JP2005528357A - シクロヘキサノンの製造方法 - Google Patents
シクロヘキサノンの製造方法 Download PDFInfo
- Publication number
- JP2005528357A JP2005528357A JP2003576383A JP2003576383A JP2005528357A JP 2005528357 A JP2005528357 A JP 2005528357A JP 2003576383 A JP2003576383 A JP 2003576383A JP 2003576383 A JP2003576383 A JP 2003576383A JP 2005528357 A JP2005528357 A JP 2005528357A
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- carried out
- cyclohexene
- inert gas
- mixture
- 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.)
- Pending
Links
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 title claims abstract description 46
- 238000004519 manufacturing process Methods 0.000 title abstract description 10
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims abstract description 56
- 238000000034 method Methods 0.000 claims abstract description 47
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 claims abstract description 36
- 229960001730 nitrous oxide Drugs 0.000 claims abstract description 25
- 239000000203 mixture Substances 0.000 claims abstract description 24
- 239000011261 inert gas Substances 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims description 46
- 239000007789 gas Substances 0.000 claims description 10
- 239000001272 nitrous oxide Substances 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 9
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 6
- 239000002360 explosive Substances 0.000 claims description 3
- 230000003068 static effect Effects 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 2
- 238000010790 dilution Methods 0.000 claims 1
- 239000012895 dilution Substances 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 abstract description 10
- 239000007791 liquid phase Substances 0.000 abstract description 8
- 238000004880 explosion Methods 0.000 abstract description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- 230000001590 oxidative effect Effects 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 229910004298 SiO 2 Inorganic materials 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229930195734 saturated hydrocarbon Natural products 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910021536 Zeolite Inorganic materials 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000010457 zeolite Substances 0.000 description 2
- JLGADZLAECENGR-UHFFFAOYSA-N 1,1-dibromo-1,2,2,2-tetrafluoroethane Chemical compound FC(F)(F)C(F)(Br)Br JLGADZLAECENGR-UHFFFAOYSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- MEXUFEQDCXZEON-UHFFFAOYSA-N bromochlorodifluoromethane Chemical compound FC(F)(Cl)Br MEXUFEQDCXZEON-UHFFFAOYSA-N 0.000 description 1
- RJCQBQGAPKAMLL-UHFFFAOYSA-N bromotrifluoromethane Chemical compound FC(F)(F)Br RJCQBQGAPKAMLL-UHFFFAOYSA-N 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 238000001027 hydrothermal synthesis Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 239000001294 propane Substances 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
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/28—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of CHx-moieties
-
- 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
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| RU2002107019/04A RU2205175C1 (ru) | 2002-03-20 | 2002-03-20 | Способ получения циклогексанона |
| PCT/RU2002/000438 WO2003078374A1 (en) | 2002-03-20 | 2002-09-30 | Method for producing cyclohexanone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005528357A true JP2005528357A (ja) | 2005-09-22 |
| JP2005528357A5 JP2005528357A5 (https=) | 2006-01-05 |
Family
ID=20255444
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003576383A Pending JP2005528357A (ja) | 2002-03-20 | 2002-09-30 | シクロヘキサノンの製造方法 |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JP2005528357A (https=) |
| AU (1) | AU2002335569A1 (https=) |
| RU (1) | RU2205175C1 (https=) |
| WO (1) | WO2003078374A1 (https=) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009516633A (ja) * | 2005-11-22 | 2009-04-23 | ビーエーエスエフ ソシエタス・ヨーロピア | 一酸化二窒素を単離する方法 |
| JP2012500826A (ja) * | 2008-08-29 | 2012-01-12 | ビーエーエスエフ ソシエタス・ヨーロピア | 環式ケトンの製造方法 |
| JP2012508268A (ja) * | 2008-11-11 | 2012-04-05 | ビーエーエスエフ ソシエタス・ヨーロピア | 環状ジアミンの製造方法 |
| JP2012526561A (ja) * | 2009-05-15 | 2012-11-01 | ゲノマチカ， インク． | シクロヘキサノンの産生のための生物 |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102004046171A1 (de) | 2004-09-23 | 2006-04-13 | Basf Ag | Verfahren zur Herstellung von Cyclopentanon |
| DE102004046167A1 (de) | 2004-09-23 | 2006-04-06 | Basf Ag | Verfahren zur Reinigung und Aufkonzentrierung von Distickstoffmonoxid |
| JP5086342B2 (ja) | 2006-06-29 | 2012-11-28 | ビーエーエスエフ ソシエタス・ヨーロピア | 環状ケトンの製造方法 |
| KR101374007B1 (ko) | 2006-06-29 | 2014-03-12 | 바스프 에스이 | 시클릭 케톤의 제조 방법 |
| JP5244121B2 (ja) | 2006-12-11 | 2013-07-24 | ビーエーエスエフ ソシエタス・ヨーロピア | Ｎ２ｏを単離する方法 |
| WO2009121707A1 (de) | 2008-04-02 | 2009-10-08 | Basf Se | Verfahren zur reinigung von distickstoffmonoxid |
| JP5372135B2 (ja) | 2008-04-02 | 2013-12-18 | ビーエーエスエフ ソシエタス・ヨーロピア | Ｎ２ｏの精製方法 |
| EP2384317B1 (de) | 2008-12-30 | 2014-04-23 | Basf Se | Verfahren zur herstellung von ketonen durch umsetzung von 1,1-disubtituierten olefinen mit n2o |
| GB201019701D0 (en) | 2010-11-19 | 2011-01-05 | Invista Tech Sarl | Reaction process |
| RU2618273C1 (ru) * | 2015-11-10 | 2017-05-03 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Московский технологический университет " | Способ выделения циклогексанона из реакционной смеси вода - ацетонитрил - циклогексен - циклогексанон |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB649680A (en) * | 1948-09-22 | 1951-01-31 | Gerard Dunstan Buckley | Manufacture of oxidation products from olefinic compounds |
| SU692826A1 (ru) * | 1978-06-12 | 1979-10-25 | Ленинградский Ордена Трудового Красного Знамени Технологический Институт Им. Ленсовета | Способ получени циклогексанона |
| DE3203286A1 (de) * | 1981-03-20 | 1982-12-09 | The Agency of Industrial Science and Technology, Tokyo | Verfahren zur herstellung von zyklohexanon |
| NL8801036A (nl) * | 1988-04-21 | 1989-11-16 | Stamicarbon | Werkwijze voor de bereiding van cyclohexanol en/of cyclohexanon. |
-
2002
- 2002-03-20 RU RU2002107019/04A patent/RU2205175C1/ru not_active IP Right Cessation
- 2002-09-30 JP JP2003576383A patent/JP2005528357A/ja active Pending
- 2002-09-30 AU AU2002335569A patent/AU2002335569A1/en not_active Abandoned
- 2002-09-30 WO PCT/RU2002/000438 patent/WO2003078374A1/ru not_active Ceased
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009516633A (ja) * | 2005-11-22 | 2009-04-23 | ビーエーエスエフ ソシエタス・ヨーロピア | 一酸化二窒素を単離する方法 |
| JP2012500826A (ja) * | 2008-08-29 | 2012-01-12 | ビーエーエスエフ ソシエタス・ヨーロピア | 環式ケトンの製造方法 |
| JP2012508268A (ja) * | 2008-11-11 | 2012-04-05 | ビーエーエスエフ ソシエタス・ヨーロピア | 環状ジアミンの製造方法 |
| JP2012526561A (ja) * | 2009-05-15 | 2012-11-01 | ゲノマチカ， インク． | シクロヘキサノンの産生のための生物 |
Also Published As
| Publication number | Publication date |
|---|---|
| RU2205175C1 (ru) | 2003-05-27 |
| AU2002335569A1 (en) | 2003-09-29 |
| WO2003078374A1 (en) | 2003-09-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20050927 |
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| A621 | Written request for application examination |
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