CA2116502C - Procede d'hydroxycarbonylation de lactones - Google Patents
Procede d'hydroxycarbonylation de lactonesInfo
- Publication number
- CA2116502C CA2116502C CA002116502A CA2116502A CA2116502C CA 2116502 C CA2116502 C CA 2116502C CA 002116502 A CA002116502 A CA 002116502A CA 2116502 A CA2116502 A CA 2116502A CA 2116502 C CA2116502 C CA 2116502C
- Authority
- CA
- Canada
- Prior art keywords
- reaction
- lactone
- liter
- water
- reaction mixture
- 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 35
- 150000002596 lactones Chemical class 0.000 title claims abstract description 30
- 238000006243 chemical reaction Methods 0.000 claims abstract description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 23
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 claims abstract description 21
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims abstract description 16
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229910052741 iridium Inorganic materials 0.000 claims abstract description 15
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 13
- 239000003054 catalyst Substances 0.000 claims abstract description 13
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 7
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910000043 hydrogen iodide Inorganic materials 0.000 claims abstract description 7
- 239000007791 liquid phase Substances 0.000 claims abstract description 5
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
- 239000011541 reaction mixture Substances 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- IABBAPSDOJPBAF-UHFFFAOYSA-N 3,4-dimethyloxetan-2-one Chemical compound CC1OC(=O)C1C IABBAPSDOJPBAF-UHFFFAOYSA-N 0.000 claims description 2
- XTGSXZNTCQDKDF-UHFFFAOYSA-N 3-ethyloxetan-2-one Chemical compound CCC1COC1=O XTGSXZNTCQDKDF-UHFFFAOYSA-N 0.000 claims description 2
- QTWLQDVFHKLZRA-UHFFFAOYSA-N 4-ethyloxetan-2-one Chemical compound CCC1CC(=O)O1 QTWLQDVFHKLZRA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 229910021638 Iridium(III) chloride Inorganic materials 0.000 claims 2
- HATJNMZTHKSSHU-UHFFFAOYSA-N 3-ethyl-3-methyloxiran-2-one Chemical compound CCC1(C)OC1=O HATJNMZTHKSSHU-UHFFFAOYSA-N 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 1
- 125000001309 chloro group Chemical class Cl* 0.000 claims 1
- HTXDPTMKBJXEOW-UHFFFAOYSA-N iridium(IV) oxide Inorganic materials O=[Ir]=O HTXDPTMKBJXEOW-UHFFFAOYSA-N 0.000 claims 1
- 239000012071 phase Substances 0.000 claims 1
- 229930195734 saturated hydrocarbon Natural products 0.000 claims 1
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 claims 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 abstract description 35
- 239000001361 adipic acid Substances 0.000 abstract description 15
- 235000011037 adipic acid Nutrition 0.000 abstract description 15
- 238000005810 carbonylation reaction Methods 0.000 abstract description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- WVUYYXUATWMVIT-UHFFFAOYSA-N 1-bromo-4-ethoxybenzene Chemical compound CCOC1=CC=C(Br)C=C1 WVUYYXUATWMVIT-UHFFFAOYSA-N 0.000 description 11
- RVHOBHMAPRVOLO-UHFFFAOYSA-N 2-ethylbutanedioic acid Chemical compound CCC(C(O)=O)CC(O)=O RVHOBHMAPRVOLO-UHFFFAOYSA-N 0.000 description 11
- 230000009466 transformation Effects 0.000 description 9
- 229940005605 valeric acid Drugs 0.000 description 6
- YIYBQIKDCADOSF-UHFFFAOYSA-N pentenoic acid group Chemical class C(C=CCC)(=O)O YIYBQIKDCADOSF-UHFFFAOYSA-N 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052703 rhodium Inorganic materials 0.000 description 3
- 239000010948 rhodium Substances 0.000 description 3
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 3
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- -1 iodide hydrogen Chemical class 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- 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
- WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- QGLBZNZGBLRJGS-UHFFFAOYSA-N Dihydro-3-methyl-2(3H)-furanone Chemical compound CC1CCOC1=O QGLBZNZGBLRJGS-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- YFONKFDEZLYQDH-OPQQBVKSSA-N N-[(1R,2S)-2,6-dimethyindan-1-yl]-6-[(1R)-1-fluoroethyl]-1,3,5-triazine-2,4-diamine Chemical compound C[C@@H](F)C1=NC(N)=NC(N[C@H]2C3=CC(C)=CC=C3C[C@@H]2C)=N1 YFONKFDEZLYQDH-OPQQBVKSSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 235000013675 iodine Nutrition 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 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 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 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
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
- 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
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)
- Coloring Foods And Improving Nutritive Qualities (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9302483 | 1993-02-26 | ||
| FR9302483A FR2701944B1 (fr) | 1993-02-26 | 1993-02-26 | Procédé d'hydroxycarbonylation de lactones en acides dicarboxyliques aliphatiques. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2116502A1 CA2116502A1 (fr) | 1994-08-27 |
| CA2116502C true CA2116502C (fr) | 1999-05-25 |
Family
ID=9444632
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002116502A Expired - Fee Related CA2116502C (fr) | 1993-02-26 | 1994-02-25 | Procede d'hydroxycarbonylation de lactones |
Country Status (18)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US5710325A (en) * | 1996-11-01 | 1998-01-20 | E. I. Du Pont De Nemours And Company | Manufacture of adipic acid |
| CN115445662B (zh) * | 2022-08-31 | 2023-08-15 | 迈奇化学股份有限公司 | γ-丁内酯羰基化用催化剂及由γ-丁内酯合成戊二酸的方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU561506A3 (ru) * | 1967-04-05 | 1977-06-05 | Молсанто Компани (Фирма) | Способ получени алифатических или ароматических кислот и/или их сложных эфиров |
| DE1941448A1 (de) * | 1968-08-15 | 1970-04-23 | Monsanto Co | Verfahren zur Herstellung von Dicarbonsaeuren |
| US5359137A (en) * | 1989-04-26 | 1994-10-25 | E. I. Du Pont De Nemours And Company | Preparation of adipic acid from lactones |
-
1993
- 1993-02-26 FR FR9302483A patent/FR2701944B1/fr not_active Expired - Fee Related
-
1994
- 1994-02-10 EP EP94420044A patent/EP0612711B1/fr not_active Expired - Lifetime
- 1994-02-10 DE DE69400716T patent/DE69400716T2/de not_active Expired - Fee Related
- 1994-02-10 UA UA94005086A patent/UA41274C2/uk unknown
- 1994-02-10 ES ES94420044T patent/ES2093501T3/es not_active Expired - Lifetime
- 1994-02-10 SG SG1996004147A patent/SG45344A1/en unknown
- 1994-02-23 MX MX9401359A patent/MX9401359A/es not_active IP Right Cessation
- 1994-02-24 SK SK221-94A patent/SK281749B6/sk unknown
- 1994-02-24 PL PL94302364A patent/PL174036B1/pl not_active IP Right Cessation
- 1994-02-24 BR BR9400670A patent/BR9400670A/pt not_active IP Right Cessation
- 1994-02-24 CZ CZ1994422A patent/CZ289016B6/cs not_active IP Right Cessation
- 1994-02-25 CA CA002116502A patent/CA2116502C/fr not_active Expired - Fee Related
- 1994-02-25 RU RU94006278/04A patent/RU2117656C1/ru not_active IP Right Cessation
- 1994-02-25 CN CN94102519A patent/CN1049648C/zh not_active Expired - Fee Related
- 1994-02-25 JP JP6051108A patent/JP2512386B2/ja not_active Expired - Fee Related
- 1994-02-26 KR KR1019940003594A patent/KR0133557B1/ko not_active Expired - Fee Related
- 1994-03-30 TW TW083102736A patent/TW264468B/zh active
-
1996
- 1996-12-19 GR GR960403553T patent/GR3022119T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPH06256252A (ja) | 1994-09-13 |
| FR2701944B1 (fr) | 1995-05-19 |
| PL174036B1 (pl) | 1998-06-30 |
| UA41274C2 (uk) | 2001-09-17 |
| FR2701944A1 (fr) | 1994-09-02 |
| CN1049648C (zh) | 2000-02-23 |
| PL302364A1 (en) | 1994-09-05 |
| EP0612711B1 (fr) | 1996-10-16 |
| CZ42294A3 (en) | 1994-09-14 |
| BR9400670A (pt) | 1994-09-27 |
| CA2116502A1 (fr) | 1994-08-27 |
| SK22194A3 (en) | 1994-10-05 |
| TW264468B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1995-12-01 |
| SK281749B6 (sk) | 2001-07-10 |
| MX9401359A (es) | 1994-08-31 |
| JP2512386B2 (ja) | 1996-07-03 |
| GR3022119T3 (en) | 1997-03-31 |
| RU2117656C1 (ru) | 1998-08-20 |
| DE69400716D1 (de) | 1996-11-21 |
| EP0612711A1 (fr) | 1994-08-31 |
| DE69400716T2 (de) | 1997-03-06 |
| CZ289016B6 (cs) | 2001-10-17 |
| SG45344A1 (en) | 1998-01-16 |
| CN1104624A (zh) | 1995-07-05 |
| ES2093501T3 (es) | 1996-12-16 |
| KR0133557B1 (ko) | 1998-04-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |