CN1007345B - 生产异丙醇和具有4至5个碳原子的叔醇类的方法 - Google Patents
生产异丙醇和具有4至5个碳原子的叔醇类的方法Info
- Publication number
- CN1007345B CN1007345B CN87105641A CN87105641A CN1007345B CN 1007345 B CN1007345 B CN 1007345B CN 87105641 A CN87105641 A CN 87105641A CN 87105641 A CN87105641 A CN 87105641A CN 1007345 B CN1007345 B CN 1007345B
- Authority
- CN
- China
- Prior art keywords
- reactor
- water
- hydrocarbon stream
- mole
- reaction
- 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 102
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 title claims abstract description 12
- 150000003509 tertiary alcohols Chemical class 0.000 title claims abstract description 12
- 125000004432 carbon atom Chemical group C* 0.000 title claims abstract description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 76
- 238000006243 chemical reaction Methods 0.000 claims abstract description 56
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 44
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 37
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 36
- 238000004519 manufacturing process Methods 0.000 claims abstract description 12
- 239000007787 solid Substances 0.000 claims abstract description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 43
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 40
- 238000003860 storage Methods 0.000 claims description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 18
- 239000000047 product Substances 0.000 claims description 15
- 239000003729 cation exchange resin Substances 0.000 claims description 14
- 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 13
- 239000002253 acid Substances 0.000 claims description 13
- 238000004821 distillation Methods 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 8
- 239000006227 byproduct Substances 0.000 claims description 7
- 238000007599 discharging Methods 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 238000005516 engineering process Methods 0.000 claims description 4
- 238000001816 cooling 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
- 238000005406 washing Methods 0.000 claims description 2
- 238000010523 cascade reaction Methods 0.000 claims 1
- 239000007788 liquid Substances 0.000 abstract description 39
- 150000001336 alkenes Chemical class 0.000 abstract description 28
- 239000003377 acid catalyst Substances 0.000 abstract description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 38
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 35
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 14
- 239000002904 solvent Substances 0.000 description 12
- 230000009466 transformation Effects 0.000 description 12
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 9
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 8
- 239000001294 propane Substances 0.000 description 7
- 230000002411 adverse Effects 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 230000036571 hydration Effects 0.000 description 6
- 238000006703 hydration reaction Methods 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 4
- 239000001273 butane Substances 0.000 description 4
- 229940023913 cation exchange resins Drugs 0.000 description 4
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000003456 ion exchange resin Substances 0.000 description 3
- 229920003303 ion-exchange polymer Polymers 0.000 description 3
- 238000002386 leaching Methods 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- -1 propylene Virahol Chemical compound 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000010992 reflux 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
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 229920000642 polymer Polymers 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
- 230000003245 working effect Effects 0.000 description 2
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- SILKSEJYECKUJX-UHFFFAOYSA-N C(C)(C)CO.C=CC Chemical compound C(C)(C)CO.C=CC SILKSEJYECKUJX-UHFFFAOYSA-N 0.000 description 1
- 235000003140 Panax quinquefolius Nutrition 0.000 description 1
- 240000005373 Panax quinquefolius Species 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000000712 assembly Effects 0.000 description 1
- 238000000429 assembly Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- OHMBHFSEKCCCBW-UHFFFAOYSA-N hexane-2,5-diol Chemical compound CC(O)CCC(C)O OHMBHFSEKCCCBW-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002184 metal Substances 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
- 230000000737 periodic effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Images
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 (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEP3628008.9-42 | 1986-08-19 | ||
DEP3628007.0 | 1986-08-19 | ||
DE3628008A DE3628008C1 (en, 2012) | 1986-08-19 | 1986-08-19 | |
DEP3628008.9 | 1986-08-19 | ||
DE3628007A DE3628007C1 (en, 2012) | 1986-08-19 | 1986-08-19 | |
DEP3628007.0-42 | 1986-08-19 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN87105641A CN87105641A (zh) | 1988-03-30 |
CN1007345B true CN1007345B (zh) | 1990-03-28 |
Family
ID=25846658
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN87105641A Expired CN1007345B (zh) | 1986-08-19 | 1987-08-18 | 生产异丙醇和具有4至5个碳原子的叔醇类的方法 |
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 |
AU598845B2 (en) | 1990-07-05 |
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 |
NO165723C (no) | 1991-03-27 |
DK429387A (da) | 1988-02-20 |
AU7683487A (en) | 1988-02-25 |
BR8704249A (pt) | 1988-04-12 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C06 | Publication | ||
PB01 | Publication | ||
C13 | Decision | ||
GR02 | Examined patent application | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
C15 | Extension of patent right duration from 15 to 20 years for appl. with date before 31.12.1992 and still valid on 11.12.2001 (patent law change 1993) | ||
OR01 | Other related matters | ||
C19 | Lapse of patent right due to non-payment of the annual fee | ||
CF01 | Termination of patent right due to non-payment of annual fee |