DE1568440A1 - Chemisches Verfahren - Google Patents
Chemisches VerfahrenInfo
- Publication number
- DE1568440A1 DE1568440A1 DE19661568440 DE1568440A DE1568440A1 DE 1568440 A1 DE1568440 A1 DE 1568440A1 DE 19661568440 DE19661568440 DE 19661568440 DE 1568440 A DE1568440 A DE 1568440A DE 1568440 A1 DE1568440 A1 DE 1568440A1
- Authority
- DE
- Germany
- Prior art keywords
- alcohols
- alcohol
- ester
- oxidized
- hydrogenated
- 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
- 238000001311 chemical methods and process Methods 0.000 title description 2
- 150000002148 esters Chemical class 0.000 claims description 44
- 150000001298 alcohols Chemical class 0.000 claims description 42
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 25
- 230000003647 oxidation Effects 0.000 claims description 24
- 238000007254 oxidation reaction Methods 0.000 claims description 24
- 238000001179 sorption measurement Methods 0.000 claims description 20
- 238000000605 extraction Methods 0.000 claims description 16
- 229930195733 hydrocarbon Natural products 0.000 claims description 16
- 229910052782 aluminium Inorganic materials 0.000 claims description 15
- 150000002430 hydrocarbons Chemical class 0.000 claims description 14
- 239000004215 Carbon black (E152) Substances 0.000 claims description 13
- -1 alkene hydrocarbon Chemical class 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 9
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 230000001590 oxidative effect Effects 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000012535 impurity Substances 0.000 claims 5
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 4
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 150000002894 organic compounds Chemical class 0.000 claims 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 1
- 239000012431 aqueous reaction media Substances 0.000 claims 1
- 238000003795 desorption Methods 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 71
- 239000000463 material Substances 0.000 description 41
- 238000005984 hydrogenation reaction Methods 0.000 description 31
- 150000001299 aldehydes Chemical class 0.000 description 28
- 239000006227 byproduct Substances 0.000 description 28
- 239000012188 paraffin wax Substances 0.000 description 17
- 239000000047 product Substances 0.000 description 14
- 150000001336 alkenes Chemical class 0.000 description 13
- 238000004821 distillation Methods 0.000 description 13
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 12
- 150000004703 alkoxides Chemical class 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 238000000926 separation method Methods 0.000 description 11
- 238000011084 recovery Methods 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 6
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 6
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 6
- 239000001294 propane Substances 0.000 description 6
- 239000008187 granular material Substances 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 125000005234 alkyl aluminium group Chemical group 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000000295 fuel oil Substances 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical class [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical class [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical class [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000005662 Paraffin oil Substances 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical class [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 239000011651 chromium Chemical class 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- HFJRKMMYBMWEAD-UHFFFAOYSA-N dodecanal Chemical compound CCCCCCCCCCCC=O HFJRKMMYBMWEAD-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 150000003568 thioethers Chemical class 0.000 description 2
- XBEXIHMRFRFRAM-UHFFFAOYSA-N tridodecylalumane Chemical compound CCCCCCCCCCCC[Al](CCCCCCCCCCCC)CCCCCCCCCCCC XBEXIHMRFRFRAM-UHFFFAOYSA-N 0.000 description 2
- 239000011701 zinc Chemical class 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical class [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 101100286286 Dictyostelium discoideum ipi gene Proteins 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Chemical class 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical class [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Chemical class 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- PWGQHOJABIQOOS-UHFFFAOYSA-N copper;dioxido(dioxo)chromium Chemical compound [Cu+2].[O-][Cr]([O-])(=O)=O PWGQHOJABIQOOS-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical class C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Chemical class 0.000 description 1
- BGEHHAVMRVXCGR-UHFFFAOYSA-N methylundecylketone Natural products CCCCCCCCCCCCC=O BGEHHAVMRVXCGR-UHFFFAOYSA-N 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum 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
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000989 no adverse effect Toxicity 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- JVIKNVRZMNQFFL-UHFFFAOYSA-N tri(tetradecyl)alumane Chemical compound CCCCCCCCCCCCCC[Al](CCCCCCCCCCCCCC)CCCCCCCCCCCCCC JVIKNVRZMNQFFL-UHFFFAOYSA-N 0.000 description 1
- NHADXUOUFVKVEB-UHFFFAOYSA-N trihexadecylalumane Chemical compound CCCCCCCCCCCCCCCC[Al](CCCCCCCCCCCCCCCC)CCCCCCCCCCCCCCCC NHADXUOUFVKVEB-UHFFFAOYSA-N 0.000 description 1
- LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-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
- C07C29/54—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 starting from compounds containing carbon-to-metal bonds and followed by conversion of the -O- metal to -OH groups
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 |
|---|---|---|---|
| US428876A US3394195A (en) | 1965-01-28 | 1965-01-28 | Recovery of alcohol from by-products of the oxidation of aluminum alkyls |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1568440A1 true DE1568440A1 (de) | 1970-03-19 |
Family
ID=23700749
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661568440 Pending DE1568440A1 (de) | 1965-01-28 | 1966-01-28 | Chemisches Verfahren |
Country Status (5)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3547969A (en) * | 1968-02-05 | 1970-12-15 | Continental Oil Co | Catalytic hydrogenation of oxidized aluminum trialkyls |
| US3547968A (en) * | 1968-02-05 | 1970-12-15 | Continental Oil Co | Catalytic hydrogenation of oxidized aluminum trialkyls |
| US3898291A (en) * | 1969-11-14 | 1975-08-05 | Celanese Canada Ltd | Separation of ethanol and isopropanol by solvent extraction |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2892858A (en) * | 1959-06-30 | Certificate of correction | ||
| US3270065A (en) * | 1966-08-30 | Recovery from metal-free oxygenated alcohol products arising during mod- ified oxidation of aluminum alkyls | ||
| US2621203A (en) * | 1947-10-04 | 1952-12-09 | California Research Corp | Adsorption separation of hydrocarbons and oxygenated organic compounds |
| US2610977A (en) * | 1947-12-06 | 1952-09-16 | Standard Oil Dev Co | Recovery of alcohols from hydrocarbon oils |
| US2596160A (en) * | 1948-01-30 | 1952-05-13 | Kellogg M W Co | Separation of organic compounds |
| US2647139A (en) * | 1948-03-31 | 1953-07-28 | Kellogg M W Co | Separation of organic compounds |
| US2619497A (en) * | 1948-05-06 | 1952-11-25 | Standard Oil Dev Co | Recovery of high boiling alcohols by activated alumina |
| US2653959A (en) * | 1949-03-22 | 1953-09-29 | Texas Co | Process for recovering oxygenated organic compounds |
| US2696304A (en) * | 1949-10-24 | 1954-12-07 | Phillips Petroleum Co | Process for continuous adsorption |
| US2943105A (en) * | 1957-12-23 | 1960-06-28 | Pan American Petroleum Corp | Treatment of hydrocarbon solutions of oxygenated chemicals with solid adsorbents |
| US2918486A (en) * | 1958-05-28 | 1959-12-22 | American Oil Co | Extraction of alcohols with propylene carbonate |
| NL131937C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1960-07-07 | 1900-01-01 |
-
1965
- 1965-01-28 US US428876A patent/US3394195A/en not_active Expired - Lifetime
-
1966
- 1966-01-14 FR FR45921A patent/FR1469267A/fr not_active Expired
- 1966-01-25 JP JP41003902A patent/JPS5115003B1/ja active Pending
- 1966-01-28 DE DE19661568440 patent/DE1568440A1/de active Pending
- 1966-01-28 GB GB3994/66A patent/GB1118493A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US3394195A (en) | 1968-07-23 |
| FR1469267A (fr) | 1967-02-10 |
| JPS5115003B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-05-13 |
| GB1118493A (en) | 1968-07-03 |
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