CA2344451C - Process for the manufacture of quaternary carboxylic acids - Google Patents
Process for the manufacture of quaternary carboxylic acids Download PDFInfo
- Publication number
- CA2344451C CA2344451C CA002344451A CA2344451A CA2344451C CA 2344451 C CA2344451 C CA 2344451C CA 002344451 A CA002344451 A CA 002344451A CA 2344451 A CA2344451 A CA 2344451A CA 2344451 C CA2344451 C CA 2344451C
- Authority
- CA
- Canada
- Prior art keywords
- process according
- acid
- reactor
- catalyst
- range
- 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 - Fee Related
Links
- 150000001735 carboxylic acids Chemical group 0.000 title claims abstract description 31
- 238000000034 method Methods 0.000 title claims abstract description 31
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 15
- 239000002253 acid Substances 0.000 claims abstract description 38
- 150000001336 alkenes Chemical class 0.000 claims abstract description 31
- 239000003054 catalyst Substances 0.000 claims abstract description 29
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 230000002378 acidificating effect Effects 0.000 claims abstract description 8
- 239000002243 precursor Substances 0.000 claims abstract description 8
- 150000002500 ions Chemical class 0.000 claims abstract description 6
- 239000011973 solid acid Substances 0.000 claims abstract description 6
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000002904 solvent Substances 0.000 claims description 21
- 229920005989 resin Polymers 0.000 claims description 16
- 239000011347 resin Substances 0.000 claims description 16
- 239000007787 solid Substances 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 229920001577 copolymer Polymers 0.000 claims description 7
- 239000001117 sulphuric acid Substances 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 235000011149 sulphuric acid Nutrition 0.000 claims description 6
- 229920000642 polymer Polymers 0.000 claims description 5
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- -1 poly(tetrafluoro-ethylene) Polymers 0.000 claims description 4
- 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 description 2
- 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 description 2
- 238000004064 recycling Methods 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 150000007513 acids Chemical class 0.000 description 28
- 229920001429 chelating resin Polymers 0.000 description 12
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 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
- SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000011949 solid catalyst Substances 0.000 description 3
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- 229920000557 Nafion® Polymers 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 229940116441 divinylbenzene Drugs 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical class O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000010457 zeolite Substances 0.000 description 2
- 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 description 1
- OAOABCKPVCUNKO-UHFFFAOYSA-N 8-methyl Nonanoic acid Chemical compound CC(C)CCCCCCC(O)=O OAOABCKPVCUNKO-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006473 carboxylation reaction Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 230000020477 pH reduction Effects 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
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98203165 | 1998-09-21 | ||
| EP98203165.0 | 1998-09-21 | ||
| PCT/EP1999/006998 WO2000017146A1 (en) | 1998-09-21 | 1999-09-15 | Process for the manufacture of quaternary carboxylic acids |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2344451A1 CA2344451A1 (en) | 2000-03-30 |
| CA2344451C true CA2344451C (en) | 2009-04-07 |
Family
ID=8234142
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002344451A Expired - Fee Related CA2344451C (en) | 1998-09-21 | 1999-09-15 | Process for the manufacture of quaternary carboxylic acids |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP1115684B1 (enExample) |
| JP (1) | JP2002526464A (enExample) |
| KR (1) | KR100618260B1 (enExample) |
| CN (1) | CN1134396C (enExample) |
| AR (1) | AR020471A1 (enExample) |
| AU (1) | AU5980699A (enExample) |
| BR (1) | BR9913968A (enExample) |
| CA (1) | CA2344451C (enExample) |
| DE (1) | DE69904615T2 (enExample) |
| TW (1) | TW491834B (enExample) |
| WO (1) | WO2000017146A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2618778C (en) * | 2007-01-23 | 2016-04-05 | Linde, Inc. | Process for removing contaminants from gas streams |
| 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 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS50123614A (enExample) * | 1974-03-15 | 1975-09-29 | ||
| JPS6176434A (ja) * | 1984-09-21 | 1986-04-18 | Idemitsu Petrochem Co Ltd | 第３級カルボン酸の製造方法 |
| 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 |
| DE69512680T2 (de) * | 1994-12-28 | 2000-05-25 | Exxon Chemical Patents, Inc. | Herstellung von trialkylcarbonsäuren unter verwendung eines festen sauren harzkatalysatorsystems |
| WO1998038149A1 (en) * | 1997-02-25 | 1998-09-03 | Shell Internationale Research Maatschappij B.V. | Process for the manufacture of carboxylic acids |
| EP0968166B1 (en) * | 1997-02-25 | 2002-06-12 | Resolution Research Nederland 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 |
-
1999
- 1999-09-01 TW TW088115042A patent/TW491834B/zh not_active IP Right Cessation
- 1999-09-15 CA CA002344451A patent/CA2344451C/en not_active Expired - Fee Related
- 1999-09-15 CN CNB998111929A patent/CN1134396C/zh not_active Expired - Fee Related
- 1999-09-15 WO PCT/EP1999/006998 patent/WO2000017146A1/en not_active Ceased
- 1999-09-15 BR BR9913968-5A patent/BR9913968A/pt not_active Application Discontinuation
- 1999-09-15 EP EP99969406A patent/EP1115684B1/en not_active Expired - Lifetime
- 1999-09-15 JP JP2000574056A patent/JP2002526464A/ja active Pending
- 1999-09-15 AU AU59806/99A patent/AU5980699A/en not_active Abandoned
- 1999-09-15 DE DE69904615T patent/DE69904615T2/de not_active Expired - Lifetime
- 1999-09-15 KR KR1020017003447A patent/KR100618260B1/ko not_active Expired - Fee Related
- 1999-09-17 AR ARP990104675A patent/AR020471A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE69904615T2 (de) | 2004-07-01 |
| KR100618260B1 (ko) | 2006-09-01 |
| EP1115684A1 (en) | 2001-07-18 |
| TW491834B (en) | 2002-06-21 |
| CN1134396C (zh) | 2004-01-14 |
| AR020471A1 (es) | 2002-05-15 |
| CA2344451A1 (en) | 2000-03-30 |
| EP1115684B1 (en) | 2002-12-18 |
| CN1319082A (zh) | 2001-10-24 |
| AU5980699A (en) | 2000-04-10 |
| BR9913968A (pt) | 2001-07-03 |
| JP2002526464A (ja) | 2002-08-20 |
| WO2000017146A1 (en) | 2000-03-30 |
| DE69904615D1 (de) | 2003-01-30 |
| KR20010075171A (ko) | 2001-08-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20130917 |