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US5030768A Expired / Lapsed US ⏱️ 0.0 years remaining

Process for preparing alkyl tert-alkyl ethers

Assignee: Air Products and Chemicals Inc
•
Filing: 1990-03-30
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Granted: 1991-07-09
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Expires: 2010-03-30
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Abstract

Abstract A process for preparing an alkyl-tert-alkyl ether wherein an olefin having a double bond on a tertiary carbon atom and a primary alcohol are reacted in the presence of a catalyst under conditions sufficient to produce an azeotropic alcohol/ether/hydrocarbon mixture containing the alkyl-tert-alkyl ether. The azeotropic alcohol/ether/hydrocarbon mixture is subjected to a cyclic liquid phase adsorption process sequence to selectively remove the alcohol. The resulting non-azeotropic ether/hydrocarbon stream can then be easily separated by distillation to provide the desired alkyl-tert-alkyl ether product and a hydrocarbon product. The cyclic adsorption process employed to separate the alcohol from the ether/hydrocarbon mixture comprises introducing the alcohol/ether/hydrocarbon mixture into a plurality of adsorption colums containing an alcohol selective adsorbent, wherein each respective absorption column undergoes successive steps of adsorption and desorption.

Inventors

  • 👤 Michael S. Chen
  • 👤 Shivaji Sircar

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-08 13:24
CPC Classifications
C; C07; C07C; C07C41/00; C07C41/01; C07C41/34; C07C41/36; C07C41/05; C07C41/06

Claims Analysis

Total Claims: 13
Claim 1
Independent Claim 228 words
A process for producing an alkyl tert-alkyl ether comprising: (a) reacting an olefin having a double bond at a tertiary carbon atom and a primary alcohol in the presence of a catalyst under conditions sufficient to effect a condensation reaction whereby a mixture of the alkyl tert-alkyl ether, unreacted alcohol and unreacted olefin is produced; (b) introducing the mixture into a first column of a plurality of adsorption columns containing an adsorbent each of the plurality of adsorption columns which undergoes the sequential steps of: (1) passing the mixture through the first adsorption column containing the adsorbent and selectively adsorbing the unreacted primary alcohol while discharging a stream comprising a mixture of the alkyl tert-alkyl ether and the unreacted olefin; (2) rinsing the adsorption column in a direction co-current to the direction of feed flow of step (1) with the primary alcohol whereby a mixture of residual alkyl tert-alkyl ether and unreacted olefin is displaced and withdrawn from the adsorption column; and (3) rinsing the adsorption column with the olefin and withdrawing a mixture of unreacted primary alcohol and unreacted olefin from the adsorption column; (c) recycling mixture of unreacted primary alcohol and unreacted olefin from step (b:3) by combining the mixture with the feedstream recited in step (a); and (d) separating the stream from step (b:1) by distillation to produce unreacted olefin product and the alkyl tert-ether.
Claim 2
Dependent Claim 228 words
A process for producing an alkyl tert-alkyl ether comprising: (a) reacting an olefin having a double bond at a tertiary carbon atom and a primary alcohol in the presence of a catalyst under conditions sufficient to effect a condensation reaction whereby a mixture of the alkyl tert-alkyl ether, unreacted alcohol and unreacted olefin is produced; (b) introducing the mixture into a first column of a plurality of adsorption columns containing an adsorbent each of the plurality of adsorption columns which undergoes the sequential steps of: (1) passing the mixture through the first adsorption column containing the adsorbent and selectively adsorbing the unreacted primary alcohol while discharging a stream comprising a mixture of the alkyl tert-alkyl ether and the unreacted olefin; (2) rinsing the adsorption column in a direction co-current to the direction of feed flow of step (1) with the primary alcohol whereby a mixture of residual alkyl tert-alkyl ether and unreacted olefin is displaced and withdrawn from the adsorption column; and (3) rinsing the adsorption column with the olefin and withdrawing a mixture of unreacted primary alcohol and unreacted olefin from the adsorption column; (c) recycling mixture of unreacted primary alcohol and unreacted olefin from step (b:3) by combining the mixture with the feedstream recited in step (a); and (d) separating the stream from step (b:1) by distillation to produce unreacted olefin product and the alkyl tert-ether.
Claim 3
Dependent Claim 22 words
The process according to claim 1 wherein the alcohol is selected from primary alcohols having from 1 to about 8 carbon atoms.
Claim 4
Dependent Claim 19 words
The process according to claim 2 wherein the primary alcohol is selected from methanol, ethanol, propanol, butanol and pentanol.
Claim 5
Dependent Claim 17 words
The process according to claim 1 wherein the olefin has from 4 to about 10 carbon atoms.
Claim 6
Dependent Claim 15 words
The process according to claim 4 wherein the olefin is selected from isobutylene and isopentene.
Claim 7
Dependent Claim 18 words
The process according to claim 1 wherein the liquid desorbent is a C 4 to C 5 olefin.
Claim 8
Dependent Claim 16 words
The process according to claim 1 wherein the alcohol is methanol and the olefin is isopentene.
Claim 9
Dependent Claim 16 words
The process according to claim 1 wherein the alcohol is ethanol and the olefin is isobutylene.
Claim 10
Dependent Claim 13 words
The process according to claim 1 wherein the adsorbent is a 4A zeolite.
Claim 11
Dependent Claim 22 words
The process according to claim 1 wherein the adsorber feedstock is compressed to a pressure ranging from about 10 to 150 psig.
Claim 12
Dependent Claim 230 words
A process for producing methyl tert-butyl ether comprising: (a) reacting a feedstream comprising isobutene and methanol in the presence of a catalyst under conditions sufficient to effect a condensation reaction whereby a mixture of the methyl tert-butyl ether, unreacted isobutene and unreacted methanol is produced; (b) introducing the mixture into a first column of a plurality of adsorption columns containing 4A zeolite adsorbent, each of the plurality of adsorption columns which undergoes the sequential steps of: (1) passing the mixture through the first adsorption column containing the 4A zeolite adsorbent and selectively adsorbing the unreacted methanol while discharging an enriched steam comprising a mixture of the methyl tert-butyl ether and the unreacted isobutene; (2) rinsing the adsorption column with methanol in a direction co-current to the direction of feed flow of step (b) (1) whereby a mixture of residual methyl tert-butyl ether and unreacted isobutene is displaced and withdrawn from the adsorption column; and (3) rinsing the adsorption column with isobutene and withdrawing a mixture of unreacted methanol and unreacted isobutene from the adsorption column; (c) recycling the mixture of unreacted methanol and unreacted isobutene recited in step (b:3) by combining the mixture with the feedstream recited in step (a); and (d) separating the enriched stream of step (b:1) comprising the mixture of methyl tert-butyl ether and unreacted isobutene by distillation to produce an isobutene product and the alkyl tert-ether.
Claim 13
Dependent Claim 230 words
A process for producing methyl tert-butyl ether comprising: (a) reacting a feedstream comprising isobutene and methanol in the presence of a catalyst under conditions sufficient to effect a condensation reaction whereby a mixture of the methyl tert-butyl ether, unreacted isobutene and unreacted methanol is produced; (b) introducing the mixture into a first column of a plurality of adsorption columns containing 4A zeolite adsorbent, each of the plurality of adsorption columns which undergoes the sequential steps of: (1) passing the mixture through the first adsorption column containing the 4A zeolite adsorbent and selectively adsorbing the unreacted methanol while discharging an enriched steam comprising a mixture of the methyl tert-butyl ether and the unreacted isobutene; (2) rinsing the adsorption column with methanol in a direction co-current to the direction of feed flow of step (b) (1) whereby a mixture of residual methyl tert-butyl ether and unreacted isobutene is displaced and withdrawn from the adsorption column; and (3) rinsing the adsorption column with isobutene and withdrawing a mixture of unreacted methanol and unreacted isobutene from the adsorption column; (c) recycling the mixture of unreacted methanol and unreacted isobutene recited in step (b:3) by combining the mixture with the feedstream recited in step (a); and (d) separating the enriched stream of step (b:1) comprising the mixture of methyl tert-butyl ether and unreacted isobutene by distillation to produce an isobutene product and the alkyl tert-ether.

References Cited (Backward Citations)

US3726942A Cited
US4409421A Cited
US4447653A Cited
US4605787A Cited
EP0205562A1 Cited
US4774365A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1994-07-08 1995-01-07 1995-07-09 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1998-07-08 1999-01-07 1999-07-09 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2002-07-08 2003-01-07 2003-07-09 $7700.00 Window Closed / Lapsed

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