Ester Patents (Class 203/60)
  • Patent number: 4673466
    Abstract: n-Hexyl alcohol 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 alcohol can be readily removed from mixtures containing it, n-hexyl acetate and water by using extractive distillation in which the extractive distillation agent is a benzoate or a mixture of benzoates with higher boiling organic compounds. Typical examples of effective agents are benzyl benzoate; methyl benzoate and adiponitrile; ethyl benzoate, benzyl benzoate and methyl salicylate.
    Type: Grant
    Filed: January 27, 1986
    Date of Patent: June 16, 1987
    Inventor: Lloyd Berg
  • 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: 4671857
    Abstract: The distillative separation of methacrylic acid from isobutyric acid is significantly improved by the introduction into the distillation system of a third component selected from the group consisting of methyl methacrylate, methyl isobutyrate and dimethylformamide.
    Type: Grant
    Filed: September 26, 1986
    Date of Patent: June 9, 1987
    Assignee: Eastman Kodak Company
    Inventor: Kris A. Johnson
  • 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: 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: 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: 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: 4654123
    Abstract: Water cannot be completely removed from ethanol by distillation because of the presence of the minimum azeotrope. Ethanol can be readily dehydrated by using extractive distillation in which the water is removed as overhead product and the ethanol and extractive agent as bottoms and subsequently separated by conventional rectification. Typical examples of suitable extractive agents are hexahydrophthalic anhydride; methyl tetrahydrophthalic anhydride and pentanol-1; trimellitic anhydride, ethyl salicylate and resorcinol.
    Type: Grant
    Filed: January 2, 1986
    Date of Patent: March 31, 1987
    Inventors: Lloyd Berg, An-I Yeh
  • Patent number: 4642167
    Abstract: Isobutyl acetate cannot be completely removed from isobutyl acetate--isobutanol--water mixtures by distillation because of the presence of the minimum ternary azeotrope. 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 N,N-dimethylacetamide; dimethylformamide and dimethylsulfoxide; acetamide, dimethylformamide and dipropylene glycol.
    Type: Grant
    Filed: March 7, 1985
    Date of Patent: February 10, 1987
    Inventors: Lloyd Berg, An-I Yeh
  • 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: 4631115
    Abstract: Water cannot be completely removed from ethanol by distillation because of the presence of the minimum azeotrope. Ethanol can be readily dehydrated by using extractive distillation in which the water is removed as overhead product and the ethanol and extractive agent as bottoms and subsequently separated by conventional rectification. Typical examples of suitable extractive agents are methyl benzoate; trimellitic anhydride and methyl benzoate; dipropylene glycol dibenzoate, ethyl salicylate and resorcinol.
    Type: Grant
    Filed: December 23, 1985
    Date of Patent: December 23, 1986
    Inventors: Lloyd Berg, An-I Yeh
  • Patent number: 4629533
    Abstract: A process for recovering 3-methyl-1-butene from a hydrocarbon stream by treating the stream with a dimethylformamide/sulfolane solvent mixture to remove compounds which form azeotropes with 3-methyl-1-butene and separating the remaining stream.
    Type: Grant
    Filed: January 31, 1985
    Date of Patent: December 16, 1986
    Assignee: Phillips Petroleum Company
    Inventor: Charles A. Drake
  • 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: 4576683
    Abstract: A method for separating carboxylic acids from mixtures with non-acids by an extractive distillation method using a lactam with a 5- or 6-membered ring, preferably N-methyl-2-pyrrolidone, as an extractant to extract the acids from the mixture with non-acids, followed by separating the extracted acids from the extractant by rectification.
    Type: Grant
    Filed: June 6, 1984
    Date of Patent: March 18, 1986
    Assignee: Badger B.V.
    Inventor: Lester R. Cohen
  • 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: 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: 4556461
    Abstract: A process for separating a butene-1/isobutene mixture from a C.sub.4 hydrocarbon fraction is provided which comprises subjecting the C.sub.4 hydrocarbon fraction to extractive distillation using a polar solvent to separate components predominantly containing 1,3-butadiene as an extract and obtain an overhead containing butanes, butene-1, isobutene and butene-2 as main components and being substantially free from C.sub.3 -C.sub.4 diolefinic and acetylenic hydrocarbons, feeding the overhead into a first distillation column, removing isobutane as an overhead component from the first distillation column, feeding high-boiling components from the bottom of the first distillation column to a second distillation column, removing n-butane and butene-2 from the bottom of the second distillation column, and obtaining highly pure butene-1 and isobutene from its top.
    Type: Grant
    Filed: December 1, 1982
    Date of Patent: December 3, 1985
    Assignee: Nippon Zeon Co., Ltd.
    Inventors: Shunichiro Ogura, Masamichi Soumai
  • Patent number: 4555312
    Abstract: A process for separating a butene-1/isobutene mixture from a C.sub.4 hydrocarbon fraction is provided which comprises subjecting the C.sub.4 hydrocarbon fraction to extractive distillation using a polar solvent to separate components predominantly containing 1,3-butadiene as an extract bottom and obtain an overhead containing butanes, butene-1, isobutene and butene-2 as main components and being substantially free from C.sub.3 -C.sub.4 diolefinic and acetylenic hydrocarbons, feeding the overhead into a first distillation column, removing n-butane and butene-2 as bottoms from the column, feeding low-boiling components from the top of the column into a second distillation column, removing isobutane from the top of the second distillation column, and obtaining highly pure butene-1 and isobutene from its bottom.
    Type: Grant
    Filed: November 23, 1982
    Date of Patent: November 26, 1985
    Assignee: Nippon Zeon Co. Ltd.
    Inventors: Shunichiro Ogura, Masamichi Soumai
  • 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: 4551207
    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, nitrogenous and/or sulfur containing compound or a mixture of these. Typical examples of effective agents are: dimethylsulfoxide; sulfolane and propylene glycol; adiponitrile, glycerine and ethylene glycol.
    Type: Grant
    Filed: February 3, 1984
    Date of Patent: November 5, 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: 4532011
    Abstract: Vinylaromatic compounds are stabilized against undesired polymerization by adding to the vinylaromatic compounds small amounts of zinc or nickel salts of dialkyl dithiocarbamates, specifically p-diisopropenylbenzene can be stabilized by the use of zinc dibutyldithiocarbamate.
    Type: Grant
    Filed: March 2, 1984
    Date of Patent: July 30, 1985
    Assignee: The Goodyear Tire & Rubber Company
    Inventor: Howard A. Colvin
  • Patent number: 4532012
    Abstract: Phenol containing MBF impurity is distilled in the presence of water and an extraction solvent for MBF (preferably AMS and/or cumene) to recover a phenol bottoms having reduced impurities. The use of solvent permits a reduction in the amount of water used, which reduces the amount of phenol in the overhead, thereby lowering costs.
    Type: Grant
    Filed: October 31, 1983
    Date of Patent: July 30, 1985
    Assignee: The Lummus Company
    Inventors: Ali M. Khonsari, George D. Suciu
  • 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: 4515661
    Abstract: A process for separating highly pure butene-2 and butene-1 from a C.sub.4 hydrocarbon fraction containing isobutane, n-butane, butene-1, butene-2, and at least one diolefinic hydrocarbon and/or at least one acetylenic hydrocarbon, which comprises, (1) as a step A, treating the C.sub.
    Type: Grant
    Filed: September 21, 1982
    Date of Patent: May 7, 1985
    Assignee: Nippon Zeon Co. Ltd.
    Inventors: Shunichiro Ogura, Masamichi Soumai
  • 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: 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: 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: 4464229
    Abstract: In a process for producing an acrylic or methacrylic ester by esterifying acrylic or methacrylic acid with a lower aliphatic alcohol having 1 to 3 carbon atoms in the presence of an acidic catalyst, the improvement which comprises(1) distilling the resulting esterification reaction mixture while feeding the acrylic or methacrylic ester into a distillation column from outside the system, thereby to yield as a distillate a mixture composed of the acrylic or methacrylic ester, water and the unreacted alcohol and being substantially free from acrylic or methacrylic acid, and (2) recycling the residue in the distillation column, from which the ester and water formed have been substantially removed, to the esterification reaction in such a proportion that the mole ratio of acrylic or methacrylic acid to the alcohol in the entire starting materials fed to the esterification reaction is kept at 1:0.5-1.0.
    Type: Grant
    Filed: June 29, 1982
    Date of Patent: August 7, 1984
    Assignee: Nippon Shokubai Kagaku Kogyo Co. Ltd.
    Inventors: Takahisa Sato, Sumio Nakashima, Masao Baba
  • 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: 4447318
    Abstract: In a method for separating a hydrocarbon mixture into relatively difficultly soluble hydrocarbons and relatively easily soluble hydrocarbons by extractive distillation using a polar solvent comprising feeding the starting hydrocarbon mixture to at least two evaporators, an extractive distillation column, a stripping column and a rectifying column; the improvement wherein(1) the polar solvent discharged at a high temperature from the bottom of the stripping column is recycled to the extractive distillation column after it has been cooled to a suitable temperature by giving up heat to a reboiler of the extractive distillation column, a reboiler of the rectifying column and successively to the two or more evaporators, and(2) the starting hydrocarbon mixture is divided into two or more streams and heated in two or more evaporators, one stream being evaporated in a first evaporator to a pressure necessary for introduction into the extractive distillation column and then fed to the extractive distillation column, a
    Type: Grant
    Filed: March 28, 1983
    Date of Patent: May 8, 1984
    Assignee: Nippon Zeon Co., Ltd.
    Inventors: Shunichiro Ogura, Masafumi Miyamoto
  • Patent number: 4439278
    Abstract: The present invention provides an improvement in methods for preparing and processing ethylenically unsaturated aromatic monomer. The improvement comprises employing 3,5-dinitrosalicylic acid or a derivative or isomer thereof as a process inhibitor. The process inhibitor is present in a concentration of about 50 to 3000 ppm, preferably about 250 to 2,000 ppm, and most preferably about 500 to 1,000 ppm.
    Type: Grant
    Filed: April 28, 1983
    Date of Patent: March 27, 1984
    Assignee: Eastman Kodak Company
    Inventors: Ted L. Douglas, Ambrose J. Clonce, Glenn C. Jones
  • Patent number: 4421607
    Abstract: A process of extractive distillation for separating components easily soluble in a polar solvent from at least two hydrocarbon mixtures having different contents of the easily soluble components by extractive distillation using said polar solvent, which comprises feeding a hydrocarbon mixture containing a larger amount of the easily soluble components, as a gas, into the middle or lower portion of an extractive distillation column, feeding a hydrocarbon mixture containing a smaller amount of the easily soluble components, as a liquid, to the upper portion of the extractive distillation column, and subjecting them to extractive distillation.
    Type: Grant
    Filed: February 1, 1983
    Date of Patent: December 20, 1983
    Assignee: Nippon Zeon Co. Ltd.
    Inventor: Shunichiro Ogura
  • Patent number: 4416734
    Abstract: A process for the separation of a dissolved solid from an aqueous solution containing it, comprising the steps of (a) adding thereto an organic liquid which is a poor solvent for the dissolved solid and which forms an azeotrope with water, (b) subjecting the mixture to azeotropic distillation to separate at least a major portion of the water, (c) cooling the mixture thereby causing substantially complete separation of the dissolved solids, and (d) separating same from the mother liquor.
    Type: Grant
    Filed: May 11, 1981
    Date of Patent: November 22, 1983
    Assignee: Angus Chemical Company
    Inventor: Martin J. Jacobs
  • 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
  • Patent number: 4370491
    Abstract: A process for the preparation of acetic acid esters CH.sub.3 --CO--O--R.sup.1 (I, R.sup.1 =an organic radical other than methyl and ethyl) by alkali-catalyzed trans-esterification of an acetic acid ester CH.sub.3 --CO--O--R.sup.2 (II, R.sup.2 =methyl or ethyl) with an alcohol R.sup.1 --OH (III), accompanied by elimination of the alcohol R.sup.2 --OH (IV), wherein(a) the trans-esterification reaction is carried out in the middle section K.sub.M of a distillation column K, the alcohol III being fed as liquid into the upper zone and the ester II into the lower zone of K.sub.M,(b) the alkaline catalyst is introduced into the upper part K.sub.U of K,(c) the alcohol IV, or a mixture of IV and the ester II, is taken off the top of the column,(d) the mixture obtained from (c) (unless the alcohol IV alone is obtained) is separated in the column section K.sub.U or in a stripper column K.sub.S into IV and the azeotrope of II and IV, and the latter is recycled to the lower zone of K.sub.
    Type: Grant
    Filed: May 14, 1981
    Date of Patent: January 25, 1983
    Assignee: BASF Aktiengesellschaft
    Inventors: Kaspar Bott, Gerd Kaibel, Herwig Hoffmann, Rudolf Irnich, Eberhard Schaefer
  • Patent number: 4363704
    Abstract: Toluene is virtually impossible to separate from similar boiling non-aromatic hydrocarbons by conventional rectification or distillation. Toluene can be readily separated from similar boiling non-aromatic hydrocarbons by using extractive distillation in which the extractive agent is a mixture of phthalic anhydride and/or maleic anhydride plus a suitable solvent. A typical mixture comprises phthalic anhydride, maleic anhydride and glycerol triacetate.
    Type: Grant
    Filed: November 20, 1981
    Date of Patent: December 14, 1982
    Inventor: Lloyd Berg
  • Patent number: 4358609
    Abstract: A process for the recovery of carboxylic acids from mixtures containing glycol esters derived from these acids. The process comprises reacting these mixtures at boiling with water to form carboxylic acid and entraining the carboxylic acid formed by means of the water by azeotropic distillation, so as to separate off a mixture of carboxylic acid and water. This mixture is subjected to extractive distillation by means of an organic solvent which is insoluble in water and in which water is insoluble. A mixture of water and organic solvent is thereby separated from a solution of carboxylic acid in the organic solvent.
    Type: Grant
    Filed: October 1, 1980
    Date of Patent: November 9, 1982
    Assignee: Propylox (Societe Anonyme)
    Inventor: Nicolas Hardy
  • Patent number: 4345976
    Abstract: The invention involves a process for substantially separating the components of mixtures of substances at least one of which is of low volatility while the other is of low or no volatility, the process using a compressed gas under supercritical conditions and an entrainer which increases the concentration of said mixture in the gaseous phase as well as the separation factor between the components to be separated. The process operates in two distillation zones the first of which substantially separates the components of low volatility in a process similar to a rectification process while the second distillation zone separates the top product of the first distillation zone from the gas with the aid of the entrainer which is condensed partially and in this state is passed in countercurrent to the gas carrying the separated component of low volatility.
    Type: Grant
    Filed: February 7, 1979
    Date of Patent: August 24, 1982
    Assignee: Siegfried Peter
    Inventors: Siegfried Peter, Gerd Brunner, Rolf Riha
  • Patent number: 4344897
    Abstract: In a process for the continuous preparation of pure organic solutions of percarboxylic acids having 2 to 5 carbon atoms, by(a) contacting aqueous hydrogen peroxide with a carboxylic acid containing 2 to 5 carbon atoms in the presence of an acid catalyst at a feed molar ratio of H.sub.2 O.sub.2 to carboxylic acid of 0.
    Type: Grant
    Filed: December 13, 1979
    Date of Patent: August 17, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Ralf Goedecke, Willi Hofen, Hermann Seifert, Gerd Siekmann
  • Patent number: 4342627
    Abstract: The present invention relates to a continuous process for producing substantially anhydrous alcohols from aqueous solutions thereof by distilling a mixture of aqueous alcohol and an entrainer to a drying column withdrawing an azeotrope as a distillate and continuously recovering anhydrous alcohol with less than 0.1% by weight of water from the base of the drying column. The improvement resides in feeding the distillate to a condenser and introducing (a) the condensate therefrom in a substantially non-turbulent state into a decanter at a point close to the interface between the aqueous and organic phases present therein and (b) a specified amount of water, which is less than 0.25 volumes per volume of the anhydrous alcohol recovered, into the drying column at a point adjacent to that at which the organic hydrocarbon phase is returned as reflux.
    Type: Grant
    Filed: April 16, 1981
    Date of Patent: August 3, 1982
    Assignee: BP Chemicals Limited
    Inventors: Charles Cane, Bertram Yeomans