TW212790B - - Google Patents
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- TW212790B TW212790B TW081107843A TW81107843A TW212790B TW 212790 B TW212790 B TW 212790B TW 081107843 A TW081107843 A TW 081107843A TW 81107843 A TW81107843 A TW 81107843A TW 212790 B TW212790 B TW 212790B
- Authority
- TW
- Taiwan
- Prior art keywords
- item
- formula
- reaction
- ministry
- compound
- Prior art date
Links
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 19
- 239000003054 catalyst Substances 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- -1 n-octadecyl Chemical group 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical group [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 2
- 239000000052 vinegar Substances 0.000 claims description 2
- 235000021419 vinegar Nutrition 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 4
- 235000019253 formic acid Nutrition 0.000 description 4
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 4
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 description 3
- 240000007839 Kleinhovia hospita Species 0.000 description 3
- 230000002882 anti-plaque Effects 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000002079 cooperative effect Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000005809 transesterification reaction Methods 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- HDYRYUINDGQKMC-UHFFFAOYSA-M acetyloxyaluminum;dihydrate Chemical compound O.O.CC(=O)O[Al] HDYRYUINDGQKMC-UHFFFAOYSA-M 0.000 description 2
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 2
- 229940009827 aluminum acetate Drugs 0.000 description 2
- 229940058905 antimony compound for treatment of leishmaniasis and trypanosomiasis Drugs 0.000 description 2
- 150000001463 antimony compounds Chemical class 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000002309 gasification Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- OPSWAWSNPREEFQ-UHFFFAOYSA-K triphenoxyalumane Chemical compound [Al+3].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 OPSWAWSNPREEFQ-UHFFFAOYSA-K 0.000 description 2
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 125000006219 1-ethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- PIWWRPFGQRIWSD-UHFFFAOYSA-N 2,6-ditert-butyl-4-methylphenol;propanoic acid Chemical compound CCC(O)=O.CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 PIWWRPFGQRIWSD-UHFFFAOYSA-N 0.000 description 1
- CQOZJDNCADWEKH-UHFFFAOYSA-N 2-[3,3-bis(2-hydroxyphenyl)propyl]phenol Chemical compound OC1=CC=CC=C1CCC(C=1C(=CC=CC=1)O)C1=CC=CC=C1O CQOZJDNCADWEKH-UHFFFAOYSA-N 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- WRGWAEBYMBFFCR-UHFFFAOYSA-N 4-butyl-2-methylphenol Chemical compound CCCCC1=CC=C(O)C(C)=C1 WRGWAEBYMBFFCR-UHFFFAOYSA-N 0.000 description 1
- 229910000838 Al alloy Inorganic materials 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 241000288726 Soricidae Species 0.000 description 1
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 150000004645 aluminates Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical group CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 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
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- HSKKYAVRBWNUQB-UHFFFAOYSA-N ethene;propane-1,2,3-triol Chemical compound C=C.C=C.C=C.OCC(O)CO HSKKYAVRBWNUQB-UHFFFAOYSA-N 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
- C07C39/08—Dihydroxy benzenes; Alkylated derivatives thereof
-
- 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)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH302891 | 1991-10-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW212790B true TW212790B (en, 2012) | 1993-09-11 |
Family
ID=4247022
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW081107843A TW212790B (en, 2012) | 1991-10-15 | 1992-10-02 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US5481023A (en, 2012) |
| EP (1) | EP0538189B1 (en, 2012) |
| JP (1) | JP3341216B2 (en, 2012) |
| KR (1) | KR100289102B1 (en, 2012) |
| CN (1) | CN1039993C (en, 2012) |
| BR (1) | BR9203974A (en, 2012) |
| CA (1) | CA2080429C (en, 2012) |
| CZ (1) | CZ279447B6 (en, 2012) |
| DE (1) | DE59205000D1 (en, 2012) |
| ES (1) | ES2082433T3 (en, 2012) |
| MX (1) | MX9205907A (en, 2012) |
| SK (1) | SK279239B6 (en, 2012) |
| TW (1) | TW212790B (en, 2012) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0675940B1 (en) * | 1993-10-28 | 2000-05-24 | Chevron Chemical Company LLC | Polyalkyl hydroxyaromatic esters and fuel compositions containing the same |
| TW289752B (en, 2012) * | 1994-03-11 | 1996-11-01 | Ciba Geigy Ag | |
| EP0933352B1 (en) * | 1998-02-02 | 2003-03-12 | Ciba SC Holding AG | Improved process for the preparation of substituted hydroxyhydrocinnamate esters by removal of tin catalysts |
| US6232481B1 (en) | 2000-01-11 | 2001-05-15 | Regents Of The University Of Minnesota | Method for manufacturing betulinic acid |
| ES2259325T3 (es) | 2000-06-23 | 2006-10-01 | Ciba Specialty Chemicals Holding Inc. | Procedimiento para la obtencion de esteres de acidos hidroxifenilcarboxilicos. |
| US7667066B2 (en) | 2004-02-27 | 2010-02-23 | Albemarle Corporation | Preparation of sterically hindered hydroxyphenylcarboxylic acid esters |
| US20060183935A1 (en) * | 2005-02-15 | 2006-08-17 | The Lubrizol Corporation | Processing improvements for hindered, ester-substituted phenols |
| CN102030647B (zh) * | 2010-11-05 | 2013-06-19 | 山东省临沂市三丰化工有限公司 | 一种制备液体抗氧剂的清洁生产方法 |
| PT3067343T (pt) | 2015-03-10 | 2018-10-22 | Evonik Degussa Gmbh | Antioxidantes para a produção de sistemas de poliuretano com baixas emissões de carbono |
| JP6503220B2 (ja) * | 2015-04-30 | 2019-04-17 | 上野製薬株式会社 | ４−ヒドロキシ安息香酸長鎖エステルの精製方法 |
| JP6503227B2 (ja) * | 2015-05-27 | 2019-04-17 | 上野製薬株式会社 | ４−ヒドロキシ安息香酸長鎖エステルの精製方法 |
| WO2024170610A1 (en) | 2023-02-17 | 2024-08-22 | Basf Se | Process for the preparation of hydroxyphenylcarboxylic acid esters using catalytic transesterification |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL284832A (en, 2012) * | 1961-10-30 | |||
| GB1094532A (en) | 1965-05-03 | 1967-12-13 | Ici Ltd | Phenolic ester stabilisers and polyolefine compositions containing them |
| FR1490341A (fr) * | 1965-08-27 | 1967-07-28 | Universal Oil Prod Co | Nouveau parfum et son procédé de préparation |
| CH549407A (de) * | 1970-07-06 | 1974-05-31 | Ciba Geigy Ag | Verwendung sterisch gehinderter phenolestern von glykolen als stabilisatoren. |
| US4228297A (en) * | 1972-12-27 | 1980-10-14 | Ciba-Geigy Corporation | Process for the production of hydroxyalkylphenyl derivatives |
| US4112240A (en) * | 1973-09-15 | 1978-09-05 | Dynamit Nobel Aktiengesellschaft | Process for the manufacture of light colored dipropyleneglycol dibenzoate |
| US4085132A (en) * | 1975-06-24 | 1978-04-18 | Ciba-Geigy Corporation | Process for the production of hydroxyalkylphenyl derivatives |
| US4536593A (en) * | 1982-07-13 | 1985-08-20 | Ciba-Geigy Corporation | Process for the preparation of sterically hindered hydroxphenylcarboxylic acid esters |
| US4618700A (en) * | 1983-12-22 | 1986-10-21 | Ciba-Geigy Corporation | Process for the preparation of a hydroxyphenylcarboxylate |
| 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 |
-
1992
- 1992-10-02 TW TW081107843A patent/TW212790B/zh not_active IP Right Cessation
- 1992-10-06 ES ES92810758T patent/ES2082433T3/es not_active Expired - Lifetime
- 1992-10-06 DE DE59205000T patent/DE59205000D1/de not_active Expired - Lifetime
- 1992-10-06 EP EP92810758A patent/EP0538189B1/de not_active Expired - Lifetime
- 1992-10-12 CZ CS923106A patent/CZ279447B6/cs not_active IP Right Cessation
- 1992-10-12 SK SK3106-92A patent/SK279239B6/sk not_active IP Right Cessation
- 1992-10-13 CA CA002080429A patent/CA2080429C/en not_active Expired - Fee Related
- 1992-10-14 KR KR1019920019007A patent/KR100289102B1/ko not_active Expired - Lifetime
- 1992-10-14 BR BR929203974A patent/BR9203974A/pt not_active IP Right Cessation
- 1992-10-15 MX MX9205907A patent/MX9205907A/es not_active IP Right Cessation
- 1992-10-15 CN CN92111500A patent/CN1039993C/zh not_active Expired - Lifetime
- 1992-10-15 JP JP30304892A patent/JP3341216B2/ja not_active Expired - Fee Related
-
1993
- 1993-09-30 US US08/129,789 patent/US5481023A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH05310640A (ja) | 1993-11-22 |
| SK310692A3 (en) | 1995-02-08 |
| SK279239B6 (sk) | 1998-08-05 |
| BR9203974A (pt) | 1993-04-27 |
| CN1071414A (zh) | 1993-04-28 |
| DE59205000D1 (de) | 1996-02-22 |
| MX9205907A (es) | 1993-04-01 |
| KR100289102B1 (ko) | 2001-05-02 |
| JP3341216B2 (ja) | 2002-11-05 |
| KR930007879A (ko) | 1993-05-20 |
| CA2080429A1 (en) | 1993-04-16 |
| EP0538189A3 (de) | 1993-04-28 |
| CN1039993C (zh) | 1998-09-30 |
| CZ279447B6 (cs) | 1995-04-12 |
| US5481023A (en) | 1996-01-02 |
| CA2080429C (en) | 2004-01-06 |
| CZ310692A3 (en) | 1993-05-12 |
| EP0538189A2 (de) | 1993-04-21 |
| ES2082433T3 (es) | 1996-03-16 |
| EP0538189B1 (de) | 1996-01-10 |
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| MK4A | Expiration of patent term of an invention patent |