JPH0257525B2 - - Google Patents
Info
- Publication number
- JPH0257525B2 JPH0257525B2 JP57107067A JP10706782A JPH0257525B2 JP H0257525 B2 JPH0257525 B2 JP H0257525B2 JP 57107067 A JP57107067 A JP 57107067A JP 10706782 A JP10706782 A JP 10706782A JP H0257525 B2 JPH0257525 B2 JP H0257525B2
- Authority
- JP
- Japan
- Prior art keywords
- butene
- isobutylene
- reaction
- weight
- butane
- 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 - Lifetime
Links
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 126
- 238000006243 chemical reaction Methods 0.000 claims description 81
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 73
- KOYGZROXUOTUEE-UHFFFAOYSA-N butane;but-1-ene Chemical compound CCCC.CCC=C KOYGZROXUOTUEE-UHFFFAOYSA-N 0.000 claims description 38
- 229930195733 hydrocarbon Natural products 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 32
- 239000004215 Carbon black (E152) Substances 0.000 claims description 23
- 150000002430 hydrocarbons Chemical class 0.000 claims description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 21
- 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 18
- 239000007788 liquid Substances 0.000 claims description 13
- 239000003729 cation exchange resin Substances 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 239000002245 particle Substances 0.000 claims description 10
- 229920000642 polymer Polymers 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 238000004821 distillation Methods 0.000 description 30
- 239000000203 mixture Substances 0.000 description 21
- 239000002994 raw material Substances 0.000 description 19
- 239000003054 catalyst Substances 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 14
- 239000012530 fluid Substances 0.000 description 13
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 12
- -1 containing butene Chemical class 0.000 description 12
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 12
- 238000006116 polymerization reaction Methods 0.000 description 9
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000003456 ion exchange resin Substances 0.000 description 6
- 229920003303 ion-exchange polymer Polymers 0.000 description 6
- 239000001282 iso-butane Substances 0.000 description 6
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 5
- 239000003208 petroleum Substances 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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 3
- 239000001273 butane Substances 0.000 description 3
- 239000000446 fuel Substances 0.000 description 3
- 238000006317 isomerization reaction Methods 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 229940044654 phenolsulfonic acid Drugs 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical group 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RSWGJHLUYNHPMX-UHFFFAOYSA-N 1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid Chemical compound C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006757 chemical reactions by type Methods 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10706782A JPS58225030A (ja) | 1982-06-22 | 1982-06-22 | 高純度ブテン−１の分離回収方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10706782A JPS58225030A (ja) | 1982-06-22 | 1982-06-22 | 高純度ブテン−１の分離回収方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58225030A JPS58225030A (ja) | 1983-12-27 |
| JPH0257525B2 true JPH0257525B2 (US07223432-20070529-C00017.png) | 1990-12-05 |
Family
ID=14449643
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10706782A Granted JPS58225030A (ja) | 1982-06-22 | 1982-06-22 | 高純度ブテン−１の分離回収方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58225030A (US07223432-20070529-C00017.png) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0565029U (ja) * | 1992-02-07 | 1993-08-27 | アイホン株式会社 | スイッチボタン構造 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8067655B2 (en) * | 2008-05-29 | 2011-11-29 | Lyondell Chemical Technology, L.P. | Diisobutylene process |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4215011A (en) * | 1979-02-21 | 1980-07-29 | Chemical Research And Licensing Company | Catalyst system for separating isobutene from C4 streams |
| JPS5675441A (en) * | 1979-11-03 | 1981-06-22 | Erdoelchemie Gmbh | Manufacture of mixture substantially comprising isobutene oligomer and methylltertiaryybutyl ether |
| JPS5742639A (en) * | 1980-08-28 | 1982-03-10 | Toa Nenryo Kogyo Kk | Purification of n-butene |
| JPS5799536A (en) * | 1980-12-15 | 1982-06-21 | Nippon Oil Co Ltd | Purifying and separating method of butene-1 |
-
1982
- 1982-06-22 JP JP10706782A patent/JPS58225030A/ja active Granted
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4215011A (en) * | 1979-02-21 | 1980-07-29 | Chemical Research And Licensing Company | Catalyst system for separating isobutene from C4 streams |
| JPS5675441A (en) * | 1979-11-03 | 1981-06-22 | Erdoelchemie Gmbh | Manufacture of mixture substantially comprising isobutene oligomer and methylltertiaryybutyl ether |
| JPS5742639A (en) * | 1980-08-28 | 1982-03-10 | Toa Nenryo Kogyo Kk | Purification of n-butene |
| JPS5799536A (en) * | 1980-12-15 | 1982-06-21 | Nippon Oil Co Ltd | Purifying and separating method of butene-1 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0565029U (ja) * | 1992-02-07 | 1993-08-27 | アイホン株式会社 | スイッチボタン構造 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58225030A (ja) | 1983-12-27 |
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