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US4267393A Expired / Lapsed US ⏱️ 0.0 years remaining

Process for producing ethers by reacting olefins with alcohols

Assignee: IFP Energies nouvelles
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Filing: 1979-11-08
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Granted: 1981-05-12
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Expires: 1999-11-08
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Abstract

Abstract An ether is prepared by reacting a selected olefin with an alcohol in a two reaction zone system: in the first reaction zone, the catalyst is dispersed in the liquid phase of the reactants and boiling of the mixture is avoided; in the second reaction zone, the catalyst is in a fixed bed. A cooled recycle stream is fed back to the first stage reactor. The catalyst is a sulfonated ion exchange resin in the acid form.

Inventors

  • 👤 Bernard Torck
  • 👤 Hugo Van Landeghem
  • 👤 Quang D. Vu
  • 👤 Michel Hellin

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-29 22:45
CPC Classifications
C; C07; C07C; C07C41/00; C07C41/01; C07C41/05; C07C41/06

Claims Analysis

Total Claims: 19
Claim 1
Independent Claim 318 words
In a process for manufacturing ethers by contacting a mixture of at least one olefin having a double bond on a tertiary carbon atom and at least one alcohol with a sulfonated ion exchange resin catalyst in the acid form, the improvement comprising passing a liquid mixture of fresh reactants comprising said at least one olefin and said at least one alcohol, together with a liquid recycle stream as hereinafter defined at a feed rate of from 0.1 to 15 times the feed rate of the fresh reactants, upwardly through a first reaction zone containing a catalyst bed of particles of said sulfonated ion exchange resin in the acid form, at a temperature of from 60° to 120° C., said temperature being lower than the boiling temperature of the constituent of highest volatility in the mixture passing through the first reaction zone at the selected pressure, while maintaining a feed rate which is sufficient to expand the volume of said catalyst bed by at least 2% and to disperse the catalyst particles therein but insufficient to carry a substantial proportion of catalyst out of said first reaction zone, the contact time being selected to convert from 60 to 95% of said olefin; discharging the liquid product mixture formed in the first reaction zone, cooling a first portion thereof, and recycling the cooled portion to the first reaction zone as said liquid recycle stream, and feeding a second portion of said liquid product mixture to a second reaction zone containing a fixed bed of said sulfonated ion exchange resin catalyst in the acid form, at a temperature of from 30° to 70° C., the temperature in the second zone being at least 10° C. lower than the outlet temperature of the first reaction zone and lower than the boiling temperature of the constituent of highest volatility in the mixture passing through the second reaction zone at the selected pressure.
Claim 2
Dependent Claim 318 words
In a process for manufacturing ethers by contacting a mixture of at least one olefin having a double bond on a tertiary carbon atom and at least one alcohol with a sulfonated ion exchange resin catalyst in the acid form, the improvement comprising passing a liquid mixture of fresh reactants comprising said at least one olefin and said at least one alcohol, together with a liquid recycle stream as hereinafter defined at a feed rate of from 0.1 to 15 times the feed rate of the fresh reactants, upwardly through a first reaction zone containing a catalyst bed of particles of said sulfonated ion exchange resin in the acid form, at a temperature of from 60° to 120° C., said temperature being lower than the boiling temperature of the constituent of highest volatility in the mixture passing through the first reaction zone at the selected pressure, while maintaining a feed rate which is sufficient to expand the volume of said catalyst bed by at least 2% and to disperse the catalyst particles therein but insufficient to carry a substantial proportion of catalyst out of said first reaction zone, the contact time being selected to convert from 60 to 95% of said olefin; discharging the liquid product mixture formed in the first reaction zone, cooling a first portion thereof, and recycling the cooled portion to the first reaction zone as said liquid recycle stream, and feeding a second portion of said liquid product mixture to a second reaction zone containing a fixed bed of said sulfonated ion exchange resin catalyst in the acid form, at a temperature of from 30° to 70° C., the temperature in the second zone being at least 10° C. lower than the outlet temperature of the first reaction zone and lower than the boiling temperature of the constituent of highest volatility in the mixture passing through the second reaction zone at the selected pressure.
Claim 3
Dependent Claim 45 words
A process according to claim 1, wherein substantially adiabatic conditions are maintained in said first reaction zone, and at least the major part of the reaction heat evolved in the first reaction zone is extracted from the recycle stream outside of said first reaction zone.
Claim 4
Dependent Claim 40 words
A process according to claim 2, wherein the circulation rate of the liquid mixture of reactants in the first reaction zone is from 0.5 to 10 cm/sec and the size of the catalyst particles is from 0.05 to 5 mm.
Claim 5
Dependent Claim 36 words
A process according to claim 3, wherein the circulation rate of the liquid mixture of the reactants is from 1 to 4 cm/sec and the size of the catalyst particles is from 0.3 to 1.5 mm.
Claim 6
Dependent Claim 24 words
A process according to claim 1, wherein the recycle rate is 0.5 to 4 times the feed rate of the fresh charge of reactants.
Claim 7
Dependent Claim 28 words
A process according to claim 1, wherein the olefin is isobutene and its total conversion is at least 90%, with at least 3% in the second reaction zone.
Claim 8
Dependent Claim 11 words
A process according to claim 6, wherein the alcohol is methanol.
Claim 9
Dependent Claim 19 words
A process according to claim 6, wherein isobutene is supplied as a steam-cracking or catalytic cracking C 4 cut.
Claim 10
Dependent Claim 14 words
A process according to claim 8, wherein the C 4 cut also contains butadiene.
Claim 11
Dependent Claim 17 words
A process according to claim 1, wherein said at least one alcohol is at least one alkanol.
Claim 12
Dependent Claim 20 words
A process according to claim 1, wherein said at least one alcohol is at least one of methanol and ethanol.
Claim 13
Dependent Claim 20 words
A process according to claim 1, wherein the temperature in the second reaction zone is from 45° to 60° C.
Claim 14
Dependent Claim 22 words
A process according to claim 1, wherein the pressure in the first and second reaction zones is from 5 to 50 bars.
Claim 15
Dependent Claim 35 words
A process according to claim 6, wherein the temperature in the first reaction zone is from 80° to 100° C., and the conversion of isobutene in the first reaction zone is from 75 to 92%.
Claim 16
Dependent Claim 34 words
A process according to claim 1, wherein the olefin is at least one of 2-methyl-1-butene and 2-methyl-2-butene and its total conversion is at least 70%, with at least 3% in the second reaction zone.
Claim 17
Dependent Claim 11 words
A process according to claim 15, wherein the alcohol is methanol.
Claim 18
Dependent Claim 27 words
A process according to claim 15, wherein said at least one of 2-methyl-1-butene and 2-methyl-2-butene is supplied as a steam cracking or catalytic cracking C 5 cut.
Claim 19
Dependent Claim 33 words
A process according to claim 15, wherein the temperature in the first reaction zone is from 70° to 90° C., and the conversion in the first reaction zone is from 50 to 70%.

References Cited (Backward Citations)

CA929537A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1984-05-11 1984-11-10 1985-05-12 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1988-05-11 1988-11-10 1989-05-12 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1992-05-11 1992-11-10 1993-05-12 $7700.00 Window Closed / Lapsed

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