GB1586805A - Manufacture of alkyl a-formylpropionates - Google Patents
Manufacture of alkyl a-formylpropionates Download PDFInfo
- Publication number
- GB1586805A GB1586805A GB3973777A GB3973777A GB1586805A GB 1586805 A GB1586805 A GB 1586805A GB 3973777 A GB3973777 A GB 3973777A GB 3973777 A GB3973777 A GB 3973777A GB 1586805 A GB1586805 A GB 1586805A
- Authority
- GB
- United Kingdom
- Prior art keywords
- rhodium
- complex
- alkyl
- acrylic acid
- compound
- 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
Links
- 125000000217 alkyl group Chemical group 0.000 title claims abstract description 19
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- 239000003054 catalyst Substances 0.000 claims abstract description 19
- -1 phosphorus compound Chemical class 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims abstract description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 5
- 239000011574 phosphorus Substances 0.000 claims abstract description 5
- 150000003283 rhodium Chemical class 0.000 claims abstract description 5
- 239000003446 ligand Substances 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 30
- 239000010948 rhodium Substances 0.000 claims description 24
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 24
- 229910052703 rhodium Inorganic materials 0.000 claims description 21
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 21
- 125000005396 acrylic acid ester group Chemical group 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 17
- 238000007037 hydroformylation reaction Methods 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 238000006116 polymerization reaction Methods 0.000 claims description 9
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 8
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 8
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 8
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 7
- 238000004821 distillation Methods 0.000 claims description 6
- 239000003112 inhibitor Substances 0.000 claims description 5
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 claims description 4
- 230000009918 complex formation Effects 0.000 claims description 3
- 238000000354 decomposition reaction Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- OPFTUNCRGUEPRZ-QLFBSQMISA-N Cyclohexane Natural products CC(=C)[C@@H]1CC[C@@](C)(C=C)[C@H](C(C)=C)C1 OPFTUNCRGUEPRZ-QLFBSQMISA-N 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- GGRQQHADVSXBQN-FGSKAQBVSA-N carbon monoxide;(z)-4-hydroxypent-3-en-2-one;rhodium Chemical compound [Rh].[O+]#[C-].[O+]#[C-].C\C(O)=C\C(C)=O GGRQQHADVSXBQN-FGSKAQBVSA-N 0.000 claims description 2
- 125000000687 hydroquinonyl group Chemical group C1(O)=C(C=C(O)C=C1)* 0.000 claims description 2
- 238000010952 in-situ formation Methods 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 230000018044 dehydration Effects 0.000 claims 1
- 238000006297 dehydration reaction Methods 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- VOKUMXABRRXHAR-UHFFFAOYSA-N 2-methyl-3-oxopropanoic acid Chemical class O=CC(C)C(O)=O VOKUMXABRRXHAR-UHFFFAOYSA-N 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 150000003003 phosphines Chemical class 0.000 description 3
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 3
- 150000003018 phosphorus compounds Chemical class 0.000 description 3
- 229910021604 Rhodium(III) chloride Inorganic materials 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 238000003512 Claisen condensation reaction Methods 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical class OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000006845 Michael addition reaction Methods 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 150000001869 cobalt compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000003151 propanoic acid esters Chemical class 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- VXNYVYJABGOSBX-UHFFFAOYSA-N rhodium(3+);trinitrate Chemical compound [Rh+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VXNYVYJABGOSBX-UHFFFAOYSA-N 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07C67/343—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 by increase in the number of carbon atoms
- C07C67/347—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 by increase in the number of carbon atoms by addition to unsaturated carbon-to-carbon bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762643205 DE2643205A1 (de) | 1976-09-25 | 1976-09-25 | Verfahren zur herstellung von alpha-formylpropionsaeurealkylestern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1586805A true GB1586805A (en) | 1981-03-25 |
Family
ID=5988818
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3973777A Expired GB1586805A (en) | 1976-09-25 | 1977-09-23 | Manufacture of alkyl a-formylpropionates |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS5340716A (enrdf_load_stackoverflow) |
| BE (1) | BE858725A (enrdf_load_stackoverflow) |
| CH (1) | CH629175A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2643205A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2365549A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1586805A (enrdf_load_stackoverflow) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4496769A (en) * | 1982-06-11 | 1985-01-29 | Davy Mckee (London) Limited | Process for the preparation of aldehydes by hydroformylation of olefins |
| US4496768A (en) * | 1982-06-11 | 1985-01-29 | Davy Mckee Limited | Process for the production of aldehydes by hydroformylation of alpha-olefins |
| EP0295553A1 (de) * | 1987-06-13 | 1988-12-21 | BASF Aktiengesellschaft | Verfahren zur Herstelung von 1,1-disubstituierten Ethylenverbindungen |
| US4801738A (en) * | 1983-05-11 | 1989-01-31 | Basf Aktiengesellschaft | Preparation of δ-formylvalerates |
| US4910328A (en) * | 1987-06-15 | 1990-03-20 | Basf Akteingesellschaft | Preparation of omega-formylalkanecarboxylic esters |
| GB2274457A (en) * | 1993-01-25 | 1994-07-27 | Shell Int Research | Hydroformylation of unsaturated carbonyl compounds |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8720510D0 (en) * | 1987-09-01 | 1987-10-07 | Shell Int Research | Hydroformulation of alkyl acrylates |
| DE3930886A1 (de) * | 1989-09-15 | 1991-03-28 | Hoechst Ag | Verfahren zur herstellung von 2-formylbuttersaeuremethylester |
| GB9200448D0 (en) * | 1992-01-10 | 1992-02-26 | British Petroleum Co Plc | Hydroformylation process |
| AT1814U1 (de) * | 1997-01-20 | 1997-12-29 | Karl Wallisch | Holzkohlen-heissluftgriller |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2301502A1 (fr) * | 1975-02-18 | 1976-09-17 | Du Pont | Procede d'hydroformylation des olefines |
| JPS5273822A (en) * | 1975-12-16 | 1977-06-21 | Agency Of Ind Science & Technol | Production of alpha-formylcarboxylic acid esters |
-
1976
- 1976-09-25 DE DE19762643205 patent/DE2643205A1/de not_active Withdrawn
-
1977
- 1977-09-09 FR FR7727306A patent/FR2365549A1/fr active Granted
- 1977-09-15 BE BE180930A patent/BE858725A/xx not_active IP Right Cessation
- 1977-09-21 CH CH1156277A patent/CH629175A5/de not_active IP Right Cessation
- 1977-09-22 JP JP11338677A patent/JPS5340716A/ja active Pending
- 1977-09-23 GB GB3973777A patent/GB1586805A/en not_active Expired
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4496769A (en) * | 1982-06-11 | 1985-01-29 | Davy Mckee (London) Limited | Process for the preparation of aldehydes by hydroformylation of olefins |
| US4496768A (en) * | 1982-06-11 | 1985-01-29 | Davy Mckee Limited | Process for the production of aldehydes by hydroformylation of alpha-olefins |
| US4801738A (en) * | 1983-05-11 | 1989-01-31 | Basf Aktiengesellschaft | Preparation of δ-formylvalerates |
| EP0295553A1 (de) * | 1987-06-13 | 1988-12-21 | BASF Aktiengesellschaft | Verfahren zur Herstelung von 1,1-disubstituierten Ethylenverbindungen |
| US4997955A (en) * | 1987-06-13 | 1991-03-05 | Basf Aktiengesellschaft | Preparation of 1,1-disubstituted ethylene compounds |
| US4910328A (en) * | 1987-06-15 | 1990-03-20 | Basf Akteingesellschaft | Preparation of omega-formylalkanecarboxylic esters |
| GB2274457A (en) * | 1993-01-25 | 1994-07-27 | Shell Int Research | Hydroformylation of unsaturated carbonyl compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2365549B1 (enrdf_load_stackoverflow) | 1982-08-13 |
| DE2643205A1 (de) | 1978-03-30 |
| FR2365549A1 (fr) | 1978-04-21 |
| BE858725A (fr) | 1978-03-15 |
| JPS5340716A (en) | 1978-04-13 |
| CH629175A5 (en) | 1982-04-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |