GB1473263A - - Google Patents
Info
- Publication number
- GB1473263A GB1473263A GB4571875A GB4571875A GB1473263A GB 1473263 A GB1473263 A GB 1473263A GB 4571875 A GB4571875 A GB 4571875A GB 4571875 A GB4571875 A GB 4571875A GB 1473263 A GB1473263 A GB 1473263A
- Authority
- GB
- United Kingdom
- Prior art keywords
- reactant
- alcohol
- inert hydrocarbon
- ether
- raffinate
- 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
- 239000000376 reactant Substances 0.000 abstract 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 8
- 229930195733 hydrocarbon Natural products 0.000 abstract 5
- 150000002430 hydrocarbons Chemical class 0.000 abstract 5
- 239000004215 Carbon black (E152) Substances 0.000 abstract 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 4
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 abstract 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
- 235000013844 butane Nutrition 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 abstract 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 abstract 2
- 239000011541 reaction mixture Substances 0.000 abstract 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 abstract 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 abstract 1
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 abstract 1
- 239000004793 Polystyrene Substances 0.000 abstract 1
- 150000001336 alkenes Chemical class 0.000 abstract 1
- 239000006286 aqueous extract Substances 0.000 abstract 1
- 235000019445 benzyl alcohol Nutrition 0.000 abstract 1
- 239000001273 butane Substances 0.000 abstract 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003245 coal Substances 0.000 abstract 1
- 238000010586 diagram Methods 0.000 abstract 1
- 238000006266 etherification reaction Methods 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- 238000005194 fractionation Methods 0.000 abstract 1
- 239000001282 iso-butane Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 150000005673 monoalkenes Chemical class 0.000 abstract 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 abstract 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 abstract 1
- 229930015698 phenylpropene Natural products 0.000 abstract 1
- 229920002223 polystyrene Polymers 0.000 abstract 1
- QROGIFZRVHSFLM-UHFFFAOYSA-N prop-1-enylbenzene Chemical compound CC=CC1=CC=CC=C1 QROGIFZRVHSFLM-UHFFFAOYSA-N 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 229920003002 synthetic resin Polymers 0.000 abstract 1
- 239000000057 synthetic resin Substances 0.000 abstract 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 abstract 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)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Abstract
1473263 Production of ethers TEXACO DEVELOPMENT CORP 4 Nov 1975 [2 Dec 1974] 45718/75 Heading C2C An ether is prepared by (a) reacting a watersoluble alcohol as first reactant with an olefin or a water-insoluble alcohol as second reactant in an inert hydrocarbon solvent having 3 or 4 carbon atoms and in the presence of a solid etherification catalyst, thereby forming a reaction mixture including unreacted first reactant and product ether containing moieties from the first reactant and the second reactant, (b) contacting the reaction mixture with an aqueous extractant in the presence of the inert hydrocarbon, thereby forming an aqueous extract containing the first reactant and a raffinate containing rhe inert hydrocarbon and product ether, and (c) recovering the raffinate. The ether may be recovered from the raffinate, e.g. by fractionation. The first reactant may be a monohydric alcohol (e.g. a C 1 -C 6 aliphatic alcohol or benzyl alcohol) or a polyhydroxy alcohol, a number of which are listed; in the examples, methanol is used. The second reactant is for example a monoolefin i.butene, i.pentene, i.hexene, styrene or phenylpropene) or a di- or tri-olefin; alternatively it may be for example a C 5 -C 10 alcohol; the use of isobutene, is exemplified. The inert hydrocarbon is for example n.butane or isobutane. When the first reactant is isobutene, it may be admitted to the reaction as part of a refinery stream containing butanes; n.butenes present may also be classed as inert hydrocarbons in this case. The catalyst is for example a sulphonated coal or a sulphonated synthetic resin, e.g. a divinylbenzene-crosslinked polystyrene. A flow diagram of a suitable apparatus is given.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US52897074A | 1974-12-02 | 1974-12-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1473263A true GB1473263A (en) | 1977-05-11 |
Family
ID=24107977
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4571875A Expired GB1473263A (en) | 1974-12-02 | 1975-11-04 |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPS5168512A (en) |
| AR (1) | AR218609A1 (en) |
| AT (1) | AT348497B (en) |
| BE (1) | BE836051A (en) |
| BR (1) | BR7507887A (en) |
| DE (1) | DE2547380A1 (en) |
| ES (1) | ES443080A1 (en) |
| FR (1) | FR2293411A1 (en) |
| GB (1) | GB1473263A (en) |
| IN (1) | IN143386B (en) |
| IT (1) | IT1051014B (en) |
| MX (1) | MX3189E (en) |
| NL (1) | NL7513964A (en) |
| PH (1) | PH11937A (en) |
| SE (1) | SE7513302L (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4544776A (en) * | 1981-12-22 | 1985-10-01 | Deutsche Texaco Aktiengesellschaft | Process for separating methanol from the reaction products obtained in the etherification of C4 through C7 isoolefins with methanol |
| US4808270A (en) * | 1984-09-29 | 1989-02-28 | Linde Aktiengesellschaft | Process and apparatus for the preparation of ether |
| EP0604998A3 (en) * | 1992-12-30 | 1994-11-02 | Phillips Petroleum Co | Ether recovery. |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PH12545A (en) * | 1975-06-06 | 1979-06-07 | Texaco Development Corp | Method for preparation of ethers |
| JPS5714547A (en) * | 1980-06-11 | 1982-01-25 | Inst Francais Du Petrole | Manufacture of methyl-tert-butyl ether from methanol and isobutene |
| DE3024147C2 (en) | 1980-06-27 | 1983-05-05 | Edeleanu Gmbh, 6000 Frankfurt | Process for the separation of the reaction products obtained in the etherification of lower i-olefins with methanol |
| FR2565991B1 (en) * | 1984-06-18 | 1986-10-03 | Inst Francais Du Petrole | PROCESS FOR THE VALORIZATION OF OLEFINIC ESSENCES BY ETHERIFICATION |
| DE4445635A1 (en) * | 1994-12-21 | 1996-06-27 | Veba Oel Ag | Process for the preparation of polyol alkyl ethers |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB954197A (en) * | 1959-05-04 | 1964-04-02 | Sinclair Refining Co | Recovery of tertiary olefins |
| DE1224294B (en) * | 1961-01-09 | 1966-09-08 | Bayer Ag | Process for the production of tertiary butyl alkyl ethers |
| NL160234C (en) * | 1968-07-09 | 1979-10-15 | Shell Int Research | METHOD FOR INSULATING TERTIARY MONO-ALKINES FROM HYDROCARBON MIXTURES. |
| BE791661A (en) * | 1971-11-22 | 1973-05-21 | Sun Oil Co Pennsylvania | MANUFACTURE OF GASOLINE COMPOUNDS CONTAINING METHYL-2-METHOXY-2-PROPANE |
| BE793163A (en) * | 1971-12-22 | 1973-06-21 | Sun Oil Co Pennsylvania | ETHERS DRYING PROCESS |
-
1975
- 1975-10-09 JP JP50121411A patent/JPS5168512A/ja active Pending
- 1975-10-23 DE DE19752547380 patent/DE2547380A1/en active Granted
- 1975-11-03 AT AT833875A patent/AT348497B/en not_active IP Right Cessation
- 1975-11-04 GB GB4571875A patent/GB1473263A/en not_active Expired
- 1975-11-10 IN IN2144/CAL/75A patent/IN143386B/en unknown
- 1975-11-12 PH PH17764A patent/PH11937A/en unknown
- 1975-11-26 SE SE7513302A patent/SE7513302L/en unknown
- 1975-11-27 BR BR7507887*A patent/BR7507887A/en unknown
- 1975-11-27 BE BE162266A patent/BE836051A/en not_active IP Right Cessation
- 1975-11-28 FR FR7536514A patent/FR2293411A1/en active Granted
- 1975-11-28 MX MX002843U patent/MX3189E/en unknown
- 1975-11-28 ES ES443080A patent/ES443080A1/en not_active Expired
- 1975-12-01 IT IT29873/75A patent/IT1051014B/en active
- 1975-12-01 NL NL7513964A patent/NL7513964A/en not_active Application Discontinuation
-
1980
- 1980-01-01 AR AR21860980D patent/AR218609A1/en active
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4544776A (en) * | 1981-12-22 | 1985-10-01 | Deutsche Texaco Aktiengesellschaft | Process for separating methanol from the reaction products obtained in the etherification of C4 through C7 isoolefins with methanol |
| US4808270A (en) * | 1984-09-29 | 1989-02-28 | Linde Aktiengesellschaft | Process and apparatus for the preparation of ether |
| EP0604998A3 (en) * | 1992-12-30 | 1994-11-02 | Phillips Petroleum Co | Ether recovery. |
| SG87737A1 (en) * | 1992-12-30 | 2002-04-16 | Phillips Petroleum Co | Ether recovery |
Also Published As
| Publication number | Publication date |
|---|---|
| AT348497B (en) | 1979-02-26 |
| MX3189E (en) | 1980-06-23 |
| BE836051A (en) | 1976-05-28 |
| ATA833875A (en) | 1978-07-15 |
| JPS5168512A (en) | 1976-06-14 |
| DE2547380C2 (en) | 1989-10-05 |
| SE7513302L (en) | 1976-06-03 |
| DE2547380A1 (en) | 1976-08-12 |
| BR7507887A (en) | 1976-09-08 |
| FR2293411B1 (en) | 1980-05-16 |
| IN143386B (en) | 1977-11-12 |
| PH11937A (en) | 1978-09-15 |
| NL7513964A (en) | 1976-06-04 |
| IT1051014B (en) | 1981-04-21 |
| AR218609A1 (en) | 1980-06-30 |
| FR2293411A1 (en) | 1976-07-02 |
| ES443080A1 (en) | 1977-04-01 |
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| FR2329622B1 (en) | ||
| GB823932A (en) | Improvements in and relating to the polymerisation of olefines | |
| US3429943A (en) | Olefins from paraffins and carbonyl sulfide | |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |