GB861201A - Process for manufacturing terpeneless essential oils - Google Patents
Process for manufacturing terpeneless essential oilsInfo
- Publication number
- GB861201A GB861201A GB12858/59A GB1285859A GB861201A GB 861201 A GB861201 A GB 861201A GB 12858/59 A GB12858/59 A GB 12858/59A GB 1285859 A GB1285859 A GB 1285859A GB 861201 A GB861201 A GB 861201A
- Authority
- GB
- United Kingdom
- Prior art keywords
- oils
- terpenes
- oil
- polar solvent
- constituents
- 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
- 238000000034 method Methods 0.000 title abstract 5
- 239000000341 volatile oil Substances 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000003921 oil Substances 0.000 abstract 20
- 235000019198 oils Nutrition 0.000 abstract 20
- 150000003505 terpenes Chemical class 0.000 abstract 16
- 235000007586 terpenes Nutrition 0.000 abstract 16
- XMGQYMWWDOXHJM-JTQLQIEISA-N (+)-α-limonene Chemical compound CC(=C)[C@@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-JTQLQIEISA-N 0.000 abstract 8
- 230000002745 absorbent Effects 0.000 abstract 8
- 239000002250 absorbent Substances 0.000 abstract 8
- 239000000470 constituent Substances 0.000 abstract 8
- 239000002798 polar solvent Substances 0.000 abstract 8
- UWKAYLJWKGQEPM-UHFFFAOYSA-N 3,7-dimethylocta-1,6-dien-3-yl acetate Chemical compound CC(C)=CCCC(C)(C=C)OC(C)=O UWKAYLJWKGQEPM-UHFFFAOYSA-N 0.000 abstract 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 4
- MOYAFQVGZZPNRA-UHFFFAOYSA-N Terpinolene Chemical compound CC(C)=C1CCC(C)=CC1 MOYAFQVGZZPNRA-UHFFFAOYSA-N 0.000 abstract 4
- UAHWPYUMFXYFJY-UHFFFAOYSA-N beta-myrcene Chemical compound CC(C)=CCCC(=C)C=C UAHWPYUMFXYFJY-UHFFFAOYSA-N 0.000 abstract 4
- 229920001971 elastomer Polymers 0.000 abstract 4
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 abstract 4
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 abstract 4
- 150000007823 ocimene derivatives Chemical class 0.000 abstract 4
- 239000005060 rubber Substances 0.000 abstract 4
- XJPBRODHZKDRCB-UHFFFAOYSA-N trans-alpha-ocimene Natural products CC(=C)CCC=C(C)C=C XJPBRODHZKDRCB-UHFFFAOYSA-N 0.000 abstract 4
- GRWFGVWFFZKLTI-UHFFFAOYSA-N α-pinene Chemical compound CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 abstract 4
- NPNUFJAVOOONJE-ZIAGYGMSSA-N β-(E)-Caryophyllene Chemical compound C1CC(C)=CCCC(=C)[C@H]2CC(C)(C)[C@@H]21 NPNUFJAVOOONJE-ZIAGYGMSSA-N 0.000 abstract 4
- USDOQCCMRDNVAH-KKUMJFAQSA-N β-cadinene Chemical compound C1C=C(C)C[C@H]2[C@H](C(C)C)CC=C(C)[C@@H]21 USDOQCCMRDNVAH-KKUMJFAQSA-N 0.000 abstract 4
- YKFLAYDHMOASIY-UHFFFAOYSA-N γ-terpinene Chemical compound CC(C)C1=CCC(C)=CC1 YKFLAYDHMOASIY-UHFFFAOYSA-N 0.000 abstract 4
- 239000000463 material Substances 0.000 abstract 3
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 abstract 2
- CXENHBSYCFFKJS-VDQVFBMKSA-N (E,E)-alpha-farnesene Chemical compound CC(C)=CCC\C(C)=C\C\C=C(/C)C=C CXENHBSYCFFKJS-VDQVFBMKSA-N 0.000 abstract 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 abstract 2
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 abstract 2
- XBGUIVFBMBVUEG-UHFFFAOYSA-N 1-methyl-4-(1,5-dimethyl-4-hexenylidene)-1-cyclohexene Chemical compound CC(C)=CCCC(C)=C1CCC(C)=CC1 XBGUIVFBMBVUEG-UHFFFAOYSA-N 0.000 abstract 2
- 239000001169 1-methyl-4-propan-2-ylcyclohexa-1,4-diene Substances 0.000 abstract 2
- GRWFGVWFFZKLTI-IUCAKERBSA-N 1S,5S-(-)-alpha-Pinene Natural products CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 abstract 2
- 235000008733 Citrus aurantifolia Nutrition 0.000 abstract 2
- 235000005979 Citrus limon Nutrition 0.000 abstract 2
- 235000019499 Citrus oil Nutrition 0.000 abstract 2
- 244000131522 Citrus pyriformis Species 0.000 abstract 2
- 241001672694 Citrus reticulata Species 0.000 abstract 2
- 240000000560 Citrus x paradisi Species 0.000 abstract 2
- 241000208152 Geranium Species 0.000 abstract 2
- 244000043261 Hevea brasiliensis Species 0.000 abstract 2
- 244000178870 Lavandula angustifolia Species 0.000 abstract 2
- 235000010663 Lavandula angustifolia Nutrition 0.000 abstract 2
- 244000179970 Monarda didyma Species 0.000 abstract 2
- 235000010672 Monarda didyma Nutrition 0.000 abstract 2
- 240000008474 Pimenta dioica Species 0.000 abstract 2
- 235000006990 Pimenta dioica Nutrition 0.000 abstract 2
- 239000004698 Polyethylene Substances 0.000 abstract 2
- 239000004793 Polystyrene Substances 0.000 abstract 2
- 229920001328 Polyvinylidene chloride Polymers 0.000 abstract 2
- 235000011941 Tilia x europaea Nutrition 0.000 abstract 2
- QMAYBMKBYCGXDH-UHFFFAOYSA-N alpha-amorphene Natural products C1CC(C)=CC2C(C(C)C)CC=C(C)C21 QMAYBMKBYCGXDH-UHFFFAOYSA-N 0.000 abstract 2
- YHBUQBJHSRGZNF-HNNXBMFYSA-N alpha-bisabolene Natural products CC(C)=CCC=C(C)[C@@H]1CCC(C)=CC1 YHBUQBJHSRGZNF-HNNXBMFYSA-N 0.000 abstract 2
- VYBREYKSZAROCT-UHFFFAOYSA-N alpha-myrcene Natural products CC(=C)CCCC(=C)C=C VYBREYKSZAROCT-UHFFFAOYSA-N 0.000 abstract 2
- MVNCAPSFBDBCGF-UHFFFAOYSA-N alpha-pinene Natural products CC1=CCC23C1CC2C3(C)C MVNCAPSFBDBCGF-UHFFFAOYSA-N 0.000 abstract 2
- KQAZVFVOEIRWHN-UHFFFAOYSA-N alpha-thujene Natural products CC1=CCC2(C(C)C)C1C2 KQAZVFVOEIRWHN-UHFFFAOYSA-N 0.000 abstract 2
- 150000008378 aryl ethers Chemical class 0.000 abstract 2
- 235000021028 berry Nutrition 0.000 abstract 2
- NPNUFJAVOOONJE-UHFFFAOYSA-N beta-cariophyllene Natural products C1CC(C)=CCCC(=C)C2CC(C)(C)C21 NPNUFJAVOOONJE-UHFFFAOYSA-N 0.000 abstract 2
- 229930003493 bisabolene Natural products 0.000 abstract 2
- NPNUFJAVOOONJE-UONOGXRCSA-N caryophyllene Natural products C1CC(C)=CCCC(=C)[C@@H]2CC(C)(C)[C@@H]21 NPNUFJAVOOONJE-UONOGXRCSA-N 0.000 abstract 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 abstract 2
- 239000010500 citrus oil Substances 0.000 abstract 2
- 239000010634 clove oil Substances 0.000 abstract 2
- 239000003085 diluting agent Substances 0.000 abstract 2
- 238000004821 distillation Methods 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- 150000002430 hydrocarbons Chemical class 0.000 abstract 2
- 150000002576 ketones Chemical class 0.000 abstract 2
- 239000001102 lavandula vera Substances 0.000 abstract 2
- 235000018219 lavender Nutrition 0.000 abstract 2
- 239000004571 lime Substances 0.000 abstract 2
- 229930007744 linalool Natural products 0.000 abstract 2
- 229920003052 natural elastomer Polymers 0.000 abstract 2
- 229920001194 natural rubber Polymers 0.000 abstract 2
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 abstract 2
- 239000002245 particle Substances 0.000 abstract 2
- 150000007875 phellandrene derivatives Chemical class 0.000 abstract 2
- 229920003023 plastic Polymers 0.000 abstract 2
- 239000004033 plastic Substances 0.000 abstract 2
- 229920001084 poly(chloroprene) Polymers 0.000 abstract 2
- 229920001281 polyalkylene Polymers 0.000 abstract 2
- 229920000728 polyester Polymers 0.000 abstract 2
- -1 polyethylene Polymers 0.000 abstract 2
- 229920000573 polyethylene Polymers 0.000 abstract 2
- 229920002223 polystyrene Polymers 0.000 abstract 2
- 229920000915 polyvinyl chloride Polymers 0.000 abstract 2
- 239000004800 polyvinyl chloride Substances 0.000 abstract 2
- 239000005033 polyvinylidene chloride Substances 0.000 abstract 2
- 238000000926 separation method Methods 0.000 abstract 2
- USDOQCCMRDNVAH-UHFFFAOYSA-N sigma-cadinene Natural products C1C=C(C)CC2C(C(C)C)CC=C(C)C21 USDOQCCMRDNVAH-UHFFFAOYSA-N 0.000 abstract 2
- 229920002379 silicone rubber Polymers 0.000 abstract 2
- 239000007787 solid Substances 0.000 abstract 2
- 238000000638 solvent extraction Methods 0.000 abstract 2
- 150000007873 thujene derivatives Chemical class 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
Classifications
-
- 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
- C11B9/02—Recovery or refining of essential oils from raw materials
- C11B9/022—Refining
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Detergent Compositions (AREA)
- Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)
Abstract
Terpenes are removed from essential oils by contacting the oils with a solid absorbent material in the form of particles or of pieces of porous, perforated or spongy structure having intercommunicating voids or passageways and which has a greater affinity for the terpenes than for the other odoriferous constituents of the oil. The absorbents used are non-polar, and preferably polymeric. Examples are rubbers, e.g. processed natural rubber, "Buna" S ("Buna" is a Registered Trade Mark), neoprene and silicone rubbers, and plastics, e.g. polyvinyl chloride, polyvinylidene chloride, polyalkylenes such as polyethylene, polystyrene and polyesters. They are preferably ground to a size of 0.001-0.1 inches or used in the form of a sponge. The oil may be diluted with a polar solvent, e.g. a C1-C6 aliphatic alcohol which may be mixed with a C1-C6 ketone or ether, chlorinated hydrocarbon, aromatic ether or lower ester. Up to 5% of water may be added to increase the polarity of the diluent. The absorbent is preferably wetted with a polar solvent and any air or other gas displaced from its surface. A fractional separation of the oil constituents may be made by passing the diluted oil through a column of absorbent and passing the effluent through a continuously recording refractometer (or an ultra-violet or infra-red spectrometer). Any absorbed oxygenated constituents of the oil may be eluted with a polar solvent and the terpenes may subsequently be eluted with a less polar solvent. Oils of high terpene content may be pretreated to reduce the terpene content by a conventional process such as distillation or solvent extraction. Oils mentioned are citrus oils (lemon, grapefruit, orange, lime and mandarin) petitgrain, bergamot, lavender, pimenta berry, leaf stem and bud clove oils, bay leaf, and geranium. Specified terpenes are the pinenes, myrcene, dipentene, ocimene, terpinolene, d-limonene, gamma-terpinene, phellandrene, thujene, sesquicitronellene, bisabolene, beta-caryophyllene and cadinene. In an example, gum rubber is used to separate South American oil of petitgrain into four main fractions linalool, linalool acetate, terpenes and other hydrocarbons, and ocimene. The process may also be used to segregate the various oxygenated constituents of the oils and also to segregate various terpenes, e.g. d-limonene and alpha-pinene from para-cymene.ALSO:Terpenes are removed from essential oils by contacting the oils with a solid absorbent material, in the form of particles or of pieces of porous, perforated or spongy structure having intercommunicating voids or passageways, and which material has a greater affinity for the terpenes than for the other odoriferous constituents of the oil. The absorbents used are non-polar, and preferably polymeric. Examples are rubbers, e.g. processed natural rubber, "Buna" S ("Buna" is a Registered Trade Mark), neoprene or silicone rubbers, and plastics, e.g. polyvinyl chloride, polyvinylidene chloride, polyalkylenes such as polyethylene or polystyrene, and polyesters. They are preferably ground to a size of 0.001-0.1 inches or used in the form of a p sponge. The oil may be diluted with a polar solvent, e.g. a C1-C6 aliphatic alcohol, which may be mixed with a C1-C6 ketone or ether, chlorinated hydrocarbon, aromatic ether or lower ester. Up to 5% of water may be added to increase the polarity of the diluent. The absorbent is preferably wetted with a polar solvent and any air or other gas displaced from its surface. A fractional separation of the oil constituents may be made by passing the diluted oil through a column of absorbent and passing the effluent through a continuously recording refractometer (or an ultraviolet or infra-red spectrometer). Any absorbed oxygenated constituents of the oil may be eluted with a polar solvent and the terpenes may subsequently be eluted with a less polar solvent. Oils of high terpene content may be pretreated to reduce the terpene content by a conventional process such as distillation or solvent extraction. Oils mentioned are citrus oils (lemon, grapefruit, orange, lime and mandarin), petitgrain, bergamot, lavender, pimenta berry, leaf, stem and bud clove oils, bay leaf, and geranium. Specified terpenes are the pinenes, myrcene, dipentene, ocimene, terpinolene, d-limonene, gammaterpinene, phellandrene, thujene, sesquicitronellene, bisabolene, beta-caryophyllene and cadinene. In an example, gum rubber is used to separate South American oil of petitgrain into four main fractions comprising respectively linalool, linalool acetate, terpenes and other hydrocarbons, and ocimene. The process may also be used to segregate the various oxygenated constituents of the oils and also to segregate various terpenes, e.g. d-limonene and alphapinene from para-cymene.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US861201XA | 1958-05-14 | 1958-05-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB861201A true GB861201A (en) | 1961-02-15 |
Family
ID=22196401
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB12858/59A Expired GB861201A (en) | 1958-05-14 | 1959-04-15 | Process for manufacturing terpeneless essential oils |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB861201A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0427505A3 (en) * | 1989-11-07 | 1991-06-12 | Warner-Lambert Company | Chewing gum composition and its production |
| EP0423873A3 (en) * | 1989-10-19 | 1991-12-27 | The Procter & Gamble Company | Process for making improved citrus aqueous essence |
| CN103792219A (en) * | 2014-02-27 | 2014-05-14 | 厦门大学 | Red pulp honey pomelo spectrum identification method |
| CN107586611A (en) * | 2017-10-10 | 2018-01-16 | 广东长利香精香料有限公司 | A kind of grapefruit green tea essential oil |
| CN115418272A (en) * | 2022-08-29 | 2022-12-02 | 贵州省长顺黔南山绿色食品有限公司 | Preparation method of terpene-removed ginger essential oil |
-
1959
- 1959-04-15 GB GB12858/59A patent/GB861201A/en not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0423873A3 (en) * | 1989-10-19 | 1991-12-27 | The Procter & Gamble Company | Process for making improved citrus aqueous essence |
| EP0427505A3 (en) * | 1989-11-07 | 1991-06-12 | Warner-Lambert Company | Chewing gum composition and its production |
| CN103792219A (en) * | 2014-02-27 | 2014-05-14 | 厦门大学 | Red pulp honey pomelo spectrum identification method |
| CN107586611A (en) * | 2017-10-10 | 2018-01-16 | 广东长利香精香料有限公司 | A kind of grapefruit green tea essential oil |
| CN115418272A (en) * | 2022-08-29 | 2022-12-02 | 贵州省长顺黔南山绿色食品有限公司 | Preparation method of terpene-removed ginger essential oil |
| CN115418272B (en) * | 2022-08-29 | 2023-12-01 | 贵州省长顺黔南山绿色食品有限公司 | Preparation method of terpene-removed ginger essential oil |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Ben Salha et al. | A status review of terpenes and their separation methods | |
| Kirchner et al. | Preparation of terpeneless essential oils. A chromatographic process | |
| Şarer et al. | Monoterpenes in the essential oil of Origanum majorana | |
| Başer et al. | Composition of the essential oils of Zosima absinthifolia (Vent.) Link and Ferula elaeochytris Korovin from Turkey | |
| Bergquist et al. | Sterol composition and classification of the Porifera | |
| Moore | Volatile terpenes from Nasutitermes soldiers (Isoptera, Termitidae) | |
| Baser et al. | Composition of the essential oil of Origanum sipyleum of Turkish origin | |
| Erdtman et al. | The chemistry of the order Cupressales | |
| GB861201A (en) | Process for manufacturing terpeneless essential oils | |
| Yaghmai et al. | The essential oil of Dracocephalum kotschyi Boiss | |
| Chyau et al. | Characteristics of the steam-distilled oil and carbon dioxide extract of Zanthoxylum simulans fruits | |
| Nigam et al. | Column and gas chromatographic analysis of oil of wild ginger: identification and estimation of some new constituents | |
| Vernin | Volatile constituents of the essential oil of Santolina chamaecyparissus L. | |
| Kirimer et al. | Composition of the essential oil of Sideritis condensata Boiss. et Heldr. | |
| Mookherjee et al. | Characterization of the carbonyl compounds in reverted soybean oil1, 2, 3 | |
| Bağcı et al. | Study of the essential oil composition of two subspecies of Abies cilicica (Ant. et Kotschy) Carr. from Turkey | |
| Abousaber et al. | Composition of the essential oil of Thymus pubescens Boiss. et Kotschy ex Celak and Thymus fedtschenkoi Ronniger from Iran | |
| Pant et al. | Essential oil from Hyptis suaveolens Poit. | |
| Zito et al. | Essential oils of Chiliadenus lopadusanus (Asteraceae) | |
| US2975170A (en) | Process for manufacturing terpeneless essential oils | |
| Ikeura et al. | Identification of (E, E)-2, 4-undecadienal from coriander (Coriandrum sativum L.) as a highly effective deodorant compound against the offensive odor of porcine large intestine | |
| Marques et al. | Volatile oil of Psidium cattleianum Sabine from the Brazilian atlantic forest | |
| Demirci et al. | Composition of the essential oil of Marrubium bourgaei ssp. caricum PH Davis | |
| Pino et al. | Chemical composition of distilled grapefruit oil | |
| Barth et al. | Fractionation of polar organic constituents in environmental samples using the lipophilic dextran gels Sephadex LH-20 and Sephasorb HP ultrafine: application to a weathered Ekofisk crude oil |