Patents by Inventor Karl Clauss

Karl Clauss has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).

  • Patent number: 5103046
    Abstract: 6-Methyl-3,4-dihydro-1,2,3-oxathiazin-4-one 2,2-dioxide is prepared bya) reacting, an inert organic solvent, a salt of sulfamic acid, which is at least partially soluble therein, with at least approximately the equimolar amount of an acetoacetylating agent, in the presence of an amine or phosphine catalyst, and by cyclizing the acetoacetamide-N-sulfonate which is formed in this reaction, or the free sulfonic acid,b) by the action of at least approximately the equimolar amount of SO.sub.3, where appropriate in an inert inorganic or organic solvent, to give 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-one 2,2-dioxide, which is produced in the form of the acid in this reaction;it is possible, if desired, to obtain from the acid formc) the appropriate salts by neutralization with bases.The non-toxic salts-- in particular the potassium salt-- are valuable synthetic sweeteners.
    Type: Grant
    Filed: January 29, 1991
    Date of Patent: April 7, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Karl Clauss, Adolf Linkies, Dieter Reuschling
  • Patent number: 5011982
    Abstract: 6-Methyl-3,4-dihydro-1,2,3-oxathiazin-4-one 2,2-dioxide is prepared bya) reacting, in an inert organic solvent, a salt of sulfamic acid, which is at least partially soluble therein, with at least approximately the equimolar amount of an acetoacetylating agent, in the presence of an amine or phosphine catalyst, and by cyclizing the acetoacetamide-N-sulfonate which is formed in this reaction, or the free sulfonic acid,b) by the action of at least approximately the equimolar amount of SO.sub.3, where appropriate in an inert inorganic or organic solvent, to give 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-one 2,2-dioxide, which is produced in the form of the acid in this reaction;it is possible, if desired, to obtain from the acid formc) the appropriate salts by neutralization with bases. The non-toxic salts--in particular the potassium salt--are valuable synthetic sweeteners.
    Type: Grant
    Filed: April 16, 1990
    Date of Patent: April 30, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Karl Clauss, Adolf Linkies, Dieter Reuschling
  • Patent number: 4695629
    Abstract: 6-Methyl-3,4-dihydro-1,2,3-oxathiazin-4-one 2,2-dioxide is prepared by(a) reacting, in an inert organic solvent, a salt of sulfamic acid, which is at least partially soluble therein, with at least approximately the equimolar amount of an acetoacetylating agent, in the presence of an amine or phosphine catalyst, and by cyclizing the acetoacetamide-N-sulfonate which is formed in this reaction, or the free sulfonic acid,(b) by the action of at least approximately the equimolar amount of SO.sub.3, where appropriate in an inert inorganic or organic solvent, to give 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-one 2,2-dioxide, which is produced in the form of the acid in this reaction;it is possible, if desired, to obtain from the acid form(c) the appropriate salts by neutralization with bases. The non-toxic salts - in particular the potassium salt - are valuable synthetic sweeteners.
    Type: Grant
    Filed: June 3, 1986
    Date of Patent: September 22, 1987
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Karl Clauss, Adolf Linkies, Dieter Reuschling
  • Patent number: 4638063
    Abstract: 6-Methyl-3,4-dihydro-1,2,3-oxathiazin-4-one 2,2-dioxide is prepared by reaction of acetoacetamide with at least approximately twice the molar amount of SO.sub.3 per mole of acetoacetamide, if appropriate in an inert inorganic or organic solvent. Relevant salts can be obtained, using bases, from the product which results in the form of the acid.The non-toxic salts, in particular the potassium salt, are valuable synthetic sweeteners.
    Type: Grant
    Filed: November 19, 1985
    Date of Patent: January 20, 1987
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Karl Clauss, Adolf Linkies, Dieter Reuschling
  • Patent number: 4625024
    Abstract: 6-Methyl-3,4-dihydro-1,2,3-oxathiazin-4-one 2,2-dioxide and its non-toxic salts are prepared by reacting acetoacetamide with an S-O compound of the formula IFSO.sub.2 Y (I)wherein Y.dbd.F, Cl, --OSO.sub.2 F or --OSO.sub.2 Cl, preferably only F,in the presence of bases.The non-toxic salts--especially the potassium salt--are valuable synthetic sweeteners.
    Type: Grant
    Filed: August 5, 1985
    Date of Patent: November 25, 1986
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Erwin Schmidt, Karl Clauss
  • Patent number: 4607100
    Abstract: 6-Methyl-3,4-dihydro-1,2,3-oxathiazin-4-one 2,2-dioxide is prepared by(a) reacting, in an inert organic solvent, a salt of sulfamic acid, which is at least partially soluble therein, with at least approximately the equimolar amount of an acetoacetylating agent, in the presence of an amine or phosphine catalyst, and by cyclizing the acetoacetamide-N-sulfonate which is formed in this reaction, or the free sulfonic acid,(b) by the action of at least approximately the equimolar amount of SO.sub.3, where appropriate in an inert inorganic or organic solvent, to give 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-one 2,2-dioxide, which is produced in the form of the acid in this reaction;it is possible, if desired, to obtain from the acid form(c) the appropriate salts by neutralization with bases.The non-toxic salts--in particular the potassium salt--are valuable synthetic sweeteners.
    Type: Grant
    Filed: March 20, 1985
    Date of Patent: August 19, 1986
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Karl Clauss, Adolf Linkies, Dieter Reuschling
  • Patent number: 4563521
    Abstract: 6-Methyl-3,4-dihydro-1,2,3-oxathiazin-4-one 2,2-dioxide is prepared by reaction of acetoacetamide with at least approximately twice the molar amount of SO.sub.3 per mole of acetoacetamide, if appropriate in an inert inorganic or organic solvent. Relevant salts can be obtained, using bases, from the product which results in the form of the acid.The non-toxic salts, in particular the potassium salt, are valuable synthetic sweeteners.
    Type: Grant
    Filed: March 20, 1985
    Date of Patent: January 7, 1986
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Karl Clauss, Adolf Linkies, Dieter Reuschling
  • Patent number: 4052453
    Abstract: Process for preparing acetoacetamide-N-sulfofluoride by reacting amidosulfofluoride at a temperature of from 50.degree. to 100.degree. C with diketene, optionally in the presence of inert solvents or diluents.
    Type: Grant
    Filed: October 1, 1975
    Date of Patent: October 4, 1977
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hartmut Pietsch, Karl Clauss, Harald Jensen, Erwin Schmidt
  • Patent number: 4009161
    Abstract: 3-Sulfohalides of 6-methyl-2H-1,3-oxazin-2,4(3H)-dione of the formula I ##STR1## in which X represents fluorine or chlorine are prepared by reacting fluorosulfonyl isocyanate or chlorosulfonyl isocyanate, at a temperature of from -35.degree. to +70.degree. C, optionally in the presence of an inert solvent, with diketene, acetoacetyl fluoride, acetoacetyl chloride, acetoacetic acid or an isopropenyl ester of the formula CH.sub.2 =C(OOCR)-CH.sub.3 in which R represents an alkyl radical having from 1 to 4 carbon atoms, a substituted or unsubstituted phenyl or benzyl radical.
    Type: Grant
    Filed: July 16, 1975
    Date of Patent: February 22, 1977
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hartmut Pietsch, Karl Clauss, Erwin Schmidt, Harald Jensen
  • Patent number: 3993689
    Abstract: Compounds of the formula ##SPC1##In which R represents an alkyl radical having from 1 to 4 carbon atoms and Hal stands for fluorine or chlorine are prepared by reacting at a temperature of from -40.degree. to +20.degree. C an i-propenylalkanoic acid ester of the formula ##EQU1## with an isocyanate of the formulaO=C=N--SO.sub.2 Hal (V)in which R and Hal have the same meaning as above, and isolating the compound of formula III.
    Type: Grant
    Filed: July 16, 1975
    Date of Patent: November 23, 1976
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Erwin Schmidt, Karl Clauss, Hartmut Pietsch, Harald Jensen
  • Patent number: 3969347
    Abstract: The potassium salt practically free of fluoride of 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-one-2,2-dioxide is prepared by cyclization of acetoacetamide-N-sulfofluoride with at least two moles potassium hydroxide, potassium methylate or a mixture of potassium hydroxide and potassium methylate per mole of sulfofluoride in methanol as solvent containing less than 50 % by weight of water at a temperature of from -20.degree. to +60.degree.C and separating the crystalline potassium salt of the oxathiazinone dioxide from the reaction solution. The compound obtained has a pure sweet taste.
    Type: Grant
    Filed: July 16, 1975
    Date of Patent: July 13, 1976
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Erwin Schmidt, Karl Clauss, Hartmut Pietsch, Harald Jensen
  • Patent number: 3969348
    Abstract: 6-Methyl-3,4-dihydro-1,2,3-oxathiazin-4-one-2,2-dioxide or the nontoxic salts thereof is prepared by reacting 6-methyl-2,3-dihydro-1,3-oxazin-2,4-dione-3-sulfo-fluoride of the formula ##EQU1## with at least 1 mole water per mole of fluoride to obtain acetoacetamide-N-sulfo-fluoride with splitting off of CO.sub.2, treating the acetoacetamide-N-sulfofluoride with an aqueous and/or alcoholic base and isolating the oxathiazinone or the salts thereof.
    Type: Grant
    Filed: July 16, 1975
    Date of Patent: July 13, 1976
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hartmut Pietsch, Karl Clauss, Erwin Schmidt, Harald Jensen
  • Patent number: 3968106
    Abstract: 6-Methyl-3,4-dihydro-1,2,3-oxathiazin-4-one-2,2-dioxide and the nontoxic salts thereof are prepared by reacting acetone and fluorosulfonyl isocyanate in a molar proportion of from 14:1 to 150:1 at a temperature of from 0.degree. to 60.degree.C, distilling off the excess acetone from the reaction mixture with acetoacetamide-N-sulfofluoride and bringing about cyclization by a treatment with bases at a pH of from 5 to 12. The oxathiazinone derivatives are used as sweeteners.
    Type: Grant
    Filed: July 16, 1975
    Date of Patent: July 6, 1976
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Karl Clauss, Hartmut Pietsch, Erwin Schmidt, Harald Jensen
  • Patent number: 3968107
    Abstract: 6-Methyl-3,4-dihydro-1,2,3-oxathiazin-4-one-2,2-dioxide and the nontoxic salts thereof are prepared by reacting acetoacetic acid with fluorosulfonyl isocyanate at a temperature of from -20.degree.C to +50.degree.C in the presence of from 0.5 to 2 moles, calculated on the FSI used, of an alkali methal fluoride or a tertiary amine of the formulaN(R.sub.1)(R.sub.2)(R.sub.3)in which R.sub.1, R.sub.2, R.sub.3 represent identical or different alkyl radicals having from 1 to 10 carbon atoms, two of the radicals R.sub.1 to R.sub.3 optionally form together an alkylene radical having from 4 to 5 carbon atoms which may contain N, O, or S as hetero atom, or one of the radicals R.sub.1 to R.sub.3 represents a phenyl radical, or of pyridine or quinoline, or of a mixture of the aforesaid compounds, and transforming the salt of acetoacetamide-N-sulfofluoride obtained into the oxathiazinone salt or the free oxathiazinone by a treatment with aqueous and/or alcoholic bases.
    Type: Grant
    Filed: July 16, 1975
    Date of Patent: July 6, 1976
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Karl Clauss, Erwin Schmidt, Hartmut Pietsch, Harald Jensen
  • Patent number: D729171
    Type: Grant
    Filed: April 4, 2013
    Date of Patent: May 12, 2015
    Assignee: Phoenix Contact GmbH & Co. KG
    Inventor: Karl Clauss Dietel
  • Patent number: D731980
    Type: Grant
    Filed: September 19, 2013
    Date of Patent: June 16, 2015
    Assignee: PHOENIX CONTACT GMBH & CO. KG
    Inventor: Karl Clauss Dietel
  • Patent number: D747541
    Type: Grant
    Filed: September 18, 2013
    Date of Patent: January 12, 2016
    Assignee: PHOENIX CONTACT GMBH & CO. KG
    Inventor: Karl Clauss Dietel
  • Patent number: D770675
    Type: Grant
    Filed: July 22, 2015
    Date of Patent: November 1, 2016
    Assignee: PHOENIX CONTACT GMBH & CO. KG
    Inventor: Karl Clauss Dietel
  • Patent number: D771306
    Type: Grant
    Filed: July 23, 2015
    Date of Patent: November 8, 2016
    Assignee: PHOENIX CONTACT GMBH & CO. KG
    Inventor: Karl Clauss Dietel