TW201127875A - Method for production of polycarbonate - Google Patents

Method for production of polycarbonate Download PDF

Info

Publication number: TW201127875A
Authority: TW; Taiwan
Prior art keywords: group; producing; compound; polycarbonate; fluorine
Prior art date: 2009-08-28

Application number

TW99128683A

Other languages

English (en)

Chinese (zh)

Inventor

Jumpei Nomura

Takashi Okazoe

Hidekazu Okamoto

Nobuyuki Kasahara

Kyoko Yamamoto

Original Assignee

Asahi Glass Co Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2009-08-28

Filing date

2010-08-26

Publication date

2011-08-16

2010-08-26 Application filed by Asahi Glass Co Ltd filed Critical Asahi Glass Co Ltd

2011-08-16 Publication of TW201127875A publication Critical patent/TW201127875A/zh

Links

239000004417 polycarbonate Substances 0.000 title claims abstract description 68
229920000515 polycarbonate Polymers 0.000 title claims abstract description 68
238000004519 manufacturing process Methods 0.000 title claims abstract description 36
229910052731 fluorine Inorganic materials 0.000 claims abstract description 70
238000000034 method Methods 0.000 claims abstract description 55
150000001875 compounds Chemical class 0.000 claims abstract description 45
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims abstract description 41
239000011737 fluorine Substances 0.000 claims abstract description 41
150000002009 diols Chemical class 0.000 claims abstract description 26
239000011968 lewis acid catalyst Substances 0.000 claims abstract description 16
125000003709 fluoroalkyl group Chemical group 0.000 claims abstract description 8
-1 alkoxide compound Chemical class 0.000 claims description 55
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 34
229910052799 carbon Inorganic materials 0.000 claims description 34
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 33
238000006243 chemical reaction Methods 0.000 claims description 33
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 28
229910052751 metal Inorganic materials 0.000 claims description 28
125000001153 fluoro group Chemical group F* 0.000 claims description 27
239000002184 metal Substances 0.000 claims description 27
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 17
239000001301 oxygen Substances 0.000 claims description 17
229910052760 oxygen Inorganic materials 0.000 claims description 17
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 claims description 15
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 14
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 12
239000007789 gas Substances 0.000 claims description 12
238000005809 transesterification reaction Methods 0.000 claims description 11
125000000524 functional group Chemical group 0.000 claims description 10
229910044991 metal oxide Inorganic materials 0.000 claims description 10
150000004706 metal oxides Chemical group 0.000 claims description 10
125000004429 atom Chemical group 0.000 claims description 9
239000000126 substance Substances 0.000 claims description 9
229910052718 tin Inorganic materials 0.000 claims description 9
229910052719 titanium Inorganic materials 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 6
150000007524 organic acids Chemical group 0.000 claims description 6
150000001449 anionic compounds Chemical class 0.000 claims description 5
229910001412 inorganic anion Inorganic materials 0.000 claims description 5
239000000052 vinegar Substances 0.000 claims description 5
235000021419 vinegar Nutrition 0.000 claims description 5
150000002500 ions Chemical class 0.000 claims description 4
125000006551 perfluoro alkylene group Chemical group 0.000 claims description 4
229910052779 Neodymium Inorganic materials 0.000 claims description 3
229910052746 lanthanum Inorganic materials 0.000 claims description 3
239000007858 starting material Substances 0.000 claims description 3
229910052726 zirconium Inorganic materials 0.000 claims description 3
229910052769 Ytterbium Inorganic materials 0.000 claims description 2
150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
229910052745 lead Inorganic materials 0.000 claims description 2
229910052710 silicon Inorganic materials 0.000 claims description 2
125000001183 hydrocarbyl group Chemical group 0.000 claims 2
QSHKLJKIMMLDGE-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5-decafluorocyclohexane Chemical compound FC1(F)CC(F)(F)C(F)(F)C(F)(F)C1(F)F QSHKLJKIMMLDGE-UHFFFAOYSA-N 0.000 claims 1
SXFJDZNJHVPHPH-UHFFFAOYSA-N 3-methylpentane-1,5-diol Chemical compound OCCC(C)CCO SXFJDZNJHVPHPH-UHFFFAOYSA-N 0.000 claims 1
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical group [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims 1
239000002841 Lewis acid Substances 0.000 claims 1
229930182558 Sterol Natural products 0.000 claims 1
150000001298 alcohols Chemical class 0.000 claims 1
150000001335 aliphatic alkanes Chemical class 0.000 claims 1
229910052786 argon Inorganic materials 0.000 claims 1
LRHPLDYGYMQRHN-UHFFFAOYSA-N butyl alcohol Substances CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 1
230000000739 chaotic effect Effects 0.000 claims 1
229930004069 diterpene Natural products 0.000 claims 1
150000004141 diterpene derivatives Chemical class 0.000 claims 1
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 1
150000007517 lewis acids Chemical class 0.000 claims 1
150000002739 metals Chemical class 0.000 claims 1
125000005010 perfluoroalkyl group Chemical group 0.000 claims 1
239000011148 porous material Substances 0.000 claims 1
150000003432 sterols Chemical class 0.000 claims 1
235000003702 sterols Nutrition 0.000 claims 1
229910052727 yttrium Inorganic materials 0.000 claims 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract description 14
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract description 7
231100000167 toxic agent Toxicity 0.000 abstract description 5
239000003440 toxic substance Substances 0.000 abstract description 5
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 16
239000003054 catalyst Substances 0.000 description 14
239000002585 base Substances 0.000 description 13
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 10
DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 10
229910021653 sulphate ion Inorganic materials 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
230000009257 reactivity Effects 0.000 description 8
239000010936 titanium Substances 0.000 description 8
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 7
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 7
239000002253 acid Substances 0.000 description 7
125000001931 aliphatic group Chemical group 0.000 description 7
238000010494 dissociation reaction Methods 0.000 description 7
230000005593 dissociations Effects 0.000 description 7
230000015572 biosynthetic process Effects 0.000 description 6
239000002904 solvent Substances 0.000 description 6
238000004458 analytical method Methods 0.000 description 5
125000003118 aryl group Chemical group 0.000 description 5
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 5
238000006068 polycondensation reaction Methods 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 4
238000009835 boiling Methods 0.000 description 4
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 4
230000000694 effects Effects 0.000 description 4
238000005227 gel permeation chromatography Methods 0.000 description 4
239000002994 raw material Substances 0.000 description 4
239000002689 soil Substances 0.000 description 4
150000004703 alkoxides Chemical class 0.000 description 3
FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 description 3
238000004040 coloring Methods 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 3
238000004821 distillation Methods 0.000 description 3
238000004817 gas chromatography Methods 0.000 description 3
239000008267 milk Substances 0.000 description 3
210000004080 milk Anatomy 0.000 description 3
235000013336 milk Nutrition 0.000 description 3
238000006116 polymerization reaction Methods 0.000 description 3
238000007086 side reaction Methods 0.000 description 3
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 3
DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 2
YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
NBUKAOOFKZFCGD-UHFFFAOYSA-N 2,2,3,3-tetrafluoropropan-1-ol Chemical compound OCC(F)(F)C(F)F NBUKAOOFKZFCGD-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
229910014033 C-OH Inorganic materials 0.000 description 2
229910014570 C—OH Inorganic materials 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
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
NVRXCHOLZBQSNZ-UHFFFAOYSA-I [V+5].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F Chemical compound [V+5].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F NVRXCHOLZBQSNZ-UHFFFAOYSA-I 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 2
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 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
YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
125000006612 decyloxy group Chemical group 0.000 description 2
238000001514 detection method Methods 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 2
150000002430 hydrocarbons Chemical group 0.000 description 2
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N isopropyl alcohol Natural products CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
229910052744 lithium Inorganic materials 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
229910052987 metal hydride Inorganic materials 0.000 description 2
150000004681 metal hydrides Chemical class 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
229960005235 piperonyl butoxide Drugs 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
229920000166 polytrimethylene carbonate Polymers 0.000 description 2
229920002635 polyurethane Polymers 0.000 description 2
239000004814 polyurethane Substances 0.000 description 2
230000001737 promoting effect Effects 0.000 description 2
238000000746 purification Methods 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 2
CVAWJXNMZZBMQP-UHFFFAOYSA-N trifluorosulfanium Chemical compound F[S+](F)F CVAWJXNMZZBMQP-UHFFFAOYSA-N 0.000 description 2
229910052725 zinc Inorganic materials 0.000 description 2
239000011701 zinc Substances 0.000 description 2
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
QTDAXPXRSUIMFH-UHFFFAOYSA-N 1,1,1,2-tetramethoxydecane Chemical compound COC(C(OC)(OC)OC)CCCCCCCC QTDAXPXRSUIMFH-UHFFFAOYSA-N 0.000 description 1
BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 description 1
NSGXIBWMJZWTPY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)CC(F)(F)F NSGXIBWMJZWTPY-UHFFFAOYSA-N 0.000 description 1
WLAYYZWRSCELHE-UHFFFAOYSA-N 1,1,2,2,3,3,4,4-octafluorocyclohexane Chemical compound FC1(F)CCC(F)(F)C(F)(F)C1(F)F WLAYYZWRSCELHE-UHFFFAOYSA-N 0.000 description 1
KUGBQWBWWNPMIT-UHFFFAOYSA-N 1,1,2,2,3,3,4,4-octafluoropentan-1-ol Chemical compound CC(F)(F)C(F)(F)C(F)(F)C(O)(F)F KUGBQWBWWNPMIT-UHFFFAOYSA-N 0.000 description 1
UYZQWKKNVBJVOF-UHFFFAOYSA-N 1-decoxytetradecane Chemical compound CCCCCCCCCCCCCCOCCCCCCCCCC UYZQWKKNVBJVOF-UHFFFAOYSA-N 0.000 description 1
LPJITDYKVUMUHL-UHFFFAOYSA-N 1-fluorobutan-1-ol Chemical compound CCCC(O)F LPJITDYKVUMUHL-UHFFFAOYSA-N 0.000 description 1
MSWVMWGCNZQPIA-UHFFFAOYSA-N 1-fluoropropan-2-one Chemical compound CC(=O)CF MSWVMWGCNZQPIA-UHFFFAOYSA-N 0.000 description 1
VOGSDFLJZPNWHY-UHFFFAOYSA-N 2,2-difluoroethanol Chemical compound OCC(F)F VOGSDFLJZPNWHY-UHFFFAOYSA-N 0.000 description 1
LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
JBMBVWROWJGFMG-UHFFFAOYSA-N 2-chloro-7h-purine Chemical compound ClC1=NC=C2NC=NC2=N1 JBMBVWROWJGFMG-UHFFFAOYSA-N 0.000 description 1
WKXZJCKWUCBECD-UHFFFAOYSA-N 2-fluoropropan-1-ol Chemical compound CC(F)CO WKXZJCKWUCBECD-UHFFFAOYSA-N 0.000 description 1
QVHDXWUPMHCPMN-UHFFFAOYSA-N 2-sulfanylpentane-2,4-diol Chemical compound SC(C)(CC(C)O)O QVHDXWUPMHCPMN-UHFFFAOYSA-N 0.000 description 1
VHOMQNUWCMBKFN-UHFFFAOYSA-N 3,3,3-trifluoropropane-1,1-diol Chemical compound OC(O)CC(F)(F)F VHOMQNUWCMBKFN-UHFFFAOYSA-N 0.000 description 1
VSUXHHFVKHGSRE-UHFFFAOYSA-N 4,4-dibutoxyoxane Chemical compound CCCCOC1(CCOCC1)OCCCC VSUXHHFVKHGSRE-UHFFFAOYSA-N 0.000 description 1
NZGQHKSLKRFZFL-UHFFFAOYSA-N 4-(4-hydroxyphenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(O)C=C1 NZGQHKSLKRFZFL-UHFFFAOYSA-N 0.000 description 1
ICYDRUIZSPKQOH-UHFFFAOYSA-N 4-[1-(4-hydroxyphenyl)decyl]phenol Chemical compound C=1C=C(O)C=CC=1C(CCCCCCCCC)C1=CC=C(O)C=C1 ICYDRUIZSPKQOH-UHFFFAOYSA-N 0.000 description 1
229930185605 Bisphenol Natural products 0.000 description 1
FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 1
ZTCZAUDSJOHCAM-UHFFFAOYSA-N C(CCC)O[Ru] Chemical compound C(CCC)O[Ru] ZTCZAUDSJOHCAM-UHFFFAOYSA-N 0.000 description 1
GGGAJYDNOBDTIX-UHFFFAOYSA-N C(CCCC)OC(C(OCCCCC)(OCCCCC)OCCCCC)CCCCCCCC Chemical compound C(CCCC)OC(C(OCCCCC)(OCCCCC)OCCCCC)CCCCCCCC GGGAJYDNOBDTIX-UHFFFAOYSA-N 0.000 description 1
SNTPTBDZONUGKE-UHFFFAOYSA-N C(CCCCCCCCCC)O[Ti](OCCCCCCCCCCC)(OCCCCCCCCCCC)OCCCCCCCCCCC Chemical compound C(CCCCCCCCCC)O[Ti](OCCCCCCCCCCC)(OCCCCCCCCCCC)OCCCCCCCCCCC SNTPTBDZONUGKE-UHFFFAOYSA-N 0.000 description 1
AXYVQTVQLNCBHW-UHFFFAOYSA-N C(CCCCCCCCCCCCC)O[Sn] Chemical compound C(CCCCCCCCCCCCC)O[Sn] AXYVQTVQLNCBHW-UHFFFAOYSA-N 0.000 description 1
BQPSJZBGALPINC-UHFFFAOYSA-N C(CCCCCCCCCCCCC)O[Ti](OCCCCCCCCCCCCCC)(OCCCCCCCCCCCCCC)OCCCCCCCCCCCCCC Chemical compound C(CCCCCCCCCCCCC)O[Ti](OCCCCCCCCCCCCCC)(OCCCCCCCCCCCCCC)OCCCCCCCCCCCCCC BQPSJZBGALPINC-UHFFFAOYSA-N 0.000 description 1
VXJWGFNTZMWKJU-UHFFFAOYSA-N CCCCCCCCCCCCCCO[Ti] Chemical compound CCCCCCCCCCCCCCO[Ti] VXJWGFNTZMWKJU-UHFFFAOYSA-N 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
YECOTGLJPABYBJ-UHFFFAOYSA-N FC(S(=O)(=O)C=1C(=C2C(C(=O)NC2=O)=CC1)S(=O)(=O)C(F)(F)F)(F)F.[Li] Chemical compound FC(S(=O)(=O)C=1C(=C2C(C(=O)NC2=O)=CC1)S(=O)(=O)C(F)(F)F)(F)F.[Li] YECOTGLJPABYBJ-UHFFFAOYSA-N 0.000 description 1
DOJXGHGHTWFZHK-UHFFFAOYSA-N Hexachloroacetone Chemical compound ClC(Cl)(Cl)C(=O)C(Cl)(Cl)Cl DOJXGHGHTWFZHK-UHFFFAOYSA-N 0.000 description 1
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 1
238000012696 Interfacial polycondensation Methods 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
235000009411 Rheum rhabarbarum Nutrition 0.000 description 1
241000219063 Rheum rhabarbarum [NCBITaxon:3621] Species 0.000 description 1
241000245165 Rhododendron ponticum Species 0.000 description 1
240000004808 Saccharomyces cerevisiae Species 0.000 description 1
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
239000007983 Tris buffer Substances 0.000 description 1
QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
DQMGZCOKSYOUNY-UHFFFAOYSA-N [O].C1=CC=CC2=CC3=CC=CC=C3C=C21 Chemical compound [O].C1=CC=CC2=CC3=CC=CC=C3C=C21 DQMGZCOKSYOUNY-UHFFFAOYSA-N 0.000 description 1
OFQAOMFYQQFLFM-UHFFFAOYSA-N [Sn+4].CCCCCCCCCCC[O-].CCCCCCCCCCC[O-].CCCCCCCCCCC[O-].CCCCCCCCCCC[O-] Chemical compound [Sn+4].CCCCCCCCCCC[O-].CCCCCCCCCCC[O-].CCCCCCCCCCC[O-].CCCCCCCCCCC[O-] OFQAOMFYQQFLFM-UHFFFAOYSA-N 0.000 description 1
TVUZCYXAXZPGRN-UHFFFAOYSA-K [V].F[Sb](F)F Chemical compound [V].F[Sb](F)F TVUZCYXAXZPGRN-UHFFFAOYSA-K 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
125000003158 alcohol group Chemical group 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
229910052787 antimony Inorganic materials 0.000 description 1
229910052785 arsenic Inorganic materials 0.000 description 1
BXPKWRPAONPIBY-UHFFFAOYSA-N benzene copper(1+) Chemical compound [Cu+].C1=CC=CC=C1 BXPKWRPAONPIBY-UHFFFAOYSA-N 0.000 description 1
229910052790 beryllium Inorganic materials 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
239000004305 biphenyl Substances 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
VDLHKDQLOUOMTC-UHFFFAOYSA-N bis(2,2,3,3-tetrafluoropropyl) carbonate Chemical compound FC(F)C(F)(F)COC(=O)OCC(F)(F)C(F)F VDLHKDQLOUOMTC-UHFFFAOYSA-N 0.000 description 1
NYENCOMLZDQKNH-UHFFFAOYSA-K bis(trifluoromethylsulfonyloxy)bismuthanyl trifluoromethanesulfonate Chemical compound [Bi+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F NYENCOMLZDQKNH-UHFFFAOYSA-K 0.000 description 1
UCYRAEIHXSVXPV-UHFFFAOYSA-K bis(trifluoromethylsulfonyloxy)indiganyl trifluoromethanesulfonate Chemical compound [In+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F UCYRAEIHXSVXPV-UHFFFAOYSA-K 0.000 description 1
229910052797 bismuth Inorganic materials 0.000 description 1
JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
ZFVMWEVVKGLCIJ-UHFFFAOYSA-N bisphenol AF Chemical compound C1=CC(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C=C1 ZFVMWEVVKGLCIJ-UHFFFAOYSA-N 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
229950003621 butoxylate Drugs 0.000 description 1
DOBSQSLSWMMIEM-UHFFFAOYSA-N butoxytin Chemical compound CCCCO[Sn] DOBSQSLSWMMIEM-UHFFFAOYSA-N 0.000 description 1
MQWDTXAOPTYTLC-UHFFFAOYSA-N butyl 1-(3-cyano-3,3-diphenylpropyl)-4-phenylpiperidine-4-carboxylate Chemical compound C1CC(C(=O)OCCCC)(C=2C=CC=CC=2)CCN1CCC(C#N)(C=1C=CC=CC=1)C1=CC=CC=C1 MQWDTXAOPTYTLC-UHFFFAOYSA-N 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
125000005586 carbonic acid group Chemical group 0.000 description 1
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000007809 chemical reaction catalyst Substances 0.000 description 1
239000012295 chemical reaction liquid Substances 0.000 description 1
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
229940106681 chloroacetic acid Drugs 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000005034 decoration Methods 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
238000006392 deoxygenation reaction Methods 0.000 description 1
SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
LRBBIFXICMMTOW-UHFFFAOYSA-N dodecan-6-ol Chemical compound CCCCCCC(O)CCCCC LRBBIFXICMMTOW-UHFFFAOYSA-N 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
229910052732 germanium Inorganic materials 0.000 description 1
239000011521 glass Substances 0.000 description 1
229910052735 hafnium Inorganic materials 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
POIQBFKLCVMSME-UHFFFAOYSA-N hexadecan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCCCCCCCCCCCCCC[O-].CCCCCCCCCCCCCCCC[O-].CCCCCCCCCCCCCCCC[O-].CCCCCCCCCCCCCCCC[O-] POIQBFKLCVMSME-UHFFFAOYSA-N 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
230000007774 longterm Effects 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
BZQRBEVTLZHKEA-UHFFFAOYSA-L magnesium;trifluoromethanesulfonate Chemical compound [Mg+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F BZQRBEVTLZHKEA-UHFFFAOYSA-L 0.000 description 1
239000000463 material Substances 0.000 description 1
229910001507 metal halide Inorganic materials 0.000 description 1
150000005309 metal halides Chemical class 0.000 description 1
229910000000 metal hydroxide Inorganic materials 0.000 description 1
150000004692 metal hydroxides Chemical class 0.000 description 1
ITNVWQNWHXEMNS-UHFFFAOYSA-N methanolate;titanium(4+) Chemical compound [Ti+4].[O-]C.[O-]C.[O-]C.[O-]C ITNVWQNWHXEMNS-UHFFFAOYSA-N 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
239000012768 molten material Substances 0.000 description 1
229910052750 molybdenum Inorganic materials 0.000 description 1
125000001421 myristyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
150000002923 oximes Chemical class 0.000 description 1
SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
239000003444 phase transfer catalyst Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
229920000768 polyamine Polymers 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
230000035935 pregnancy Effects 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
150000003254 radicals Chemical group 0.000 description 1
230000036632 reaction speed Effects 0.000 description 1
238000011084 recovery Methods 0.000 description 1
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 1
229960001755 resorcinol Drugs 0.000 description 1
YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
239000000243 solution Substances 0.000 description 1
241000894007 species Species 0.000 description 1
238000010025 steaming Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000004575 stone Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
229920001059 synthetic polymer Polymers 0.000 description 1
229910052714 tellurium Inorganic materials 0.000 description 1
HFJFBZNPNYIFTE-UHFFFAOYSA-N tetradodecoxystannane Chemical compound [Sn+4].CCCCCCCCCCCC[O-].CCCCCCCCCCCC[O-].CCCCCCCCCCCC[O-].CCCCCCCCCCCC[O-] HFJFBZNPNYIFTE-UHFFFAOYSA-N 0.000 description 1
AEHYHWAFYINAOZ-UHFFFAOYSA-N tetraheptoxystannane Chemical compound CCCCCCCO[Sn](OCCCCCCC)(OCCCCCCC)OCCCCCCC AEHYHWAFYINAOZ-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
MTCVBFASLVCJSA-UHFFFAOYSA-N tetraoctoxystannane Chemical compound CCCCCCCCO[Sn](OCCCCCCCC)(OCCCCCCCC)OCCCCCCCC MTCVBFASLVCJSA-UHFFFAOYSA-N 0.000 description 1
XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
229910001887 tin oxide Inorganic materials 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
XPDWGBQVDMORPB-UHFFFAOYSA-N trifluoromethane acid Natural products FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 1
RPYBYGPNXCJANN-UHFFFAOYSA-N trifluoromethyltin Chemical compound FC(F)(F)[Sn] RPYBYGPNXCJANN-UHFFFAOYSA-N 0.000 description 1
WGIWBXUNRXCYRA-UHFFFAOYSA-H trizinc;2-hydroxypropane-1,2,3-tricarboxylate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O WGIWBXUNRXCYRA-UHFFFAOYSA-H 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
229940068475 zinc citrate Drugs 0.000 description 1
235000006076 zinc citrate Nutrition 0.000 description 1
239000011746 zinc citrate Substances 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
- C08G64/26—General preparatory processes using halocarbonates
- C08G64/266—General preparatory processes using halocarbonates and alcohols

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Polyesters Or Polycarbonates (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

TW99128683A 2009-08-28 2010-08-26 Method for production of polycarbonate TW201127875A (en)

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JP2009198478		2009-08-28

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TW99128683A TW201127875A (en)	2009-08-28	2010-08-26	Method for production of polycarbonate

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JP (1)	JPWO2011024732A1 (fr)
TW (1)	TW201127875A (fr)
WO (1)	WO2011024732A1 (fr)

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JP2015193674A (ja) *	2012-08-15	2015-11-05	旭硝子株式会社	ポリエステルカーボネートの製造方法
ES2788376T3 (es)	2013-04-16	2020-10-21	Agc Inc	Método de fabricación de policarbonato y policarbonato
JP2023061092A (ja) *	2021-10-19	2023-05-01	Ａｇｃ株式会社	ポリカーボネートポリオールの製造方法

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH06219992A (ja) *	1992-11-18	1994-08-09	Mitsui Petrochem Ind Ltd	新規な炭酸エステル化合物
IT1283647B1 (it) *	1996-08-02	1998-04-23	Ausimont Spa	Perfluoropolieteri a struttura di policarbonato
JP3246362B2 (ja) *	1996-11-27	2002-01-15	富士電機株式会社	電子写真用感光体
JP2005060261A (ja) *	2003-08-08	2005-03-10	Asahi Glass Co Ltd	ビス（２，２，３，４，４，４−ヘキサフルオロブチル）カーボネートおよびその製造方法、および非水系電解液
WO2005123656A1 (fr) *	2004-06-16	2005-12-29	Asahi Glass Company, Limited	Nouveaux carbonates de méthyle et procédé pour la production de ceux-ci et électrolyte non aqueux
US20060135662A1 (en) *	2004-12-22	2006-06-22	General Electric Company	Polycarbonates with fluoroalkylene carbonate end groups
WO2009123083A1 (fr) *	2008-03-31	2009-10-08	旭硝子株式会社	Procédé de fabrication de polycarbonate
TW201006795A (en) *	2008-06-30	2010-02-16	Asahi Glass Co Ltd	Process for producing diphenyl carbonate

2010
- 2010-08-20 JP JP2011528770A patent/JPWO2011024732A1/ja not_active Withdrawn
- 2010-08-20 WO PCT/JP2010/064118 patent/WO2011024732A1/fr not_active Ceased
- 2010-08-26 TW TW99128683A patent/TW201127875A/zh unknown

Also Published As

Publication number	Publication date
WO2011024732A1 (fr)	2011-03-03
JPWO2011024732A1 (ja)	2013-01-31

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