IL23279A - Process for the oxidation of hydrocarbons - Google Patents
Process for the oxidation of hydrocarbonsInfo
- Publication number
- IL23279A IL23279A IL23279A IL2327965A IL23279A IL 23279 A IL23279 A IL 23279A IL 23279 A IL23279 A IL 23279A IL 2327965 A IL2327965 A IL 2327965A IL 23279 A IL23279 A IL 23279A
- Authority
- IL
- Israel
- Prior art keywords
- hydrocarbon
- oxidation
- alcohol
- feed
- boric acid
- Prior art date
Links
- 150000002430 hydrocarbons Chemical class 0.000 title claims description 69
- 229930195733 hydrocarbon Natural products 0.000 title claims description 67
- 238000007254 oxidation reaction Methods 0.000 title claims description 39
- 230000003647 oxidation Effects 0.000 title claims description 28
- 238000000034 method Methods 0.000 title claims description 27
- 239000004215 Carbon black (E152) Substances 0.000 claims description 61
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 45
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 25
- 239000011541 reaction mixture Substances 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 16
- 239000004327 boric acid Substances 0.000 claims description 14
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 9
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 7
- 229910001882 dioxygen Inorganic materials 0.000 claims description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 239000007789 gas Substances 0.000 claims description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 6
- 239000002002 slurry Substances 0.000 claims description 5
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims description 4
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 claims description 4
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 3
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical class CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims description 3
- 125000002015 acyclic group Chemical group 0.000 claims description 2
- 239000001273 butane Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 claims description 2
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 claims description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 2
- -1 n-octodecanol Chemical compound 0.000 claims description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 150000001932 cycloheptanes Chemical class 0.000 claims 1
- 150000002334 glycols Chemical class 0.000 claims 1
- 229960004592 isopropanol Drugs 0.000 claims 1
- 229960002645 boric acid Drugs 0.000 description 43
- 235000010338 boric acid Nutrition 0.000 description 43
- 239000007788 liquid Substances 0.000 description 25
- 239000000463 material Substances 0.000 description 24
- 229910052796 boron Inorganic materials 0.000 description 23
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 22
- 239000000203 mixture Substances 0.000 description 17
- 238000010438 heat treatment Methods 0.000 description 16
- 239000006200 vaporizer Substances 0.000 description 13
- 238000006297 dehydration reaction Methods 0.000 description 12
- 208000005156 Dehydration Diseases 0.000 description 11
- 230000018044 dehydration Effects 0.000 description 11
- VGTPKLINSHNZRD-UHFFFAOYSA-N oxoborinic acid Chemical compound OB=O VGTPKLINSHNZRD-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 8
- 229960003903 oxygen Drugs 0.000 description 6
- 230000008021 deposition Effects 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000001638 boron Chemical class 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OPFTUNCRGUEPRZ-QLFBSQMISA-N Cyclohexane Natural products CC(=C)[C@@H]1CC[C@@](C)(C=C)[C@H](C(C)=C)C1 OPFTUNCRGUEPRZ-QLFBSQMISA-N 0.000 description 2
- 238000010923 batch production Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 102000018361 Contactin Human genes 0.000 description 1
- 108060003955 Contactin Proteins 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000005619 boric acid group Chemical group 0.000 description 1
- 150000001639 boron compounds Chemical class 0.000 description 1
- 229910052810 boron oxide Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 150000001924 cycloalkanes Chemical class 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
- 238000010586 diagram Methods 0.000 description 1
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Lubricants (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35722364A | 1964-04-03 | 1964-04-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL23279A true IL23279A (en) | 1969-01-29 |
Family
ID=23404769
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL23279A IL23279A (en) | 1964-04-03 | 1965-04-02 | Process for the oxidation of hydrocarbons |
Country Status (9)
| Country | Link |
|---|---|
| BE (1) | BE661761A (enrdf_load_stackoverflow) |
| CH (1) | CH445486A (enrdf_load_stackoverflow) |
| DE (1) | DE1281443C2 (enrdf_load_stackoverflow) |
| ES (1) | ES311403A1 (enrdf_load_stackoverflow) |
| FR (1) | FR1455077A (enrdf_load_stackoverflow) |
| GB (1) | GB1049846A (enrdf_load_stackoverflow) |
| IL (1) | IL23279A (enrdf_load_stackoverflow) |
| LU (1) | LU48291A1 (enrdf_load_stackoverflow) |
| NO (1) | NO118744B (enrdf_load_stackoverflow) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE634236A (fr) * | 1962-06-28 | 1963-12-27 | Ici Ltd | Perfectionnements aux procédés d'oxydation |
| FR1346607A (fr) * | 1963-01-15 | 1963-12-20 | Stamicarbon | Fabrication d'alcools cycliques |
-
1965
- 1965-03-29 BE BE661761D patent/BE661761A/xx unknown
- 1965-03-30 GB GB13451/65A patent/GB1049846A/en not_active Expired
- 1965-03-31 LU LU48291A patent/LU48291A1/xx unknown
- 1965-04-02 FR FR11668A patent/FR1455077A/fr not_active Expired
- 1965-04-02 IL IL23279A patent/IL23279A/en unknown
- 1965-04-03 NO NO157524A patent/NO118744B/no unknown
- 1965-04-03 ES ES0311403A patent/ES311403A1/es not_active Expired
- 1965-04-03 DE DE1965H0055706 patent/DE1281443C2/de not_active Expired
- 1965-04-05 CH CH467765A patent/CH445486A/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1049846A (en) | 1966-11-30 |
| CH445486A (fr) | 1967-10-31 |
| BE661761A (enrdf_load_stackoverflow) | 1965-09-29 |
| ES311403A1 (es) | 1966-02-16 |
| NO118744B (enrdf_load_stackoverflow) | 1970-02-09 |
| LU48291A1 (enrdf_load_stackoverflow) | 1966-10-01 |
| DE1281443B (de) | 1968-10-31 |
| FR1455077A (fr) | 1966-04-01 |
| DE1281443C2 (de) | 1976-11-04 |
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