JP4856340B2 - ホスホニウムフェノレートの製造方法 - Google Patents
ホスホニウムフェノレートの製造方法 Download PDFInfo
- Publication number
- JP4856340B2 JP4856340B2 JP2001546614A JP2001546614A JP4856340B2 JP 4856340 B2 JP4856340 B2 JP 4856340B2 JP 2001546614 A JP2001546614 A JP 2001546614A JP 2001546614 A JP2001546614 A JP 2001546614A JP 4856340 B2 JP4856340 B2 JP 4856340B2
- Authority
- JP
- Japan
- Prior art keywords
- phosphonium
- phenolate
- phenol
- phosphonium phenolate
- reaction
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Fee Related
Links
- LVLZXBIWQHFREA-UHFFFAOYSA-N phenol;phosphane Chemical compound [PH4+].[O-]C1=CC=CC=C1 LVLZXBIWQHFREA-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 16
- -1 phosphonium halide Chemical class 0.000 claims abstract description 13
- 239000000203 mixture Substances 0.000 claims abstract description 10
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 4
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 4
- 239000012670 alkaline solution Substances 0.000 claims abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- 239000008367 deionised water Substances 0.000 claims description 10
- 239000012074 organic phase Substances 0.000 claims description 10
- 239000008346 aqueous phase Substances 0.000 claims description 8
- 239000012153 distilled water Substances 0.000 claims description 3
- 239000012044 organic layer Substances 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 13
- 238000002425 crystallisation Methods 0.000 abstract description 3
- 230000008025 crystallization Effects 0.000 abstract description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 12
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 12
- 229920000515 polycarbonate Polymers 0.000 description 11
- 239000004417 polycarbonate Substances 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 229910021641 deionized water Inorganic materials 0.000 description 8
- 238000005809 transesterification reaction Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 150000002989 phenols Chemical class 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 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 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 4
- 229940031826 phenolate Drugs 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000006085 branching agent Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- ZLLNYWQSSYUXJM-UHFFFAOYSA-M tetraphenylphosphanium;phenoxide Chemical compound [O-]C1=CC=CC=C1.C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 ZLLNYWQSSYUXJM-UHFFFAOYSA-M 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 125000006539 C12 alkyl 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])C([H])([H])C([H])([H])* 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- QCRFMSUKWRQZEM-UHFFFAOYSA-N cycloheptanol Chemical compound OC1CCCCCC1 QCRFMSUKWRQZEM-UHFFFAOYSA-N 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- FHADSMKORVFYOS-UHFFFAOYSA-N cyclooctanol Chemical compound OC1CCCCCCC1 FHADSMKORVFYOS-UHFFFAOYSA-N 0.000 description 2
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000013557 residual solvent Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 0.000 description 2
- 229920001169 thermoplastic Polymers 0.000 description 2
- 239000004416 thermosoftening plastic Substances 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
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- MTUCYAOJXPTLHZ-UHFFFAOYSA-N 1-cyclohexylbutan-1-ol Chemical compound CCCC(O)C1CCCCC1 MTUCYAOJXPTLHZ-UHFFFAOYSA-N 0.000 description 1
- JVTXOMXEPFDMHB-UHFFFAOYSA-N 1-cyclohexylpropan-1-ol Chemical compound CCC(O)C1CCCCC1 JVTXOMXEPFDMHB-UHFFFAOYSA-N 0.000 description 1
- JXLATLGQNUUYCG-UHFFFAOYSA-N 1-cyclopentylpropan-1-ol Chemical compound CCC(O)C1CCCC1 JXLATLGQNUUYCG-UHFFFAOYSA-N 0.000 description 1
- CAKWRXVKWGUISE-UHFFFAOYSA-N 1-methylcyclopentan-1-ol Chemical compound CC1(O)CCCC1 CAKWRXVKWGUISE-UHFFFAOYSA-N 0.000 description 1
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 1
- QJQZRLXDLORINA-UHFFFAOYSA-N 2-cyclohexylethanol Chemical compound OCCC1CCCCC1 QJQZRLXDLORINA-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229930185605 Bisphenol Chemical class 0.000 description 1
- 229910021580 Cobalt(II) chloride Inorganic materials 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 230000003139 buffering effect Effects 0.000 description 1
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- ISQVBYGGNVVVHB-UHFFFAOYSA-N cyclopentylmethanol Chemical compound OCC1CCCC1 ISQVBYGGNVVVHB-UHFFFAOYSA-N 0.000 description 1
- SZMNDOUFZGODBR-UHFFFAOYSA-N decan-5-ol Chemical compound CCCCCC(O)CCCC SZMNDOUFZGODBR-UHFFFAOYSA-N 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004870 electrical engineering Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000007730 finishing process Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/64—Preparation of O-metal compounds with O-metal group bound to a carbon atom belonging to a six-membered aromatic ring
- C07C37/66—Preparation of O-metal compounds with O-metal group bound to a carbon atom belonging to a six-membered aromatic ring by conversion of hydroxy groups to O-metal groups
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19961520.9 | 1999-12-20 | ||
| DE19961520A DE19961520A1 (de) | 1999-12-20 | 1999-12-20 | Verfahren zur Herstellung von Phosphoniumphenolaten |
| PCT/EP2000/012325 WO2001046100A1 (de) | 1999-12-20 | 2000-12-07 | Verfahren zur herstellung von phosphoniumphenolaten |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003518046A JP2003518046A (ja) | 2003-06-03 |
| JP2003518046A5 JP2003518046A5 (https=) | 2008-01-31 |
| JP4856340B2 true JP4856340B2 (ja) | 2012-01-18 |
Family
ID=7933456
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001546614A Expired - Fee Related JP4856340B2 (ja) | 1999-12-20 | 2000-12-07 | ホスホニウムフェノレートの製造方法 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6710153B2 (https=) |
| EP (1) | EP1242347B1 (https=) |
| JP (1) | JP4856340B2 (https=) |
| KR (1) | KR20020062354A (https=) |
| CN (1) | CN1211389C (https=) |
| AT (1) | ATE279385T1 (https=) |
| AU (1) | AU2005901A (https=) |
| BR (1) | BR0016559A (https=) |
| DE (2) | DE19961520A1 (https=) |
| ES (1) | ES2231294T3 (https=) |
| TW (1) | TWI233439B (https=) |
| WO (1) | WO2001046100A1 (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10164144A1 (de) | 2001-12-27 | 2003-07-10 | Bayer Ag | Verfahren zur Herstellung von Quartärsalzphenolatlösungen und zur Regenerierung und Rückführung von Quartärsalzphenolatlösungen aus Reaktionsgemischen |
| DE10215498A1 (de) * | 2002-04-09 | 2003-10-23 | Bayer Ag | Lagerung von Phosphoniumphenolat-Katalysatoren und deren Verwendung als Umesterungskatalysatoren |
| DE10219027A1 (de) * | 2002-04-29 | 2003-11-06 | Bayer Ag | Verfahren zur Herstellung einer flüssigen Formulierung von Phosphoniumphenolaten |
| US10413349B2 (en) * | 2011-03-04 | 2019-09-17 | Covidien Lp | System and methods for identifying tissue and vessels |
| JP6666193B2 (ja) * | 2015-04-22 | 2020-03-13 | 国立大学法人名古屋大学 | エステル交換反応用触媒及びそれを用いたエステル化合物の製造方法 |
| CN113307827A (zh) * | 2021-06-04 | 2021-08-27 | 山东师范大学实验厂 | 一种四苯基膦苯酚盐的水相合成方法 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02246140A (ja) * | 1989-03-17 | 1990-10-01 | Nitto Denko Corp | 半導体装置 |
| JPH0340459A (ja) * | 1989-07-07 | 1991-02-21 | Nitto Denko Corp | 半導体装置 |
| JPH0692899A (ja) * | 1992-09-17 | 1994-04-05 | Mitsui Toatsu Chem Inc | フェノール類の選択的パラ位カルボキシル化方法 |
| EP0826693A1 (de) * | 1996-09-03 | 1998-03-04 | Bayer Ag | Verfahren zur Herstellung von Phosponiumphenolaten |
| WO1999000395A1 (de) * | 1997-06-27 | 1999-01-07 | Bayer Aktiengesellschaft | Verfahren zur herstellung von phosphoniumphenolaten |
-
1999
- 1999-12-20 DE DE19961520A patent/DE19961520A1/de not_active Withdrawn
-
2000
- 2000-12-07 AT AT00983239T patent/ATE279385T1/de not_active IP Right Cessation
- 2000-12-07 CN CNB00817427XA patent/CN1211389C/zh not_active Expired - Fee Related
- 2000-12-07 KR KR1020027007869A patent/KR20020062354A/ko not_active Withdrawn
- 2000-12-07 AU AU20059/01A patent/AU2005901A/en not_active Abandoned
- 2000-12-07 WO PCT/EP2000/012325 patent/WO2001046100A1/de not_active Ceased
- 2000-12-07 EP EP00983239A patent/EP1242347B1/de not_active Expired - Lifetime
- 2000-12-07 US US10/168,166 patent/US6710153B2/en not_active Expired - Fee Related
- 2000-12-07 ES ES00983239T patent/ES2231294T3/es not_active Expired - Lifetime
- 2000-12-07 BR BR0016559-0A patent/BR0016559A/pt not_active Application Discontinuation
- 2000-12-07 JP JP2001546614A patent/JP4856340B2/ja not_active Expired - Fee Related
- 2000-12-07 DE DE2000508270 patent/DE50008270D1/de not_active Expired - Lifetime
- 2000-12-08 TW TW089126136A patent/TWI233439B/zh not_active IP Right Cessation
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02246140A (ja) * | 1989-03-17 | 1990-10-01 | Nitto Denko Corp | 半導体装置 |
| JPH0340459A (ja) * | 1989-07-07 | 1991-02-21 | Nitto Denko Corp | 半導体装置 |
| JPH0692899A (ja) * | 1992-09-17 | 1994-04-05 | Mitsui Toatsu Chem Inc | フェノール類の選択的パラ位カルボキシル化方法 |
| EP0826693A1 (de) * | 1996-09-03 | 1998-03-04 | Bayer Ag | Verfahren zur Herstellung von Phosponiumphenolaten |
| WO1999000395A1 (de) * | 1997-06-27 | 1999-01-07 | Bayer Aktiengesellschaft | Verfahren zur herstellung von phosphoniumphenolaten |
Also Published As
| Publication number | Publication date |
|---|---|
| ES2231294T3 (es) | 2005-05-16 |
| EP1242347A1 (de) | 2002-09-25 |
| CN1411428A (zh) | 2003-04-16 |
| EP1242347B1 (de) | 2004-10-13 |
| WO2001046100A1 (de) | 2001-06-28 |
| US6710153B2 (en) | 2004-03-23 |
| US20030013837A1 (en) | 2003-01-16 |
| CN1211389C (zh) | 2005-07-20 |
| DE50008270D1 (de) | 2004-11-18 |
| TWI233439B (en) | 2005-06-01 |
| KR20020062354A (ko) | 2002-07-25 |
| ATE279385T1 (de) | 2004-10-15 |
| BR0016559A (pt) | 2002-09-10 |
| JP2003518046A (ja) | 2003-06-03 |
| DE19961520A1 (de) | 2001-06-21 |
| AU2005901A (en) | 2001-07-03 |
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