CA1069940A - Procede pour la preparation du diisopropylether - Google Patents

Procede pour la preparation du diisopropylether

Info

Publication number: CA1069940A
Authority: CA; Canada
Prior art keywords: reactor; isopropanol; propylene; diisopropyl ether; range
Prior art date: 1976-06-03
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

Application number

CA253,967A

Other languages

English (en)

Inventor

Hanbury J. Woods

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Gulf Canada Ltd

Original Assignee

Gulf Canada Ltd

Priority date (The priority date 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 date listed.)

1976-06-03

Filing date

1976-06-03

Publication date

1980-01-15

1976-06-03 Application filed by Gulf Canada Ltd filed Critical Gulf Canada Ltd

1976-06-03 Priority to CA253,967A priority Critical patent/CA1069940A/fr

1977-05-11 Priority to DE19772721203 priority patent/DE2721203A1/de

1977-05-11 Priority to GB1966677A priority patent/GB1518480A/en

1977-05-30 Priority to IT2413477A priority patent/IT1078664B/it

1977-06-02 Priority to NL7706072A priority patent/NL7706072A/xx

1977-06-03 Priority to FR7716999A priority patent/FR2353508A1/fr

1977-06-03 Priority to JP6493577A priority patent/JPS52148008A/ja

1980-01-15 Application granted granted Critical

1980-01-15 Publication of CA1069940A publication Critical patent/CA1069940A/fr

Status Expired legal-status Critical Current

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)

CA253,967A 1976-06-03 1976-06-03 Procede pour la preparation du diisopropylether Expired CA1069940A (fr)

Priority Applications (7)

Application Number	Priority Date	Filing Date	Title
CA253,967A CA1069940A (fr)	1976-06-03	1976-06-03	Procede pour la preparation du diisopropylether
DE19772721203 DE2721203A1 (de)	1976-06-03	1977-05-11	Verfahren zur herstellung von diisopropylaether
GB1966677A GB1518480A (en)	1976-06-03	1977-05-11	Process for preparing diisopropyl ether
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.
FR7716999A FR2353508A1 (fr)	1976-06-03	1977-06-03	Procede de preparation de l'ether diisopropylique
JP6493577A JPS52148008A (en)	1976-06-03	1977-06-03	Method of producing diisopropyl ether

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA253,967A CA1069940A (fr)	1976-06-03	1976-06-03	Procede pour la preparation du diisopropylether

Publications (1)

Publication Number	Publication Date
CA1069940A true CA1069940A (fr)	1980-01-15

Family

ID=4106119

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA253,967A Expired CA1069940A (fr)	1976-06-03	1976-06-03	Procede pour la preparation du diisopropylether

Country Status (7)

Country	Link
JP (1)	JPS52148008A (fr)
CA (1)	CA1069940A (fr)
DE (1)	DE2721203A1 (fr)
FR (1)	FR2353508A1 (fr)
GB (1)	GB1518480A (fr)
IT (1)	IT1078664B (fr)
NL (1)	NL7706072A (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
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
US20090012324A1 (en) *	2006-02-14	2009-01-08	Jun-Chul Choi	Process for Production of Carboxylic Acid Ester or Ether Compound

1976
- 1976-06-03 CA CA253,967A patent/CA1069940A/fr not_active Expired
1977
- 1977-05-11 DE DE19772721203 patent/DE2721203A1/de not_active Ceased
- 1977-05-11 GB GB1966677A patent/GB1518480A/en not_active Expired
- 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
FR2353508A1 (fr)	1977-12-30
GB1518480A (en)	1978-07-19
IT1078664B (it)	1985-05-08
NL7706072A (nl)	1977-12-06
DE2721203A1 (de)	1977-12-15
JPS618808B2 (fr)	1986-03-18
JPS52148008A (en)	1977-12-08
FR2353508B1 (fr)	1979-03-09

Legal Events

Date	Code	Title	Description
1997-01-15	MKEX	Expiry

Publication	Publication Date	Title
US4042633A (en)	1977-08-16	Process for preparing diisopropyl ether
US4579984A (en)	1986-04-01	Process for the production of alcohols
EP0018032B1 (fr)	1983-03-09	Procédé de préparation d'un mélange d'hydrocarbures et mélanges d'hydrocarbures préparés selon ce procédé
JP2694176B2 (ja)	1997-12-24	メチル―ｔ―ブチルエーテルの一段階合成方法
PL140559B1 (en)	1987-05-30	Method of obtaining iii-rd order butyl-alkyl ethers
JPS6259235A (ja)	1987-03-14	線状オレフインからエ−テルの製造方法
US4327190A (en)	1982-04-27	Process for the production of C1 to C4 oxygenated hydrocarbons
CA1231724A (fr)	1988-01-19	Preparation catalytique de l'ether dimethylique
AU602438B2 (en)	1990-10-11	One-step process for dimethyl ether synthesis utilizing a liquid phase reactor system
US4026823A (en)	1977-05-31	Hydrocarbon reforming catalyst and method for preparing same
US4267393A (en)	1981-05-12	Process for producing ethers by reacting olefins with alcohols
US4565893A (en)	1986-01-21	Process of synthesis of mercaptans from olefins and hydrogen sulphide by heterogeneous catalysis
US5750759A (en)	1998-05-12	Continuous catalytic process for preparation of organic carbonates
CA1069940A (fr)	1980-01-15	Procede pour la preparation du diisopropylether
JPS55118431A (en)	1980-09-11	Preparation of methyl t-butyl ether
Fujimoto et al.	1986	Two-stage reaction system for synthesis gas conversion to gasoline
US5099072A (en)	1992-03-24	Method for one-step synthesis of methyl t-butyl ether
PL161438B1 (pl)	1993-06-30	Sposób wytwarzania propylenu PL PL PL PL PL
US5493064A (en)	1996-02-20	Noble metal large pore zeolyte catalyst for methanol-ethanol coupling
US4433174A (en)	1984-02-21	Process for preparation of alpha, beta-unsaturated aldehydes using AMS-1B borosilicate crystalline molecular sieve
US4847000A (en)	1989-07-11	Process for manufacturing synthesis gas or hydrogen by catalytic conversion of methanol in the liquid phase
US4395580A (en)	1983-07-26	Process for producing an olefin by decomposition of the corresponding ether
RU2030383C1 (ru)	1995-03-10	Способ получения метил-трет-бутилового эфира
US5043519A (en)	1991-08-27	Process for the production of tertiary olefins by decomposition of alkyl-tert.-alkyl-ethers
US5159125A (en)	1992-10-27	Catalyzed vapor phased process for making alcohols