JPS6133184A - ｌ−アンブロツクスの製造方法 - Google Patents
ｌ−アンブロツクスの製造方法Info
- Publication number
- JPS6133184A JPS6133184A JP59153670A JP15367084A JPS6133184A JP S6133184 A JPS6133184 A JP S6133184A JP 59153670 A JP59153670 A JP 59153670A JP 15367084 A JP15367084 A JP 15367084A JP S6133184 A JPS6133184 A JP S6133184A
- Authority
- JP
- Japan
- Prior art keywords
- solid acid
- catalyst
- ambrox
- reaction
- sclareol
- 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
- 238000002360 preparation method Methods 0.000 title description 3
- XVULBTBTFGYVRC-HHUCQEJWSA-N sclareol Chemical compound CC1(C)CCC[C@]2(C)[C@@H](CC[C@](O)(C)C=C)[C@](C)(O)CC[C@H]21 XVULBTBTFGYVRC-HHUCQEJWSA-N 0.000 claims abstract description 42
- 239000003054 catalyst Substances 0.000 claims abstract description 28
- 239000011973 solid acid Substances 0.000 claims abstract description 27
- XVULBTBTFGYVRC-UHFFFAOYSA-N Episclareol Natural products CC1(C)CCCC2(C)C(CCC(O)(C)C=C)C(C)(O)CCC21 XVULBTBTFGYVRC-UHFFFAOYSA-N 0.000 claims abstract description 18
- LAEIZWJAQRGPDA-UHFFFAOYSA-N Manoyloxid Natural products CC1(C)CCCC2(C)C3CC=C(C)OC3(C)CCC21 LAEIZWJAQRGPDA-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000006297 dehydration reaction Methods 0.000 claims abstract description 16
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 11
- 239000012286 potassium permanganate Substances 0.000 claims abstract description 11
- 239000003444 phase transfer catalyst Substances 0.000 claims abstract description 10
- 239000000126 substance Substances 0.000 claims abstract description 8
- YPZUZOLGGMJZJO-LQKXBSAESA-N ambroxan Chemical compound CC([C@@H]1CC2)(C)CCC[C@]1(C)[C@@H]1[C@]2(C)OCC1 YPZUZOLGGMJZJO-LQKXBSAESA-N 0.000 claims description 16
- YPZUZOLGGMJZJO-UHFFFAOYSA-N ambrofix Natural products C1CC2C(C)(C)CCCC2(C)C2C1(C)OCC2 YPZUZOLGGMJZJO-UHFFFAOYSA-N 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 230000002378 acidificating effect Effects 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 5
- 239000011707 mineral Substances 0.000 claims description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000004927 clay Substances 0.000 claims description 4
- 239000007848 Bronsted acid Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052570 clay Inorganic materials 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 229910052698 phosphorus Chemical group 0.000 claims description 2
- 239000011574 phosphorus Chemical group 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 24
- 239000000203 mixture Substances 0.000 abstract description 15
- 238000000034 method Methods 0.000 abstract description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract description 8
- 239000002904 solvent Substances 0.000 abstract description 7
- 230000003647 oxidation Effects 0.000 abstract description 6
- 238000007796 conventional method Methods 0.000 abstract description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 3
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 abstract description 3
- 230000001590 oxidative effect Effects 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
- 150000002009 diols Chemical class 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
- 230000018044 dehydration Effects 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- 239000008096 xylene Substances 0.000 description 7
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- HQCVEGNPQFRFPC-UHFFFAOYSA-N carboxy acetate Chemical compound CC(=O)OC(O)=O HQCVEGNPQFRFPC-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 239000012280 lithium aluminium hydride Substances 0.000 description 4
- -1 lithium aluminum hydride Chemical compound 0.000 description 4
- 235000010755 mineral Nutrition 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 241000208125 Nicotiana Species 0.000 description 3
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 3
- 238000007273 lactonization reaction Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 235000010265 sodium sulphite Nutrition 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- MQRJBSHKWOFOGF-UHFFFAOYSA-L disodium;carbonate;hydrate Chemical compound O.[Na+].[Na+].[O-]C([O-])=O MQRJBSHKWOFOGF-UHFFFAOYSA-L 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 239000010670 sage oil Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000004575 stone Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 238000006418 Brown reaction Methods 0.000 description 1
- 241000283153 Cetacea Species 0.000 description 1
- PRNUCJKOERXADE-UHFFFAOYSA-N Cinnamalacetone Chemical compound CC(=O)C=CC=CC1=CC=CC=C1 PRNUCJKOERXADE-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 235000019506 cigar Nutrition 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229930004069 diterpene Natural products 0.000 description 1
- 150000004141 diterpene derivatives Chemical class 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000012260 resinous material Substances 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Furan Compounds (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Fats And Perfumes (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59153670A JPS6133184A (ja) | 1984-07-24 | 1984-07-24 | ｌ−アンブロツクスの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59153670A JPS6133184A (ja) | 1984-07-24 | 1984-07-24 | ｌ−アンブロツクスの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6133184A true JPS6133184A (ja) | 1986-02-17 |
| JPH0358346B2 JPH0358346B2 (enrdf_load_stackoverflow) | 1991-09-05 |
Family
ID=15567604
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59153670A Granted JPS6133184A (ja) | 1984-07-24 | 1984-07-24 | ｌ−アンブロツクスの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6133184A (enrdf_load_stackoverflow) |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5274134A (en) * | 1989-04-14 | 1993-12-28 | Henkel Kommanditgesellschaft Auf Aktien | Process for the stereoselective preparation of 8α, 12-oxido-13, 14,15, 16-tetranorlabdane |
| WO1995015320A1 (de) * | 1993-12-03 | 1995-06-08 | Henkel Kommanditgesellschaft Auf Aktien | VERFAHREN ZUR HERSTELLUNG VON 8α,12-OXIDO-13,14,15,16-TETRANORLABDAN |
| WO1995015321A1 (de) * | 1993-12-03 | 1995-06-08 | Henkel Kommanditgesellschaft Auf Aktien | VERFAHREN ZUR HERSTELLUNG VON 8α,12-OXIDO-13,14,15,16-TETRANORLABDAN |
| EP0752423A1 (de) * | 1995-07-06 | 1997-01-08 | Basf Aktiengesellschaft | Verfahren zur stereoselektiven Herstellung von (-)3a,6,6,9a-Tetramethyl-perhydronaphtho[2,1-b]furan |
| EP0696587A3 (de) * | 1994-08-08 | 1998-06-10 | Basf Aktiengesellschaft | Verfahren zur stereoselektiven Herstellung von (-)3a,6,6,9a-Tetramethyl-perhydronaphtho[2,1-b]furan |
| US5811560A (en) * | 1994-11-05 | 1998-09-22 | Henkel Kommanditgesellschaft Auf Aktien | Process for the production of 8α, 12-oxido-13, 14,15,16-tetranorlabdane |
| ES2195777A1 (es) * | 2002-03-22 | 2003-12-01 | Univ Granada | Procedimiento para la obtencion de productos olorosos tipo ambar gris a partir de esclareol. |
| WO2013007832A1 (en) | 2011-07-13 | 2013-01-17 | Koste Biochemicals | Process for the cyclodehydration of diols and use thereof for the manufacturing of ambrafuran and other cycloether derivatives |
| JP2017507924A (ja) * | 2014-01-24 | 2017-03-23 | ジボダン エス エー | 有機化合物における、または有機化合物に関する改良 |
| JP2020048560A (ja) * | 2015-04-24 | 2020-04-02 | ジボダン エス エー | 酵素およびその適用 |
| CN112973725A (zh) * | 2021-03-08 | 2021-06-18 | 重庆化工职业学院 | 用于香紫苏醇氧化合成香紫苏内酯的催化剂 |
| CN117164538A (zh) * | 2023-08-29 | 2023-12-05 | 新疆大学 | 一种一锅两步制备降龙涎醚的方法 |
-
1984
- 1984-07-24 JP JP59153670A patent/JPS6133184A/ja active Granted
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5274134A (en) * | 1989-04-14 | 1993-12-28 | Henkel Kommanditgesellschaft Auf Aktien | Process for the stereoselective preparation of 8α, 12-oxido-13, 14,15, 16-tetranorlabdane |
| WO1995015320A1 (de) * | 1993-12-03 | 1995-06-08 | Henkel Kommanditgesellschaft Auf Aktien | VERFAHREN ZUR HERSTELLUNG VON 8α,12-OXIDO-13,14,15,16-TETRANORLABDAN |
| WO1995015321A1 (de) * | 1993-12-03 | 1995-06-08 | Henkel Kommanditgesellschaft Auf Aktien | VERFAHREN ZUR HERSTELLUNG VON 8α,12-OXIDO-13,14,15,16-TETRANORLABDAN |
| US5670670A (en) * | 1993-12-03 | 1997-09-23 | Henkel Kommanditgesellschaft Auf Aktien | Process for the production of 8 α, 12-oxido-13,14,15,16-tetranorlabdane |
| US5688976A (en) * | 1993-12-03 | 1997-11-18 | Henkel Kommanditgesellschaft Auf Aktien | Process for the production of 8 α, 12-oxido-13,14,15,16-tetranorlabdane |
| EP0696587A3 (de) * | 1994-08-08 | 1998-06-10 | Basf Aktiengesellschaft | Verfahren zur stereoselektiven Herstellung von (-)3a,6,6,9a-Tetramethyl-perhydronaphtho[2,1-b]furan |
| US5811560A (en) * | 1994-11-05 | 1998-09-22 | Henkel Kommanditgesellschaft Auf Aktien | Process for the production of 8α, 12-oxido-13, 14,15,16-tetranorlabdane |
| EP0752423A1 (de) * | 1995-07-06 | 1997-01-08 | Basf Aktiengesellschaft | Verfahren zur stereoselektiven Herstellung von (-)3a,6,6,9a-Tetramethyl-perhydronaphtho[2,1-b]furan |
| ES2195777A1 (es) * | 2002-03-22 | 2003-12-01 | Univ Granada | Procedimiento para la obtencion de productos olorosos tipo ambar gris a partir de esclareol. |
| WO2013007832A1 (en) | 2011-07-13 | 2013-01-17 | Koste Biochemicals | Process for the cyclodehydration of diols and use thereof for the manufacturing of ambrafuran and other cycloether derivatives |
| US9469622B2 (en) | 2011-07-13 | 2016-10-18 | Koste Biochemicals Sas | Process for the cyclodehydration of diols and use thereof for the manufacturing of ambrafuran and other cycloether derivatives |
| JP2017507924A (ja) * | 2014-01-24 | 2017-03-23 | ジボダン エス エー | 有機化合物における、または有機化合物に関する改良 |
| JP2020048560A (ja) * | 2015-04-24 | 2020-04-02 | ジボダン エス エー | 酵素およびその適用 |
| CN112973725A (zh) * | 2021-03-08 | 2021-06-18 | 重庆化工职业学院 | 用于香紫苏醇氧化合成香紫苏内酯的催化剂 |
| CN117164538A (zh) * | 2023-08-29 | 2023-12-05 | 新疆大学 | 一种一锅两步制备降龙涎醚的方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0358346B2 (enrdf_load_stackoverflow) | 1991-09-05 |
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