AU2001263698A1 - Method for preparing hydroxyphenyl carboxylic acid esters - Google Patents
Method for preparing hydroxyphenyl carboxylic acid estersInfo
- Publication number
- AU2001263698A1 AU2001263698A1 AU2001263698A AU6369801A AU2001263698A1 AU 2001263698 A1 AU2001263698 A1 AU 2001263698A1 AU 2001263698 A AU2001263698 A AU 2001263698A AU 6369801 A AU6369801 A AU 6369801A AU 2001263698 A1 AU2001263698 A1 AU 2001263698A1
- Authority
- AU
- Australia
- Prior art keywords
- alkali metal
- carboxylic acid
- cmh2m
- compound
- formula
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title abstract 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 title 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 7
- -1 alkali metal salt Chemical class 0.000 abstract 7
- 150000001735 carboxylic acids Chemical class 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 150000002431 hydrogen Chemical group 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
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)
Abstract
A process for the preparation of a compound of formula (I)whereinR1 and R2 are each independently of the other C1-C8alkyl, cyclopentyl or cyclohexyl,m is 1, 2 or 3, preferably 2,n is an integer from 1 to 30, andR3 is an n-valent radical from linear or branched C4-C30alkyl, which is optionally interrupted by one or more oxygen atoms, or (when n=1-12) an n-valent radical from C5-C12cycloalkyl, or a radical R4-[NR5-CmH2m-]p,R4 is hydrogen, an n-valent radical from linear or branched C4-C30alkyl, which is optionally interrupted by one or more -NR5- groups, or (when n=1-12) an n-valent radical from C5-C12cycloalkyl,R5 radicals, each independently of any other(s), are hydrogen or methyl or -CmH2m-, preferably hydrogen, andp corresponds to the number of -[NR5-CmH2m-] groups that gives n -CmH2m- radicals per molecule,by reaction of a compound of formula (II)wherein R is C1-C3alkyl,with a compound of formula (III)wherein R3 and n have the definitions given, wherein the reaction takes place at a practically neutral acid value (pH) and in the presence of at least one alkali metal salt of an organic carboxylic acid, which salt is dissolved or suspended in the reaction mixture, or in the presence of a mixture of such alkali metal salts, (i) that alkali metal salt being formed from an alkali metal cation and an anion of an organic carboxylic acid and (ii) the organic carboxylic acid being at least partially volatile under the reaction conditions applied. Preferred alkali metal salts are alkali metal formate and alkali metal acetate.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH12512000 | 2000-06-23 | ||
| CH1251/00 | 2000-06-23 | ||
| CH3122001 | 2001-02-22 | ||
| CH0312/01 | 2001-02-22 | ||
| PCT/CH2001/000370 WO2001098249A1 (en) | 2000-06-23 | 2001-06-14 | Method for preparing hydroxyphenyl carboxylic acid esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2001263698A1 true AU2001263698A1 (en) | 2002-01-02 |
Family
ID=25735909
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2001263698A Abandoned AU2001263698A1 (en) | 2000-06-23 | 2001-06-14 | Method for preparing hydroxyphenyl carboxylic acid esters |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US6878843B2 (en) |
| EP (1) | EP1292560B1 (en) |
| JP (1) | JP4925547B2 (en) |
| KR (1) | KR100813185B1 (en) |
| CN (1) | CN1250513C (en) |
| AT (1) | ATE320412T1 (en) |
| AU (1) | AU2001263698A1 (en) |
| BR (1) | BR0111876B1 (en) |
| CA (1) | CA2412062C (en) |
| CZ (1) | CZ301602B6 (en) |
| DE (1) | DE50109215D1 (en) |
| ES (1) | ES2259325T3 (en) |
| MX (1) | MXPA02012369A (en) |
| RU (1) | RU2272022C2 (en) |
| WO (1) | WO2001098249A1 (en) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2259413T3 (en) * | 2002-04-26 | 2006-10-01 | Ciba Specialty Chemicals Holding Inc. | INCORPORABLE PHOTOINICIATOR. |
| GB0324964D0 (en) * | 2003-10-27 | 2003-11-26 | Great Lakes Chemical Europ | Preparation of hydroxyphenyl carboxylic acid esters |
| WO2008055832A2 (en) * | 2006-11-09 | 2008-05-15 | Ciba Holding Inc. | Process using liquid phenolic antioxidants |
| CN104334684B (en) | 2012-07-31 | 2019-08-27 | 株式会社艾迪科 | Latent additive and composition containing same |
| WO2015119721A1 (en) | 2014-02-07 | 2015-08-13 | C. R. Bard, Inc. | Eptfe valves |
| ES2688470T3 (en) | 2015-03-10 | 2018-11-02 | Evonik Degussa Gmbh | Antioxidants for the preparation of low emission PUR systems |
| CN105294441B (en) * | 2015-12-10 | 2017-09-15 | 中国科学院新疆理化技术研究所 | [the β of antioxidant eight（The hydroxy phenyl of 3,5 di-t-butyl 4）Propionic acid] tripentaerythritol ester synthetic method |
| CN106674002A (en) * | 2016-12-28 | 2017-05-17 | 天津利安隆新材料股份有限公司 | Preparation method of hindered phenol antioxidant |
| US20220121113A1 (en) | 2019-01-23 | 2022-04-21 | Basf Se | Oxime ester photoinitiators having a special aroyl chromophore |
| JP7703554B2 (en) | 2020-03-04 | 2025-07-07 | ベーアーエスエフ・エスエー | Oxime Ester Photoinitiators |
| CN114835991A (en) * | 2022-06-10 | 2022-08-02 | 安徽顺彤包装材料有限公司 | Water-based transfer printing film and preparation process thereof |
| EP4318166B1 (en) | 2022-08-05 | 2025-10-08 | Volocopter Technologies GmbH | Method of controlling a transition aircraft and transition aircraft |
| CN116178144A (en) * | 2023-02-10 | 2023-05-30 | 濮阳市中原石化实业有限公司 | A method for efficiently synthesizing antioxidant 245 |
| WO2025011754A1 (en) | 2023-07-10 | 2025-01-16 | Basf Se | Photocurable as well as thermally curable compositions suitable for low temperature curing |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3644482A (en) * | 1961-10-30 | 1972-02-22 | Geigy Ag J R | (4-hydroxy-5-alkylphenyl) alkanoic acid esters of polyols |
| CH454171A (en) | 1964-06-02 | 1968-04-15 | Geigy Ag J R | Process for the production of organic esters |
| CH471769A (en) * | 1965-08-02 | 1969-04-30 | Geigy Ag J R | Process for the preparation of hydroxyphenyl fatty acid esters |
| US3435065A (en) * | 1965-10-22 | 1969-03-25 | Geigy Chem Corp | N,n,n',n' - (ethylenediamine) - tetrakis (ethylene - 3 - (3',5' - di-tert-butyl-4' - hydroxyphenyl)propionate) and compositions stabilized therewith |
| SU1014213A1 (en) * | 1981-07-15 | 1991-07-30 | Научно-исследовательский институт химикатов для полимерных материалов | Method of producing pentaarythryl-tetra-[-(3,5-ditret-butyl-4-oxyphenyl)-propyonate] |
| US4536593A (en) * | 1982-07-13 | 1985-08-20 | Ciba-Geigy Corporation | Process for the preparation of sterically hindered hydroxphenylcarboxylic acid esters |
| US4594444A (en) | 1983-12-22 | 1986-06-10 | Ciba-Geigy Corporation | Process for the preparation of sterically hindered hydroxyphenylcarboxylic acid esters |
| US4716244A (en) * | 1985-05-02 | 1987-12-29 | Ciba-Geigy Corporation | Process for the preparation of sterically hindered hydroxyphenylcarboxylic acid esters |
| US5206414A (en) * | 1990-01-11 | 1993-04-27 | Ciba-Geigy Corporation | Process for the preparation of hydroxyphenylpropionic acid esters |
| US5136082A (en) | 1990-08-03 | 1992-08-04 | Himont Incorporated | Process for preparing organic esters and amides and catalyst system therefor |
| TW212790B (en) * | 1991-10-15 | 1993-09-11 | Ciba Geigy Ag | |
| EP0608089B1 (en) * | 1993-01-21 | 1997-10-15 | Sankyo Company Limited | Phenylalkanoic acid esters and their use as antioxidants |
| TW289752B (en) | 1994-03-11 | 1996-11-01 | Ciba Geigy Ag | |
| EP0808818B1 (en) * | 1996-05-23 | 2000-09-20 | Ciba SC Holding AG | Process for the preparation of substituted hydroxy-hydrocinnamate esters |
| KR20000069479A (en) | 1996-12-20 | 2000-11-25 | 시바 스폐셜티 케미칼스 홀딩 인코포레이티드 | Transesterification Catalysts Fixed To Solid Support Materials |
-
2001
- 2001-06-14 CZ CZ20030108A patent/CZ301602B6/en not_active IP Right Cessation
- 2001-06-14 BR BRPI0111876-5A patent/BR0111876B1/en not_active IP Right Cessation
- 2001-06-14 JP JP2002504205A patent/JP4925547B2/en not_active Expired - Fee Related
- 2001-06-14 US US10/311,724 patent/US6878843B2/en not_active Expired - Lifetime
- 2001-06-14 CN CNB018115365A patent/CN1250513C/en not_active Expired - Fee Related
- 2001-06-14 EP EP01937911A patent/EP1292560B1/en not_active Expired - Lifetime
- 2001-06-14 AT AT01937911T patent/ATE320412T1/en not_active IP Right Cessation
- 2001-06-14 AU AU2001263698A patent/AU2001263698A1/en not_active Abandoned
- 2001-06-14 RU RU2003100511/04A patent/RU2272022C2/en not_active IP Right Cessation
- 2001-06-14 CA CA2412062A patent/CA2412062C/en not_active Expired - Fee Related
- 2001-06-14 DE DE50109215T patent/DE50109215D1/en not_active Expired - Lifetime
- 2001-06-14 ES ES01937911T patent/ES2259325T3/en not_active Expired - Lifetime
- 2001-06-14 KR KR1020027016517A patent/KR100813185B1/en not_active Expired - Fee Related
- 2001-06-14 WO PCT/CH2001/000370 patent/WO2001098249A1/en not_active Ceased
- 2001-06-14 MX MXPA02012369A patent/MXPA02012369A/en active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| CN1250513C (en) | 2006-04-12 |
| ES2259325T3 (en) | 2006-10-01 |
| KR20030007861A (en) | 2003-01-23 |
| CZ301602B6 (en) | 2010-04-28 |
| BR0111876A (en) | 2003-06-24 |
| CA2412062A1 (en) | 2001-12-27 |
| RU2272022C2 (en) | 2006-03-20 |
| US6878843B2 (en) | 2005-04-12 |
| EP1292560A1 (en) | 2003-03-19 |
| EP1292560B1 (en) | 2006-03-15 |
| JP2004501128A (en) | 2004-01-15 |
| BR0111876B1 (en) | 2012-09-18 |
| DE50109215D1 (en) | 2006-05-11 |
| CA2412062C (en) | 2011-09-20 |
| US20030166962A1 (en) | 2003-09-04 |
| WO2001098249A1 (en) | 2001-12-27 |
| CZ2003108A3 (en) | 2003-05-14 |
| MXPA02012369A (en) | 2003-04-25 |
| JP4925547B2 (en) | 2012-04-25 |
| KR100813185B1 (en) | 2008-03-17 |
| ATE320412T1 (en) | 2006-04-15 |
| CN1437572A (en) | 2003-08-20 |
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