NO300321B1 - Fremgangsmåte for fremstilling av karboksylsyrer eller estere av disse ved oksidativ spaltning av umettede fettsyrer eller fettsyreestere - Google Patents
Fremgangsmåte for fremstilling av karboksylsyrer eller estere av disse ved oksidativ spaltning av umettede fettsyrer eller fettsyreestere Download PDFInfo
- Publication number
- NO300321B1 NO300321B1 NO942175A NO942175A NO300321B1 NO 300321 B1 NO300321 B1 NO 300321B1 NO 942175 A NO942175 A NO 942175A NO 942175 A NO942175 A NO 942175A NO 300321 B1 NO300321 B1 NO 300321B1
- Authority
- NO
- Norway
- Prior art keywords
- acid
- esters
- fatty acid
- chloride
- acids
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 26
- 150000002148 esters Chemical class 0.000 title claims abstract description 13
- 235000021122 unsaturated fatty acids Nutrition 0.000 title claims abstract description 10
- 150000004670 unsaturated fatty acids Chemical group 0.000 title claims abstract description 10
- 150000001735 carboxylic acids Chemical class 0.000 title claims abstract description 5
- 235000014113 dietary fatty acids Nutrition 0.000 title claims description 15
- 229930195729 fatty acid Natural products 0.000 title claims description 15
- 239000000194 fatty acid Substances 0.000 title claims description 15
- -1 fatty acid esters Chemical class 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title description 2
- 238000006864 oxidative decomposition reaction Methods 0.000 title 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 32
- 239000003054 catalyst Substances 0.000 claims abstract description 20
- 238000007248 oxidative elimination reaction Methods 0.000 claims abstract description 19
- 238000012546 transfer Methods 0.000 claims abstract description 13
- 239000012071 phase Substances 0.000 claims abstract description 12
- 239000002253 acid Substances 0.000 claims abstract description 11
- 239000008346 aqueous phase Substances 0.000 claims abstract description 11
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 11
- 239000012074 organic phase Substances 0.000 claims abstract description 10
- 230000003197 catalytic effect Effects 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 5
- 150000001449 anionic compounds Chemical class 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
- 150000002430 hydrocarbons Chemical group 0.000 claims abstract description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 4
- 229910001412 inorganic anion Inorganic materials 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 15
- 150000004665 fatty acids Chemical class 0.000 claims description 7
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 6
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 6
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 6
- 239000005642 Oleic acid Substances 0.000 claims description 6
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 6
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 6
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 4
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 claims description 4
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 claims description 4
- ZCPCLAPUXMZUCD-UHFFFAOYSA-M dihexadecyl(dimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCC ZCPCLAPUXMZUCD-UHFFFAOYSA-M 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 claims description 3
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 claims description 2
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 claims description 2
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 claims description 2
- 235000021319 Palmitoleic acid Nutrition 0.000 claims description 2
- VBIIFPGSPJYLRR-UHFFFAOYSA-M Stearyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C VBIIFPGSPJYLRR-UHFFFAOYSA-M 0.000 claims description 2
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 claims description 2
- 235000020661 alpha-linolenic acid Nutrition 0.000 claims description 2
- 229940114079 arachidonic acid Drugs 0.000 claims description 2
- 235000021342 arachidonic acid Nutrition 0.000 claims description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 2
- WOWHHFRSBJGXCM-UHFFFAOYSA-M cetyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)C WOWHHFRSBJGXCM-UHFFFAOYSA-M 0.000 claims description 2
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 claims description 2
- KHAVLLBUVKBTBG-UHFFFAOYSA-N dec-9-enoic acid Chemical compound OC(=O)CCCCCCCC=C KHAVLLBUVKBTBG-UHFFFAOYSA-N 0.000 claims description 2
- REZZEXDLIUJMMS-UHFFFAOYSA-M dimethyldioctadecylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC REZZEXDLIUJMMS-UHFFFAOYSA-M 0.000 claims description 2
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 claims description 2
- 229960004488 linolenic acid Drugs 0.000 claims description 2
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 claims description 2
- 229960002969 oleic acid Drugs 0.000 claims description 2
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 claims description 2
- 229960003656 ricinoleic acid Drugs 0.000 claims description 2
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000005846 sugar alcohols Polymers 0.000 claims description 2
- NNENFOSYDBTCBO-UHFFFAOYSA-M tributyl(hexadecyl)phosphanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC NNENFOSYDBTCBO-UHFFFAOYSA-M 0.000 claims description 2
- 150000002751 molybdenum Chemical class 0.000 claims 1
- 229910052727 yttrium Inorganic materials 0.000 claims 1
- 150000007513 acids Chemical class 0.000 abstract description 4
- 159000000011 group IA salts Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 9
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- DRUKNYVQGHETPO-UHFFFAOYSA-N dimethyl azelate Chemical compound COC(=O)CCCCCCCC(=O)OC DRUKNYVQGHETPO-UHFFFAOYSA-N 0.000 description 6
- IJXHLVMUNBOGRR-UHFFFAOYSA-N methyl nonanoate Chemical compound CCCCCCCCC(=O)OC IJXHLVMUNBOGRR-UHFFFAOYSA-N 0.000 description 6
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 238000004508 fractional distillation Methods 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 235000020778 linoleic acid Nutrition 0.000 description 4
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000005643 Pelargonic acid Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical compound O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 description 3
- 239000004593 Epoxy Chemical class 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229910052785 arsenic Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000002009 diols Chemical group 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229910052721 tungsten Inorganic materials 0.000 description 2
- WTTJVINHCBCLGX-UHFFFAOYSA-N (9trans,12cis)-methyl linoleate Natural products CCCCCC=CCC=CCCCCCCCC(=O)OC WTTJVINHCBCLGX-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000007792 gaseous phase Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- WTTJVINHCBCLGX-NQLNTKRDSA-N methyl linoleate Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)OC WTTJVINHCBCLGX-NQLNTKRDSA-N 0.000 description 1
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 1
- 229940073769 methyl oleate Drugs 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- VLAPMBHFAWRUQP-UHFFFAOYSA-L molybdic acid Chemical compound O[Mo](O)(=O)=O VLAPMBHFAWRUQP-UHFFFAOYSA-L 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 229910000487 osmium oxide Inorganic materials 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 1
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/285—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with peroxy-compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITTO910963A IT1251708B (it) | 1991-12-11 | 1991-12-11 | Procedimento per la preparazione di acidi carbossilici o loro esteri mediante scissione ossidativa di acidi grassi insaturi o loro esteri. |
| PCT/EP1992/002822 WO1993012064A1 (en) | 1991-12-11 | 1992-12-07 | A method of preparing carboxylic acids or esters thereof by the oxidative cleavage of unsaturated fatty acids or esters thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO942175L NO942175L (da) | 1994-06-10 |
| NO942175D0 NO942175D0 (no) | 1994-06-10 |
| NO300321B1 true NO300321B1 (no) | 1997-05-12 |
Family
ID=11409772
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO942175A NO300321B1 (no) | 1991-12-11 | 1994-06-10 | Fremgangsmåte for fremstilling av karboksylsyrer eller estere av disse ved oksidativ spaltning av umettede fettsyrer eller fettsyreestere |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US5336793A (da) |
| EP (1) | EP0621861B1 (da) |
| JP (1) | JPH07502035A (da) |
| CN (1) | CN1075711A (da) |
| AT (1) | ATE148686T1 (da) |
| AU (1) | AU658957B2 (da) |
| BR (1) | BR9207023A (da) |
| CA (1) | CA2125474A1 (da) |
| DE (1) | DE69217388T2 (da) |
| DK (1) | DK0621861T3 (da) |
| ES (1) | ES2097370T3 (da) |
| FI (1) | FI106796B (da) |
| GR (1) | GR3022792T3 (da) |
| IL (1) | IL103957A0 (da) |
| IT (1) | IT1251708B (da) |
| NO (1) | NO300321B1 (da) |
| WO (1) | WO1993012064A1 (da) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1256989B (it) * | 1992-10-29 | 1995-12-27 | Novamont Spa | Procedimento per la preparazione di acidi carbossilici o loro esteri mediante scissione ossidativa di acidi grassi insaturi o loro esteri. |
| GB9313080D0 (en) * | 1993-06-25 | 1993-08-11 | Solvay Interox Ltd | Oxidative cleavage of alkenes |
| US5596111A (en) * | 1995-06-05 | 1997-01-21 | North Dakota State University | Method for preparation of carboxylic acids |
| US6051725A (en) * | 1998-12-28 | 2000-04-18 | Caschem, Inc. | Epoxidation of ricinic compounds using a phase-transfer catalyst |
| US6414168B1 (en) | 1998-12-28 | 2002-07-02 | Caschem, Inc. | Epoxidation of ricinic compounds using a phase-transfer catalyst |
| DE19922643A1 (de) | 1999-05-18 | 2000-11-23 | Bayer Ag | Herstellung von aliphatischen alpha,omega-Dicarbonsäuren |
| CN1087012C (zh) * | 1999-09-29 | 2002-07-03 | 中国科学院兰州化学物理研究所 | 清洁催化氧化合成己二酸的方法 |
| US8043273B2 (en) * | 2002-12-19 | 2011-10-25 | Kimberly-Clark Worldwide, Inc. | Disposable undergarment with a stretchable absorbent insert and method for the use thereof |
| CN100415707C (zh) * | 2004-09-17 | 2008-09-03 | 中国科学院新疆理化技术研究所 | 一种用微波反应制备壬二酸的方法 |
| ITMI20070953A1 (it) * | 2007-05-10 | 2008-11-11 | Novamont Spa | Processo di scissione catalitica di oli vegetali |
| US8513287B2 (en) | 2007-12-27 | 2013-08-20 | Eisai R&D Management Co., Ltd. | Heterocyclic ring and phosphonoxymethyl group substituted pyridine derivatives and antifungal agent containing same |
| MY169801A (en) * | 2008-12-31 | 2019-05-16 | Battelle Memorial Institute | Preparation of esters and polyols by initial oxidative cleavage of fatty acids followed by esterification reactions |
| JP5448036B2 (ja) * | 2009-02-18 | 2014-03-19 | トヨタ自動車株式会社 | カルボン酸の製造方法 |
| CN101811954B (zh) * | 2010-04-23 | 2012-12-26 | 浙江华诺化工有限公司 | 油酸催化氧化制备壬二酸的方法 |
| FR2970252B1 (fr) | 2011-01-10 | 2013-11-15 | Arkema France | Procede de production de composes nitrile-acide gras |
| FI123683B (en) * | 2011-11-28 | 2013-09-13 | Teknologian Tutkimuskeskus Vtt | Process for catalytic oxidation of a natural composition comprising unsaturated fatty acids and / or esters thereof and use of a mixture obtained therefrom to produce mono-, oligo- and / or polyesters |
| FR2984887B1 (fr) * | 2011-12-22 | 2014-01-03 | Toulouse Inst Nat Polytech | Procede de scission moleculaire oxydative d'un compose gras |
| CN110117223A (zh) * | 2018-02-05 | 2019-08-13 | 北京先锋创新科技发展有限公司 | 一种臭氧氧化法制备并分离提纯壬二酸的方法 |
| CN109467684B (zh) * | 2018-12-17 | 2020-11-24 | 南开大学 | 一种氧化蓖麻油酸聚合酯制备方法 |
| FR3100809B1 (fr) | 2019-09-16 | 2023-06-02 | Demeta | Procédé de coupure oxydante d'oléfines utilisant comme catalyseur un halooxodiperoxométallate |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3855257A (en) * | 1970-06-29 | 1974-12-17 | Procter & Gamble | Preparation of carboxylic acids by the oxidation of vicinal glycols |
| GB1324763A (en) * | 1971-03-19 | 1973-07-25 | Continental Oil Co | Phase transfer catalysis of heterogeneous reactions by quaternary salts |
| IT1200002B (it) * | 1983-04-15 | 1989-01-05 | Montedison Spa | Procedimento per la preparazione di acidi carbossilici a partire da olefine o diidrossicomposti vicinali |
| JPH0761972B2 (ja) * | 1986-10-08 | 1995-07-05 | 新日本理化株式会社 | カルボン酸の製造法 |
-
1991
- 1991-12-11 IT ITTO910963A patent/IT1251708B/it active IP Right Grant
-
1992
- 1992-12-03 IL IL92103957A patent/IL103957A0/xx unknown
- 1992-12-07 BR BR9207023A patent/BR9207023A/pt not_active IP Right Cessation
- 1992-12-07 CA CA002125474A patent/CA2125474A1/en not_active Abandoned
- 1992-12-07 DK DK92924679.1T patent/DK0621861T3/da active
- 1992-12-07 EP EP92924679A patent/EP0621861B1/en not_active Expired - Lifetime
- 1992-12-07 AU AU30856/92A patent/AU658957B2/en not_active Ceased
- 1992-12-07 DE DE69217388T patent/DE69217388T2/de not_active Expired - Fee Related
- 1992-12-07 WO PCT/EP1992/002822 patent/WO1993012064A1/en active IP Right Grant
- 1992-12-07 ES ES92924679T patent/ES2097370T3/es not_active Expired - Lifetime
- 1992-12-07 AT AT92924679T patent/ATE148686T1/de not_active IP Right Cessation
- 1992-12-07 JP JP5510583A patent/JPH07502035A/ja active Pending
- 1992-12-10 US US07/988,671 patent/US5336793A/en not_active Expired - Lifetime
- 1992-12-10 CN CN92115181A patent/CN1075711A/zh active Pending
-
1994
- 1994-06-08 FI FI942694A patent/FI106796B/fi active
- 1994-06-10 NO NO942175A patent/NO300321B1/no unknown
-
1997
- 1997-03-12 GR GR960403249T patent/GR3022792T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES2097370T3 (es) | 1997-04-01 |
| ATE148686T1 (de) | 1997-02-15 |
| CA2125474A1 (en) | 1993-06-24 |
| EP0621861B1 (en) | 1997-02-05 |
| GR3022792T3 (en) | 1997-06-30 |
| FI942694A0 (fi) | 1994-06-08 |
| EP0621861A1 (en) | 1994-11-02 |
| DK0621861T3 (da) | 1997-07-28 |
| DE69217388T2 (de) | 1997-05-22 |
| CN1075711A (zh) | 1993-09-01 |
| WO1993012064A1 (en) | 1993-06-24 |
| BR9207023A (pt) | 1995-12-19 |
| DE69217388D1 (de) | 1997-03-20 |
| JPH07502035A (ja) | 1995-03-02 |
| IT1251708B (it) | 1995-05-20 |
| NO942175L (da) | 1994-06-10 |
| FI942694A (fi) | 1994-06-08 |
| US5336793A (en) | 1994-08-09 |
| AU658957B2 (en) | 1995-05-04 |
| ITTO910963A1 (it) | 1993-06-11 |
| FI106796B (fi) | 2001-04-12 |
| NO942175D0 (no) | 1994-06-10 |
| ITTO910963A0 (it) | 1991-12-11 |
| AU3085692A (en) | 1993-07-19 |
| IL103957A0 (en) | 1993-05-13 |
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