DE3116779A1 - Verfahren zur herstellung von alkoholen und aethern - Google Patents
Verfahren zur herstellung von alkoholen und aethernInfo
- Publication number
- DE3116779A1 DE3116779A1 DE19813116779 DE3116779A DE3116779A1 DE 3116779 A1 DE3116779 A1 DE 3116779A1 DE 19813116779 DE19813116779 DE 19813116779 DE 3116779 A DE3116779 A DE 3116779A DE 3116779 A1 DE3116779 A1 DE 3116779A1
- Authority
- DE
- Germany
- Prior art keywords
- isobutene
- alcohol
- butyl
- mixture
- water
- 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.)
- Withdrawn
Links
- 150000001298 alcohols Chemical class 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 150000002170 ethers Chemical class 0.000 title claims description 5
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims abstract description 200
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract description 193
- 239000000203 mixture Substances 0.000 claims abstract description 99
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 68
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 51
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 50
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims abstract description 50
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims abstract description 48
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 claims abstract description 40
- 238000000034 method Methods 0.000 claims abstract description 38
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000001273 butane Substances 0.000 claims abstract description 25
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000001294 propane Substances 0.000 claims abstract description 24
- HNFSPSWQNZVCTB-UHFFFAOYSA-N 2-methyl-2-propan-2-yloxypropane Chemical compound CC(C)OC(C)(C)C HNFSPSWQNZVCTB-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000001282 iso-butane Substances 0.000 claims abstract description 20
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 61
- 238000006266 etherification reaction Methods 0.000 claims description 42
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 38
- 239000003054 catalyst Substances 0.000 claims description 34
- LRHPLDYGYMQRHN-UHFFFAOYSA-N butyl alcohol Substances CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 31
- 238000006703 hydration reaction Methods 0.000 claims description 30
- 230000036571 hydration Effects 0.000 claims description 28
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 27
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 26
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 26
- 238000000605 extraction Methods 0.000 claims description 26
- 239000011541 reaction mixture Substances 0.000 claims description 24
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 21
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 19
- 230000002378 acidificating effect Effects 0.000 claims description 16
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 8
- XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 claims description 8
- 238000006317 isomerization reaction Methods 0.000 claims description 7
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 claims description 7
- 239000008346 aqueous phase Substances 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 238000002407 reforming Methods 0.000 claims description 3
- 239000002994 raw material Substances 0.000 claims description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 2
- FBCWFOLOHWOWFX-UHFFFAOYSA-N 2-methoxy-2-methylpropane;hydrate Chemical compound O.COC(C)(C)C FBCWFOLOHWOWFX-UHFFFAOYSA-N 0.000 claims 1
- 239000006071 cream Substances 0.000 claims 1
- 238000004064 recycling Methods 0.000 abstract description 3
- 238000004821 distillation Methods 0.000 description 27
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical class CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 23
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 18
- 235000013844 butane Nutrition 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 235000013847 iso-butane Nutrition 0.000 description 14
- 239000012074 organic phase Substances 0.000 description 14
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 10
- 239000012071 phase Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- 238000000926 separation method Methods 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 150000002500 ions Chemical class 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 6
- -1 alcohols Ethers Chemical class 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- 239000003456 ion exchange resin Substances 0.000 description 5
- 229920003303 ion-exchange polymer Polymers 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- WMZNUJPPIPVIOD-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxy]butane Chemical compound CCC(C)OC(C)(C)C WMZNUJPPIPVIOD-UHFFFAOYSA-N 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- SUAICDWVYXQSNC-UHFFFAOYSA-N butane;2-methylpropane Chemical compound CCCC.CC(C)C SUAICDWVYXQSNC-UHFFFAOYSA-N 0.000 description 3
- 238000007036 catalytic synthesis reaction Methods 0.000 description 3
- 239000010779 crude oil Substances 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- RGYAVZGBAJFMIZ-UHFFFAOYSA-N 2,3-dimethylhex-2-ene Chemical compound CCCC(C)=C(C)C RGYAVZGBAJFMIZ-UHFFFAOYSA-N 0.000 description 2
- HHBZZTKMMLDNDN-UHFFFAOYSA-N 2-butan-2-yloxybutane Chemical compound CCC(C)OC(C)CC HHBZZTKMMLDNDN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- 239000003729 cation exchange resin Substances 0.000 description 2
- 229940023913 cation exchange resins Drugs 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000013505 freshwater Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- JSSLNEAEZRGSKN-UHFFFAOYSA-N 2-methylpropane Chemical compound CC(C)C.CC(C)C JSSLNEAEZRGSKN-UHFFFAOYSA-N 0.000 description 1
- 229910018516 Al—O Inorganic materials 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 101100230509 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) hat-1 gene Proteins 0.000 description 1
- 240000007673 Origanum vulgare Species 0.000 description 1
- 241000579467 Rhacophorus hui Species 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- KTUQUZJOVNIKNZ-UHFFFAOYSA-N butan-1-ol;hydrate Chemical compound O.CCCCO KTUQUZJOVNIKNZ-UHFFFAOYSA-N 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 description 1
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- YKWNUSJLICDQEO-UHFFFAOYSA-N ethoxyethane;propan-2-ol Chemical compound CC(C)O.CCOCC YKWNUSJLICDQEO-UHFFFAOYSA-N 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- ONSIBMFFLJKTPT-UHFFFAOYSA-L zinc;2,3,4,5,6-pentachlorobenzenethiolate Chemical compound [Zn+2].[S-]C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl.[S-]C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl ONSIBMFFLJKTPT-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/05—Preparation of ethers by addition of compounds to unsaturated compounds
- C07C41/06—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only
-
- 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
- C07C29/03—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2
- C07C29/04—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2 by hydration of carbon-to-carbon double bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/02—Monohydroxylic acyclic alcohols
- C07C31/10—Monohydroxylic acyclic alcohols containing three carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/02—Monohydroxylic acyclic alcohols
- C07C31/12—Monohydroxylic acyclic alcohols containing four carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Priority Applications (20)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813152586 DE3152586A1 (de) | 1981-04-28 | 1981-04-28 | Verfahren zur herstellung von alkoholen und aethern |
| DE19813116779 DE3116779A1 (de) | 1981-04-28 | 1981-04-28 | Verfahren zur herstellung von alkoholen und aethern |
| CA000399998A CA1189876A (en) | 1981-04-28 | 1982-03-31 | Process for producing alcohols and ethers |
| ES511660A ES511660A0 (es) | 1981-04-28 | 1982-04-23 | Procedimiento para la obtencion de alcoholes y eteres. |
| AT82103533T ATE11034T1 (de) | 1981-04-28 | 1982-04-27 | Verfahren zur herstellung von alkoholen und aethern. |
| DE8282103533T DE3261748D1 (en) | 1981-04-28 | 1982-04-27 | Process for the production of alcohols and ethers |
| AT82103530T ATE11033T1 (de) | 1981-04-28 | 1982-04-27 | Verfahren zur herstellung von gemischen aus isopropyl-tert.-butylether und tert.butylalkohol. |
| DE8282103530T DE3261746D1 (en) | 1981-04-28 | 1982-04-27 | Process for the production of mixtures containing isopropyl-tert.-butyl ether and tert.-butyl alcohol |
| FI821453A FI78899C (fi) | 1981-04-28 | 1982-04-27 | Foerfarande foer framstaellning av en blandning av isopropyl-tert-butyleter och tert-butylalkohol. |
| JP57069737A JPS57188531A (en) | 1981-04-28 | 1982-04-27 | Manufacture of alcohol and ether |
| EP82103530A EP0063813B1 (de) | 1981-04-28 | 1982-04-27 | Verfahren zur Herstellung von Gemischen aus Isopropyl-tert.-butylether und tert.-Butylalkohol |
| NO821385A NO155131C (no) | 1981-04-28 | 1982-04-27 | Fremgangsmaate til fremstilling av blandinger av isopropyl-tert.-butyleter og tert.-butylalkohol. |
| ZA822877A ZA822877B (en) | 1981-04-28 | 1982-04-27 | Process for producing alcohols and ethers |
| EP82103533A EP0063815B1 (de) | 1981-04-28 | 1982-04-27 | Verfahren zur Herstellung von Alkoholen und Äthern |
| US06/372,804 US4393250A (en) | 1981-04-28 | 1982-04-28 | Process for producing alcohols and ethers |
| MX192472A MX158767A (es) | 1981-04-28 | 1982-04-28 | Procedimiento para la preparacion de isopropanol e isopropil butileter-terciario |
| NO861343A NO162855C (no) | 1981-04-28 | 1986-04-07 | Fremgansmaate til fremstilling av alkoholer og etere. |
| FI873493A FI78676C (fi) | 1981-04-28 | 1987-08-12 | Foerfarande foer framstaellning av blandningar innehaollande isopropyl-tert-butyleter och sek-butyl-tert-butyleter. |
| JP3098940A JPH04234826A (ja) | 1981-04-28 | 1991-04-30 | アルコールおよびエーテルの製造方法 |
| JP3098939A JPH04234827A (ja) | 1981-04-28 | 1991-04-30 | アルコールおよびエーテルの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813116779 DE3116779A1 (de) | 1981-04-28 | 1981-04-28 | Verfahren zur herstellung von alkoholen und aethern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3116779A1 true DE3116779A1 (de) | 1982-11-04 |
Family
ID=6130973
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19813116779 Withdrawn DE3116779A1 (de) | 1981-04-28 | 1981-04-28 | Verfahren zur herstellung von alkoholen und aethern |
| DE8282103530T Expired DE3261746D1 (en) | 1981-04-28 | 1982-04-27 | Process for the production of mixtures containing isopropyl-tert.-butyl ether and tert.-butyl alcohol |
| DE8282103533T Expired DE3261748D1 (en) | 1981-04-28 | 1982-04-27 | Process for the production of alcohols and ethers |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8282103530T Expired DE3261746D1 (en) | 1981-04-28 | 1982-04-27 | Process for the production of mixtures containing isopropyl-tert.-butyl ether and tert.-butyl alcohol |
| DE8282103533T Expired DE3261748D1 (en) | 1981-04-28 | 1982-04-27 | Process for the production of alcohols and ethers |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4393250A (en, 2012) |
| EP (2) | EP0063813B1 (en, 2012) |
| JP (3) | JPS57188531A (en, 2012) |
| AT (2) | ATE11033T1 (en, 2012) |
| CA (1) | CA1189876A (en, 2012) |
| DE (3) | DE3116779A1 (en, 2012) |
| ES (1) | ES511660A0 (en, 2012) |
| FI (1) | FI78899C (en, 2012) |
| MX (1) | MX158767A (en, 2012) |
| NO (1) | NO155131C (en, 2012) |
| ZA (1) | ZA822877B (en, 2012) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8606385D0 (en) * | 1986-03-14 | 1986-04-23 | Ici Plc | Gasoline blending components |
| US4731490A (en) * | 1986-07-23 | 1988-03-15 | Arco Chemical Company | Process for methyl, tertiary butyl ether production |
| IT1223016B (it) * | 1987-10-29 | 1990-09-12 | Enichem Anic Spa | Processo per l'idratazione diretta di olefine lineari |
| US4806695A (en) * | 1987-10-30 | 1989-02-21 | Uop Inc. | Process for etherification of a dehydrogenation zone effluent |
| EP0323137A1 (en) * | 1987-12-30 | 1989-07-05 | Mobil Oil Corporation | Process for the production of ethers |
| US5047070A (en) * | 1988-04-11 | 1991-09-10 | Mobil Oil Corporation | Integrated process for production of gasoline and ether from alcohol with feedstock extraction |
| US5011506A (en) * | 1989-09-29 | 1991-04-30 | Mobil Oil Corporation | Integrated etherification and alkene hydration process |
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| US5078751A (en) * | 1990-04-04 | 1992-01-07 | Mobil Oil Corporation | Process for upgrading olefinic gasoline by etherification wherein asymmetrical dialkyl ethers are produced |
| US5154801A (en) * | 1990-05-24 | 1992-10-13 | Mobil Oil Corporation | Advances in product separation in dipe process |
| US5705712A (en) * | 1995-10-05 | 1998-01-06 | Uop | Integrated process for producing diisopropyl ether, an isopropyl tertiary alkyl ether and isopropyl alcohol |
| US5689014A (en) * | 1995-10-05 | 1997-11-18 | Uop | Integrated process for producing diisopropyl ether and an isopropyl tertiary alkyl ether |
| US5750800A (en) * | 1995-11-09 | 1998-05-12 | Uop | Process for producing diisopropyl ether from propane |
| IT1319642B1 (it) * | 2000-11-09 | 2003-10-23 | Snam Progetti | Procedimento per la produzione di idrocarburi altoottanici a partireda miscele n-butano/isobutano quali i butani da campo. |
| DE102004055826A1 (de) * | 2004-11-19 | 2006-05-24 | Basf Ag | Verfahren und Vorrichtung zur Vollhydrierung eines Kohlenwasserstoffstromes |
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| EP3658651B1 (en) | 2017-07-27 | 2025-06-18 | SABIC Global Technologies B.V. | Method of producing a fuel additive |
| SG11202008332SA (en) | 2018-03-19 | 2020-09-29 | Sabic Global Technologies Bv | Method of producing a fuel additive |
| WO2019180585A1 (en) | 2018-03-19 | 2019-09-26 | Sabic Global Technologies B.V. | Method of producing a fuel additive |
| CN111989387B (zh) | 2018-04-19 | 2022-09-06 | 沙特基础工业全球技术有限公司 | 生产燃油添加剂的方法 |
| EP3790854A1 (en) | 2018-05-07 | 2021-03-17 | SABIC Global Technologies B.V. | Method of producing a fuel additive |
| US11414611B2 (en) | 2018-05-07 | 2022-08-16 | Sabic Global Technologies B.V. | Method of producing a fuel additive |
| CN112135809A (zh) | 2018-05-18 | 2020-12-25 | 沙特基础工业全球技术有限公司 | 利用水合单元生产燃料添加剂的方法 |
| US11161796B2 (en) | 2018-09-18 | 2021-11-02 | Sabic Global Technologies B.V. | Systems and processes for efficient production of one or more fuel additives |
| US10995045B2 (en) | 2018-10-09 | 2021-05-04 | Uop Llc | Isomerization zone in alkylate complex |
| US12037313B2 (en) | 2018-11-20 | 2024-07-16 | Sabic Global Technologies B.V. | Process and system for producing ethylene and at least one of butanol and an alkyl tert-butyl ether |
| US12264123B2 (en) | 2019-03-08 | 2025-04-01 | Sabic Global Technologies B.V. | Method of producing a fuel additive |
| WO2022013836A1 (en) * | 2020-07-17 | 2022-01-20 | Sabic Global Technologies B.V. | Removal of c3 lights from lpg feedstock to butane isomerization unit |
| WO2022013840A1 (en) * | 2020-07-17 | 2022-01-20 | Sabic Global Technologies B.V. | C4 feedstock preprocessing for mtbe units and crackers |
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|---|---|---|---|---|
| DE2535471A1 (de) * | 1974-08-30 | 1976-03-11 | Texaco Development Corp | Verfahren zur herstellung von aethern |
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| US3119766A (en) * | 1960-10-10 | 1964-01-28 | Sun Oil Co | Increasing antiknock value of olefinic gasoline |
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| US3849082A (en) * | 1970-06-26 | 1974-11-19 | Chevron Res | Hydrocarbon conversion process |
| BE791661A (fr) * | 1971-11-22 | 1973-05-21 | Sun Oil Co Pennsylvania | Fabrication de composes d'essence contenant du methyl-2-methoxy-2-propane |
| CA958213A (en) * | 1972-04-20 | 1974-11-26 | Maurice Moyle | Gasolines containing dialkyl ether azeotropes |
| US4046520A (en) * | 1972-11-13 | 1977-09-06 | Chevron Research Company | Gasoline production |
| US4252541A (en) * | 1975-11-28 | 1981-02-24 | Texaco Inc. | Method for preparation of ethers |
| DE2646333A1 (de) * | 1976-10-14 | 1978-04-20 | Basf Ag | Verfahren zur herstellung von tertiaeren alkylaethern |
| DE2853769C3 (de) * | 1978-12-13 | 1989-03-16 | Hüls AG, 4370 Marl | Verfahren zur gleichzeitigen Herstellung von reinem Methyl-tert.-butylether und einem C↓4↓-Kohlenwasserstoffgemisch, das wesentlich weniger als 1% Isobuten enthält |
| DE2921576A1 (de) * | 1979-05-28 | 1980-12-04 | Davy International Ag | Verfahren zur herstellung von methyl-tert.-butylaether |
| DE3027965C2 (de) * | 1980-07-24 | 1982-12-30 | Davy McKee AG, 6000 Frankfurt | Verfahren zur Verbesserung der Wärmebilanz bei der Herstellung von Methyl- tert.-butyläther |
-
1981
- 1981-04-28 DE DE19813116779 patent/DE3116779A1/de not_active Withdrawn
-
1982
- 1982-03-31 CA CA000399998A patent/CA1189876A/en not_active Expired
- 1982-04-23 ES ES511660A patent/ES511660A0/es active Granted
- 1982-04-27 FI FI821453A patent/FI78899C/fi not_active IP Right Cessation
- 1982-04-27 ZA ZA822877A patent/ZA822877B/xx unknown
- 1982-04-27 DE DE8282103530T patent/DE3261746D1/de not_active Expired
- 1982-04-27 AT AT82103530T patent/ATE11033T1/de not_active IP Right Cessation
- 1982-04-27 EP EP82103530A patent/EP0063813B1/de not_active Expired
- 1982-04-27 DE DE8282103533T patent/DE3261748D1/de not_active Expired
- 1982-04-27 NO NO821385A patent/NO155131C/no unknown
- 1982-04-27 JP JP57069737A patent/JPS57188531A/ja active Granted
- 1982-04-27 AT AT82103533T patent/ATE11034T1/de not_active IP Right Cessation
- 1982-04-27 EP EP82103533A patent/EP0063815B1/de not_active Expired
- 1982-04-28 MX MX192472A patent/MX158767A/es unknown
- 1982-04-28 US US06/372,804 patent/US4393250A/en not_active Expired - Lifetime
-
1991
- 1991-04-30 JP JP3098940A patent/JPH04234826A/ja active Granted
- 1991-04-30 JP JP3098939A patent/JPH04234827A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2535471A1 (de) * | 1974-08-30 | 1976-03-11 | Texaco Development Corp | Verfahren zur herstellung von aethern |
Non-Patent Citations (1)
| Title |
|---|
| Houben-Weyl: Methoden der organischen Chemie, Bd. 7/3, S. 19 * |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0063813A1 (de) | 1982-11-03 |
| ATE11034T1 (de) | 1985-01-15 |
| ATE11033T1 (de) | 1985-01-15 |
| EP0063813B1 (de) | 1985-01-02 |
| EP0063815B1 (de) | 1985-01-02 |
| JPH0526771B2 (en, 2012) | 1993-04-19 |
| JPH048413B2 (en, 2012) | 1992-02-17 |
| FI821453A0 (fi) | 1982-04-27 |
| JPH04234826A (ja) | 1992-08-24 |
| DE3261748D1 (en) | 1985-02-14 |
| FI821453L (fi) | 1982-10-29 |
| US4393250A (en) | 1983-07-12 |
| MX158767A (es) | 1989-03-13 |
| ZA822877B (en) | 1983-03-30 |
| JPS57188531A (en) | 1982-11-19 |
| JPH0526772B2 (en, 2012) | 1993-04-19 |
| NO155131C (no) | 1987-02-18 |
| FI78899B (fi) | 1989-06-30 |
| DE3261746D1 (en) | 1985-02-14 |
| ES8303273A1 (es) | 1983-02-16 |
| NO155131B (no) | 1986-11-10 |
| CA1189876A (en) | 1985-07-02 |
| NO821385L (no) | 1982-10-29 |
| JPH04234827A (ja) | 1992-08-24 |
| ES511660A0 (es) | 1983-02-16 |
| EP0063815A1 (de) | 1982-11-03 |
| FI78899C (fi) | 1989-10-10 |
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