JPS6033809B2 - シクロアルカノン及びシクロアルカノールの製造方法 - Google Patents
シクロアルカノン及びシクロアルカノールの製造方法Info
- Publication number
- JPS6033809B2 JPS6033809B2 JP6638276A JP6638276A JPS6033809B2 JP S6033809 B2 JPS6033809 B2 JP S6033809B2 JP 6638276 A JP6638276 A JP 6638276A JP 6638276 A JP6638276 A JP 6638276A JP S6033809 B2 JPS6033809 B2 JP S6033809B2
- Authority
- JP
- Japan
- Prior art keywords
- conversion
- chromium
- reaction
- catalyst
- stripping
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 31
- 239000003054 catalyst Substances 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 16
- -1 cycloalkyl hydroperoxides Chemical class 0.000 claims description 15
- 239000011541 reaction mixture Substances 0.000 claims description 8
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims description 6
- 229910000423 chromium oxide Inorganic materials 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 12
- 229910052804 chromium Inorganic materials 0.000 description 9
- 239000011651 chromium Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- 239000007789 gas Substances 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 5
- 150000002978 peroxides Chemical group 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- 150000001924 cycloalkanes Chemical class 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 150000001845 chromium compounds Chemical class 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 229910001882 dioxygen Inorganic materials 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 235000017166 Bambusa arundinacea Nutrition 0.000 description 1
- 235000017491 Bambusa tulda Nutrition 0.000 description 1
- 241001330002 Bambuseae Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- 235000015334 Phyllostachys viridis Nutrition 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000011425 bamboo Substances 0.000 description 1
- 239000006227 byproduct Substances 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
- 239000000969 carrier Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- VQWFNAGFNGABOH-UHFFFAOYSA-K chromium(iii) hydroxide Chemical compound [OH-].[OH-].[OH-].[Cr+3] VQWFNAGFNGABOH-UHFFFAOYSA-K 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 239000012045 crude solution Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 238000005406 washing Methods 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
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/53—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of hydroperoxides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL7506790 | 1975-06-07 | ||
| NL7506790A NL7506790A (nl) | 1975-06-07 | 1975-06-07 | Werkwijze voor het bereiden van cycloalkanonen en cycloalkanolen. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS51146437A JPS51146437A (en) | 1976-12-16 |
| JPS6033809B2 true JPS6033809B2 (ja) | 1985-08-05 |
Family
ID=19823915
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6638276A Expired JPS6033809B2 (ja) | 1975-06-07 | 1976-06-07 | シクロアルカノン及びシクロアルカノールの製造方法 |
Country Status (15)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10610914B2 (en) | 2015-03-30 | 2020-04-07 | Baoshan Iron & Steel Co., Ltd. | Rolling method for boards with different longitudinal thicknesses |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1590958A (en) * | 1976-12-31 | 1981-06-10 | Ici Ltd | Oxidation of cyclohexane |
| NL8201695A (nl) * | 1982-04-23 | 1983-11-16 | Stamicarbon | Werkwijze voor de bereiding van cyclohexanol en cyclohexanon. |
| RU2154050C1 (ru) * | 1999-01-19 | 2000-08-10 | Ярославский государственный технический университет | Способ получения циклоалканонов c8-c12 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL43433A (en) * | 1972-10-21 | 1976-09-30 | Stamicarbon | Process for preparing cycloalkanones and cycloalkanols |
| CA1049041A (en) * | 1972-11-23 | 1979-02-20 | Stamicarbon B.V. | Process for the preparation of cycloalkanones and/or cycloalkanols |
-
1975
- 1975-06-07 NL NL7506790A patent/NL7506790A/xx not_active Application Discontinuation
-
1976
- 1976-01-01 AR AR26349376A patent/AR206572A1/es active
- 1976-06-03 CA CA253,976A patent/CA1070328A/en not_active Expired
- 1976-06-04 DD DD19319576A patent/DD124971A6/xx unknown
- 1976-06-04 BE BE167662A patent/BE842635R/xx not_active IP Right Cessation
- 1976-06-04 GB GB2326776A patent/GB1535869A/en not_active Expired
- 1976-06-04 BR BR7603568A patent/BR7603568A/pt unknown
- 1976-06-04 FR FR7617017A patent/FR2313336A2/fr active Granted
- 1976-06-04 CH CH767120A patent/CH608774A5/xx not_active IP Right Cessation
- 1976-06-04 DE DE19762625273 patent/DE2625273A1/de not_active Ceased
- 1976-06-04 ES ES448576A patent/ES448576A2/es not_active Expired
- 1976-06-07 IT IT2403376A patent/IT1061404B/it active
- 1976-06-07 MX MX16500676A patent/MX144251A/es unknown
- 1976-06-07 JP JP6638276A patent/JPS6033809B2/ja not_active Expired
- 1976-06-07 PL PL19019276A patent/PL101224B3/pl unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10610914B2 (en) | 2015-03-30 | 2020-04-07 | Baoshan Iron & Steel Co., Ltd. | Rolling method for boards with different longitudinal thicknesses |
Also Published As
| Publication number | Publication date |
|---|---|
| ES448576A2 (es) | 1977-07-16 |
| DE2625273A1 (de) | 1976-12-16 |
| JPS51146437A (en) | 1976-12-16 |
| DD124971A6 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-03-23 |
| NL7506790A (nl) | 1976-12-09 |
| FR2313336A2 (fr) | 1976-12-31 |
| CA1070328A (en) | 1980-01-22 |
| BE842635R (nl) | 1976-12-06 |
| CH608774A5 (en) | 1979-01-31 |
| PL101224B3 (pl) | 1978-12-30 |
| MX144251A (es) | 1981-09-18 |
| FR2313336B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1981-06-12 |
| AR206572A1 (es) | 1976-07-30 |
| BR7603568A (pt) | 1977-01-04 |
| IT1061404B (it) | 1983-02-28 |
| GB1535869A (en) | 1978-12-13 |
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