CA1131662A - Process for the preparation of tertiary alkyl ethers - Google Patents
Process for the preparation of tertiary alkyl ethersInfo
- Publication number
- CA1131662A CA1131662A CA321,866A CA321866A CA1131662A CA 1131662 A CA1131662 A CA 1131662A CA 321866 A CA321866 A CA 321866A CA 1131662 A CA1131662 A CA 1131662A
- Authority
- CA
- Canada
- Prior art keywords
- reactor
- reaction
- preparation
- alkyl ethers
- catalyst
- 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 13
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 125000005011 alkyl ether group Chemical group 0.000 title claims abstract 3
- 238000006243 chemical reaction Methods 0.000 claims abstract description 26
- 239000003054 catalyst Substances 0.000 claims abstract description 14
- 239000011541 reaction mixture Substances 0.000 claims abstract description 10
- 150000005673 monoalkenes Chemical group 0.000 claims abstract description 7
- 150000003138 primary alcohols Chemical class 0.000 claims abstract description 6
- 239000007791 liquid phase Substances 0.000 claims abstract description 4
- 239000000463 material Substances 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 18
- 229920005989 resin Polymers 0.000 description 11
- 239000011347 resin Substances 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 4
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 4
- 238000004064 recycling Methods 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- KPAPHODVWOVUJL-UHFFFAOYSA-N 1-benzofuran;1h-indene Chemical compound C1=CC=C2CC=CC2=C1.C1=CC=C2OC=CC2=C1 KPAPHODVWOVUJL-UHFFFAOYSA-N 0.000 description 2
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000005215 alkyl ethers Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 229920001429 chelating resin Polymers 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 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 description 1
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical class C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- 101100127285 Drosophila melanogaster unc-104 gene Proteins 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000002802 bituminous coal Substances 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 229940023913 cation exchange resins Drugs 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical class O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- -1 methyl tertiary butyl Chemical group 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL7803135A NL7803135A (nl) | 1978-03-23 | 1978-03-23 | Werkwijze ter bereiding van tertiaire alkyl- ethers. |
| NL7803135 | 1978-03-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1131662A true CA1131662A (en) | 1982-09-14 |
Family
ID=19830543
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA321,866A Expired CA1131662A (en) | 1978-03-23 | 1979-02-20 | Process for the preparation of tertiary alkyl ethers |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS54130508A (enrdf_load_stackoverflow) |
| CA (1) | CA1131662A (enrdf_load_stackoverflow) |
| CH (1) | CH638477A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2911077A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2420518A1 (enrdf_load_stackoverflow) |
| GB (1) | GB2017693B (enrdf_load_stackoverflow) |
| IT (1) | IT1112964B (enrdf_load_stackoverflow) |
| NL (1) | NL7803135A (enrdf_load_stackoverflow) |
| SE (1) | SE445995B (enrdf_load_stackoverflow) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2440931A1 (fr) | 1978-11-08 | 1980-06-06 | Inst Francais Du Petrole | Procede de production d'ethers par reaction d'olefines avec des alcools |
| US4262146A (en) | 1980-01-15 | 1981-04-14 | Phillips Petroleum Company | Production of aliphatic ethers |
| FR2481269A1 (fr) * | 1980-04-28 | 1981-10-30 | Inst Francais Du Petrole | Procede de production d'ethers par reaction d'olefines avec des alcools |
| CA1254236A (en) * | 1981-07-27 | 1989-05-16 | Donald J. Makovec | Process for the preparation of methyl tert-butyl ether |
| CN100509734C (zh) | 2001-06-28 | 2009-07-08 | 日本瑞翁株式会社 | 含环烷基烷基醚的溶剂及其制备方法 |
| FR2969147B1 (fr) | 2010-12-21 | 2013-01-04 | Total Raffinage Marketing | Production d'additifs pour carburant par deshydratation et isomerisation squelettique simultanee d'isobutanol sur des catalyseurs acides suivies par une etherification |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2629769C3 (de) * | 1976-07-02 | 1989-03-16 | Hüls AG, 4370 Marl | Verfahren zur Herstellung von reinem Methyl-tertiär-butyläther |
| JPS5938933B2 (ja) * | 1976-11-22 | 1984-09-20 | 日石三菱株式会社 | 第三級アルキルエ−テルの連続的製造法 |
-
1978
- 1978-03-23 NL NL7803135A patent/NL7803135A/xx not_active Application Discontinuation
-
1979
- 1979-02-20 CA CA321,866A patent/CA1131662A/en not_active Expired
- 1979-03-20 JP JP3185779A patent/JPS54130508A/ja active Granted
- 1979-03-21 IT IT21194/79A patent/IT1112964B/it active
- 1979-03-21 DE DE19792911077 patent/DE2911077A1/de active Granted
- 1979-03-21 FR FR7907141A patent/FR2420518A1/fr active Granted
- 1979-03-21 CH CH267079A patent/CH638477A5/de not_active IP Right Cessation
- 1979-03-21 GB GB7909977A patent/GB2017693B/en not_active Expired
- 1979-03-21 SE SE7902561A patent/SE445995B/sv not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| SE7902561L (sv) | 1979-09-24 |
| DE2911077C2 (enrdf_load_stackoverflow) | 1988-10-06 |
| DE2911077A1 (de) | 1979-10-04 |
| GB2017693A (en) | 1979-10-10 |
| CH638477A5 (de) | 1983-09-30 |
| IT7921194A0 (it) | 1979-03-21 |
| JPS54130508A (en) | 1979-10-09 |
| NL7803135A (nl) | 1979-09-25 |
| GB2017693B (en) | 1982-08-11 |
| SE445995B (sv) | 1986-08-04 |
| FR2420518A1 (fr) | 1979-10-19 |
| FR2420518B1 (enrdf_load_stackoverflow) | 1984-06-29 |
| IT1112964B (it) | 1986-01-20 |
| JPS6339577B2 (enrdf_load_stackoverflow) | 1988-08-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |