IL29328A - Recovery of residual product in a hydrocarbon oxidation process in the presence of a boron compound - Google Patents
Recovery of residual product in a hydrocarbon oxidation process in the presence of a boron compoundInfo
- Publication number
- IL29328A IL29328A IL29328A IL2932868A IL29328A IL 29328 A IL29328 A IL 29328A IL 29328 A IL29328 A IL 29328A IL 2932868 A IL2932868 A IL 2932868A IL 29328 A IL29328 A IL 29328A
- Authority
- IL
- Israel
- Prior art keywords
- hydrocarbon
- oxidation
- alcohol
- boron compound
- stripping
- Prior art date
Links
- 238000007254 oxidation reaction Methods 0.000 title claims description 44
- 229930195733 hydrocarbon Natural products 0.000 title claims description 43
- 150000002430 hydrocarbons Chemical class 0.000 title claims description 42
- 230000003647 oxidation Effects 0.000 title claims description 38
- 239000004215 Carbon black (E152) Substances 0.000 title claims description 31
- 150000001639 boron compounds Chemical class 0.000 title claims description 21
- 238000000034 method Methods 0.000 title claims description 20
- 238000011084 recovery Methods 0.000 title description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- 239000008346 aqueous phase Substances 0.000 claims description 13
- 238000004821 distillation Methods 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 10
- 239000012074 organic phase Substances 0.000 claims description 7
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 4
- 229910001882 dioxygen Inorganic materials 0.000 claims description 4
- 150000001642 boronic acid derivatives Chemical class 0.000 claims description 3
- 239000007789 gas Substances 0.000 claims description 3
- VGTPKLINSHNZRD-UHFFFAOYSA-N oxoborinic acid Chemical compound OB=O VGTPKLINSHNZRD-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 241001208007 Procas Species 0.000 claims 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical group OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 claims 1
- 239000000047 product Substances 0.000 description 23
- 229960002645 boric acid Drugs 0.000 description 16
- 235000010338 boric acid Nutrition 0.000 description 16
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 15
- 239000004327 boric acid Substances 0.000 description 15
- -1 cyclo-hexane Chemical class 0.000 description 15
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 14
- 239000012535 impurity Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 7
- 238000010926 purge Methods 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 238000001256 steam distillation Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- CBFCDTFDPHXCNY-UHFFFAOYSA-N icosane Chemical compound CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- QEGNUYASOUJEHD-UHFFFAOYSA-N 1,1-dimethylcyclohexane Chemical class CC1(C)CCCCC1 QEGNUYASOUJEHD-UHFFFAOYSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- 241001292396 Cirrhitidae Species 0.000 description 1
- 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 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000005619 boric acid group Chemical class 0.000 description 1
- 150000001638 boron Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- DDTBPAQBQHZRDW-UHFFFAOYSA-N cyclododecane Chemical compound C1CCCCCCCCCCC1 DDTBPAQBQHZRDW-UHFFFAOYSA-N 0.000 description 1
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical compound O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- YGPDIQIGUHGUIP-UHFFFAOYSA-N cyclohexyloxy(hydroperoxy)borinic acid Chemical compound B(O)(OC1CCCCC1)OO YGPDIQIGUHGUIP-UHFFFAOYSA-N 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
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- FGGJBCRKSVGDPO-UHFFFAOYSA-N hydroperoxycyclohexane Chemical compound OOC1CCCCC1 FGGJBCRKSVGDPO-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000004977 peroxyborates Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000002311 subsequent effect Effects 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- BOOITXALNJLNMB-UHFFFAOYSA-N tricyclohexyl borate Chemical compound C1CCCCC1OB(OC1CCCCC1)OC1CCCCC1 BOOITXALNJLNMB-UHFFFAOYSA-N 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60988167A | 1967-01-17 | 1967-01-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL29328A true IL29328A (en) | 1971-07-28 |
Family
ID=24442732
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL29328A IL29328A (en) | 1967-01-17 | 1968-01-17 | Recovery of residual product in a hydrocarbon oxidation process in the presence of a boron compound |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3592859A (en, 2012) |
| BE (1) | BE709383A (en, 2012) |
| BR (1) | BR6896341D0 (en, 2012) |
| DE (1) | DE1668237A1 (en, 2012) |
| ES (1) | ES349402A1 (en, 2012) |
| FR (1) | FR1548234A (en, 2012) |
| GB (1) | GB1208341A (en, 2012) |
| IL (1) | IL29328A (en, 2012) |
| LU (1) | LU55275A1 (en, 2012) |
| NL (1) | NL6800290A (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4272326A (en) * | 1980-01-24 | 1981-06-09 | Allied Chemical Corporation | Enhanced distillation of cyclohexanol from phenol with additional cyclohexanone feed |
| US10479748B2 (en) | 2017-11-30 | 2019-11-19 | Cambridge Enterprise Limited | Oxidation of C1-9-alkanes |
-
1967
- 1967-01-17 US US609881A patent/US3592859A/en not_active Expired - Lifetime
- 1967-12-29 FR FR1548234D patent/FR1548234A/fr not_active Expired
-
1968
- 1968-01-09 NL NL6800290A patent/NL6800290A/xx unknown
- 1968-01-15 LU LU55275D patent/LU55275A1/xx unknown
- 1968-01-15 BE BE709383D patent/BE709383A/xx unknown
- 1968-01-16 GB GB2411/68A patent/GB1208341A/en not_active Expired
- 1968-01-17 BR BR196341/68A patent/BR6896341D0/pt unknown
- 1968-01-17 IL IL29328A patent/IL29328A/en unknown
- 1968-01-17 DE DE19681668237 patent/DE1668237A1/de active Pending
- 1968-01-17 ES ES349402A patent/ES349402A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR1548234A (en, 2012) | 1968-11-29 |
| ES349402A1 (es) | 1969-04-01 |
| US3592859A (en) | 1971-07-13 |
| DE1668237A1 (de) | 1971-09-30 |
| NL6800290A (en, 2012) | 1968-07-18 |
| GB1208341A (en) | 1970-10-14 |
| LU55275A1 (en, 2012) | 1969-08-12 |
| BR6896341D0 (pt) | 1973-04-05 |
| BE709383A (en, 2012) | 1968-07-15 |
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