DE69415460T2 - Verfahren zur Herstellung von tertiären Ethern aus C4 oder C5 Rohstoffen, das extraktive Distillation enthält - Google Patents
Verfahren zur Herstellung von tertiären Ethern aus C4 oder C5 Rohstoffen, das extraktive Distillation enthältInfo
- Publication number
- DE69415460T2 DE69415460T2 DE69415460T DE69415460T DE69415460T2 DE 69415460 T2 DE69415460 T2 DE 69415460T2 DE 69415460 T DE69415460 T DE 69415460T DE 69415460 T DE69415460 T DE 69415460T DE 69415460 T2 DE69415460 T2 DE 69415460T2
- Authority
- DE
- Germany
- Prior art keywords
- zone
- extractive distillation
- process according
- solvent
- alcohol
- 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 - Fee Related
Links
- 238000000895 extractive distillation Methods 0.000 title claims description 47
- 238000000034 method Methods 0.000 title claims description 30
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 150000002170 ethers Chemical group 0.000 title description 8
- 239000002994 raw material Substances 0.000 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 138
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 72
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 46
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 44
- 229930195733 hydrocarbon Natural products 0.000 claims description 36
- 238000006317 isomerization reaction Methods 0.000 claims description 35
- 239000002904 solvent Substances 0.000 claims description 34
- 150000002430 hydrocarbons Chemical class 0.000 claims description 31
- NUMQCACRALPSHD-UHFFFAOYSA-N tert-butyl ethyl ether Chemical compound CCOC(C)(C)C NUMQCACRALPSHD-UHFFFAOYSA-N 0.000 claims description 22
- 238000003786 synthesis reaction Methods 0.000 claims description 21
- 230000015572 biosynthetic process Effects 0.000 claims description 19
- 238000010992 reflux Methods 0.000 claims description 18
- 238000000926 separation method Methods 0.000 claims description 18
- 238000004821 distillation Methods 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 15
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 15
- KFRVYYGHSPLXSZ-UHFFFAOYSA-N 2-ethoxy-2-methylbutane Chemical compound CCOC(C)(C)CC KFRVYYGHSPLXSZ-UHFFFAOYSA-N 0.000 claims description 10
- 238000009835 boiling Methods 0.000 claims description 10
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 10
- 125000001033 ether group Chemical group 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims description 5
- -1 olefin hydrocarbons Chemical group 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
- 238000011084 recovery Methods 0.000 claims description 4
- 239000003125 aqueous solvent Substances 0.000 claims description 3
- 238000006555 catalytic reaction 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
- 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 20
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000004523 catalytic cracking Methods 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 238000004064 recycling Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000006184 cosolvent Substances 0.000 description 4
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical class CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 3
- 239000002826 coolant Substances 0.000 description 3
- 235000013847 iso-butane Nutrition 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000006266 etherification reaction Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 1
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical group CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 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
- 239000011324 bead Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000007036 catalytic synthesis reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000007792 gaseous phase Substances 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 239000007791 liquid phase 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
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 238000002360 preparation method 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
- 239000000126 substance Substances 0.000 description 1
- 238000011144 upstream manufacturing Methods 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 (2)
| Publication Number | Publication Date |
|---|---|
| DE69415460D1 DE69415460D1 (de) | 1999-02-04 |
| DE69415460T2 true DE69415460T2 (de) | 1999-05-12 |
Family
ID=9451730
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69415460T Expired - Fee Related DE69415460T2 (de) | 1993-10-08 | 1994-09-28 | Verfahren zur Herstellung von tertiären Ethern aus C4 oder C5 Rohstoffen, das extraktive Distillation enthält |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US5536887A (enExample) |
| EP (1) | EP0647608B1 (enExample) |
| JP (1) | JPH07149681A (enExample) |
| KR (1) | KR950011388A (enExample) |
| CN (1) | CN1054835C (enExample) |
| CA (1) | CA2117729A1 (enExample) |
| DE (1) | DE69415460T2 (enExample) |
| ES (1) | ES2128525T3 (enExample) |
| FR (1) | FR2710907B1 (enExample) |
| MY (1) | MY111321A (enExample) |
| NO (1) | NO301224B1 (enExample) |
| TW (1) | TW254930B (enExample) |
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 |
| FI101220B (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 |
| KR101804637B1 (ko) | 2014-10-31 | 2018-01-10 | 주식회사 엘지화학 | 증류 장치 |
| WO2016068677A1 (ko) * | 2014-10-31 | 2016-05-06 | 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 |
| IT1151183B (it) * | 1982-05-20 | 1986-12-17 | Snam Progetti | Procedimento per la produzione di eteri alchil ter-butilici |
| IT1151182B (it) * | 1982-05-20 | 1986-12-17 | Anic Spa | Procedimento integrato per la produzione di eteri alchil ter-butilici e butene-1 |
| 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 EP EP94402163A patent/EP0647608B1/fr not_active Expired - Lifetime
- 1994-09-28 ES ES94402163T patent/ES2128525T3/es not_active Expired - Lifetime
- 1994-09-28 DE DE69415460T patent/DE69415460T2/de not_active Expired - Fee Related
- 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 JP JP6243232A patent/JPH07149681A/ja active Pending
- 1994-10-07 KR KR1019940025630A patent/KR950011388A/ko not_active Abandoned
- 1994-10-07 US US08/319,691 patent/US5536887A/en not_active Expired - Fee Related
- 1994-10-07 CA CA002117729A patent/CA2117729A1/fr not_active Abandoned
- 1994-10-08 CN CN94118640A patent/CN1054835C/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| NO943764L (no) | 1995-04-10 |
| US5536887A (en) | 1996-07-16 |
| CN1054835C (zh) | 2000-07-26 |
| CN1107134A (zh) | 1995-08-23 |
| NO943764D0 (no) | 1994-10-06 |
| EP0647608A1 (fr) | 1995-04-12 |
| FR2710907B1 (fr) | 1996-01-05 |
| MY111321A (en) | 1999-10-30 |
| TW254930B (enExample) | 1995-08-21 |
| FR2710907A1 (fr) | 1995-04-14 |
| NO301224B1 (no) | 1997-09-29 |
| JPH07149681A (ja) | 1995-06-13 |
| DE69415460D1 (de) | 1999-02-04 |
| CA2117729A1 (fr) | 1995-04-09 |
| KR950011388A (ko) | 1995-05-15 |
| EP0647608B1 (fr) | 1998-12-23 |
| ES2128525T3 (es) | 1999-05-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |