CA1072986A - Synthese industrielle en phase liquide d'ethers methyliques tertiaires - Google Patents
Synthese industrielle en phase liquide d'ethers methyliques tertiairesInfo
- Publication number
- CA1072986A CA1072986A CA 232057 CA232057A CA1072986A CA 1072986 A CA1072986 A CA 1072986A CA 232057 CA232057 CA 232057 CA 232057 A CA232057 A CA 232057A CA 1072986 A CA1072986 A CA 1072986A
- Authority
- CA
- Canada
- Prior art keywords
- catalyst
- ether
- methyl
- liquid phase
- methanol
- 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
Links
- 238000000034 method Methods 0.000 title claims abstract description 20
- 239000007791 liquid phase Substances 0.000 title claims abstract description 5
- 150000002170 ethers Chemical group 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 26
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- 150000001336 alkenes Chemical group 0.000 claims abstract description 5
- VQTUBCCKSQIDNK-UHFFFAOYSA-N isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052750 molybdenum Inorganic materials 0.000 claims abstract description 5
- 229910052721 tungsten Inorganic materials 0.000 claims abstract description 5
- 239000011964 heteropoly acid Substances 0.000 claims abstract description 3
- 229910052720 vanadium Inorganic materials 0.000 claims abstract description 3
- 239000003054 catalyst Substances 0.000 claims description 31
- 238000006243 chemical reaction Methods 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 3
- 229910052776 Thorium Inorganic materials 0.000 claims description 2
- 229910052770 Uranium Inorganic materials 0.000 claims description 2
- 229910052787 antimony Inorganic materials 0.000 claims description 2
- 229910052785 arsenic Inorganic materials 0.000 claims description 2
- 229910052796 boron Inorganic materials 0.000 claims description 2
- 229910052804 chromium Inorganic materials 0.000 claims description 2
- 229910052803 cobalt Inorganic materials 0.000 claims description 2
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000005712 crystallization Effects 0.000 claims description 2
- 229910052732 germanium Inorganic materials 0.000 claims description 2
- 229910052748 manganese Inorganic materials 0.000 claims description 2
- 229910052702 rhenium Inorganic materials 0.000 claims description 2
- 229910052718 tin Inorganic materials 0.000 claims description 2
- 230000002378 acidificating Effects 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 229910052759 nickel Inorganic materials 0.000 claims 1
- 229910052710 silicon Inorganic materials 0.000 claims 1
- HVZJRWJGKQPSFL-UHFFFAOYSA-N 1,1-Dimethylpropyl methyl ether Chemical compound CCC(C)(C)OC HVZJRWJGKQPSFL-UHFFFAOYSA-N 0.000 abstract description 5
- BZLVMXJERCGZMT-UHFFFAOYSA-N MeOtBu Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 abstract description 5
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-Methyl-2-butene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 abstract description 4
- -1 METHYL Chemical class 0.000 abstract description 3
- ZOKXTWBITQBERF-UHFFFAOYSA-N molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 abstract description 3
- 239000011733 molybdenum Substances 0.000 abstract description 3
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 abstract description 3
- 239000010937 tungsten Substances 0.000 abstract description 3
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium(0) Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 abstract description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- 239000000047 product Substances 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 3
- LCGLNKUTAGEVQW-UHFFFAOYSA-N dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229940109526 Ery Drugs 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- YBMRDBCBODYGJE-UHFFFAOYSA-N Germanium dioxide Chemical compound O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 0.000 description 2
- 239000002638 heterogeneous catalyst Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 235000009825 Annona senegalensis Nutrition 0.000 description 1
- 241000518994 Conta Species 0.000 description 1
- 101700041727 LYST Proteins 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- HWKQNAWCHQMZHK-UHFFFAOYSA-N Trolnitrate Chemical compound [O-][N+](=O)OCCN(CCO[N+]([O-])=O)CCO[N+]([O-])=O HWKQNAWCHQMZHK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 231100000078 corrosive Toxicity 0.000 description 1
- 231100001010 corrosive Toxicity 0.000 description 1
- 230000003247 decreasing Effects 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000005842 heteroatoms Chemical group 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- PBYZMCDFOULPGH-UHFFFAOYSA-N tungstate Chemical compound [O-][W]([O-])(=O)=O PBYZMCDFOULPGH-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB23663/77A GB1520726A (en) | 1975-07-23 | 1977-06-03 | Liquid phase process for the manufacture of methyl tertiary alkyl ethers |
| BR7703932A BR7703932A (pt) | 1975-07-23 | 1977-06-16 | Processo em fase liquida para producao de eteres metilicos terciarios |
| BE178554A BE855829A (fr) | 1975-07-23 | 1977-06-17 | Preparation d'ethers methyl-t-alkyliques et produits ainsi obtenus |
| US06/071,806 US4259533A (en) | 1975-07-23 | 1979-09-04 | Liquid phase process for the manufacture of methyl tertiary ethers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1072986A true CA1072986A (fr) | 1980-03-04 |
Family
ID=209489
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 232057 Expired CA1072986A (fr) | 1975-07-23 | 1975-07-23 | Synthese industrielle en phase liquide d'ethers methyliques tertiaires |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA1072986A (fr) |
-
1975
- 1975-07-23 CA CA 232057 patent/CA1072986A/fr not_active Expired
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |