Organic Compound Patents (Class 203/57)
  • Patent number: 4738755
    Abstract: m-Xylene is difficult to separate from o-xylene by conventional rectification or distillation because of the close proximity of their boiling points. m-Xylene can be readily separated from o-xylene by using extractive distillation in which the extractive agent is ethyl-2-hydroxybenzoate; methyl benzoate plus benzophenone; methyl benzoate, butyl benzoate and dimethylsulfoxide.
    Type: Grant
    Filed: March 10, 1987
    Date of Patent: April 19, 1988
    Inventors: Lloyd Berg, An-I Yeh
  • Patent number: 4735690
    Abstract: Impure formic acid cannot be completely removed from formic acid-water-impurity mixtures by distillation because of the presence of the maximum azeotrope between formic acid and water. Formic acid can be readily removed from mixtures containing it, water and impurities of the ether, ester, ketone or diketone type by using extractive distillation in which the extractive agent is a higher boiling oxygenated, nitrogenous or sulfur containing organic compound or a mixture of these. Examples of effective agents are adiponitrile; sulfolane and salicyclic acid; dimethylformamide, N,N-dimethylacetamide and ethylene glycol ethyl ether acetate.
    Type: Grant
    Filed: April 28, 1986
    Date of Patent: April 5, 1988
    Inventors: Lloyd Berg, An-I Yeh
  • Patent number: 4729818
    Abstract: Acetic acid cannot be easily removed from acetic acid--water mixtures by distillation because of the closeness of their boiling points and the deviation from ideal solution behavior. Acetic acid can be readily removed from mixtures containing it and water by using extractive distillation in which the extractive distillation agent is a mono carboxylic acid, either singly or admixed with high boiling organic compounds. Typical examples of effective agents are pelargonic acid; heptanoic acid and isophorone; neodecanoic acid, acetophenone and nitrobenzene.
    Type: Grant
    Filed: April 16, 1987
    Date of Patent: March 8, 1988
    Inventor: Lloyd Berg
  • Patent number: 4724049
    Abstract: Isobutyl acetate cannot be completely removed from isobutyl acetate - isobutanol - water mixtures by distillation because of the presence of the minimum ternary axeotrope. Isobutyl acetate can be readily removed from mixtures containing it, isobutanol and water by using extractive distillation in which the extractive distillation agent is a higher boiling oxygenated, nitrogenous and/or sulfur containing organic compound or a mixture of these. Typical examples of effective agents are dimethylsulfoxide; dimethylsulfoxide and dimethylformamide; dimethylsulfoxide, dimethylformamide and N,N-dimethylacetamide.
    Type: Grant
    Filed: June 26, 1986
    Date of Patent: February 9, 1988
    Inventors: Lloyd Berg, An-I Yeh
  • Patent number: 4718989
    Abstract: Isopropanol cannot be completely removed from isopropanol-isopropyl acetate-water mixtures by distillation because of the presence of the minimum ternary azeotrope. Isopropanol can be readily removed from mixtures containing it, isopropyl acetate and water by using extractive distillation in which the extractive agent is a higher boiling ester of phthalic acid. Typical examples of effective agents are diisooctyl phthalate and methyl benzoate, dibutyl phthalate, methyl benzoate and nitromethane.
    Type: Grant
    Filed: February 26, 1987
    Date of Patent: January 12, 1988
    Inventors: Lloyd Berg, Mark G. Vosburgh
  • Patent number: 4718988
    Abstract: 2-Butyl acetate cannot be completely removed from 2-butyl acetate-2-butanol-water mixtures by distillation because of the presence of the minimum ternary azeotrope. 2-butyl acetate can be readily removed from mixtures containing it, 2-butanol and water by using extractive distillation in which the extractive distillation agent is a higher boiling oxygenated, nitrogenous and/or sulfur containing organic compound or a mixture of these. Typical examples of effective agents are N,N-dimethylacetamide; dimethylformamide and ethylene glycol; acetamide, dimethylsulfoxide and ethylene glycol.
    Type: Grant
    Filed: March 27, 1986
    Date of Patent: January 12, 1988
    Inventors: Lloyd Berg, An-I Yeh
  • Patent number: 4718987
    Abstract: Isopropanol cannot be completely removed from isopropanol--isopropyl acetate--water mixtures by distillation because of the presence of the minimum ternary azeotrope. Isopropanol can be readily removed from mixtures containing it, isopropyl acetate and water by using extractive distillation in which the extractive agent is a higher boiling benzoate mixed with certain oxygenated or nitrogeneous organic compounds. Typical examples are butyl benzoate and ethylene carbonate; methyl benzoate, 2-nitropropane and n-decanol.
    Type: Grant
    Filed: February 12, 1987
    Date of Patent: January 12, 1988
    Inventors: Lloyd Berg, Mark G. Vosburgh
  • Patent number: 4695350
    Abstract: n-Hexyl acetate cannot be completely removed from n-hexyl acetate- n-hexyl alcohol- water mixtures by distillation because of the presence of the minimum ternary azeotrope. n-Hexyl acetate can be readily removed from mixtures containing it, n-hexyl alcohol and water by using extractive distillation in which the extractive distillation agent is dimethylsulfoxide or a mixture of DMSO with a higher boiling organic compound. Typical examples of effective agents are DMSO; DMSO and tetraethylene glycol; DMSO, dimethylformamide and hexylene glycol.
    Type: Grant
    Filed: January 27, 1986
    Date of Patent: September 22, 1987
    Inventor: Lloyd Berg
  • Patent number: 4693788
    Abstract: t-Amyl alcohol and isobutanol cannot be separated from each other by distillation because of the proximity of their boiling points. t-Amyl alcohol can be readily separated from isobutanol by using extractive distillation in which the extractive agent is a higher boiling organic compound or a mixture of two or more of these. Typical examples of effective agents are: dimethylformamide; N,N-dimethylacetamide; N,N-dimethylacetamide and dimethylsulfoxide; dimethylformamide, N,N-dimethylacetamide and phthalic anhydride.
    Type: Grant
    Filed: March 17, 1987
    Date of Patent: September 15, 1987
    Inventors: Lloyd Berg, Michael J. Shanahan
  • Patent number: 4693787
    Abstract: t-Amyl alcohol and isobutanol cannot be separated from each other by distillation because of the proximity of their boiling points. t-Amyl alcohol can be readily separated form isobutanol by using extractive distillation in which the extractive agent is a higher boiling organic compound or a mixture of two or more of these. Typical examples of effective agents are: dimethylsulfoxide; dimethylsulfoxide and N,N-dimethylacetamide; dimethylsulfoxide, dimethylformamide and phthalic anhydride.
    Type: Grant
    Filed: March 2, 1987
    Date of Patent: September 15, 1987
    Inventors: Lloyd Berg, Michael J. Shanahan
  • Patent number: 4692219
    Abstract: Formic acid cannot be easily removed from acetic acid by distillation because of the closeness of their vapor pressures. Formic acid can be readily removed from acetic acid by extraction distillation. Typical extractive distillation agents are carboxylic acids in the range of hexamoic acid to neodecanoic acid with or without solvents such as methyl benzoate, acetophenone and nitrobenzene.
    Type: Grant
    Filed: December 3, 1986
    Date of Patent: September 8, 1987
    Assignee: Celanese Chemical Co.
    Inventor: Lloyd Berg
  • Patent number: 4690734
    Abstract: n-Amyl acetate cannot be completely removed from n-amyl acetate - n-amyl alcohol - water mixtures by distillation because of the presence of the minimum ternary azeotrope. n-Amyl acetate can be readily removed from mixtures containing it, n-amyl alcohol and water by using extractive distillation in which the extractive distillation agent is a higher boiling organic compound or a mixture of these. Typical examples of effective agents are ethylene glycol; propylene glycol and dimethylsulfoxide; 1,3-butanediol, dimethylformamide and acetamide.
    Type: Grant
    Filed: November 25, 1985
    Date of Patent: September 1, 1987
    Inventors: Lloyd Berg, An-I Yeh
  • Patent number: 4676872
    Abstract: m-Xylene is difficult to separate from o-xylene by conventional distillation or rectification because of the close proximity of their boiling points. m-Xylene can be readily separated from o-xylene by using extractive distillation in which the extractive agent is adiponitrile or a mixture of it with certain high boiling organic compounds. Typical examples of effective agents are: adiponitrile; adiponitrile and 1,4-butanediol; adiponitrile, ethylene carbonate and benzyl alcohol.
    Type: Grant
    Filed: April 21, 1986
    Date of Patent: June 30, 1987
    Inventors: Lloyd Berg, An-I Yeh
  • Patent number: 4675080
    Abstract: Isopropanol cannot be completely removed from isopropanol-isopropyl acetate-water mixtures by distillation because of the presence of the minimum ternary azeotrope. Isopropanol can be readily removed from mixtures containing it, isopropyl acetate and water by using extractive distillation in which the extractive agent is a higher boiling ester of phthalic acid. Typical examples of effective agents are diethyl phthalate, diisooctyl phthalate and methyl benzoate, dibutyl phthalate, methyl benzoate and nitromethane.
    Type: Grant
    Filed: September 30, 1985
    Date of Patent: June 23, 1987
    Inventors: Lloyd Berg, Mark G. Vosburgh
  • Patent number: 4673465
    Abstract: m-Xylene is difficult to separate from o-xylene by conventional distillation or rectification because of the close proximity of their boiling points. m-Xylene can be readily separated from o-xylene by using extractive distillation in which the extractive agent is a mixture polychloro aromatic compounds. Typical examples of effective agents are 2,3,4,6-tetrachlorophenol and p-dichlorobenzene; dimethyltetrachloroterephthalate, 2,3,4,6-tetrachlorophenol and 1,2,4,5-tetrachlorobenzene; 2,4,5-trichlorophenol, benzene hexachloride, o-dichlorobenzene and dioctyl phthalate.
    Type: Grant
    Filed: April 21, 1986
    Date of Patent: June 16, 1987
    Inventors: Lloyd Berg, An-I Yeh
  • Patent number: 4670105
    Abstract: Propanoic acid cannot be completely removed from propanoic-water mixtures by distillation because of the presence of the minimum azeotrope. Propanoic acid can be readily removed from mixtures containing it and water by using extractive distillation in which the extractive distillation agent is an acid amide. Typical examples of effective agents are acetamide; dimethylformamide and methyl glutaronitrile; formamide, adiponitrile and N,N-dimethylacetamide.
    Type: Grant
    Filed: April 7, 1986
    Date of Patent: June 2, 1987
    Inventors: Lloyd Berg, An-I Yeh
  • Patent number: 4670106
    Abstract: n-Amyl acetate cannot be completely removed from n-amyl acetate - n-amyl alcohol - water mixtures by distillation because of the presence of the minimum ternary azeotrope. n-Amyl acetate can be readily removed from mixtures containing it, n-amyl alcohol and water by using extractive distillation in which the extractive distillation agent is a higher boiling organic compound or a mixture of these. Typical examples of effective agents are dimethylsulfoxide; N,N-dimethylacetamide and dimethylsulfoxide; dimethylformamide, N,N-dimethylacetamide and acetamide.
    Type: Grant
    Filed: December 2, 1985
    Date of Patent: June 2, 1987
    Inventors: Lloyd Berg, An-I Yeh
  • Patent number: 4666560
    Abstract: Isopropanol cannot be completely removed from isopropanol - isopropyl acetate - water mixtures by distillation because of the presence of the minimum ternary azeoptrope. Isopropanol can be readily removed from mixtures containing it, isopropyl acetate and water by using extractive distillation in which the extractive agent is a higher boiling benzoate or nitro paraffin. Typical examples are methyl benzoate; methyl benzoate and nitromethane; butyl benzoate, nitromethane and nitroethane.
    Type: Grant
    Filed: October 11, 1985
    Date of Patent: May 19, 1987
    Inventors: Lloyd Berg, Mark G. Vosburgh
  • Patent number: 4661208
    Abstract: The invention provides a means for greatly saving the thermal energy consumption in the dehydrating distillation of an aqueous solution of a carboxylic acid such as acetic acid by use of an azeotropically distilling entrainer boiling at a lower temperature than the carboxylic acid and immiscible with water. The improvement proposed by the invention comprises taking at least a part of the entrainer phase separated from the condensate coming from the column top or at least a part of the side-cut fluid abstracted from the refluxing fluid inside the column, evaporating the thus taken fluid into vapor and introducing the vapor into the distillation column at a stage for the introduction of the starting feed or below.
    Type: Grant
    Filed: June 21, 1985
    Date of Patent: April 28, 1987
    Assignee: Shin-Etsu Vinyl Acetate Co., Ltd.
    Inventors: Yoshihiro Honma, Fumiaki Kawamoto, Shozo Tanaka
  • Patent number: 4661209
    Abstract: Methyl t-butyl ether cannot be separated from close boiling hydrocarbons by distillation because of the proximity of their boiling points. Methyl t-butyl ether can be readily separated from close boiling hydrocarbons by using extractive distillation in which the extractive agent is higher boiling oxygenated, nitrogenous and/or sulfur containing organic compound or a mixture of two or more of these. Typical examples of effective agents are dimethylsulfoxide; dimethylsulfoxide and 2-octanone; dimethylsulfoxide, dimethylformamide and N-methyl pyrrolidone.
    Type: Grant
    Filed: August 1, 1986
    Date of Patent: April 28, 1987
    Inventor: Lloyd Berg
  • Patent number: 4642166
    Abstract: Formic acid cannot be completely removed from formic acid - water mixtures by distillation because of the presence of the maximum azeotrope. Formic acid can be readily removed from mixtures containing it and water by using extractive distillation in which the extractive distillation agent is a sulfone. Typical examples of effective agents are thiophan sulfone; dimethyl sulfone and adiponitrile; phenyl sulfone, adiponitrile and acetophenone.
    Type: Grant
    Filed: February 10, 1986
    Date of Patent: February 10, 1987
    Inventors: Lloyd Berg, An-I Yeh
  • Patent number: 4620901
    Abstract: Acetone cannot be completely removed from acetone-methanol mixtures by distillation because of the presence of the minimum boiling azeotrope. Acetone can be readily separated from methanol by using extractive distillation in which the extractive agent is dimethylformamide, either alone or admixed with other compounds. Typical examples of effective agents are: dimethylformamide; dimethylformamide and diethylene glycol; dimethyl formamide, glycerine and propylene glycol.
    Type: Grant
    Filed: November 4, 1985
    Date of Patent: November 4, 1986
    Inventors: Lloyd Berg, Karl J. Warren
  • Patent number: 4601791
    Abstract: N-propanol and allyl alcohol cannot be separated from each other by distillation because of the proximity of their boiling points. N-propanol can be readily separated from allyl alcohol by using extractive distillation in which the extractive agent is a higher boiling oxygenated, nitrogenous and/or sulfur containing organic compound or a mixture of two or more of these compound. Examples of effective agents are: dimethylsulfoxide; acetamide and ethylene glycol phenylether; adiponitrile; N,N-dimethylacetamide; dimethylformamide; and sulfolane.
    Type: Grant
    Filed: July 15, 1985
    Date of Patent: July 22, 1986
    Inventors: Lloyd Berg, Mark G. Vosburgh
  • Patent number: 4597834
    Abstract: Methyl acetate cannot be completely removed from methyl acetate - methanol mixtures by distillation because of the presence of the minimum binary azeotrope. Methyl acetate can be readily removed from mixtures containing it and methanol by using extractive distillation in which the extractive distillation agent is a higher boiling oxygenated, nitrogenous and/or sulfur containing organic compound or a mixture of these. Typical examples of effective agents are dimethylformamide; dimethylsulfoxide plus tetraethylene glycol, dimethylsulfoxide plus 1,5-pentanediol plus 1,6-hexanediol.
    Type: Grant
    Filed: February 17, 1984
    Date of Patent: July 1, 1986
    Inventors: Lloyd Berg, An-I Yeh
  • Patent number: 4592805
    Abstract: n-Propyl acetate cannot be completely removed from n-propyl acetate - n-propanol - water mixtures by distillation because of the presence of the minimum ternary azeotrope. n-Propyl acetate can be readily removed from mixtures containing it, n-propanol and water by using extractive distillation in which the extractive distillation agent is a higher boiling oxygenated, nitrogenous and/or sulfur containing organic compound or a mixture of these. Examples of effective agents are N,N-dimethylacetamide; acetamide and triethylene glycol; acetamide and N,N-dimethylacetamide and triethanolamine.
    Type: Grant
    Filed: December 14, 1984
    Date of Patent: June 3, 1986
    Inventors: Lloyd Berg, An-I Yeh
  • Patent number: 4584063
    Abstract: Acetone cannot be completely removed from acetone-methanol mixtures by distillation because of the presence of the minimum boiling azeotrope. Acetone can be readily separated from methanol by using extractive distillation in which the extractive agent is a higher boiling oxygenated, nitrogenous and/or sulfur-containing organic compound or a mixture of two or more of these. Typical examples of effective agents are: Glycerine, 1,5-Pentanediol, Dimethylsulfoxide, n-Hexanol, Dioctyl phthalate and N,N-Dimethylacetamide.
    Type: Grant
    Filed: June 28, 1982
    Date of Patent: April 22, 1986
    Inventors: Lloyd Berg, Karl J. Warren
  • Patent number: 4569726
    Abstract: Ethyl acetate cannot be completely removed from ethanol and water mixtures by distillation because of the presence of the minimum ternary azeotrope. Ethyl acetate can be readily removed from mixtures containing it, ethanol and water by using extractive distillation in which the extractive distillation agent is a higher boiling oxygenated, sulfur containing or nitrogenous organic compound or a mixture of these. Typical examples of effective agents are: 1,4-butanediol; ethylene glycol-1,5-pentanediol; propylene glycol-tetraethylene glycol-polyethylene glycol; glycerine-propylene glycol-tetraethylene glycol-1,4-butanediol.
    Type: Grant
    Filed: July 19, 1984
    Date of Patent: February 11, 1986
    Inventors: Lloyd Berg, Pisant Ratanapupech
  • Patent number: 4568427
    Abstract: A process for the continuous isolation of phthalic anhydride and maleic anhydride from the reaction gases obtained by catalytic oxidation of o-xylene or naphthalene with air, wherein the reaction gases are treated with a hydrocarbon of boiling range from 115.degree. to 175.degree. C. as the solvent in a column, and are then treated with an organic solvent of boiling range from 180.degree. to 290.degree. C. in a second column, the phthalic anhydride and maleic anhydride being isolated from the liquid bottom product of the first column.
    Type: Grant
    Filed: February 11, 1983
    Date of Patent: February 4, 1986
    Assignee: BASF Aktiengesellschaft
    Inventors: Eckehard Danz, Gerd Dumbgen, Ernest Miesen, Johannes E. Schmidt, Friedrich Wirth
  • Patent number: 4566948
    Abstract: Isopropyl ether cannot be completely removed from isopropyl ether-isopropanol-water mixtures by distillation because of the presence of the minimum ternary azeotrope. Isopropyl ether can be readily removed from mixtures containing it, isopropanol and water by using extractive distillation in which the extractive distillation agent is dimethylsulfoxide with or without a mixture of higher boiling oxygenated and/or nitrogenous organic compounds. Typical examples are dimethylsulfoxide; dimethylsulfoxide and ethylene glycol; dimethylsulfoxide, dimethylformamide and 1,4-butanediol.
    Type: Grant
    Filed: December 20, 1984
    Date of Patent: January 28, 1986
    Inventors: Lloyd Berg, An-I Yeh
  • Patent number: 4559109
    Abstract: A process for producing anhydrous ethanol from an ethanol-water mixture feedstock comprising subjecting the feedstock to distillation in a first distillation zone to produce an overhead vapor of from about 80 to about 90 weight percent ethanol, subjecting the thus produced overhead vapor to extractive distillation in an extractive distillation zone to produce anhydrous ethanol vapor overhead of about 99.5 weight percent ethanol and a solvent-rich bottom stream, and stripping the solvent-rich bottom stream and recycling the thus produced lean solvent bottom stream to the extractive distillation zone and recycling the thus produced overhead vapor stream to the first distillation zone. Also disclosed is a system for performing the process.
    Type: Grant
    Filed: March 31, 1983
    Date of Patent: December 17, 1985
    Assignee: Phillips Petroleum Company
    Inventors: Fu-Ming Lee, Robert H. Pahl
  • Patent number: 4559111
    Abstract: Production of essentially pure Z-11-hexadecenal by azeotropic distillation is described. Contacting a mixture of Z-11-hexadecenal, hexadecene and hexadecadiene with dimethylsulfoxide and subjecting the blend to azeotropic distillation allows for the removal of hydrocarbon impurities from the aldehyde. Contacting a mixture of Z-11-hexadecenal and hexadecenol with a C.sub.2 -C.sub.4 glycol and subjecting the blend to azeotropic distillation conditions allows for the recovery of a glycol-aldehyde azeotrope from which essentially pure aldehyde is readily recovered. A mixture comprising Z-11-hexadecenal, hexadecene, hexadecadiene and hexadecenol can be sequentially treated according to the above-described azeotropic distillation steps in order to provide essentially pure Z-11-hexadecenal.
    Type: Grant
    Filed: December 20, 1984
    Date of Patent: December 17, 1985
    Assignee: Phillips Petroleum Company
    Inventor: Charles A. Drake
  • Patent number: 4551208
    Abstract: Formic acid is recovered, by distillation, from its mixtures with solvents of the general formula I ##STR1## where R.sup.1 is hydrogen, methyl, ethyl or vinyl and R.sup.2 and R.sup.3 are each alkyl, cycloalkyl, aryl or aralkyl, or R.sup.2 and R.sup.3 together form a 1,4- or 1,5-alkylene group, in each case of not more than 8 carbon atoms, with the provisos that the sum of the number of carbon atoms in R.sup.2 and R.sup.3 is 7 to 14 and that only one of these radicals is aryl, by a method in which the distillation is carried out in the presence of a carboxamide II which is selected from the group consisting of formamide, acetamide, propionamide and the same compounds substituted by N-methyl or N,N-dimethyl, and which has a boiling point lower than that of the solvent I.
    Type: Grant
    Filed: May 25, 1984
    Date of Patent: November 5, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Kaspar Bott, Gerd Kaibel, Horst Hartmann, Rudolf Irnich, Horst Buelow
  • Patent number: 4549938
    Abstract: Methanol cannot be completely removed from methanol-methyl acetate mixtures by distillation because of the presence of the minimum binary azeotrope. Methanol can be readily removed from mixtures containing it and methyl acetate by using extractive distillation in which the extractive distillation agent is a higher boiling oxygenated or nitrogenous organic compound or a mixture of these. Typical examples of effective agents are: ethylene glycol phenyl ether, ethylene carbonate, nitromethane, 2-nitrotoluene, 1-nitropropane plus propylene carbonate.
    Type: Grant
    Filed: March 23, 1984
    Date of Patent: October 29, 1985
    Inventors: Lloyd Berg, An-I Yeh
  • Patent number: 4544454
    Abstract: Isopropyl ether cannot be completely removed from isopropyl ether - methyl ethyl ketone mixtures by distillation because of the presence of the minimum binary azeotrope. Isopropyl ether can be readily removed from mixtures containing it and methyl ethyl ketone by using extractive distillation in which the extractive distillation agent is a higher boiling oxygenated and/or nitrogenous organic compound or a mixture of these. Typical examples of effective agents are adiponitrile; ehtylene carbonate plus dimethylformamide; adiponitrile plus dimethylformamide plus glycerine.
    Type: Grant
    Filed: February 10, 1984
    Date of Patent: October 1, 1985
    Inventors: Lloyd Berg, An-I Yeh
  • Patent number: 4543164
    Abstract: Methyl acetate cannot be completely removed from methyl acetate-methanol mixtures by distillation because of the presence of the minimum binary azeotrope. Methyl acetate can be readily removed from mixtures containing it and methanol by using extractive distillation in which the extractive distillation agent is a higher boiling oxygenated, nitrogenous and/or sulfur containing organic compound or a mixture of these. Typical examples of effective agents are dimethylsulfoxide; glycerine plus propylene glycol; ethylene glycol plus DMSO plus 1,5-pentanediol. Methanol can be removed as the overhead product from methyl acetate when the extractive distillation agent is nitrobenzene, propylene carbonate or ethylene glycol phenyl ether.
    Type: Grant
    Filed: April 14, 1983
    Date of Patent: September 24, 1985
    Inventors: Lloyd Berg, An-I Yeh
  • Patent number: 4525245
    Abstract: n-Butyl acetate cannot be completely removed from n-butyl acetate - n-butanol - water mixtures by distillation because of the presence of the minimum ternary azeotrope. n-Butyl acetate can be readily removed from mixtures containing it, n-butanol and water by using extractive distillation in which the extractive distillation agent is a higher boiling oxygenated, nitrogenous and/or sulfur containing organic compound or a mixture of these. Typical examples of effective agents are dimethylsulfoxide; dimethylsulfoxide and 1,4-butanediol; dimethylsulfoxide, dimethylformamide and 1,6-hexanediol.
    Type: Grant
    Filed: May 7, 1984
    Date of Patent: June 25, 1985
    Inventors: Lloyd Berg, An-I Yeh
  • Patent number: 4514262
    Abstract: Benzene is virtually impossible to separate from similar close boiling non-aromatic hydrocarbons by conventional rectification or distillation. Benzene can be readily separated from similar boiling non-aromatic hydrocarbons by using extractive distillation in which the extractive agent is a mixture of benzoic acid, maleic anhydride and/or phthalic anhydride plus a suitable solvent. A typical mixture comprises phthalic anhydride, maleic anhydride and adiponitrile.
    Type: Grant
    Filed: August 2, 1982
    Date of Patent: April 30, 1985
    Inventor: Lloyd Berg
  • Patent number: 4513153
    Abstract: Tert.butyl alkyl ethers are produced from a C.sub.4 hydrocarbon feedstock containing isobutene, and the butene-1 is recovered at high purity by extractive distillation of the isobutene-free C.sub.4 hydrocarbon stream in the presence of a solvent chosen from acetone, acetonitrile, dimethylformamide, methanol, n-methylpyrrolidone, formylmorpholine and furfural.After removing the solvent, the extract is rectified, and the butene-1 separates as overhead product of high purity.
    Type: Grant
    Filed: May 3, 1983
    Date of Patent: April 23, 1985
    Assignee: Snamprogetti S.p.A.
    Inventor: Romedio Sandrin
  • Patent number: 4510022
    Abstract: Isopropyl ether cannot be completely removed from isopropyl ether-isopropanol-water mixtures by distillation because of the presence of the minimum ternary azeotrope. Isopropyl ether can be readily removed from mixtures containing it, isopropanol and water by using extractive distillation in which the extractive distillation agent is a higher boiling oxygenated, nitrogenous and/or sulfur containing organic compound or a mixture of these. Typical examples of effective agents are ethylene glycol; dimethylsulfoxide plus propylene glycol; dimethylsulfoxide plus dimethylformamide plus diethylene glycol diethyl ether.
    Type: Grant
    Filed: August 8, 1983
    Date of Patent: April 9, 1985
    Inventors: Lloyd Berg, An-I Yeh
  • Patent number: 4507176
    Abstract: n-Butyl acetate cannot be completely removed from n-butyl acetate-n-butanol--water mixtures by distillation because of the presence of the minimum ternary azeotrope. n-Butyl acetate can be readily removed from mixtures containing it, n-butanol and water by using extractive distillation in which the extractive distillation agent is a higher boiling oxygenated, nitrogenous and/or sulfur containing organic compound or a mixture of these. Typical examples of effective agents are N,N-dimethylacetamide, dimethylsulfoxide and acetamide, ethylene glycol propylene glycol, dimethylsulfoxide and acetamide.
    Type: Grant
    Filed: May 7, 1984
    Date of Patent: March 26, 1985
    Inventors: Lloyd Berg, An-I Yeh
  • Patent number: 4501645
    Abstract: Methanol cannot be completely removed from its mixture with acetone by distillation because of the presence of the minimum binary azeotrope. Methanol can be readily removed from mixtures containing it and acetone by using extractive distillation to bring off the methanol as overhead product in a rectification column by using extractive distillation in which the extractive distillation agent is an effective higher boiling organic compound or a mixture of these. Typical examples of effective agents are acetophenone, 3-pentanone, 2,4-pentanedione, ethylacetoacetate, 2-butanone plus benzil.
    Type: Grant
    Filed: November 1, 1983
    Date of Patent: February 26, 1985
    Inventors: Lloyd Berg, An-I Yeh
  • Patent number: 4490153
    Abstract: Low energy process for the production of gasoline-ethanol blends, comprising dehydrating the aqueous ethanolic product from a conventional fermentation process, preferably containing about 6 wt. % ethanol, so as to generate an aqueous ethanolic effluent containing about 90 wt. % ethanol; mixing the effluent with gasoline feedstock; chilling the resultant gasoline-aqueous ethanol mixture to a temperature of about -10.degree. F., without forming ice, thereby to form (1) a gasohol blend containing about 10 wt. % ethanol and (2) an aqueous stream comprising some ethanol and traces of gasoline; extracting the gasoline-containing aqueous stream with a minor stream of the fermentation ethanol product in order to recover the gasoline it contains; and recovering said blend to produce a gasohol product under-saturated with water at all operating temperatures above -10.degree. F.
    Type: Grant
    Filed: October 31, 1983
    Date of Patent: December 25, 1984
    Assignee: Lummus Crest Inc.
    Inventors: Morgan C. Y. Sze, George D. Suciu
  • Patent number: 4488937
    Abstract: m-Xylene is difficult to separate from o-xylene by conventional rectification or distillation because of the close proximity of their boiling points. m-Xylene can be readily separated from o-xylene by using extractive distillation in which the extractive agent is ethyl-2-hydroxybenzoate; propoxypropanol puls 1,4-butanediol; sulfolane plus dimethylsulfoxide plus ethyl benzoate.
    Type: Grant
    Filed: April 11, 1984
    Date of Patent: December 18, 1984
    Inventors: Lloyd Berg, An-I Yeh
  • Patent number: 4470881
    Abstract: A method for separating ethyl acetate from methyl ethyl ketone is described including distilling in an anhydrous condition a mixture of ethyl acetate-methyl ethyl ketone in a plate column in the presence of an effective amount of an organic extractive solvent which has the following properties: (1) is soluble in a boiling ethyl acetate-methyl ethyl ketone mixture; (2) does not form an azeotrope with ethyl acetate or methyl ethyl ketone; (3) boils higher than ethyl acetate and methyl ethyl ketone and (4) in combination with the ethyl acetate-methyl ethyl ketone mixture, results in a relative volatility of ethyl acetate to methyl ethyl ketone greater than 1.20.
    Type: Grant
    Filed: September 27, 1982
    Date of Patent: September 11, 1984
    Assignee: Celanese Corporation
    Inventor: Lloyd Berg
  • Patent number: 4459178
    Abstract: Isopropyl ether cannot be completely removed from isopropyl ether - methyl ethyl ketone mixtures by distillation because of the presence of the minimum binary azeotrope. Isopropyl ether can be readily removed from mixtures containing it and methyl ethyl ketone by using extractive distillation in which the extractive distillation agent is a higher boiling oxygenated, nitrogenous and/or sulfur containing organic compound or a mixture of these. Typical examples of effective agents are sulfolane; ethylene carbonate plus dimethylsulfoxide; adiponitrile plus dimethylformamide plus glycerine.
    Type: Grant
    Filed: April 25, 1983
    Date of Patent: July 10, 1984
    Inventors: Lloyd Berg, An-I Yeh
  • Patent number: 4459179
    Abstract: Isopropyl ether cannot be completely removed from isopropyl ether-acetone mixtures by distillation because of the presence of the minimum binary azeotrope. Isopropyl ether can be readily removed from mixtures containing it and acetone by using extractive distillation in which the extractive distillation agent is a higher boiling oxygenated or nitrogenous organic compound or a mixture of these. Typical examples of effective agents are: dimethylsulfoxide; sulfolane and propylene glycol; glycerine, ethylene glycol and adiponitrile.
    Type: Grant
    Filed: January 6, 1983
    Date of Patent: July 10, 1984
    Inventors: Lloyd Berg, An-I Yeh
  • Patent number: 4419188
    Abstract: Thermally coupled extractive distillation; a feed stock (for example, a C4 or C5 cut from an ethylene plant) is distilled by thermally coupled extractive distillation to remove paraffins and mono-olefins as a raffinate stream, as well as acetylenic hydrocarbons in a separate steam, thus segregating the C4 or C5 diolefin, the process using extraction solvents such as acetonitrile (ACN), dimethyl formamide (DMF), furfural, acetone, dimethylacetamide or N-methyl-2-pyrrolidone mixed with 0-12 weight percent of water, a bottoms stream of virtually acetylene free solvent further being produced; thermally coupled extractive distillation utilizing one to three coupled vessels to produce at least two and preferably three discrete, different volatility streams therefrom, as well as an extractive solvent recycle stream.
    Type: Grant
    Filed: February 22, 1982
    Date of Patent: December 6, 1983
    Inventor: Thomas F. McCall
  • Patent number: 4401517
    Abstract: A vapor-liquid extractive distillation process utilizing a dialkyl sulfone containing 4 to 8 carbon atoms per molecule and at least one percent water as the solvent. The process according to this invention is of particular applicability in separating aromatics from nonaromatics in a BTX stream. The solvent system operates particularly well with relatively large amounts of water.
    Type: Grant
    Filed: November 20, 1981
    Date of Patent: August 30, 1983
    Assignee: Phillips Petroleum Company
    Inventor: Fu-Ming Lee
  • Patent number: 4399307
    Abstract: The distillation of 2,2'bis(4-aminocyclohexyl)propane to yield high purity product is effectively carried out using high boiling organic solvents.
    Type: Grant
    Filed: March 11, 1982
    Date of Patent: August 16, 1983
    Assignee: Phillips Petroleum Company
    Inventor: Tod K. Shioyama
  • Patent number: 4379028
    Abstract: Ethyl acetate cannot be completely removed from ethanol and water mixtures by distillation because of the presence of the minimum ternary azeotrope. Ethyl acetate can be readily removed from mixtures containing it, ethanol and water by using extractive distillation in which the extractive distillation agent is a higher boiling oxygenated of nitrogenous organic compound or a mixture of these. Typical examples of effective agents are: dimethylsulfoxide, glycerine and diethylene glycol, 1-naphthol, hydroquinone and N,N-dimethylformamide.
    Type: Grant
    Filed: March 30, 1982
    Date of Patent: April 5, 1983
    Inventors: Lloyd Berg, Pisant Ratanapupech