CA1098547A - Methode d'etherification d'hydrocarbures legers - Google Patents
Methode d'etherification d'hydrocarbures legersInfo
- Publication number
- CA1098547A CA1098547A CA312,338A CA312338A CA1098547A CA 1098547 A CA1098547 A CA 1098547A CA 312338 A CA312338 A CA 312338A CA 1098547 A CA1098547 A CA 1098547A
- Authority
- CA
- Canada
- Prior art keywords
- methanol
- glycol
- hydrocarbons
- stream
- effluent
- 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
- 229930195733 hydrocarbon Natural products 0.000 title claims abstract description 81
- 150000002430 hydrocarbons Chemical class 0.000 title claims abstract description 74
- 238000006266 etherification reaction Methods 0.000 title claims abstract description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 216
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 101
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 34
- 239000000203 mixture Substances 0.000 claims abstract description 29
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 18
- 239000007788 liquid Substances 0.000 claims abstract description 16
- 239000003054 catalyst Substances 0.000 claims abstract description 5
- 230000003197 catalytic effect Effects 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 29
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 150000002170 ethers Chemical class 0.000 claims description 16
- 238000009835 boiling Methods 0.000 claims description 13
- 238000002156 mixing Methods 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 150000001336 alkenes Chemical class 0.000 claims description 11
- 238000004064 recycling Methods 0.000 claims description 6
- 230000006872 improvement Effects 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 abstract description 8
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 abstract description 5
- 230000002939 deleterious effect Effects 0.000 abstract description 3
- 230000008569 process Effects 0.000 description 16
- 238000004821 distillation Methods 0.000 description 15
- 238000005804 alkylation reaction Methods 0.000 description 13
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 10
- 230000029936 alkylation Effects 0.000 description 10
- -1 carbon atom compounds Chemical class 0.000 description 9
- 238000000605 extraction Methods 0.000 description 8
- 238000004508 fractional distillation Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000006096 absorbing agent Substances 0.000 description 4
- 238000000622 liquid--liquid extraction Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000000638 solvent extraction Methods 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- GTPDHYQKBSCXAP-ZETCQYMHSA-N (2s)-4-methylsulfanyl-2-(thiophene-2-carbonylamino)butanoic acid Chemical compound CSCC[C@@H](C(O)=O)NC(=O)C1=CC=CS1 GTPDHYQKBSCXAP-ZETCQYMHSA-N 0.000 description 1
- DBUJFULDVAZULB-UHFFFAOYSA-N 1-methoxypentane Chemical compound CCCCCOC DBUJFULDVAZULB-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- UOAURXFOXHOVOU-UHFFFAOYSA-N methanol;pentane Chemical compound OC.CCCCC UOAURXFOXHOVOU-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical class OCCOCCOCCO ZIBGPFATKBEMQZ-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
- C07C41/40—Separation; Purification; Stabilisation; Use of additives by change of physical state, e.g. by crystallisation
- C07C41/42—Separation; Purification; Stabilisation; Use of additives by change of physical state, e.g. by crystallisation by distillation
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA312,338A CA1098547A (fr) | 1978-09-28 | 1978-09-28 | Methode d'etherification d'hydrocarbures legers |
| GB7932005A GB2031886B (en) | 1978-09-28 | 1979-09-14 | Etherification processing of light hydrocarbons |
| IT25952/79A IT1123304B (it) | 1978-09-28 | 1979-09-25 | Procedimento per la eterificazione di idrocarburi leggeri |
| DE19792938738 DE2938738A1 (de) | 1978-09-28 | 1979-09-25 | Verfahren zum verarbeiten von olefinischen kohlenwasserstoffgemischen |
| NL7907171A NL7907171A (nl) | 1978-09-28 | 1979-09-26 | Werkwijze ter verethering van lichte koolwaterstoffen. |
| FR7923911A FR2437389A1 (fr) | 1978-09-28 | 1979-09-26 | Perfectionnement apporte au traitement d'etherification d'hydrocarbures legers |
| JP12330379A JPS5548285A (en) | 1978-09-28 | 1979-09-27 | Improvement of light hydrocarbon etherifying treatment |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA312,338A CA1098547A (fr) | 1978-09-28 | 1978-09-28 | Methode d'etherification d'hydrocarbures legers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1098547A true CA1098547A (fr) | 1981-03-31 |
Family
ID=4112484
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA312,338A Expired CA1098547A (fr) | 1978-09-28 | 1978-09-28 | Methode d'etherification d'hydrocarbures legers |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5548285A (fr) |
| CA (1) | CA1098547A (fr) |
| DE (1) | DE2938738A1 (fr) |
| FR (1) | FR2437389A1 (fr) |
| GB (1) | GB2031886B (fr) |
| IT (1) | IT1123304B (fr) |
| NL (1) | NL7907171A (fr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55169336U (fr) * | 1979-05-22 | 1980-12-05 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1089881A (fr) * | 1978-03-10 | 1980-11-18 | Gulf Canada Limited | Methode de traitement de fractions legeres d'hydrocarbures etherifies, permettant l'extraction du methanol |
| FR2465699A1 (fr) * | 1979-09-19 | 1981-03-27 | Gulf Canada Ltd | Procede de traitement de melanges d'hydrocarbures legers etherifies pour en enlever le methanol |
-
1978
- 1978-09-28 CA CA312,338A patent/CA1098547A/fr not_active Expired
-
1979
- 1979-09-14 GB GB7932005A patent/GB2031886B/en not_active Expired
- 1979-09-25 IT IT25952/79A patent/IT1123304B/it active
- 1979-09-25 DE DE19792938738 patent/DE2938738A1/de not_active Ceased
- 1979-09-26 FR FR7923911A patent/FR2437389A1/fr active Granted
- 1979-09-26 NL NL7907171A patent/NL7907171A/nl not_active Application Discontinuation
- 1979-09-27 JP JP12330379A patent/JPS5548285A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| NL7907171A (nl) | 1980-04-01 |
| GB2031886A (en) | 1980-04-30 |
| FR2437389B1 (fr) | 1984-04-20 |
| IT7925952A0 (it) | 1979-09-25 |
| DE2938738A1 (de) | 1980-04-10 |
| IT1123304B (it) | 1986-04-30 |
| FR2437389A1 (fr) | 1980-04-25 |
| GB2031886B (en) | 1982-11-10 |
| JPS5548285A (en) | 1980-04-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |