GB1194710A - Improvements in or relating to Isomerization of d-3-Carene to d-4-Carene - Google Patents
Improvements in or relating to Isomerization of d-3-Carene to d-4-CareneInfo
- Publication number
- GB1194710A GB1194710A GB28759/67A GB2875967A GB1194710A GB 1194710 A GB1194710 A GB 1194710A GB 28759/67 A GB28759/67 A GB 28759/67A GB 2875967 A GB2875967 A GB 2875967A GB 1194710 A GB1194710 A GB 1194710A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carene
- trans
- sodium
- isoterpinolene
- isolimonene
- 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
- 238000006317 isomerization reaction Methods 0.000 title abstract 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 5
- 229910052708 sodium Inorganic materials 0.000 abstract 5
- 239000011734 sodium Substances 0.000 abstract 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 4
- 229910052700 potassium Inorganic materials 0.000 abstract 4
- 239000011591 potassium Substances 0.000 abstract 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 3
- 239000006227 byproduct Substances 0.000 abstract 3
- 239000003054 catalyst Substances 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- YHQGMYUVUMAZJR-UHFFFAOYSA-N α-terpinene Chemical compound CC(C)C1=CC=C(C)CC1 YHQGMYUVUMAZJR-UHFFFAOYSA-N 0.000 abstract 2
- NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 abstract 1
- NVIAKXGGJKBFJH-UHFFFAOYSA-N 3-(2-chloropropan-2-yl)-6-methylcyclohexene Chemical compound CC1CCC(C(C)(C)Cl)C=C1 NVIAKXGGJKBFJH-UHFFFAOYSA-N 0.000 abstract 1
- AJSJXSBFZDIRIS-UHFFFAOYSA-N 4-methyl-1-prop-1-en-2-ylcyclohexene Chemical compound CC1CCC(C(C)=C)=CC1 AJSJXSBFZDIRIS-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- WSTYNZDAOAEEKG-UHFFFAOYSA-N Mayol Natural products CC1=C(O)C(=O)C=C2C(CCC3(C4CC(C(CC4(CCC33C)C)=O)C)C)(C)C3=CC=C21 WSTYNZDAOAEEKG-UHFFFAOYSA-N 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 150000001398 aluminium Chemical class 0.000 abstract 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 239000000010 aprotic solvent Substances 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 238000000354 decomposition reaction Methods 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000012433 hydrogen halide Substances 0.000 abstract 1
- 229910000039 hydrogen halide Inorganic materials 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 229960004873 levomenthol Drugs 0.000 abstract 1
- 229910052759 nickel Inorganic materials 0.000 abstract 1
- 229910052763 palladium Inorganic materials 0.000 abstract 1
- 229910052697 platinum Inorganic materials 0.000 abstract 1
- 235000011118 potassium hydroxide Nutrition 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 229910052707 ruthenium Inorganic materials 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 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
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/02—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/16—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with a six-membered ring
- C07C13/20—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with a six-membered ring with a cyclohexene ring
- C07C13/21—Menthadienes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/02—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/16—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with a six-membered ring
- C07C13/20—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with a six-membered ring with a cyclohexene ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
- C07C5/03—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of non-aromatic carbon-to-carbon double bonds
- C07C5/05—Partial hydrogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
- C07C5/23—Rearrangement of carbon-to-carbon unsaturated bonds
- C07C5/25—Migration of carbon-to-carbon double bonds
- C07C5/2506—Catalytic processes
- C07C5/2556—Catalytic processes with metals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
- C07C5/23—Rearrangement of carbon-to-carbon unsaturated bonds
- C07C5/25—Migration of carbon-to-carbon double bonds
- C07C5/2506—Catalytic processes
- C07C5/2562—Catalytic processes with hydrides or organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
- C07C5/23—Rearrangement of carbon-to-carbon unsaturated bonds
- C07C5/25—Migration of carbon-to-carbon double bonds
- C07C5/2506—Catalytic processes
- C07C5/2562—Catalytic processes with hydrides or organic compounds
- C07C5/2575—Catalytic processes with hydrides or organic compounds containing metal-to-carbon bond; Metal hydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
- C07C5/27—Rearrangement of carbon atoms in the hydrocarbon skeleton
- C07C5/31—Rearrangement of carbon atoms in the hydrocarbon skeleton changing the number of rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- C07C2531/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
-
- 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)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US563370A US3407241A (en) | 1966-07-07 | 1966-07-07 | Isomerization of 3-carene to 4-carene and further conversion of 4-carene |
| US563383A US3407242A (en) | 1966-07-07 | 1966-07-07 | Isomerization of 3-carene to 4-carene and further conversion of the 4-carene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1194710A true GB1194710A (en) | 1970-06-10 |
Family
ID=27073270
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB28759/67A Expired GB1194710A (en) | 1966-07-07 | 1967-06-21 | Improvements in or relating to Isomerization of d-3-Carene to d-4-Carene |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS5231861B1 (enExample) |
| CH (2) | CH503671A (enExample) |
| DE (1) | DE1618521A1 (enExample) |
| GB (1) | GB1194710A (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56127533U (enExample) * | 1980-02-21 | 1981-09-28 | ||
| JPS6191813A (ja) * | 1984-10-11 | 1986-05-09 | シャープ株式会社 | 透明タツチパネル |
| JPS636645U (enExample) * | 1986-06-30 | 1988-01-18 |
-
1967
- 1967-06-21 GB GB28759/67A patent/GB1194710A/en not_active Expired
- 1967-06-30 DE DE19671618521 patent/DE1618521A1/de active Pending
- 1967-07-06 CH CH964667A patent/CH503671A/de not_active IP Right Cessation
- 1967-07-06 CH CH1740170A patent/CH525849A/de not_active IP Right Cessation
-
1970
- 1970-12-28 JP JP45120607A patent/JPS5231861B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CH503671A (de) | 1971-02-28 |
| JPS5231861B1 (enExample) | 1977-08-17 |
| DE1618521A1 (de) | 1972-06-08 |
| CH525849A (de) | 1972-07-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |