FR2465699A1 - Procede de traitement de melanges d'hydrocarbures legers etherifies pour en enlever le methanol - Google Patents
Procede de traitement de melanges d'hydrocarbures legers etherifies pour en enlever le methanol Download PDFInfo
- Publication number
- FR2465699A1 FR2465699A1 FR7923319A FR7923319A FR2465699A1 FR 2465699 A1 FR2465699 A1 FR 2465699A1 FR 7923319 A FR7923319 A FR 7923319A FR 7923319 A FR7923319 A FR 7923319A FR 2465699 A1 FR2465699 A1 FR 2465699A1
- Authority
- FR
- France
- Prior art keywords
- methanol
- liquid
- distillate
- glycol
- hydrocarbons
- 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 title claims abstract description 264
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 title claims abstract description 71
- 238000006266 etherification reaction Methods 0.000 title claims abstract description 22
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 title claims abstract description 11
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 title claims abstract description 11
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 53
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 50
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims abstract description 16
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000003054 catalyst Substances 0.000 claims abstract description 15
- 150000002170 ethers Chemical class 0.000 claims abstract description 14
- 150000001336 alkenes Chemical class 0.000 claims abstract description 13
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims abstract description 12
- 230000029936 alkylation Effects 0.000 claims abstract description 11
- 238000005804 alkylation reaction Methods 0.000 claims abstract description 11
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 19
- 239000007788 liquid Substances 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 13
- 238000000622 liquid--liquid extraction Methods 0.000 claims description 9
- 238000000638 solvent extraction Methods 0.000 claims description 9
- 239000006096 absorbing agent Substances 0.000 claims description 8
- 238000009835 boiling Methods 0.000 claims description 8
- 238000009434 installation Methods 0.000 claims description 7
- 230000008030 elimination Effects 0.000 claims description 6
- 238000003379 elimination reaction Methods 0.000 claims description 6
- -1 C4 only Chemical class 0.000 claims description 5
- 238000004508 fractional distillation Methods 0.000 claims description 5
- 239000007791 liquid phase Substances 0.000 claims description 5
- 238000006116 polymerization reaction Methods 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 239000012808 vapor phase Substances 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- 241000282326 Felis catus Species 0.000 claims 1
- 239000000284 extract Substances 0.000 claims 1
- 239000002685 polymerization catalyst Substances 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract description 14
- 238000002156 mixing Methods 0.000 abstract 1
- 238000000926 separation method Methods 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 238000004821 distillation Methods 0.000 description 7
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 5
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 238000004523 catalytic cracking Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000001577 simple distillation Methods 0.000 description 3
- 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 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000002745 absorbent Effects 0.000 description 2
- 239000002250 absorbent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- 150000001983 dialkylethers Chemical class 0.000 description 2
- 238000011143 downstream manufacturing Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- NDHLFBLLLFBZTR-UHFFFAOYSA-N butane;methanol Chemical compound OC.CCCC NDHLFBLLLFBZTR-UHFFFAOYSA-N 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 229940023913 cation exchange resins Drugs 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920003053 polystyrene-divinylbenzene Polymers 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005406 washing Methods 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
- C07C41/34—Separation; Purification; Stabilisation; Use of additives
-
- 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
- C07C41/38—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/005—Processes comprising at least two steps in series
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/10—Purification; Separation; Use of additives by extraction, i.e. purification or separation of liquid hydrocarbons with the aid of liquids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
- C07C7/14875—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound with organic compounds
- C07C7/14891—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound with organic compounds alcohols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7923319A FR2465699A1 (fr) | 1979-09-19 | 1979-09-19 | Procede de traitement de melanges d'hydrocarbures legers etherifies pour en enlever le methanol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7923319A FR2465699A1 (fr) | 1979-09-19 | 1979-09-19 | Procede de traitement de melanges d'hydrocarbures legers etherifies pour en enlever le methanol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2465699A1 true FR2465699A1 (fr) | 1981-03-27 |
| FR2465699B1 FR2465699B1 (enExample) | 1983-06-10 |
Family
ID=9229795
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7923319A Granted FR2465699A1 (fr) | 1979-09-19 | 1979-09-19 | Procede de traitement de melanges d'hydrocarbures legers etherifies pour en enlever le methanol |
Country Status (1)
| Country | Link |
|---|---|
| FR (1) | FR2465699A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2437389A1 (fr) * | 1978-09-28 | 1980-04-25 | Gulf Canada Ltd | Perfectionnement apporte au traitement d'etherification d'hydrocarbures legers |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2580750A (en) * | 1949-05-09 | 1952-01-01 | Phillips Petroleum Co | Solvent extraction of oxygenated organic compounds |
| FR2160862A1 (enExample) * | 1971-11-22 | 1973-07-06 | Sun Oil Co Pennsylvania |
-
1979
- 1979-09-19 FR FR7923319A patent/FR2465699A1/fr active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2580750A (en) * | 1949-05-09 | 1952-01-01 | Phillips Petroleum Co | Solvent extraction of oxygenated organic compounds |
| FR2160862A1 (enExample) * | 1971-11-22 | 1973-07-06 | Sun Oil Co Pennsylvania |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2437389A1 (fr) * | 1978-09-28 | 1980-04-25 | Gulf Canada Ltd | Perfectionnement apporte au traitement d'etherification d'hydrocarbures legers |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2465699B1 (enExample) | 1983-06-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2135127C (fr) | Procede de separation des composes oxygenes d'hydrocarbures, combinant une distillation et une permeation et son utilisation en etherification | |
| EP0781829B1 (fr) | Procédé et dispositif d'hydrogénation sélective par distillation catalytique | |
| BG99017A (bg) | Каталитична дестилационна колона и етерификационен метод, използващ тази колона | |
| LU84079A1 (fr) | Procede de preparation d'ethers alkyliques tertiaires | |
| FR2504522A1 (fr) | Procede de purification d'une coupe c4 et/ou c5 d'hydrocarbures renfermant de l'eau et du dimethylether comme impuretes | |
| GB2043640A (en) | Process for isolating methyl t-butylether from the reaction products of methanol with a c hydrocarbon cut containing isobutene | |
| JPH0578262A (ja) | 抽出蒸溜によるブテンとブタンとの分離方法 | |
| US4218569A (en) | Method for processing etherified light hydrocarbon mixtures to remove methanol | |
| FR2474024A1 (fr) | Procede de production de butene-1 a partir d'une coupe c4 d'hydrocarbures | |
| EP0542596B1 (fr) | Procédé de séparation d'éthyl tertiobutyl éther et d'éthanol | |
| EP0861818B1 (fr) | Procédé de production d'oléfine tertiaire par décomposition d'éther alkylique tertiaire comportant une première étape de purification par lavage à l'eau | |
| EP0869107B1 (fr) | Procédé de production d'alpha oléfine, d'oléfine tertiaire et/ou d'éther à partir de coupe hydrocarbonée insaturée | |
| EP0922018B1 (fr) | Procede de production d'isobutene de haute purete a partir d'une coupe c4 contenant de l'isobutene et du butene-1 | |
| EP0860412B1 (fr) | Procédé de production d'oléfine tertiaire par décomposition d'éther alkylique tertiaire | |
| EP0068981A1 (fr) | Procédé d'obtention conjointe de butène-1 de haute pureté et de supercarburant à partir d'une coupe C4 oléfinique | |
| FR2465699A1 (fr) | Procede de traitement de melanges d'hydrocarbures legers etherifies pour en enlever le methanol | |
| US2386058A (en) | Purification of organic liquids | |
| FR2673624A1 (fr) | Procede de separation d'ethyl tertiobutyl ether a partir de melanges avec l'ethanol. | |
| FR2761682A1 (fr) | Procede de production d'ether et d'olefine a partir de coupe hydrocarbonee contenant au moins une olefine tertiaire par synthese puis decomposition d'ether comportant une premiere etape de purification d'olefine par lavage a l'eau | |
| US4204077A (en) | Etherification processing of light hydrocarbons | |
| JP3198356B2 (ja) | ３級アミルアルキルエーテルに富みオレフィン類を含まない溜分とｎ−ペンタンに富むパラフィン溜分の製造法 | |
| CA1089881A (en) | Method for processing etherified light hydrocarbon mixtures to remove methanol | |
| RU2785840C2 (ru) | Способ разделения ароматических углеводородов с применением экстракционной дистилляции | |
| RU2381208C1 (ru) | Способ выделения бензола из смесей с неароматическими углеводородами | |
| CA1098547A (en) | Etherification processing of light hydrocarbons |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |