Alcohol Or Ether Patents (Class 203/63)
  • Patent number: 4897161
    Abstract: Vinyl acetate cannot be easily removed from ethyl acetate by distillation because of the closeness of their boiling points. Vinyl acetate can be readily separated from ethyl acetate by means of extractive distillation using certain glycols or glycol ethers. Typical effective agents are 2-methyl -2,4-pentanediol, 1,3-butanediol, ethylene glycol methyl ether and diethylene glycol ethyl ether.
    Type: Grant
    Filed: March 20, 1989
    Date of Patent: January 30, 1990
    Assignee: Lloyd Berg
    Inventors: Lloyd Berg, Marc W. Paffhausen
  • Patent number: 4877490
    Abstract: Formic acid cannot be completely removed from formic acid and water mixtures by distillation because of the presence of the maximum azeotrope. Formic acid can be readily removed from formic acid--water mixtures by extractive distillation in which extractive agent is a dicarboxylic acid mixed with certain high boiling organic compounds. Examples of effective agents are: itaconic acid and diethylene glycol diethyl ether; azelaic acid, heptanoic acid and 2-hydroxyacetophenone.
    Type: Grant
    Filed: January 23, 1989
    Date of Patent: October 31, 1989
    Assignee: Lloyd Berg
    Inventors: Lloyd Berg, Kraig M. Wendt, Rudolph J. Szabados
  • Patent number: 4877491
    Abstract: Meta and para-diisopropylbenzenes cannot be easily separated from each other by distillation because of the closeness of their vapor pressures. m-Diisopropylbenzene can be readily removed from p-diisopropylbenzene by azeotropic distillation using certain ketones. Typical effective azeotropic distillation agents are acetophenone, 2-undecanone and acetonyl acetone.
    Type: Grant
    Filed: November 14, 1988
    Date of Patent: October 31, 1989
    Assignee: Lloyd Berg
    Inventor: Lloyd Berg
  • Patent number: 4874473
    Abstract: Diastereomers can be separated with good industrial success with the aid of extractive distillation. The separation process is characterized in that an auxiliary which changes the partial pressure of the various diastereomers to be separated to a different degree and thus allows easier separation of the diastereomers by distillation is added during the distillation. Using the present process diastereomic cis/trans-permetric acid methyl esters and mixtures of menthol and isomenthol can be separated with isolation of 99% pure product.
    Type: Grant
    Filed: April 16, 1987
    Date of Patent: October 17, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Dieter Arlt, Ulrich Schwartz, Hans-Walter Brandt, Wolfgang Arlt, Andreas Nickel
  • Patent number: 4865973
    Abstract: A process for producing a variety of chemical products, e.g., ethanol, by fermentation in which the product is removed from the fermentation medium as it is formed by liquid-liquid extraction using an extractant for the product which is immiscible with water. The extractant employed is chosen from the following groups: (A) double bond unsaturated aliphatic alcohols having 12 or more carbon atoms; (B) saturated branched chain aliphatic alcohols having 14 or more carbon atoms or mixtures thereof; (C) double bond unsaturated aliphatic acids having 12 or more carbon atoms; (D) aliphatic and aromatic mono-, di- or tri-esters having 12 or more carbon atoms, other than dibutyl phthalate; (E) aliphatic noncyclic ketones and aliphatic aldehydes having 12 or more carbon atoms; and (F) mixtures of extractants from groups (A) to (E) above or mixtures of at least one of the above extractants and at least one other extractant.
    Type: Grant
    Filed: August 13, 1986
    Date of Patent: September 12, 1989
    Assignee: Queen's University at Kingston
    Inventors: Finn Kollerup, Andrew J. Daugulis
  • Patent number: 4855531
    Abstract: Meta and para-diisopropylbenzene cannot be easily separated from each other by distillation because of the closeness of their vapor pressures. m-Diisopropylbenzene can be easily removed from p-diisopropylbenzene by azeotropic distillation using certain ethers. Typical effective azeotropic distillation agents are diethylene glycol diethyl ether and dipropylene glycol dimethyl ether.
    Type: Grant
    Filed: November 29, 1988
    Date of Patent: August 8, 1989
    Assignee: Lloyd Berg
    Inventor: Lloyd Berg
  • Patent number: 4851087
    Abstract: Meta and para-diisopropylbenzenes cannot be easily separated from each other by distillation because of the closeness of their vapor pressures. m-Diisopropylbenzene can be readily removed from p-diisopropylbenzene by azeotropic distillation using certain nitrogenous compounds. Typical effective azeotropic distillation agents are ethanolamine and benzonitrile.
    Type: Grant
    Filed: November 28, 1988
    Date of Patent: July 25, 1989
    Assignee: Lloyd Berg
    Inventor: Lloyd Berg
  • Patent number: 4840707
    Abstract: 3-Methyl-2-butanone cannot be removed from 3-methyl-2-butanone and formic acid mixtures by distillation because of the presence of the maximum azeotrope between 3-methyl-2-butanone and formic acid. 3-Methyl-2-butanone can be readily removed from 3-methyl-2-butanone - formic acid mixtures by extractive distillation in which the extractive agent is dimethylacetamide, dimethylformamide or these with certain high boiling organic compounds.
    Type: Grant
    Filed: December 30, 1988
    Date of Patent: June 20, 1989
    Assignee: Lloyd Berg
    Inventors: Lloyd Berg, Richard R. Rall
  • Patent number: 4826576
    Abstract: Isopropyl acetate cannot be completely removed from isopropyl acetate--isopropanol--water mixtures by distillation because of the presence of the minimum ternary azeotrope. Isopropyl acetate can be readily removed from mixtures containing it, isopropanol and water by using extractive distillation in which the extractive agent is a mixture of a polyol and one or higher boiling oxygenated, nitrogenous and/or sulfur containing organic compounds. Typical examples of effective agents are 1,3-butanediol and dimethylsulfoxide; 1,2,6-hexanetriol, dimethylsulfoxide and dimethylformamide.
    Type: Grant
    Filed: June 2, 1986
    Date of Patent: May 2, 1989
    Assignee: Lloyd Berg
    Inventors: Lloyd Berg, An-I Yeh
  • Patent number: 4806209
    Abstract: Dioxane cannot be completely removed from dioxane and formic acid mixtures by distillation because of the presence of the maximum azeotrope. Dioxane can be readily removed from dioxane - formic acid mixtures by extractive distillation in which the extractive agent is dimethylsulfoxide, either alone or admixed with certain high boiling organic compounds. Examples of effective agents are dimethylsulfoxide; DMSO and octanoic acid; DMSO, neodecanoic acid and methyl salicylate.
    Type: Grant
    Filed: April 25, 1988
    Date of Patent: February 21, 1989
    Inventors: Lloyd Berg, Rudolph J. Szabados
  • Patent number: 4801357
    Abstract: Dioxane cannot be completely removed from dioxane and acetic acid mixtures by distillation because of the presence of the maximum azeotrope. Dioxane can be readily removed from dioxane-acetic acid mixtures by extractive distillation in which the extractive agent is dimethylsulfoxide, either alone or mixed with certain high boiling organic compounds. Examples of effective agents are dimethylsulfoxide; DMSO and octanoic acid; DMSO, hexanoic acid and isophorone.
    Type: Grant
    Filed: April 1, 1988
    Date of Patent: January 31, 1989
    Inventors: Lloyd Berg, Rudolph J. Szabados
  • Patent number: 4801358
    Abstract: Dioxane cannot be completely removed from dioxane and acetic acid mixtures by distillation because of the presence of the maximum azeotrope. Dioxane can be readily removed from dioxane - acetic acid mixtures by extractive distillation in which the extractive agent is N,N-dimethylacetamide or dimethylformamide, either alone or mixed with certain high boiling organic compounds. Examples of effective agents are N,N-dimethylacetamide; dimethylformamide and heptanoic acid; N,N-dimethylacetamide, heptanoic acid and diethylene glycol diethyl ether.
    Type: Grant
    Filed: July 28, 1988
    Date of Patent: January 31, 1989
    Inventors: Lloyd Berg, Rudolph J. Szabados
  • Patent number: 4793901
    Abstract: 2-Pentanone cannot be completely removed from 2-pentanone and formic acid mixtures by distillation because of the presence of the maximum azeotrope. 2-Pentanone can be readily removed from 2-pentanone formic acid mixtures by extractive distillation in which the extractive agent is dimethylsulfoxide, either alone or mixed with certain high boiling organic compounds. Examples of effective agents are dimethylsulfoxide; DMSO and octanoic acid; DMSO, hexanoic acid and isophorone.
    Type: Grant
    Filed: April 11, 1988
    Date of Patent: December 27, 1988
    Assignee: Hoechst Celanese Chemical Co.
    Inventors: Lloyd Berg, Rudolph J. Szabados
  • Patent number: 4740273
    Abstract: A process for purifying diethoxymethane from a mixture containing ethanol and, optionally, water. The process involves the addition of an amount of water, DEM, or an appropriate mixture of any two or three of water, DEM and ethanol that is effective in moving the mixture into the two liquid phase region on an equilibrium tie-line which crosses the critical distillation boundary without the need for additional azeotrope-forming agents such as cyclohexane.
    Type: Grant
    Filed: April 16, 1987
    Date of Patent: April 26, 1988
    Assignee: Eastman Kodak Company
    Inventors: Daniel L. Martin, Peter W. Raynolds
  • 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: 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: 4698137
    Abstract: Isopropyl acetate cannot be completely removed from isopropyl acetate - isopropanol - water mixtures by distillation because of the presence of the minimum ternary azeotrope. Isopropyl acetate can be readily removed for mixtures containing it, isopropanol and water by using extractive distillation in which the extractive agent is higher boiling oxygenated or nitrogenous organic compound or a mixture of these. Typical examples of effective agents are dimethylformamide; dimethylformamide and triethanolamine; N,N-dimethylacetamide and N-methyl pyrrolidone.
    Type: Grant
    Filed: March 5, 1986
    Date of Patent: October 6, 1987
    Inventor: Lloyd Berg
  • Patent number: 4693789
    Abstract: Isopropyl acetate cannot be completely removed from isopropyl acetate - isopropanol - water mixtures by distillation because of the presence of the minimum ternary azeotrope. Isopropyl acetate can be readily removed from mixtures containing it, isopropanol and water by using extractive distillation in which the extractive agent is a higher boiling oxygenated or nitrogenous organic compound or a mixture of these. Typical examples of effective agents are diethanolamine; ethanolamine and N-methyl pyrrolidone; triethanolamine and N-methyl pyrrolidone.
    Type: Grant
    Filed: March 5, 1986
    Date of Patent: September 15, 1987
    Inventors: Lloyd Berg, An-I Yeh
  • Patent number: 4686010
    Abstract: The production of solutions of hydrogen peroxide in phenol or its derivatives, e.g. hydrocarbyl substituted phenols, halo substituted phenols or phenol ethers, is carried out in a single step. Practically no loss of hydrogen peroxide occurs since a total distillation of hydrogen peroxide together with phenol or phenol derivative is avoided. Simultaneously the solutions obtained are practically free from water. The mixture of phenol or phenol derivative and aqueous hydrogen peroxide is treated with a material that boils below the boiling point of hydrogen peroxide, phenol or phenol derivative or forms an azeotrope with water that boils below the boiling point of hydrogen peroxide, phenol or phenol derivative and the water removed as an azeotrope. The solution of hydrogen peroxide in phenol or phenol derivative which remains behind is suitable for carrying out oxidation reactions and above all, also for hydroxylation reactions.
    Type: Grant
    Filed: September 7, 1984
    Date of Patent: August 11, 1987
    Assignee: Degussa Aktiengesellschaft
    Inventors: Karlheinz Drauz, Axel Kleemann
  • 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: 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: 4664755
    Abstract: Process for the purification of crude .beta.-phenylethyl alcohol by azeotropic distillation in the presence of alkanolamines in which the alkylene chain contains 2 to 4 carbon atoms and is optionally substituted by 1 to 4 C.sub.1 -C.sub.3 -alkyl groups.
    Type: Grant
    Filed: November 27, 1985
    Date of Patent: May 12, 1987
    Assignee: Haarman & Reimer GmbH
    Inventors: Jurgen Nienhaus, Rudolf Hopp
  • 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: 4652343
    Abstract: The separation of homozeotropic mixtures of a paraffin or paraffins of 6-14 carbon atoms and an alcohol or alcohols of 4-8 carbon atoms is conducted in two rectification steps. In a first step, rectification is carried out in the presence of water as the azeotropic agent, and the resultant distillate, after condensation, is separated into two liquid phases. The thus-obtained organic phase is rectified in a further step without the addition of water, and the head product consisting of an alcohol/paraffin mixture is recycled into the first step. The paraffin or paraffins and the alcohol or alcohols are obtained in the lower section of the individual rectifying step or steps. The water which may be present in the starting mixture is removed from the cycle. Low-boiling paraffins and/or low-boiling alcohols are suitable as additional azeotropic agents.
    Type: Grant
    Filed: April 17, 1985
    Date of Patent: March 24, 1987
    Assignee: Chemische Werke Huls Aktiengesellschaft
    Inventor: Srinivasan Sridhar
  • Patent number: 4645570
    Abstract: For the distillation of a stream consisting essentially of alcohols of 6-20 carbon atoms, water and methanol, the methanol is first separated from the homogeneous, aqueous solution as the overhead product by distillation under a head pressure of 500-1,000 mbar. The bottoms discharge is mechanically separated under normal pressure and at a temperature of 5.degree.-95.degree. C. in a phase separator to obtain a discrete water phase preferably containing at least two thirds of the feedstream water. The remaining organic phase is then transferred from the phase separator into a second distillation column and the organic phase is dewatered in the latter at 100-500 mbar. The head product from the second column is conducted to a second phase separator; the aqueous phase is separated therein at a temperature of 5.degree.-95.degree. C. and optionally returned into the first phase separator. The bottom product from the second distillation column is passed into a downstream distillation stage wherein the C.sub.6 to C.
    Type: Grant
    Filed: October 19, 1984
    Date of Patent: February 24, 1987
    Assignee: Huels Aktiengesellschaft
    Inventors: Srinivasan Sridhar, Manfred Hartmann
  • 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: 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: 4615771
    Abstract: A method for the separation of bis-(2-aminoethyl)ether from N-(2-methoxyethyl)morpholine via azeotropic distillation using an entrainer such as monoethanolamine is described. The N-(2-methoxyethyl)morpholine is selectively removed by the monoethanolamine. The N-(2-methoxyethyl)morpholine is then separated from the monoethanolamine by liquid-liquid extraction using a non polar hydrocarbon or aromatic extraction solvent and distillation.The N-(2-methoxyethyl)morpholine-monoethanolamine stream previously had no economic use. The separation is now economically effected and the N-(2-methoxyethyl)morpholine used as a polyurethane catalyst.
    Type: Grant
    Filed: January 13, 1986
    Date of Patent: October 7, 1986
    Assignee: Texaco Inc.
    Inventors: Robert L. Zimmerman, Roger G. Duranleau
  • 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: 4585526
    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 comprises propoxypropanol; propoxypropanol and 1,4-butanediol; ethyl benzoate and ethylene glycol phenyl ether and benzyl alcohol.
    Type: Grant
    Filed: October 1, 1984
    Date of Patent: April 29, 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: 4582570
    Abstract: Improvement in an azeotropic distillation process, the improvement being the use of an entrainer characterized in that it is an organic compound in which one or more hydrogen atoms are replaced by halogen atoms, including at least one fluorine atom; it is miscible, under process conditions, with the organic compound being dehydrated; its volatility is sufficiently close to the volatility of the organic compound being dehydrated such that, under the process conditions, it forms an azeotrope with the organic compound; it is less miscible, under process conditions, with water than is the corresponding organic compound in which the halogen atoms are replaced with hydrogen atoms; and it is chemically stable under the process conditions.
    Type: Grant
    Filed: June 20, 1983
    Date of Patent: April 15, 1986
    Assignee: Merix Corporation
    Inventor: Thomas W. Mix
  • Patent number: 4579630
    Abstract: A method for the separation of primary amines such as bis-(2-aminoethyl)ether from tertiary amines such as N-(2-methoxyethyl)morpholine which have close boiling points via azeotropic distillation using an entrainer such as monoethanolamine is described. The N-(2-methoxyethyl) morpholine is selectively removed by the monoethanolamine. Surprisingly, a number of structurally similar compounds, such as ethylenediamine, methylethanolamine, water, ethylene glycol and isopropanolamine were discovered to be unsuitable azeotropic distillation agents either because they did not form azeotropes or for other reasons.
    Type: Grant
    Filed: February 7, 1985
    Date of Patent: April 1, 1986
    Assignee: Texaco Inc.
    Inventor: Robert L. Zimmerman
  • 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: 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: 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: 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: 4455198
    Abstract: Ethanol is concentrated from ethanol-water mixtures by extraction or extractive distillation with a solvent which is a cyclic ketone of at least seven carbons or cyclic alcohol of at least eight carbons such a cyclohexylcyclohexanone or cyclohexylcyclohexanol. In the extractive distillation process, a first overheads is produced which can be made to be steam with minimal ethanol content and a second overhead is produced which can be made to be essentially pure ethanol. The preferred solvents are also non-toxic, such that the alcohol can be used for human consumption.
    Type: Grant
    Filed: November 26, 1982
    Date of Patent: June 19, 1984
    Assignee: Allied Corporation
    Inventors: David Zudkevitch, David K. Preston, Stephen E. Belsky
  • 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: 4401514
    Abstract: A method of recovering or extracting chemicals, such as furfural, formic acid, acetic acid and other organic compounds from acidic hydrolysates of plants or vegetable matter, especially spent sulfite liquors after conversion of the pentosans into pentoses and then into furfural by heating the hydrolysate in an acidic environment. The conversion of the pentosans pentoses into furfural, preferably with acidulation, is accomplished in a counterflow or countercurrent flow heat exchanger and a reactor, preferably a tubular reactor. The hydrolysate which has additionally been heated and converted in the reactor is used as a heating medium or heat carrier for heating up the hydrolysate which is converted in the counterflow heat exchanger, whereupon there is recovered as the distillate furfural in conjunction with the formic acid, acetic acid and the like.
    Type: Grant
    Filed: March 18, 1981
    Date of Patent: August 30, 1983
    Assignee: Vereinigte Edelstahlwerke AG (VEW)
    Inventors: Walter Kanzler, Johannes Schedler
  • 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: 4369096
    Abstract: A process has been developed for the purification of expoxides containing carbonyl compounds as impurities wherein the carbonyl compound content is up to 2% by weight of epoxide. Purification is effected by treatment with compounds containing at least one NH.sub.2 group.
    Type: Grant
    Filed: August 18, 1980
    Date of Patent: January 18, 1983
    Assignees: Bayer Aktiengesellschaft, Deutsche Gold und Silberscheideanstalt Vormals Roessler
    Inventors: Hermann Seifert, Helmut Waldmann, Rolf Wirthwein, Willi Hofen
  • Patent number: 4362602
    Abstract: A process for the treatment of heavy products resulting from the manufacture of light hydrocarbons. The heavy products are subjected to steam distillation in the presence of a water-soluble surface-active agent.
    Type: Grant
    Filed: July 14, 1981
    Date of Patent: December 7, 1982
    Assignee: Solvay & Cie.
    Inventors: Roland Hembersin, Remy Nicaise
  • 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