The present invention primarily concerns certain 4-alkyl pyridines of the following formula (I), wherein R is C8-C12 alkyl, odiferous substance mixtures and aromatic substance mixtures containing these 4-alkyl pyridines, the respective uses thereof as an odiferous or aromatic substance (mixture) and corresponding perfumed products.

A substrate such as a fabric may be provided with a fragrance during washing or rinsing process by the addition to the wash water of a free-flowing solid fragrance-providing composition that comprises a fragrance deposited on a particulate carrier along with a water soluble salt of an alkali metal or an alkaline earth metal.

Long-lasting fragrance delivery systems and uses of the systems to provide fragrance-emitting articles with a long-lasting fragrance are disclosed herein. The long-lasting fragrance delivery systems include an emulsion of silicone-based polyurethane, fragrance, and a carrier.

(3S,5R)-3,8-dimethyl-5-(prop-1-en-2-yl)-octahydroazulen-1-ols, their use as flavor or fragrance ingredient, and a process of their production by oxidation in the presence of laccase.

The present invention relates to 1-(5-ethyl-5-methyl-1-cyclohexen-1-yl)-4-penten-1-one and its use as perfuming ingredient.

The present application relates to perfume raw materials, perfume delivery systems and consumer products comprising such perfume raw materials and/or such perfume delivery systems, as well as processes for making and using such perfume raw materials, perfume delivery systems and consumer products. Such perfume raw materials and compositions, including the delivery systems, disclosed herein expand the perfume communities' options as such perfume raw materials can provide variations on character and such compositions can provide desired odor profiles.

The present invention relates to a process for preparing cyclic compounds having at least eight carbon atoms and at least one keto group, to the cyclic compounds obtained by this process and to the use thereof, in particular as fragrance or for providing a fragrance.

A compound and a fragrance composition containing the same are provided, wherein the compound has a citrus odor in addition to a muguet odor, which is useful as a fragrance, is stable in an aqueous vehicle, and can provide a bright muguet odor with good fragrance retention by being blended with another fragrance. Particularly, they are 4(3)-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carbonitrile and a fragrance composition containing 4(3)-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carbonitrile.

The present application relates to perfume raw materials, perfume delivery systems and consumer products comprising such perfume raw materials and/or such perfume delivery systems, as well as processes for making and using such perfume raw materials, perfume delivery systems and consumer products. Such perfume raw materials and compositions, including the delivery systems, disclosed herein expand the perfume communities' options as such perfume raw materials can provide variations on character and such compositions can provide desired odor profiles.

The present invention relates to compounds of formula (I) in the form of any one of its stereoisomers or a mixture thereof, and wherein R1 represents a substituent of the benzene ring and is a bromine atom or a linear, branched or cyclic C1-8 alkyl, alkenyl, alkoxy or alkenyloxy group; R2 represents a C1-3 alkyl group; and R3 represents a hydrogen atom or a methyl or ethyl group; and their use as perfuming ingredients, for instance to impart odor notes of the watery/ozone type.

A fragrance mixture, preferably perfume oil, is described, comprising the constituents (a) (cyclopent-2-enyl ethyl acetate) and additionally (b) one or a plurality of fragrances, preferably with a floral odor note, from the group consisting of alcohols and aldehydes with a molecular weight of 210 g/mol or less and/or (c) one or a plurality of fragrances from the group consisting of ketones, ethers and esters with a molecular weight in the range from 190 g/mol through 250 g/mol.

1-(3/4-isobutyl-1/6-methylcyclohex-3-enyl)methanols and derivatives thereof having appreciable floral and hesperidic odor notes, their use as fragrance ingredient and perfumed products comprising them.

An aldehyde of formula (I) in the form of any one of its stereoisomers or a mixture thereof, wherein each dotted line, independently from each other, represents a single or double bond; n is 0 or 1; R1 is a hydrogen atom or a methyl group; R2 is a hydrogen atom or a methyl or ethyl group; and R3, which can be present in any of positions 2 to 6 of the cyclic moiety, is a hydrogen atom or a methyl or ethyl group, or a CH2 group bridging positions 3 and 6. Also, the use of the aldehyde as perfuming ingredient to impart odor notes of the aldehyde, lily of the valley type.

The deliberate release of odorants or aroma substances is desirable in many fields of application, and in particular in the field of washing and cleaning agents. Said deliberate release is achieved by using an odorant composition that comprises an odorant precursor, which is an allyl ether of the formula (I), R1R2C═CR3—CR4R5—O—CHR6R7, in which the residues R1, R2, R3, R4, R5, R6 and R7 mutually independently denote H or a hydrocarbon residue that can be acyclic or cyclic, substituted or unsubstituted, branched or unbranched, as well as saturated or unsaturated. Thus, in particular odorants in the form of an alkene having an allylic hydrogen atom, such as α-pinene, can be released in a deliberate manner.

The present invention relates to novel pyrimidine derivatives and their use in perfume compositions. The novel pyrimidine derivatives of the present invention are represented by the following formula: wherein m and n are integers of 0 or 1, with the proviso that when m is 0, n is 1 and when m is 1, n is 0; andwherein the dashed circle represents either single or double bonds.

A method for isolating 2,2,4,4-tetramethyl-1,3-cyclobutanediol (TMCD) solids from an isolated feed slurry formed in a TMCD process comprising TMCD, a liquid phase, and impurities by (a) treating the isolated feed slurry in a product isolation zone to produce an isolated TMCD product wet cake, a mother liquor, and impurities; wherein the product isolation zone can comprise at least one rotary pressure drum filter.

Crude glycerol obtained from raw materials, such as the glycerol obtained during the production of biodiesel or glycerol obtained during the conversion of fats or oils, is purified by forming a dioxolane therefrom by reacting the crude glycerol with a ketone or aldehyde, separating the dioxolane thus formed, converting the dioxolane into purified glycerol and ketone/aldehyde, and recovering the glycerol thus purified.

The present invention produces ethanol in a reactor that comprises a catalyst composition and a feed stream comprising acetic acid and a recycled liquid stream comprising ethyl acetate. The catalyst composition comprises a first catalyst comprising platinum, cobalt, and/or tin and a second catalyst comprising copper. The crude ethanol product may be separated and ethanol recovered.

The present invention is directed to processes for the recovery of ethanol from a crude ethanol product obtained from the hydrogenation of acetic acid using a low energy process. The crude ethanol product is separated in one or more columns. At least one of the columns is operated at a controlled pressure to enhance separation of ethanol and organics. In one embodiment, there are at least two columns that operate at controlled pressures.

The present invention is directed to processes for recovering ethanol obtained from the hydrogenation of acetic acid. Acetic acid is hydrogenated in the presence of a catalyst in a hydrogenation reactor to form a crude ethanol product. The crude ethanol product is separated in one or more columns to recover ethanol. In some embodiments, less than 10 wt. % ethanol is recycled to the hydrogenation reactor.

The present invention relates to catalysts and to chemical processes employing such catalysts. The catalysts are preferably used for converting acetic acid to ethanol. The catalyst comprises acidic sites and two or more metals. The catalyst has acidic sites on the surface and the balance favors Lewis acid sites.

A process for selective formation of ethanol from acetic acid by hydrogenating acetic acid in the presence of a catalyst comprises a first metal on an acidic support. The acidic support may comprise an acidic support material or may comprise an support having an acidic support modifier. The catalyst may be used alone to produced ethanol via hydrogenation or in combination with another catalyst. In addition, the crude ethanol product is separated to obtain ethanol.

A process is disclosed for producing ethanol comprising contacting acetic acid and hydrogen in a reactor in the presence of a catalyst comprising a binder and a mixed oxide comprising nickel and tin.

Disclosed herein are processes for alcohol production by reducing an esterification product, such as ethyl acetate. The processes comprise esterifying acetic acid and an alcohol such as ethanol to produce an esterification product. The esterification product may be recovered using an extractive separation. The esterification product is reduced with hydrogen in the presence of a catalyst to obtain a crude reaction mixture comprising the alcohol, in particular ethanol, which may be separated from the crude reaction mixture.

A catalyst composition for converting ethanol to higher alcohols, such as butanol, is disclosed. The catalyst composition comprises at least one alkali metal, at least a second metal and a support. The second metal is selected from the group consisting of palladium, platinum, copper, nickel, and cobalt. The support is selected from the group consisting of Al2O3, ZrO2, MgO, TiO2, zeolite, ZnO, and a mixture thereof.

A process for obtaining an industrially useful 2-chloromethylbenzaldehyde-containing liquid composition at a high yield is provided. More specifically, a process for producing 2-chloromethylbenzaldehyde comprising step (A) of mixing 1-dichloromethyl-2-chloromethylbenzene and sulfuric acid having a concentration of 84.5% by weight or more; and step (B) of mixing a mixture obtained in step (A) and water is provided.

A para-methoxy protected benzaldehyde useful in preparation of treprostinil, and of formula: (Formula (1)) is prepared by subjecting to Claisen re-arrangement a substituted benzaldehyde of formula (1a): (Formula (Ia)) to form the m-hydroxy-substituted benzaldehyde of formula (1b): (Formula (Ib)) and then reacting compound (1b) with a p-methoxybenzyl (PMB) compound to form a PMB-substituted benzaldehyde of formula (1).

The present invention relates to an apparatus for coproducting iso-type reaction product and alcohol from olefin, and a method for coproducting using the apparatus, in which the hydroformylation reactor provides a sufficient reaction area due to the broad contact surface area between the olefin and the synthesis gases that are the raw materials by a distributor plate installed in the reactor, and the raw materials can be sufficiently mixed with the reaction mixture due to the circulation of the reaction mixture so that the efficiency of the production of the aldehyde is excellent; and also the hydrogenation reactor suppresses the side reaction so that the efficiency for producing aldehyde and alcohol are all increased, and also iso-type reaction product and alcohol can be efficiently co-produced.

In a process for the dehydrogenation of cyclohexanone to produce phenol, a feed comprising cyclohexanone is contacted with a dehydrogenation catalyst under dehydrogenation conditions comprising a temperature of less than 400° C. and a pressure of less than 690 kPa, gauge, such 0.1 to 50 wt % of the cyclohexanone in said feed is converted to phenol and the dehydrogenation product contains less than 100 ppm by weight of alkylbenzenes.

Disclosed herein are processes for alcohol production by reducing ethyl acetate produced by hydrogenating acetic acid in the presence of a suitable catalyst. The product of the acetic acid hydrogenation is fed directly to a decanter to separate the hydrogenation product into an aqueous phase comprising water and ethanol and an organic phase comprising ethyl acetate. The organic phase is reduced with hydrogen in the presence of a catalyst to obtain a crude reaction mixture comprising the alcohol, in particular ethanol, which may be separated from the crude reaction mixture. Thus, ethanol may be produced from acetic acid through an ethyl acetate intermediate without an esterification step. This may reduce the recycle of ethanol in the hydrogenolysis process and improve ethanol productivity.

The present invention relates to the energy efficient and selective extraction of dilute concentrations of C2-C6 alcohols from an aqueous solution using liquid phase dimethyl ether.

A method for producing a phenylphosphonic acid metal salt composition, including reacting a phenylphosphonic acid compound (a) with a metal salt, metal oxide or metal hydroxide (b) that is present in an amount beyond the equivalent, the phenylphosphonic acid metal salt composition containing phenylphosphonic acid metal salt, and a surplus amount of the metal salt, the metal oxide or the surplus metal hydroxide (b). A crystal nucleating agent comprises the phenylphosphonic acid metal salt composition produced by the method.

Disclosed is a method for preparing a compound of Formula 1 wherein Q and Z are as defined in the disclosure comprising distilling water from a mixture comprising a compound of Formula 2, a compound of Formula 3, a base comprising at least one compound selected from the group consisting of alkaline earth metal hydroxides of Formula 4 wherein M is Ca, Sr or Ba, alkali metal carbonates of Formula 4a wherein M1 is Li, Na or K, 1,5-diazabicyclo[4.3.0]non-5-ene and 1,8-diazabicyclo[5.4.0]undec-7-ene, and an aprotic solvent capable of forming a low-boiling azeotrope with water. Also disclosed is a method for preparing a compound of Formula 2 comprising (1) forming a reaction mixture comprising a Grignard reagent derived from contacting a compound of Formula 5 wherein X is Cl, Br or I with magnesium metal or an alkylmagnesium halide in the presence of an ethereal solvent, and then (2) contacting the reaction mixture with a compound of Formula 6 wherein Y is OR11 or NR12R13, and R11, R12 and R13 are as defined in the disclosure. Further disclosed is a method for preparing a compound of Formula 7 wherein Q and Z are as defined in the disclosure, using a compound of Formula 1 characterized by preparing the compound of Formula 1 by the method disclosed above or using a compound of Formula 1 prepared by the method disclosed above.

A process for preparing isophorone (3,5,5-trimethyl-2-cyclohexen-1-one) is provided wherein distillation vapors from the work-up of product fractions are recycled to earlier stages of operation of the process.

An optically active bicyclic compound is efficiently produced by optical resolution using an optically active amine.

Disclosed are processes relating to the production of polyglycerol ethers of fatty alcohols, in particular, one step process using fatty alcohol and glycerine to synthesize polyglycerides of fatty alcohols will provide a 100% renewable surfactant that is cost effective efficient and CMR free. The synthetic methods mentioned in prior art uses hazardous chemicals as glycidyl ethers, epichlorohydrin that are listed as CMR and known carcinogens and hazardous to handle.

A polyether polyol based on renewable materials is obtained by the in situ production of a polyether from a hydroxyl group-containing vegetable oil, at least one alkylene oxide and a low molecular weight polyol having at least 2 hydroxyl groups. The polyol is produced by introducing the hydroxyl group-containing vegetable oil, a catalyst and an alkylene oxide to a reactor and initiating the alkoxylation reaction. After the alkoxylation reaction has begun but before the reaction has been 20% completed, the low molecular weight polyol having at least 2 hydroxyl groups is continuously introduced into the reactor. After the in situ made polyether polyol product having the desired molecular weight has been formed, the in situ made polyether polyol is removed from the reactor. These polyether polyols are particularly suitable for the production of flexible polyurethane foams.

The present invention relates to a method for the hydroxylation of phenols and phenol ethers by means of hydrogen peroxide. The invention specifically relates to a method for the hydroxylation of phenol by means of the hydrogen peroxide. The method of the invention for the hydroxylation of a phenol or phenol ether by means of reacting said phenol or phenol ether with the hydrogen peroxide in the presence of an acid catalyst is characterized in that it includes mixing a phenol or phenol ether with a hydrogen peroxide solution in a mixing device under conditions enabling the conversion rate of the hydrogen peroxide to be minimized, and in that said reaction mixture is then placed in a piston flow reactor where the reaction leading to the production of the hydroxylated material takes place, the acid catalyst being fed into the mixing device and/or into the piston flow reactor.

In a process for the dehydrogenation of dehydrogenatable hydrocarbons, a feed comprising dehydrogenatable hydrocarbons is contacted with a catalyst comprising a support and a dehydrogenation component under dehydrogenation conditions effective to convert at least a portion of the dehydrogenatable hydrocarbons in the feed. The catalyst is produced by a method comprising treating the support with a liquid composition comprising the dehydrogenation component or a precursor thereof and at least one organic dispersant selected from an amino alcohol and an amino acid.

Processes are disclosed for the conversion of a carbohydrate source to hexamethylenediamine (HMDA) and to intermediates useful for the production of hexamethylenediamine and other industrial chemicals. HMDA is produced by direct reduction of a furfural substrate to 1,6-hexanediol in the presence of hydrogen and a heterogeneous reduction catalyst comprising Pt or by indirect reduction of a furfural substrate to 1,6-hexanediol wherein 1,2,6-hexanetriol is produced by reduction of the furfural substrate in the presence of hydrogen and a catalyst comprising Pt and 1,2,6-hexanediol is then converted by hydrogenation in the presence of a catalyst comprising Pt to 1,6 hexanediol, each process then proceeding to the production of HMDA by known routes, such as amination of the 1,6 hexanediol. Catalysts useful for the direct and indirect production of 1,6-hexanediol are also disclosed.

The present invention relates to a process for heat integration in the preparation of saturated C3-C20-alcohols, in which a hydrogenation feed comprising at least one C3-C20-aldehyde is hydrogenated in the presence of a hydrogen-comprising gas in a hydrogenation zone and a discharge is taken off from the hydrogenation zone and subjected to distillation in at least one distillation column to give a fraction enriched in saturated C3-C20-alcohols.

A filtration method is disclosed for recovering purified polyether polyol comprising the steps of providing an aqueous solution of a polyether polyol containing an alkali metal catalyst residual formed from a transesterification process utilizing an alkali metal catalyst, contacting the aqueous solution with a stoichiometric excess of magnesium sulfate, magnesium sulfite or a combination thereof to form a second aqueous solution, wherein said stoichiometric excess is based on the amount of said alkali metal catalyst residual. Water is removed from the second aqueous solution at a temperature above a set limit of said polyether polyol to produce a dehydrated slurry containing a polyether polyol phase substantially free of residual alkali metal and a precipitated solid phase comprising sulfate and/or sulfite salts of the alkali metal catalyst, magnesium hydroxide, and excess magnesium sulfate and/or sulfite, wherein the particle size distribution of said precipitated solid phase is controlled to minimize the amount of particles therein that are smaller than 3 microns. The dehydrated slurry is then passed through a filtration system to separate the polyether polyol phase from the precipitated solid phase.

An improved method for recovering a purified polyether polyol comprising the steps of providing an aqueous solution of a polyether polyol containing an alkali metal catalyst residual formed from a transesterification process, contacting the aqueous solution with a stoichiometric excess of magnesium sulfate to form a second aqueous solution, removing water from said second aqueous solution at a temperature above the melt temperature of said polyether polyol to produce a dehydrated slurry containing a molten polyether polyol phase essentially free of residual alkali metal and a precipitated solid phase comprising sulfate and/or sulfite salts of the alkali metal catalyst, magnesium hydroxide, and excess magnesium sulfate and/or sulfide, passing the dehydrated slurry of through a filtration system comprising a filtration press to separate the molten polyether polyol phase from the precipitated solid phase, wherein the filtration press is treated with a filter aid that is essentially free of transition metal oxide content, separating the molten polyether polyol phase substantially free of water, residual alkali metal catalyst and transition metal contaminants from the precipitated solid phase and recovering polyether polyol from the separated polyether polyol phase.

A process for preparation of 2-phenyl ethanol by catalytic hydrogenation of styrene oxide using a catalyst consisting of Pd (II) on basic inorganic support is investigated. The present invention comprises development of new Pd based catalysts. The present method yields 2-phenyl ethanol in 98% selectivity at total conversion of styrene oxide. The present process represents an environment friendly alternative to conventionally used methods in industry and eliminates the reduction step for catalyst preparation. In the present invention the active catalyst is generated in situ during the hydrogenation of styrene oxide. In addition, Pd (II) supported catalysts do not catch fire (non pyrophoric), can be stored under ambient conditions and produce very less or no dust which makes said catalysts suitable for industrial application.

In one embodiment, the present application discloses methods to selectively synthesize higher alcohols and hydrocarbons useful as fuels and industrial chemicals from syngas and biomass. Ketene and ketonization chemistry along with hydrogenation reactions are used to synthesize fuels and chemicals. In another embodiment, ketene used to form fuels and chemicals may be manufactured from acetic acid which in turn can be synthesized from synthesis gas which is produced from coal, biomass, natural gas, etc.

A method of removing alkalinity and salt from a nitroaromatic product downstream of water washing to remove mineral acids and alkaline washing to remove salts of organic acids, comprises washing the product stream with an acidic aqueous solution, prior to the step of removing excess organic reactant, by steam stripping or distillation. Acid removed from the stripper or column is recycled back for use in the acidic washing. The acidic washing is done instead of the neutral washing step of the prior art. It removes residual salt and decreases the level of entrained colloidal water in the nitroaromatic product.

A system for controlling a plurality of vehicles can include at least one communications bus and a plurality of RFID detection tags that can be fixed to the communications bus equidistant from each other to define a plurality of RFID regions. Each vehicle within an RFID region can further include an RFID reader for receiving information from, and transmitting information to, the RFID tags. As the vehicle enters the RFID region for a particular RFID tag, the position of the vehicle (within the RFID region) can be communicated to the communications bus. A traffic control unit can be connected to the communications bus, and monitor can be in communication with a plurality of remotely controlled traffic control assets, such as stop signs, yield signs, traffic cones. After receiving position information on the vehicle, the monitor can selectively activate the traffic devices remotely to control vehicle traffic flow.

Disclosed is a feature for a vehicle that enables taking precautionary actions in response to conditions on the road network around or ahead of the vehicle, in particular, a blind intersection along a section of road. A database that represents the road network is used to determine locations where a blind intersection is located along a section of road. Then, precautionary action data is added to the database to indicate a location at which a precautionary action is to be taken about the blind intersection located along the section of road. A precautionary action system installed in a vehicle uses this database, or a database derived therefrom, in combination with a positioning system to determine when the vehicle is at a location that corresponds to the location of a precautionary action. When the vehicle is at such a location, a precautionary action is taken by a vehicle system as the vehicle is approaching a blind intersection.

Navigation systems and associated methods for providing navigation services are provided. Information associated with a desired route for a vehicle, such as a route between a current location and a desired destination, may be determined. Additionally, contextual information associated with the vehicle may be identified. Based upon the desired route and the contextual information, a direction may be generated for presentation to one or more users, and the generated direction may be output for presentation.

A method for illustrating an aircraft flight plan comprising at least one waypoint on a flight display of a flight deck of an aircraft, where the method may include displaying on the flight display of the flight deck some type of display indicia that indicates the suitability of locations for future waypoints.