JPS59117593A - 天然精油の精製方法 - Google Patents
天然精油の精製方法Info
- Publication number
- JPS59117593A JPS59117593A JP22623382A JP22623382A JPS59117593A JP S59117593 A JPS59117593 A JP S59117593A JP 22623382 A JP22623382 A JP 22623382A JP 22623382 A JP22623382 A JP 22623382A JP S59117593 A JPS59117593 A JP S59117593A
- Authority
- JP
- Japan
- Prior art keywords
- essential oil
- hydrocarbons
- terpene
- essential oils
- aroma
- 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.)
- Granted
Links
- 239000000341 volatile oil Substances 0.000 title claims description 65
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 69
- 229930195733 hydrocarbon Natural products 0.000 claims description 62
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
- -1 terpene hydrocarbons Chemical class 0.000 claims description 39
- 235000007586 terpenes Nutrition 0.000 claims description 38
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical class O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 239000000741 silica gel Substances 0.000 claims description 11
- 229910002027 silica gel Inorganic materials 0.000 claims description 11
- 239000002952 polymeric resin Substances 0.000 claims description 9
- 229920005989 resin Polymers 0.000 claims description 9
- 239000011347 resin Substances 0.000 claims description 9
- 229920003002 synthetic resin Polymers 0.000 claims description 9
- 150000003505 terpenes Chemical class 0.000 claims description 9
- 239000000243 solution Substances 0.000 description 29
- 150000002430 hydrocarbons Chemical class 0.000 description 26
- 239000000796 flavoring agent Substances 0.000 description 18
- 235000019634 flavors Nutrition 0.000 description 18
- 239000004215 Carbon black (E152) Substances 0.000 description 17
- 150000001875 compounds Chemical class 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- 239000004480 active ingredient Substances 0.000 description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 9
- 230000006866 deterioration Effects 0.000 description 9
- 239000001301 oxygen Substances 0.000 description 9
- 229910052760 oxygen Inorganic materials 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 239000000377 silicon dioxide Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 238000009835 boiling Methods 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- 238000003860 storage Methods 0.000 description 7
- 235000013399 edible fruits Nutrition 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000000605 extraction Methods 0.000 description 5
- 229930003658 monoterpene Natural products 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 235000005979 Citrus limon Nutrition 0.000 description 4
- 244000131522 Citrus pyriformis Species 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- 235000002577 monoterpenes Nutrition 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 238000001179 sorption measurement Methods 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000003292 glue Substances 0.000 description 3
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 3
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 3
- 229930004725 sesquiterpene Natural products 0.000 description 3
- 238000000638 solvent extraction Methods 0.000 description 3
- GRWFGVWFFZKLTI-IUCAKERBSA-N (-)-α-pinene Chemical compound CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 2
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- GXDHCNNESPLIKD-UHFFFAOYSA-N 2-methylhexane Chemical compound CCCCC(C)C GXDHCNNESPLIKD-UHFFFAOYSA-N 0.000 description 2
- PFEOZHBOMNWTJB-UHFFFAOYSA-N 3-methylpentane Chemical compound CCC(C)CC PFEOZHBOMNWTJB-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 244000141359 Malus pumila Species 0.000 description 2
- 230000004075 alteration Effects 0.000 description 2
- 235000021016 apples Nutrition 0.000 description 2
- UAHWPYUMFXYFJY-UHFFFAOYSA-N beta-myrcene Chemical compound CC(C)=CCCC(=C)C=C UAHWPYUMFXYFJY-UHFFFAOYSA-N 0.000 description 2
- MPMBRWOOISTHJV-UHFFFAOYSA-N but-1-enylbenzene Chemical compound CCC=CC1=CC=CC=C1 MPMBRWOOISTHJV-UHFFFAOYSA-N 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000000622 liquid--liquid extraction Methods 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000001256 steam distillation Methods 0.000 description 2
- YHQGMYUVUMAZJR-UHFFFAOYSA-N α-terpinene Chemical compound CC(C)C1=CC=C(C)CC1 YHQGMYUVUMAZJR-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- CHBNMKPHUSAEJE-KQLJZIGXSA-N 2,6,6-trimethyl-3-(2,6,6-trimethyl-3-bicyclo[3.1.1]hept-1-enyl)-3-[(3R)-2,6,6-trimethyl-3-bicyclo[3.1.1]hept-1-enyl]bicyclo[3.1.1]hept-1-ene Chemical compound C12=C([C@@H](CC(C1(C)C)C2)C1(C(=C2C(C(C1)C2)(C)C)C)C1C(=C2C(C(C1)C2)(C)C)C)C CHBNMKPHUSAEJE-KQLJZIGXSA-N 0.000 description 1
- ZPZDIFSPRVHGIF-UHFFFAOYSA-N 3-aminopropylsilicon Chemical compound NCCC[Si] ZPZDIFSPRVHGIF-UHFFFAOYSA-N 0.000 description 1
- LFPDKAGCYBUUGO-UHFFFAOYSA-N 3-cyanopropylsilicon Chemical compound [Si]CCCC#N LFPDKAGCYBUUGO-UHFFFAOYSA-N 0.000 description 1
- NVEQFIOZRFFVFW-UHFFFAOYSA-N 9-epi-beta-caryophyllene oxide Natural products C=C1CCC2OC2(C)CCC2C(C)(C)CC21 NVEQFIOZRFFVFW-UHFFFAOYSA-N 0.000 description 1
- 241000951471 Citrus junos Species 0.000 description 1
- 240000005109 Cryptomeria japonica Species 0.000 description 1
- 244000241257 Cucumis melo Species 0.000 description 1
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 description 1
- 240000000731 Fagus sylvatica Species 0.000 description 1
- 235000010099 Fagus sylvatica Nutrition 0.000 description 1
- 240000009088 Fragaria x ananassa Species 0.000 description 1
- 235000019501 Lemon oil Nutrition 0.000 description 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 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 240000008790 Musa x paradisiaca Species 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- CBSRFDQDBGGSEA-UHFFFAOYSA-N Selinene Natural products CC(=C1CCC2(C)CCCC(=C)C2(C)C1)C CBSRFDQDBGGSEA-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001343 alkyl silanes Chemical class 0.000 description 1
- FAMPSKZZVDUYOS-UHFFFAOYSA-N alpha-Caryophyllene Natural products CC1=CCC(C)(C)C=CCC(C)=CCC1 FAMPSKZZVDUYOS-UHFFFAOYSA-N 0.000 description 1
- VYBREYKSZAROCT-UHFFFAOYSA-N alpha-myrcene Natural products CC(=C)CCCC(=C)C=C VYBREYKSZAROCT-UHFFFAOYSA-N 0.000 description 1
- MVNCAPSFBDBCGF-UHFFFAOYSA-N alpha-pinene Natural products CC1=CCC23C1CC2C3(C)C MVNCAPSFBDBCGF-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000021015 bananas Nutrition 0.000 description 1
- NPNUFJAVOOONJE-UHFFFAOYSA-N beta-cariophyllene Natural products C1CC(C)=CCCC(=C)C2CC(C)(C)C21 NPNUFJAVOOONJE-UHFFFAOYSA-N 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- NPNUFJAVOOONJE-UONOGXRCSA-N caryophyllene Natural products C1CC(C)=CCCC(=C)[C@@H]2CC(C)(C)[C@@H]21 NPNUFJAVOOONJE-UONOGXRCSA-N 0.000 description 1
- 229940117948 caryophyllene Drugs 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000001279 citrus aurantifolia swingle expressed oil Substances 0.000 description 1
- 239000001926 citrus aurantium l. subsp. bergamia wright et arn. oil Substances 0.000 description 1
- 239000001524 citrus aurantium oil Substances 0.000 description 1
- 239000001071 citrus reticulata blanco var. mandarin Substances 0.000 description 1
- 229920006026 co-polymeric resin Polymers 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010651 grapefruit oil Substances 0.000 description 1
- 230000002706 hydrostatic effect Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 239000010501 lemon oil Substances 0.000 description 1
- 235000001510 limonene Nutrition 0.000 description 1
- 229940087305 limonene Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002773 monoterpene derivatives Chemical class 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- YTJSFYQNRXLOIC-UHFFFAOYSA-N octadecylsilane Chemical compound CCCCCCCCCCCCCCCCCC[SiH3] YTJSFYQNRXLOIC-UHFFFAOYSA-N 0.000 description 1
- FPLYNRPOIZEADP-UHFFFAOYSA-N octylsilane Chemical compound CCCCCCCC[SiH3] FPLYNRPOIZEADP-UHFFFAOYSA-N 0.000 description 1
- 239000007968 orange flavor Substances 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- GRWFGVWFFZKLTI-UHFFFAOYSA-N rac-alpha-Pinene Natural products CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 239000012261 resinous substance Substances 0.000 description 1
- VPQBJIRQUUEAFC-UHFFFAOYSA-N selinene Natural products C1CC=C(C)C2CC(C(C)C)CCC21C VPQBJIRQUUEAFC-UHFFFAOYSA-N 0.000 description 1
- 150000003598 selinene derivatives Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000021012 strawberries Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Landscapes
- Fats And Perfumes (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22623382A JPS59117593A (ja) | 1982-12-24 | 1982-12-24 | 天然精油の精製方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22623382A JPS59117593A (ja) | 1982-12-24 | 1982-12-24 | 天然精油の精製方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59117593A true JPS59117593A (ja) | 1984-07-06 |
| JPH0152439B2 JPH0152439B2 (enrdf_load_stackoverflow) | 1989-11-08 |
Family
ID=16841975
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22623382A Granted JPS59117593A (ja) | 1982-12-24 | 1982-12-24 | 天然精油の精製方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59117593A (enrdf_load_stackoverflow) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62283198A (ja) * | 1986-05-30 | 1987-12-09 | 長谷川香料株式会社 | プソラレン類を含有しない天然精油の製法 |
| JPH02180997A (ja) * | 1988-10-14 | 1990-07-13 | Skw Trostberg Ag | 精油からテルペン類を除去する方法 |
| FR2658836A1 (fr) * | 1990-02-28 | 1991-08-30 | Cobor | Procede de preparation d'une essence aromatique vegetale hydrosoluble de haute qualite organoleptique, stable dans le temps et son utilisation dans des boissons et compositions diverses. |
| JP2000245431A (ja) * | 1999-02-26 | 2000-09-12 | Takara Shuzo Co Ltd | 低アルコール飲料 |
| CN105066590A (zh) * | 2015-07-22 | 2015-11-18 | 大闽食品（漳州）有限公司 | 一种吸附柚子花鲜花头香及低温干燥柚子鲜花的方法 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2009231637A1 (en) | 2008-04-05 | 2009-10-08 | Synthes Gmbh | Expandable intervertebral implant |
-
1982
- 1982-12-24 JP JP22623382A patent/JPS59117593A/ja active Granted
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62283198A (ja) * | 1986-05-30 | 1987-12-09 | 長谷川香料株式会社 | プソラレン類を含有しない天然精油の製法 |
| JPH02180997A (ja) * | 1988-10-14 | 1990-07-13 | Skw Trostberg Ag | 精油からテルペン類を除去する方法 |
| FR2658836A1 (fr) * | 1990-02-28 | 1991-08-30 | Cobor | Procede de preparation d'une essence aromatique vegetale hydrosoluble de haute qualite organoleptique, stable dans le temps et son utilisation dans des boissons et compositions diverses. |
| JP2000245431A (ja) * | 1999-02-26 | 2000-09-12 | Takara Shuzo Co Ltd | 低アルコール飲料 |
| CN105066590A (zh) * | 2015-07-22 | 2015-11-18 | 大闽食品（漳州）有限公司 | 一种吸附柚子花鲜花头香及低温干燥柚子鲜花的方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0152439B2 (enrdf_load_stackoverflow) | 1989-11-08 |
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