳酸二苯酯制备,在所述制备中苯酚是主要原料。碳酸二苯酯昂贵,并且希望找到在不因使用大量碳酸二苯酯而耗费大量成本的情况下执行这种方法的方式。制备聚碳酸酯的以上方法有足够的改进空间,特别是在使用的原料方面。
JP S64-16826描述一种制备聚碳酸酯的方法,其包含三个步骤。在第一步骤中,使双酚丙酮与碳酸二烷酯以1:1到1:100范围内的比率反应。这一反应产生双酚丙酮的二碳酸二烷酯,其接着与等摩尔或更大量的碳酸二苯酯反应以产生聚碳酸酯。在第三步骤中,使作为副产物产生的碳酸烷苯酯转化为碳酸二苯酯和碳酸二烷酯。
发明内容
本发明提供一种制备聚碳酸酯的方法,其包含使二羟基封端的碳酸酯和碳酸二芳酯在反应区中在聚合催化剂存在下在聚合条件下接触以产生聚碳酸酯。
具体实施方式
本发明提供一种新的形成聚碳酸酯的方式。所述方法包含使二羟基封端的碳酸酯与碳酸二芳酯接触。二羟基封端的碳酸酯可以是例如在每一末端上具有BPA分子的碳酸酯,并且碳酸二芳酯可以是碳酸二苯酯。这使得可通过使用与类似已知方法相比较少的碳酸二芳酯制备聚碳酸酯,因为使用二羟基封端的碳酸酯需要提供较少的碳酸二芳酯。
二羟基封端的碳酸酯是在每一末端上具有二羟基化合物的碳酸酯。二羟基化合物可以是脂肪族二醇、酸或二羟基芳香族化合物。二羟基封端的碳酸酯可以具有式I。
二羟基封端的碳酸酯可以通过使二羟基化合物与碳酸二烷酯反应形成。每一末端上的二羟基化合物将对应于这个反应中使用的二羟基化合物并且碳酸酯部分将对应于这个反应中使用的碳酸二烷酯。
用以形成二羟基封端的碳酸酯的二羟基化合物可以包含一种或多种脂肪族二醇。适合脂肪族二醇的实施例包括:异山梨糖醇;1,4:3,6-双去水-D-山梨糖醇;三环癸烷-二甲醇;4,8-双(羟甲基)三环癸烷;四甲基环丁二醇;2,2,4,4-四甲基环丁烷-1,3-二醇;顺式/反式-1,4-环己烷二甲醇;环己-1,4-烯二甲醇;反式-1,4-环己烷二甲醇;反式-1,4-双(羟甲基)环己烷;顺式-1,4-环己烷二甲醇;顺式-1,4-双(羟甲基)环己烷;顺式-1,2-环己烷二甲醇;1,1'-双(环己基)-4,4'-二醇;二环己基-4,4'-二醇;4,4'-二-羟基双环己基;和聚(乙二醇)。
用以形成二羟基封端的碳酸酯的二羟基化合物可以包含一种或多种酸。适合酸的实施例包括:1,10-十二烷酸;己二酸(adipic acid);己二酸(hexanedioic acid);间苯二甲酸;1,3-苯二甲酸;对苯二甲酸;1,4-苯二甲酸;2,6-萘二甲酸;3-羟基苯甲酸;和4-羟基苯甲酸。
用以形成二羟基封端的碳酸酯的二羟基化合物可以包含一种或多种二羟基芳香族化合物。二羟基芳香族化合物是在一个或多个芳环上包含两个羟基的芳香族化合物。二羟基芳香族化合物的实例包括双酚,例如BPA,其是优选的二羟基芳香族化合物;和二羟基苯,例如间苯二酚。
二羟基芳香族化合物可以是具有一个或多个卤素、硝基、氰基、烷基或环烷基的双酚。适合双酚的实施例包括2,2-双(4-羟苯基)丙烷(BPA);2,2-双(3-氯-4-羟苯基)丙烷;2,2-双(3-溴-4-羟苯基)丙烷;2,2-双(4-羟基-3-甲基苯基)丙烷;2,2-双(4-羟基-3-异丙基苯基)丙烷;2,2-双(3-叔丁基-4-羟苯基)丙烷;2,2-双(3-苯基-4-羟苯基)丙烷;2,2-双(3,5-二氯-4-羟苯基)丙烷;2,2-双(3,5-二溴-4-羟苯基)丙烷;2,2-双(3,5-二甲基-4-羟苯基)丙烷;2,2-双(3-氯-4-羟基-5-甲基苯基)丙烷;2,2-双(3-溴-4-羟基-5-甲基苯基)丙烷;2,2-双(3-氯-4-羟基-5-异丙基苯基)丙烷;2,2-双(3-溴-4-羟基-5-异丙基苯基)丙烷;2,2-双(3-叔丁基-5-氯-4-羟苯基)丙烷;2,2-双(3-溴-5-叔丁基-4-羟苯基)丙烷;2,2-双(3-氯-5-苯基-4-羟苯基)丙烷;2,2-双(3-溴-5-苯基-4-羟苯基)丙烷;2,2-双(3,5-二-异丙基-1-4-羟苯基)丙烷;2,2-双(3,5-二-叔丁基-4-羟苯基)丙烷;2,2-双(3,5-二苯基-4-羟苯基)丙烷;2,2-双(4-羟基-2,3,5,6-四氯苯基)丙烷;2,2-双(4-羟基-2,3,5,6-四溴苯基)丙烷;2,2-双(4-羟基-2,3,5,6-四甲基苯基)丙烷;2,2-双(2,6-二氯-3,5-二甲基-4-羟苯基)丙烷;2,2-双(2,6-二溴-3,5-二甲基-4-羟苯基)丙烷;1,1-双(4-羟苯基)环己烷;1,1-双(3-氯-4-羟苯基)环己烷;1,1-双(3-溴-4-羟苯基)环己烷;1,1-双(4-羟基-3-甲基苯基)环己烷;1,1-双(4-羟基-3-异丙基苯基)环己烷;1,1-双(3-叔丁基-4-羟苯基)环己烷;1,1-双(3-苯基-4-羟苯基)环己烷;1,1-双(3,5-二氯-4-羟苯基)环己烷;1,1-双(3,5-二溴-4-羟苯基)环己烷;1,1-双(3,5-二甲基-4-羟苯基)环己烷;1,1-双(3-氯-4-羟基-5-甲基苯基)环己烷;1,1-双(3-溴-4-羟基-5-甲基苯基)环己烷;1,1-双(3-氯-4-羟基-5-异丙基苯基)环己烷;1,1-双(3-溴-4-羟基-5-异丙基苯基)环己烷;1,1-双(3-叔丁基-5-氯-4-羟苯基)环己烷;1,1-双(3-溴-5-叔丁基-4-羟苯基)环己烷;1,1-双(3-氯-5-苯基-4-羟苯基)环己烷;1,1-双(3-溴-5-苯基-4-羟苯基)环己烷;1,1-双(3,5-二异丙基-4-羟苯基)环己烷;1,1-双(3,5-二-叔丁基-4-羟苯基)环己烷;1,1-双(3,5-二苯基-4-羟苯基)环己烷;1,1-双(4-羟基-2,3,5,6-四氯苯基)环己烷;1,1-双(4-羟基-2,3,5,6-四溴苯基)环己烷;1,1-双(4-羟基-2,3,5,6-四甲基苯基)环己烷;1,1-双(2,6-二氯-3,5-二甲基-4-羟苯基)环己烷;1,1-双(2,6-二溴-3,5-二甲基-4-羟苯基)环己烷;1,1-双(4-羟苯基)-3,3,5-三甲基环己烷;1,1-双(3-氯-4-羟苯基)-3,3,5-三甲基环己烷;1,1-双(3-溴-4-羟苯基)-3,3,5-三甲基环己烷;1,1-双(4-羟基-3-甲基苯基)-3,3,5-三甲基环己烷;1,1-双(4-羟基-3-异丙基苯基)-3,3,5-三甲基环己烷;1,1-双(3-叔丁基-4-羟苯基)-3,3,5-三甲基环己烷;1,1-双(3-苯基-4-羟苯基)-3,3,5-三甲基环己烷;1,1-双(3,5-二氯-4-羟苯基)-3,3,5-三甲基环己烷;1,1-双(3,5-二溴-4-羟苯基)-3,3,5-三甲基环己烷;1,1-双(3,5-二甲基-4-羟苯基)-3,3,5-三甲基环己烷;1,1-双(3-氯-4-羟基-5-甲基苯基)-3,3,5-三甲基环己烷;1,1-双(3-溴-4-羟基-5-甲基苯基)-3,3,5-三甲基环己烷;1,1-双(3-氯-4-羟基-5-异丙基苯基)-3,3,5-三甲基环己烷;1,1-双(3-溴-4-羟基-5-异丙基苯基)-3,3,5-三甲基环己烷;1,1-双(3-叔丁基-5-氯-4-羟苯基)-3,3,5-三甲基环己烷;1,1-双(3-溴-5-叔丁基-4-羟苯基)-3,3,5-三甲基环己烷;双(3-氯-5-苯基-4-羟苯基)-3,3,5-三甲基环己烷;1,1-双(3-溴-5-苯基-4-羟苯基)-3,3,5-三甲基环己烷;1,1-双(3,5-二-异丙基-4-羟苯基)-3,3,5-三甲基环己烷;1,1-双(3,5-二-叔丁基-4-羟苯基)-3,3,5-三甲基环己烷;1,1-双(3,5-二苯基-4-羟苯基)-3,3,5-三甲基环己烷;1,1-双(4-羟基-2,3,5,6-四氯苯基)-3,3,5-三甲基环己烷;1,1-双(4-羟基-2,3,5,6-四溴苯基)-3,3,5-三甲基环己烷;1,1-双(4-羟基-2,3,5,6-四甲基苯基)-3,3,5-三甲基环己烷;1,1-双(2,6-二氯-3,5-二甲基-4-羟苯基)-3,3,5-三甲基环己烷;1,1-双(2,6-二溴-3,5-二甲基-4-羟苯基)-3,3,5-三甲基环己烷;4,4'-二羟基-1,1-联苯;4,4'-二羟基-3,3'-二甲基-1,1-联苯;4,4'-二羟基-3,3'-二辛基-1,1-联苯;4,4'-二羟基二苯醚;4,4'-二羟基二苯硫醚;1,3-双(2-(4-羟苯基)-2-丙基)苯;1,3-双(2-(4-羟基-3-甲基苯基)-2-丙基)苯;1,4-双(2-(4-羟苯基)-2-丙基)苯和1,4-双(2-(4-羟基-3-甲基苯基)-2-丙基)苯。
适合二羟基苯的实施例包括氢醌、间苯二酚、甲基氢醌、丁基氢醌、苯基氢醌、4-苯基间苯二酚和4-甲基间苯二酚。
适合二羟基萘的实施例包括2,6-二羟基萘;2,6-二羟基-3-甲基萘;2,6-二羟基-3-苯基萘;1,4-二羟基萘;1,4-二羟基-2-甲基萘;1,4-二羟基-2-苯基萘;和1,3-二羟基萘。
在一个实施例中,碳酸二烷酯由式R1OCOOR1表示。在另一实施例中,碳酸二烷酯由式R1OCOOR2表示。R1和R2表示具有1到10个碳原子的烷基、具有3到10个碳原子的脂环基或具有6到10个碳原子的芳烷基。R1和R2的实例包括烷基,如甲基、乙基、丙基、烯丙基、丁基、丁烯基、戊基、己基、庚基、辛基、壬基、癸基和环己基甲基和其异构体。R1和R2的其它实例包括脂环基,如环丙基、环丁基、环戊基、环己基和环庚基;和芳烷基,如苯甲基、苯乙基、苯丙基、苯丁基、甲基苯甲基和其异构体。
烷基、脂环基或芳烷基可以被如低碳烷基、低碳烷氧基、氰基和卤素原子的取代基取代。
烷基相同的碳酸二烷酯的实例是碳酸二甲酯、碳酸二乙酯、碳酸二丙酯、碳酸二烯丙酯、碳酸二丁烯酯、碳酸二丁酯、碳酸二戊酯、碳酸二己酯、碳酸二庚酯、碳酸二辛酯、碳酸二壬酯、碳酸二癸酯、碳酸二环戊酯、碳酸二环己酯、碳酸二环庚酯和其异构体。
烷基不同的碳酸二烷酯的实例是碳酸甲乙酯、碳酸甲丙酯、碳酸甲丁酯、碳酸甲丁烯酯、碳酸甲戊酯、碳酸甲己酯、碳酸甲庚酯、碳酸甲辛酯、碳酸甲壬酯和碳酸甲癸酯和其异构体。其它实例包括具有1到10个碳原子的烷基的任何组合,例如碳酸乙丙酯、碳酸乙丁酯、碳酸丙丁酯和其异构体。
R1和/或R2是具有四个或更少碳原子的烷基的碳酸二烷酯是优选的。碳酸二烷酯最优选是碳酸二乙酯。
碳酸二烷酯可以通过本领域普通技术人员已知的任何方法来制备。举例来说,碳酸二烷酯可以通过US 7763745中描述的方法来制备,其中将碳酸烷二酯和烷醇原料引入反应区中以在酯基转移催化剂存在下反应以得到富含烷二醇的物料流和包含碳酸二烷酯和烷醇的物料流,通过一个或多个步骤分离所述物料流以产生富含碳酸二烷酯的物料流。
这些反应物的反应中使用的聚合催化剂可以是非均相或均相的。在另一实施例中,可以使用非均相和均相催化剂。
催化剂可以包括碱金属(即,锂、钠、钾、铷和铯)的氢化物、氧化物、氢氧化物、醇盐、酰胺或盐。催化剂可以是钾或钠的氢氧化物或醇盐。其它适合催化剂是碱金属盐,例如乙酸盐、丙酸盐、丁酸盐或碳酸盐,例如乙酸钠。另外,可以使用乙二胺四乙酸的衍生物,如EDTA四钠盐和EDTA镁二钠盐和其组合。其它适合催化剂包含碱土金属离子源,例如氢氧化镁或氢氧化钙或其混合物。
催化剂可以包含非挥发性无机酸的一种或多种盐,例如非挥发性无机酸的盐,如NaH2PO3、NaH2PO4、KH2PO4、CsH2PO4、Cs2H2PO4或其混合物。或者,催化剂可以包含磷酸的一种或多种混合碱金属盐,如NaKHPO4、CsNaHPO4、CsKHPO4和其混合物。
其它适合催化剂包括膦、胂或二价硫化合物和硒化合物和其鎓盐。这种类型的催化剂的实例包括三丁基膦;三苯基膦;二苯基膦;1,3-双(二苯基膦基)丙烷;三苯基胂;三甲基胂;三丁基胂;1,2-双(二苯基胂)乙烷;三苯基锑;二苯硫醚;二苯二硫醚;二苯基硒;四苯基鏻卤化物(Cl、Br、I);四苯基鉮卤化物(Cl、Br、I);三苯基锍卤化物(Cl、Br、I)。催化剂可以包含季铵化合物、季鏻化合物或其组合。举例来说,催化剂可以包含四甲基氢氧化鏻、四甲基乙酸鏻、四甲基甲酸鏻、四丁基氢氧化鏻、四丁基乙酸鏻、四苯基乙酸鏻、四苯基苯酚鏻和其组合。
其它适合催化剂包括锡、钛或锆的络合物或盐。这种类型的催化剂的实例包括丁基锡酸;甲醇锡;二甲基锡;氧化二丁基锡;二月桂酸二丁基锡;氢化三丁基锡;氯化三丁基锡;乙基己酸锡(II);锆醇盐(甲基、乙基或丁基);锆(IV)卤化物(F、Cl、Br、I);硝酸锆;乙酰基丙酮酸锆;钛醇盐(甲基、乙基或异丙基);乙酸钛;乙酰基丙酮酸钛。
催化剂可以是含有适合官能团的离子交换树脂,所述官能团例如叔胺基、季铵基、磺酸基和羧酸基。催化剂可以是碱金属或碱土金属硅酸盐。催化剂可以包含来自元素周期表的第4族(如钛)、第5族(如钒)、第6族(如铬或钼)或第12族(如锌)的元素,或锡或铅,或此类元素的组合,如锌与铬的组合(例如亚铬酸锌)。这些元素可以氧化物(如氧化锌)形式存在于催化剂中。
催化剂可以选自由以下组成的群组:氢氧化钠、碳酸钠、氢氧化锂、碳酸锂、四烷基氢氧化铵、四烷基碳酸铵、钛醇盐、铅醇盐、锡醇盐和铝磷酸盐。
二羟基封端的碳酸酯与碳酸二芳酯的接触可以在分批、半分批或连续反应步骤中进行。聚合反应可以在任何类型的反应器中执行,所述反应器例如分批反应器、具有真空抽取的分批反应器、具有蒸馏塔的分批反应器或催化蒸馏塔。反应优选于在反应期间提供醇移出的反应器中执行。反应是平衡反应,并且醇移出使平衡有利于所需产物偏移。
在催化或反应蒸馏塔中,反应在反应物和产物进行分离的相同位置进行。在这种塔中,存在可以被定义为反应蒸馏塔的存在催化剂的部分的反应区。这种催化剂可以是均相或非均相的。
反应可以在其操作周期不同步操作的多个分批反应器中执行。以这种方式,产物将连续产生并且任何其它反应步骤可以连续执行。
在半分批操作的一实施例中,二羟基封端的碳酸酯、碳酸二芳酯和催化剂可以组合于搅拌锅反应器中。反应器可以连接到蒸馏设备,所述蒸馏设备移出作为反应的一部分形成的醇。在另一实施例中,汽提气体可以用以促进醇的移出。这使平衡朝着产物偏移并且改进反应性能。如果碳酸二芳酯通过蒸馏设备移出,那么其可以再循环到反应器。
根据一优选实施例,当二羟基封端的碳酸酯是二-双酚丙酮-碳酸酯并且碳酸二芳酯是碳酸二苯酯时,总反应展示如下:
在这个实施例中,聚合反应产生高碳寡聚物并且最终形成聚碳酸酯。反应还产生苯酚,其可以再循环到制备碳酸二苯酯或二羟基芳香族化合物的步骤。
聚合反应条件类似于用于使用双酚丙酮和碳酸二苯酯制备聚碳酸酯的条件。可以调整反应步骤的聚合条件以便移出形成的醇并且也确保充足反应速率。如果温度过高或压力过低,那么反应物可能通过蒸馏设备被带出反应区或可能促进副反应。
聚合优选在小于2.03MPa的压力下执行。压力优选在0.01kPa到2.03MPa、优选0.1kPa到50kPa范围内。聚合优选在170℃到350℃、优选190℃到320℃范围内的温度下执行。
可以随着反应进行而改变反应器条件。最初,温度和压力需要使得温度高到足以驱动反应并且蒸发形成的任何醇。在一个实施例中,聚合反应在190℃到320℃范围内的温度下在极低压力(例如0.1kPa)下执行。温度最初在这个范围的下端,并且随着反应进行,温度逐渐升高。压力最初在20kPa下,并且逐渐降低到0.1kPa。反应后期的温度需要高到足以维持聚合物的足够高的熔体流动,所述聚合物随着聚合进行而变得粘性更大。温度不应过高,因为其还会导致非所需副反应。压力需要低到足以从这个粘性熔体移出反应中形成的苯酚。
在聚合过程开始后,可以使反应物通过多个串联反应器。二羟基封端的碳酸酯与碳酸二苯酯最初接触之后的步骤可以按类似于任何已知熔融聚碳酸酯方法的方法进行。这包括设计和操作反应器,和使用赋予所得聚碳酸酯以可用特性的添加剂。
因为起始材料已经在二羟基封端的碳酸酯中包含碳酸酯部分,所以需要较少碳酸二芳酯。如果使用纯二羟基封端的碳酸酯流,那么每一摩尔二羟基封端的碳酸酯需要一摩尔碳酸二芳酯。二羟基封端的碳酸酯与碳酸二芳酯的优选摩尔比在1:2到2:1范围内。
如果添加略微过量的二羟基封端的碳酸酯所述碳酸二芳酯到反应器,那么所得聚碳酸酯将以相应化合物中的一种或另一种封端。另外,可以添加已知可用于聚碳酸酯制备的任何添加剂或其它组分到聚合反应。
制备熔融聚碳酸酯的常规途径典型地使1摩尔碳酸二苯酯与1摩尔BPA反应。本文所描述的反应典型地包含使1摩尔碳酸二苯酯与1摩尔二羟基封端的碳酸酯反应。因此,在这个反应中,1/2摩尔碳酸二苯酯用以与1摩尔BPA反应。
如果二羟基封端的碳酸酯流含有杂质,例如来自二羟基封端的碳酸酯制造的二羟基芳香族化合物,那么这些杂质也可以被转化,但将需要另外的碳酸二芳酯。
在反应期间可以形成醇。举例来说,如果碳酸二苯酯用作碳酸二芳酯,那么将形成苯酚。另外,可以形成其它副产物,包括起始材料的异构体,和来自傅瑞斯重排(Friesrearrangement)的支化聚碳酸酯链。
实例
实例1
在这个实例中,将约24.5g二-双酚丙酮-碳酸酯(50.8mmol)和6.5gBPA(28.5mmol)的混合物与17.8g DPC(83.3mmol)混合,使其在10ppm氢氧化锂存在下聚合。聚合以分批真空蒸馏设置执行:200ml玻璃圆底烧瓶,配备有机械搅拌设备(包括铁氟龙搅拌桨叶)、精确压力控制器和加热套,以及顶置式接受器。首先将反应混合物在200℃下在300毫巴下加热2小时,并且接着经15分钟时间段使温度缓慢斜变到260℃并且将压力降低到0.5毫巴。随后使聚合条件保持在260℃/0.5毫巴下1小时。分子分析显示,聚合物样品的Mn是13000。
Claims (11)
1.一种制备聚碳酸酯的方法,其包含使二羟基封端的碳酸酯和碳酸二芳酯在反应区中在聚合催化剂存在下在聚合条件下接触以产生聚碳酸酯,其中所述二羟基封端的碳酸酯是在每一末端上具有二羟基化合物的碳酸酯,所述二羟基封端的碳酸酯是通过使二羟基化合物与碳酸二烷酯反应形成,并且所述二羟基化合物是二羟基芳香族化合物。
2.根据权利要求1所述的方法,其中所述二羟基封端的碳酸酯是二-双酚丙酮-碳酸酯化合物。
3.根据权利要求1到2中任一项所述的方法,其中所述碳酸二芳酯是碳酸二苯酯。
4.根据权利要求1到2中任一项所述的方法,其中所述反应区中所述二羟基封端的碳酸酯与碳酸二芳酯的摩尔比是1:2到2:1。
5.根据权利要求1到2中任一项所述的方法,其中在所述反应区中存在第二二羟基化合物。
6.根据权利要求5所述的方法,其中所述第二二羟基化合物在单独反应中用以形成所述二羟基封端的碳酸酯。
7.根据权利要求1到2中任一项所述的方法,其中所述聚合条件包含小于2.03 kPA的压力。
8.根据权利要求1到2中任一项所述的方法,其中所述聚合条件包含170到350℃范围内的温度。
9.根据权利要求1到2中任一项所述的方法,其中所述聚合条件包含190到320℃范围内的温度。
10.根据权利要求1到2中任一项所述的方法,其中所述聚合在多个反应器中执行。
11.根据权利要求1到2中任一项所述的方法,其进一步包含添加添加剂到所述反应区。
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