DE1275050B - Verfahren zur Herstellung von olefinisch ungesaettigten Aldehyden und Ketonen - Google Patents
Verfahren zur Herstellung von olefinisch ungesaettigten Aldehyden und KetonenInfo
- Publication number
- DE1275050B DE1275050B DEB91482A DEB0091482A DE1275050B DE 1275050 B DE1275050 B DE 1275050B DE B91482 A DEB91482 A DE B91482A DE B0091482 A DEB0091482 A DE B0091482A DE 1275050 B DE1275050 B DE 1275050B
- Authority
- DE
- Germany
- Prior art keywords
- water
- dihydro
- parts
- ketones
- pyran
- 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
- 238000000034 method Methods 0.000 title claims description 10
- 150000001299 aldehydes Chemical class 0.000 title claims description 6
- 150000002576 ketones Chemical class 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 14
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 claims description 6
- 238000003385 ring cleavage reaction Methods 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 8
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 5
- 150000001728 carbonyl compounds Chemical class 0.000 description 5
- XOFPNIVQINAROR-UHFFFAOYSA-N 2,2,6-trimethyl-3,4-dihydropyran Chemical compound CC1=CCCC(C)(C)O1 XOFPNIVQINAROR-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000004508 fractional distillation Methods 0.000 description 3
- UKNWTHMYAXMTFF-UHFFFAOYSA-N 2-(2,2-dimethylpropyl)-2-methyl-3,4-dihydropyran Chemical group CC1(CCC=CO1)CC(C)(C)C UKNWTHMYAXMTFF-UHFFFAOYSA-N 0.000 description 2
- IZBMUZVSTLWUTH-UHFFFAOYSA-N 3-methylhept-3-en-2-one Chemical compound CCCC=C(C)C(C)=O IZBMUZVSTLWUTH-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001717 carbocyclic compounds Chemical class 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- LJNIRZXCJFJLRC-UHFFFAOYSA-N 1-methyl-3-methylidenecyclohexene Chemical compound CC1=CC(=C)CCC1 LJNIRZXCJFJLRC-UHFFFAOYSA-N 0.000 description 1
- SYTWCNXJNPSFQT-UHFFFAOYSA-N 2,2-dimethyl-3,4-dihydropyran Chemical compound CC1(C)CCC=CO1 SYTWCNXJNPSFQT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- -1 alkyl radicals Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-N sodium;hydron;carbonate Chemical compound [Na+].OC(O)=O UIIMBOGNXHQVGW-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
- C07C45/60—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in six-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB91482A DE1275050B (de) | 1967-03-06 | 1967-03-06 | Verfahren zur Herstellung von olefinisch ungesaettigten Aldehyden und Ketonen |
| FR1555118D FR1555118A (enrdf_load_stackoverflow) | 1967-03-06 | 1968-02-19 | |
| BE711133D BE711133A (enrdf_load_stackoverflow) | 1967-03-06 | 1968-02-22 | |
| CH280268A CH495933A (de) | 1967-03-06 | 1968-02-27 | Verfahren zur Herstellung von olefinisch ungesättigten Oxoverbindungen |
| NL6803048A NL151345B (nl) | 1967-03-06 | 1968-03-04 | Werkwijze voor het bereiden van alkenisch onverzadigde oxoverbindingen door verhitting van 6,6-dialkyl-5,6-dihydro-4h-pyranen. |
| GB1055468A GB1209199A (en) | 1967-03-06 | 1968-03-05 | Production of olefinically unsaturated oxo compounds |
| AT218168A AT274769B (de) | 1967-03-06 | 1968-03-06 | Verfahren zur Herstellung von olefinisch ungesättigten Oxoverbindungen |
| DK91968A DK119824B (da) | 1967-03-06 | 1968-03-06 | Fremgangsmåde til fremstilling af blandinger af alkenisk umættede oxoforbindelser. |
| ES351271A ES351271A1 (es) | 1967-03-06 | 1968-03-06 | Procedimiento para la obtencion de oxocompuestos olefinica-mente insaturados. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB91482A DE1275050B (de) | 1967-03-06 | 1967-03-06 | Verfahren zur Herstellung von olefinisch ungesaettigten Aldehyden und Ketonen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1275050B true DE1275050B (de) | 1968-08-14 |
Family
ID=6985861
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB91482A Pending DE1275050B (de) | 1967-03-06 | 1967-03-06 | Verfahren zur Herstellung von olefinisch ungesaettigten Aldehyden und Ketonen |
Country Status (9)
| Country | Link |
|---|---|
| AT (1) | AT274769B (enrdf_load_stackoverflow) |
| BE (1) | BE711133A (enrdf_load_stackoverflow) |
| CH (1) | CH495933A (enrdf_load_stackoverflow) |
| DE (1) | DE1275050B (enrdf_load_stackoverflow) |
| DK (1) | DK119824B (enrdf_load_stackoverflow) |
| ES (1) | ES351271A1 (enrdf_load_stackoverflow) |
| FR (1) | FR1555118A (enrdf_load_stackoverflow) |
| GB (1) | GB1209199A (enrdf_load_stackoverflow) |
| NL (1) | NL151345B (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4222943A (en) * | 1979-02-05 | 1980-09-16 | Hoffmann-La Roche Inc. | Process for the preparation of esters of 5-formyl-3-methyl-2,4-pentadien-1-ol |
| US4288614A (en) | 1979-02-05 | 1981-09-08 | Hoffmann-La Roche Inc. | Process for the preparation of esters of 5-formyl-3-methyl-2,4-pentadien-1-ol |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3686321A (en) * | 1971-01-18 | 1972-08-22 | Basf Ag | Production of 2-methylhept-1-en-6-one |
-
1967
- 1967-03-06 DE DEB91482A patent/DE1275050B/de active Pending
-
1968
- 1968-02-19 FR FR1555118D patent/FR1555118A/fr not_active Expired
- 1968-02-22 BE BE711133D patent/BE711133A/xx unknown
- 1968-02-27 CH CH280268A patent/CH495933A/de not_active IP Right Cessation
- 1968-03-04 NL NL6803048A patent/NL151345B/xx unknown
- 1968-03-05 GB GB1055468A patent/GB1209199A/en not_active Expired
- 1968-03-06 ES ES351271A patent/ES351271A1/es not_active Expired
- 1968-03-06 AT AT218168A patent/AT274769B/de active
- 1968-03-06 DK DK91968A patent/DK119824B/da unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4222943A (en) * | 1979-02-05 | 1980-09-16 | Hoffmann-La Roche Inc. | Process for the preparation of esters of 5-formyl-3-methyl-2,4-pentadien-1-ol |
| US4288614A (en) | 1979-02-05 | 1981-09-08 | Hoffmann-La Roche Inc. | Process for the preparation of esters of 5-formyl-3-methyl-2,4-pentadien-1-ol |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1209199A (en) | 1970-10-21 |
| NL6803048A (enrdf_load_stackoverflow) | 1968-09-09 |
| NL151345B (nl) | 1976-11-15 |
| ES351271A1 (es) | 1969-06-01 |
| AT274769B (de) | 1969-09-25 |
| BE711133A (enrdf_load_stackoverflow) | 1968-08-22 |
| FR1555118A (enrdf_load_stackoverflow) | 1969-01-24 |
| DK119824B (da) | 1971-03-01 |
| CH495933A (de) | 1970-09-15 |
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