Aldehydes Patents (Class 568/420)
  • Patent number: 4621901
    Abstract: Liquid crystalline mixtures containing compounds of the formula ##STR1## wherein n stands for the number 0 or 1; X.sup.1 and X.sup.2 denote single covalent bonds or one of the symbols X.sup.1 and X.sup.2 also denotes --COO--, --OOC-- or --CH.sub.2 CH.sub.2 --; the rings A.sup.1, A.sup.2, and A.sup.3 represent 1,4-phenylene, 2-fluoro-1,4-phenylene or trans-1,4-cyclohexylene or one of these rings also represents a 2,5-disubstituted pyrimidine ring or a trans-2,5-disubstituted m-dioxane ring; R.sup.1 signifies 4-alkenyl or on a cyclohexyl ring also 2Z-alkenyl; and R.sup.2 denotes alkyl, alkoxy, --CN or --NCS,as well as the manufacture of these compounds and the use for electro-optical purposes are described.
    Type: Grant
    Filed: June 26, 1985
    Date of Patent: November 11, 1986
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Martin Petrzilka, Martin Schadt
  • Patent number: 4605749
    Abstract: There is provided a process for the production of aldehydes wherein an oric halide is reacted with carbon monoxide at a superatmospheric pressure in the presence of a hydrogen donor and in the presence of a base and of a catalyst in a solvent system.Catalysts of choice are transition metal catalysts. A preferred temperature range is from about 50.degree. to 150.degree. C.
    Type: Grant
    Filed: June 20, 1985
    Date of Patent: August 12, 1986
    Assignee: State of Israel, Prime Minister's Office, Atomic Energy Commission
    Inventors: Ouri Buchman, Ilan Pri-Bar
  • Patent number: 4599468
    Abstract: Described are ether carboxaldehydes defined according to the generic structure: ##STR1## wherein X represents aryl, alkaryl, hydroxyalkyl, alkenyl, cycloalkenyl, lower alkyl or bicycloalkyl; wherein Y represents C.sub.1 -C.sub.3 lower alkylene; wherein Z completes an alkyl substituted C.sub.6 cycloalkyl ring or represents no moiety; wherein R represents hydrogen or methyl; wherein m represents 0 or 1; wherein n represents 0 or 1; wherein p represents 0 or 1 and wherein q represents 0 or 1 with the provisos that when m is 1, Z completes the alkyl substituted or unsubstituted C.sub.
    Type: Grant
    Filed: June 14, 1985
    Date of Patent: July 8, 1986
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Futoshi Fujioka, Richard M. Boden, William L. Schreiber
  • Patent number: 4584409
    Abstract: Described are tertiary hydroxyl carboxaldehydes defined according to the generic structure: ##STR1## wherein the lines ##STR2## represent covalent carbon-carbon bonds when m does not=0; and wherein the lines ##STR3## do not represent any bonds when m=0; wherein R represents hydrogen or methyl; wherein p and q each represents 0 or 1 with the proviso that p=1 when q=0 and p=0 when q=1; wherein X and Z each represent one or more carbon atoms required to complete a bicyclo ring with the lines ##STR4## represents carbon-carbon bonds; wherein X and Z complete a phenyl moiety when the line ##STR5## represents no bond; wherein X and Z complete a cycloalkyl ring moiety with the lines ##STR6## represent carbon-carbon bonds and with the line ##STR7## representing no bond; and wherein when m is 0, X represents an alkylene moiety, processes for preparing same by means of reacting carbon monoxide and hydrogen with an unsaturated tertiary alcohol defined according to the structure: ##STR8## by means of an oxo reaction, and
    Type: Grant
    Filed: March 8, 1985
    Date of Patent: April 22, 1986
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Futoshi Fujioka, Richard M. Boden, William L. Schreiber
  • Patent number: 4571438
    Abstract: A process for the preparation of olefinic aldehydes and intermediates is disclosed. The condensation of an .alpha.,.omega.-dihalide with a metal acetylide gives an acetylenic halide which can be reduced to give an olefinic halide, then oxidized to give the desired olefinic aldehyde or the acetylenic halide can be oxidized first to give an acetylenic aldehyde and then reduced to give the desired olefinic aldehyde.
    Type: Grant
    Filed: March 21, 1985
    Date of Patent: February 18, 1986
    Assignee: Phillips Petroleum Company
    Inventors: Jim D. Byers, Dennis S. Banasiak
  • Patent number: 4568478
    Abstract: There is disclosed a solution of at least one fluoroxy compound, wherein said solution has a fluoroxy compound concentration of at least 0.5 meq/liter; said concentration containing about 35 to 100% of an acyl hypofluorite, based on the total number of equivalents of fluoroxy compounds present. The acyl hypofluorite has the formula X(CF.sub.2).sub.n COOF wherein X is H or F and n is 5 to 16. The solution is prepared by treating a suspension of a corresponding specified alkali salt with excess F.sub.2, and is useful as a selective fluorinating agent.
    Type: Grant
    Filed: April 18, 1984
    Date of Patent: February 4, 1986
    Assignee: E. I. Dupont de Nemours and Company
    Inventors: William J. Middleton, Shlomo Rozen
  • Patent number: 4554360
    Abstract: Provided is a process for converting an aromatic compound to prepare an iodoarene, Ar--I, and an aryl compound which is a compound wherein an unsaturated compound is bonded directly to an aryl group, Ar, which process comprises reacting a diaryliodonium salt represented by general formula (I)[Ar--I.sup..sym. --Ar]X.sup..crclbar. (I)wherein Ar is an aryl group which may be substituted and two Ar's are identical and X.sup..crclbar. is a counter ion inert to the reaction with the unsaturated compound in a solvent in the presence of a transition metal catalyst and a base or a reducing metal, said reaction being carried out at a temperature not higher than 80.degree. C. and/or by using at least one of the base, the reducing metal and the unsaturated compound in an amount not more than 1.
    Type: Grant
    Filed: March 29, 1984
    Date of Patent: November 19, 1985
    Assignee: Nippon Petrochemicals Company, Limited
    Inventors: Yasuo Yamazaki, Takehiko Suzuki, Isoo Shimizu, Yasuo Matsumura
  • Patent number: 4550213
    Abstract: An improvement for manufacturing paraformaldehyde prills from an aqueous solution of formaldehyde which comprises polymerizing the formaldehyde in the presence of a catalyst of sodium hydroxide in a concentration of from about 0.5 to about 5 ppm, aging the resulting mixture at about 100.degree. to about 130.degree. C. for about 10 to about 60 minutes, spraying the aged mixture into a prilling tower at from about 100.degree. to about 130.degree. C., collecting the prills in a fluidized bed at the base of the tower at from about 45.degree. to about 60.degree. C., removing the prills to a separate vessel where the prills further polymerize and dry at from about 15.degree. to about 30.degree. C. for about 3 to about 5 hours while operating the vessel in a plugged flow manner, and collecting the resulting prills.
    Type: Grant
    Filed: June 29, 1984
    Date of Patent: October 29, 1985
    Assignee: Celanese Corporation
    Inventors: Hubert H. Thigpen, Richard J. Clos
  • Patent number: 4543429
    Abstract: 1(7)-p-Methen-9-al, a novel terpene aldehyde, possesses useful organoleptic properties and develops bitter, herbal and aromatic perfume notes. In the field of flavors, 1(7)-p-menthen-9-al develops flowery, herbal and fatty characters reminiscent of certain aspects of the flavor of nuts or cumin.
    Type: Grant
    Filed: February 28, 1983
    Date of Patent: September 24, 1985
    Assignee: Firmenich SA
    Inventors: Anthony F. Morris, Francois Delay, Fritz Gautschi, Alan F. Thomas, Wolfgang K. Giersch, Andre Boschung
  • Patent number: 4540826
    Abstract: A process for the preparation of olefinic aldehydes and intermediates is disclosed. The condensation of an .alpha.,.omega.-dihalide with a metal acetylide gives an acetylenic halide which can be reduced to give an olefinic halide, then oxidized to give the desired olefinic aldehyde or the acetylenic halide can be oxidized first to give an acetylenic aldehyde and then reduced to give the desired olefinic aldehyde.
    Type: Grant
    Filed: August 12, 1983
    Date of Patent: September 10, 1985
    Assignee: Phillips Petroleum Company
    Inventors: Dennis S. Banasiak, Jim D. Byers
  • Patent number: 4532364
    Abstract: Described are ether carboxaldehydes defined according to the generic structure: ##STR1## wherein X represents aryl, alkaryl, hydroxyalkyl, alkenyl, cycloalkenyl, lower alkyl or bicycloalkyl; wherein Y represents C.sub.1 -C.sub.3 lower alkylene; wherein Z completes an alkyl substituted C.sub.6 cycloalkyl ring or represents no moiety; wherein R represents hydrogen or methyl; wherein m represents 0 or 1; wherein n represents 0 or 1; wherein p represents 0 or 1 and wherein q represents 0 or 1 with the provisos that when m is 1, Z completes the alkyl substituted or unsubstituted C.sub.
    Type: Grant
    Filed: September 19, 1983
    Date of Patent: July 30, 1985
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Futoshi Fujioka, Richard M. Boden, William L. Schreiber
  • Patent number: 4521630
    Abstract: Aldehydes are prepared by hydrogenating a compound of general formula R'COOR, wherein R represents a hydrogen atom, an alkyl or an acyl group, or a metal, and R' represents an optionally substituted hydrocarbyl group having at most two alpha-hydrogen atoms, provided it has at most one beta-hydrogen atom, in case it has two alpha-hydrogen atoms, in the presence of a catalyst comprising at least one metal selected from rare earth metals and iron on an alumina-based carrier.
    Type: Grant
    Filed: August 9, 1983
    Date of Patent: June 4, 1985
    Assignee: Shell Oil Company
    Inventors: Freddy Wattimena, Hendricus J. Heijmen
  • Patent number: 4518797
    Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is an acyl group or certain optionally halo-substituted hydrocarbyl groups, and X is --CH.sub.2 CH(OCH.sub.3).sub.2, --CH.sub.2 CHO, --CH.dbd.CHOR.sup.2 in which R.sup.2 is acyl, --CHO,--C(O)Cl, --C(O)Br or --C(O)OR in which R is H, a salt-forming cation, an alkyl group or the residue of a pyrethroid alcohol are new pesticides or intermediates therefore. The compounds are prepared using a multi-step synthesis starting from the natural terpene, 3-carene.
    Type: Grant
    Filed: March 15, 1979
    Date of Patent: May 21, 1985
    Assignee: Shell Oil Company
    Inventor: Steven A. Roman
  • Patent number: 4504671
    Abstract: Aldoxime or ketoxime-O-alkanoic acid is prepared by transoximation of an aldehyde or ketone, the reaction being conducted in a liquid phase at a pressure below one atmosphere. Conversion of the aldoxime or ketoxime-O-alkanoic acid to the ester or salt form is also described.
    Type: Grant
    Filed: October 15, 1982
    Date of Patent: March 12, 1985
    Assignee: PPG Industries, Inc.
    Inventors: Dennis K. Krass, John C. Crano, Melvin S. Newman
  • Patent number: 4503260
    Abstract: Hemi-formals are reacted with hydrogen and carbon monoxide in the presence of certain rhodium catalysts to form glycol aldehyde.
    Type: Grant
    Filed: June 13, 1983
    Date of Patent: March 5, 1985
    Assignee: Monsanto Company
    Inventors: Steven R. Auvil, Patrick L. Mills
  • Patent number: 4486218
    Abstract: 1-Vinyltriazole compounds of the formula ##STR1## wherein R.sup.1 is alkyl, substituted alkyl, cycloalkyl, aryl or substituted aryl;R.sup.2 is alkyl;R.sup.3 is alkyl, cycloalkyl, cycloalkenyl, substituted cycloalkenyl, alkenyl, aryl or substituted aryl; orR.sup.2 and R.sup.3, together with the carbon to which they are bonded, represent cycloalkenyl, substituted cycloalkenyl, cycloalkyl or substituted cycloalkyl;X is the group ##STR2## or, alternatively, X may represent a keto group provided that when X is a keto group, R.sup.1 is alkyl, substituted alkyl, cycloalkyl, or substituted cycloalkyl;R.sup.4 is hydrogen, alkyl, aralkyl, substituted aralkyl, acyl, carbamoyl or substituted carbamoyl;R.sup.5 is hydrogen, alkyl, aralkyl or substituted aralkyl;and acid addition salts and metal salt complexes thereof; are outstandingly effective plant growth regulants and as fungicides.
    Type: Grant
    Filed: August 20, 1981
    Date of Patent: December 4, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wolf Reiser, Wilfried Draber, Karl H. Buchel, Klaus Lurssen, Paul-Ernst Frohberger, Volker Paul
  • Patent number: 4474992
    Abstract: Described is 2-isopropenyl-1,5-dimethyl-cyclopentane carboxaldehyde of our invention having the structure: ##STR1## and uses thereof for augmenting or enhancing the aroma of perfumes, colognes and perfumed articles including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, perfumed polymers, fabric softener compositions, fabric softener articles including drier-added fabric softener articles, hair preparations, cosmetic powders, face creams, moisturizers and the like.
    Type: Grant
    Filed: March 10, 1983
    Date of Patent: October 2, 1984
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Michael Licciardello, Richard M. Boden
  • Patent number: 4472577
    Abstract: A process for the production of an .alpha.-hydroxy-phosphonic acid ester of the general formula ##STR1## in which R represents an optionally substituted aryl or heteroaryl group, andR.sup.1 and R.sup.2 independently of each other represent an alkyl or phenyl group, or together represent an alkanediyl (alkylene) radical,comprising reacting .alpha.-oxo-phosphonic acid esters with hydrogen in the presence of a hydrogenation catalyst. The .alpha.-hydroxy-phosphonic acid esters of formula (I) are intermediate products for the production of pesticides.
    Type: Grant
    Filed: July 15, 1982
    Date of Patent: September 18, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventor: Reinhard Lantzsch
  • Patent number: 4471118
    Abstract: A process for the preparation of an aldehyde of the formulaR--CHO (I)in which R is an optionally substituted alkyl, alkenyl, alkinyl, cycloakyl, cycloalkenyl, aralkyl, aralkenyl, aryl or heteroaryl radical, comprising heating an .alpha.-hydroxyphosphonic acid ester of the formula ##STR1## the aldehyde of the formula (I) can be used as an intermediate in the production of pest-combating agents.
    Type: Grant
    Filed: July 15, 1982
    Date of Patent: September 11, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventor: Reinhard Lantzsch
  • Patent number: 4432906
    Abstract: Methyl derivatives of arachidonic acid and intermediates thereto have been synthesized. These derivatives are inhibitors of SRS-A synthesis and are useful for treating and preventing allergic reactions.
    Type: Grant
    Filed: September 14, 1981
    Date of Patent: February 21, 1984
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Noal Cohen, Giuseppe Weber
  • Patent number: 4338466
    Abstract: Prostaglandin analogs and process for the preparation thereof as precursors or the synthesis of oligomeric mixtures exhibiting biological activity for protection of oxidative phosphorylation of degraded mitochondria. The analogs have the general formula: ##STR1## synthesized by O-alkylating a 2-alkylcyclopentane-1,3-dione to form an enol ether, reacting the ether with CH.sub.2 .dbd.CHMgBr to form a vinyl, oxidizing the vinyl with OsO.sub.4 and NaIO.sub.4 to form an aldehyde, and reacting the aldehyde with a sodium salt of dimethyl (2-oxoalkyl)phosphonate.
    Type: Grant
    Filed: April 2, 1981
    Date of Patent: July 6, 1982
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventor: George L. Nelson
  • Patent number: 4328373
    Abstract: An improved vapor phase process for producing aldehydes from corresponding carboxylic acids and esters of said carboxylic acids by contacting the acid or ester at temperatures from about 300.degree. C. to about 500.degree. C. with hydrogen, in the presence of a catalyst selected from certain metal oxides.
    Type: Grant
    Filed: March 17, 1980
    Date of Patent: May 4, 1982
    Assignee: The Dow Chemical Company
    Inventor: Edwin J. Strojny
  • Patent number: 4314072
    Abstract: 2-(2-Hydroxy-3-oxobutyl)-3,3-dimethylcyclopropanecarbaldehyde and certain derivatives thereof are useful intermediates for the preparation of dihalovinyl-type pyrethroid esters.
    Type: Grant
    Filed: November 23, 1979
    Date of Patent: February 2, 1982
    Assignee: Shell Oil Company
    Inventor: Johannes L. M. Syrier
  • Patent number: 4301081
    Abstract: The invention includes novel alkali metal complex compounds (and processes for their preparation) which are useful, inter alia for the hydrogenation of alkali metals at room temperature or below room temperature to form hydrides or nitrides.
    Type: Grant
    Filed: January 28, 1980
    Date of Patent: November 17, 1981
    Assignee: Studiengesellschaft Kohle mbH
    Inventor: Borislav Bogdanovic
  • Patent number: 4298757
    Abstract: 2-(2,2-Dihalovinyl-3,3-dimethylcyclopropyl)vinyl alkanoates in which the alkanoate moiety contains from two to six carbon atoms are new chemical compounds useful as intermediates in the preparation of certain pyrethroid acids. The alkanoates are prepared by reacting 2-(2,2-dihalovinyl-3,3-dimethylcyclopropyl)ethanal with the appropriate alkanoic acid anhydride.
    Type: Grant
    Filed: July 9, 1979
    Date of Patent: November 3, 1981
    Assignee: Shell Oil Company
    Inventors: Johannes Van Berkel, Hendrik C. Kelderman
  • Patent number: 4281203
    Abstract: New compounds of formula: ##STR1## wherein R.sup.1 is an alkyl group and R.sup.2 a 2-oxopropyl group or a 2,2-dihalovinyl group are prepared by elimination of an alcohol R.sup.1 OH from an acetal of formula: ##STR2## The compounds are intermediates in route to pyrethroid insecticides.
    Type: Grant
    Filed: May 28, 1980
    Date of Patent: July 28, 1981
    Assignee: Shell Oil Company
    Inventors: Johannes L. M. Syrier, Johannes Van Berkel
  • Patent number: 4280011
    Abstract: The use of acetals as aldehyde generators in foodstuff applications is disclosed.
    Type: Grant
    Filed: April 5, 1978
    Date of Patent: July 21, 1981
    Assignee: Hercules Incorporated
    Inventor: Robert S. DeSimone
  • Patent number: 4275242
    Abstract: A process for preparing 2-methylenealdehydes by reacting aldehydes with formaldehyde in the presence of enamines is disclosed.
    Type: Grant
    Filed: December 21, 1979
    Date of Patent: June 23, 1981
    Assignee: Ruhrchemie Aktiengesellschaft
    Inventors: Jurgen Weber, Wolfgang Bernhagen, Helmut Springer
  • Patent number: 4273945
    Abstract: Saturated aliphatic, cycloaliphatic and araliphatic aldehydes are prepared by selective hydrogenation of the corresponding olefinically unsaturated aldehydes with hydrogen in the liquid phase over a palladium-containing catalyst, using a catalyst system in which the active constituents are from 2 to 90% by weight of palladium and from 10 to 98% by weight of an oxide or a salt of a rare earth metal or of a mixture of different oxides and/or salts of this type.
    Type: Grant
    Filed: July 5, 1979
    Date of Patent: June 16, 1981
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerd Heilen, Axel Nissen, Wolfgang Koernig, Michael Horner, Werner Fliege, Guenter Boettger
  • Patent number: 4273944
    Abstract: A novel method for the selective preparation of the cis isomer of a disubstituted ethylenically unsaturated compound is proposed in which a disubstituted acetylenically unsaturated compound is partially hydrogenated in the presence of, in place of a conventional Lindlar catalyst or a combination of a Lindlar catalyst with an amine, a palladium catalyst borne on an alumina carrier in combination with water and a hydroxide or a basic salt of an alkali metal or an alkaline earth metal. The inventive method is advantageous over conventional methods by the unnecessity of the use of an amine compound which is definitely undesirable when the product is directed to the application in perfumery and by the easiness in handling of the catalyst which can be easily separated from the reaction mixture after completion of the reaction.
    Type: Grant
    Filed: October 30, 1979
    Date of Patent: June 16, 1981
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Shigeru Ohno, Haruya Tezuka, Toshinobu Ishihara
  • Patent number: 4258207
    Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is an acyl group or certain optionally halo-substituted hydrocarbyl groups, and X is --CH.sub.2 CH(OCH.sub.3).sub.2, --CH.sub.2 CHO, --CH.dbd.CHOR.sup.2 in which R.sup.2 is acyl, --CHO, --C(O)Cl, --C(O)Br or --C(O)OR in which R is H, a salt-forming cation, an alkyl group or the residue of a pyrethroid alcohol are new pesticides or intermediates therefore. The compounds are prepared using a multi-step synthesis starting from the natural terpene, 3-carene.
    Type: Grant
    Filed: March 15, 1979
    Date of Patent: March 24, 1981
    Assignee: Shell Oil Company
    Inventor: Steven A. Roman
  • Patent number: 4258205
    Abstract: New 2,2-dimethylcyclopropanecarbaldehyde dimethyl acetal derivatives of the formula ##STR1## wherein X is --CH.sub.2 OC(O)CH.sub.3, --CH.sub.2 OH, or --CHO are useful chemical intermediates for the preparation of pesticidally active cyclopropanecarboxylates.
    Type: Grant
    Filed: December 4, 1978
    Date of Patent: March 24, 1981
    Assignee: Shell Oil Company
    Inventors: Johannes Van Berkel, Hendrik C. Kelderman
  • Patent number: 4252738
    Abstract: 1,2-Halohydrincarboxylic acid esters of the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are identical or different and represent hydrogen, cyano and optionally substituted alkyl, alkenyl, aralkyl, aryl, alkoxycarbonyl, acyloxy, alkoxy and aryloxy, and furthermoreR.sup.1 and R.sup.2 and/or R.sup.3 and R.sup.4, or R.sup.1 and R.sup.3 and/or R.sup.2 and R.sup.4 can be linked, forming a ring with the carbon atoms to which they are bonded;R.sup.5 represents hydrogen and optionally substituted alkyl, alkenyl, aralkyl, aryl, alkoxy and alkoxycarbonyl andX represents fluorine, chlorine, bromine and iodine; a process for preparing such 1,2-halohydrincarboxylic acid esters by reacting a cyclobutane-cis-1,2-diol of the formula ##STR2## with an orthoester of the formula ##STR3## wherein R.sup.1 -R.sup.5 have the previously ascribed significance and R.sup.6 -R.sup.
    Type: Grant
    Filed: March 17, 1978
    Date of Patent: February 24, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Willy Hartmann, Hans-Georg Heine
  • Patent number: 4242279
    Abstract: The invention relates to 2-(2,2-dihalovinyl)-3,3-dimethylcyclopropylacetones which are intermediates for the preparation of pyrethroids which have good insecticidal properties.
    Type: Grant
    Filed: September 24, 1979
    Date of Patent: December 30, 1980
    Assignee: Shell Oil Company
    Inventors: Pieter A. Verbrugge, Petrus A. Kramer
  • Patent number: 4241081
    Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is an acyl group or certain optionally halo-substituted hydrocarbyl groups, and X is --CH.sub.2 CH(OCH.sub.3).sub.2, --CH.sub.2 CHO, --CH.dbd.CHOR.sup.2 in which R.sup.2 is acyl,--CHO,--C(O)Cl, --C(O)Br or --C(O)OR in which R is H, a salt-forming cation, an alkyl group or the residue of a pyrethroid alcohol are new pesticides or intermediates therefore. The compounds are prepared using a multi-step synthesis starting from the natural terpene, 3-carene.
    Type: Grant
    Filed: July 23, 1979
    Date of Patent: December 23, 1980
    Assignee: Shell Oil Company
    Inventor: Steven A. Roman
  • Patent number: 4234512
    Abstract: 2-(2,2-Dimethoxyethyl-3,3-dimethylcyclopropanecarbaldehyde and 2-[2-(2,2-dihalovinyl)-3,3-dimethylcyclopropyl]ethanal dimethyl acetals are new pyrethroid intermediates. They are prepared from 2-(2-hydroxymethyl-3,3-dimethylcyclopropyl)ethanal dimethyl acetal.
    Type: Grant
    Filed: July 9, 1979
    Date of Patent: November 18, 1980
    Assignee: Shell Oil Company
    Inventors: Johannes Van Berkel, Hendrik C. Kelderman
  • Patent number: 4225694
    Abstract: Primary and secondary unsaturated alcohols are converted to their corresponding aldehydes and/or carboxylic acids and ketones respectively with alkali metal (per) halate, preferably sodium periodate, in the presence of ruthenium catalyst. The process is particularly useful in the oxidation of chrysanthemyl alcohol. Any unconverted intermediate aldehyde formed may be converted to the acid by recycling or by a separate oxidation step.
    Type: Grant
    Filed: September 6, 1977
    Date of Patent: September 30, 1980
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Augustine I. Dalton, Jr., Henry J. Doran, Robert D. H. Murray
  • Patent number: 4222964
    Abstract: 2-(2,2-Dihalovinyl-3,3-dimethylcyclopropyl)ethanal is a new chemical compound and useful intermediate in the preparation of certain pyrethroid esters. It is prepared by hydrolysis of 2-[2-(2,2-dihalovinyl)-3,3-dimethylcyclopropyl]ethylidene diacetate, preferably in the presence of an acid.
    Type: Grant
    Filed: July 9, 1979
    Date of Patent: September 16, 1980
    Assignee: Shell Oil Company
    Inventors: Johannes Van Berkel, Johannes L. M. Syrier, Hendrik C. Kelderman
  • Patent number: 4211727
    Abstract: Carboxylic acid halides are reduced to the corresponding aldehydes using zinc borohydride or cadmium borohydride as the reducing agent.
    Type: Grant
    Filed: March 15, 1979
    Date of Patent: July 8, 1980
    Assignee: Shell Oil Company
    Inventors: Ian D. Entwistle, Robert A. W. Johnstone
  • Patent number: 4209644
    Abstract: An unsaturated carbonyl compound, for example, one expressed by the following formula, ##STR1## is prepared by maintaining at an elevated temperature a novel allyl acetal of a .beta.,.gamma.-unsaturated aldehyde, for example, one expressed by the following formula ##STR2## The allyl acetal can be derived, for example, for 3-methyl-3-butenal-1 having 5 carbon atoms and prenyl alcohol having 5 carbon atoms. Thus, the unsaturated aldehyde having the increased number of carbon atoms can be formed in a high yield by a relatively simple reaction.
    Type: Grant
    Filed: November 30, 1977
    Date of Patent: June 24, 1980
    Assignee: Teijin Limited
    Inventors: Yataro Ichikawa, Teizo Yamaji, Mamoru Yamamoto
  • Patent number: 4209642
    Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is an acyl group or certain optionally halo-substituted hydrocarbyl groups, and X is --CH.sub.2 CH(OCH.sub.3).sub.2, --CH.sub.2 CHO, --CH.dbd.CHOR.sup.2 in which R.sup.2 is acyl, --CHO, --C(O)Cl, --C(O)Br or --C(O)OR in which R is H, a salt-forming cation, an alkyl group or the residue of a pyrethroid alcohol are new pesticides or intermediates therefore. The compounds are prepared using a multi-step synthesis starting from the natural terpene, 3-carene.
    Type: Grant
    Filed: March 15, 1979
    Date of Patent: June 24, 1980
    Assignee: Shell Oil Company
    Inventor: Steven A. Roman
  • Patent number: 4202822
    Abstract: Derivatives, analogs, and congeners of prostane having a 1-(hydroxymethyl)-1-oxo-prostane structure in the F.sub.1 series.
    Type: Grant
    Filed: December 8, 1977
    Date of Patent: May 13, 1980
    Assignee: American Cyanamid Company
    Inventor: Allan Wissner