JPH0137379B2 - - Google Patents
Info
- Publication number
- JPH0137379B2 JPH0137379B2 JP11044079A JP11044079A JPH0137379B2 JP H0137379 B2 JPH0137379 B2 JP H0137379B2 JP 11044079 A JP11044079 A JP 11044079A JP 11044079 A JP11044079 A JP 11044079A JP H0137379 B2 JPH0137379 B2 JP H0137379B2
- Authority
- JP
- Japan
- Prior art keywords
- isobutylene
- water
- sulfone
- tba
- hydrocarbon mixture
- 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
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 47
- 229930195733 hydrocarbon Natural products 0.000 claims description 24
- 239000004215 Carbon black (E152) Substances 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 18
- -1 C 4 hydrocarbon Chemical class 0.000 claims description 13
- 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 9
- 239000003729 cation exchange resin Substances 0.000 claims description 7
- 229920001577 copolymer Polymers 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 235000013844 butane Nutrition 0.000 claims description 5
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical class CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 3
- MBDNRNMVTZADMQ-UHFFFAOYSA-N sulfolene Chemical compound O=S1(=O)CC=CC1 MBDNRNMVTZADMQ-UHFFFAOYSA-N 0.000 claims description 3
- MBDUIEKYVPVZJH-UHFFFAOYSA-N 1-ethylsulfonylethane Chemical group CCS(=O)(=O)CC MBDUIEKYVPVZJH-UHFFFAOYSA-N 0.000 claims description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 description 23
- 150000003457 sulfones Chemical class 0.000 description 19
- 150000002430 hydrocarbons Chemical class 0.000 description 16
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 7
- 230000000887 hydrating effect Effects 0.000 description 5
- 238000006703 hydration reaction Methods 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 3
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 3
- 239000003456 ion exchange resin Substances 0.000 description 3
- 229920003303 ion-exchange polymer Polymers 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 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
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- CKGMDQVIRZYXHU-UHFFFAOYSA-N but-1-ene hydrate Chemical compound O.CCC=C CKGMDQVIRZYXHU-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000006471 dimerization reaction Methods 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 238000007086 side reaction Methods 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
- HQCNSHPBVRWXGH-UHFFFAOYSA-N 2-methylprop-1-ene;hydrate Chemical group O.CC(C)=C HQCNSHPBVRWXGH-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229940023913 cation exchange resins Drugs 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
- 229940005642 polystyrene sulfonic acid Drugs 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000004230 steam cracking Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000000725 suspension Substances 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)
- Catalysts (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11044079A JPS5634643A (en) | 1979-08-31 | 1979-08-31 | Preparation of tertiary butyl alcohol |
| GB8027443A GB2060616B (en) | 1979-08-31 | 1980-08-22 | Process for the production of tertiary butyl alcohol |
| DE19803031702 DE3031702A1 (de) | 1979-08-31 | 1980-08-22 | Verfahren zur herstellung von tert.-butanol |
| CA359,042A CA1129890A (en) | 1979-08-31 | 1980-08-26 | Process for the production of tertiary butyl alcohol |
| FR8018789A FR2464241A1 (fr) | 1979-08-31 | 1980-08-29 | Procede de production d'alcool butylique tertiaire |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11044079A JPS5634643A (en) | 1979-08-31 | 1979-08-31 | Preparation of tertiary butyl alcohol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5634643A JPS5634643A (en) | 1981-04-06 |
| JPH0137379B2 true JPH0137379B2 (cs) | 1989-08-07 |
Family
ID=14535768
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11044079A Granted JPS5634643A (en) | 1979-08-31 | 1979-08-31 | Preparation of tertiary butyl alcohol |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS5634643A (cs) |
| CA (1) | CA1129890A (cs) |
| DE (1) | DE3031702A1 (cs) |
| FR (1) | FR2464241A1 (cs) |
| GB (1) | GB2060616B (cs) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3628008C1 (cs) * | 1986-08-19 | 1987-11-05 | Deutsche Texaco Ag, 2000 Hamburg, De | |
| JPH11193255A (ja) * | 1997-12-26 | 1999-07-21 | Mitsubishi Rayon Co Ltd | 第３級ブチルアルコールの製造方法 |
| TW200514767A (en) * | 2003-08-21 | 2005-05-01 | Mitsubishi Rayon Co | Method of producing tertiary alcohols |
| DE10338581A1 (de) | 2003-08-22 | 2005-03-17 | Oxeno Olefinchemie Gmbh | Verfahren zur Erzeugung von tert.-Butanol |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2297196A1 (fr) * | 1975-01-10 | 1976-08-06 | Chaplits Donat | Procede de separation de l'isobutylene a partir de fractions d'hydrocarbures en c4 |
| GB1518461A (en) * | 1976-05-13 | 1978-07-19 | Shell Int Research | Hydration of unsaturated compounds |
| US4180688A (en) * | 1977-07-29 | 1979-12-25 | Nippon Oil Co., Ltd. | Method for continuously producing tert-butyl alcohol |
| JPS5682580A (en) * | 1979-12-07 | 1981-07-06 | Hitachi Maxell Ltd | Manufacture of button-type battery |
-
1979
- 1979-08-31 JP JP11044079A patent/JPS5634643A/ja active Granted
-
1980
- 1980-08-22 GB GB8027443A patent/GB2060616B/en not_active Expired
- 1980-08-22 DE DE19803031702 patent/DE3031702A1/de not_active Withdrawn
- 1980-08-26 CA CA359,042A patent/CA1129890A/en not_active Expired
- 1980-08-29 FR FR8018789A patent/FR2464241A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| CA1129890A (en) | 1982-08-17 |
| GB2060616A (en) | 1981-05-07 |
| JPS5634643A (en) | 1981-04-06 |
| FR2464241B1 (cs) | 1984-10-19 |
| DE3031702A1 (de) | 1981-03-19 |
| FR2464241A1 (fr) | 1981-03-06 |
| GB2060616B (en) | 1983-10-26 |
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