JP2002528428A - α，α−分岐状カルボン酸の製造方法 - Google Patents
α，α−分岐状カルボン酸の製造方法Info
- Publication number
- JP2002528428A JP2002528428A JP2000578272A JP2000578272A JP2002528428A JP 2002528428 A JP2002528428 A JP 2002528428A JP 2000578272 A JP2000578272 A JP 2000578272A JP 2000578272 A JP2000578272 A JP 2000578272A JP 2002528428 A JP2002528428 A JP 2002528428A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- catalyst
- reactor
- resin
- water
- 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.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 title claims abstract 3
- 239000003054 catalyst Substances 0.000 claims abstract description 36
- 239000002253 acid Substances 0.000 claims abstract description 29
- 150000001336 alkenes Chemical class 0.000 claims abstract description 26
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 18
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 14
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 8
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000002243 precursor Substances 0.000 claims abstract description 6
- UBDHSURDYAETAL-UHFFFAOYSA-N 8-aminonaphthalene-1,3,6-trisulfonic acid Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 UBDHSURDYAETAL-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000003960 organic solvent Substances 0.000 claims abstract description 3
- 239000002904 solvent Substances 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 21
- 150000001735 carboxylic acids Chemical group 0.000 claims description 20
- 229920005989 resin Polymers 0.000 claims description 13
- 239000011347 resin Substances 0.000 claims description 13
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 11
- 230000002378 acidificating effect Effects 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 229920001577 copolymer Polymers 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 6
- 239000002815 homogeneous catalyst Substances 0.000 claims description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 3
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000003729 cation exchange resin Substances 0.000 claims description 2
- -1 poly (tetrafluoroethylene) Polymers 0.000 claims description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims description 2
- 238000004064 recycling Methods 0.000 claims description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 2
- ACGZDZFDOTWGSE-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene 1-ethenylnaphthalene Chemical compound C=CC1=CC=CC=C1C=C.C1=CC=C2C(C=C)=CC=CC2=C1 ACGZDZFDOTWGSE-UHFFFAOYSA-N 0.000 claims 1
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 claims 1
- 230000000447 dimerizing effect Effects 0.000 claims 1
- 238000005342 ion exchange Methods 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 10
- 229910052799 carbon Inorganic materials 0.000 abstract description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 229920001429 chelating resin Polymers 0.000 description 14
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical class O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 9
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000000061 acid fraction Substances 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 239000002638 heterogeneous catalyst Substances 0.000 description 5
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 4
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000000539 dimer Substances 0.000 description 4
- SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000003377 acid catalyst Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 235000021588 free fatty acids Nutrition 0.000 description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 3
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 3
- 102000003729 Neprilysin Human genes 0.000 description 2
- 108090000028 Neprilysin Proteins 0.000 description 2
- 229910021536 Zeolite Inorganic materials 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- 239000012159 carrier gas Substances 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000001307 helium Substances 0.000 description 2
- 229910052734 helium Inorganic materials 0.000 description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- 239000011973 solid acid Substances 0.000 description 2
- 239000011949 solid catalyst Substances 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- 239000010457 zeolite Substances 0.000 description 2
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- HXQPUEQDBSPXTE-UHFFFAOYSA-N Diisobutylcarbinol Chemical compound CC(C)CC(O)CC(C)C HXQPUEQDBSPXTE-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 229920000557 Nafion® Polymers 0.000 description 1
- 101100273357 Pisum sativum AB80 gene Proteins 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000001243 acetic acids Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000004868 gas analysis Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- UAXOELSVPTZZQG-UHFFFAOYSA-N tiglic acid Natural products CC(C)=C(C)C(O)=O UAXOELSVPTZZQG-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
- C07C51/10—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/10—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide
- C07C51/12—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide on an oxygen-containing group in organic compounds, e.g. alcohols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/10—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide
- C07C51/14—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide on a carbon-to-carbon unsaturated bond in organic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98203575.0 | 1998-10-22 | ||
| EP98203575 | 1998-10-22 | ||
| PCT/EP1999/007931 WO2000024700A1 (en) | 1998-10-22 | 1999-10-19 | PROCESS FOR THE MANUFACTURE OF α,α-BRANCHED CARBOXYLIC ACIDS |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002528428A true JP2002528428A (ja) | 2002-09-03 |
| JP2002528428A5 JP2002528428A5 (enExample) | 2006-09-07 |
Family
ID=8234254
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000578272A Pending JP2002528428A (ja) | 1998-10-22 | 1999-10-19 | α，α−分岐状カルボン酸の製造方法 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6211406B1 (enExample) |
| EP (1) | EP1123264B1 (enExample) |
| JP (1) | JP2002528428A (enExample) |
| KR (1) | KR100633971B1 (enExample) |
| CN (1) | CN1177791C (enExample) |
| AR (1) | AR020910A1 (enExample) |
| AT (1) | ATE272042T1 (enExample) |
| AU (1) | AU6474599A (enExample) |
| CA (1) | CA2347756C (enExample) |
| DE (1) | DE69919014T2 (enExample) |
| HK (1) | HK1041478B (enExample) |
| WO (1) | WO2000024700A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005247851A (ja) * | 2004-03-06 | 2005-09-15 | Oxeno Olefinchemie Gmbh | 第三カルボン酸の製造方法及びその使用 |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1281700A1 (en) * | 2001-07-31 | 2003-02-05 | Resolution Research Nederland B.V. | Manufacturing process for the preparation of alpha, alpha-branched alkane carboxylic acids providing esters with an improved softness |
| US9174915B2 (en) * | 2010-06-04 | 2015-11-03 | Exxonmobil Chemical Patents Inc. | Extraction towers and processes for using the same |
| CN102503803B (zh) * | 2011-10-20 | 2013-12-04 | 广东食品药品职业学院 | 一种有机酸化合物及其提取方法与应用 |
| DE102013009323B4 (de) * | 2013-06-01 | 2018-09-20 | Oxea Gmbh | Verfahren zur Herstellung von Gemischen enthaltend tertiäre Isononansäuren ausgehend von 2-Ethylhexanol |
| CN103819328B (zh) * | 2014-02-13 | 2016-01-20 | 石家庄多维化工有限公司 | 一种2，2-二甲基丁酸的羰基化工艺 |
| CN106631756A (zh) * | 2016-12-14 | 2017-05-10 | 安阳师范学院 | 有机强酸催化合成有机羧酸的方法 |
| CN106631757A (zh) * | 2016-12-14 | 2017-05-10 | 安阳师范学院 | 杂多酸催化合成支链有机羧酸的方法 |
| CN106631755A (zh) * | 2016-12-14 | 2017-05-10 | 安阳师范学院 | 强酸性离子交换树脂催化合成有机羧酸的方法 |
| CN110551017B (zh) * | 2019-09-25 | 2021-02-26 | 西南化工研究设计院有限公司 | 一种液液传质催化合成叔羧酸的工艺与系统 |
| CN111359659B (zh) * | 2020-03-17 | 2021-02-09 | 西南化工研究设计院有限公司 | 一种合成叔羧酸的催化剂及应用及叔羧酸的合成方法 |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4823413B1 (enExample) * | 1969-10-25 | 1973-07-13 | ||
| JPS4995916A (enExample) * | 1973-01-29 | 1974-09-11 | ||
| JPS50123614A (enExample) * | 1974-03-15 | 1975-09-29 | ||
| JPS61118343A (ja) * | 1984-11-12 | 1986-06-05 | Agency Of Ind Science & Technol | カルボン酸及びカルボン酸誘導体の製造方法 |
| WO1998038149A1 (en) * | 1997-02-25 | 1998-09-03 | Shell Internationale Research Maatschappij B.V. | Process for the manufacture of carboxylic acids |
| JPH11315047A (ja) * | 1998-04-30 | 1999-11-16 | Agency Of Ind Science & Technol | 固体酸触媒による第三級カルボン酸の合成法 |
| JP2001513099A (ja) * | 1997-02-25 | 2001-08-28 | シエル・インターナシヨネイル・リサーチ・マーチヤツピイ・ベー・ウイ | カルボン酸の製造方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3965132A (en) * | 1974-06-03 | 1976-06-22 | Phillips Petroleum Company | Acid and ester production |
| DE3620581A1 (de) | 1986-06-19 | 1987-12-23 | Basf Ag | Verfahren zur herstellung von carbonsaeuren |
| DE4003232A1 (de) * | 1990-02-03 | 1991-08-22 | Huels Chemische Werke Ag | Verfahren zur herstellung von tertiaeren carbonsaeuren |
| US5241112A (en) | 1991-04-09 | 1993-08-31 | Catalytica, Inc. | Preparation of trialkylacetic acids, particularly of pivalic acid, using solid acid catalysis |
| CA2209164A1 (en) * | 1994-12-28 | 1996-07-04 | Keith R. Gorda | Production of trialkylacetic acids using a solid cationic resin catalyst system |
| MA24137A1 (fr) * | 1996-04-16 | 1997-12-31 | Procter & Gamble | Fabrication d'agents de surface ramifies . |
-
1999
- 1999-10-19 KR KR1020017004986A patent/KR100633971B1/ko not_active Expired - Fee Related
- 1999-10-19 DE DE69919014T patent/DE69919014T2/de not_active Expired - Lifetime
- 1999-10-19 AT AT99952612T patent/ATE272042T1/de not_active IP Right Cessation
- 1999-10-19 HK HK02102997.7A patent/HK1041478B/zh not_active IP Right Cessation
- 1999-10-19 EP EP99952612A patent/EP1123264B1/en not_active Expired - Lifetime
- 1999-10-19 JP JP2000578272A patent/JP2002528428A/ja active Pending
- 1999-10-19 CA CA002347756A patent/CA2347756C/en not_active Expired - Fee Related
- 1999-10-19 AU AU64745/99A patent/AU6474599A/en not_active Abandoned
- 1999-10-19 CN CNB998124400A patent/CN1177791C/zh not_active Expired - Fee Related
- 1999-10-19 WO PCT/EP1999/007931 patent/WO2000024700A1/en not_active Ceased
- 1999-10-20 AR ARP990105286A patent/AR020910A1/es unknown
- 1999-10-20 US US09/421,727 patent/US6211406B1/en not_active Expired - Fee Related
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4823413B1 (enExample) * | 1969-10-25 | 1973-07-13 | ||
| JPS4995916A (enExample) * | 1973-01-29 | 1974-09-11 | ||
| JPS50123614A (enExample) * | 1974-03-15 | 1975-09-29 | ||
| JPS61118343A (ja) * | 1984-11-12 | 1986-06-05 | Agency Of Ind Science & Technol | カルボン酸及びカルボン酸誘導体の製造方法 |
| WO1998038149A1 (en) * | 1997-02-25 | 1998-09-03 | Shell Internationale Research Maatschappij B.V. | Process for the manufacture of carboxylic acids |
| JP2001513099A (ja) * | 1997-02-25 | 2001-08-28 | シエル・インターナシヨネイル・リサーチ・マーチヤツピイ・ベー・ウイ | カルボン酸の製造方法 |
| JPH11315047A (ja) * | 1998-04-30 | 1999-11-16 | Agency Of Ind Science & Technol | 固体酸触媒による第三級カルボン酸の合成法 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005247851A (ja) * | 2004-03-06 | 2005-09-15 | Oxeno Olefinchemie Gmbh | 第三カルボン酸の製造方法及びその使用 |
Also Published As
| Publication number | Publication date |
|---|---|
| US6211406B1 (en) | 2001-04-03 |
| EP1123264A1 (en) | 2001-08-16 |
| CA2347756C (en) | 2009-12-29 |
| KR100633971B1 (ko) | 2006-10-16 |
| CN1324340A (zh) | 2001-11-28 |
| DE69919014T2 (de) | 2005-01-27 |
| WO2000024700A1 (en) | 2000-05-04 |
| KR20010099707A (ko) | 2001-11-09 |
| ATE272042T1 (de) | 2004-08-15 |
| CA2347756A1 (en) | 2000-05-04 |
| CN1177791C (zh) | 2004-12-01 |
| AU6474599A (en) | 2000-05-15 |
| EP1123264B1 (en) | 2004-07-28 |
| HK1041478A1 (en) | 2002-07-12 |
| AR020910A1 (es) | 2002-06-05 |
| DE69919014D1 (de) | 2004-09-02 |
| HK1041478B (zh) | 2005-05-06 |
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