FR2481269A1 - Procede de production d'ethers par reaction d'olefines avec des alcools - Google Patents
Procede de production d'ethers par reaction d'olefines avec des alcools Download PDFInfo
- Publication number
- FR2481269A1 FR2481269A1 FR8009727A FR8009727A FR2481269A1 FR 2481269 A1 FR2481269 A1 FR 2481269A1 FR 8009727 A FR8009727 A FR 8009727A FR 8009727 A FR8009727 A FR 8009727A FR 2481269 A1 FR2481269 A1 FR 2481269A1
- Authority
- FR
- France
- Prior art keywords
- catalyst
- zone
- reaction
- reactor
- reagents
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 12
- 150000001336 alkenes Chemical class 0.000 title claims description 18
- 150000002170 ethers Chemical class 0.000 title description 4
- 150000001298 alcohols Chemical class 0.000 title description 3
- 239000003054 catalyst Substances 0.000 claims abstract description 66
- 238000006243 chemical reaction Methods 0.000 claims abstract description 61
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000007791 liquid phase Substances 0.000 claims abstract description 8
- 239000002253 acid Substances 0.000 claims abstract description 4
- 238000004519 manufacturing process Methods 0.000 claims abstract description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 239000012535 impurity Substances 0.000 claims description 9
- 239000000376 reactant Substances 0.000 claims description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 238000004523 catalytic cracking Methods 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 239000011133 lead Substances 0.000 claims description 2
- 150000002897 organic nitrogen compounds Chemical class 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 150000001339 alkali metal compounds Chemical class 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 238000006266 etherification reaction Methods 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 238000007711 solidification Methods 0.000 claims 1
- 230000008023 solidification Effects 0.000 claims 1
- 239000011949 solid catalyst Substances 0.000 abstract description 3
- 150000007514 bases Chemical class 0.000 abstract 1
- 231100000572 poisoning Toxicity 0.000 abstract 1
- 230000000607 poisoning effect Effects 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 28
- 229920005989 resin Polymers 0.000 description 22
- 239000011347 resin Substances 0.000 description 22
- 239000007788 liquid Substances 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- 230000000694 effects Effects 0.000 description 8
- 238000004064 recycling Methods 0.000 description 8
- 239000002245 particle Substances 0.000 description 6
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000005673 monoalkenes Chemical class 0.000 description 3
- 238000004230 steam cracking Methods 0.000 description 3
- WWUVJRULCWHUSA-UHFFFAOYSA-N 2-methyl-1-pentene Chemical compound CCCC(C)=C WWUVJRULCWHUSA-UHFFFAOYSA-N 0.000 description 2
- ODNBXCWGHJEIJO-UHFFFAOYSA-N 2-methylbut-1-ene 2-methylbut-2-ene Chemical compound CCC(C)=C.CC=C(C)C ODNBXCWGHJEIJO-UHFFFAOYSA-N 0.000 description 2
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000007259 addition reaction Methods 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 230000009849 deactivation Effects 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 230000035939 shock Effects 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical class C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- JMMZCWZIJXAGKW-UHFFFAOYSA-N 2-methylpent-2-ene Chemical compound CCC=C(C)C JMMZCWZIJXAGKW-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- -1 carbon olefins Chemical group 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 230000002101 lytic effect Effects 0.000 description 1
- 230000007257 malfunction Effects 0.000 description 1
- 150000001247 metal acetylides Chemical class 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000000135 prohibitive effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 238000003303 reheating Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 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
- C07C41/05—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8009727A FR2481269A1 (fr) | 1980-04-28 | 1980-04-28 | Procede de production d'ethers par reaction d'olefines avec des alcools |
| DE19813115496 DE3115496A1 (de) | 1980-04-28 | 1981-04-16 | Verfahren zur herstellung von aethern durch umsetzung von olefinen mit alkoholen |
| BE1/10207A BE888531A (fr) | 1980-04-28 | 1981-04-23 | Procede de production d'ethers par reaction d'olefines avec des alcools, |
| NL8102047A NL191462C (nl) | 1980-04-28 | 1981-04-24 | Werkwijze voor de bereiding van ethers door reaktie van tenminste een alkanol met tenminste een tertiair mono-alkeen. |
| GB8112873A GB2075017B (en) | 1980-04-28 | 1981-04-27 | Production of ethers by reacting olefins with alcohols |
| IT8121376A IT1137463B (it) | 1980-04-28 | 1981-04-27 | Procedimento di produzione di eteri per reazione di olefine con degli alcooli |
| US06/258,317 US4366327A (en) | 1980-04-28 | 1981-04-28 | Process for producing ethers by reacting olefins with alcohols |
| JP6514681A JPS56169638A (en) | 1980-04-28 | 1981-04-28 | Ether production by reaction of olefin with alcohol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8009727A FR2481269A1 (fr) | 1980-04-28 | 1980-04-28 | Procede de production d'ethers par reaction d'olefines avec des alcools |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2481269A1 true FR2481269A1 (fr) | 1981-10-30 |
| FR2481269B1 FR2481269B1 (cg-RX-API-DMAC7.html) | 1982-04-23 |
Family
ID=9241514
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8009727A Granted FR2481269A1 (fr) | 1980-04-28 | 1980-04-28 | Procede de production d'ethers par reaction d'olefines avec des alcools |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4366327A (cg-RX-API-DMAC7.html) |
| JP (1) | JPS56169638A (cg-RX-API-DMAC7.html) |
| BE (1) | BE888531A (cg-RX-API-DMAC7.html) |
| DE (1) | DE3115496A1 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2481269A1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB2075017B (cg-RX-API-DMAC7.html) |
| IT (1) | IT1137463B (cg-RX-API-DMAC7.html) |
| NL (1) | NL191462C (cg-RX-API-DMAC7.html) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0125833B1 (en) * | 1983-05-02 | 1991-01-02 | Rohm And Haas France, S.A. | Removal of impurities from hydrocarbons and alcohols |
| US5047070A (en) * | 1988-04-11 | 1991-09-10 | Mobil Oil Corporation | Integrated process for production of gasoline and ether from alcohol with feedstock extraction |
| US5120881A (en) * | 1988-11-22 | 1992-06-09 | Exxon Chemical Patents Inc | Removal of nitrogenous components of a hydrocarbon feedstream |
| US4969987A (en) * | 1989-11-29 | 1990-11-13 | Mobil Oil Corporation | Integrated process for production of gasoline and ether |
| US4990712A (en) * | 1990-05-18 | 1991-02-05 | Mobil Oil Corporation | Integrated cracking, etherification and olefin upgrading process |
| DE102011114228A1 (de) | 2011-09-23 | 2013-03-28 | L'Air Liquide, Société Anonyme pour l'Etude et l'Exploitation des Procédés Georges Claude | Gekühlter Reaktor zur Herstellung von Dimethylether aus Methanol |
| 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 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE590370A (cg-RX-API-DMAC7.html) * | 1959-04-29 | 1900-01-01 | ||
| SE349559B (cg-RX-API-DMAC7.html) * | 1968-07-09 | 1972-10-02 | Shell Nv | |
| JPS5459209A (en) * | 1977-10-14 | 1979-05-12 | Nippon Oil Co Ltd | Preparation of methyl tert-butyl ether |
| NL7803135A (nl) * | 1978-03-23 | 1979-09-25 | Shell Int Research | Werkwijze ter bereiding van tertiaire alkyl- ethers. |
| FR2440931A1 (fr) * | 1978-11-08 | 1980-06-06 | Inst Francais Du Petrole | Procede de production d'ethers par reaction d'olefines avec des alcools |
-
1980
- 1980-04-28 FR FR8009727A patent/FR2481269A1/fr active Granted
-
1981
- 1981-04-16 DE DE19813115496 patent/DE3115496A1/de not_active Ceased
- 1981-04-23 BE BE1/10207A patent/BE888531A/fr not_active IP Right Cessation
- 1981-04-24 NL NL8102047A patent/NL191462C/xx not_active IP Right Cessation
- 1981-04-27 GB GB8112873A patent/GB2075017B/en not_active Expired
- 1981-04-27 IT IT8121376A patent/IT1137463B/it active
- 1981-04-28 US US06/258,317 patent/US4366327A/en not_active Expired - Lifetime
- 1981-04-28 JP JP6514681A patent/JPS56169638A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| NL191462C (nl) | 1995-07-18 |
| BE888531A (fr) | 1981-10-23 |
| DE3115496A1 (de) | 1982-01-21 |
| FR2481269B1 (cg-RX-API-DMAC7.html) | 1982-04-23 |
| JPS56169638A (en) | 1981-12-26 |
| GB2075017B (en) | 1984-03-07 |
| IT1137463B (it) | 1986-09-10 |
| GB2075017A (en) | 1981-11-11 |
| IT8121376A0 (it) | 1981-04-27 |
| NL8102047A (nl) | 1981-11-16 |
| US4366327A (en) | 1982-12-28 |
| NL191462B (nl) | 1995-03-16 |
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