Abstract: The invention relates to an improved process for preparing 3-aminomethyl-3,5,5-trimethylcyclohexylamine, referred to hereinafter as isophoronediamine or, in abbreviated form, IPDA, by: I. preparation of isophorone by catalyzed aldol condensations with acetone as reactant; II. reaction of isophorone with HCN to form isophoronenitrile (IPN, 3-cyano-3,5,5-trimethylcyclohexanone); III. catalytic hydrogenation and/or catalytic reductive amination (also referred to as aminative hydrogenation) of 3-cyano-3,5,5-trimethylcyclohexanone, hereinafter called isophoronenitrile or, in abbreviated form, IPN, to give the isophoronediamine.

Abstract: The present invention provides a catalyst used for manufacturing an optically active carbonyl compound by selective asymmetric hydrogenation of an ?, ?-unsaturated carbonyl compound, which is insoluble in a reaction mixture, and a method for manufacturing the corresponding optically active carbonyl compound. Particularly, the invention provides a catalyst for obtaining an optically active citronellal useful as a flavor or fragrance, by selective asymmetric hydrogenation of citral, geranial or neral. The invention relates to a catalyst for asymmetric hydrogenation of an ?, ?-unsaturated carbonyl compound, which comprises: a powder of at least one metal selected from metals belonging to Group 8 to Group 10 of the Periodic Table, or a metal-supported substance in which the at least one metal is supported on a support; an optically active cyclic nitrogen-containing compound; and an acid, and also relates to a method for manufacturing an optically active carbonyl compound using the same.

Abstract: The invention relates to a process for the production of hexahydro-iso-alpha-acids starting from iso-alpha-acids (or tetrahydro-iso-alpha-acids) in which iso-alpha-acids (or tetrahydro-iso-alpha-acids) are mixed with a heterogeneous ruthenium containing catalyst, that catalyzes the hydrogenation from iso-alpha-acids or tetrahydro-iso-alpha-acids to hexahydro-iso-alpha-acids, either in solvent-free conditions, or in the presence of a solvent phase (e.g. carbon dioxide, water, ethanol or another organic solvent, or mixtures thereof), and in the absence or presence of other hop compounds (such as beta-acids).

Abstract: The present invention provides a catalyst used for manufacturing an optically active carbonyl compound by selective asymmetric hydrogenation of an ?, ?-unsaturated carbonyl compound, which is insoluble in a reaction mixture, and a method for manufacturing the corresponding optically active carbonyl compound. Particularly, the invention provides a catalyst for obtaining an optically active citronellal useful as a flavor or fragrance, by selective asymmetric hydrogenation of citral, geranial or neral. The invention relates to a catalyst for asymmetric hydrogenation of an ?, ?-unsaturated carbonyl compound, which comprises: a powder of at least one metal selected from metals belonging to Group 8 to Group 10 of the Periodic Table, or a metal-supported substance in which the at least one metal is supported on a support; an optically active cyclic nitrogen-containing compound; and an acid, and also relates to a method for manufacturing an optically active carbonyl compound using the same.

Abstract: Provided is an industrially superior method for producing cyclohexyl alkyl ketones, which solves the problems in process reduction and in disposal of wastes such as metals. An aromatic ketone represented by a formula (1) is nuclear-hydrogenated with pressurized hydrogen and in the presence of a solvent at a temperature of from 20 to 120° C., in the presence of a catalyst that carries from 0.

Abstract: The invention relates to a process for the production of hexahydro-iso-alpha-acids starting from iso-alpha-acids (or tetrahydro-iso-alpha-acids) in which iso-alpha-acids (or tetrahydro-iso-alpha-acids) are mixed with a heterogeneous ruthenium containing catalyst, that catalyzes the hydrogenation from iso-alpha-acids or tetrahydro-iso-alpha-acids to hexahydro-iso-alpha-acids, either in solvent-free conditions, or in the presence of a solvent phase (e.g. carbon dioxide, water, ethanol or another organ-ic solvent, or mixtures thereof), and in the absence or presence of other hop compounds (such as beta-acids).

Abstract: Method of preparing 3,3,5,5-tetramethylcyclohexanone comprising step (i): (i) converting isophorone to 3,3,5,5-tetramethylcyclohexanone in the presence of methylmagnesium chloride. The thus prepared 3,3,5,5-tetramethylcyclohexanone may be employed in a method of preparing 1-amino-1,3,3,5,5-pentamethylcyclohexane (Neramexane) or a pharmaceutically acceptable salt thereof.

Abstract: The present invention relates to a method for preparing cyclohexanone from phenol in a first process, the first process being a cyclohexanone production process comprising hydrogenating phenol to form a product stream comprising cyclohexanone, phenol and side-products (RSP), including cyclohexanol and undesirable side-product; separating at least part of the product stream having a lower boiling point than cyclohexanone have been removed, into a first fraction comprising cyclohexanone and a second fraction comprising phenol, cyclohexanol and RSP, using distillation; and separating the second fraction into a third fraction, rich in cyclohexanol and comprising RSP, and a fourth fraction, rich in phenol and comprising RSP, using distillation. The invention further relates to an installation for carrying out a method of the invention.

Abstract: Provided is an industrially superior method for producing cyclohexyl alkyl ketones, which solves the problems in process reduction and in disposal of wastes such as metals. An aromatic ketone represented by a formula (1) is nuclear-hydrogenated with pressurized hydrogen and in the presence of a solvent at a temperature of from 20 to 120° C., in the presence of a catalyst that carries from 0.

Abstract: The present disclosure relates to a method for preparing a metal catalyst comprising at least one ligand that is coordinated to the metal through at least one phosphorous (P) atom and at least one nitrogen (N) atom, the method comprising reacting a metal pre-cursor complex with an acid ad salt of an aminophosphine, diaminophosphine, aminodiphosphine or diaminodiphosphine, in the presence of a base.

Abstract: By intramolecular condensation reaction of 2,15-hexadecanedione in a gaseous phase with a compound of a Group II element of the Periodic Table as a catalyst, 3-methyl-cyclopentadecenones is generated. Magnesium oxide, calcium oxide, or zinc oxide is desirable as the catalyst for the intramolecular condensation reaction. (R)- and (S)-muscone is generated by subjecting 3-methyl-cyclopentadecenones obtained as above to hydrogenation by using a catalyst. Palladium catalyst is desirable as the hydrogenation catalyst. Optically active muscone is generated by separating 3-methyl-cyclopentadecenones into respective components thereof by means of precision distillation and subsequently subjecting the separated 3-methyl-cyclopentadecenones to asymmetric hydrogenation by using an optically active ruthenium complex catalyst. The production methods described above enable easy and economical production of 3-methyl-cyclopentadecenones, (R)- and (S)-muscone, and optically active muscone.

Abstract: The present invention relates to a method for preparing cyclohexanone from phenol in a first process, the first process being a cyclohexanone production process comprising hydrogenating phenol to form a product stream comprising cyclohexanone, phenol and side-products (RSP), including cyclohexanol and undesirable side-product; separating at least part of the product stream having a lower boiling point than cyclohexanone have been removed, into a first fraction comprising cyclohexanone and a second fraction comprising phenol, cyclohexanol and RSP, using distillation; and separating the second fraction into a third fraction, rich in cyclohexanol and comprising RSP, and a fourth fraction, rich in phenol and comprising RSP, using distillation. The invention further relates to an installation for carrying out a method of the invention.

Abstract: The present application relates to a process for reacting a composition I comprising at least one aldehyde with hydrogen in the presence of a catalyst in at least one main reactor and at least one postreactor, wherein at least 50% of the fresh hydrogen fed to the reaction system is fed into at least one postreactor. In a preferred embodiment, composition I comprises at least one further organic compound.

Abstract: Provide that a useful catalyst for homogeneous hydrogenation, particularly a catalyst for homogeneous asymmetric hydrogenation for hydrogenation, particularly asymmetric hydrogenation, which is obtainable with comparative ease and is excellent in economically and workability, and a process for producing a hydrogenated compound of an unsaturated compound, particularly an optically active compound using said catalyst with a high yield and optical purity.

Abstract: The invention relates to a method for producing cyclohexadecanone by hydrogenating cyclohexadecenone, to mixtures of aromatic substances, and to products containing the inventive cyclohexadecanone.

Abstract: The present invention relates to certain ?-decalone derivatives which can impart useful odor notes of the pheromone or costus type. The present invention concerns the use of the compounds in the perfumery industry to impart such odor notes as well as to the compositions or articles that contain these compounds.

Abstract: A process for preparing a ketone, in particular cyclododecanone, by reacting cyclododecatriene with dinitrogen monoxide to obtain cyclododecadienone and hydrogenating the resulting cyclododecadienone, in particular to give cyclododecanone.

Abstract: The compound (Z)-7-cyclohexadecen-1-one is described as a musk odorant. Also described are odorant or aroma mixtures comprising (Z)-7-cyclohexadecen-1-one and one or more other odorants or aromas.

Abstract: Processes for producing higher molecular weight ketones are disclosed that include the steps of feeding an aldol catalyst solution, a lower molecular weight aldehyde, and a lower molecular weight ketone, through a reactor provided with a solid hydrogenation catalyst and hydrogen gas; recovering a liquid reactor effluent containing the higher molecular weight ketone as a reaction product; and recycling a portion of the recovered liquid reactor effluent back through the reactor.

Abstract: A method for producing a ketone, particularly a macrocyclic ketone, from a 2-hydroxycycloalkanone having from 12 to 18 carbon atoms by efficiently dehydrating and reducing the acyloin in a single reaction vessel. A method for producing a ketone compound, which comprises dehydrating and reducing an acyloin in the coexistence of an acid catalyst and a reduction catalyst and in the presence of hydrogen, particularly using a 2-hydroxycycloalkanone having from 12 to 18 carbon atoms as the acyloin.

Abstract: The invention concerns a method for preparing ketones of formula (I) wherein A and B are as defined in claim 1, consisting of reacting at a temperature ranging between 250 and 500° C. a compound of formula (II): A—X with a compound of formula (III): B—Y, wherein A, B, X and Y are as defined in claim 1, in a coolant solvent having a boiling point higher than 250 ° C.

Abstract: Methods and compositions are provided for the direct catalytic asymmetric aldol reaction of aldehydes with donor molecules selected from ketones and nitroalkyl compounds. The reactions employ as catalyst a Group 2A or Group 2B metal complex of a ligand of formula I, as defined further herein.

Abstract: A process for conducting multiphase reactions, especially the preparation of &agr;,&bgr;-unsaturated ketones by condensation of aldehydes with ketones.

Abstract: This invention describes heretofore unknown forms of dihydro (DHIA) and hexahydro (HHIA) isoalpha acids having a high ratio of trans to cis isomers and a process for their production. Also, non-precipitating clear 5, 10, 20% and higher aqueous solutions thereof, since they are soluble at room temperature in soft water. This is due to the high ratio of trans to cis isomers. Unlike prior art essentially all cis isomer products, they remain haze free both at a neutral pH in water and at 1% to 2% and higher concentrations. This invention has the advantage over the prior art in that DHIA and HHIA can be provided as stable, non-separating liquids, at practical concentrations in the range of 5% to about 40%, which do not require heating to about 50° to 90° C. and above with stirring to effect dissolution of precipitates. The high trans products described herein can be admixed with isoalpha- and tetrahydro-isoalpha acids.

Abstract: A cyclododecanone compound is continuously produced by an isomerization reaction of a corresponding epoxycyclododecane compound in the presence of a catalyst including lithium bromide and/or lithium iodide, the isomerization reaction being carried out by passing a reaction mixture containing the epoxycyclododecane compound and the catalyst through a continuous reaction apparatus including at least one tubular reactor preferably at a temperature of 100 to 350° C.

Abstract: Preparation of cyclic, &agr;,&bgr;-unsaturated ketones of formula II by dehydrogenation of cyclic ketones which conform to formula I in which n denotes an integer from 1 to 10, and which may be substituted, at elevated temperature in the presence of catalysts in the vapor phase, wherein the reaction is carried out in the absence of oxygen or in the presence of less than 0.5 mol of oxygen per mol of compound I at temperatures ranging from 250° to 600° C. and using catalysts having a surface area (BET) of more than 0.5 m2/g.

Abstract: A process for obtaining Ketone of formula 1a,b, which includes contacting a Ketone represented by formula 2a,b with a first catalyst under conditions and for a time sufficient to obtain an intermediate mixture, which intermediate mixture contains a Ketone represented by formula 4a,b; and contacting the intermediate mixture, or a fraction thereof, with a second catalyst under conditions effective to provide a product containing a Ketone of formula 1a,b. Moreover, the first catalyst preferably differs from the second catalyst with the first catalyst preferably being an isomerization catalyst and the second catalyst being a cyclization catalyst. The process is capable of providing unexpectedly incresased yields of both Ketone 4 and Ketone 1.

Abstract: Substituted or unsubstituted cyclopentadienyl are prepared by reducing 4-ketocyclopentene to an alcohol, replacing the hydroxyl functionality with a leaving group and deprotonating the resulting product under base induced elimination conditions.

Abstract: An alkaline earth metal salt of &bgr;-diketo compound is produced using 1 mol of a powdery alkaline earth metal compound and 2.04 mol or more of an aliphatic &bgr;-diketo compound. The reaction may be carried out while supplying both components to a reactor continuously or intermittently, or may be carried out by adding one component to the other continuously or intermittently. The highest temperature during the reaction may be at 50° C. or higher. The reaction mixture may be aged, and then dried at a temperature of at 100 to 180° C. in an atmosphere of an inert gas. The alkaline earth metal compound may be calcium hydroxide, magnesium hydroxide, or barium hydroxide. The aliphatic &bgr;-diketo compound may be represented by the following formula, particularly an acetoacetic acid ester or acetylacetone. According to the production method as mentioned above, highly stable alkaline earth metal salts of &bgr;-diketo compounds of high quality can be produced.

Abstract: Provided is a method for the production of 1-menthol, which comprises hydrogenation of piperitenone with a transition metal complex of a specified optically active phosphine to produce pulegone, hydrogenation of the obtained pulegone with a ruthenium-phosphine-amine complex in the presence of base to obtain pulegol, and further hydrogenation of the pulegol with a transition metal catalyst.

Abstract: A method of preparing tetrahydroiso-&agr;-acids from iso-&agr;-acids is disclosed wherein the reaction medium is a buffered, aqueous alcoholic solution. The method can also employ up to 85% w/w spent hydrogenation catalyst. The method advantageously avoids the formation of undesirable side products.

Abstract: A process for the carbonylation of saturated hydrocarbons to give an oxygenated saturated hydrocarbon is disclosed and claimed. The process involves using an acidic ionic liquid catalyst to catalyze the carbon monoxide addition to the saturated hydrocarbon at reaction conditions to form an oxygenate. The acidic ionic liquid comprises a Lewis or Bronsted acid in combination with a quaternary nitrogen-containing compound. A specific example is a mixture of aluminum chloride and n-butylpyridinium chloride.

Abstract: Proposed is a method of producing alkaline-earth salts of aliphatic .beta.-keto compounds by reacting alkaline-earth hydroxides with aliphatic .beta.-ketoesters and/or .beta.-diketones in the absence of solvent to give the corresponding alkaline-earth salts. The .beta.-keto compound is added in portions to the powdered alkaline-earth hydroxide and the reaction mixture subsequently dried. Good yields are obtained of a fine-grained, light colored product.

Abstract: Carbon dioxide is used as a reaction solvent in the hydrogenation of organic compounds. The carbon dioxide is preferably a liquid or a supercritical fluid. The hydrogenation method can be used advantageously in methods for making tetrahydroiso-alpha-acids from alpha-acids, iso-alpha-acids, or beta-acids. If beta-acids are used to make tetrahydroiso-alpha-acids, an acidic lower alcohol is preferably added to the carbon dioxide reaction medium to act as a promoter.

Abstract: Cyclohexane is catalytically oxidized to produce cyclohexanol and cyclohexanone and precursors of these products. The oxidation is carried out in a liquid oxidation reactor at high oxygen concentrations (greater than 30% and preferably greater than 90% oxygen concentration) and at relatively low temperatures (less than 160.degree. C.). The use of the liquid oxidation reactor permits the use of these high oxygen concentrations without forming dangerously high levels of oxygen in the overhead gas phase. The result is an increased yield and selectivity of the desired products.

Abstract: A process for the removal of catalyst poisons from hops and hop extracts is disclosed. After processing the hops to extract the alpha or beta acids therein, the alpha or beta acids are treated with activated nickel catalyst. The activated nickel catalyst binds the catalyst poisons which are believed to be sulfur containing compounds. The activated nickel and catalyst poisons are separated from the alpha or beta acids, and the alpha or beta acids are then hydrogenated and isomerized into tetrahydroisoalpha acids.

Abstract: Unsaturated organic compounds, in particular .alpha.-acids and .beta.-acids, are purified prior to hydrogenation by mixing them with an adsorbent capable of adsorbing catalyst poisons, preferably activated carbon, and separating the adsorbent containing the catalyst poisons to recover the thus purified unsaturated organic compounds. A significant reduction in the use of hydrogenation catalyst is realized.

Abstract: The present invention is a process for the production of isophorone having improved color and color stability. Crude isophorone is selectively hydrogenated to remove color forming impurities. The product isophorone will have an APHA color of about 10 or less.

Abstract: A concentrated single phase aqueous alkaline solution of tetrahydroiso-.alpha.-acids having greater than 10% to about 45% w/w tetrahydroiso-.alpha.-acids is disclosed. A method of hydrogenating and formulating a starting solution of iso-.alpha.-acids to obtain such concentrated solutions of tetrahydroiso-.alpha.-acids is also disclosed.

Abstract: Cyclohexane is catalytically oxidized to produce cyclohexanol and cyclohexanone and precursors of these products. The product is then catalytically hydrogenated while the product is still at reaction temperature to produce additional cyclohexanol and cyclohexanone from the precursors. The oxidation is carried out in a liquid oxidation reactor at high oxygen concentrations (greater than 30% and preferably greater than 90% oxygen concentration) and at relatively low temperatures (less than 160.degree. C.). The use of the liquid oxidation reactor permits the use of these high oxygen concentrations without forming dangerously high levels of oxygen in the overhead gas phase. The result is an increased yield and selectivity of the desired products. The hydrogenation is carried out in a reactor using a catalyst of palladium supported on carbon.

Abstract: Tetrahydroiso-.alpha.-acids are prepared from iso-.alpha.-acids metal salts by hydrogenating the salts in a reaction solvent of a lower alkanol containing about 5% to about 20% w/w water and in the presence of up to about 5-50 psig hydrogen and a hydrogenation catalyst at about 30.degree.-50.degree. C. to form tetrahydroiso-.alpha.-acids.

Abstract: Tetrahydro-iso-.alpha.-acids ("THIAA") are prepared directly from iso-.alpha.-acids ("IAA") by hydrogenation. Free IAA are first dissolved in ethanol. The solution is then hydrogenated in the presence of a particular type of noble metal catalyst. Hydrogenation is controlled naturally by the reaction between the catalyst and the IAA so that the IAA will be selectively converted to THIAA without unacceptable perhydrogenation into other forms.

Abstract: A process is disclosed for the removal of the 4-protected hydroxy group from compounds of the following formula: ##STR1## where A is --COOAlkyl and B is hydroxy, or A and B together represent either oxo or .dbd.CHCOOAlkyl, where X.sup.1 and X.sup.2 are the same or different and represent hydrogen or a hydroxy-protecting group, and where X.sup.3 is ##STR2## with a hydrogen radical source, such as tributyltin hydride or tris(trimethylsilyl)silane, and a radical initiator, such as AIBN or irradiation.

Abstract: Tetrahydroisohumulones are prepared from isohumulones by hydrogenating the isohumulones in a reaction solvent of ethanol containing up to about 15% water in the presence of about 1 to about 40 psig of hydrogen and a hydrogenation catalyst to form tetrahydroisohumulones.

Abstract: Cyclohexanone which has been obtained by dehydrogenation of a cyclohexanone/cyclohexanol mixture is substantially freed from by-products, in that such a dehydrogenation mixture is treated in the gas or liquid phase with hydrogen on a hydrogenation catalyst at 20.degree. to 180.degree. C. and at a pressure of 0.1 to 15 bar.

Abstract: A process for preparing a cyclopentenone by forming a two-phase mixture of a 1,4-diketone, a water immiscible organic solvent, and an aqueous base solution, and heating the mixture so as to convert the 1,4-diketone to a cyclopentenone which collects in the organic solvent phase.

Abstract: A process for producing 2-methyl-1,3-cyclohexanedione which comprises subjecting 1,3-cyclohexanedione, formaldehyde and a dialkylamine to Mannich reaction to obtain a 2-dialkylaminomethyl-1,3-cyclohexanedione, and subjecting the 2-dialkylaminomethyl to hydrogenolysis, and a process for producing 2-methylresorcinol which comprises aromatizing 2-methyl-1,3-cyclohexanedione obtained. According to these processes, it is possible to produce high-purity 2-methylresorcinol and 2-methyl-1,3-cyclohexanedione commercially easily and advantageously.

Abstract: The conjugate addition of hydrocarbon equivalents to alpha,beta-unsaturated carbonyl compounds using a series of novel catalysts is described. The catalysts comprise copper(I) complexes with ligand systems comprising either tropocoronand macrocycles or N,N'-dialkylsubstituted aminotroponeimines.

Abstract: A 3-amino-2-hydroxybornane derivative represented by formula (I): ##STR1## wherein R represents a furfuryl group, a 1-methylpyrrolylmethyl group, or a benzyl group, is disclosed. The compound is useful as a ligand in an asymmetric Michael reaction, particularly for the production of an optically active muscone.

Abstract: A process for preparing an optically active ketone represented by formula (I): ##STR1## wherein R.sup.1 represents a hydrogen atom or an alkyl group having from 1 to 5 carbon atoms; and n represents 1 or 2,which comprises asymmetrically hydrogenating an .alpha., .beta.-unsaturated ketone represented by formula (II): ##STR2## wherein R.sup.1 and n are as defined above, in the presence of a ruthenium-optically active phosphine complex as a catalyst. An optically active ketone having a high optical purity can be prepared.