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US4218569A Expired / Lapsed US ⏱️ 0.0 years remaining

Method for processing etherified light hydrocarbon mixtures to remove methanol

Assignee: Petro Canada Inc
•
Filing: 1978-03-14
•
Granted: 1980-08-19
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Expires: 1998-03-14
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Abstract

Abstract Mixed hydrocarbons of predominantly four carbon atoms each are subjected to etherification with methanol, to make ether from the tertiary olefin in the mixture; the unreacted hydrocarbons, after separation from the ether by distillation, are contaminated with methanol which is removed by absorption or extraction with a glycol before the hydrocarbons are subjected to further processing in which the methanol is detrimental.

Inventors

  • 👤 John D. Chase
  • 👤 Buenaventura B. Galvez
  • 👤 Bruce W. Kennedy

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-03 09:40
CPC Classifications
C; C07; C07C; C07C41/00; C07C41/01; C07C41/05; C07C41/06; C07C41/34; C07C41/38

Claims Analysis

Total Claims: 10
Claim 1
Independent Claim 154 words
A method for processing an olefinic mixed hydrocarbon stream containing predominantly hydrocarbons of only four carbon atoms each including n-butane and isobutylene, said method comprising: (i) passing the stream in admixture with methanol in contact with an etherification catalyst, in a reactor under etherifying conditions, to etherify tertiary olefins in the stream, (ii) passing the resulting ether and mixed hydrocarbon containing effluent to a fractional distillation column and distilling to provide (a) a substantially ether-free distillate containing a proportion of methanol distilling azeotropically with n-butane in the distillate and (b) a distillation residue containing substantially all of the ether from the effluent, (iii) passing said distillate through a methanol removal unit in contact with a stream of methanol miscible liquid which is ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, or a mixture of any of these to remove methanol from the distillate, and (iv) separating distillate of reduced methanol content from said liquid.
Claim 2
Independent Claim 154 words
A method for processing an olefinic mixed hydrocarbon stream containing predominantly hydrocarbons of only four carbon atoms each including n-butane and isobutylene, said method comprising: (i) passing the stream in admixture with methanol in contact with an etherification catalyst, in a reactor under etherifying conditions, to etherify tertiary olefins in the stream, (ii) passing the resulting ether and mixed hydrocarbon containing effluent to a fractional distillation column and distilling to provide (a) a substantially ether-free distillate containing a proportion of methanol distilling azeotropically with n-butane in the distillate and (b) a distillation residue containing substantially all of the ether from the effluent, (iii) passing said distillate through a methanol removal unit in contact with a stream of methanol miscible liquid which is ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, or a mixture of any of these to remove methanol from the distillate, and (iv) separating distillate of reduced methanol content from said liquid.
Claim 3
Dependent Claim 47 words
A method as claimed in claim 1 in which the methanol removal unit is a gas absorber, the methanol miscible liquid is ethylene glycol, the distillate is passed into said absorber in the vapor phase, and methanol vapor is absorbed therefrom into the liquid phase ethylene glycol.
Claim 4
Dependent Claim 58 words
A method as claimed in claim 2 in which the gas absorber is maintained at temperature in the range from 34° F. to 450° F. (1° C. to 232° C.) and the ratio of the mole flow rate of ethylene glycol to the mole flow rate of distillate vapor therein is in the range from 0.08 to 5.0.
Claim 5
Dependent Claim 42 words
A method as claimed in claim 3 in which the temperature is in the range from 70° F. to 200° F. (21° C. to 93° C.) and the ratio of the mole flow rates is in the range from 0.15 to 0.5.
Claim 6
Dependent Claim 43 words
A method as claimed in claim 1 in which the methanol removal unit is a liquid-liquid extractor, the distillate is passed thereto in liquid pahse, the methanol miscible liquid is ethylene glycol which extracts methanol therefrom in counter-current flow thereto through the extractor.
Claim 7
Dependent Claim 58 words
A method as claimed in claim 5 in which the liquid-liquid extractor is maintained at a temperature in the range from 8° F. to 350° F. (-13° C. to 177° C.) and the ratio of the mole flow rate of ethylene glycol to the mole flow rate of liquid distillate is in the range from 0.15 to 6.0.
Claim 8
Dependent Claim 42 words
A method as claimed in claim 6 in which the temperature is in the range from 50° F. to 150° F. (10° C. to 65° C.) and the ratio of the mole flow rates is in the range from 0.24 to 0.6.
Claim 9
Dependent Claim 180 words
In a method for processing an olefinic mixed hydrocarbon stream containing predominantly hydrocarbons of only four carbon atoms each including n-butane and isobutylene, in which said stream is admixed with methanol and contacted with an etherification catalyst under etherifying conditions to etherify tertiary olefins in the stream, the resulting admixture of hydrocarbons, ether, and unreacted methanol is fractionally distilled to separate a higher boiling fraction containing the ether product, most of the unreacted methanol, and some of the hydrocarbons from a lower boiling fraction containing predominantly hydrocarbons, and the lower boiling predominantly hydrocarbon fraction is subsequently contacted with acidic catalyst of the group of strong acid alkylation and polymerization catalysts, the improvement which comprises passing said lower boiling predominantly hydrocarbon fraction in contact with a stream of methanol miscible liquid which is ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, or a mixture of any of these, to remove methanol from the lower boiling hydrocarbon fraction, and separating the said fraction of reduced methanol content from said methanol miscible liquid, before said fraction is contacted with said strongly acidic catalyst.
Claim 10
Dependent Claim 180 words
In a method for processing an olefinic mixed hydrocarbon stream containing predominantly hydrocarbons of only four carbon atoms each including n-butane and isobutylene, in which said stream is admixed with methanol and contacted with an etherification catalyst under etherifying conditions to etherify tertiary olefins in the stream, the resulting admixture of hydrocarbons, ether, and unreacted methanol is fractionally distilled to separate a higher boiling fraction containing the ether product, most of the unreacted methanol, and some of the hydrocarbons from a lower boiling fraction containing predominantly hydrocarbons, and the lower boiling predominantly hydrocarbon fraction is subsequently contacted with acidic catalyst of the group of strong acid alkylation and polymerization catalysts, the improvement which comprises passing said lower boiling predominantly hydrocarbon fraction in contact with a stream of methanol miscible liquid which is ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, or a mixture of any of these, to remove methanol from the lower boiling hydrocarbon fraction, and separating the said fraction of reduced methanol content from said methanol miscible liquid, before said fraction is contacted with said strongly acidic catalyst.

References Cited (Backward Citations)

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US2580750A Cited
US2671104A Cited
US3388046A Cited
GB1173128A Cited
US3726942A Cited
GB1369889A Cited
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USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1983-08-19 1984-02-18 1984-08-19 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1987-08-19 1988-02-18 1988-08-19 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1991-08-19 1992-02-18 1992-08-19 $7700.00 Window Closed / Lapsed

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