JPS6348518B2 - - Google Patents
Info
- Publication number
- JPS6348518B2 JPS6348518B2 JP2687881A JP2687881A JPS6348518B2 JP S6348518 B2 JPS6348518 B2 JP S6348518B2 JP 2687881 A JP2687881 A JP 2687881A JP 2687881 A JP2687881 A JP 2687881A JP S6348518 B2 JPS6348518 B2 JP S6348518B2
- Authority
- JP
- Japan
- Prior art keywords
- added
- ether
- solvent
- carbon source
- hexadecene
- 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
- 150000002576 ketones Chemical class 0.000 claims description 13
- 150000003333 secondary alcohols Chemical class 0.000 claims description 11
- 241000894006 Bacteria Species 0.000 claims description 9
- 241000186216 Corynebacterium Species 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 64
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 54
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
- 239000002904 solvent Substances 0.000 description 32
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 30
- 229910052799 carbon Inorganic materials 0.000 description 30
- 238000005481 NMR spectroscopy Methods 0.000 description 26
- 229910017053 inorganic salt Inorganic materials 0.000 description 21
- 241000158504 Rhodococcus hoagii Species 0.000 description 20
- 238000010828 elution Methods 0.000 description 20
- 239000000203 mixture Substances 0.000 description 20
- 239000000758 substrate Substances 0.000 description 18
- -1 acetophenone Chemical class 0.000 description 13
- 238000001228 spectrum Methods 0.000 description 13
- 239000000126 substance Substances 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- 239000000284 extract Substances 0.000 description 8
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 8
- 238000010898 silica gel chromatography Methods 0.000 description 7
- 238000001816 cooling Methods 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 244000005700 microbiome Species 0.000 description 4
- 230000001590 oxidative effect Effects 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- OURDGVVUMHJQPZ-UHFFFAOYSA-N CCCCCC(=O)CCCCCCCCC=C Chemical compound CCCCCC(=O)CCCCCCCCC=C OURDGVVUMHJQPZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- ADGQOCBSNYMAQS-UHFFFAOYSA-N hexadecan-6-ol Chemical compound CCCCCCCCCCC(O)CCCCC ADGQOCBSNYMAQS-UHFFFAOYSA-N 0.000 description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 231100000331 toxic Toxicity 0.000 description 3
- 230000002588 toxic effect Effects 0.000 description 3
- WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical compound CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 description 2
- HORQAOAYAYGIBM-UHFFFAOYSA-N 2,4-dinitrophenylhydrazine Chemical compound NNC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O HORQAOAYAYGIBM-UHFFFAOYSA-N 0.000 description 2
- LSKONYYRONEBKA-UHFFFAOYSA-N 2-Dodecanone Natural products CCCCCCCCCCC(C)=O LSKONYYRONEBKA-UHFFFAOYSA-N 0.000 description 2
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229940041514 candida albicans extract Drugs 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000012531 culture fluid Substances 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- XSWSEQPWKOWORN-UHFFFAOYSA-N dodecan-2-ol Chemical compound CCCCCCCCCCC(C)O XSWSEQPWKOWORN-UHFFFAOYSA-N 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- CIAHHJXQZXLMPN-UHFFFAOYSA-N hexadecan-6-one Chemical compound CCCCCCCCCCC(=O)CCCCC CIAHHJXQZXLMPN-UHFFFAOYSA-N 0.000 description 2
- SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- KATMMOGJSFLTOP-UHFFFAOYSA-N tetradecan-6-ol Chemical compound CCCCCCCCC(O)CCCCC KATMMOGJSFLTOP-UHFFFAOYSA-N 0.000 description 2
- ZQJQCHXLJMURLU-UHFFFAOYSA-N tridec-1-en-3-ol Chemical compound CCCCCCCCCCC(O)C=C ZQJQCHXLJMURLU-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000012138 yeast extract Substances 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- AXEBZXVSNOWYPZ-UHFFFAOYSA-N 1-phenylundec-1-en-3-ol Chemical compound CCCCCCCCC(O)C=CC1=CC=CC=C1 AXEBZXVSNOWYPZ-UHFFFAOYSA-N 0.000 description 1
- CYEZIZHBBKGLCX-UHFFFAOYSA-N 1-phenylundecan-1-ol Chemical compound CCCCCCCCCCC(O)C1=CC=CC=C1 CYEZIZHBBKGLCX-UHFFFAOYSA-N 0.000 description 1
- LHJBFOGCFZHBAJ-UHFFFAOYSA-N 1-phenylundecan-1-one Chemical compound CCCCCCCCCCC(=O)C1=CC=CC=C1 LHJBFOGCFZHBAJ-UHFFFAOYSA-N 0.000 description 1
- QPUYZXRKXDVOCO-UHFFFAOYSA-N 1-phenylundecan-3-ol Chemical compound CCCCCCCCC(O)CCC1=CC=CC=C1 QPUYZXRKXDVOCO-UHFFFAOYSA-N 0.000 description 1
- NBUFWOBFHJBDRQ-UHFFFAOYSA-N 1-phenylundecan-3-one Chemical compound CCCCCCCCC(=O)CCC1=CC=CC=C1 NBUFWOBFHJBDRQ-UHFFFAOYSA-N 0.000 description 1
- PQESRTWBQJRGON-UHFFFAOYSA-N 8-hydroxytetradecan-7-one Chemical compound CCCCCCC(O)C(=O)CCCCCC PQESRTWBQJRGON-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- XPNGNIFUDRPBFJ-UHFFFAOYSA-N alpha-methylbenzylalcohol Natural products CC1=CC=CC=C1CO XPNGNIFUDRPBFJ-UHFFFAOYSA-N 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- IHOLJZJZVIFXKA-UHFFFAOYSA-N dodec-11-en-2-ol Chemical compound CC(O)CCCCCCCCC=C IHOLJZJZVIFXKA-UHFFFAOYSA-N 0.000 description 1
- OPLPMLGBZCNBGS-UHFFFAOYSA-N dodec-11-en-2-one Chemical compound CC(=O)CCCCCCCCC=C OPLPMLGBZCNBGS-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000004967 organic peroxy acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- MEHHKSPCNQCVCK-UHFFFAOYSA-N pentadecan-5-ol Chemical compound CCCCCCCCCCC(O)CCCC MEHHKSPCNQCVCK-UHFFFAOYSA-N 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- OAFHCOXSIJKFEV-UHFFFAOYSA-N tetradecan-6-one Chemical compound CCCCCCCCC(=O)CCCCC OAFHCOXSIJKFEV-UHFFFAOYSA-N 0.000 description 1
- XKZGHFFSJSBUFA-UHFFFAOYSA-N tetradecane-7,8-diol Chemical group CCCCCCC(O)C(O)CCCCCC XKZGHFFSJSBUFA-UHFFFAOYSA-N 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- CNJBRDUPIHYDFA-UHFFFAOYSA-N tridec-1-en-3-one Chemical compound CCCCCCCCCCC(=O)C=C CNJBRDUPIHYDFA-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2687881A JPS57141295A (en) | 1981-02-27 | 1981-02-27 | Preparation of ketone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2687881A JPS57141295A (en) | 1981-02-27 | 1981-02-27 | Preparation of ketone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57141295A JPS57141295A (en) | 1982-09-01 |
| JPS6348518B2 true JPS6348518B2 (enrdf_load_stackoverflow) | 1988-09-29 |
Family
ID=12205544
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2687881A Granted JPS57141295A (en) | 1981-02-27 | 1981-02-27 | Preparation of ketone |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57141295A (enrdf_load_stackoverflow) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0228414A4 (en) * | 1985-06-21 | 1989-08-09 | Wisconsin Alumni Res Found | Process for preparing 4-hydroxycyclopent-2-en-1-one. |
| AT386840B (de) * | 1987-01-29 | 1988-10-25 | Vogelbusch Gmbh | Verfahren zur herstellung von zuckersirupen durch enzymatische direktverzuckerung von staerkereichen rohstoffen, insbesondere frischen oder getrockneten cassavawurzeln |
| FR2643647B1 (fr) * | 1989-02-27 | 1991-06-21 | Sanofi Sa | Procede microbiologique d'obtention de methylcetones |
| GB2237018A (en) * | 1989-08-18 | 1991-04-24 | Medeva Plc | Secondary alcohols and compositions containing fatty acids or esters |
-
1981
- 1981-02-27 JP JP2687881A patent/JPS57141295A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57141295A (en) | 1982-09-01 |
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