Aldehyde Or Ketone Patents (Class 203/62)
  • Patent number: 5776321
    Abstract: 1-Propanol cannot be separated from t-amyl alcohol by distillation or rectification because of the closeness of their boiling points. 1-Propanol is readily separated from t-amyl alcohol by azeotropic distillation. Effective agents are heptane, ethyl acetate and tetrahydrofuran.
    Type: Grant
    Filed: May 30, 1997
    Date of Patent: July 7, 1998
    Inventor: Lloyd Berg
  • Patent number: 5772853
    Abstract: 1-Propanol and t-amyl alcohol cannot be separated by distillation or rectification because of the closeness of their boiling points. 1-Propanol is readily separated from t-amyl alcohol by extractive distillation. Effective agents are dipentene, amyl acetate and 1,4-dioxane.
    Type: Grant
    Filed: November 17, 1997
    Date of Patent: June 30, 1998
    Inventor: Lloyd Berg
  • Patent number: 5763695
    Abstract: 3-Methyl-1-butanol cannot be separated from 1-pentanol by distillation or rectification because of the closeness of their boiling points. 3-Methyl-1-butanol is readily separated from 1-pentanol by extractive distillation. Effective agents are butyl benzoate, 2-undecanone and diethylene glycol methyl ether.
    Type: Grant
    Filed: July 14, 1997
    Date of Patent: June 9, 1998
    Inventor: Lloyd Berg
  • Patent number: 5763694
    Abstract: 3-Methyl-1-butanol cannot be separated from 1-pentanol by distillation or rectification because of the closeness of their boiling points. 3-Methyl-1-butanol is readily separated from 1-pentanol by azeotropic distillation. Effective agents are methylcyclohexane, methyl formate and tetrahydrofuran.
    Type: Grant
    Filed: July 14, 1997
    Date of Patent: June 9, 1998
    Inventor: Lloyd Berg
  • Patent number: 5759359
    Abstract: 2-Butanol cannot be separated from t-amyl alcohol by distillation or rectification because of the closeness of their boiling points. 2-Butanol is readily separated from t-amyl alcohol by azeotropic distillation. Effective agents are methyl acetate, ethyl propionate and octane.
    Type: Grant
    Filed: September 8, 1997
    Date of Patent: June 2, 1998
    Inventor: Lloyd Berg
  • Patent number: 5741940
    Abstract: Disclosed is a very economical way to produce vinyl carbonyls such as ethyl vinyl ketone. Disclosed also is a purification process of separating vinyl carbonyls and coreactants. The catalyst and reaction conditions give useful yields of vinyl carbonyls, the thermodynamically unfavorable product along with coreactants that are more thermodynamically favored. Disclosed also is the separation of reactants that takes place at low distillation temperatures and pressures in the presence of antioxidant.
    Type: Grant
    Filed: June 28, 1996
    Date of Patent: April 21, 1998
    Assignee: Eastman Chemical Company
    Inventor: William A. Beavers
  • Patent number: 5738763
    Abstract: 2-Methyl-1-propanol is difficult to separate from 2-methyl-1-butanol by conventional distillation or rectification because of the proximity of their boiling points. 2-Methyl-1-propanol can be readily separated from 2-methyl-1-butanol by extractive distillation. Effective agents are hexyl formate, 2-heptanone and dipropyl amine.
    Type: Grant
    Filed: July 8, 1996
    Date of Patent: April 14, 1998
    Inventor: Lloyd Berg
  • Patent number: 5738764
    Abstract: T-Amyl alcohol is difficult to separate from 2-methyl-1-propanol by conventional distillation or rectification because of the proximity of their boiling points. T-Amyl alcohol can be easily separated from 2-methyl-1-propanol by azeotropic distillation. Effective agents are triethyl amine, ethyl ether and acetone.
    Type: Grant
    Filed: April 8, 1997
    Date of Patent: April 14, 1998
    Inventor: Lloyd Berg
  • Patent number: 5723024
    Abstract: 2-Methyl-1-propanol is difficult to separate from 1-butanol by conventional distillation or rectification because of the proximity of their boiling points. 2-Methyl-1-propanol can be readily separated from 1-butanol by extractive distillation. Effective agents are ethyl benzene, amyl acetate and propoxypropanol.
    Type: Grant
    Filed: August 26, 1996
    Date of Patent: March 3, 1998
    Inventor: Lloyd Berg
  • Patent number: 5720857
    Abstract: 1,2,4-Trimethylbenzene is difficult to sepparate from 1,2,3-trimethylbenzene because of the proximity of their boiling points. They are readily separated by azeotropic distillation. Effective agents are 1-propanol, methyl formate and 1-nitropropane.
    Type: Grant
    Filed: January 2, 1997
    Date of Patent: February 24, 1998
    Inventor: Lloyd Berg
  • Patent number: 5718809
    Abstract: T-Amyl alcohol and 2-methyl-1-propanol are difficult to separate by conventional distillation or rectification because of the proximity of their boiling points. T-Amyl alcohol can be easily separated from 2-methyl-1-propanol by extractive distillation. Effective agents are N,N-dimethylacetamide, cyclohexyl amine and glycerol.
    Type: Grant
    Filed: April 8, 1997
    Date of Patent: February 17, 1998
    Inventor: Lloyd Berg
  • Patent number: 5716499
    Abstract: 2-Methyl-1-propanol is difficult to separate from 1-butanol by conventional distillation or rectification because of the proximity of their boiling points. 2-Methyl-1-propanol can be easily separated from 1-butanol by azeotropic distillation. Effective agents are isobutyl acetate, methyl cyclohexane and 2-nitropropane.
    Type: Grant
    Filed: August 12, 1996
    Date of Patent: February 10, 1998
    Inventor: Lloyd Berg
  • Patent number: 5709781
    Abstract: 1-Butanol is difficult to separate from 2-pentanol by conventional distillation or rectification because of the proximity of their boiling points. 1-Butanol can be easily separated from 2-pentanol by extractive distillation. Effective agents are anisole, ethyl nonanate and butyl ether.
    Type: Grant
    Filed: February 11, 1997
    Date of Patent: January 20, 1998
    Inventor: Lloyd Berg
  • Patent number: 5705038
    Abstract: Phellandrene is difficult to separate from limonene by conventional distillation or rectification because of the proximity of their boiling points. Phellandreneecan be readily separated from limonene by extractive distillation. Effective agents are o-cresol, tripropylene glycol and isophorone.
    Type: Grant
    Filed: November 25, 1996
    Date of Patent: January 6, 1998
    Inventor: Lloyd Berg
  • Patent number: 5698080
    Abstract: Phellandrene is difficult to separate from limonene because of the proximity of their boiling points. They are readily separated by azeotropic distillation. Effective agents are ethanol, dioxolane and acetonitrile.
    Type: Grant
    Filed: November 22, 1996
    Date of Patent: December 16, 1997
    Inventor: Lloyd Berg
  • Patent number: 5693193
    Abstract: Propylene oxide is recovered through the use of an additive in a distillation solution, resulting in suppressed side reactions and reduced loss of product. Propylene oxide is produced by oxidizing ethylbenzene in a liquid phase with molecular oxygen to a obtain a reaction liquid containing ethylbenzene hydroperoxide; distilling the reaction liquid to obtain a concentrated solution of ethylbenzene hydroperoxide; further mixing and reacting the concentrated solution with propylene to obtain a mixed solution containing propylene oxide; and distilling the mixed solution to separate and recover propylene oxide. At least one compound selected from aliphatic saturated alcohols having 2 to 4 carbon atoms, allyl alcohol, saturated aliphatic hydrocarbons having 6 or 7 carbon atoms, benzene, ethers, ketones, nitriles, amines, pyridines, diamines, and aminoalcohols is added to the mixed distillation solution in an amount of 0.01-100 parts by weight per 100 parts by weight of propylene oxide.
    Type: Grant
    Filed: March 23, 1995
    Date of Patent: December 2, 1997
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Takashi DeGuchi, Kazuo Kimura, Naoto Meki, Masaru Ishino, Tetsuya Suzuta
  • Patent number: 5693194
    Abstract: Butyraldehyde cannot be separated from ethanol by conventional distillation or rectification because they form a minimum boiling azeotrope. Butyraldehyde can be readily separated from ethanol by extractive distillation. Effective agents are 2-propanol, m-xylene and dimethylsulfoxide.
    Type: Grant
    Filed: November 25, 1996
    Date of Patent: December 2, 1997
    Inventor: Lloyd Berg
  • Patent number: 5658435
    Abstract: 2-Methyl-1-propanol is difficult to separate from 2-butanol by conventional distillation or rectification because of the proximity of their boiling points. 2-Methyl-1-propanol can be easily separated from 2-butanol by azeotropic distillation. Effective agents are sulfolane, acetonitrile and acetal.
    Type: Grant
    Filed: September 17, 1996
    Date of Patent: August 19, 1997
    Inventor: Lloyd Berg
  • Patent number: 5645695
    Abstract: 2-Methyl-1-propanol is difficult to separate from 2-methyl-1-butanol by conventional distillation or rectification because of the proximity of their boiling points. 2-Methyl-1-propanol can be readily separated from 2-methyl-1-butanol by azeotropic distillation. Effective agents are tetrahydrofuran, methyl acetate and toluene.
    Type: Grant
    Filed: July 8, 1996
    Date of Patent: July 8, 1997
    Inventor: Lloyd Berg
  • Patent number: 5582693
    Abstract: 3-Carene and limonene cannot be separated from each other by rectification because of the closeness of their boiling points. They are readily separated by azeotropic distillation. Effective agents are: cyclopentanol, 2-nitropropane, ethyl formate amyl acetate dimethyl carbonate, tetrahydrofuran, acetic acid and 2-amino-amethyl-1-propanol.
    Type: Grant
    Filed: January 11, 1996
    Date of Patent: December 10, 1996
    Assignee: Lloyd Berg
    Inventor: Lloyd Berg
  • Patent number: 5470443
    Abstract: Isopropanol is difficult to separate from 2-butanone by conventional distillation or rectification because of the proximity of their boiling points. Isopropanol can be readily separated from 2-butanone by extractive distillation. Effective agents are o-cresol, ethylene glycol and nitroethane.
    Type: Grant
    Filed: January 10, 1995
    Date of Patent: November 28, 1995
    Assignee: Lloyd Berg
    Inventor: Lloyd Berg
  • Patent number: 5466345
    Abstract: o-Xylene cannot be separated from p-xylene and m-xylene by conventional distillation or rectification because of the proximity of their boiling points. o-Xylene can be readily separated from mixtures of p-xylene and m-xylene by azeotropic distillation. Effective agents are 3-methyl-1-butanol, methyl propionate and 3-pentanone.
    Type: Grant
    Filed: May 31, 1995
    Date of Patent: November 14, 1995
    Assignee: Lloyd Berg
    Inventor: Lloyd Berg
  • Patent number: 5460700
    Abstract: 1-Hexene is difficult to separate from hexane by conventional distillation or rectification because of the proximity of their boiling points. 1-Hexene can be readily separated from hexane by extractive distillation. Effective agents are hexyl acetate, methyl amyl alcohol and acetophenone.
    Type: Grant
    Filed: May 19, 1994
    Date of Patent: October 24, 1995
    Assignee: Lloyd Berg
    Inventor: Lloyd Berg
  • Patent number: 5458741
    Abstract: Benzene is difficult to separate from cyclohexane or cyclohexene by conventional distillation or rectification because of the close proximity of their boiling points. Benzene can be readily separated from cyclohexane or cyclohexene by using extractive distillation. Effective agents are: for benzene from cyclohexane, methyl acetoacetate; for benzene from cyclohexene, ethyl acetoacetate.
    Type: Grant
    Filed: January 14, 1994
    Date of Patent: October 17, 1995
    Assignee: Lloyd Berg
    Inventor: Lloyd Berg
  • Patent number: 5456806
    Abstract: A procedure for the recovery of phenol from its mixtures containing cumene and alpha-methylstyrene, is based on the extractive distillation of the mixtures with acetophenone.
    Type: Grant
    Filed: April 25, 1994
    Date of Patent: October 10, 1995
    Assignee: Enichem S.p.A.
    Inventors: Loreno Lorenzoni, Giuseppe Messina, Slavatore Simula
  • Patent number: 5453166
    Abstract: Ethanol is impossible to separate from 2-butanone by conventional distillation or rectification because of the minimum boiling azeotrope between these two. Ethanol can be readily separated from 2-butanone by extractive distillation. Effective agents are dipromyl amine, phenol and dimethylsulfoxide.
    Type: Grant
    Filed: November 7, 1994
    Date of Patent: September 26, 1995
    Assignee: Lloyd Berg
    Inventor: Lloyd Berg
  • Patent number: 5447608
    Abstract: 3-Methyl-2-butanol, 2-pentanol and 1-butanol are difficult to separate by conventional distillation or rectification because of the proximity of their boiling points. Mixtures of these three can be readily separated from each other by azeotropic distillation. Effective agents are hexyl acetate, hexane and 3-methyl pentane.
    Type: Grant
    Filed: August 1, 1994
    Date of Patent: September 5, 1995
    Assignee: Lloyd Berg
    Inventor: Lloyd Berg
  • Patent number: 5445716
    Abstract: Ethanol is difficult to separate from isopropanol by conventional distillation or rectification because of the proximity of their boiling points. Ethanol can be readily separated from isopropanol by extractive distillation. Effective agents are dipentene, anisole and ethyl benzene.
    Type: Grant
    Filed: October 18, 1994
    Date of Patent: August 29, 1995
    Assignee: Lloyd Berg
    Inventor: Lloyd Berg
  • Patent number: 5443697
    Abstract: Heptane is difficult to separate from 1-heptene by conventional distillation or rectification because of the proximity of their boiling points. Heptane can be readily separated from 1-heptene by extractive distillation. Effective agents are diacetone alcohol, ethyl butyrate and dimethylsulfoxide.
    Type: Grant
    Filed: May 19, 1994
    Date of Patent: August 22, 1995
    Assignee: Lloyd Berg
    Inventor: Lloyd Berg
  • Patent number: 5437770
    Abstract: Ethanol is difficult to separate from isopropanol by conventional distillation or rectification because of the proximity of their boiling points. Ethanol can be readily separated from isopropanol by azeotropic distillation. Effective agents are sec. butyl acetate, hexene-1 and 1,3-dioxolane.
    Type: Grant
    Filed: September 13, 1994
    Date of Patent: August 1, 1995
    Assignee: Lloyd Berg
    Inventor: Lloyd Berg
  • Patent number: 5425855
    Abstract: Ethyl benzene is difficult to separate from p-xylene by conventional distillation or rectification because of the closeness of their boiling points. Ethyl benzene can be readily separated from p-xylene by extractive distillation. An effective agent is 5-methyl-2-hexanone, also called methyl isoamyl ketone.
    Type: Grant
    Filed: April 8, 1994
    Date of Patent: June 20, 1995
    Assignee: Lloyd Berg
    Inventor: Lloyd Berg
  • Patent number: 5425853
    Abstract: Propylene glycol is difficult to separate from ethylene glycol by conventional distillation or rectification because of the proximity of their boiling points. Propylene glycol can be readily separated from ethlene glycol by azeotropic distillation. Effective agens are m-diisopropyl benzene, 1-octene, 3-carene and myrcene.
    Type: Grant
    Filed: June 30, 1994
    Date of Patent: June 20, 1995
    Assignee: Lloyd Berg
    Inventor: Lloyd Berg
  • Patent number: 5425854
    Abstract: Methylene chloride is difficult to separate from tetrahydrofuran by conventional distillation or rectification because of the proximity of their vapor pressures. Methylene chloride can be readily separated from tetrahydrofuran by extractive distillation. Effective agents are 1-pentanol, 1,2-butanediol and 3-nitrotoluene.
    Type: Grant
    Filed: January 17, 1995
    Date of Patent: June 20, 1995
    Assignee: Lloyd Berg
    Inventor: Lloyd Berg
  • Patent number: 5417813
    Abstract: 1-Butanol is difficult to semarate from 2-pentanol by conventional distillation or rectification because of the proximity of their boiling points. 1-Butanol can be readily separated from 2-pentanol by azeotropic distillation. Effective agents are 1-octene, hexane and methyl cyclohexane.
    Type: Grant
    Filed: July 11, 1994
    Date of Patent: May 23, 1995
    Assignee: Lloyd Berg
    Inventor: Lloyd Berg
  • Patent number: 5407540
    Abstract: 3-Methyl-2-butanol is difficult to separate from 1-butanol by conventional distillation or rectification because of the proximity of their boiling points. 3-Methyl-2-butanol can be readily separated from 1-butanol by extractive distillation. Effective agents are ethyl n-valerate, dimethylacetamide and dimethylsulfoxide.
    Type: Grant
    Filed: September 23, 1994
    Date of Patent: April 18, 1995
    Assignee: Lloyd Berg
    Inventor: Lloyd Berg
  • Patent number: 5405504
    Abstract: 1-Decene is impossible to separate from 2-octanone by conventional distillation or rectification because the two compounds form a minimum boiling azeotrope. 1-Decene can be readily separated from 2-octanone by azeotropic distillation. Effective agents are 1-propanol, 2-ethoxyethanol, and methanol.
    Type: Grant
    Filed: January 31, 1994
    Date of Patent: April 11, 1995
    Assignee: Lloyd Berg
    Inventors: Lloyd Berg, Randy W. Wytcherley
  • Patent number: 5405505
    Abstract: Benzene is difficult to separate from cyclohexane or cyclohexene by conventional distillation or rectification because of the close proximity of their boiling points. Benzene can be readily separated from cyclohexane or cyclohexene by using azeotropic distillation. Effective agents are: for benzene from cyclohexane, dimethoxymethane; for benzene from cyclohexene, methanol.
    Type: Grant
    Filed: January 14, 1994
    Date of Patent: April 11, 1995
    Assignee: Lloyd Berg
    Inventor: Lloyd Berg
  • Patent number: 5403448
    Abstract: 1-Decene is difficult to separate from 2-octanone by conventional distillation or rectification because of the proximity of their boiling points. 1-Decene can be readily separated from 2-octanone by azeotropic distillation. Effective agents are butyl propionate and 1-propanol.
    Type: Grant
    Filed: January 14, 1994
    Date of Patent: April 4, 1995
    Assignee: Lloyd Berg
    Inventor: Lloyd Berg
  • Patent number: 5401366
    Abstract: 1-Butanol is difficult to separate from 2-pentanol by conventional distillation or rectification because of the proximity of their boiling points. 1-Butanol can be readily separated from 2-pentanol by extractive distillation. Effective agents are ethyl benzene, d-limonene and terpinolene.
    Type: Grant
    Filed: July 11, 1994
    Date of Patent: March 28, 1995
    Assignee: Lloyd Berg
    Inventor: Lloyd Berg
  • Patent number: 5393385
    Abstract: Hexane is difficult to separate from vinyl acetate and/or methyl acrylate by conventional distillation or rectification because of the closeness of their boiling points. Hexane can be readily separated from vinyl acetate and/or methyl acrylate by extractive distillation. Effective agents are dimethylsulfoxide and dimethylformamide.
    Type: Grant
    Filed: March 14, 1994
    Date of Patent: February 28, 1995
    Assignee: Lloyd Berg
    Inventors: Lloyd Berg, Randi W. Wytcherley
  • Patent number: 5391264
    Abstract: alpha-Phellandrene is difficult to separate from d-limonene by conventional distillation or rectification because of the proximity of their boiling points. alpha-Phellandrene can be readily separated from d-limonene by azeotropic distillation. Effective agents are n-butyl acetate and sulfolane.
    Type: Grant
    Filed: March 14, 1994
    Date of Patent: February 21, 1995
    Assignee: Lloyd Berg
    Inventor: Lloyd Berg
  • Patent number: 5385649
    Abstract: 1-Hexene is difficult to separate from hexane by conventional distillation or rectification because of the proximity of their boiling points. 1-Hexene can be readily separated from hexane by azeotropic distillation. Effective agents are 2-ethyl-1-butanol and diacetone alcohol.
    Type: Grant
    Filed: May 18, 1994
    Date of Patent: January 31, 1995
    Assignee: Lloyd Berg
    Inventor: Lloyd Berg
  • Patent number: 5380405
    Abstract: alpha-Phellandrene is difficult to separate from 3-carene by conventional distillation or rectification because of the proximity of their boiling points. alpha-phellandrene can be readily separated from 3-carene by azeotropic distillation. Effective agents are methyl formate, nitroethane and acetal.
    Type: Grant
    Filed: January 24, 1994
    Date of Patent: January 10, 1995
    Assignee: Lloyd Berg
    Inventor: Lloyd Berg
  • Patent number: 5360520
    Abstract: 2-Butanol is difficult to separate from t-amyl alcohol by conventional distillation or rectification because of the proximity of their boiling points. 2-Butanol can be readily separated from t-amyl alcohol by extractive distillation. Effective agents are methyl caproate, adiponitrile and cyclopentanone.
    Type: Grant
    Filed: January 18, 1994
    Date of Patent: November 1, 1994
    Assignee: Lloyd Berg
    Inventor: Lloyd Berg
  • Patent number: 5358608
    Abstract: 1-Propanol is difficult to separate from 2-butanol by conventional distillation or rectification because of the proximity of their boiling points. 1-Propanol can be readily separated from 2-butanol by extractive distillation. Effective agents are isobutyl acetate, isobornyl methyl acetate and ethyl butyrate.
    Type: Grant
    Filed: January 18, 1994
    Date of Patent: October 25, 1994
    Assignee: Lloyd Berg
    Inventor: Lloyd Berg
  • Patent number: 5348625
    Abstract: Ethanol is difficult to separate from isopropanol by conventional distillation or rectification because of the proximity of their boiling points. Ethanol can be readily separated from isopropanol by extractive distillation. Effective agents are methyl caproate, cyclopentane and isobutyl acetate.
    Type: Grant
    Filed: January 14, 1994
    Date of Patent: September 20, 1994
    Assignee: Lloyd Berg
    Inventor: Lloyd Berg
  • Patent number: 5338410
    Abstract: 2-Butanol is difficult to separate from t-amyl alcohol by conventional distillation or rectification because of the proximity of their boiling points. 2-Butanol can be readily separated from t-amyl alcohol by azeotropic distillation. Effective agents are ethyl acetoacetate, nitroethane and 3-pentanone.
    Type: Grant
    Filed: January 18, 1994
    Date of Patent: August 16, 1994
    Assignee: Lloyd Berg
    Inventor: Lloyd Berg
  • Patent number: 5338411
    Abstract: Ethanol is difficult to separate from isopropanol by conventional distillation or rectification because of the proximity of their boiling points. Ethanol can be readily separated from isopropanol by azeotropic distillation. Effective agents are methyl ethyl ketone, cyclopentane and 2-pyrrolidinone.
    Type: Grant
    Filed: January 14, 1994
    Date of Patent: August 16, 1994
    Assignee: Lloyd Berg
    Inventor: Lloyd Berg
  • Patent number: 5332478
    Abstract: 1-Propanol is difficult to separate from 2-butanol by conventional distillation or rectification because of the proximity of their boiling points. 1-Propanol can be readily separated from 2-butanol by azeotropic distillation. Effective agents are t-butyl methyl ether, 1,4-dioxane and ethyl formate.
    Type: Grant
    Filed: January 14, 1994
    Date of Patent: July 26, 1994
    Assignee: Lloyd Berg
    Inventor: Lloyd Berg
  • Patent number: 5277766
    Abstract: Heptane cannot be removed from heptane-vinyl acetate mixtures by distillation because of the minimum boiling azeotrope. Heptane can be readily removed from vinyl acetate by extractive distillation. Typical effective agents are dimethylsulfoxide, phenol, diisobutyl ketone and hexyl acetate.
    Type: Grant
    Filed: March 30, 1993
    Date of Patent: January 11, 1994
    Assignee: Lloyd Berg
    Inventor: Lloyd Berg