Acetylenic Unsaturation Patents (Class 568/597)
  • Patent number: 9045404
    Abstract: The present invention is directed to a process for the manufacture of 2-pentyn-1-ol starting from 2-propyn-1-ol via the following intermediates (I), (II) wherein R1 is H or linear C1-6 alkyl, R2 is linear C1-6 alkyl or branched C3-6 alkyl and R3 is linear C1-6 alkyl, as well as to the intermediates themselves.
    Type: Grant
    Filed: August 5, 2010
    Date of Patent: June 2, 2015
    Assignee: DSM IP ASSETS B.V.
    Inventors: Werner Bonrath, Francesco Pace, Jocelyn Fischesser, Konrad Witzgall
  • Publication number: 20120197046
    Abstract: The present invention is directed to a process for the manufacture of 2-pentyn-1-ol starting from 2-propyn-1-ol via the following intermediates (I), (II) wherein R1 is H or linear C1-6 alkyl, R2 is linear C1-6 alkyl or branched C3-6 alkyl and R3 is linear C1-6 alkyl, as well as to the intermediates themselves.
    Type: Application
    Filed: August 5, 2010
    Publication date: August 2, 2012
    Inventors: Werner Bonrath, Francesco Pace, Jocelyn Fischesser, Konrad Witzgall
  • Patent number: 7790931
    Abstract: A process for preparing tetrafluorobenzene carbaldehyde alkyl acetal represented by the following formula (II), comprising reducing tetrafluorocyanobenzene represented by the following formula (I) with a metal catalyst containing a platinum group metal in the presence of an alkyl alcohol represented by R—OH (R is an alkyl group of 1 to 4 carbon atoms) and an acid; (I) wherein m is 1 or 2, n is 0 or 1, and m+n is 2, (II) wherein m and n are the same as those in the formula (I), and R is an alkyl group of 1 to 4 carbon atoms.
    Type: Grant
    Filed: June 12, 2006
    Date of Patent: September 7, 2010
    Assignee: Showa Denko K.K.
    Inventors: Haruhiko Ikeda, Hideo Miyata, Katsutoshi Ohno, Katsuro Urakawa
  • Publication number: 20020121223
    Abstract: A copolymer of a strait chain &agr;-olefin and a vinyl compound (I) represented by the general formula CH2═CH—R, wherein R is a hydrocarbon group, the steric parameter Es of the substituent R is −1.64 or less and the steric parameter B1 of the substituent R is 1.53 or more, an adhesive containing the same as an effective ingredient, and an laminate containing the adhesive.
    Type: Application
    Filed: December 21, 2001
    Publication date: September 5, 2002
    Inventors: Nobuo Oi, Akihiro Kondo, Toshiki Mori
  • Patent number: 6008400
    Abstract: Phosphoramidite oligonucleotide synthesis is facilitated by the use of fluoride-labile 5' silyl protecting groups. RNA synthesis is improved by the use of 2 orthoester protecting groups. Reactions are conducted on a solid phase support and acidic deprotection conditions are avoided, as is the necessity of oxidizing the phosphite linkage between each coupling reaction.
    Type: Grant
    Filed: December 19, 1997
    Date of Patent: December 28, 1999
    Inventors: Stephen Scaringe, Marvin H. Caruthers
  • Patent number: 5739394
    Abstract: The invention relates to novel 3,3-dioxy-4,4,4-trifluorobutyric acid derivatives of the formula (I) ##STR1## in which R.sup.1 and R.sup.2 independently of one another represent C.sub.1 -C.sub.10 -alkyl, or represent cyclohexyl, or represent optionally substituted C.sub.6 -C.sub.10 -aryl or C.sub.7 -C.sub.14 -arylalkyl, orR.sup.1 and R.sup.2 together represent C.sub.2 -C.sub.4 -alkylene which is optionally mono- or disubstituted by methyl, or optionally substituted ortho-arylene,R.sup.3 represents hydrogen or C.sub.1 -C.sub.10 -alkyl, or represents cycloalkyl, or represents optionally substituted C.sub.6 -C.sub.10 -aryl or C.sub.7 -C.sub.
    Type: Grant
    Filed: December 16, 1996
    Date of Patent: April 14, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventor: Norbert Lui
  • Patent number: 5349071
    Abstract: Processes for synthesizing tertiary alkynols by reacting carbonyl-group-containing compounds with alkynes in the presence of a basic catalyst are disclosed. Preferred products are 6,10,14-trimethyl-4-pentadecyn-6-ol compounds having the structure: ##STR1## A preferred, novel compound, 6,10,14-trimethyl-4-pentadecyne-2,6-diol, can be used in the synthesis of Vitamin E or Vitamin K.sub.1.
    Type: Grant
    Filed: November 25, 1992
    Date of Patent: September 20, 1994
    Assignee: Loyola University of Chicago
    Inventor: James H. Babler
  • Patent number: 5245085
    Abstract: Acyclic terpene compounds useful as intermediates for producing sarcophytol A which have an anti-carcinogenic promoter activity and anti-tumor activity, which compounds are shown by the general formula (I): ##STR1##
    Type: Grant
    Filed: October 15, 1992
    Date of Patent: September 14, 1993
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Hisao Takayanagi, Yasunori Kitano, Yasuhiro Morinaka
  • Patent number: 4965376
    Abstract: 3,9-Dihydroxynonyne and its derivatives protected at the 9-OH function, of the general formula I ##STR1## where R is hydrogen or a conventional alcohol protective group, and processes for the preparation of the compounds I.
    Type: Grant
    Filed: April 18, 1989
    Date of Patent: October 23, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Huellmann, Rainer Becker, Gerald Lauterbach, Ernst Buschmann, Heinz Eckhardt, Walter Himmele, Christiane Brueckner
  • Patent number: 4877891
    Abstract: 1,1-dialkoxy- or 1,1-(.alpha.,.omega.-methylenedioxy)-non-2-yn-9-ol and their OH-protected derivatives of the general formula I ##STR1## where R.sup.1 and R.sup.2 are each C.sub.1 -C.sub.6 -alkyl or together form an alkylene chain of 2 to 5 carbon atoms and X is hydrogen or a protective group which can be eliminated, their preparation and their use as intermediates.
    Type: Grant
    Filed: August 5, 1988
    Date of Patent: October 31, 1989
    Assignee: BASF Aktiengesellschaft
    Inventors: Rainer Becker, Walter Seufert, Ernst Buschmann, Christiane Bruchner
  • Patent number: 4827004
    Abstract: Novel Isoprene Derivatives which have mucosa-protective and gastric acid secretion-inhibiting properties and are useful for combatting ulcers both by treating and as a prophylaxis against gastric and/or duodenal ulcers.
    Type: Grant
    Filed: August 24, 1987
    Date of Patent: May 2, 1989
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Albert Fischli, Max Schmid, Rudolf Schmid
  • Patent number: 4506069
    Abstract: A prepolymer for use in preparing a binder for low vulnerability gun propellants. The condensation of an alkynediol and formaldehyde produces a prepolymer which is cured with a polyisocyanate. The resulting binder can be combined with 1,3,5,7-tetramethylenetetranitramine (HMX) or 1,3,5-trimethylenetrinitramine (RDX), and is readily extruded as multi-perforated propellant grains, the extruded material having a greatly reduced tendency to slumping, and an enhanced mass impetus value.
    Type: Grant
    Filed: December 21, 1983
    Date of Patent: March 19, 1985
    Assignee: Thiokol Corporation
    Inventors: Michael W. Barnes, Clifford E. Kristofferson, Anthony P. Manzara
  • Patent number: 4317905
    Abstract: A process is disclosed for preparing aliphatic compounds containing two conjugated double bonds cis-cis or cis-trans, characterized in that a compound of the general formula ##STR1## (in which R is H, alkyl from C.sub.1 to C.sub.10, or OY in which Y is a protective group selected from the class consisting of tetrahydropyranyl and 1-ethoxyethyl; X is an ester function selected from the class consisting of the acetates) is reacted with an alkyl-magnesium halide of the general formula:Z--Mg--R.sup.1 (II)(in which Z is chlorine, bromine or iodine, and R.sup.1 is a C.sub.1 -C.sub.10 alkyl group, or a group (CH.sub.2).sub.n OY in which Y has the same meaning as in formula (I), and n is a number from 3 to 10) in the presence of Li.sub.2 CuCl.sub.4, CuCl, CuBr, or CuI at temperatures ranging from about -30.degree. to +10.degree. C. in the presence of ethyl ether or tetrahydrofuran as solvent, to obtain an aliphatic compound of the general formula:R--CH.sub.2 --C.tbd.C--CH.dbd.CH--CH.sub.2 R.sup.
    Type: Grant
    Filed: May 21, 1979
    Date of Patent: March 2, 1982
    Assignee: Montedison S.p.A.
    Inventors: Pietro Massardo, Giorgio Cassani, Paolo Piccardi
  • Patent number: 4311645
    Abstract: A chemical synthesis of an SRS-A active compound from the reaction product of 1-halo-2-octyne and the ether of 2-penten-4-yn-1-ol including intermediates in the synthesis, some of which being antagonists of SRS-A useful for treating allergic reactions.
    Type: Grant
    Filed: March 24, 1980
    Date of Patent: January 19, 1982
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Michael Rosenberger
  • Patent number: 4235824
    Abstract: The invention relates to a method for the preparation of both known and novel fragrances and flavors, and in particular to the preparation and use of the novel fragrance compound, 2,6-nonadiene nitrile, and to a novel method for the preparation of 4-heptynal as the starting product for the preparation of the 2,6-nonadiene nitrile fragrance compound.
    Type: Grant
    Filed: November 9, 1978
    Date of Patent: November 25, 1980
    Assignee: Naarden International N.V.
    Inventors: Petrus C. Traas, Harmannus Boelens, Hans J. Wille
  • Patent number: 4180682
    Abstract: A synthesis of 2,6,10-trimethyl-undecan-1-ol, an intermediate for producing vitamin E, from methacrolein, crotonaldehyde, .beta.-hydroxy-isobutyric acid including intermediates in this synthesis.
    Type: Grant
    Filed: May 12, 1978
    Date of Patent: December 25, 1979
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Noal Cohen, Gabriel Saucy
  • Patent number: 4179579
    Abstract: Novel substituted propargyl alcohols of the formula: ##STR1## novel allylic alcohols of the formula: ##STR2## .delta.,.epsilon.-unsaturated ketones of the formula: ##STR3## are provided. In the above formulas, R represents a group of the formula: ##STR4## wherein X.sub.1 and X.sub.2 are both hydrogen atoms or wherein one of X.sub.1 and X.sub.2 is a hydrogen atom, the other jointly with Z represents a bond; Z jointly with X.sub.1 or X.sub.2 represents a bond or separately represent a hydrogen atom, a hydroxyl group or a lower alkoxy group; R.sub.1 and R.sub.2 are the same or different and represents hydrogen atoms or lower alkyl groups; n is 1 or 2; and when n is 2, X.sub.1, X.sub.2, X, R.sub.1 and R.sub.2 may be the same or different. These novel compounds are easily produced and are useful as perfumes and as interrelated intermediates for the production of terpenoid compounds.
    Type: Grant
    Filed: July 25, 1977
    Date of Patent: December 18, 1979
    Assignee: Kuraray Co., Ltd.
    Inventors: Yoshiji Fujita, Fumio Wada, Takashi Ohnishi, Takashi Nishida, Yoshiaki Omura, Fumio Mori, Takeo Hosogai, Sukeji Aihara