CN1764622A - Process for producing 2-(l-menthoxy)ethanol compound - Google Patents
Process for producing 2-(l-menthoxy)ethanol compound Download PDFInfo
- Publication number
- CN1764622A CN1764622A CNA2004800078636A CN200480007863A CN1764622A CN 1764622 A CN1764622 A CN 1764622A CN A2004800078636 A CNA2004800078636 A CN A2004800078636A CN 200480007863 A CN200480007863 A CN 200480007863A CN 1764622 A CN1764622 A CN 1764622A
- Authority
- CN
- China
- Prior art keywords
- oxygen base
- menthol
- compound
- peppermint oxygen
- preparation
- 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
- -1 2-(l-menthoxy)ethanol compound Chemical class 0.000 title claims abstract description 39
- 238000000034 method Methods 0.000 title abstract description 13
- NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 claims abstract description 25
- 239000002841 Lewis acid Substances 0.000 claims abstract description 11
- 150000007517 lewis acids Chemical class 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 239000002585 base Substances 0.000 claims description 36
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 35
- 239000001301 oxygen Substances 0.000 claims description 35
- 229910052760 oxygen Inorganic materials 0.000 claims description 35
- 150000001875 compounds Chemical class 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 15
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 14
- 239000004593 Epoxy Substances 0.000 claims description 12
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 12
- 235000005074 zinc chloride Nutrition 0.000 claims description 7
- 239000011592 zinc chloride Substances 0.000 claims description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 claims description 6
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- 229910052742 iron Inorganic materials 0.000 claims description 3
- 229940102001 zinc bromide Drugs 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 abstract description 3
- 239000002537 cosmetic Substances 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- 235000013361 beverage Nutrition 0.000 abstract 1
- 235000019504 cigarettes Nutrition 0.000 abstract 1
- 235000013305 food Nutrition 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- 230000001835 salubrious effect Effects 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- 230000009466 transformation Effects 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229940063656 aluminum chloride Drugs 0.000 description 4
- 229940055858 aluminum chloride anhydrous Drugs 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 230000035807 sensation Effects 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000003205 fragrance Substances 0.000 description 3
- 239000011968 lewis acid catalyst Substances 0.000 description 3
- 229940041616 menthol Drugs 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 235000006679 Mentha X verticillata Nutrition 0.000 description 2
- 235000002899 Mentha suaveolens Nutrition 0.000 description 2
- 235000001636 Mentha x rotundifolia Nutrition 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 241000208125 Nicotiana Species 0.000 description 2
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 235000005911 diet Nutrition 0.000 description 2
- 230000037213 diet Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VTBLOVRGIHUQQZ-KXUCPTDWSA-N CC(C)[C@@H]1CC[C@@H](C)C[C@H]1[O] Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1[O] VTBLOVRGIHUQQZ-KXUCPTDWSA-N 0.000 description 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 235000016257 Mentha pulegium Nutrition 0.000 description 1
- 244000246386 Mentha pulegium Species 0.000 description 1
- 235000004357 Mentha x piperita Nutrition 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940112822 chewing gum Drugs 0.000 description 1
- 235000015218 chewing gum Nutrition 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 210000001508 eye Anatomy 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 235000001050 hortel pimenta Nutrition 0.000 description 1
- 229960003284 iron Drugs 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 210000000214 mouth Anatomy 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 210000003928 nasal cavity Anatomy 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 210000003800 pharynx Anatomy 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- XHFLOLLMZOTPSM-UHFFFAOYSA-M sodium;hydrogen carbonate;hydrate Chemical class [OH-].[Na+].OC(O)=O XHFLOLLMZOTPSM-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000000606 toothpaste Substances 0.000 description 1
- 229940034610 toothpaste Drugs 0.000 description 1
- 229960001939 zinc chloride Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/02—Preparation of ethers from oxiranes
- C07C41/03—Preparation of ethers from oxiranes by reaction of oxirane rings with hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/18—Ethers having an ether-oxygen atom bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C43/196—Ethers having an ether-oxygen atom bound to a carbon atom of a ring other than a six-membered aromatic ring containing hydroxy or O-metal 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
- C07C2601/14—The ring being saturated
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)
Abstract
Description
Catalyzer (reaction reagent) | Temperature of reaction (℃) | Reaction times (hr) | Transformation efficiency (%) | Selectivity (%) | Productive rate (%) | ||
Kind | Usage quantity 1) | ||||||
Embodiment 1 | Anhydrous AlCl 3 | 0.5mol | 5~10 | 2.0 | 54.5 | 88.6 | 47.4 |
Comparative example 1 | NaH | 1.1mol | 95 | 1.0 | 68.8 | 61.6 | 42.4 |
Experiment numbers | Catalyzer (reaction reagent) | Temperature of reaction (℃) | Reaction times (hr) | Transformation efficiency (%) | Selectivity (%) | Productive rate (%) | |
Kind | Usage quantity 1) | ||||||
1 | Anhydrous AlCl 3 | 0.2mol | 40 | 2.0 | 38.8 | 86.2 | 33.5 |
2 | ZnCl 2 | 0.2mol | 40 | 3.0 | 27.4 | 91.2 | 25.0 |
3 | BF 3·OEt 2 | 0.2mol | 40 | 2.0 | 49.7 | 48.7 | 24.2 |
Claims (4)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP111597/2003 | 2003-04-16 | ||
JP2003111597A JP4179916B2 (en) | 2003-04-16 | 2003-04-16 | Process for producing 2- (l-menthoxy) ethanol |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1764622A true CN1764622A (en) | 2006-04-26 |
CN100366596C CN100366596C (en) | 2008-02-06 |
Family
ID=33296001
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB2004800078636A Expired - Fee Related CN100366596C (en) | 2003-04-16 | 2004-03-10 | Process for producing 2-(l-menthoxy)ethanol compound |
Country Status (5)
Country | Link |
---|---|
JP (1) | JP4179916B2 (en) |
KR (1) | KR20050114238A (en) |
CN (1) | CN100366596C (en) |
ES (1) | ES2267408B1 (en) |
WO (1) | WO2004092104A1 (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102964223A (en) * | 2012-11-13 | 2013-03-13 | 宁波杭州湾新区珠峰企业管理服务有限公司 | Preparation method of propylene glycol monomethyl ether |
CN104876944A (en) * | 2015-05-13 | 2015-09-02 | 上海适济生物科技有限公司 | Preparation method of everolimus |
CN106146536A (en) * | 2015-04-25 | 2016-11-23 | 山东新时代药业有限公司 | A kind of preparation method of everolimus |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5863019B2 (en) * | 2011-10-27 | 2016-02-16 | 高砂香料工業株式会社 | Method for producing 3-mentoxypropanol, and cooling agent composition |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2001294546A (en) * | 2000-02-28 | 2001-10-23 | Takasago Internatl Corp | (1'r,2's,5'r)3-1-menthoxyalkan-1-ol cold-sensing agent |
JP4587549B2 (en) * | 2000-10-23 | 2010-11-24 | 高砂香料工業株式会社 | 1-halogeno-3-l-menthoxypropan-2-ol |
JP4723751B2 (en) * | 2001-04-23 | 2011-07-13 | 高砂香料工業株式会社 | Process for producing 3-l-menthoxypropane-1,2-diol |
-
2003
- 2003-04-16 JP JP2003111597A patent/JP4179916B2/en not_active Expired - Fee Related
-
2004
- 2004-03-10 ES ES200550060A patent/ES2267408B1/en not_active Expired - Fee Related
- 2004-03-10 KR KR1020057017345A patent/KR20050114238A/en not_active Application Discontinuation
- 2004-03-10 WO PCT/JP2004/003058 patent/WO2004092104A1/en active IP Right Grant
- 2004-03-10 CN CNB2004800078636A patent/CN100366596C/en not_active Expired - Fee Related
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102964223A (en) * | 2012-11-13 | 2013-03-13 | 宁波杭州湾新区珠峰企业管理服务有限公司 | Preparation method of propylene glycol monomethyl ether |
CN106146536A (en) * | 2015-04-25 | 2016-11-23 | 山东新时代药业有限公司 | A kind of preparation method of everolimus |
CN104876944A (en) * | 2015-05-13 | 2015-09-02 | 上海适济生物科技有限公司 | Preparation method of everolimus |
CN104876944B (en) * | 2015-05-13 | 2017-11-10 | 普济生物科技(台州)有限公司 | A kind of preparation method of everolimus |
Also Published As
Publication number | Publication date |
---|---|
WO2004092104A1 (en) | 2004-10-28 |
ES2267408A1 (en) | 2007-03-01 |
ES2267408B1 (en) | 2008-04-01 |
JP2004315427A (en) | 2004-11-11 |
CN100366596C (en) | 2008-02-06 |
JP4179916B2 (en) | 2008-11-12 |
KR20050114238A (en) | 2005-12-05 |
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Legal Events
Date | Code | Title | Description |
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C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
EE01 | Entry into force of recordation of patent licensing contract |
Assignee: Shanghai Takasago-Union Fragrances & Flavors Co., Ltd. Assignor: Takamasago Perfume Industrial Co., Ltd. Contract fulfillment period: 2008.2.20 to 2014.2.19 contract change Contract record no.: 2008990000732 Denomination of invention: Preparation method of 2- (L- peppermint) alcohol compound Granted publication date: 20080206 License type: Exclusive license Record date: 20081014 |
|
LIC | Patent licence contract for exploitation submitted for record |
Free format text: EXCLUSIVE LICENSE; TIME LIMIT OF IMPLEMENTING CONTACT: 2008.2.20 TO 2014.2.19; CHANGE OF CONTRACT Name of requester: SHANGHAI TAKASAGO JIANCHEN SPICE CO., LTD. Effective date: 20081014 |
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CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20080206 Termination date: 20160310 |
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CF01 | Termination of patent right due to non-payment of annual fee |