CS236879B2 - Processing of ternary butylalkylether and butene-1 - Google Patents
Processing of ternary butylalkylether and butene-1 Download PDFInfo
- Publication number
- CS236879B2 CS236879B2 CS833588A CS358883A CS236879B2 CS 236879 B2 CS236879 B2 CS 236879B2 CS 833588 A CS833588 A CS 833588A CS 358883 A CS358883 A CS 358883A CS 236879 B2 CS236879 B2 CS 236879B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- butene
- tertiary butyl
- carbon atoms
- solvent
- butyl alkyl
- Prior art date
Links
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 title claims description 42
- 229930195733 hydrocarbon Natural products 0.000 claims description 32
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 27
- -1 butyl alkyl ethers Chemical group 0.000 claims description 23
- 239000004215 Carbon black (E152) Substances 0.000 claims description 21
- 150000002430 hydrocarbons Chemical class 0.000 claims description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 12
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 11
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 238000004821 distillation Methods 0.000 claims description 9
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- 238000000895 extractive distillation Methods 0.000 claims description 7
- 238000003786 synthesis reaction Methods 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 238000006317 isomerization reaction Methods 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 claims description 4
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
- 238000005342 ion exchange Methods 0.000 claims description 2
- 239000001282 iso-butane Substances 0.000 claims description 2
- LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 1
- 239000000047 product Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000000926 separation method Methods 0.000 description 5
- 238000000605 extraction Methods 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- YAIQCYZCSGLAAN-UHFFFAOYSA-N [Si+4].[O-2].[Al+3] Chemical compound [Si+4].[O-2].[Al+3] YAIQCYZCSGLAAN-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000004523 catalytic cracking Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/02—Alkenes
- C07C11/08—Alkenes with four carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/05—Preparation of ethers by addition of compounds to unsaturated compounds
- C07C41/06—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/04—Purification; Separation; Use of additives by distillation
- C07C7/05—Purification; Separation; Use of additives by distillation with the aid of auxiliary compounds
- C07C7/08—Purification; Separation; Use of additives by distillation with the aid of auxiliary compounds by extractive distillation
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT21383/82A IT1151182B (it) | 1982-05-20 | 1982-05-20 | Procedimento integrato per la produzione di eteri alchil ter-butilici e butene-1 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS236879B2 true CS236879B2 (en) | 1985-05-15 |
Family
ID=11180958
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS833588A CS236879B2 (en) | 1982-05-20 | 1983-05-20 | Processing of ternary butylalkylether and butene-1 |
Country Status (33)
| Country | Link |
|---|---|
| US (1) | US4513153A (OSRAM) |
| JP (1) | JPS58219127A (OSRAM) |
| KR (1) | KR860001850B1 (OSRAM) |
| AU (1) | AU552855B2 (OSRAM) |
| BE (1) | BE896789A (OSRAM) |
| BG (1) | BG37677A3 (OSRAM) |
| BR (1) | BR8302432A (OSRAM) |
| CA (1) | CA1218386A (OSRAM) |
| CH (1) | CH656119A5 (OSRAM) |
| CS (1) | CS236879B2 (OSRAM) |
| DD (1) | DD209804A5 (OSRAM) |
| DE (1) | DE3318300A1 (OSRAM) |
| DK (1) | DK221583A (OSRAM) |
| EG (1) | EG16041A (OSRAM) |
| ES (1) | ES523005A0 (OSRAM) |
| FR (1) | FR2527201B1 (OSRAM) |
| GB (1) | GB2121791B (OSRAM) |
| GR (1) | GR77461B (OSRAM) |
| IN (1) | IN159787B (OSRAM) |
| IT (1) | IT1151182B (OSRAM) |
| LU (1) | LU84806A1 (OSRAM) |
| MW (1) | MW1983A1 (OSRAM) |
| NL (1) | NL8301820A (OSRAM) |
| NO (1) | NO831758L (OSRAM) |
| NZ (1) | NZ204126A (OSRAM) |
| PH (1) | PH19313A (OSRAM) |
| PL (1) | PL242092A1 (OSRAM) |
| PT (1) | PT76729B (OSRAM) |
| SE (1) | SE8302771L (OSRAM) |
| TR (1) | TR21660A (OSRAM) |
| YU (1) | YU110183A (OSRAM) |
| ZA (1) | ZA833158B (OSRAM) |
| ZW (1) | ZW10383A1 (OSRAM) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4558168A (en) * | 1985-06-19 | 1985-12-10 | Air Products And Chemicals, Inc. | Production of high purity butene-1 from an n-butane feedstock |
| DE3532289A1 (de) * | 1985-09-11 | 1987-03-19 | Krupp Koppers Gmbh | Verfahren zur trennung von paraffinischen und olefinischen c(pfeil abwaerts)4(pfeil abwaerts)-kohlenwasserstoffen |
| US4661209A (en) * | 1986-03-20 | 1987-04-28 | Lloyd Berg | Separation of methyl t-butyl ether from hydrocarbons by extractive distillation |
| US4797133A (en) * | 1986-12-29 | 1989-01-10 | Uop Inc. | Process for recovery of butene-1 from mixed C4 hydrocarbons |
| US5160414A (en) * | 1991-07-19 | 1992-11-03 | Phillips Petroleum Company | Extractive distillation of alcohol/ether/hydrocarbon mixtures |
| US5210327A (en) * | 1992-05-15 | 1993-05-11 | Uop | Etherification with skeletal olefin isomerization |
| US5510561A (en) * | 1992-12-21 | 1996-04-23 | Kerr-Mcgee Chemical Corporation | Homogenous catalyst and processes for fluid phase alkylation |
| US5276212A (en) * | 1992-12-29 | 1994-01-04 | Uop | Etherification with intermediate skeletal olefin isomerization |
| US5300696A (en) * | 1992-12-29 | 1994-04-05 | Uop | C4 rejection for etherification and isomerization process |
| US5228957A (en) * | 1993-01-06 | 1993-07-20 | Lloyd Berg | Separation of methyl T-butyl ether from close boiling C5 hydrocarbons by extractive distillation |
| CA2111018A1 (en) * | 1993-01-06 | 1994-07-07 | Jacob N. Rubin | Integrated mtbe process |
| FR2710907B1 (fr) * | 1993-10-08 | 1996-01-05 | Inst Francais Du Petrole | Procédé de production d'éthers tertiaires à partir d'une charge de craquage catalytique comprenant deux étapes de distillation extractive. |
| IT1270675B (it) | 1994-10-19 | 1997-05-07 | Enichem Spa | Procedimento per la separazione di paraffine in miscela con olefine |
| FR2733978B1 (fr) * | 1995-05-11 | 1997-06-13 | Inst Francais Du Petrole | Procede et installation pour la conversion de coupes c4 et c5 olefiniques en ether et en propylene |
| US6159433A (en) * | 1995-05-11 | 2000-12-12 | Institut Francais Du Petrole | Plant for the conversion of olefinic C4 and C5 cuts to an ether and to propylene |
| IT1276802B1 (it) * | 1995-06-30 | 1997-11-03 | Enichem Spa | Procedimento integrato per la produzione di butene-1 |
| US5750798A (en) * | 1995-12-13 | 1998-05-12 | Phillips Petroleum Company | Method for making ether from a paraffin feedstock |
| FR2761681B1 (fr) * | 1997-04-02 | 1999-05-28 | Inst Francais Du Petrole | Procede de production d'alpha olefine, d'olefine tertiaire et/ou d'ether a partir de coupe hydrocarbonee insaturee |
| FR2761683B1 (fr) * | 1997-04-02 | 1999-05-28 | Inst Francais Du Petrole | Procede de production d'ether et d'olefine a partir de coupe hydrocarbonee contenant au moins une olefine tertiaire par synthese puis decomposition d'ether comportant une premiere etape de purification d'olefine par fractionnement |
| FR2761682B1 (fr) * | 1997-04-02 | 1999-05-28 | Inst Francais Du Petrole | Procede de production d'ether et d'olefine a partir de coupe hydrocarbonee contenant au moins une olefine tertiaire par synthese puis decomposition d'ether comportant une premiere etape de purification d'olefine par lavage a l'eau |
| FR2782996B1 (fr) | 1998-09-09 | 2001-02-02 | Inst Francais Du Petrole | Procede de production d'un diene en trois etapes successives a partir d'un ether alkylique tertiaire |
| US7507868B2 (en) * | 2002-03-29 | 2009-03-24 | Exxonmobil Chemical Patents Inc. | Olefin oligomerization process |
| DE102005062700A1 (de) * | 2005-12-28 | 2007-07-05 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von 1-Buten aus technischen Mischungen von C4-Kohlenwasserstoffen |
| US8946496B2 (en) * | 2011-12-28 | 2015-02-03 | Shell Oil Company | Process for preparing lower olefins from an oxygenate |
| US8889941B2 (en) * | 2011-12-28 | 2014-11-18 | Shell Oil Company | Process for preparing lower olefins from an oxygenate |
| CN103755513B (zh) * | 2013-12-24 | 2016-06-15 | 山东滨州裕华化工厂有限公司 | 一种醚后液化气回收c4工艺 |
| CN103755512B (zh) * | 2013-12-24 | 2016-01-06 | 山东滨州裕华化工厂有限公司 | 醚后液化气分离c4馏分的工艺 |
| BR112019001190B1 (pt) * | 2016-07-28 | 2020-10-20 | Lyondell Chemical Technology, L.P. | processo de produção de 1-buteno e processo para a remoção de parafinas |
| WO2020049463A1 (en) * | 2018-09-07 | 2020-03-12 | Sabic Global Technologies B.V. | Method for the production of mtbe and 1-butene from a c4 feed stream |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2802198A1 (de) * | 1978-01-19 | 1979-07-26 | Basf Ag | Verfahren zur gewinnung von isobuten aus isobuten enthaltenden c tief 4 -kohlenwasserstoffgemischen |
| DE2928509A1 (de) * | 1979-07-14 | 1981-01-29 | Basf Ag | Verfahren zur gemeinsamen herstellung von methyl-tert.-butylaether und gewinnung von isobuten |
| DE3049213A1 (de) * | 1980-12-27 | 1982-07-29 | Basf Ag, 6700 Ludwigshafen | Verfahren zur gemeinsamen herstellung von alkyl-tert.-butylether und gewinnung von butadien |
-
1982
- 1982-05-20 IT IT21383/82A patent/IT1151182B/it active
-
1983
- 1983-05-03 ZA ZA833158A patent/ZA833158B/xx unknown
- 1983-05-03 GR GR71286A patent/GR77461B/el unknown
- 1983-05-03 US US06/491,067 patent/US4513153A/en not_active Expired - Fee Related
- 1983-05-04 ZW ZW103/83A patent/ZW10383A1/xx unknown
- 1983-05-05 AU AU14261/83A patent/AU552855B2/en not_active Ceased
- 1983-05-05 CH CH2756/83A patent/CH656119A5/it not_active IP Right Cessation
- 1983-05-05 NZ NZ204126A patent/NZ204126A/en unknown
- 1983-05-06 BR BR8302432A patent/BR8302432A/pt unknown
- 1983-05-12 GB GB08313099A patent/GB2121791B/en not_active Expired
- 1983-05-13 MW MW19/83A patent/MW1983A1/xx unknown
- 1983-05-13 LU LU84806A patent/LU84806A1/fr unknown
- 1983-05-13 PH PH28895A patent/PH19313A/en unknown
- 1983-05-17 EG EG293/83A patent/EG16041A/xx active
- 1983-05-17 YU YU01101/83A patent/YU110183A/xx unknown
- 1983-05-17 FR FR8308162A patent/FR2527201B1/fr not_active Expired
- 1983-05-17 SE SE8302771A patent/SE8302771L/ not_active Application Discontinuation
- 1983-05-17 KR KR1019830002168A patent/KR860001850B1/ko not_active Expired
- 1983-05-18 TR TR21660A patent/TR21660A/xx unknown
- 1983-05-18 BG BG061011A patent/BG37677A3/xx unknown
- 1983-05-18 NO NO831758A patent/NO831758L/no unknown
- 1983-05-18 DK DK221583A patent/DK221583A/da not_active Application Discontinuation
- 1983-05-19 CA CA000428515A patent/CA1218386A/en not_active Expired
- 1983-05-19 DD DD83251069A patent/DD209804A5/de unknown
- 1983-05-19 BE BE0/210808A patent/BE896789A/fr not_active IP Right Cessation
- 1983-05-19 PT PT76729A patent/PT76729B/pt unknown
- 1983-05-19 DE DE19833318300 patent/DE3318300A1/de not_active Ceased
- 1983-05-20 PL PL24209283A patent/PL242092A1/xx unknown
- 1983-05-20 CS CS833588A patent/CS236879B2/cs unknown
- 1983-05-20 NL NL8301820A patent/NL8301820A/nl not_active Application Discontinuation
- 1983-05-20 IN IN631/CAL/83A patent/IN159787B/en unknown
- 1983-05-20 JP JP58087815A patent/JPS58219127A/ja active Pending
- 1983-05-20 ES ES523005A patent/ES523005A0/es active Granted
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