AU598845B2 - Process for the production of isopropanol and tertiary alcohols with 4 to 5 carbon atoms - Google Patents
Process for the production of isopropanol and tertiary alcohols with 4 to 5 carbon atoms Download PDFInfo
- Publication number
- AU598845B2 AU598845B2 AU76834/87A AU7683487A AU598845B2 AU 598845 B2 AU598845 B2 AU 598845B2 AU 76834/87 A AU76834/87 A AU 76834/87A AU 7683487 A AU7683487 A AU 7683487A AU 598845 B2 AU598845 B2 AU 598845B2
- Authority
- AU
- Australia
- Prior art keywords
- reactor
- water
- stream
- alcohol
- sump
- 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.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims description 148
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 title claims description 104
- 238000004519 manufacturing process Methods 0.000 title claims description 19
- 150000003509 tertiary alcohols Chemical class 0.000 title claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 title claims description 11
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 88
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 78
- 238000006243 chemical reaction Methods 0.000 claims description 62
- 229930195733 hydrocarbon Natural products 0.000 claims description 45
- 150000002430 hydrocarbons Chemical class 0.000 claims description 43
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 27
- 239000003054 catalyst Substances 0.000 claims description 21
- 230000002378 acidificating effect Effects 0.000 claims description 19
- 229960004592 isopropanol Drugs 0.000 claims description 18
- 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 claims description 14
- 239000003729 cation exchange resin Substances 0.000 claims description 14
- 239000000047 product Substances 0.000 claims description 12
- 238000004821 distillation Methods 0.000 claims description 10
- 239000006227 byproduct Substances 0.000 claims description 7
- 239000008346 aqueous phase Substances 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 3
- 150000003333 secondary alcohols Chemical class 0.000 claims description 2
- 239000011949 solid catalyst Substances 0.000 claims description 2
- 235000019441 ethanol Nutrition 0.000 claims 3
- 230000000052 comparative effect Effects 0.000 claims 1
- 229960004756 ethanol Drugs 0.000 claims 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 109
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 55
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 30
- 150000001336 alkenes Chemical class 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 16
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 11
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 10
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 239000000463 material Substances 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 7
- 239000001294 propane Substances 0.000 description 7
- 239000012071 phase Substances 0.000 description 6
- -1 Sulfolan Chemical class 0.000 description 5
- 230000036571 hydration Effects 0.000 description 5
- 238000006703 hydration reaction Methods 0.000 description 5
- IRUDSQHLKGNCGF-UHFFFAOYSA-N 2-methylhex-1-ene Chemical class CCCCC(C)=C IRUDSQHLKGNCGF-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 235000013844 butane Nutrition 0.000 description 4
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical class CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000004064 recycling Methods 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- WEERVPDNCOGWJF-UHFFFAOYSA-N 1,4-bis(ethenyl)benzene Chemical compound C=CC1=CC=C(C=C)C=C1 WEERVPDNCOGWJF-UHFFFAOYSA-N 0.000 description 1
- 241001307210 Pene Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229940023913 cation exchange resins Drugs 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 239000007862 dimeric product Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-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
- C07C29/03—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3628007 | 1986-08-19 | ||
| DE3628008A DE3628008C1 (en, 2012) | 1986-08-19 | 1986-08-19 | |
| DE3628008 | 1986-08-19 | ||
| DE3628007A DE3628007C1 (en, 2012) | 1986-08-19 | 1986-08-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU7683487A AU7683487A (en) | 1988-02-25 |
| AU598845B2 true AU598845B2 (en) | 1990-07-05 |
Family
ID=25846658
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU76834/87A Ceased AU598845B2 (en) | 1986-08-19 | 1987-08-13 | Process for the production of isopropanol and tertiary alcohols with 4 to 5 carbon atoms |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP0257511B1 (en, 2012) |
| CN (1) | CN1007345B (en, 2012) |
| AU (1) | AU598845B2 (en, 2012) |
| BR (1) | BR8704249A (en, 2012) |
| DE (1) | DE3766046D1 (en, 2012) |
| DK (1) | DK174479B1 (en, 2012) |
| ES (1) | ES2018514B3 (en, 2012) |
| FI (1) | FI86411C (en, 2012) |
| IN (1) | IN170217B (en, 2012) |
| NO (1) | NO165723C (en, 2012) |
| PL (1) | PL267370A1 (en, 2012) |
| SU (1) | SU1581216A3 (en, 2012) |
| YU (1) | YU152687A (en, 2012) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4956506A (en) * | 1989-12-21 | 1990-09-11 | Conoco Inc. | Vapor-phase hydration of olefins to alcohols in series reactors with intermediate alcohol removal |
| RU2141468C1 (ru) * | 1998-02-19 | 1999-11-20 | Общество с ограниченной ответственностью "НИЦ НХТ" | Способ гидратации алкенов |
| RU2394806C1 (ru) * | 2009-03-05 | 2010-07-20 | Общество с ограниченной ответственностью "Институт по проектированию производств органического синтеза" | Способ получения третичного бутанола |
| RU2455277C2 (ru) * | 2010-05-04 | 2012-07-10 | Общество с ограниченной ответственностью "Научно-производственное объединение ЕВРОХИМ" | Способ получения третичного бутилового спирта |
| RU2485089C2 (ru) * | 2010-05-04 | 2013-06-20 | Общество с ограниченной ответственностью "Еврохим-СПб-Трейдинг" | Способ получения третичного бутилового спирта |
| EP2939995A1 (en) | 2014-04-30 | 2015-11-04 | Sasol Solvents Germany GmbH | Improved water management for the production of isopropyl alcohol by gas phase propylene hydration |
| CN114478185B (zh) * | 2020-10-28 | 2024-02-09 | 中国石油化工股份有限公司 | 一种烯烃水合工艺 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2147739A1 (de) * | 1971-09-24 | 1973-04-05 | Texaco Ag | Verfahren zur kontinuierlichen herstellung von niederen alkoholen, insbesondere isopropanol |
| DE2429770C3 (de) * | 1974-06-21 | 1981-04-16 | Deutsche Texaco Ag, 2000 Hamburg | Verfahren zur Herstellung von niederen Alkoholen durch direkte katalytische Hydratisierung niederer Olefine |
| JPS5610124A (en) * | 1979-07-05 | 1981-02-02 | Sumitomo Chem Co Ltd | Preparation of tert-butyl alcohol |
| US4352945A (en) * | 1981-10-30 | 1982-10-05 | Chevron Research Company | Diisopropyl ether reversion in isopropanol production |
| US4405822A (en) * | 1981-10-30 | 1983-09-20 | Chevron Research Company | Diisopropyl ether hydration in isopropanol production |
| US4469905A (en) * | 1981-11-04 | 1984-09-04 | Union Oil Company Of California | Process for producing and extracting C2 to C6 alcohols |
| DE3419392C1 (de) * | 1984-05-24 | 1985-12-05 | Deutsche Texaco Ag, 2000 Hamburg | Verfahren zur kontinuierlichen Herstellung von Isopropylalkohol oder sek. Butylalkohol |
-
1987
- 1987-08-13 AU AU76834/87A patent/AU598845B2/en not_active Ceased
- 1987-08-17 EP EP87111908A patent/EP0257511B1/de not_active Expired - Lifetime
- 1987-08-17 YU YU01526/87A patent/YU152687A/xx unknown
- 1987-08-17 IN IN592/MAS/87A patent/IN170217B/en unknown
- 1987-08-17 DE DE8787111908T patent/DE3766046D1/de not_active Expired - Lifetime
- 1987-08-17 ES ES87111908T patent/ES2018514B3/es not_active Expired - Lifetime
- 1987-08-18 SU SU874203129A patent/SU1581216A3/ru active
- 1987-08-18 BR BR8704249A patent/BR8704249A/pt unknown
- 1987-08-18 DK DK198704293A patent/DK174479B1/da not_active IP Right Cessation
- 1987-08-18 NO NO873476A patent/NO165723C/no not_active IP Right Cessation
- 1987-08-18 CN CN87105641A patent/CN1007345B/zh not_active Expired
- 1987-08-18 FI FI873568A patent/FI86411C/fi not_active IP Right Cessation
- 1987-08-18 PL PL1987267370A patent/PL267370A1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI86411B (fi) | 1992-05-15 |
| FI873568A0 (fi) | 1987-08-18 |
| NO873476D0 (no) | 1987-08-18 |
| DK429387D0 (da) | 1987-08-18 |
| DE3766046D1 (de) | 1990-12-13 |
| IN170217B (en, 2012) | 1992-02-29 |
| PL267370A1 (en) | 1988-09-01 |
| EP0257511A1 (de) | 1988-03-02 |
| EP0257511B1 (de) | 1990-11-07 |
| YU152687A (en) | 1988-10-31 |
| FI86411C (fi) | 1992-08-25 |
| NO873476L (no) | 1988-02-22 |
| FI873568L (fi) | 1988-02-20 |
| DK174479B1 (da) | 2003-04-14 |
| CN87105641A (zh) | 1988-03-30 |
| SU1581216A3 (ru) | 1990-07-23 |
| NO165723B (no) | 1990-12-17 |
| ES2018514B3 (es) | 1991-04-16 |
| CN1007345B (zh) | 1990-03-28 |
| NO165723C (no) | 1991-03-27 |
| DK429387A (da) | 1988-02-20 |
| AU7683487A (en) | 1988-02-25 |
| BR8704249A (pt) | 1988-04-12 |
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