GB799797A - An improved process for the manufacture of unsaturated ketones - Google Patents
An improved process for the manufacture of unsaturated ketonesInfo
- Publication number
- GB799797A GB799797A GB11631/56A GB1163156A GB799797A GB 799797 A GB799797 A GB 799797A GB 11631/56 A GB11631/56 A GB 11631/56A GB 1163156 A GB1163156 A GB 1163156A GB 799797 A GB799797 A GB 799797A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- acetoacetate
- dimethyl
- allyl acetoacetate
- heptene
- 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
- 150000002576 ketones Chemical class 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- -1 1 - methyl - 1 - isobutyl Chemical group 0.000 abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 abstract 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 3
- 229910052782 aluminium Inorganic materials 0.000 abstract 3
- 239000004411 aluminium Substances 0.000 abstract 3
- 150000002148 esters Chemical class 0.000 abstract 3
- 238000010438 heat treatment Methods 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 150000004729 acetoacetic acid derivatives Chemical class 0.000 abstract 2
- 125000002015 acyclic group Chemical group 0.000 abstract 2
- FGRBYDKOBBBPOI-UHFFFAOYSA-N 10,10-dioxo-2-[4-(N-phenylanilino)phenyl]thioxanthen-9-one Chemical compound O=C1c2ccccc2S(=O)(=O)c2ccc(cc12)-c1ccc(cc1)N(c1ccccc1)c1ccccc1 FGRBYDKOBBBPOI-UHFFFAOYSA-N 0.000 abstract 1
- NJAYZISKWWQCJX-UHFFFAOYSA-N 2-methylhept-6-en-3-one Chemical compound CC(C)C(=O)CCC=C NJAYZISKWWQCJX-UHFFFAOYSA-N 0.000 abstract 1
- KRCFMKYZBGJEEB-UHFFFAOYSA-N 3,7,9-trimethyldeca-1,3-diene Chemical compound CC(C=C)=CCCC(CC(C)C)C KRCFMKYZBGJEEB-UHFFFAOYSA-N 0.000 abstract 1
- FNHUIKVAXPPHGK-UHFFFAOYSA-N 5,6-dimethylhept-1-ene Chemical compound CC(C)C(C)CCC=C FNHUIKVAXPPHGK-UHFFFAOYSA-N 0.000 abstract 1
- PQIXRYBSJBIXHN-UHFFFAOYSA-N 5-cyclohexylidenepentan-2-one Chemical compound CC(=O)CCC=C1CCCCC1 PQIXRYBSJBIXHN-UHFFFAOYSA-N 0.000 abstract 1
- XCWXYMKORNQZLM-UHFFFAOYSA-N 6,10,12-trimethyltrideca-1,3-diene Chemical compound CC(CC=CC=C)CCCC(CC(C)C)C XCWXYMKORNQZLM-UHFFFAOYSA-N 0.000 abstract 1
- WZFHIOCDQWLJLW-UHFFFAOYSA-N 6,10,14-trimethylpentadec-1-en-5-one Chemical compound CC(C)CCCC(C)CCCC(C)C(=O)CCC=C WZFHIOCDQWLJLW-UHFFFAOYSA-N 0.000 abstract 1
- TYOUZFFEYBAYBV-UHFFFAOYSA-N 6,8-dimethylnon-1-en-5-one Chemical compound CC(C)CC(C)C(=O)CCC=C TYOUZFFEYBAYBV-UHFFFAOYSA-N 0.000 abstract 1
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 238000013019 agitation Methods 0.000 abstract 1
- 150000004703 alkoxides Chemical class 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- FNIATMYXUPOJRW-UHFFFAOYSA-N cyclohexylidene Chemical group [C]1CCCCC1 FNIATMYXUPOJRW-UHFFFAOYSA-N 0.000 abstract 1
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 abstract 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 abstract 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 abstract 1
- 238000004508 fractional distillation Methods 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 239000003208 petroleum Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 229960005235 piperonyl butoxide Drugs 0.000 abstract 1
- AXLMPTNTPOWPLT-UHFFFAOYSA-N prop-2-enyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCC=C AXLMPTNTPOWPLT-UHFFFAOYSA-N 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- UAEJRRZPRZCUBE-UHFFFAOYSA-N trimethoxyalumane Chemical compound [Al+3].[O-]C.[O-]C.[O-]C UAEJRRZPRZCUBE-UHFFFAOYSA-N 0.000 abstract 1
- 238000005406 washing Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/02—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains containing only carbon and hydrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/06—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms
- C07C403/12—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms by esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/14—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by doubly-bound oxygen atoms
- C07C403/16—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by doubly-bound oxygen atoms not being part of —CHO groups
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
- C07C45/676—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton by elimination of carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
- C11B9/0034—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing six carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US50252655A | 1955-04-19 | 1955-04-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB799797A true GB799797A (en) | 1958-08-13 |
Family
ID=23998229
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB11631/56A Expired GB799797A (en) | 1955-04-19 | 1956-04-17 | An improved process for the manufacture of unsaturated ketones |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE547084A (enrdf_load_html_response) |
| DE (1) | DE1053498B (enrdf_load_html_response) |
| FR (1) | FR1205812A (enrdf_load_html_response) |
| GB (1) | GB799797A (enrdf_load_html_response) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2928944A1 (de) * | 1979-07-18 | 1981-02-12 | Basf Ag | Verbessertes verfahren zur herstellung von hoeheren ungesaettigten ketonen |
| DE19647117A1 (de) * | 1996-11-14 | 1998-05-28 | Basf Ag | Verfahren zur Herstellung gamma,delta-ungesättigten Ketonen durch Caroll-Reaktion in cyclischen Carbonaten oder gamma-Lactonen als Lösungsmittel |
| DE10123066A1 (de) | 2001-05-11 | 2002-11-14 | Basf Ag | Verfahren zur Herstellung von höheren alpha,beta-ungesättigten Alkoholen |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2638484A (en) * | 1951-06-05 | 1953-05-12 | Hoffmann La Roche | Preparation of an octenone |
| FR1079408A (fr) * | 1952-06-10 | 1954-11-30 | Hoffmann La Roche | Procédé pour la préparation de cétones non saturées |
| US2662920A (en) * | 1952-06-10 | 1953-12-15 | Hoffmann La Roche | Process for preparing 2, 3-dimethylheptene-2-one-6 |
-
1956
- 1956-04-16 DE DEH26778A patent/DE1053498B/de active Pending
- 1956-04-17 BE BE547084D patent/BE547084A/xx unknown
- 1956-04-17 GB GB11631/56A patent/GB799797A/en not_active Expired
- 1956-04-18 FR FR1205812D patent/FR1205812A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR1205812A (fr) | 1960-02-04 |
| DE1053498B (de) | 1959-03-26 |
| BE547084A (enrdf_load_html_response) | 1956-10-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SAREL et al. | Organic carbonates. IV. 1a, b, c factors affecting formation of homologous cyclic carbonates | |
| US2824121A (en) | Process for preparation of oxy alkylidene compounds | |
| US2000252A (en) | Production of acetals | |
| ES377282A1 (es) | Procedimiento para la preparacion de esteres de ciloalquno-na. | |
| US2839579A (en) | Process for the production of ketones | |
| GB799797A (en) | An improved process for the manufacture of unsaturated ketones | |
| US2763665A (en) | Process for the manufacture of levulinic acid esters | |
| US3227736A (en) | Production of alpha-fluorocarboxylic acids and esters | |
| GB789411A (en) | A process for the manufacture of unsaturated ketones | |
| US2905690A (en) | Vinylation of oxazolidinones | |
| US2500005A (en) | Production of esters of unsaturated lower fatty acids | |
| GB923341A (en) | Process for the manufacture of alkyl esters of ªâ-alkoxy-carboxylic acids | |
| US2453677A (en) | Alkamine esters of pyrrole-3, 4-dicarboxylic acids | |
| US2673212A (en) | Process for preparing beta-methyl glutaconic acid esters from alkyl isodehydroacetates | |
| US2433645A (en) | Plasticizers | |
| US2719855A (en) | Steroid alkali-metal enolates | |
| DE974764C (de) | Verfahren zur Herstellung von monomeren Organosiliciumverbindungen | |
| US2348159A (en) | Production of acyclic condensation products of acetylene | |
| US1741877A (en) | New process of preparing phenyl-oxalyl acetic-acid alkyl esters | |
| GB742949A (en) | Improvements in and relating to the condensation of di-alkyl succinates | |
| GB733448A (en) | Steroid alkali-metal enolates | |
| GB1103415A (en) | Process for the manufacture of acetoacetic acid methyl ester and acetoacetic acid ethyl ester | |
| GB733884A (en) | Unsaturated keto-esters and the manufacture thereof | |
| US2826603A (en) | Process for preparing 3, 3 dichloro-2-methallyl substituted malonates | |
| US2617821A (en) | Method for preparing formic esters |