CA1174696A - Process for the production of lower alcohols - Google Patents
Process for the production of lower alcoholsInfo
- Publication number
- CA1174696A CA1174696A CA000380442A CA380442A CA1174696A CA 1174696 A CA1174696 A CA 1174696A CA 000380442 A CA000380442 A CA 000380442A CA 380442 A CA380442 A CA 380442A CA 1174696 A CA1174696 A CA 1174696A
- Authority
- CA
- Canada
- Prior art keywords
- water
- olefin
- reactor
- reactant
- butene
- 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
- 238000000034 method Methods 0.000 title claims abstract description 36
- 230000008569 process Effects 0.000 title claims abstract description 32
- 238000004519 manufacturing process Methods 0.000 title abstract description 5
- 150000001298 alcohols Chemical class 0.000 title description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 41
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 39
- 150000001336 alkenes Chemical class 0.000 claims abstract description 37
- 239000003054 catalyst Substances 0.000 claims abstract description 25
- 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 abstract description 11
- 230000002378 acidificating effect Effects 0.000 claims abstract description 11
- 239000003729 cation exchange resin Substances 0.000 claims abstract description 10
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims abstract description 7
- -1 aliphatic olefin Chemical class 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- 230000006872 improvement Effects 0.000 claims abstract description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 23
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 23
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 17
- 239000000376 reactant Substances 0.000 claims description 15
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 6
- 238000010924 continuous production Methods 0.000 claims description 5
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 230000036571 hydration Effects 0.000 abstract description 5
- 238000006703 hydration reaction Methods 0.000 abstract description 5
- 238000006243 chemical reaction Methods 0.000 description 27
- 239000000203 mixture Substances 0.000 description 13
- 239000007789 gas Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 238000000079 presaturation Methods 0.000 description 5
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000012495 reaction gas Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000012423 maintenance Methods 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 125000000542 sulfonic acid group Chemical group 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-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 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229940023913 cation exchange resins Drugs 0.000 description 1
- 235000019628 coolness Nutrition 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000007792 gaseous phase Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000009827 uniform distribution 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
- C07C29/03—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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3024146.4 | 1980-06-27 | ||
| DE3024146A DE3024146C2 (de) | 1980-06-27 | 1980-06-27 | Verfahren zur kontinuierlichen Herstellung von Alkoholen mit 3 bis 5 Kohlenstoffatomen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1174696A true CA1174696A (en) | 1984-09-18 |
Family
ID=6105637
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000380442A Expired CA1174696A (en) | 1980-06-27 | 1981-06-23 | Process for the production of lower alcohols |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4456776A (OSRAM) |
| EP (1) | EP0043049B1 (OSRAM) |
| JP (1) | JPS5738731A (OSRAM) |
| AR (1) | AR223927A1 (OSRAM) |
| AT (1) | ATE2665T1 (OSRAM) |
| AU (1) | AU542608B2 (OSRAM) |
| BR (1) | BR8104051A (OSRAM) |
| CA (1) | CA1174696A (OSRAM) |
| CS (1) | CS219860B2 (OSRAM) |
| DD (1) | DD159989A5 (OSRAM) |
| DE (2) | DE3024146C2 (OSRAM) |
| DK (1) | DK281581A (OSRAM) |
| ES (1) | ES503449A0 (OSRAM) |
| FI (1) | FI74700C (OSRAM) |
| IN (1) | IN153745B (OSRAM) |
| MX (1) | MX158341A (OSRAM) |
| NO (1) | NO154834C (OSRAM) |
| PL (1) | PL126065B1 (OSRAM) |
| RO (1) | RO82547A (OSRAM) |
| SU (1) | SU1250167A3 (OSRAM) |
| TR (1) | TR21164A (OSRAM) |
| YU (1) | YU41785B (OSRAM) |
| ZA (1) | ZA813917B (OSRAM) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3419392C1 (de) * | 1984-05-24 | 1985-12-05 | Deutsche Texaco Ag, 2000 Hamburg | Verfahren zur kontinuierlichen Herstellung von Isopropylalkohol oder sek. Butylalkohol |
| US4670612A (en) * | 1985-06-18 | 1987-06-02 | Sumitomo Chemical Company, Limited | Method for producing alicyclic alcohols |
| IT1223016B (it) * | 1987-10-29 | 1990-09-12 | Enichem Anic Spa | Processo per l'idratazione diretta di olefine lineari |
| US4956506A (en) * | 1989-12-21 | 1990-09-11 | Conoco Inc. | Vapor-phase hydration of olefins to alcohols in series reactors with intermediate alcohol removal |
| JPH0733668B2 (ja) * | 1990-03-29 | 1995-04-12 | 株式会社技研製作所 | 鋼管杭圧入機及び鋼管杭圧入方法 |
| JPH0786233B2 (ja) * | 1990-03-29 | 1995-09-20 | 株式会社技研製作所 | 鋼管杭圧入機及びその移動方法 |
| US5268515A (en) * | 1992-05-01 | 1993-12-07 | The Pritchard Corporation | Process of preparing an isopropanol and diisopropyl ether oxgenate motor fuel additive |
| US5191129A (en) * | 1992-05-01 | 1993-03-02 | The Pritchard Corporation | Method of preparing an isopropanol and diisopropyl ether oxygenate motor fuel additive |
| US5488185A (en) * | 1993-09-30 | 1996-01-30 | The Boc Group, Inc. | Process for the production of ethanol and isopropanol |
| US6563006B2 (en) | 2001-04-30 | 2003-05-13 | Melvin K. Carter | Catalytic oxidative conversion of hydrocarbons to aldehydes |
| US7399891B2 (en) | 2005-06-08 | 2008-07-15 | Exxonmobil Chemical Patents Inc. | Process for alcohol production by selective ether decomposition |
| JP5127020B2 (ja) * | 2005-12-01 | 2013-01-23 | Ｊｘ日鉱日石エネルギー株式会社 | オレフィンの水和方法 |
| US8558036B2 (en) | 2010-11-15 | 2013-10-15 | Saudi Arabian Oil Company | Dual phase catalysts system for mixed olefin hydrations |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1210768B (de) * | 1956-09-27 | 1966-02-17 | Exxon Research Engineering Co | Verfahren zur Herstellung von Isopropylalkohol und Diisopropylaether durch Wasseranlagerung an Propylen |
| GB809318A (en) * | 1956-09-27 | 1959-02-18 | Exxon Research Engineering Co | Hydration of propylene |
| DE1249845B (OSRAM) * | 1965-07-24 | |||
| DE2147739A1 (de) * | 1971-09-24 | 1973-04-05 | Texaco Ag | Verfahren zur kontinuierlichen herstellung von niederen alkoholen, insbesondere isopropanol |
| JPS49117412A (OSRAM) * | 1973-02-27 | 1974-11-09 | ||
| 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 |
-
1980
- 1980-06-27 DE DE3024146A patent/DE3024146C2/de not_active Expired
-
1981
- 1981-06-10 ZA ZA00813917A patent/ZA813917B/xx unknown
- 1981-06-10 AR AR285660A patent/AR223927A1/es active
- 1981-06-15 IN IN647/CAL/81A patent/IN153745B/en unknown
- 1981-06-17 FI FI811907A patent/FI74700C/fi not_active IP Right Cessation
- 1981-06-20 DE DE8181104739T patent/DE3160098D1/de not_active Expired
- 1981-06-20 EP EP81104739A patent/EP0043049B1/de not_active Expired
- 1981-06-20 AT AT81104739T patent/ATE2665T1/de not_active IP Right Cessation
- 1981-06-23 NO NO812147A patent/NO154834C/no unknown
- 1981-06-23 CA CA000380442A patent/CA1174696A/en not_active Expired
- 1981-06-24 RO RO81104681A patent/RO82547A/ro unknown
- 1981-06-24 AU AU72116/81A patent/AU542608B2/en not_active Ceased
- 1981-06-25 TR TR21164A patent/TR21164A/xx unknown
- 1981-06-25 DK DK281581A patent/DK281581A/da not_active Application Discontinuation
- 1981-06-25 YU YU1593/81A patent/YU41785B/xx unknown
- 1981-06-25 DD DD81231143A patent/DD159989A5/de not_active IP Right Cessation
- 1981-06-25 CS CS814846A patent/CS219860B2/cs unknown
- 1981-06-26 JP JP9847881A patent/JPS5738731A/ja active Granted
- 1981-06-26 MX MX188026A patent/MX158341A/es unknown
- 1981-06-26 PL PL1981231891A patent/PL126065B1/pl unknown
- 1981-06-26 BR BR8104051A patent/BR8104051A/pt unknown
- 1981-06-26 SU SU813352656A patent/SU1250167A3/ru active
- 1981-06-26 ES ES503449A patent/ES503449A0/es active Granted
-
1983
- 1983-01-13 US US06/457,827 patent/US4456776A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| PL231891A1 (OSRAM) | 1982-02-01 |
| YU41785B (en) | 1987-12-31 |
| AU7211681A (en) | 1982-01-07 |
| ZA813917B (en) | 1982-06-30 |
| DE3024146C2 (de) | 1983-07-21 |
| CS219860B2 (en) | 1983-03-25 |
| EP0043049A1 (de) | 1982-01-06 |
| PL126065B1 (en) | 1983-07-30 |
| DE3160098D1 (en) | 1983-04-07 |
| ATE2665T1 (de) | 1983-03-15 |
| FI74700C (fi) | 1988-03-10 |
| TR21164A (tr) | 1983-11-30 |
| AU542608B2 (en) | 1985-02-28 |
| RO82547B (ro) | 1983-09-30 |
| DK281581A (da) | 1981-12-28 |
| FI74700B (fi) | 1987-11-30 |
| DE3024146A1 (de) | 1982-01-28 |
| FI811907L (fi) | 1981-12-28 |
| NO154834B (no) | 1986-09-22 |
| BR8104051A (pt) | 1982-03-16 |
| AR223927A1 (es) | 1981-09-30 |
| DD159989A5 (de) | 1983-04-20 |
| JPS5738731A (en) | 1982-03-03 |
| ES8204404A1 (es) | 1982-05-16 |
| US4456776A (en) | 1984-06-26 |
| IN153745B (OSRAM) | 1984-08-18 |
| RO82547A (ro) | 1983-10-15 |
| EP0043049B1 (de) | 1983-03-02 |
| NO812147L (no) | 1981-12-28 |
| JPH0251889B2 (OSRAM) | 1990-11-08 |
| MX158341A (es) | 1989-01-26 |
| NO154834C (no) | 1987-01-02 |
| ES503449A0 (es) | 1982-05-16 |
| YU159381A (en) | 1983-02-28 |
| SU1250167A3 (ru) | 1986-08-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |