Abstract: A process for producing homoallyl alcohols of the general formula (I) ##STR1## in which either A.sup.1 or A.sup.3 represents a hydrogen atom, the other represents a single bonding along with A.sup.2 ; R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are the same or different and independently represents a hydrogen atom, or an alkyl or alkenyl group with or without being substituted with a hydroxyl group or an akoxyl group; and Y represents a hydrogen atom, an alkyl group or an alkenyl group, by reacting 1,3-glycols of the general formula (II) ##STR2## in which X and Y are the same or different and independently represents a hydrogen atom, an alkyl group or an alkenyl group, R.sup.1, R.sup.2, R.sup.3, R.sup.4, and R.sup.5 independently represents as defined above, at a temperature in the range of 130.degree. to 250.degree. C. in liquid phase with the contact of .gamma.-alumina catalyst.

Abstract: Dien-1-ols of the general formula I ##STR1## where the radicals R.sup.1 to R.sup.7 are identical to or different from one another and each is hydrogen or straight-chain or branched alkyl of 1-12 carbon atoms and n is 1-14, are prepared by dehydrating a hydroxyalkenyl tert-butyl ether of the formula II ##STR2## in the presence of an acidic catalyst at elevated temperatures and essentially at the same time splitting off the tert-butyl protective group, as is 9-hydroxydodec-10-enyl 1-tert-butyl ether which is useful as an intermediate for synthesizing 8,10-dodecadienol.

Abstract: A process for producing an optically active alcohol represented by formula (I): ##STR1## wherein R.sub.1 is an alkyl group having from 2 to 11 carbon atoms, an alkenyl group having from 3 to 11 carbon atoms, an alkadienyl group having from 6 to 11 carbon atoms, a cyclohexyl group, an cyclohexylmethyl group, or a cyclohexylethyl group, provided that the olefin in the alkenyl group or alkadienyl group is not conjugated to the olefin at the 2-position thereof; and * means an asymmetric carbon atom,is disclosed, comprising subjecting an olefinic alcohol represented by formula (II): ##STR2## wherein R.sub.1 is the same as defined above to asymmetric hydrogenation in the presence of, as a catalyst, a ruthenium-optically active phosphine complex.According to the process of the invention, the desired optically active alcohols which are useful not only as intermediates for the manufacture of perfumes and vitamin E but also as liquid crystal materials can be produced with high optical purities.

Abstract: The invention concerns a method for the preparation of polyoxyalkylene compounds wherein each compound has one primary amine group and one primary hydroxyl group. The method comprises alkoxylating a t-butyl ethylene, propylene or butylene glycol then aminating the product. Finally the t-butyl group is cleaved by an acid. The compounds of the method of this invention are useful in urethane/urea plastics including foams, elastomers and coatings.

Abstract: A method of manufacturing 2-propyn-1-ol by decomposing 2-butyn-1,4-diol in the presence of a copper acetylide catalyst. 2-propyn-1-ol is produced at high conversion, yield, and purity.

Abstract: The present invention relates to a process for producing an E,Z-9-alkenyl-1-aldehyde component which comprises:(a) disproportionating cyclooctene and an .alpha.-olefin in the presence of a suitable disproportionation catalyst under disproportionation conditions suitable to form a 1,9-alkadiene;(b) reacting the 1,9-alkadiene obtained in step (a) with a suitable metallating agent under conditions suitable to form a 1-metallo-9-alkene;(c) contacting the 1-metallo-9-alkene obtained in step (b) with oxygen under conditions suitable to form a 1-oxymetallo-9-alkene;(d) hydrolyzing the 1-oxymetallo-9-alkene suit a suitable hydrolyzing agent, under suitable hydrolyzing conditions to form E,Z-9-alkenyl-1-alcohol.(e) oxidizing said E,Z-9-alkenyl-1-alcohol with a suitable oxidizing agent under oxidizing conditions suitable to form E,Z-9-alkenyl-1-aldehyde.

Abstract: In order to produce pure alpha, omega-C.sub.4 to C.sub.20 alkenols having purities in excess of 90% by dehydrating the corresponding alpha, omega-C.sub.4 to C.sub.20 diols, a catalyst is used which was prepared by using an alkaline earth orthophosphate or alkaline earth hydrogen phosphate or by reacting an alkaline earth compound with phosphoric acid into the corresponding phosphate and then adding an alkali or alkaline earth compound. This catalyst is suitable to be shaped, next it is dried and then calcined at temperatures between 350.degree. and 950.degree. C. The educt dehydration takes place at temperatures between 300.degree. and 500.degree. C. in selective and partial manner to obtain pure alpha, omega-C.sub.4 to C.sub.20 alkenols at conversions exceeding 90%.

Abstract: This invention relates to a process for selectively cleaving a polyalkylene glycol, e.g., diethylene glycol, containing at least one ether group therein at a carbon-to-oxygen covalent bond and independently at a carbon-to-carbon covalent bond by heating the polyalkylene glycol with molecular hydrogen in the presence of a hydrogenation catalyst containing ruthenium to produce at least one of monoethylene glycol monomethyl ether, monoethylene glycol and ethanol. The production rate of each of said monoethylene glycol monomethyl ether, monoethylene glycol and ethanol is at least about 10 moles/kilogram ruthenium/hour.

Abstract: An olefinically unsaturated compound, in particular a very pure cis-isomer of an alkenylhydroxy compound of the formulaCH.sub.3 (CH.sub.2).sub.m --CH.dbd.CH--(CH.sub.2).sub.n --OR (I),where R is hydrogen or a protective group which can virtually be eliminated, m is from 1 to 12 and n is from 1 to 10, is obtained by catalytic partial hydrogenation of the corresponding acetylene derivative over a supported catalyst which contains from 0.05 to 5% by weight of palladium and from 0.05 to 15% by weight of zinc and/or cadmium.

Abstract: This invention relates to a process for selectively cleaving a polyalkylene glycol, e.g., diethylene glycol, containing at least one ether group therein at a carbon-to-oxygen covalent bond and independently at a carbon-to-carbon covalent bond by heating the polyalkylene glycol with molecular hydrogen in the presence of a hydrogenation catalyst containing iridium to produce at least one of monoethylene glycol monoethyl ether, monoethylene glycol monomethyl ether, monoethylene glycol and ethanol. Monoethylene glycol monoethyl ether can be produced in significant amounts by employing the process of this invention.

Abstract: Novel peroxide compounds and the use thereof. In particular, the present invention concerns .beta.-hydroxycyclopentylperoxide compounds of the general formula: ##STR1## wherein R.sub.1 represents hydrogen or an organic residue of 1 to 9 carbon atoms. These novel peroxide compounds are useful as an intermediate in the production of glutaraldehydes.

Abstract: The trans-isomer of an ethylenically unsaturated organic compound of the formula R.sup.1 CH.dbd.CHR.sup.2, in which R.sup.1 and R.sup.2 are each a substituted or unsubstituted monovalent hydrocarbon group, is selectively prepared in a high yield by the reduction of the corresponding acetylenically unsaturated organic compound of the formula R.sup.1 C.tbd.CR.sup.2. The method comprises reducing the starting compound in a hydrocarbon solvent containing an alkali metal dispersed therein in the presence of a proton donor compound such as an alcohol or a carboxylic acid at a temerature of 50.degree. to 150.degree. C.

Abstract: There is disclosed a novel process for converting allylic amines, having a hydrogen bonded to a carbon .delta. to the amino group, to a diene in the presence of a zero valent palladium phosphine complex and a weak acid. The process has been used to make novel compositions containing 7-methoxy-3,7-dimethyloctadienes which are useful as odorants and flavorants.

Abstract: New unsaturated fatty alcohols of the formula: ##STR1## in which n=2 or 4 are provided and are prepared by the novel process of reacting butadiene with water in the presence of a palladium salt and orthoboric acid, B(OH).sub.3, in a polar aprotic solvent.

Abstract: A novel substituted diene alcohol represented by a general formula: ##STR1## wherein X represents a group of the formula ##STR2## and a process for the preparation thereof wherein a lower alkoxycarbonyl group of a substituted diene carboxylic acid ester having an E configuration obtained by the treatment of a chrysanthemic acid ester with Bronsted acid or a substituted diene carboxylic acid ester having a Z configuration obtained by the thermal cleavage of a chrysanthemic acid ester is reduced to methylol derivative.

Abstract: New unsaturated fatty alcohols of the formula: ##STR1## in which n=2 or 4 are provided and are prepared by the novel process of reacting butadiene with water in the presence of a palladium salt and orthoboric acid, B(OH).sub.3, in a polar aprotic solvent.

Abstract: n-Octanol is obtained by (i) reacting butadiene with water in a solution containing water, a carbonate and/or bicarbonate salt of a monodentate tertiary amine, and sulpholane in the presence of a palladium compound and a hydrophilic monodentate phosphine, to form 2,7-octadien-1-ol; (ii) extracting 2,7-octadien-1-ol from at least part of the reaction mixture obtained in step (i) with a saturated aliphatic hydrocarbon, a monoolefinic hydrocarbon or an alicyclic hydrocarbon, and recycling the extraction residue to the 2,7-octadien-1-ol synthesis step (i); (iii) subjecting the extract layer containing 2,7-octadien-1-ol as obtained in step (ii) to distillation to distill off a large proportion of the extracting solvent therefrom, followed by distillation in the presence of water, whereby the extracting solvent remaining is distilled off in the form of an azeotropic mixture with water, to obtain a distillation residue; (iv) recovering 2,7-octadien-1-ol from the distillation residue obtained in step (iii) by distill

Abstract: Polyhydroxylated compounds such as glucose, sucrose, sorbitol, etc. are subjected to a hydrogenolysis reaction at hydrogenolysis conditions which include a temperature in the range of from about 175.degree. to about 250.degree. C. and a pressure in the range of from about 10 to about 2000 pounds per square inch in the presence of a catalytic composition of matter. The catalyst comprises a carbonaceous pyropolymer possessing recurring units containing at least carbon and hydrogen atoms which is impregnated with a transition metal. The products which are obtained will include alcohols, acids, ketones, ethers, and hydrocarbons.

Abstract: 3-Buten-1-ol is synthesized from 1,3-butanediol by heating a polyol in the resence of a trivalent metal sulfate to a temperature from about 70.degree. C. below to about 100.degree. C. above the boiling point of 1,3-butanediol.

Abstract: Described is the novel compound genus defined according to the structure: ##STR1## wherein R.sub.1 is selected from the group consisting of C.sub.1 -C.sub.3 alkyl useful in augmenting or enhancing the aroma or taste of consumable materials including perfumes, colognes, perfumed articles (including a solid or liquid anionic, cationic, nonionic or zwitterionic detergents) smoking tobacco and smoking tobacco articles.

Abstract: The process for producing C.sub.4 -C.sub.10 ethylene alcohols of the formula: ##STR1## wherein (a) R.sub.1 is --CH.sub.2 OH, R.sub.2 =R.sub.3 =--H;(b) R.sub.1 is --H, R.sub.2 =--CH.sub.3, R.sub.3 =--CH.sub.3 or --C.sub.6 H.sub.11comprises hydrogenation of acetylene alcohols of the formula: ##STR2## wherein (a) R.sub.1 is CH.sub.2 OH, R.sub.2 =R.sub.3 =--H;(b) R.sub.1 is --H, R.sub.2 is --CH.sub.3, R.sub.3 is --CH.sub.3 or --C.sub.6 H.sub.11,in the form of technical products in the liquid phase on a membrane catalyst made of an alloy consisting of palladium and ruthenium at a mass ratio therebetween of 90-94:10-6 respectively. Hydrogenation of said alcohols is effected by means of hydrogen diffusing through a membrane catalyst at a temperature of from 60.degree. to 180.degree. C. under atmospheric pressure of hydrogen. The process is simple in its scheme and the equipment employed. It avoids losses of noble metals of the catalyst and makes it possible to obtain the desired products in a yield of up to 99.

Abstract: A process for the preparation of a hydrogenation catalyst which contains the oxides of the metals nickel, copper, molybdenum and aluminum and/or iron, and may or may not contain manganese oxide, by precipitating a solution of salts of the metals with an alkali metal carbonate at from 35.degree. to 95.degree. C. and a pH of from 5 to 9 and heating the precipitate at from 350.degree. to 700.degree. C., the amount of the metal salts being selected so that the catalyst contains from 5 to 70 percent by weight of aluminum oxide and/or iron oxide, the remainder being principally nickel oxide and, based on nickel oxide, from 20 to 40 percent by weight of copper oxide, from 0.5 to 6 percent by weight of molybdenum oxide and from 0 to 10 percent by weight of manganese oxide.

Abstract: 3,6-Dimethyl-3-hydroxy-oct-1-ynes and -oct-1-enes and their esters with lower alkanoic acids, of the general formula I ##STR1## where X and Y are H or the two X's and/or the two Y's together are a further bond between the carbon atoms on which they are present, and R is H, --CO--CH.sub.3, --CO--C.sub.2 H.sub.5 or --CO--C.sub.3 H.sub.7, their use as scents, and a process for the preparation of 3,6-dimethyl-3-hydroxy-octane. The novel compounds exhibit interesting, predominantly floral, woody, herbal and fruity notes. The alcohols of the formula I are of particular importance because they serve as intermediates for a novel and particularly advantageous method of obtaining 3,6-dimethyl-3-hydroxy-octane, a compound required in large amounts as a fragrance for soaps and detergents.

Abstract: Rose oxide, which is an important olfactive compound valuable in the art of perfumery, is advantageously produced from citronellol through a novel synthetic route comprising(1) anodic alkoxylation of citronellol using as a supporting electrolyte an alkali metal aromatic sulfonate,(2) dealkoxylation of the resulting 2,6-dimethyl-3-alkoxyoct-1-en-8-ol in the presence of a palladium or nickel complex, and then(3) cyclization of the resulting dehydrocitronellol in the presence of an acid.

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.

Abstract: A process for producing .omega.-alkene-1-ols which comprises reacting an .alpha.,.omega.-alkanediol having 4 to 14 carbon atoms with a fatty acid selected from the group consisting of stearic acid, palmitic acid and a mixture of stearic acid and palmitic acid.

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.

Abstract: A process for preparing an .alpha.,.omega.-C.sub.6 - to C.sub.20 -alkenol of a purity of greater than 85% comprises catalytically dehydrating the corresponding .alpha.,.omega.-C.sub.6 - to C.sub.20 -diol using a catalyst of a neutral, pyrophosphate of lithium, sodium, strontium or barium or a mixture thereof at a temperature of 300.degree.-500.degree. C. and a diol conversion of 10-90%.

Abstract: The present invention relates to a process for the preparation of non-pyrophoric catalyst having controlledparticle size and activity comprising suspending active charcoal of homogeneous pore distribution in a diluted solution of a palladium salt or salt complex, if desired in the presence of an aliphatic alcohol, stirring the solution, filtering the catalyst coal, followed by treatment of the sorbed palladium salt or salt complex with alkali if desired and stirring it as long as required for the accumulation of the sorbed palladium compounds, reducing same by methods known, repeating the above mentioned steps, if desired any number of times and drying the obtained catalyst after washing.

Abstract: Primary alcohol containing impurities which have internal hydroxyl groups is purified to cause removal of such internal hydroxyl groups with reduced formation of ethers by treating the impure alcohol with an alumina catalyst which has been contacted with a hydroxide of a Group 1-A element. Preferably the alcohol treatment is concurrent with or followed by a hydrogenation treatment the purpose of which is to improve the iodine number of the treated alcohol.

Abstract: Aliphatic unsaturated material or compounds are hydrogenated. Specifically, unsaturated dinitrile, e.g., 5-methyl-4-nonenedinitrile, 2,4-dimethyl-4-octenedinitrile, 2,4-dimethyl-3-octenedinitrile, 2,4,6-trimethyl-3-heptenedinitrile, 5-methylenenonanedinitrile, 2-methyl-4-methyleneoctanedinitrile and 2,6-dimethyl-4-methyleneheptanedinitrile, in a mixture resulting from reaction of isobutylene and acrylonitrile are hydrogenated in presence of a palladium hydrogenation catalyst disposed on an active alumina support also having disposed thereon an adjuvant selected from cerium, thorium, manganese, praseodymium, neodymium and samarium. A specific combination of adjuvants namely cerium together with lanthanum was found to improve the hydrogenation at low levels of cerium.Other aliphatic compounds which can be hydrogenated according to the invention include among others ethylene, 1,3-butadiene, cinnamic acid, 5-methyl-4-nonenedicarboxylic acid, diethyl 5-methylene-nonanedicarboxylate, etc.

Abstract: A process for the synthesis of perfume products, Vitamin E and intermediates described herein involving a coupling reaction. For instance, a process for the synthesis of dehydrophytol and Vitamin E comprising forming a C.sub.15 acetylene from hexahydropseudoionone and then coupling said acetylene with 1-acetoxy-4-chloro-3-methylbut-2-ene to form a C.sub.20 acetoxy-enyne. The latter is readily subjected to partial hydrogenation and saponification in that order to form a dehydrophytol, a useful intermediate for the synthesis of Vitamin E and other products.

Abstract: Structural modification of olefinically unsaturated alcohols is achieved by contacting the unsaturated alcohol under reaction conditions with a catalytic amount of a catalyst composition comprising a ruthenium hydride complex of tertiary phosphine ligands.

Abstract: Process for production of ethylenic compounds by hydrogenating the corresponding alkynol with isopropyl alcohol in the presence of a metal complex such as IrH.sub.3 CO(P.phi..sub.3).sub.2 and IrH.sub.3 (P.phi..sub.3).sub.2.

Abstract: 2-ALKOXYTETRAHYDROFURANS ARE CONVERTED TO 1,4-DIOLS UNDER HYDROLYSIS-HYDROGENATION CONDITIONS. The method may be coupled with the synthesis of 2-alkoxytetrahydrofurans to provide a highly efficient, two-step conversion of allylic alcohols to butanediols.