DE1281443C2 - Verfahren zur oxydation von gesaettigten kohlenwasserstoffen mit 4 bis 8 kohlenstoffatomen - Google Patents
Verfahren zur oxydation von gesaettigten kohlenwasserstoffen mit 4 bis 8 kohlenstoffatomenInfo
- Publication number
- DE1281443C2 DE1281443C2 DE1965H0055706 DEH0055706A DE1281443C2 DE 1281443 C2 DE1281443 C2 DE 1281443C2 DE 1965H0055706 DE1965H0055706 DE 1965H0055706 DE H0055706 A DEH0055706 A DE H0055706A DE 1281443 C2 DE1281443 C2 DE 1281443C2
- Authority
- DE
- Germany
- Prior art keywords
- hydrocarbon
- acid
- boron
- alcohol
- oxidation
- 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
- 238000007254 oxidation reaction Methods 0.000 title claims description 20
- 238000000034 method Methods 0.000 title claims description 18
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 title claims 2
- 229930195734 saturated hydrocarbon Natural products 0.000 title description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 47
- 150000002430 hydrocarbons Chemical class 0.000 claims description 47
- 239000004215 Carbon black (E152) Substances 0.000 claims description 39
- 229960002645 boric acid Drugs 0.000 claims description 34
- 235000010338 boric acid Nutrition 0.000 claims description 34
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 33
- 239000000126 substance Substances 0.000 claims description 21
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 19
- 229910052796 boron Inorganic materials 0.000 claims description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 238000006297 dehydration reaction Methods 0.000 claims description 16
- 230000018044 dehydration Effects 0.000 claims description 15
- 230000003647 oxidation Effects 0.000 claims description 15
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 14
- 239000004327 boric acid Substances 0.000 claims description 13
- VGTPKLINSHNZRD-UHFFFAOYSA-N oxoborinic acid Chemical compound OB=O VGTPKLINSHNZRD-UHFFFAOYSA-N 0.000 claims description 12
- 239000011541 reaction mixture Substances 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 9
- 230000008021 deposition Effects 0.000 claims description 5
- 238000001704 evaporation Methods 0.000 claims description 5
- 230000008020 evaporation Effects 0.000 claims description 5
- 230000001590 oxidative effect Effects 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- -1 boric acid ester Chemical class 0.000 claims description 3
- 150000001639 boron compounds Chemical class 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 239000007788 liquid Substances 0.000 description 23
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 239000006200 vaporizer Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- XDVOLDOITVSJGL-UHFFFAOYSA-N 3,7-dihydroxy-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound O1B(O)OB2OB(O)OB1O2 XDVOLDOITVSJGL-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000001638 boron Chemical class 0.000 description 1
- 229910052810 boron oxide Inorganic materials 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 150000001721 carbon Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 150000001934 cyclohexanes Chemical class 0.000 description 1
- ZJOHAJMPXPEIEE-UHFFFAOYSA-N cyclohexanol;hexane Chemical compound CCCCCC.OC1CCCCC1 ZJOHAJMPXPEIEE-UHFFFAOYSA-N 0.000 description 1
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000638 solvent extraction Methods 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)
- Lubricants (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35722364A | 1964-04-03 | 1964-04-03 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1281443B DE1281443B (de) | 1968-10-31 |
| DE1281443C2 true DE1281443C2 (de) | 1976-11-04 |
Family
ID=23404769
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1965H0055706 Expired DE1281443C2 (de) | 1964-04-03 | 1965-04-03 | Verfahren zur oxydation von gesaettigten kohlenwasserstoffen mit 4 bis 8 kohlenstoffatomen |
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 |
| IL23279A (en) | 1969-01-29 |
| 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 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHJ | Ceased/non-payment of the annual fee |