GB666993A - Process for preparing alpha-ionones - Google Patents
Process for preparing alpha-iononesInfo
- Publication number
- GB666993A GB666993A GB31075/48A GB3107548A GB666993A GB 666993 A GB666993 A GB 666993A GB 31075/48 A GB31075/48 A GB 31075/48A GB 3107548 A GB3107548 A GB 3107548A GB 666993 A GB666993 A GB 666993A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ionones
- ionone
- pseudo
- methyl
- allyl
- 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
- 150000001381 alpha-ionone derivatives Chemical class 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- JXJIQCXXJGRKRJ-KOOBJXAQSA-N pseudoionone Chemical class CC(C)=CCC\C(C)=C\C=C\C(C)=O JXJIQCXXJGRKRJ-KOOBJXAQSA-N 0.000 abstract 3
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 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
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract 2
- SPHLZZZXIWUZNM-UHFFFAOYSA-N 7,11-dimethyldodeca-4,6,10-trien-3-one Chemical compound CCC(=O)C=CC=C(C)CCC=C(C)C SPHLZZZXIWUZNM-UHFFFAOYSA-N 0.000 abstract 1
- 229910015900 BF3 Inorganic materials 0.000 abstract 1
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 239000003518 caustics Substances 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 238000000638 solvent extraction 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
- C07C403/24—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 six-membered non-aromatic rings, e.g. beta-carotene
-
- 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
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
a -Ionones are prepared by treating the corresponding pseudo-ionones with at least 1, for example 1 to about 1.1, molecular equivalent of boron trifluoride. The latter may be passed into the pseudo-ionone, which may be of lowgrade and ketone content, at about -25 DEG to 30 DEG C., preferably at 0-5 DEG C., and in the presence of solvents such as benzene, toluene or carbon tetrachloride, until saturated, aqueous caustic alkali added, followed by solvent extraction and distillation. In examples, a -ionone is obtained from pseudo-ionone, a -methyl-ionones from pseudo-methyl-ionone obtained by condensing citrol and methyl ethyl ketone, and a -allyl-ionones from pseudo-allyl-ionone.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US277981XA | 1948-02-05 | 1948-02-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB666993A true GB666993A (en) | 1952-02-20 |
Family
ID=21839845
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB31075/48A Expired GB666993A (en) | 1948-02-05 | 1948-11-30 | Process for preparing alpha-ionones |
Country Status (5)
| Country | Link |
|---|---|
| CH (1) | CH277981A (en) |
| DE (1) | DE812313C (en) |
| FR (1) | FR975344A (en) |
| GB (1) | GB666993A (en) |
| NL (1) | NL69166C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2550790A1 (en) * | 1983-07-28 | 1985-02-22 | Inst Khim Akademii Nauk | PROCESS FOR THE PREPARATION OF 4-METHYLIONONE |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE931351C (en) * | 1948-05-04 | 1955-08-08 | Givaudan & Cie Sa | Process for the production of isomeric 6-methyl-ª ‡ -ionons (ª ‡ -ions) by ring closure of 3-methyl pseudoionons |
| DE1028992B (en) * | 1955-09-06 | 1958-04-30 | Hoffmann La Roche | Process for the production of unsaturated ketones |
| DE1045393B (en) * | 1956-05-04 | 1958-12-04 | Dragoco Gerberding Co Gmbh | Process for the preparation of derivatives of the 1,1-dimethyloctahydronaphthalene series |
| DE1109677B (en) * | 1958-08-01 | 1961-06-29 | Hoffmann La Roche | Process for the preparation of unsaturated ketones of the ionone type |
| DE1104504B (en) * | 1958-12-17 | 1961-04-13 | Hoffmann La Roche | Process for the preparation of unsaturated cyclic ketones |
| DE1112736B (en) * | 1959-01-16 | 1961-08-17 | Hoffmann La Roche | Process for the production of alicyclic ketones with valuable fragrance properties |
| DE1109679B (en) * | 1959-03-20 | 1961-06-29 | Hoffmann La Roche | Process for the preparation of unsaturated cyclic ketones |
| DE1137008B (en) * | 1961-03-11 | 1962-09-27 | Basf Ag | Process for the preparation of ionone compounds |
-
0
- NL NL69166D patent/NL69166C/xx active
-
1948
- 1948-09-28 CH CH277981D patent/CH277981A/en unknown
- 1948-11-22 FR FR975344D patent/FR975344A/en not_active Expired
- 1948-11-30 GB GB31075/48A patent/GB666993A/en not_active Expired
-
1949
- 1949-01-21 DE DEP32125D patent/DE812313C/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2550790A1 (en) * | 1983-07-28 | 1985-02-22 | Inst Khim Akademii Nauk | PROCESS FOR THE PREPARATION OF 4-METHYLIONONE |
Also Published As
| Publication number | Publication date |
|---|---|
| NL69166C (en) | |
| DE812313C (en) | 1951-08-27 |
| FR975344A (en) | 1951-03-05 |
| CH277981A (en) | 1951-09-30 |
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