With Chemical Reaction Patents (Class 203/28)
  • Patent number: 4312714
    Abstract: The oxidation of liquid n-butane with oxygen gas at a temperature of from 120.degree. C. up to 235.degree. C. in the presence of an acetic acid solution containing bromide ion in combination with ions of cobalt or cobalt and manganese produces a reaction effluent containing mainly acetic acid (65 to 72 weight percent) and water (23 to 27 weight percent) together with impurity concentrations of esters and ketones boiling lower than acetic acid, higher carbon (C.sub.3 and C.sub.4) aliphatic monocarboxylic acids boiling higher than acetic acid and the difficultly separable 3-bromo-2-butanone impurity. The concentration of said bromoketone can be decreased by maintaining said reaction effluent or its debutanized residue at a temperature of from 150.degree. C. up to 200.degree. C. for 15 to 150 minutes. Subsequent distillation even further decreases the concentration of the bromoketone in the acetic acid distillate fraction.
    Type: Grant
    Filed: December 17, 1979
    Date of Patent: January 26, 1982
    Assignee: Standard Oil Company (Indiana)
    Inventor: Jon J. Harper
  • Patent number: 4282389
    Abstract: A process for the simultaneous manufacture of pure methyl tertiary butyl ether (MTBE) and a substantially isotubene-free mixture of C.sub.4 -hydrocarbons, by reacting the isobutene contained in the mixture of C.sub.4 -hydrocarbons with excess methanol in the liquid phase at elevated temperatures on strongly acid, macroporous, organic ion exchange resins.The process has the following steps:(a) methanol and isobutene are reacted in a molar ratio of 2:1 to 5:1 at temperatures between 30.degree. and 100.degree. C.;(b) the unconverted hydrocarbons are then removed as the top product under a pressure of 2 to 10 bars from a first rectification column;(c) the bottom product from this first column is rectified in a second column under normal pressure or under a slight excess pressure of up to 2 bars at the top of the column, the bottom product of this rectification is recycled to reaction zone (a), if necessary, after separating off a portion of the tertiary butanol formed and the C.sub.
    Type: Grant
    Filed: December 4, 1979
    Date of Patent: August 4, 1981
    Assignee: Chemische Werke Huls A.G.
    Inventors: Wilhelm Droste, Fritz Obenaus
  • Patent number: 4278503
    Abstract: Excessive energy consumption of a combination of multi-fractionations and multi-distillations of concentrating aqueous acetic acid product of liquid phase oxidations, especially oxidation of liquid n-butane with oxygen gas while the butane is dissolved in liquid acetic acid containing a catalyst system comprising Co-Br or Co-Mn-Br, is avoided and an otherwise hard to remove bromo-ketone is readily removed by a combination of sequential steps of decompressing the oxidation reaction mixture to remove unreacted butane as well as gaseous products, heat treating the decompressed liquid at a temperature of from 150.degree. C. up to 200.degree. C. for from 15 up to 150 minutes, subjecting the heat treated liquid to fractionation while recycling to the rectification zone thereof an aqueous portion of low boiling impurities as a means for concentrating the acetic acid and thereafter further concentrating the acetic acid produced by continuous fractional crystallization.
    Type: Grant
    Filed: December 26, 1979
    Date of Patent: July 14, 1981
    Assignee: Standard Oil Company (Indiana)
    Inventors: Martin A. Zeitlin, Jon J. Harper
  • Patent number: 4273622
    Abstract: Residual products obtained in the catalytic dehydration of alpha-methylbenzyl alcohol are treated to recover monomeric styrene values by a process which comprises fractionally distilling the residual products in two stages under different temperature and time conditions.
    Type: Grant
    Filed: November 26, 1979
    Date of Patent: June 16, 1981
    Assignee: Halcon Research & Development Corp.
    Inventor: Mitchell Becker
  • Patent number: 4268362
    Abstract: A method for purifying raw acetic acid containing formaldehyde is provided wherein raw acetic acid is heat-treated at a temperature of about its boiling point or higher, in advance of the conventional distillation for removing a lower boiling fraction, and the acetic acid thus heat-treated is distilled to remove the lower boiling fraction, whereby the content of formaldehyde can be reduced down to 30 ppm or lower.
    Type: Grant
    Filed: December 28, 1976
    Date of Patent: May 19, 1981
    Assignee: Chisso Corporation
    Inventors: Tetsuya Ogawa, Norio Yoshizaki, Tadakatsu Katsuragi, Makoto Nakamura, Kiyonori Shiiba
  • Patent number: 4262140
    Abstract: A process for the production of anhydrous or substantially anhydrous formic acid by hydrolysis of methyl formate which is carried out in a column having an upper fractionating section, a middle hydrolysis section and a lower extraction section and in which(a) the hydrolysis is carried out in the middle section of the columm, with water and methyl formate in countercurrent,(b) the resulting formic acid is extracted, in the lower section of the column, by means of a carboxylic acid amide which is fed into the lower end of the middle section of the column,(c) the extract phase, consisting in the main of formic acid and the carboxylic acid amide, is distillatively dehydrated, or substantially dehydrated, in the lower section of the column,(d) the methanol and uncovered methyl formate are removed by fractional distillation in the upper section of the column and(e) the pure formic acid or concentrated aqueous formic acid is distilled from the anhydrous or substantially anhydrous extract phase in a second column, le
    Type: Grant
    Filed: December 3, 1979
    Date of Patent: April 14, 1981
    Assignee: BASF Aktiengesellschaft
    Inventors: Kaspar Bott, Gerd Kaibel, Herwig Hoffmann, Otto Kratzer, Rudolf Irnich
  • Patent number: 4254246
    Abstract: A new process for use with continuously operated plants for the production of polyester polymers suitable for producing fibers, bottles and film, by reacting ethylene glycol and terephthalic acid in the presence of a catalyst so that the vapour by-products from the esterification, prepolycondensation and polycondensation stages are continuously rectified in two in-line columns yielding ethylene glycol of high purity (99.85%) which is returned to the process, waste water with 400 ppm ethylene glycol, and a heavy fraction containing oligomers, diethylene glycol, etc.Moreover, an improvement in the quality of the esterified product is attained as it contains less than 0.6% diethylene glycol without the use of diisopropylamine, a poisonous additive.
    Type: Grant
    Filed: March 26, 1979
    Date of Patent: March 3, 1981
    Assignee: Davy International AG
    Inventors: Ovidiu Dicoi, Hans Wewer
  • Patent number: 4232177
    Abstract: A method for conducting chemical reactions and fractionation of the reaction mixture comprising feeding reactants to a distillation column reactor into a feed zone and concurrently contracting the reactants with a fixed bed catalytic packing to concurrently carry out the reaction and fractionate the reaction mixture.For example, a method for preparing methyl tertiary butyl ether in high purity from a mixed feed stream of isobutene and normal butene comprising feeding the mixed feed stream to a distillation column reactor into a feed zone at the lower end of a distillation reaction zone, and methanol into the upper end of said distillation reaction zone, which is packed with a properly supported cationic ion exchange resin, contacting the C.sub.4 feed and methanol with the catalytic distillation packing to react methanol and isobutene, and concurrently fractionating the ether from the column below the catalytic zone and removing normal butene overhead above the catalytic zone.
    Type: Grant
    Filed: February 21, 1979
    Date of Patent: November 4, 1980
    Assignee: Chemical Research & Licensing Company
    Inventor: Lawrence A. Smith, Jr.
  • Patent number: 4213847
    Abstract: Heavy petroliferous stocks such as vacuum and atmospheric resids, tar sand oils, shale oils, liquids from conversion of coal and the like are concurrently distilled and hydroprocessed for removal of sulfur, nitrogen and metals and are hydrocracked or otherwise hydroprocessed in a packed distillation column under hydrogen pressure wherein the packing is constituted, at least to a substantial extent in both stripping and rectifying sections by catalyst suited to the desired conversions. In a specific application to catalytic hydrodewaxing of lubricating oil stocks, improvement of Viscosity Index (VI) of dewaxed product results.
    Type: Grant
    Filed: May 16, 1979
    Date of Patent: July 22, 1980
    Assignee: Mobil Oil Corporation
    Inventors: Nai Y. Chen, Ikai Wang
  • Patent number: 4194964
    Abstract: Heavy petroliferous stocks such as vacuum and atmospheric resids, tar sand oils, shale oils, liquids from conversion of coal and the like are concurrently distilled and hydroprocessed for removal of sulfur, nitrogen and metals and are hydrocracked or otherwise hydroprocessed in a packed distillation column under hydrogen pressure wherein the packing is constituted, at least to a substantial extent in both stripping and rectifying sections by catalyst suited to the desired conversions.
    Type: Grant
    Filed: July 10, 1978
    Date of Patent: March 25, 1980
    Assignee: Mobil Oil Corporation
    Inventors: Nai Y. Chen, Ikai Wang
  • Patent number: 4195032
    Abstract: The present invention relates to an improved process for the continuous production of alkylmonoisocyanates from commercial solutions containing N-alkyl carbamic acid chlorides by thermally decomposing the N-alkyl carbamic acid chlorides in the presence of inert solvents, and recovering the pure monoisocyanates by distillation.
    Type: Grant
    Filed: February 9, 1979
    Date of Patent: March 25, 1980
    Assignee: Bayer Aktiengesellschaft
    Inventors: Johannes Koster, Peter Heitkamper, Peter Fuhrmann, Helmut Porkert
  • Patent number: 4187376
    Abstract: Unreacted urea and/or biuret contaminants in a cyanuric acid-inert solvent reaction product are removed by distilling the solvent therefrom at a temperature of from about 150.degree. C. to about 250.degree. C. and at a pressure of from about 70 to about 170 mm. of Hg. A distillate of said solvent containing the urea, biuret and a cyanuric acid reaction product is collected.
    Type: Grant
    Filed: September 22, 1977
    Date of Patent: February 5, 1980
    Assignee: FMC Corporation
    Inventor: Ronald H. Carlson
  • Patent number: 4162270
    Abstract: In a process for producing 4,4'-dihydroxydiphenylsulfone by reacting phenol with sulfuric acid in the presence of a solvent, an improvement which comprises using at least a member selected from the group consisting of chlorobenzene, dichlorobenzene, trichlorobenzene, chlorotoluene, diethylbenzene, xylene, decalin, tetralin and tetrachloroethane as the solvent and removing said solvent progressively and finally substantially completely from the mixture while maintaining the reaction mixture at a temperature of about 160.degree. to about 200.degree. C. to effect precipitation of 4,4'-dihydroxydiphenylsulfone and isomerization of 2,4'-dihydroxydiphenylsulfone to 4,4'-dihydroxydiphenylsulfone.
    Type: Grant
    Filed: April 14, 1978
    Date of Patent: July 24, 1979
    Assignee: Konishi Chemical Industry Co., Ltd.
    Inventors: Eiji Ogata, Koji Ono, Shoji Nakagaki
  • Patent number: 4159925
    Abstract: Process for isolating propylene glycol diacarboxylates in the preparation of propylene oxide by reaction of propylene with a solution of percarboxylic acid in an organic solvent, the boiling point of which is lower than that of the carboxylic acid which corresponds to the percarboxylic acid used as the epoxidizing agent, and higher than that of propylene oxide, separation, by distillation, of the reaction mixture which essentially contains propylene oxide, the carboxylic acid corresponding to the percarboxylic acid used as the epoxidizing agent and one or more of the by-products propyleneglycol, propylene glycol monocarboxylate and propylene glycol dicarboxylate as well as propylene and the organic solvent, into a fraction containing propylene oxide and propylene and a fraction containing the carboxylic acid, the by-products mentioned and the organic solvent and further separation of the fractions into the individual components by distillation.
    Type: Grant
    Filed: December 9, 1977
    Date of Patent: July 3, 1979
    Assignees: Bayer Aktiengesellschaft, Deutsche Gold- und Silber-Scheideanstalt vormals Roessler
    Inventors: Gerd Schreyer, Rolf Wirthwein, Karl-Hermann Reissinger, Jorg Krekel
  • Patent number: 4158611
    Abstract: Crude phenol is recovered from CHP reaction products by continuously feeding to a main column separating in its uppermost section phenol from crude acetone, this fraction being removed overhead, and in the lower section crude phenol from higher boilers, including acetophenone and carbinol, the crude phenol being removed as a sidestream fraction from the main column at a point in the column above the feed-point wherein the total concentration of acetophenone plus carbinol is less than 1,000 ppm and the higher boiling compounds being removed as a base fraction.
    Type: Grant
    Filed: December 15, 1977
    Date of Patent: June 19, 1979
    Assignee: BP Chemicals Limited
    Inventor: Maurice D. Cooke
  • Patent number: 4115530
    Abstract: Process for the production of gaseous hydrogen chloride by extraction of dilute aqueous hydrochloric acid with amines.(a) The aqueous hydrochloric acid is extracted with an amine or with a mixture of an amine and an inert organic solvent which is immiscible with water and has a lower boiling point than the amine employed, the amines utilized being tertiary alkyl amines, tertiary aryl dialkyl amines, secondary arylalkyl amines, primary alkylaryl amines, or mixtures thereof, which contain 14-32 carbon atoms in the nitrogen-bound side chains, and among these at most one nitrogen-bound methyl group and at least one aliphatic residue containing at least 6 carbon atoms, and wherein the acid constant K.sub.a of the amine is smaller than 10.sup.-3.(b) An inert, water-immiscible organic solvent which has a lower boiling point than the amine employed is added to the extract, unless the solvent has already been added in stage (a).
    Type: Grant
    Filed: July 14, 1977
    Date of Patent: September 19, 1978
    Assignee: Chemische Werke Huls AG
    Inventors: Alfred Coenen, Kurt Kosswig, Gunter Prominski
  • Patent number: 4082617
    Abstract: Recovery of the chemical components of a cellulosic organic solvent regenerating solution containing a dialkylacylamide, a lower aliphatic monohydric alcohol, a nitrite of the alcohol and nitric acid. The process comprises distilling the solution to remove the alcohol nitrite and alcohol, leaving the dialkylacylamide and nitric acid, recovering the alcohol, hydrolyzing to convert the alcohol nitrite to the alcohol and nitrous acid, neutralizing the nitric and nitrous acid with an alkali or alkaline earth metal oxide or hydroxide and distilling the solution to remove water and to separate and recover the remaining alcohol, the dialkylacylamide and the nitrate and nitrite salts. The nitrite and nitrate salts are converted by pyrolysis to nitrogen dioxide. The process results in substantially total recovery of the process chemicals.
    Type: Grant
    Filed: August 18, 1976
    Date of Patent: April 4, 1978
    Assignee: International Telephone and Telegraph Corporation
    Inventors: Norman A. Portnoy, David Paul Anderson
  • Patent number: 4073660
    Abstract: Recovery of the chemical components of a cellulosic organic solvent regenerating solution containing a dialkylacylamide, water, nitrous and nitric acid. The process comprises neutralizing the solution to form the metal salts of nitrous and nitric acid, distilling the neutralized solution to remove and recover the water and dialkylacylamide solvent and pyrolyzing the metal salts in the presence of oxygen to remove and recover nitrogen dioxide gas. The process results in substantially total recovery of the process chemicals.
    Type: Grant
    Filed: August 18, 1976
    Date of Patent: February 14, 1978
    Assignee: International Telephone and Telegraph Corporation
    Inventors: Norman A. Portnoy, David P. Anderson
  • Patent number: 4067779
    Abstract: Crude 1,10-decanedicarboxylic acid produced by the nitric acid oxidation at 20.degree.14 60.degree. C. of cyclododecanone, cyclododecanol or a mixture thereof can be purified by distillation to a purity suitable for use in the production of polyamides and polyesters by reducing prior to distillation, e.g., by heating to 70.degree.-90.degree. C., the organically bound nitrogen content and as required the nitric acid content, e.g., by washing, and water content thereof so that the sample which is distilled has maximum contents thereof of 0.05%, 0.02% and 0.1% by weight, respectively, and distilling the pre-purified sample at a sump temperature of 215.degree.-225.degree. C. and at a pressure of 0.5 - 2 torr.
    Type: Grant
    Filed: April 29, 1975
    Date of Patent: January 10, 1978
    Assignee: Chemische Werke Huls Aktiengesellschaft
    Inventors: Ferdinand List, Otto Rauhut, Peter Hegenberg, Rudolf Strobele
  • Patent number: 4039599
    Abstract: A process for the production of paraxylene by the catalytic isomerization of xylenes wherein the reaction zone effluent is fractionated in three columns in series with the overhead product of the second column in the series being sent to a paraxylene separation zone, C.sub.9 hydrocarbons being rejected as the bottoms product of the third column, and the overhead product of the third column being combined with the raffinate stream of the paraxylene separation zone and recycled to the isomerization zone.
    Type: Grant
    Filed: August 26, 1976
    Date of Patent: August 2, 1977
    Assignee: UOP Inc.
    Inventor: Steve A. Gewartowski
  • Patent number: 4010240
    Abstract: Contaminated sulfuric acid which may contain water, organic compounds and inorganic salts is converted to almost pure concentrated sulfuric acid by passing the acid through a Pauling plant and distilling the concentrated contaminated acid.Addition of nitric acid improves the decomposition of organic compounds and ammonium salts of the contaminated acid.
    Type: Grant
    Filed: June 12, 1974
    Date of Patent: March 1, 1977
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Helmold von Plessen, Eberhard Fischer, Siegfried Schiessler
  • Patent number: 3972987
    Abstract: Two-step-process for regenerating dilute sulfuric acid which may contain organic and inorganic impurities such as heavy metal salts. In the first step the impure acid is distilled in vacuo and in the second step concentrated in a Pauling apparatus.
    Type: Grant
    Filed: December 4, 1974
    Date of Patent: August 3, 1976
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Helmold von Plessen, Siegfried Schiessler