SE331837B - - Google Patents
Info
- Publication number
- SE331837B SE331837B SE07555/63A SE755563A SE331837B SE 331837 B SE331837 B SE 331837B SE 07555/63 A SE07555/63 A SE 07555/63A SE 755563 A SE755563 A SE 755563A SE 331837 B SE331837 B SE 331837B
- Authority
- SE
- Sweden
- Prior art keywords
- benzene
- cyclohexane
- line
- cycloalkane
- oxidation
- Prior art date
Links
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 24
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 abstract 8
- 238000007254 oxidation reaction Methods 0.000 abstract 7
- 150000001924 cycloalkanes Chemical class 0.000 abstract 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 abstract 6
- 230000003647 oxidation Effects 0.000 abstract 5
- 239000000203 mixture Substances 0.000 abstract 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 abstract 3
- 238000005984 hydrogenation reaction Methods 0.000 abstract 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- -1 borate ester Chemical class 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000003999 initiator Substances 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- VGTPKLINSHNZRD-UHFFFAOYSA-N oxoborinic acid Chemical compound OB=O VGTPKLINSHNZRD-UHFFFAOYSA-N 0.000 abstract 2
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 abstract 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 150000001639 boron compounds Chemical class 0.000 abstract 1
- 150000001642 boronic acid derivatives Chemical class 0.000 abstract 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 abstract 1
- 239000012969 di-tertiary-butyl peroxide Substances 0.000 abstract 1
- 229910001882 dioxygen Inorganic materials 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 238000010926 purge Methods 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 238000011084 recovery Methods 0.000 abstract 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/48—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups
- C07C29/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups with molecular oxygen only
- C07C29/52—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups with molecular oxygen only in the presence of mineral boron compounds with, when necessary, hydrolysis of the intermediate formed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/04—Esters of boric acids
-
- 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
<FORM:1027005/C2/1> A process of producing a cycloalkanol and a borate ester thereof and cycloalkanone from the corresponding cycloalkane comprises heating the cycloalkane with molecular oxygen at an elevated temperature in the presence of a boron compound capable of esterifying the cycloalkanol formed and in the presence of a benzene-type compound, e.g. benzene, toluene, or xylene in an amount of from 0.01% to 5% by weight based on the cycloalkane and insufficient to prevent the oxidation, and hydrolysing the borate ester produced to the cyclo-alkanol. An initiator for the oxidation reaction may be introduced into the mixture such as di-tertiary-butyl peroxide, methylethylketone peroxide, tertiary-butyl hydroperoxide, acetaldehyde or cyclohexanone or a mixture of two or more may be used. The cycloalkane may be produced by hydrogenating a benzene-type compound with hydrogen to produce a mixture of cycloalkane with a proportion of unreacted benzene-type compound in the range of 0.01 to 5% by weight based on the cycloalkane. As shown benzene and cyclohexane are introduced into the hydrogenation zone 1 through lines 4 and 5, respectively and a purge stream containing primarily cyclohexane and 0.56% of benzene is recycled to the hydrogenation zone through line 6 hydrogen being introduced into the reactor through line 7. The effluent from the hydrogenation zone consisting substantially of cyclohexane and 0.05% by weight of benzene passes through line 8, is combined with the cyclohexane recycle stream 9, and enters the oxidation reactor 2. The recycle stream 9 and the reactor effluent from line 8 are proportioned so as to result in a cyclohexane feed to the oxidation reaction containing 0.5% by weight of benzene. The oxidation is carried out in the presence of metaboric acid. A stream containing 8% oxygen and 92% nitrogen is introduced into the oxidation reactor through line 10. An effluent is withdrawn from the oxidation reactor 2 through line 11 and passed to a cyclohexane recovery tower 3. The unreacted cyclohexane, containing about 0.56% benzene, is removed through line 9 and recycled as previously indicated. The reaction mixture consisting primarily of borate esters of cyclohexanol is removed through line 12, hydrolysed and cyclohexanol and cyclohexanone are recovered by the process described in Specifications 996,792 and 996,791. Specific examples are given in which a mixture of cyclohexane, metaboric acid and benzene with or without an initiator is oxidized to give cyclohexanol and cyclohexanone and comparisons are shown of the effects of differing amounts of benzene present on the amount of the final products.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15480261A | 1961-11-24 | 1961-11-24 | |
| US208133A US3239552A (en) | 1962-07-06 | 1962-07-06 | Process of preparing borate esters of cycloalkanols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SE331837B true SE331837B (en) | 1971-01-18 |
Family
ID=26851791
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE07555/63A SE331837B (en) | 1961-11-24 | 1963-07-08 |
Country Status (7)
| Country | Link |
|---|---|
| CH (1) | CH462801A (en) |
| DE (1) | DE1300938C2 (en) |
| GB (1) | GB1027005A (en) |
| LU (1) | LU43996A1 (en) |
| NL (1) | NL285860A (en) |
| NO (1) | NO118432B (en) |
| SE (1) | SE331837B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112742367B (en) * | 2019-10-29 | 2023-07-11 | 中国石油化工股份有限公司 | Method for catalytic oxidation of cycloalkane |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2931834A (en) * | 1960-04-05 | Ctclohexane oxidation process | ||
| US1947989A (en) * | 1928-06-20 | 1934-02-20 | Firm A Riebeck Sche Montanwerk | Method of oxidizing hydrocarbons |
| US2931501A (en) * | 1953-10-01 | 1960-04-05 | Archer Daniels Midland Co | Hydraulic flotation system |
| DE1046610B (en) * | 1955-06-15 | 1958-12-18 | Basf Ag | Process for the production of cyclohexanol and cyclohexanone by oxidation of cyclohexane |
| DE1158963B (en) * | 1961-01-31 | 1963-12-12 | Halcon International Inc | Process for the oxidation of saturated hydrocarbons |
-
0
- NL NL285860D patent/NL285860A/xx unknown
-
1962
- 1962-11-24 DE DE1962S0082569 patent/DE1300938C2/en not_active Expired
- 1962-11-26 GB GB44580/62A patent/GB1027005A/en not_active Expired
-
1963
- 1963-07-02 LU LU43996D patent/LU43996A1/xx unknown
- 1963-07-05 CH CH843463A patent/CH462801A/en unknown
- 1963-07-05 NO NO149300A patent/NO118432B/no unknown
- 1963-07-08 SE SE07555/63A patent/SE331837B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1027005A (en) | 1966-04-20 |
| LU43996A1 (en) | 1963-09-03 |
| DE1300938B (en) | 1969-08-14 |
| CH462801A (en) | 1968-09-30 |
| DE1300938C2 (en) | 1974-02-07 |
| NO118432B (en) | 1969-12-29 |
| NL285860A (en) |
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