JPS6348249B2 - - Google Patents
Info
- Publication number
- JPS6348249B2 JPS6348249B2 JP17688280A JP17688280A JPS6348249B2 JP S6348249 B2 JPS6348249 B2 JP S6348249B2 JP 17688280 A JP17688280 A JP 17688280A JP 17688280 A JP17688280 A JP 17688280A JP S6348249 B2 JPS6348249 B2 JP S6348249B2
- Authority
- JP
- Japan
- Prior art keywords
- butene
- reaction
- isobutylene
- column
- fraction
- 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
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 120
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 59
- 229930195733 hydrocarbon Natural products 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 27
- 239000004215 Carbon black (E152) Substances 0.000 claims description 26
- -1 C 4 hydrocarbon Chemical class 0.000 claims description 23
- KOYGZROXUOTUEE-UHFFFAOYSA-N butane;but-1-ene Chemical compound CCCC.CCC=C KOYGZROXUOTUEE-UHFFFAOYSA-N 0.000 claims description 23
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 20
- 239000003054 catalyst Substances 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 230000002378 acidificating effect Effects 0.000 claims description 7
- 239000003208 petroleum Substances 0.000 claims description 7
- 238000005336 cracking Methods 0.000 claims description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 5
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 description 75
- 238000004821 distillation Methods 0.000 description 29
- 239000002994 raw material Substances 0.000 description 17
- 239000012530 fluid Substances 0.000 description 15
- 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 description 14
- 239000007788 liquid Substances 0.000 description 13
- 150000002430 hydrocarbons Chemical class 0.000 description 12
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 10
- 239000003729 cation exchange resin Substances 0.000 description 10
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 239000002245 particle Substances 0.000 description 9
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical class CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- 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
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 239000001282 iso-butane 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
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 4
- 235000013844 butane Nutrition 0.000 description 4
- 239000003456 ion exchange resin Substances 0.000 description 4
- 229920003303 ion-exchange polymer Polymers 0.000 description 4
- 229910052759 nickel Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 4
- WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 239000001273 butane Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000000446 fuel Substances 0.000 description 3
- 238000006317 isomerization reaction Methods 0.000 description 3
- 238000004519 manufacturing process 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
- 239000007787 solid Substances 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
- 229910000990 Ni alloy Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 239000011541 reaction mixture Substances 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 group 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000006757 chemical reactions by type Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000006471 dimerization reaction Methods 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
- 239000007789 gas Substances 0.000 description 1
- 230000000887 hydrating effect Effects 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 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
- 229920001083 polybutene Polymers 0.000 description 1
- 238000011084 recovery Methods 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
- 230000004083 survival effect Effects 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17688280A JPS5799534A (en) | 1980-12-15 | 1980-12-15 | Separating and recovering method of high-purity butene-1 |
| US06/328,317 US4356339A (en) | 1980-12-15 | 1981-12-07 | Process for isolating and recovering butene-1 of high purity |
| GB8136917A GB2092171B (en) | 1980-12-15 | 1981-12-08 | Butene-1 recovery |
| CA000391809A CA1164481A (en) | 1980-12-15 | 1981-12-09 | Process for isolating and recovering butene-1 of high purity |
| DE19813149738 DE3149738A1 (de) | 1980-12-15 | 1981-12-15 | Verfahren zum abtrennen von buten-1 aus butan-buten-fraktionen |
| FR8123402A FR2496096A1 (fr) | 1980-12-15 | 1981-12-15 | Procede pour isoler et recuperer du butene-1 de grande purete |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17688280A JPS5799534A (en) | 1980-12-15 | 1980-12-15 | Separating and recovering method of high-purity butene-1 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5799534A JPS5799534A (en) | 1982-06-21 |
| JPS6348249B2 true JPS6348249B2 (ru) | 1988-09-28 |
Family
ID=16021410
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17688280A Granted JPS5799534A (en) | 1980-12-15 | 1980-12-15 | Separating and recovering method of high-purity butene-1 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5799534A (ru) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5810527A (ja) * | 1981-07-11 | 1983-01-21 | Nippon Oil Co Ltd | 高純度ブテン−１の分離回収方法 |
-
1980
- 1980-12-15 JP JP17688280A patent/JPS5799534A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5799534A (en) | 1982-06-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US7026519B2 (en) | Obtaining tert-butanol | |
| TWI444364B (zh) | 由ｃ烴類的工業混合物製造１-丁烯的方法 | |
| EP0008860B2 (en) | Catalyst system | |
| CN107473917B (zh) | 混合碳四生产二异丁烯的工艺 | |
| GB2092171A (en) | Butene-1 recovery | |
| JPS6250453B2 (ru) | ||
| JP2021031494A (ja) | 最適化蒸留によるオレフィンのオリゴマー化プロセス | |
| TW202028162A (zh) | 以具有降低的烯烴含量的流使烯烴低聚合的方法 | |
| CN107778123B (zh) | 一种制备异丁烯的方法 | |
| JPH08245433A (ja) | ｔ−ブチルアルコールの分解法 | |
| EP0717022B1 (en) | Process for producing isopropyl alcohol by hydrating propylene | |
| JPS6348249B2 (ru) | ||
| JP3344594B2 (ja) | 反応方法 | |
| JPH0136447B2 (ru) | ||
| JPH0257525B2 (ru) | ||
| JPS60204730A (ja) | オレフインとパラフインとからアルキレートを連続的に製造する方法及び装置 | |
| JPS59212438A (ja) | 高純度ブテン−１の分離回収方法 | |
| JPS6363254B2 (ru) | ||
| JPS5951224A (ja) | Ｃ↓４炭化水素留分からイソブチレンを分離する方法 | |
| EP4001248B1 (en) | Olefin trimerization | |
| JPH0216291B2 (ru) | ||
| KR0127863B1 (ko) | 고순도 디이소부텐의 제조방법 | |
| RU2177930C1 (ru) | Способ получения олигомеров алкенов | |
| JPH0245607B2 (ru) | ||
| JPS63197533A (ja) | 接触蒸留用触媒構造物 |