DE60114521T2 - Verfahren zur Herstellung von Carbonsäurearylestern - Google Patents
Verfahren zur Herstellung von Carbonsäurearylestern Download PDFInfo
- Publication number
- DE60114521T2 DE60114521T2 DE60114521T DE60114521T DE60114521T2 DE 60114521 T2 DE60114521 T2 DE 60114521T2 DE 60114521 T DE60114521 T DE 60114521T DE 60114521 T DE60114521 T DE 60114521T DE 60114521 T2 DE60114521 T2 DE 60114521T2
- Authority
- DE
- Germany
- Prior art keywords
- carboxylic acid
- reaction
- preparation
- aryl esters
- acid aryl
- 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 - Lifetime
Links
- -1 carboxylic acid aryl esters Chemical class 0.000 title claims description 32
- 238000000034 method Methods 0.000 title claims description 21
- 238000002360 preparation method Methods 0.000 title description 9
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 150000007514 bases Chemical class 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 150000004706 metal oxides Chemical class 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 28
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 14
- 238000010992 reflux Methods 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- 230000032050 esterification Effects 0.000 description 9
- 238000005886 esterification reaction Methods 0.000 description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 8
- 238000004811 liquid chromatography Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 4
- 239000012024 dehydrating agents Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000005711 Benzoic acid Substances 0.000 description 3
- 150000001447 alkali salts Chemical class 0.000 description 3
- 235000010233 benzoic acid Nutrition 0.000 description 3
- 238000010276 construction Methods 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- KFJDQPJLANOOOB-UHFFFAOYSA-N 2h-benzotriazole-4-carboxylic acid Chemical compound OC(=O)C1=CC=CC2=NNN=C12 KFJDQPJLANOOOB-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- ODVYFOLTLWONHF-UHFFFAOYSA-N diphenyl decanedioate Chemical compound C=1C=CC=CC=1OC(=O)CCCCCCCCC(=O)OC1=CC=CC=C1 ODVYFOLTLWONHF-UHFFFAOYSA-N 0.000 description 2
- KUMNEOGIHFCNQW-UHFFFAOYSA-N diphenyl phosphite Chemical compound C=1C=CC=CC=1OP([O-])OC1=CC=CC=C1 KUMNEOGIHFCNQW-UHFFFAOYSA-N 0.000 description 2
- 230000008034 disappearance Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229920000137 polyphosphoric acid Polymers 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- 150000007860 aryl ester derivatives Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001734 carboxylic acid salts Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- FCJSHPDYVMKCHI-UHFFFAOYSA-N phenyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1=CC=CC=C1 FCJSHPDYVMKCHI-UHFFFAOYSA-N 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- MWASJOFAOJVIGL-UHFFFAOYSA-M sodium;2h-benzotriazole-4-carboxylate Chemical compound [Na+].[O-]C(=O)C1=CC=CC2=C1N=NN2 MWASJOFAOJVIGL-UHFFFAOYSA-M 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D249/18—Benzotriazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/10—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond
- C07C67/11—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond being mineral ester groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000219514 | 2000-07-19 | ||
| JP2000219514A JP4592158B2 (ja) | 2000-07-19 | 2000-07-19 | カルボン酸アリールエステルの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60114521D1 DE60114521D1 (de) | 2005-12-08 |
| DE60114521T2 true DE60114521T2 (de) | 2006-08-10 |
Family
ID=18714290
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60114521T Expired - Lifetime DE60114521T2 (de) | 2000-07-19 | 2001-07-17 | Verfahren zur Herstellung von Carbonsäurearylestern |
| DE60140384T Expired - Lifetime DE60140384D1 (de) | 2000-07-19 | 2001-07-17 | Verfahren zur Herstellung von Carbonsäurearylestern |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60140384T Expired - Lifetime DE60140384D1 (de) | 2000-07-19 | 2001-07-17 | Verfahren zur Herstellung von Carbonsäurearylestern |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US6495712B2 (enExample) |
| EP (3) | EP1174413B1 (enExample) |
| JP (1) | JP4592158B2 (enExample) |
| DE (2) | DE60114521T2 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4635315B2 (ja) * | 1999-09-29 | 2011-02-23 | 東ソー株式会社 | フェニルエステルの製造方法及び触媒 |
| KR100525358B1 (ko) * | 2003-08-21 | 2005-11-04 | 주식회사 이엔에프테크놀로지 | 카르복실 벤조트리아졸 알킬에스테르의 제조방법 |
| US20070219342A1 (en) * | 2006-03-16 | 2007-09-20 | The P. D. George Company | Catalysis of polyimide curing |
| JP5286718B2 (ja) * | 2007-08-01 | 2013-09-11 | 宇部興産株式会社 | フェニルエステル及びリチウム二次電池用非水電解液並びにそれを用いたリチウム二次電池 |
| AU2010234820B2 (en) * | 2009-03-31 | 2012-09-27 | Cytec Technology Corp. | Water based non-chromated primers for structural bonding applications |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5822021B2 (ja) * | 1976-08-27 | 1983-05-06 | 大栄化工株式会社 | アリ−ルオキシカルボン酸アリ−ルエステル類の製造法 |
| JPS6445341A (en) * | 1987-08-14 | 1989-02-17 | Nippon Catalytic Chem Ind | Production of 1,4-dihydroxy-2-naphthoic acid aryl ester |
| US5162570A (en) * | 1989-06-27 | 1992-11-10 | Sumitomo Chemical Company, Limited | Process for producing 1,4-dihydroxy-2-arylnaphthoate |
| JP2759088B2 (ja) * | 1989-07-19 | 1998-05-28 | 住化ファインケム株式会社 | １，４―ジヒドロキシ―２―ナフトエ酸アリールエステルの製造法 |
| JPH03204839A (ja) * | 1989-06-27 | 1991-09-06 | Daiei Kako Kk | １，４―ジヒドロキシ―２―ナフトエ酸アリールエステルの製造方法 |
| US5808130A (en) * | 1996-06-27 | 1998-09-15 | Henkel Corporation | Esterification of phenols |
| JP3962467B2 (ja) * | 1997-12-06 | 2007-08-22 | 住友化学株式会社 | １，４−ジヒドロキシ−２−ナフトエ酸アリールエステル類の製造方法 |
| JPH11269156A (ja) * | 1998-03-19 | 1999-10-05 | Sumika Fine Chemicals Co Ltd | ５−フェノキシカルボニルベンゾトリアゾールの製造方法 |
-
2000
- 2000-07-19 JP JP2000219514A patent/JP4592158B2/ja not_active Expired - Fee Related
-
2001
- 2001-07-17 EP EP01117294A patent/EP1174413B1/en not_active Expired - Lifetime
- 2001-07-17 DE DE60114521T patent/DE60114521T2/de not_active Expired - Lifetime
- 2001-07-17 EP EP04027910A patent/EP1524257B1/en not_active Expired - Lifetime
- 2001-07-17 DE DE60140384T patent/DE60140384D1/de not_active Expired - Lifetime
- 2001-07-17 EP EP04027911A patent/EP1524258A1/en not_active Withdrawn
- 2001-07-18 US US09/906,748 patent/US6495712B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP1524257A1 (en) | 2005-04-20 |
| EP1524257B1 (en) | 2009-11-04 |
| US20020013491A1 (en) | 2002-01-31 |
| DE60114521D1 (de) | 2005-12-08 |
| US6495712B2 (en) | 2002-12-17 |
| EP1524258A1 (en) | 2005-04-20 |
| DE60140384D1 (de) | 2009-12-17 |
| JP4592158B2 (ja) | 2010-12-01 |
| EP1174413B1 (en) | 2005-11-02 |
| JP2002030005A (ja) | 2002-01-29 |
| EP1174413A2 (en) | 2002-01-23 |
| EP1174413A3 (en) | 2002-07-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition |