GB788301A - A process for the manufacture of 6, 10-dimethyl-undecanone-(2) - Google Patents
A process for the manufacture of 6, 10-dimethyl-undecanone-(2)Info
- Publication number
- GB788301A GB788301A GB4876/55A GB487655A GB788301A GB 788301 A GB788301 A GB 788301A GB 4876/55 A GB4876/55 A GB 4876/55A GB 487655 A GB487655 A GB 487655A GB 788301 A GB788301 A GB 788301A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- resulting
- undecanone
- dimethyl
- solution
- 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
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 4
- 229910052763 palladium Inorganic materials 0.000 abstract 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 3
- 239000003054 catalyst Substances 0.000 abstract 3
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 abstract 3
- 239000000243 solution Substances 0.000 abstract 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 abstract 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 abstract 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 235000011114 ammonium hydroxide Nutrition 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- HNZUNIKWNYHEJJ-UHFFFAOYSA-N geranyl acetone Natural products CC(C)=CCCC(C)=CCCC(C)=O HNZUNIKWNYHEJJ-UHFFFAOYSA-N 0.000 abstract 2
- HNZUNIKWNYHEJJ-FMIVXFBMSA-N geranyl acetone Chemical compound CC(C)=CCC\C(C)=C\CCC(C)=O HNZUNIKWNYHEJJ-FMIVXFBMSA-N 0.000 abstract 2
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 abstract 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 2
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 abstract 1
- 239000001371 (5E)-3,5-dimethylocta-1,5,7-trien-3-ol Substances 0.000 abstract 1
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 abstract 1
- NBWLKCHXMMMNLN-UHFFFAOYSA-N 2-methyldodecan-3-one Chemical compound CCCCCCCCCC(=O)C(C)C NBWLKCHXMMMNLN-UHFFFAOYSA-N 0.000 abstract 1
- ZANSWOBXLYAUHS-UHFFFAOYSA-N 3,7-dimethylocta-1,6-dien-3-yl 3-oxobutanoate Chemical compound CC(C)=CCCC(C)(C=C)OC(=O)CC(C)=O ZANSWOBXLYAUHS-UHFFFAOYSA-N 0.000 abstract 1
- LGVYUZVANMHKHV-UHFFFAOYSA-N 6,10-Dimethylundec-9-en-2-one Chemical compound CC(=O)CCCC(C)CCC=C(C)C LGVYUZVANMHKHV-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- 239000011260 aqueous acid Substances 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 229910000019 calcium carbonate Inorganic materials 0.000 abstract 1
- 239000001569 carbon dioxide Substances 0.000 abstract 1
- 229910002092 carbon dioxide Inorganic materials 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 abstract 1
- 229960001231 choline Drugs 0.000 abstract 1
- 230000000911 decarboxylating effect Effects 0.000 abstract 1
- ZJIQIJIQBTVTDY-SREVYHEPSA-N dehydrolinalool Chemical compound CC(=C)\C=C/CC(C)(O)C=C ZJIQIJIQBTVTDY-SREVYHEPSA-N 0.000 abstract 1
- 230000008030 elimination Effects 0.000 abstract 1
- 238000003379 elimination reaction Methods 0.000 abstract 1
- -1 for example Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 229930007744 linalool Natural products 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- SFDZETWZUCDYMD-UHFFFAOYSA-N monosodium acetylide Chemical compound [Na+].[C-]#C SFDZETWZUCDYMD-UHFFFAOYSA-N 0.000 abstract 1
- 229910052759 nickel Inorganic materials 0.000 abstract 1
- 150000002940 palladium Chemical class 0.000 abstract 1
- 239000003208 petroleum Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
- C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
- C07C29/42—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing triple carbon-to-carbon bonds, e.g. with metal-alkynes
-
- 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
- C07C45/62—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 hydrogenation of carbon-to-carbon double or triple bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/46—Preparation of carboxylic acid esters from ketenes or polyketenes
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12C—BEER; PREPARATION OF BEER BY FERMENTATION; PREPARATION OF MALT FOR MAKING BEER; PREPARATION OF HOPS FOR MAKING BEER
- C12C11/00—Fermentation processes for beer
- C12C11/02—Pitching yeast
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Mycology (AREA)
- Food Science & Technology (AREA)
- Microbiology (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
6 : 10 - Dimethyl - undecanone - 2 is prepared by the catalytic hydrogenation of geranylacetone or tetra-hydro pseudoionone. A nickel or palladium catalyst may be used. The starting materials may be prepared by reacting 6-methyl-hepten-5-one-2 or 6-methyl-heptanone-2 with an alkali metal derivative of acetylene in liquid ammonia solution, treating the product with a non-alkaline hydrolysing agent, for example, water, a dilute aqueous acid or a nonalkaline ammonium salt as such or in aqueous solution, partially hydrogenating the resulting acetylenic carbinol in the presence of a palladium or nickel catalyst which selectively catalyses reduction of a triple bond to a double bond, reacting the ethylenic carbinol so formed with diketene and decarboxylating the resulting linalyl or di-hydro-linalyl acetoacetate by heating with elimination of carbon dioxide. The reaction with diketene is preferably effected in the presence of a weakly-acid agent such as a mixture of pyridine or choline and acetic acid; a solvent may be present. In examples: (1) a toluene solution of 6-methyl-hepten-5-one-2 is added dropwise to a liquid ammonia solution of sodium acetylide and the product is then stripped of the ammonia and treated with aqueous sulphuric acid; the resulting dehydrolinalool is hydrogenated in petroleum ether solution using a lead-poisoned palladium calcium carbonate catalyst to form linalool which is treated in toluene solution with diketene in the presence of some pyridine and acetic acid; the resulting linalyl acetoacetate is decarboxylated at 140-165 DEG C. to yield geranyl acetone; the latter is then hydrogenated at 95-100 DEG C. under 500 lb. hydrogen pressure using the above mentioned palladium catalyst yielding the desired 6 : 10-dimethyl undecanone-2; (2) using the same operations, 6-methyl-heptanone-2 is converted to the desired dimethyl undecanone. Specifications 788,302 and 788,303 are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US788301XA | 1954-02-26 | 1954-02-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB788301A true GB788301A (en) | 1957-12-23 |
Family
ID=22146460
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4876/55A Expired GB788301A (en) | 1954-02-26 | 1955-02-18 | A process for the manufacture of 6, 10-dimethyl-undecanone-(2) |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB788301A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4292454A (en) | 1977-12-29 | 1981-09-29 | Scm Corporation | Coupling reaction involving a Grignard and allylic halide |
| WO1998007405A1 (en) * | 1996-08-19 | 1998-02-26 | The Procter & Gamble Company | Fragrance delivery systems |
| WO2004007413A1 (en) * | 2002-07-15 | 2004-01-22 | Basf Aktiengesellschaft | Method for the production of tetrahydrogeranylacetone |
| US7411098B2 (en) | 2003-12-15 | 2008-08-12 | Basf Se | Method for the production of tetrahydrogeranylacetone |
| US20120053353A1 (en) * | 2010-08-24 | 2012-03-01 | Dsm Ip Assets B.V. | Process for the manufacture of 3,7-dimethyl-1-octen-3-ol |
| WO2012025559A2 (en) | 2010-08-24 | 2012-03-01 | Dsm Ip Assets B.V. | Process for the manufacture of 3,7-dimethyl-1-octen-3-ol |
| WO2017098048A1 (en) | 2015-12-11 | 2017-06-15 | Dsm Ip Assets B.V. | Process for the manufacture of 6,10,14-trimethylpentadecan-2-one |
-
1955
- 1955-02-18 GB GB4876/55A patent/GB788301A/en not_active Expired
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4292454A (en) | 1977-12-29 | 1981-09-29 | Scm Corporation | Coupling reaction involving a Grignard and allylic halide |
| WO1998007405A1 (en) * | 1996-08-19 | 1998-02-26 | The Procter & Gamble Company | Fragrance delivery systems |
| WO2004007413A1 (en) * | 2002-07-15 | 2004-01-22 | Basf Aktiengesellschaft | Method for the production of tetrahydrogeranylacetone |
| US7345205B2 (en) | 2002-07-15 | 2008-03-18 | Basf Aktiengesellschaft | Method for the production of tetrahydrogeranylacetone |
| US7411098B2 (en) | 2003-12-15 | 2008-08-12 | Basf Se | Method for the production of tetrahydrogeranylacetone |
| US20120053353A1 (en) * | 2010-08-24 | 2012-03-01 | Dsm Ip Assets B.V. | Process for the manufacture of 3,7-dimethyl-1-octen-3-ol |
| WO2012025559A2 (en) | 2010-08-24 | 2012-03-01 | Dsm Ip Assets B.V. | Process for the manufacture of 3,7-dimethyl-1-octen-3-ol |
| US8546621B2 (en) * | 2010-08-24 | 2013-10-01 | Dsm Ip Assets B.V. | Process for the manufacture of 3,7-dimethyl-1-octen-3-ol |
| WO2017098048A1 (en) | 2015-12-11 | 2017-06-15 | Dsm Ip Assets B.V. | Process for the manufacture of 6,10,14-trimethylpentadecan-2-one |
| WO2017098049A1 (en) | 2015-12-11 | 2017-06-15 | Dsm Ip Assets B.V. | Process for the manufacture of 6,10,14-trimethylpentadecan-2-one |
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