TWI233439B - Process for the production of phosphonium phenolates - Google Patents
Process for the production of phosphonium phenolates Download PDFInfo
- Publication number
- TWI233439B TWI233439B TW089126136A TW89126136A TWI233439B TW I233439 B TWI233439 B TW I233439B TW 089126136 A TW089126136 A TW 089126136A TW 89126136 A TW89126136 A TW 89126136A TW I233439 B TWI233439 B TW I233439B
- Authority
- TW
- Taiwan
- Prior art keywords
- scope
- patent application
- item
- reaction
- phenol
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 27
- 238000004519 manufacturing process Methods 0.000 title abstract description 12
- LVLZXBIWQHFREA-UHFFFAOYSA-N phenol;phosphane Chemical class [PH4+].[O-]C1=CC=CC=C1 LVLZXBIWQHFREA-UHFFFAOYSA-N 0.000 title abstract 4
- 238000002425 crystallisation Methods 0.000 claims abstract description 7
- 230000008025 crystallization Effects 0.000 claims abstract description 7
- 239000000203 mixture Substances 0.000 claims abstract description 7
- 150000002989 phenols Chemical class 0.000 claims abstract description 7
- 239000012670 alkaline solution Substances 0.000 claims abstract description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 229920000515 polycarbonate Polymers 0.000 claims description 13
- 239000004417 polycarbonate Substances 0.000 claims description 13
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 12
- 239000000243 solution Substances 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 239000012044 organic layer Substances 0.000 claims description 10
- 238000005809 transesterification reaction Methods 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 6
- 230000002079 cooperative effect Effects 0.000 claims description 4
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 238000004064 recycling Methods 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- -1 phosphonium halides Chemical class 0.000 abstract description 13
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 150000001298 alcohols Chemical class 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000011049 filling Methods 0.000 description 9
- 239000008367 deionised water Substances 0.000 description 8
- 239000010410 layer Substances 0.000 description 8
- 229910021641 deionized water Inorganic materials 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 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 5
- 238000003756 stirring Methods 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 229930185605 Bisphenol Natural products 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000006085 branching agent Substances 0.000 description 3
- 239000013078 crystal Substances 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
- 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- QCRFMSUKWRQZEM-UHFFFAOYSA-N cycloheptanol Chemical compound OC1CCCCCC1 QCRFMSUKWRQZEM-UHFFFAOYSA-N 0.000 description 2
- FHADSMKORVFYOS-UHFFFAOYSA-N cyclooctanol Chemical compound OC1CCCCCCC1 FHADSMKORVFYOS-UHFFFAOYSA-N 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 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
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002904 solvent Substances 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
- 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
- QJQZRLXDLORINA-UHFFFAOYSA-N 2-cyclohexylethanol Chemical compound OCCC1CCCCC1 QJQZRLXDLORINA-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 238000003547 Friedel-Crafts alkylation reaction Methods 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 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
- 238000001816 cooling Methods 0.000 description 1
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
- SZMNDOUFZGODBR-UHFFFAOYSA-N decan-5-ol Chemical compound CCCCCC(O)CCCC SZMNDOUFZGODBR-UHFFFAOYSA-N 0.000 description 1
- 238000005034 decoration Methods 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
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004870 electrical engineering Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19961520A DE19961520A1 (de) | 1999-12-20 | 1999-12-20 | Verfahren zur Herstellung von Phosphoniumphenolaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TWI233439B true TWI233439B (en) | 2005-06-01 |
Family
ID=7933456
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW089126136A TWI233439B (en) | 1999-12-20 | 2000-12-08 | Process for the production of phosphonium phenolates |
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 |
Family Cites Families (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 |
| JP3117296B2 (ja) * | 1992-09-17 | 2000-12-11 | 三井化学株式会社 | 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 |
| DE19727351C1 (de) * | 1997-06-27 | 1999-02-11 | Bayer Ag | 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
Also Published As
| Publication number | Publication date |
|---|---|
| ES2231294T3 (es) | 2005-05-16 |
| EP1242347A1 (de) | 2002-09-25 |
| CN1411428A (zh) | 2003-04-16 |
| JP4856340B2 (ja) | 2012-01-18 |
| 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 |
| 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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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Annulment or lapse of patent due to non-payment of fees |