CA1069940A - Process for preparing diisopropyl ether - Google Patents
Process for preparing diisopropyl etherInfo
- Publication number
- CA1069940A CA1069940A CA253,967A CA253967A CA1069940A CA 1069940 A CA1069940 A CA 1069940A CA 253967 A CA253967 A CA 253967A CA 1069940 A CA1069940 A CA 1069940A
- Authority
- CA
- Canada
- Prior art keywords
- reactor
- isopropanol
- propylene
- diisopropyl ether
- range
- 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
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 title claims abstract description 54
- 238000004519 manufacturing process Methods 0.000 title abstract description 22
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract description 113
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims abstract description 68
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 68
- 238000006243 chemical reaction Methods 0.000 claims abstract description 54
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 claims abstract description 24
- 238000000034 method Methods 0.000 claims abstract description 17
- 239000007788 liquid Substances 0.000 claims abstract description 15
- 239000011949 solid catalyst Substances 0.000 claims abstract description 9
- 239000007791 liquid phase Substances 0.000 claims abstract description 8
- 230000002378 acidificating effect Effects 0.000 claims description 20
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 18
- 239000000376 reactant Substances 0.000 claims description 17
- 239000000463 material Substances 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 10
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 abstract description 70
- 238000005194 fractionation Methods 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- 230000018044 dehydration Effects 0.000 description 18
- 238000006297 dehydration reaction Methods 0.000 description 18
- 238000006136 alcoholysis reaction Methods 0.000 description 13
- 239000002253 acid Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 229910052901 montmorillonite Inorganic materials 0.000 description 10
- 239000000843 powder Substances 0.000 description 8
- 230000000694 effects Effects 0.000 description 6
- 230000036571 hydration Effects 0.000 description 6
- 238000006703 hydration reaction Methods 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 230000002441 reversible effect Effects 0.000 description 5
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000010425 asbestos Substances 0.000 description 4
- 239000003456 ion exchange resin Substances 0.000 description 4
- 229920003303 ion-exchange polymer Polymers 0.000 description 4
- 229910052895 riebeckite Inorganic materials 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 238000002791 soaking 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
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000012612 commercial material Substances 0.000 description 2
- 208000012839 conversion disease Diseases 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000005086 pumping Methods 0.000 description 2
- 238000004064 recycling 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
- JIEJJGMNDWIGBJ-UHFFFAOYSA-N 1-propan-2-yloxypropane Chemical compound CCCOC(C)C JIEJJGMNDWIGBJ-UHFFFAOYSA-N 0.000 description 1
- QJMYXHKGEGNLED-UHFFFAOYSA-N 5-(2-hydroxyethylamino)-1h-pyrimidine-2,4-dione Chemical compound OCCNC1=CNC(=O)NC1=O QJMYXHKGEGNLED-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000000052 comparative effect Effects 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
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/16—Clays or other mineral silicates
-
- 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)
- Dispersion Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA253,967A CA1069940A (en) | 1976-06-03 | 1976-06-03 | Process for preparing diisopropyl ether |
| GB1966677A GB1518480A (en) | 1976-06-03 | 1977-05-11 | Process for preparing diisopropyl ether |
| DE19772721203 DE2721203A1 (de) | 1976-06-03 | 1977-05-11 | Verfahren zur herstellung von diisopropylaether |
| IT2413477A IT1078664B (it) | 1976-06-03 | 1977-05-30 | Procedimento per la preparazione di etere diisopropilico |
| NL7706072A NL7706072A (nl) | 1976-06-03 | 1977-06-02 | Werkwijze ter bereiding van diisopropylether. |
| JP6493577A JPS52148008A (en) | 1976-06-03 | 1977-06-03 | Method of producing diisopropyl ether |
| FR7716999A FR2353508A1 (fr) | 1976-06-03 | 1977-06-03 | Procede de preparation de l'ether diisopropylique |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA253,967A CA1069940A (en) | 1976-06-03 | 1976-06-03 | Process for preparing diisopropyl ether |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1069940A true CA1069940A (en) | 1980-01-15 |
Family
ID=4106119
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA253,967A Expired CA1069940A (en) | 1976-06-03 | 1976-06-03 | Process for preparing diisopropyl ether |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS52148008A (Direct) |
| CA (1) | CA1069940A (Direct) |
| DE (1) | DE2721203A1 (Direct) |
| FR (1) | FR2353508A1 (Direct) |
| GB (1) | GB1518480A (Direct) |
| IT (1) | IT1078664B (Direct) |
| NL (1) | NL7706072A (Direct) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8621263D0 (en) * | 1986-09-03 | 1986-10-08 | British Petroleum Co Plc | Proton catalysed reactions |
| JPH0341042A (ja) * | 1989-07-10 | 1991-02-21 | Mitsui Toatsu Chem Inc | イソプロピルエーテルの製造方法 |
| WO2007094211A1 (ja) * | 2006-02-14 | 2007-08-23 | National Institute Of Advanced Industrial Science And Technology | カルボン酸エステルおよびエーテル化合物の製造方法 |
-
1976
- 1976-06-03 CA CA253,967A patent/CA1069940A/en not_active Expired
-
1977
- 1977-05-11 GB GB1966677A patent/GB1518480A/en not_active Expired
- 1977-05-11 DE DE19772721203 patent/DE2721203A1/de not_active Ceased
- 1977-05-30 IT IT2413477A patent/IT1078664B/it active
- 1977-06-02 NL NL7706072A patent/NL7706072A/xx not_active Application Discontinuation
- 1977-06-03 FR FR7716999A patent/FR2353508A1/fr active Granted
- 1977-06-03 JP JP6493577A patent/JPS52148008A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2353508B1 (Direct) | 1979-03-09 |
| GB1518480A (en) | 1978-07-19 |
| IT1078664B (it) | 1985-05-08 |
| DE2721203A1 (de) | 1977-12-15 |
| FR2353508A1 (fr) | 1977-12-30 |
| JPS618808B2 (Direct) | 1986-03-18 |
| NL7706072A (nl) | 1977-12-06 |
| JPS52148008A (en) | 1977-12-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |