WO1996001244A1 - Process and apparatus for preparing tertiary alkyl ethers - Google Patents
Process and apparatus for preparing tertiary alkyl ethers Download PDFInfo
- Publication number
- WO1996001244A1 WO1996001244A1 PCT/FI1995/000380 FI9500380W WO9601244A1 WO 1996001244 A1 WO1996001244 A1 WO 1996001244A1 FI 9500380 W FI9500380 W FI 9500380W WO 9601244 A1 WO9601244 A1 WO 9601244A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- column
- reactor
- distillation
- reaction zone
- process according
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 45
- 125000005011 alkyl ether group Chemical group 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 claims abstract description 58
- 238000004821 distillation Methods 0.000 claims abstract description 55
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 20
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 20
- 238000009835 boiling Methods 0.000 claims abstract description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000003054 catalyst Substances 0.000 claims abstract description 15
- 238000006266 etherification reaction Methods 0.000 claims abstract description 13
- 150000005215 alkyl ethers Chemical group 0.000 claims abstract description 11
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 10
- 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 abstract description 8
- 239000003729 cation exchange resin Substances 0.000 claims abstract description 8
- 150000002170 ethers Chemical class 0.000 claims abstract description 7
- 230000003197 catalytic effect Effects 0.000 claims abstract description 5
- 238000010992 reflux Methods 0.000 claims description 13
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 6
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 abstract description 34
- 238000002360 preparation method Methods 0.000 abstract description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 108
- 239000000047 product Substances 0.000 description 25
- HVZJRWJGKQPSFL-UHFFFAOYSA-N tert-Amyl methyl ether Chemical compound CCC(C)(C)OC HVZJRWJGKQPSFL-UHFFFAOYSA-N 0.000 description 21
- MHNNAWXXUZQSNM-UHFFFAOYSA-N methylethylethylene Natural products CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 15
- 239000007788 liquid Substances 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 238000000066 reactive distillation Methods 0.000 description 4
- 238000004523 catalytic cracking Methods 0.000 description 3
- 239000003456 ion exchange resin Substances 0.000 description 3
- 229920003303 ion-exchange polymer Polymers 0.000 description 3
- WGLLSSPDPJPLOR-UHFFFAOYSA-N 2,3-dimethylbut-2-ene Chemical compound CC(C)=C(C)C WGLLSSPDPJPLOR-UHFFFAOYSA-N 0.000 description 2
- KFRVYYGHSPLXSZ-UHFFFAOYSA-N 2-ethoxy-2-methylbutane Chemical compound CCOC(C)(C)CC KFRVYYGHSPLXSZ-UHFFFAOYSA-N 0.000 description 2
- JMMZCWZIJXAGKW-UHFFFAOYSA-N 2-methylpent-2-ene Chemical compound CCC=C(C)C JMMZCWZIJXAGKW-UHFFFAOYSA-N 0.000 description 2
- WWUVJRULCWHUSA-UHFFFAOYSA-N 2MP Natural products CCCC(C)=C WWUVJRULCWHUSA-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229940023913 cation exchange resins Drugs 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- VTPNYMSKBPZSTF-UHFFFAOYSA-N 1-ethenyl-2-ethylbenzene Chemical compound CCC1=CC=CC=C1C=C VTPNYMSKBPZSTF-UHFFFAOYSA-N 0.000 description 1
- VDMXPMYSWFDBJB-UHFFFAOYSA-N 1-ethoxypentane Chemical group CCCCCOCC VDMXPMYSWFDBJB-UHFFFAOYSA-N 0.000 description 1
- WAEOXIOXMKNFLQ-UHFFFAOYSA-N 1-methyl-4-prop-2-enylbenzene Chemical group CC1=CC=C(CC=C)C=C1 WAEOXIOXMKNFLQ-UHFFFAOYSA-N 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- OWWIWYDDISJUMY-UHFFFAOYSA-N 2,3-dimethylbut-1-ene Chemical compound CC(C)C(C)=C OWWIWYDDISJUMY-UHFFFAOYSA-N 0.000 description 1
- LIMAEKMEXJTSNI-UHFFFAOYSA-N 2,3-dimethylpent-1-ene Chemical compound CCC(C)C(C)=C LIMAEKMEXJTSNI-UHFFFAOYSA-N 0.000 description 1
- WFHALSLYRWWUGH-UHFFFAOYSA-N 2,3-dimethylpent-2-ene Chemical compound CCC(C)=C(C)C WFHALSLYRWWUGH-UHFFFAOYSA-N 0.000 description 1
- LXQPBCHJNIOMQU-UHFFFAOYSA-N 2,4-dimethylpent-1-ene Chemical compound CC(C)CC(C)=C LXQPBCHJNIOMQU-UHFFFAOYSA-N 0.000 description 1
- ISRGONDNXBCDBM-UHFFFAOYSA-N 2-chlorostyrene Chemical compound ClC1=CC=CC=C1C=C ISRGONDNXBCDBM-UHFFFAOYSA-N 0.000 description 1
- WYLQOLGJMFRRLX-UHFFFAOYSA-N 2-methoxy-2-methylpentane Chemical compound CCCC(C)(C)OC WYLQOLGJMFRRLX-UHFFFAOYSA-N 0.000 description 1
- BWEKDYGHDCHWEN-UHFFFAOYSA-N 2-methylhex-2-ene Chemical compound CCCC=C(C)C BWEKDYGHDCHWEN-UHFFFAOYSA-N 0.000 description 1
- FHHSSXNRVNXTBG-UHFFFAOYSA-N 3-methylhex-3-ene Chemical compound CCC=C(C)CC FHHSSXNRVNXTBG-UHFFFAOYSA-N 0.000 description 1
- TWCRBBJSQAZZQB-UHFFFAOYSA-N 3-methylidenehexane Chemical compound CCCC(=C)CC TWCRBBJSQAZZQB-UHFFFAOYSA-N 0.000 description 1
- RYKZRKKEYSRDNF-UHFFFAOYSA-N 3-methylidenepentane Chemical compound CCC(=C)CC RYKZRKKEYSRDNF-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001447 polyvinyl benzene Polymers 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- -1 sulfonyl fluorovinyl ethyl Chemical group 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/009—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping in combination with chemical reactions
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/14—Fractional distillation or use of a fractionation or rectification column
- B01D3/143—Fractional distillation or use of a fractionation or rectification column by two or more of a fractionation, separation or rectification step
- B01D3/146—Multiple effect 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
- 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
-
- 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
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU27947/95A AU2794795A (en) | 1994-07-01 | 1995-06-30 | Process and apparatus for preparing tertiary alkyl ethers |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FI943187 | 1994-07-01 | ||
FI943187A FI95024C (fi) | 1994-07-01 | 1994-07-01 | Menetelmä ja laitteisto tertiaaristen alkyylieetterien valmistamiseksi |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1996001244A1 true WO1996001244A1 (en) | 1996-01-18 |
Family
ID=8541047
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/FI1995/000380 WO1996001244A1 (en) | 1994-07-01 | 1995-06-30 | Process and apparatus for preparing tertiary alkyl ethers |
Country Status (3)
Country | Link |
---|---|
AU (1) | AU2794795A (fi) |
FI (1) | FI95024C (fi) |
WO (1) | WO1996001244A1 (fi) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5919989A (en) * | 1996-07-16 | 1999-07-06 | Catalytic Distillation Technologies | Etherification process |
CN102675057A (zh) * | 2012-02-25 | 2012-09-19 | 中国石油大学(华东) | 一种合成甲基叔丁基醚的催化蒸馏工艺方法 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4503265A (en) * | 1981-12-04 | 1985-03-05 | Ec Erdolchemie Gmbh | Process for the production of methyl tert.-butyl ether (MTBE) and of hydrocarbon raffinates substantially freed from i-butene and from methanol |
US5243102A (en) * | 1992-10-01 | 1993-09-07 | Uop | Etherification of C5 -plus olefins by sequential catalytic distillation |
WO1993019031A1 (en) * | 1992-03-18 | 1993-09-30 | Neste Oy | Process and apparatus for preparing tertiary alkyl ethers |
WO1994008927A1 (en) * | 1992-10-16 | 1994-04-28 | Chemical Research & Licensing Company | Process for the preparation of etbe |
-
1994
- 1994-07-01 FI FI943187A patent/FI95024C/fi active
-
1995
- 1995-06-30 AU AU27947/95A patent/AU2794795A/en not_active Abandoned
- 1995-06-30 WO PCT/FI1995/000380 patent/WO1996001244A1/en active Application Filing
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4503265A (en) * | 1981-12-04 | 1985-03-05 | Ec Erdolchemie Gmbh | Process for the production of methyl tert.-butyl ether (MTBE) and of hydrocarbon raffinates substantially freed from i-butene and from methanol |
WO1993019031A1 (en) * | 1992-03-18 | 1993-09-30 | Neste Oy | Process and apparatus for preparing tertiary alkyl ethers |
US5243102A (en) * | 1992-10-01 | 1993-09-07 | Uop | Etherification of C5 -plus olefins by sequential catalytic distillation |
WO1994008927A1 (en) * | 1992-10-16 | 1994-04-28 | Chemical Research & Licensing Company | Process for the preparation of etbe |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5919989A (en) * | 1996-07-16 | 1999-07-06 | Catalytic Distillation Technologies | Etherification process |
CN102675057A (zh) * | 2012-02-25 | 2012-09-19 | 中国石油大学(华东) | 一种合成甲基叔丁基醚的催化蒸馏工艺方法 |
CN102675057B (zh) * | 2012-02-25 | 2016-12-14 | 中国石油大学(华东) | 一种合成甲基叔丁基醚的催化蒸馏工艺方法 |
Also Published As
Publication number | Publication date |
---|---|
FI95024B (fi) | 1995-08-31 |
AU2794795A (en) | 1996-01-25 |
FI95024C (fi) | 1995-12-11 |
FI943187A0 (fi) | 1994-07-01 |
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