CA1077959A - Pyrolysis of limonene-1,2-dialkanoates to give perillyl alkanoates - Google Patents
Pyrolysis of limonene-1,2-dialkanoates to give perillyl alkanoatesInfo
- Publication number
- CA1077959A CA1077959A CA223,385A CA223385A CA1077959A CA 1077959 A CA1077959 A CA 1077959A CA 223385 A CA223385 A CA 223385A CA 1077959 A CA1077959 A CA 1077959A
- Authority
- CA
- Canada
- Prior art keywords
- pyrolysis
- perillyl
- limonene
- carried out
- process according
- 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
- 238000000197 pyrolysis Methods 0.000 title claims abstract description 28
- 238000000034 method Methods 0.000 claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- 239000007791 liquid phase Substances 0.000 claims abstract description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 230000014759 maintenance of location Effects 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000012808 vapor phase Substances 0.000 claims description 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 abstract description 27
- 150000002148 esters Chemical class 0.000 abstract description 19
- NDTYTMIUWGWIMO-UHFFFAOYSA-N perillyl alcohol Chemical compound CC(=C)C1CCC(CO)=CC1 NDTYTMIUWGWIMO-UHFFFAOYSA-N 0.000 abstract description 18
- 235000001510 limonene Nutrition 0.000 abstract description 14
- 229940087305 limonene Drugs 0.000 abstract description 14
- 239000000203 mixture Substances 0.000 abstract description 10
- 229930007631 (-)-perillyl alcohol Natural products 0.000 abstract description 9
- 235000005693 perillyl alcohol Nutrition 0.000 abstract description 9
- RUMOYJJNUMEFDD-UHFFFAOYSA-N perillyl aldehyde Chemical compound CC(=C)C1CCC(C=O)=CC1 RUMOYJJNUMEFDD-UHFFFAOYSA-N 0.000 abstract description 8
- 230000015572 biosynthetic process Effects 0.000 abstract description 6
- 238000006243 chemical reaction Methods 0.000 abstract description 5
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 239000012071 phase Substances 0.000 abstract description 4
- 239000007858 starting material Substances 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 abstract 1
- 239000000047 product Substances 0.000 description 11
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 7
- WTXBCFKGCNWPLS-UHFFFAOYSA-N (4-prop-1-en-2-yl-1-cyclohexenyl)methyl acetate Chemical compound CC(=O)OCC1=CCC(C(C)=C)CC1 WTXBCFKGCNWPLS-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- RXBQNMWIQKOSCS-UHFFFAOYSA-N (7,7-dimethyl-4-bicyclo[3.1.1]hept-3-enyl)methanol Chemical compound C1C2C(C)(C)C1CC=C2CO RXBQNMWIQKOSCS-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- BAVONGHXFVOKBV-UHFFFAOYSA-N Carveol Chemical compound CC(=C)C1CC=C(C)C(O)C1 BAVONGHXFVOKBV-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 150000005690 diesters Chemical class 0.000 description 3
- 238000004508 fractional distillation Methods 0.000 description 3
- 150000004965 peroxy acids Chemical class 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 230000000717 retained effect Effects 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- BAVONGHXFVOKBV-ZJUUUORDSA-N (-)-trans-carveol Natural products CC(=C)[C@@H]1CC=C(C)[C@@H](O)C1 BAVONGHXFVOKBV-ZJUUUORDSA-N 0.000 description 2
- YTHRBOFHFYZBRJ-UHFFFAOYSA-N (2-methyl-5-prop-1-en-2-yl-1-cyclohex-2-enyl) acetate Chemical compound CC(=O)OC1CC(C(C)=C)CC=C1C YTHRBOFHFYZBRJ-UHFFFAOYSA-N 0.000 description 2
- RXBQNMWIQKOSCS-RKDXNWHRSA-N Myrtenol Natural products C1[C@H]2C(C)(C)[C@@H]1CC=C2CO RXBQNMWIQKOSCS-RKDXNWHRSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229930007646 carveol Natural products 0.000 description 2
- -1 carveol ester Chemical class 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- YTHRBOFHFYZBRJ-RYUDHWBXSA-N Carvyl acetate Natural products CC(=O)O[C@H]1C[C@@H](C(C)=C)CC=C1C YTHRBOFHFYZBRJ-RYUDHWBXSA-N 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- CCEFMUBVSUDRLG-XNWIYYODSA-N Limonene-1,2-epoxide Chemical compound C1[C@H](C(=C)C)CCC2(C)OC21 CCEFMUBVSUDRLG-XNWIYYODSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 208000036366 Sensation of pressure Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- CVSVTCORWBXHQV-UHFFFAOYSA-N creatine Chemical compound NC(=[NH2+])N(C)CC([O-])=O CVSVTCORWBXHQV-UHFFFAOYSA-N 0.000 description 1
- 230000020176 deacylation Effects 0.000 description 1
- 238000005947 deacylation reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical group CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
- 229930007453 limonene-1,2-epoxide Natural products 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (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 |
|---|---|---|---|
| GB14367/74A GB1508602A (en) | 1974-04-01 | 1974-04-01 | Production of esters of perillyl alcohol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1077959A true CA1077959A (en) | 1980-05-20 |
Family
ID=10039942
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA223,385A Expired CA1077959A (en) | 1974-04-01 | 1975-03-25 | Pyrolysis of limonene-1,2-dialkanoates to give perillyl alkanoates |
Country Status (11)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5110832A (en) * | 1990-10-09 | 1992-05-05 | Doyle E. Chastain | Using perillyl alcohol to kill bacteria and yeasts |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5476550A (en) * | 1977-11-24 | 1979-06-19 | Taiyo Koryo Kk | Manufacture of perilla esters |
| FR2459214A1 (fr) * | 1979-06-19 | 1981-01-09 | Synarome H Fraysse Et Cie | Dihydroxy-7,8 paramenthene-1 et ses esters et procede de preparation |
| EP2393488B1 (en) | 2009-02-06 | 2019-06-19 | University Of Southern California | Therapeutic compositions comprising monoterpenes |
| EP3769754A1 (en) | 2010-03-03 | 2021-01-27 | Neonc Technologies, Inc. | Pharmaceutical compositions comprising monoterpenes |
| US7851660B1 (en) | 2010-04-19 | 2010-12-14 | Millennium Specialty Chemicals, Inc. | Process for making perillyl alcohol |
| US7884252B1 (en) | 2010-04-19 | 2011-02-08 | Lyondellbasell Flavors & Fragrances, Llc | Process for making trans-isocarveol |
| US20160038600A1 (en) | 2012-08-03 | 2016-02-11 | Neonc Technologies Inc. | Pharmaceutical compositions comprising poh derivatives |
| ES2610810T3 (es) | 2010-08-27 | 2017-05-03 | Neonc Technologies Inc. | Composiciones farmacéuticas que comprenden carbamatos de alcohol perilílico |
| EP4389765A3 (en) | 2018-02-08 | 2024-08-21 | University of Southern California | Methods of permeabilizing the blood brain barrier |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1183849A (fr) * | 1957-10-03 | 1959-07-15 | Centre Nat Rech Scient | Procédé de coupure de divers époxydes et notamment des époxydes du nopinène et du limonène |
-
1974
- 1974-04-01 GB GB14367/74A patent/GB1508602A/en not_active Expired
-
1975
- 1975-03-24 US US05/561,320 patent/US3957856A/en not_active Expired - Lifetime
- 1975-03-25 CA CA223,385A patent/CA1077959A/en not_active Expired
- 1975-03-27 DE DE19752513910 patent/DE2513910A1/de not_active Withdrawn
- 1975-03-27 NL NL7503698A patent/NL7503698A/xx not_active Application Discontinuation
- 1975-03-28 FR FR7509915A patent/FR2265715B1/fr not_active Expired
- 1975-03-28 BE BE154872A patent/BE827306A/xx unknown
- 1975-03-28 IT IT67813/75A patent/IT1030481B/it active
- 1975-03-31 ES ES436156A patent/ES436156A1/es not_active Expired
- 1975-04-01 JP JP50038625A patent/JPS50140419A/ja active Pending
- 1975-04-01 CH CH411475A patent/CH613438A5/xx not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5110832A (en) * | 1990-10-09 | 1992-05-05 | Doyle E. Chastain | Using perillyl alcohol to kill bacteria and yeasts |
Also Published As
| Publication number | Publication date |
|---|---|
| BE827306A (fr) | 1975-09-29 |
| DE2513910A1 (de) | 1975-10-09 |
| NL7503698A (nl) | 1975-10-03 |
| ES436156A1 (es) | 1977-02-16 |
| GB1508602A (en) | 1978-04-26 |
| FR2265715A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-10-24 |
| IT1030481B (it) | 1979-03-30 |
| JPS50140419A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-11-11 |
| FR2265715B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-04-13 |
| US3957856A (en) | 1976-05-18 |
| CH613438A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-09-28 |
| AU7968575A (en) | 1976-10-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |