NO301224B1 - Fremgangsmåte for fremstilling av tertiære etere fra C4-C5-hydrokarboner ved to-trinns ekstraktiv destillasjon - Google Patents
Fremgangsmåte for fremstilling av tertiære etere fra C4-C5-hydrokarboner ved to-trinns ekstraktiv destillasjon Download PDFInfo
- Publication number
- NO301224B1 NO301224B1 NO943764A NO943764A NO301224B1 NO 301224 B1 NO301224 B1 NO 301224B1 NO 943764 A NO943764 A NO 943764A NO 943764 A NO943764 A NO 943764A NO 301224 B1 NO301224 B1 NO 301224B1
- Authority
- NO
- Norway
- Prior art keywords
- extractive distillation
- zone
- solvent
- distillate
- hydrocarbons
- Prior art date
Links
- 238000000895 extractive distillation Methods 0.000 title claims description 48
- 229930195733 hydrocarbon Natural products 0.000 title claims description 34
- 150000002430 hydrocarbons Chemical class 0.000 title claims description 31
- 238000004519 manufacturing process Methods 0.000 title claims description 11
- 150000002170 ethers Chemical group 0.000 title description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 135
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 70
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 45
- 238000006317 isomerization reaction Methods 0.000 claims description 35
- 239000002904 solvent Substances 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 28
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical group COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 22
- 238000000926 separation method Methods 0.000 claims description 22
- 239000007858 starting material Substances 0.000 claims description 18
- 238000004821 distillation Methods 0.000 claims description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 14
- 238000010992 reflux Methods 0.000 claims description 14
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 14
- 125000001033 ether group Chemical group 0.000 claims description 10
- 238000004064 recycling Methods 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 238000011084 recovery Methods 0.000 claims description 8
- 239000004215 Carbon black (E152) Substances 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 4
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 claims description 4
- KFRVYYGHSPLXSZ-UHFFFAOYSA-N 2-ethoxy-2-methylbutane Chemical compound CCOC(C)(C)CC KFRVYYGHSPLXSZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000003125 aqueous solvent Substances 0.000 claims description 3
- 238000006555 catalytic reaction Methods 0.000 claims description 3
- 238000000605 extraction Methods 0.000 claims description 3
- HVZJRWJGKQPSFL-UHFFFAOYSA-N tert-Amyl methyl ether Chemical compound CCC(C)(C)OC HVZJRWJGKQPSFL-UHFFFAOYSA-N 0.000 claims description 3
- NUMQCACRALPSHD-UHFFFAOYSA-N tert-butyl ethyl ether Chemical group CCOC(C)(C)C NUMQCACRALPSHD-UHFFFAOYSA-N 0.000 claims description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 claims description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- 229930188620 butyrolactone Natural products 0.000 claims description 2
- LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 claims description 2
- 150000001336 alkenes Chemical class 0.000 description 25
- 238000003786 synthesis reaction Methods 0.000 description 18
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 15
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 8
- 230000003197 catalytic effect Effects 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 3
- 238000004523 catalytic cracking Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 239000002826 coolant Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000006184 cosolvent Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 235000013847 iso-butane Nutrition 0.000 description 2
- MHNNAWXXUZQSNM-UHFFFAOYSA-N methylethylethylene Natural products CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- WWECJGLXBSQKRF-UHFFFAOYSA-N n,n-dimethylformamide;methanol Chemical compound OC.CN(C)C=O WWECJGLXBSQKRF-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- -1 olefin hydrocarbons Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- 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
- C07C41/34—Separation; Purification; Stabilisation; Use of additives
- C07C41/40—Separation; Purification; Stabilisation; Use of additives by change of physical state, e.g. by crystallisation
- C07C41/42—Separation; Purification; Stabilisation; Use of additives by change of physical state, e.g. by crystallisation by distillation
-
- 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
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9312103A FR2710907B1 (fr) | 1993-10-08 | 1993-10-08 | Procédé de production d'éthers tertiaires à partir d'une charge de craquage catalytique comprenant deux étapes de distillation extractive. |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO943764D0 NO943764D0 (no) | 1994-10-06 |
| NO943764L NO943764L (no) | 1995-04-10 |
| NO301224B1 true NO301224B1 (no) | 1997-09-29 |
Family
ID=9451730
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO943764A NO301224B1 (no) | 1993-10-08 | 1994-10-06 | Fremgangsmåte for fremstilling av tertiære etere fra C4-C5-hydrokarboner ved to-trinns ekstraktiv destillasjon |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US5536887A (ko) |
| EP (1) | EP0647608B1 (ko) |
| JP (1) | JPH07149681A (ko) |
| KR (1) | KR950011388A (ko) |
| CN (1) | CN1054835C (ko) |
| CA (1) | CA2117729A1 (ko) |
| DE (1) | DE69415460T2 (ko) |
| ES (1) | ES2128525T3 (ko) |
| FR (1) | FR2710907B1 (ko) |
| MY (1) | MY111321A (ko) |
| NO (1) | NO301224B1 (ko) |
| TW (1) | TW254930B (ko) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2730486B1 (fr) * | 1995-02-15 | 1997-09-05 | Inst Francais Du Petrole | Procede comportant l'etherification optimisee d'une coupe d'hydrocarbures contenant des olefines ayant 6 atomes de carbone par molecule |
| FI101220B1 (fi) * | 1995-12-22 | 1998-05-15 | Neste Oy | Menetelmä alkyylieetterien ja niiden seosten valmistamiseksi |
| US8894820B2 (en) * | 2010-02-05 | 2014-11-25 | Uop Llc | Alkylation apparatus, fractionation zone, and method relating thereto |
| KR101331551B1 (ko) * | 2011-02-22 | 2013-11-20 | 대림산업 주식회사 | 글리콜 모노-터셔리-부틸에테르 화합물의 제조 방법 |
| WO2016068677A1 (ko) * | 2014-10-31 | 2016-05-06 | 주식회사 엘지화학 | 증류 장치 |
| KR101804637B1 (ko) | 2014-10-31 | 2018-01-10 | 주식회사 엘지화학 | 증류 장치 |
| JP6440882B1 (ja) * | 2018-03-30 | 2018-12-19 | 住友化学株式会社 | Ｍｔｂｅの製造装置、イソブチレンの製造装置、ｍｔｂｅの製造方法、及び、イソブチレンの製造方法 |
| EP3604261A1 (de) * | 2018-08-02 | 2020-02-05 | Omv Refining & Marketing Gmbh | Verfahren zur aufreinigung von isobuten aus einem c4-strom und verfahrenstechnische anlage dafür |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2474024A1 (fr) * | 1980-01-23 | 1981-07-24 | Inst Francais Du Petrole | Procede de production de butene-1 a partir d'une coupe c4 d'hydrocarbures |
| FR2520356B1 (fr) * | 1982-01-26 | 1987-09-18 | Inst Francais Du Petrole | Procede de valorisation des coupes c4 olefiniques |
| IT1151182B (it) * | 1982-05-20 | 1986-12-17 | Anic Spa | Procedimento integrato per la produzione di eteri alchil ter-butilici e butene-1 |
| IT1151183B (it) * | 1982-05-20 | 1986-12-17 | Snam Progetti | Procedimento per la produzione di eteri alchil ter-butilici |
| US4398938A (en) * | 1982-05-20 | 1983-08-16 | Velsicol Chemical Corporation | N-Acylated lactams and their herbicidal compositions and method of use |
| FR2614297B1 (fr) * | 1987-04-24 | 1989-07-21 | Inst Francais Du Petrole | Procede de production de methyl-tertiobutyl-ether a partir de n-butenes. |
| US5047070A (en) * | 1988-04-11 | 1991-09-10 | Mobil Oil Corporation | Integrated process for production of gasoline and ether from alcohol with feedstock extraction |
| US5108719A (en) * | 1989-10-24 | 1992-04-28 | Mobil Oil Corporation | Reactor system for ether production |
-
1993
- 1993-10-08 FR FR9312103A patent/FR2710907B1/fr not_active Expired - Fee Related
-
1994
- 1994-09-28 DE DE69415460T patent/DE69415460T2/de not_active Expired - Fee Related
- 1994-09-28 ES ES94402163T patent/ES2128525T3/es not_active Expired - Lifetime
- 1994-09-28 EP EP94402163A patent/EP0647608B1/fr not_active Expired - Lifetime
- 1994-10-04 MY MYPI94002623A patent/MY111321A/en unknown
- 1994-10-05 TW TW083109232A patent/TW254930B/zh active
- 1994-10-06 NO NO943764A patent/NO301224B1/no not_active IP Right Cessation
- 1994-10-07 CA CA002117729A patent/CA2117729A1/fr not_active Abandoned
- 1994-10-07 JP JP6243232A patent/JPH07149681A/ja active Pending
- 1994-10-07 KR KR1019940025630A patent/KR950011388A/ko active IP Right Grant
- 1994-10-07 US US08/319,691 patent/US5536887A/en not_active Expired - Fee Related
- 1994-10-08 CN CN94118640A patent/CN1054835C/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DE69415460T2 (de) | 1999-05-12 |
| EP0647608A1 (fr) | 1995-04-12 |
| FR2710907B1 (fr) | 1996-01-05 |
| JPH07149681A (ja) | 1995-06-13 |
| NO943764D0 (no) | 1994-10-06 |
| TW254930B (ko) | 1995-08-21 |
| US5536887A (en) | 1996-07-16 |
| ES2128525T3 (es) | 1999-05-16 |
| KR950011388A (ko) | 1995-05-15 |
| FR2710907A1 (fr) | 1995-04-14 |
| DE69415460D1 (de) | 1999-02-04 |
| EP0647608B1 (fr) | 1998-12-23 |
| MY111321A (en) | 1999-10-30 |
| CN1054835C (zh) | 2000-07-26 |
| CA2117729A1 (fr) | 1995-04-09 |
| CN1107134A (zh) | 1995-08-23 |
| NO943764L (no) | 1995-04-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2109003C1 (ru) | Способ получения потоков метанола, этанола, н-пропанола и изобутанола для использования, в основном, в получении высокооктановых продуктов, из смесей, содержащих упомянутые спирты, воду и другие низко- и высококипящие соединения | |
| CA1176664A (en) | Process for manufacturing ethylene | |
| US5122236A (en) | Method for removal of dimethyl ether and methanol from c4 hydrocarbon streams | |
| RU2078074C1 (ru) | Способ получения изобутена и алкил-трет-бутилового эфира | |
| GB2043640A (en) | Process for isolating methyl t-butylether from the reaction products of methanol with a c hydrocarbon cut containing isobutene | |
| JPS6366288A (ja) | メタノ−ルをアルキルエ−テルに変換する改良された方法 | |
| JPH0526772B2 (ko) | ||
| NO309522B1 (no) | Fremgangsmåter for fremstilling av dimetyleter, samt utvinning fra metanol | |
| RU2159223C2 (ru) | Способ получения трех отдельных потоков метанола и этанола, н-пропанола и изобутанола | |
| JPS637168B2 (ko) | ||
| RU2167848C2 (ru) | Способ получения эфирного продукта (варианты) | |
| NO301224B1 (no) | Fremgangsmåte for fremstilling av tertiære etere fra C4-C5-hydrokarboner ved to-trinns ekstraktiv destillasjon | |
| KR101499846B1 (ko) | 에틸 t-부틸 에테르를 커플링, 분리 및 순화하는 방법 및 장치 | |
| NO854239L (no) | Kombinasjonsfremgangsmaate med hoey energivirkningsgrad til fremstilling av bensinblandingskomponenter. | |
| NO137823B (no) | Fremgangsm}te til fremstilling av som drivstofftilsetning egnet isopropylalkohol | |
| US5679872A (en) | Process for the purification of an ether comprising two distillation steps | |
| US5237109A (en) | Etherification process | |
| US5015783A (en) | Production of ethers by the reaction of alcohols and olefins | |
| JPH03505588A (ja) | アルコールのエーテル富含ガソリンへの転化 | |
| JPS6133877B2 (ko) | ||
| JPH04225094A (ja) | ガソリンのエーテル化方法 | |
| US9403744B2 (en) | Process for the production of alkyl ethers by the etherification of isobutene | |
| US4808270A (en) | Process and apparatus for the preparation of ether | |
| JPH11511736A (ja) | 第３アルキルエーテルの調製方法 | |
| CA3216101A1 (en) | Process for the separation of a product mixture |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |
Free format text: LAPSED IN APRIL 2003 |