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 the extractive agent is a mono carboxylic acid mixed with certain high boiling organic compounds. Examples of effective agents are: hexanoic acid and butyl benzoate; octanoic acid and nitrobenzene; heptanoic acid, benzyl benzoate and pelargonic acid.
Type:
Grant
Filed:
January 17, 1989
Date of Patent:
April 9, 1991
Assignee:
Lloyd Berg
Inventors:
Lloyd Berg, Kraig M. Wendt, Rudolph J. Szabados
Abstract: 4-Methyl-2-pentanone cannot be easily separated from formic acid by distillation because of the closeness of their boiling points. 4-Methyl-2-pentanone can be readily removed from formic acid by extractive distillation using dimethylamides. Typical effective agents are dimethylformamide; dimethylacetamide and acetyl salicyclic acid; dimethylacetamide, heptanoic acid and methyl benzoate.
Abstract: The lower lactate esters are difficult to separate one from another by conventional distillation or rectification because of the close proximity of their boiling points. Lactate esters can be readily separated from each other by extractive distillation. Typical examples of effective agents are: for methyl lactate from ethyl lactate, ethylene glycol; ethyl lactate from isopropyl lactate, diethylene glycol; isopropyl lactate from n-propyl lactate, isophorone; n-propyl lactate from butyl lactate, 2-hydroxyacetophenone.
Abstract: 2-Methyl butanol-1 cannot be completely removed from 2-methyl butanol-1-pentanol-1 mixtures by distillation because of the proximity of their boiling points. 2-methyl butanol-1 can be readily removed from mixtures of these alcohols by using extractive distillation in which the extractive agent is a mixture of aromatic carboxylic acids or aromatic carboxylic esters. Typical examples of effective agents are: benzoic acid, ethyl salicylate and salicylic acid; methyl benzoate, methyl p-hydroxy benzoate and phenyl salicylate.
Abstract: Ethyl benzene cannot be easily removed from styrene by distillation because of the closeness of their boiling points. Ethyl benzene can be readily separated from styrene by means of extractive distillation using certain nitrogenous organic compounds. Typical effective agents are adiponitrile, methyl glutaronitrile and nitrobenzene.
Abstract: 3-Methyl-2-butanone cannot be separated from formic acid by distillation because of the presence of the maximum boiling azotrope. 3-Methol-2-butanoe can be readily removed from formic acid by extractive distillation using sulfolane. Typical effective agents are: sulfolane and ethylene glycol diacetate; sulfolane, m-toluic acid and anisole.
Abstract: 4-Methyl-2-pentanone cannot be easily separated from formic acid or acetic acid by distillation because of the closeness of their boiling points. 4-Methyl-2-pentanone can be readily removed from formic acid or acetic acid by extractive distillation. Typical effective agents are sulfolane; sulfolane and heptanoic acid; sulfolane, azelaic acid and ethylene glycol diacetate.
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 dimethylformamide, dimethylacetamide or these with certain high boiling organic compounds.
Abstract: A complex mixture of polyols cannot be easily separated by atmospheric or reduced pressure distillation because of the closeness of their boiling points. A mixture of polyols can be readily separated by azeotropic distillation. Typical effective agents are: p-xylene for propylene glycol from 2,3-butanediol and 1,2-butanediol; diisobutyl ketone for ethylene glycol from 1,2-butanediol and 1,3-butanediol; dipentene for glycerine from triethylene glycol and 1,2,4-butanetriol; propylene glycol isobutyl ether for 2,3-butanediol from propylene glycol.
Abstract: n-Propanol and t-amyl alcohol cannot be separated from each other by distillation because of the proximity of their boiling points. n-Propanol can be readily separated from t-amyl alcohol 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: methyl salicylate; benzyl benzoate and hexahydrophthalic anhydride; methyl salicylate, benzoic acid and hexahydrophthalic anhydride.
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 the extractive agent is a benzoic acid derivative mixed with certain higher boiling organic compounds. Examples of effective agents are: o-toluic acid and heptanoic acid; 2-benzoylbenzoic acid and methyl salicylate; p-hydroxybenzoic acid, pelargonic acid and 2-hydroxyacetophenone.
Type:
Grant
Filed:
May 30, 1989
Date of Patent:
June 19, 1990
Assignee:
Lloyd Berg
Inventors:
Lloyd Berg, Kraig M. Wendt, Rudolph J. Szabados
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. Typical effective agents are formic acid, formamide and formic acid-formamide mixture.
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 extractive distillation. Typical extractive distillation agents are acetyl salicylic acid and butyl benzoate; acetyl salicylic acid and ethylene carbonate.
Abstract: Meta and para-diisopropyl benzenes cannot be easily separated from each other by distillation because of the closeness of their vapor pressures. m-Diisopropyl benzene can be readily removed from p-diisopropyl benzene by extractive distillation using certain high boiling organic compounds. Effective extractive agents are diphenyl ether, dimethyl adipate, diisononyl adipate, tributyl phosphate and ethylene glycol phenyl ether.
Abstract: Primary and secondary hydroperoxide contaminants in a tertiary hydroperoxide composition obtained by oxidation of a branched hydrocarbon are removed by contacting the tertiary hydroperoxide with a carboxylic acid derivative such as an anhydride and a basic compound such as sodium hydroxide. A tertiary hydroperoxide such as tertiary butyl hydroperoxide is purified with minimal loss of the desired tertiary hydroperoxide.
Abstract: Meta and para-diisopropylbenzenes cannot be easily separated from each other by distsillation because of the closeness of their vapor pressures. m-Diisopropylbenzene can be readily removed from p-diisopropylbenzene by azeotropic distillation using certain esters. Typical effective azeotropic distillation agents are methyl benzoate and diethylene glycol ethyl ether acetate.
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
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
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.
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 a ketone, either alone or mixed with certain high boiling organic compounds. Examples of effective agents are cyclohexanone; diisobutyl ketone and octanoic acid; isophorone, hexanoic acid and butyl ether.
Type:
Grant
Filed:
May 2, 1988
Date of Patent:
August 22, 1989
Assignee:
Lloyd Berg
Inventors:
Lloyd Berg, Rudolph J. Szabados, Thomas H. Flower
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.
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.
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.
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.
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.
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.
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.
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 the extractive agent is ethylene carbonate or propylene carbonate, either alone or mixed with certain high boiling organic compounds. Examples of effective agents are ethylene carbonate and heptanoic acid; propylene carbonate, benzoic acid and isophorone; propylene carbonate, heptanoic acid and 2-hydroxyacetophenone.
Abstract: A process is described for the production of substantially pure gamma-butyrolactone from a feed mixture containing a major amount of gamma-butyrolactone and a minor amount of diethyl succinate which comprises fractionally distilling the mixture in a fractionation zone in the presence of added diethyl maleate and recovering from the fractionation zone an overhead vaporous product comprising gamma-butyrolactone which is substantially free from diethyl succinate and a liquid bottom product comprising diethyl maleate and diethyl succinate in admixture one with another. This procedure can be used to separate a gamma-butyrolactone rich fraction obtained by distillation in one or more stages of a crude reaction product obtained by hydrogenation of a C.sub.
Abstract: 2-Butanol cannot be completely removed from 2-butanol - t-amyl alcohol mixtures by distillation because of the proximitry of their boiling points. 2-Butanol can be readily removed from mixtures containing it and t-amyl alcohol by using extractive distillation in which the extractive agent is a higher boiling benzoate. Typical examples are methyl benzoate; methyl benzoate and salicylic acid; methyl benzoate, cinnamic acid and hexahydrophthalic anhydride.
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.
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.
Abstract: Ethanol and t-butanol cannot be separated from each other by distillation because of the proximity of their boiling points. Ethanol can be readily separated from t-butanol by using extractive distillation in which the extractive agent is a higher boiling oxygenated organic compound or a mixture of two or more of these. Typical examples of effective agents are: methyl benzoate; benzyl benzoate and benzoic acid; methyl salicylate, hexahydrophthalic anhydride and salicylic acid.
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.
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.
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.
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.
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.
Abstract: n-Propanol and 2-butanol cannot be separated from each other by distillation because of the proximity of their boiling points. n-Propanol can be readily separated from 2-butanol using extractive distillation in which the extractive agent is a higher boiling oxygenated organic compound or a mixture of two or more of these. Typical examples of effective agents are: methyl benzoate; benzoic acid and methyl benzoate; cinnamic acid, phthalic anhydride and methyl benzoate.
Abstract: Isopropanol and t-butanol cannot be separated from each other by distillation because of the proximity of their boiling points. Isopropanol can be readily separated from t-butanol by using extractive distillation in which the extractive agent is a higher boiling oxygenated organic compound or a mixture of two or more of these. Typical examples of effective agents are: methyl benzoate; methyl benzoate and hexahydrophthalic anhydride; phthalic anhydride, hexahydrophthalic anhydride and methyl benzoate.
Abstract: Ethanol and isopropanol cannot be separated from each other by distillation because of the proximity of their boiling points. Ethanol can be readily separated from isopropanol by using extractive distillation in which the extractive agent is a higher boiling oxygenated organic compound or a mixture of two or more of these. Typical examples of effective agents are: methyl salicylate; salicylic acid and hexahydrophthalic anhydride; salicylic acid, hexahydrophthalic anhydride and methyl benzoate.
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.
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.
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.
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.
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.
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.
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 dimethylformamide; dimethylformamide and 1,4-butanediol; dimethylformamide, adiponitrile and dihexyl phthalate.
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.
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.