CA2079763C - Procede de preparation de l'acide adipique par hydrocarboxylation d'acides penteniques - Google Patents
Procede de preparation de l'acide adipique par hydrocarboxylation d'acides penteniques Download PDFInfo
- Publication number
- CA2079763C CA2079763C CA002079763A CA2079763A CA2079763C CA 2079763 C CA2079763 C CA 2079763C CA 002079763 A CA002079763 A CA 002079763A CA 2079763 A CA2079763 A CA 2079763A CA 2079763 C CA2079763 C CA 2079763C
- Authority
- CA
- Canada
- Prior art keywords
- acid
- reaction
- character
- solvent
- pentene
- 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
- 238000000034 method Methods 0.000 title claims abstract description 42
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 239000001361 adipic acid Substances 0.000 title claims abstract description 8
- 235000011037 adipic acid Nutrition 0.000 title claims abstract description 8
- YIYBQIKDCADOSF-UHFFFAOYSA-N pent-2-enoic acid Chemical class CCC=CC(O)=O YIYBQIKDCADOSF-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- 239000002904 solvent Substances 0.000 claims abstract description 18
- 229910052741 iridium Inorganic materials 0.000 claims abstract description 15
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 13
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 10
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 4
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 239000003054 catalyst Substances 0.000 claims abstract description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 3
- 150000002170 ethers Chemical class 0.000 claims abstract 2
- 239000002253 acid Substances 0.000 claims description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- HVFSJXUIRWUHRG-UHFFFAOYSA-N oic acid Natural products C1CC2C3CC=C4CC(OC5C(C(O)C(O)C(CO)O5)O)CC(O)C4(C)C3CCC2(C)C1C(C)C(O)CC(C)=C(C)C(=O)OC1OC(COC(C)=O)C(O)C(O)C1OC(C(C1O)O)OC(COC(C)=O)C1OC1OC(CO)C(O)C(O)C1O HVFSJXUIRWUHRG-UHFFFAOYSA-N 0.000 claims description 11
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000012429 reaction media Substances 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 9
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 4
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 claims description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 239000011630 iodine Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 claims description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 abstract description 2
- 150000002430 hydrocarbons Chemical class 0.000 abstract description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 150000001735 carboxylic acids Chemical class 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 4
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- XJMMNTGIMDZPMU-UHFFFAOYSA-N 3-methylglutaric acid Chemical compound OC(=O)CC(C)CC(O)=O XJMMNTGIMDZPMU-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 239000003708 ampul Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 230000017105 transposition Effects 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- RVHOBHMAPRVOLO-UHFFFAOYSA-N 2-ethylbutanedioic acid Chemical compound CCC(C(O)=O)CC(O)=O RVHOBHMAPRVOLO-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- -1 aliphatic ethers Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005810 carbonylation reaction Methods 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
- C07C55/02—Dicarboxylic acids
- C07C55/14—Adipic acid
-
- 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9112392 | 1991-10-03 | ||
| FR9112392A FR2682104A1 (fr) | 1991-10-03 | 1991-10-03 | Procede de preparation de l'acide adipique par hydrocarboxylation d'acides penteniques. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2079763A1 CA2079763A1 (fr) | 1993-04-04 |
| CA2079763C true CA2079763C (fr) | 2003-01-07 |
Family
ID=9417718
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002079763A Expired - Fee Related CA2079763C (fr) | 1991-10-03 | 1992-10-02 | Procede de preparation de l'acide adipique par hydrocarboxylation d'acides penteniques |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US5420346A (OSRAM) |
| EP (1) | EP0536064B1 (OSRAM) |
| JP (1) | JPH0692340B2 (OSRAM) |
| KR (1) | KR100250337B1 (OSRAM) |
| CN (1) | CN1030071C (OSRAM) |
| CA (1) | CA2079763C (OSRAM) |
| CZ (1) | CZ279863B6 (OSRAM) |
| DE (1) | DE69204006T2 (OSRAM) |
| ES (1) | ES2076726T3 (OSRAM) |
| FR (1) | FR2682104A1 (OSRAM) |
| MX (1) | MX9205640A (OSRAM) |
| RU (1) | RU2068406C1 (OSRAM) |
| SK (1) | SK279905B6 (OSRAM) |
| TW (1) | TW227995B (OSRAM) |
| UA (1) | UA34427C2 (OSRAM) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2714306B1 (fr) * | 1993-12-29 | 1996-09-27 | Rhone Poulenc Chimie | Procédé de préparation d'une solution à base d'iridium et son utilisation en tant que catalyseur. |
| US5292944A (en) * | 1993-06-29 | 1994-03-08 | E. I. Du Pont De Nemours And Company | Process for the preparation of adipic acid or pentenoic acid |
| FR2721019B1 (fr) | 1994-06-14 | 1996-09-06 | Rhone Poulenc Chimie | Procédé de séparation de diacides aliphatiques à partir de leurs mélanges avec l'acide adipique. |
| US5883265A (en) * | 1997-04-15 | 1999-03-16 | Union Carbide Chemicals & Plastics Technology Corporation | Processes for producing epsilon caprolactones and/or hydrates and/or esters thereof |
| US6184391B1 (en) | 1997-04-15 | 2001-02-06 | Union Carbide Chemicals & Plastics Technology Corporation | Processes for producing epsilon caprolactones and/or hydrates and/or esters thereof |
| CN113845408B (zh) * | 2021-10-27 | 2023-02-03 | 南京延长反应技术研究院有限公司 | 一种催化剂进行烯烃羰基化的方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3579551A (en) * | 1968-08-15 | 1971-05-18 | Monsanto Co | Production of carboxylic acids |
| US3816489A (en) | 1968-08-15 | 1974-06-11 | Monsanto Co | Increasing the selectivity and yield in the production of carboxylic acids |
| BE793203A (fr) * | 1971-12-27 | 1973-06-22 | Monsanto Co | Production d'acides carboxyliques |
| US4788333A (en) * | 1985-01-07 | 1988-11-29 | E. I. Du Pont De Nemours And Company | Hydrocarboxylation of unsaturated carboxylic acids to linear dicarboxylic acids |
-
1991
- 1991-10-03 FR FR9112392A patent/FR2682104A1/fr active Granted
-
1992
- 1992-09-09 TW TW081107122A patent/TW227995B/zh active
- 1992-09-24 JP JP4277733A patent/JPH0692340B2/ja not_active Expired - Fee Related
- 1992-09-28 DE DE69204006T patent/DE69204006T2/de not_active Expired - Fee Related
- 1992-09-28 ES ES92420335T patent/ES2076726T3/es not_active Expired - Lifetime
- 1992-09-28 EP EP92420335A patent/EP0536064B1/fr not_active Expired - Lifetime
- 1992-09-29 US US07/953,092 patent/US5420346A/en not_active Expired - Fee Related
- 1992-09-30 SK SK2993-92A patent/SK279905B6/sk unknown
- 1992-09-30 CZ CS922993A patent/CZ279863B6/cs not_active IP Right Cessation
- 1992-09-30 CN CN92112011A patent/CN1030071C/zh not_active Expired - Fee Related
- 1992-10-01 KR KR1019920017971A patent/KR100250337B1/ko not_active Expired - Fee Related
- 1992-10-01 MX MX9205640A patent/MX9205640A/es not_active IP Right Cessation
- 1992-10-02 RU SU5052696/04A patent/RU2068406C1/ru not_active IP Right Cessation
- 1992-10-02 CA CA002079763A patent/CA2079763C/fr not_active Expired - Fee Related
-
1993
- 1993-06-15 UA UA93002931A patent/UA34427C2/uk unknown
Also Published As
| Publication number | Publication date |
|---|---|
| TW227995B (OSRAM) | 1994-08-11 |
| CZ279863B6 (cs) | 1995-07-12 |
| CN1030071C (zh) | 1995-10-18 |
| DE69204006T2 (de) | 1996-02-01 |
| KR930007886A (ko) | 1993-05-20 |
| FR2682104B1 (OSRAM) | 1994-08-19 |
| DE69204006D1 (de) | 1995-09-14 |
| US5420346A (en) | 1995-05-30 |
| UA34427C2 (uk) | 2001-03-15 |
| SK279905B6 (sk) | 1999-05-07 |
| CA2079763A1 (fr) | 1993-04-04 |
| SK299392A3 (en) | 1995-02-08 |
| JPH05238984A (ja) | 1993-09-17 |
| MX9205640A (es) | 1993-06-01 |
| FR2682104A1 (fr) | 1993-04-09 |
| RU2068406C1 (ru) | 1996-10-27 |
| EP0536064B1 (fr) | 1995-08-09 |
| CN1071159A (zh) | 1993-04-21 |
| EP0536064A1 (fr) | 1993-04-07 |
| CZ299392A3 (en) | 1993-04-14 |
| ES2076726T3 (es) | 1995-11-01 |
| KR100250337B1 (ko) | 2000-04-01 |
| JPH0692340B2 (ja) | 1994-11-16 |
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| FR2714306A1 (fr) | Procédé de préparation d'une solution à base d'iridium et son utilisation en tant que catalyseur. | |
| CA2052442C (fr) | Procede de preparation de l'acide adipique par hydrocarboxylation d'acides penteniques | |
| EP0039652B1 (fr) | Préparation de l'acide acétique par carbonylation | |
| EP0687663A1 (fr) | Procédé de séparation de diacides aliphatiques à partir de leurs mélanges avec l'acide adipique | |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |