DE1668222A1 - Verfahren zur Oxydation von Kohlenwasserstoffen - Google Patents
Verfahren zur Oxydation von KohlenwasserstoffenInfo
- Publication number
- DE1668222A1 DE1668222A1 DE19671668222 DE1668222A DE1668222A1 DE 1668222 A1 DE1668222 A1 DE 1668222A1 DE 19671668222 DE19671668222 DE 19671668222 DE 1668222 A DE1668222 A DE 1668222A DE 1668222 A1 DE1668222 A1 DE 1668222A1
- Authority
- DE
- Germany
- Prior art keywords
- oxidation
- hydrocarbon
- boron
- reactor
- per
- 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
- 229930195733 hydrocarbon Natural products 0.000 title claims description 63
- 150000002430 hydrocarbons Chemical class 0.000 title claims description 62
- 238000007254 oxidation reaction Methods 0.000 title claims description 55
- 230000003647 oxidation Effects 0.000 title claims description 53
- 238000000034 method Methods 0.000 title claims description 16
- 239000004215 Carbon black (E152) Substances 0.000 claims description 50
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 49
- 229910052796 boron Inorganic materials 0.000 claims description 49
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 26
- 239000011541 reaction mixture Substances 0.000 claims description 18
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 239000003208 petroleum Substances 0.000 claims description 4
- 239000007790 solid phase Substances 0.000 claims description 4
- DDTBPAQBQHZRDW-UHFFFAOYSA-N cyclododecane Chemical compound C1CCCCCCCCCCC1 DDTBPAQBQHZRDW-UHFFFAOYSA-N 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 239000000654 additive Substances 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 20
- 230000000996 additive effect Effects 0.000 description 18
- 239000000203 mixture Substances 0.000 description 11
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 9
- 235000010338 boric acid Nutrition 0.000 description 9
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 9
- VGTPKLINSHNZRD-UHFFFAOYSA-N oxoborinic acid Chemical compound OB=O VGTPKLINSHNZRD-UHFFFAOYSA-N 0.000 description 9
- 229960002645 boric acid Drugs 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 6
- 239000004327 boric acid Substances 0.000 description 6
- -1 boric acid ester Chemical class 0.000 description 6
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 5
- 229910001882 dioxygen Inorganic materials 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 150000001639 boron compounds Chemical class 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000004064 recycling Methods 0.000 description 3
- 229930195734 saturated hydrocarbon Natural products 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 125000005619 boric acid group Chemical class 0.000 description 2
- 150000001642 boronic acid derivatives Chemical class 0.000 description 2
- 239000003245 coal Substances 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- CBFCDTFDPHXCNY-UHFFFAOYSA-N icosane Chemical compound CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- JMMZCWZIJXAGKW-UHFFFAOYSA-N 2-methylpent-2-ene Chemical compound CCC=C(C)C JMMZCWZIJXAGKW-UHFFFAOYSA-N 0.000 description 1
- 101100129922 Caenorhabditis elegans pig-1 gene Proteins 0.000 description 1
- 101100520057 Drosophila melanogaster Pig1 gene Proteins 0.000 description 1
- 235000008694 Humulus lupulus Nutrition 0.000 description 1
- 244000025221 Humulus lupulus Species 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- 241000283986 Lepus Species 0.000 description 1
- PFRUBEOIWWEFOL-UHFFFAOYSA-N [N].[S] Chemical compound [N].[S] PFRUBEOIWWEFOL-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 238000003287 bathing Methods 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 150000001934 cyclohexanes Chemical class 0.000 description 1
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 1
- 239000004914 cyclooctane Substances 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- AZHSSKPUVBVXLK-UHFFFAOYSA-N ethane-1,1-diol Chemical compound CC(O)O AZHSSKPUVBVXLK-UHFFFAOYSA-N 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000008040 ionic compounds Chemical class 0.000 description 1
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 238000006213 oxygenation reaction Methods 0.000 description 1
- 150000004977 peroxyborates Chemical class 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
- C07C2601/20—Systems containing only non-condensed rings with a ring being at least seven-membered the ring being twelve-membered
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US59661466A | 1966-11-23 | 1966-11-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1668222A1 true DE1668222A1 (de) | 1971-09-09 |
Family
ID=24387992
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19671668222 Pending DE1668222A1 (de) | 1966-11-23 | 1967-11-23 | Verfahren zur Oxydation von Kohlenwasserstoffen |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3488740A (enExample) |
| JP (1) | JPS5239023B1 (enExample) |
| BE (1) | BE706822A (enExample) |
| CH (1) | CH478736A (enExample) |
| DE (1) | DE1668222A1 (enExample) |
| ES (1) | ES347523A1 (enExample) |
| FR (1) | FR1554787A (enExample) |
| GB (1) | GB1210673A (enExample) |
| IL (1) | IL28998A (enExample) |
| LU (1) | LU54918A1 (enExample) |
| NL (1) | NL6715611A (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2044461C3 (de) * | 1970-09-08 | 1985-10-24 | Furman, Mendel Simchovič, Moskva | Verfahren zur mehrstufigen Oxydation von Cyclohexan |
| US3932513A (en) * | 1971-02-05 | 1976-01-13 | Halcon International, Inc. | Cyclohexane oxidation |
| DE19848730A1 (de) | 1998-10-22 | 2000-04-27 | Degussa | Verfahren zur Herstellung cyclischer Alkohole |
| JP5526555B2 (ja) * | 2009-02-12 | 2014-06-18 | 住友化学株式会社 | シクロアルカノール及び／又はシクロアルカノンの製造方法 |
| US10479748B2 (en) | 2017-11-30 | 2019-11-19 | Cambridge Enterprise Limited | Oxidation of C1-9-alkanes |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1947989A (en) * | 1928-06-20 | 1934-02-20 | Firm A Riebeck Sche Montanwerk | Method of oxidizing hydrocarbons |
| US3317581A (en) * | 1964-01-17 | 1967-05-02 | Halcon International Inc | Hydrocarbon oxidation process to produce borate ester |
-
1966
- 1966-11-23 US US596614A patent/US3488740A/en not_active Expired - Lifetime
-
1967
- 1967-11-16 NL NL6715611A patent/NL6715611A/xx unknown
- 1967-11-20 GB GB52594/67A patent/GB1210673A/en not_active Expired
- 1967-11-21 LU LU54918D patent/LU54918A1/xx unknown
- 1967-11-21 BE BE706822D patent/BE706822A/xx not_active IP Right Cessation
- 1967-11-22 FR FR1554787D patent/FR1554787A/fr not_active Expired
- 1967-11-22 CH CH1639667A patent/CH478736A/fr not_active IP Right Cessation
- 1967-11-22 IL IL28998A patent/IL28998A/en unknown
- 1967-11-22 JP JP42074826A patent/JPS5239023B1/ja active Pending
- 1967-11-23 ES ES347523A patent/ES347523A1/es not_active Expired
- 1967-11-23 DE DE19671668222 patent/DE1668222A1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| BE706822A (fr) | 1968-05-21 |
| NL6715611A (enExample) | 1968-05-24 |
| ES347523A1 (es) | 1969-02-01 |
| FR1554787A (enExample) | 1969-01-24 |
| GB1210673A (en) | 1970-10-28 |
| LU54918A1 (enExample) | 1969-07-07 |
| IL28998A (en) | 1971-07-28 |
| JPS5239023B1 (enExample) | 1977-10-03 |
| US3488740A (en) | 1970-01-06 |
| CH478736A (fr) | 1969-09-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |