Abstract: The present invention relates to an improved process for the production of 2-alkyl-3-butin-2-ols; especially to a new purification step.

Abstract: A novel catalyst useful in the ethynylation of formaldehyde to butynediol is formed by precipitating copper and bismuth from a salt solution of such metals, utilizing an alkali metal hydroxide as the precipitating agent to deposit copper and bismuth hydroxide as a coating around a siliceous carrier particle.

Abstract: Disclosed is a method for producing an alicyclic alcohol represented by general formula (III) which is useful as a starting material for a flavor mixture or the like at low cost in high yield. The alicyclic alcohol represented by general formula (III) is produced by preparing a cyclohexanecarbonyl compound represented by general formula (II) through the carbonylation of an unsaturated hydrocarbon represented by general formula (I) (preferably a compound obtained through the partial reduction of a diene compound) using carbon monoxide in the presence of HF, and thereafter reducing the cyclohexanecarbonyl compound. In formulae (I), (II), and (III), R1 represents an alkyl group having 1 to 4 carbon atoms, R2 represents an alkyl group having 1 to 4 carbon atoms, R3 represents an OH group, fluorine, or an OR4 group, and R4 represents an alkyl group having 1 to 4 carbon atoms.

Abstract: Unsaturated alcohol compositions are obtained by reducing a metathesis-derived hydrocarbyl unsaturated ester. Also disclosed is a process for preparing an unsaturated alcohol composition, where a metathesis derived hydrocarbyl carbonyl compound is reacted in the presence of a silane compound, an organic solvent, and a catalyst system prepared from a metallic complex and a reducing agent. This mixture is then hydrolyzed with a metallic base, and then mixed with organic solvent. The resultant mixture is then separated, washed, dried, and/or purified to produce the unsaturated alcohol composition. The unsaturated alcohol derivatives are useful in many end-use applications, including, for example, lubricants, functional fluids, fuels, functional additives for such lubricants, functional fluids and fuels, plasticizers, asphalt additives, friction reducing agents, plastics, and adhesives.

Abstract: The present disclosure is a method and system for electrochemically co-producing a first product and a second product. The system may include a first electrochemical cell, a first reactor, a second electrochemical cell, at least one second reactor, and at least one third reactor. The method and system for for co-producing a first product and a second product may include co-producing a glycol and an alkene employing a recycled halide.

Abstract: A method comprising applying a controlled flow cavitation apparatus to an alcohol production process in order to increase alcohol yield. A grain-based liquid medium comprising grain and a liquid carrier can be passed through a controlled flow cavitation apparatus at a velocity capable of generating a hydrodynamic cavitation zone where the grain size can be reduced. One or more controlled flow cavitation apparatuses can be applied at various points of an alcohol production process, such as a starch-to-ethanol production process.

Abstract: Disclosed is a method for producing an alcohol from a lactone or a carboxylic acid ester, which enables to produce an alcohol from a lactone or a carboxylic acid ester under relatively mild conditions with high yield and high catalytic efficiency. This method also enables to produce an optically active alcohol from an optically active lactone or an optically active carboxylic acid ester. Specifically disclosed is a method for producing an alcohol by hydrogen reducing a lactone or a carboxylic acid ester in the presence of a catalyst containing ruthenium and a phosphine compound represented by the following general formula (1): wherein R1 represents a spacer; R2, R3, R4, R5, R6 and R7 independently represent a hydrogen atom, an alkyl group having 1-12 carbon atoms, an aryl group or a heterocyclic group; and R8, R9, R10, R11, R12 and R13 independently represent an alkyl group having 1-12 carbon atoms, an aryl group or a heterocyclic group.

Abstract: Compounds of the formula (I) wherein R2 is a branched or unbranched, saturated or ethylenically mono or di unsaturated aliphatic radical, Z is —CH2OH, —CH2OAc or —CHO, m is a whole positive integer of one or more, and Ac is an acetyl group are synthesized by a process wherein a 1-alken-3-yl alkylate, is reacted with a halo alkanol Grignard reagent.

Abstract: A process for the preparation of terminally ethylenically unsaturated isopolyprenols characterized in that a carbonyl compound is reacted with ethine in the presence of ammonia and low amounts of an alkaline metal hydroxide and, if desired, the terminally acetylenically unsaturated isopolyprenol obtained is partially hydrogenated in the presence of a catalyst suitable for selective hydrogenation.

Abstract: A process for the manufacture of an acetylenically unsaturated alcohol comprising reacting formaldehyde, an aldehyde or a ketone (a carbonyl compound) with acetylene in the presence of ammonia and an alkali metal hydroxide, the molar ratio of the alkali metal hydroxide to the carbonyl compound being less than 1:200. The reaction products, which depending on the starting carbonyl compound are propargyl alcohol or 1-monosubstituted or 1,1-disubstituted derivatives thereof, are of use as intermediates in the synthesis of many useful end products, inter alia in the field of vitamins and carotenoids.

Abstract: A process for the preparation of terminally ethylenically unsaturated isopolyprenols characterized in that a carbonyl compound is reacted with ethine in the presence of ammonia and low amounts of an alkaline metal hydroxide and, if desired, the terminally acetylenically unsaturated isopolyprenol obtained is partially hydrogenated in the presence of a catalyst suitable for selective hydrogenation.

Abstract: The present invention provides a process for preparing propargyl alcohol by converting an aqueous formaldehyde solution comprising acetylene over a catalyst comprising copper acetylide at an operating pressure of from 1 to 15 bar and from 70 to 120° C. without forming a continuous gas phase, in which the aqueous formaldehyde solution comprises an organic solvent for acetylene and the catalyst is arranged in a fluidized bed.

Abstract: A process for the preparation of diols by a Lewis acid-catalysed aldehyde addition reaction on hydroxyalkynes followed by hydrogenation is described. The process provides a wide range of diols from simple, readily available starting materials. In particular the process is suitable for preparing chiral 1,4-diols suitable for the preparation of chiral phospholane ligands for use in asymmetric catalysis.

Abstract: The present invention relates to a process for the preparation of iron-doped ruthenium catalysts supported on carbon, and their use for the selective liquid phase hydrogenation of carbonyl compounds to give the corresponding alcohols, in particular for the hydrogenation of citral to give geraniol or nerol or of citronellal to give citronellol.

Abstract: A process for preparing at least one unsaturated alcohol (B) comprises the steps (I) to (III) below: (I) reaction of at least one alkali metal hydroxide or alkaline earth metal hydroxide with at least one alcohol (A) in at least one organic solvent (L) to give a mixture (G-I) comprising at least the alcohol (A), the solvent (L) and an alkoxide (AL); (II) reaction of at least one carbonyl compound of the formula R—CO—R? with at least one alkyne of the formula R?—C?C—H and the mixture (G-I) obtained in step (I) to give a mixture (G-II) comprising at least the alcohol (A), the solvent (L) and an unsaturated alcohol (B); (III) distillation of the mixture (G-II) obtained in step (II) to give the alcohol or alcohols (B) and a mixture (G-III) comprising the solvent (L) and the alcohol (A), wherein the solvent (L) obtained in step (III) and the alcohol (A) obtained in step (III) are recycled as a mixture to step (I).

Abstract: A process for the manufacture of an acetylenically unsaturated alcohol comprising reacting formaldehyde, an aldehyde or a ketone (a carbonyl compound) with acetylene in the presence of ammonia and a strongly basic macroporous anion exchange resin, the latter preferably featuring a polystyrene matrix and quaternary ammonium groups, preferably of type I or Type II. The reaction products, which depending on the starting carbonyl compound are propargyl alcohol or 1-monosubstituted or 1,1-disubstituted derivatives thereof, are of use as intermediates in the synthesis of many useful end products, inter alia in the field of vitamins and carotenoids.

Abstract: A process for the hydrogenation, using molecular hydrogen (H2) of a catalytic system, wherein the catalytic system includes a base and a complex of formula (II): Ru(P2N2)Y2??(II) wherein Y represent simultaneously or independently a hydrogen or halogen atom, a hydroxy group, or an alkoxy, carboxyl or other anionic radical, and P2N2 is a tetradentate diimino-diphosphine ligand.

Abstract: Higher &agr;,&bgr;-unsaturated alcohols are prepared by monoethynylation of a ketone by the NH3/KOH method, if desired hydrogenation of the acetylene alcohol in the presence of hydrogen over a Pd-containing thin layer catalyst, purifying distillation of the hydrogenation product, preferably in a dividing wall column with recirculation of the unreacted ketone to the ethynylation step, and, if desired, preparation of higher alcohols having in each case 5 more carbon atoms in the chain by reacting the alcohols prepared by monoethynylation and, if desired, partial hydrogenation with alkyl acetoacetates diketene in a Carroll reaction to form ketones and using these as starting materials for the steps ethynylation, optional hydrogenation and fractional distillation.

Abstract: A method of reacting a solution comprising a mixture of chemical compounds which are in chemical equilibrium with one another with at least one further chemical compound (9) is provided. The method comprises the following steps: fractionation of the solution by means of a separation method to give at least two fractions (5, 6) which are enriched in different chemical compounds of the mixture; and reaction of a fraction (5) with the further chemical compound or compounds (9). The fractionation is advantageously carried out using a film evaporator (1). Unreacted fractions (6) can be recirculated via a residence time vessel (3) back to the fractionation step. The method is particularly suitable for reactions of an aqueous formaldehyde solution in which various components of the solution (formaldehyde, methylene glycol, polyoxymethylene glycols) react in different ways.

Abstract: A process for producing an optically active propargyl alcohol represented by the following formula (4): wherein R1 is an alkyl group, a cycloalkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, an alkylsilyl group, an aromatic hydrocarbon group, a C2-C10 heterocyclic group having 1-3 heteroatoms or a C1-C10 alkyl group having 1-3 heteroatoms, and R2 is an alkyl group, a cycloalkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, an alkylsilyl group, an aromatic hydrocarbon group, a C2-C10 heterocyclic group having 1-3 heteroatoms or a C1-C10 alkyl group having 1-3 heteroatoms, which comprises allowing an aldehyde compound represented by the following formula (1): R1—CHO  (1) to react with an alkyne compound represented by the following formula (2): HC≡C—R2  (2) in the presence of an optically active aminoalcohol and a tertiary amine and a zinc halogenated lower alkane sulfonate in an amount of less than equivalent mo

Abstract: The invention provides a process for the preparation of 6,6-dimethylhept-1-en-4-yn-3-ol comprising of reacting t-butylacetylene with a proton-extracting agent selected from the group consisting of an organometallic compound and metallic lithium to form a t-butylacetylide, reacting the acetylide with acrolein at temperatures between −40° C. to +20° C., quenching the reaction mixture and isolating the product.

Abstract: The present invention provides a process for producing an acetylenediol continuously by reacting a ketone with acetylene in the presence of an alkali catalyst, which process comprises continuously feeding, into a first-stage reactor, a reaction solvent, an alkali catalyst, a ketone and acetylene to give rise to a reaction, continuously introducing the reaction mixture into a second-stage reactor, and continuously feeding a fresh portion of the same ketone into the second-stage reactor to give rise to a reaction.

Abstract: Higher &agr;,&bgr;-unsaturated alcohols are prepared by monoethynylation of a ketone by the NH3/KOH method, if desired hydrogenation of the acetylene alcohol in the presence of hydrogen over a Pd-containing thin layer catalyst, purifying distillation of the hydrogenation product, preferably in a dividing wall column with recirculation of the unreacted ketone to the ethynylation step, and, if desired, preparation of higher alcohols having in each case 5 more carbon atoms in the chain by reacting the alcohols prepared by monoethynylation and, if desired, partial hydrogenation with alkyl acetoacetatesor diketene in a Carroll reaction to form ketones and using these as starting materials for the steps ethynylation, optional hydrogenation and fractional distillation.

Abstract: In a process for isolating &agr;-ethynyl carbinols from the liquid reaction mixture from the addition of acetylene onto &agr;,&bgr;-unsaturated carbonyl compounds by distillation, the distillation is carried out continuously, the feed stream is introduced into the middle section of a distillation column (K), the major part of the water is distilled off azeotropically together with the solvent at the top of the column, and the &agr;-ethynyl carbinol target product is taken off below the feed point to the column.

Abstract: The invention relates to a method for producing alkyne diols by reacting ketones with acetylenic hydrocarbons in an organic solvent in the presence of a base which contains potassium alcoholates of primary and/or secondary alcohols. The alkyne diols are produced while forming adducts which precipitate out of the reaction mixture and which are comprised of alkyne monoalcohols and/or alkyne diols and a base. The stoichiometries of the reaction partners are selected such that gelatinous adducts are formed which comprise a spherical surface, whereby the reaction mixture remains agitable during the entire reaction.

Abstract: The present invention relates to a process for making propargylic alcohols by zinc-mediated catalytic, asymmetric addition of acetylenes to aldehydes.

Abstract: The invention provides processes for producing phytol, isophytol, and certain phytol derivatives by a method of oxidizing or epoxidizing geranylgeraniol or geranylgeraniol derivatives to form epoxygeranylgeraniol derivatives, reducing or hydrogenating the epoxygeranylgeraniol derivatives to produce epoxyphytol derivatives, and then deoxygenating the epoxyphytol derivatives to produce phytol, isophytol, phytene derivatives, isophytene derivatives, or mixtures thereof. The step of deoxygenating is carried out in the presence of deoxygenation catalysts, including rhenium trioxide compounds. The invention also provides methods for the synthesis of certain novel substituted epoxyphytyl compounds and substituted phytene compounds having removable protecting groups.

Abstract: There is disclosed a method for producing acetylene alcohol compounds in a continuous process, which are produced via ethynylation in which ketones containing a group --CH.sub.2 COCH.sub.2 --, are condensed with acetylenes at a temperature of about 20 to 50.degree. C. under a pressure of about 10 to 30 kg/cm.sup.2 in the presence of a quaternary ammonium hydroxide anion exchange resin having strong basicity in an aprotic solvent by feeding a reactant mixture at an LHSV range of 0.1 to 5.0 and the reactant mixture comprises the acetylene, the ketone and the solvent at a molar ratio of 1.0:0.2-3.0:1.0-4.0.

Abstract: Preparation of a monolithium acetylide/ammonia complex by the reaction of lithium amide and acetylene in ammonia, by carrying out the reaction at a temperature of from -10.degree. to 30.degree. C.

Abstract: A process for catalytic preparation of alcohols or amines by reaction of esters, fatty acids, or nitriles with hydrogen at elevated temperature and pressure. The unreduced catalyst contains, per 100 parts by weight of CuO, 40 to 130 parts by weight of ZnO, 2 to 50 parts by weight of Al.sub.2 O.sub.3, and optionally 0.5 to 8 parts by weight of oxide of Mn, Mo, V, Zr, and/or alkaline earth metal. It has a BET total area of 80 to 175 m.sup.2 /g of catalyst in the unreduced state, and 75% to 95% of the BET total area is formed by pores having a radius r.sub.p .ltoreq.15 nm.

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.

Abstract: A chemically and optically pure B-halodiiso-2-ethylapopinocampheylborane of essentially 100% ee represented by the formula: ##STR1## wherein B is borane and X is halo, and a process of using such for the production of optically active alcohols.

Abstract: The novel organoboron reagent of the present invention is useful in the preparation of unsubstituted propargylic alcohols. This compound reacts with aldehydes and ketones cleanly to afford propargylic alcohols in excellent yields Unsubstituted propargylic alcohols are important synthetic intermediates in the synthesis of a number of natural products. In addition, the novel organoboron reagent of the present invention also demonstrates diastereomeric selectivity when reacted with enatiomerically pure aldehydes.

Abstract: A process for the preparation of ethynyl carbinols of the formula: ##STR1## wherein R" is hydrogen, a substituted or unsubstituted aliphatic or aromatic hydrocarbon, R'" is a substituted or unsubstituted aliphatic or aromatic hydrocarbon or R" and R'" together to the carbon atom to which they are joined represent a steroid, which comprises the steps ofA. reacting in a solvent system comprising an aromatic hydrocarbon, at least one lithium alkylamide selected from the group consisting of: ##STR2## wherein R is a hydrogen or lower alkyl, R' is hydrogen, lower alkyl, a substituted or unsubstituted aliphatic, alicyclic or aromatic hydrocarbon, x is an integer of 2 to 8, y and z are each 0 to 1, with acetylene to form a monolithium acetylideB. reacting in a solvent system comprising an aromatic hydrocarbon, the monolithium acetylene from Part A with a ketone of the formula R"R'"C.dbd.O, wherein R" and R'" are as hereinbefore defined, and thenC.

Abstract: Unsaturated alcohols are prepared by hydrogenation of the corresponding carbonyl compounds in the presence of a platinum-cobalt bi-metallic catalyst having an alloy structure.

Abstract: A process for manufacturing an alkynediol is disclosed. In this process, a C.sub.3-12 ketone is reacted with acetylene in the presence of potassium hydroxide in an C.sub.1-4 alkyl-tert-butyl ether solvent. The potassium hydroxide is used in a molar ratio, relative to the amount of ketone used, of from 1.0:1.0 to 1.6:1.0.

Abstract: An enantioselective process for the preparation of homoallyl alcohol enantiomer of formula II ##STR1## wherein: X.sup.1, X.sup.2 and X.sup.3 independently chosen from the group consisting of hydrogen, chlorine, bromine, fluorine, iodine, C.sub.1 to C.sub.6 alkyl, C.sub.1 and C.sub.6 haloalkyl, and haloaryl; andR.sup.1, R.sup.2, R.sup.3 and R.sup.4 are independently chosen from the group consisting of hydrogen, halogen, alkyl, alkenyl, alkynyl, benzyl, substituted benzyl, phenyl, substituted phenyl; or R.sup.3 and R.sup.4 is as hereinbefore defined and R.sup.1 and R.sup.2 form a carbocyclic or heterocyclic ring; which process comprises; reacting an aldehyde of formula III with an alkene or formula IV in the presence of an optically-active organometallic catalyst. ##STR2## Furthermore, the compound of formula II can be isomerized to the allylic alcohol of formula I with retention of optical purity.

Abstract: An efficient method is proposed for the synthesis of an unsaturated alcohol of the general formula R--CH.dbd.CH(CH.sub.2).sub.n+1 OH, in which R is a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms and the subscript n is an integer in the range from 3 to 10, in which an acetate of the formula R--CH.dbd.CHCH.sub.2 OCOCH.sub.3 is subjected to a coupling reaction with a Grignard reagent of the formula X.sup.1 Mg(CH.sub.2).sub.n OMgX.sup.2, in which X.sup.1 and X.sup.2 are each a halogen atom, and then the reaction product is hydrolyzed. When the reaction product of the coupling reaction is reacted with acetic anhydride instead of hydrolysis, the corresponding acetate can readily be obtained. These unsaturated alcohols and acetates form a class of important biologically active compounds or intermediates thereof including sex pheromone compounds of insects.

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: A process for manufacturing propynol from formaldehyde and acetylene is disclosed. In this process the acetylene is first dissolved in a dimethoxymethane solvent under strong cooling and at slight gauge pressure. The cool acetylene-containing solution is then fed to a reactor charged with formaldehyde and a catalyst.

Abstract: Process for carrying out exothermic reactions between a gas and a liquid in the presence of a solid catalyst by passing the gas and the liquid cocurrently through a packed reaction vessel, preferably of elongated shape, wherein the gas and liquid pass through the packed reaction vessel in transition flow.

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.

Abstract: An asymmetric synthesis process which involves addition of optically active chelated organometal compounds of lithium, sodium, beryllium, magnesium, zinc, copper and cadmium to prochiral unsaturated substrates. The optically active chelating agent is not consumed and can be recycled.