The present invention is directed to Cashew Nut Shell Liquid derivatives and methods for making and using same. The invention is also directed to Cashew Nut Shell Liquid based monomers and polymers for making antimicrobials, antioxidants, adhesives, coatings, corrosion retardants composites, cosmetics, detergents, soaps, de-icing products, elastomers, food, flavors, inks, lubricants, oil field chemicals, personal care products, polymers, structural polymers, engineered plastics, 3D printable polymers, techno-polymers, rubbers, sealants, solvents, surfactants and varnishes.

The present invention is directed to Cashew Nut Shell Liquid derivatives and methods for making and using same. The invention is also directed to Cashew Nut Shell Liquid based monomers and polymers for making antimicrobials, antioxidants, adhesives, coatings, corrosion retardants composites, cosmetics, detergents, soaps, de-icing products, elastomers, food, flavors, inks, lubricants, oil field chemicals, personal care products, polymers, structural polymers, engineered plastics, 3D printable polymers, techno-polymers, rubbers, sealants, solvents, surfactants and varnishes.

The present invention relates to a preparation method for and an application of a chiral spirocyclic phosphine-nitrogen-phosphine tridentate ligand SpiroPNP and an iridium catalyst Ir-SpiroPNP thereof. The chiral spirocyclic phosphine-nitrogen-phosphine tridentate ligand is a compound represented by formula I, or a racemate or optical isomer thereof, or a catalytically acceptable salt thereof, and the main structural feature is a phosphine ligand having a chiral spiro indene skeleton and a large sterically hindered substituent. The chiral spirocyclic phosphine-nitrogen-phosphine tridentate ligand can be synthesized into a chiral starting material from a 7-diaryl/alkylphosphino-7′-amino-1,1′-spirodihydroindenyl compound having a spiro ring skeleton. The iridium catalyst of the chiral spirocyclic phosphino-7′-amino-1,1′-spirodihydroindenyl compound having a sprio ring skeleton. The iridium catalyst of the chiral spirocyclic phosphine-nitrogen-phosphine tridentate ligand is a compound represented by formula II, or a racemate or optical isomer thereof, or a catalytically acceptable salt thereof. The iridium catalyst can be used to catalyze the asymmetric catalytic hydrogenation of carbonyl compounds, and especially in the asymmetric catalytic hydrogenation of simple dialkyl ketones. Said catalyst exhibits high yield (>99%) and enantioselectivity (up to 99.8% ee), thus having practical value.

##STR00001##

The present invention relates to a preparation method for and an application of a chiral spirocyclic phosphine-nitrogen-phosphine tridentate ligand SpiroPNP and an iridium catalyst Ir-SpiroPNP thereof. The chiral spirocyclic phosphine-nitrogen-phosphine tridentate ligand is a compound represented by formula I, or a racemate or optical isomer thereof, or a catalytically acceptable salt thereof, and the main structural feature is a phosphine ligand having a chiral spiro indene skeleton and a large sterically hindered substituent. The chiral spirocyclic phosphine-nitrogen-phosphine tridentate ligand can be synthesized into a chiral starting material from a 7-diaryl/alkylphosphino-7′-amino-1,1′-spirodihydroindenyl compound having a spiro ring skeleton. The iridium catalyst of the chiral spirocyclic phosphino-7′-amino-1,1′-spirodihydroindenyl compound having a sprio ring skeleton. The iridium catalyst of the chiral spirocyclic phosphine-nitrogen-phosphine tridentate ligand is a compound represented by formula II, or a racemate or optical isomer thereof, or a catalytically acceptable salt thereof. The iridium catalyst can be used to catalyze the asymmetric catalytic hydrogenation of carbonyl compounds, and especially in the asymmetric catalytic hydrogenation of simple dialkyl ketones. Said catalyst exhibits high yield (>99%) and enantioselectivity (up to 99.8% ee), thus having practical value.

##STR00001##

Processes for converting a hydrocarbon reactant into an alcohol compound and/or a carbonyl compound are disclosed in which the hydrocarbon reactant and either a supported chromium (VI) catalyst or a supported chromium (II) catalyst are contacted, optionally with UV-visible light irradiation, followed by exposure to an oxidizing atmosphere and then hydrolysis to form a reaction product containing the alcohol compound and/or the carbonyl compound. The presence of oxygen significant increases the amount of alcohol/carbonyl product formed, as well as the formation of oxygenated dimers and trimers of certain hydrocarbon reactants.

Processes for converting a hydrocarbon reactant into an alcohol compound and/or a carbonyl compound are disclosed in which the hydrocarbon reactant and either a supported chromium (VI) catalyst or a supported chromium (II) catalyst are contacted, optionally with UV-visible light irradiation, followed by exposure to an oxidizing atmosphere and then hydrolysis to form a reaction product containing the alcohol compound and/or the carbonyl compound. The presence of oxygen significant increases the amount of alcohol/carbonyl product formed, as well as the formation of oxygenated dimers and trimers of certain hydrocarbon reactants.

The present invention relates to a method for preparing p-menthane-3,8-diol, characterised in that it comprises the following steps:

a. preparation of an aqueous solution comprising between 0.05% and 5% by mass, preferably between 0.05% and 2% by mass, preferentially between 0.05% and 1% by mass, even more preferentially between 0.05% and 0.5% by mass of an ammonium salt, the said ammonium salt being characterised in that it is selected from the group formed by an amino acid ammonium salt, and in particular an amino acid hydrochloride, a vitamin B ammonium salt, and in particular a vitamin B hydrochloride, an ammonium salt of an amino acid ester, and an ammonium salt of a vitamin B ester, or is defined by the following formula (I):

##STR00001##

wherein R.sub.1 represents a benzyl, optionally substituted, or R.sub.1 represents an alkyl, either linear or branched, optionally cyclical, saturated or unsaturated, optionally substituted, comprising from 1 to 10 carbon atoms, preferably from 1 to 6 carbon atoms, preferentially from 2 to 4 carbon atoms, and R.sub.2, R.sub.3 and R.sub.4 represent a hydrogen or a methyl group, and X represents a chlorine atom, bromine atom or an OR′ group, R′ being an alkyl group comprising from 1 to 10 carbon atoms,

b. adding of citronellal to the aqueous solution obtained in the step a), and obtaining a mixture;

c. stirring and heating of the mixture obtained in the step b);

d. decanting of the reaction medium obtained at the end of step c) and obtaining at least two phases; and

e. separation of the said at least two phases obtained in the step d), and obtaining at least one aqueous phase and at least one organic phase, the said organic phase comprising at least p-menthane-3,8-diol.

The present invention relates to a method for preparing p-menthane-3,8-diol, characterised in that it comprises the following steps:

a. preparation of an aqueous solution comprising between 0.05% and 5% by mass, preferably between 0.05% and 2% by mass, preferentially between 0.05% and 1% by mass, even more preferentially between 0.05% and 0.5% by mass of an ammonium salt, the said ammonium salt being characterised in that it is selected from the group formed by an amino acid ammonium salt, and in particular an amino acid hydrochloride, a vitamin B ammonium salt, and in particular a vitamin B hydrochloride, an ammonium salt of an amino acid ester, and an ammonium salt of a vitamin B ester, or is defined by the following formula (I):

##STR00001##

wherein R.sub.1 represents a benzyl, optionally substituted, or R.sub.1 represents an alkyl, either linear or branched, optionally cyclical, saturated or unsaturated, optionally substituted, comprising from 1 to 10 carbon atoms, preferably from 1 to 6 carbon atoms, preferentially from 2 to 4 carbon atoms, and R.sub.2, R.sub.3 and R.sub.4 represent a hydrogen or a methyl group, and X represents a chlorine atom, bromine atom or an OR′ group, R′ being an alkyl group comprising from 1 to 10 carbon atoms,

b. adding of citronellal to the aqueous solution obtained in the step a), and obtaining a mixture;

c. stirring and heating of the mixture obtained in the step b);

d. decanting of the reaction medium obtained at the end of step c) and obtaining at least two phases; and

e. separation of the said at least two phases obtained in the step d), and obtaining at least one aqueous phase and at least one organic phase, the said organic phase comprising at least p-menthane-3,8-diol.

The present invention primarily concerns the use of compounds of the following formula (I)

##STR00001##

wherein X represents an oxygen atom, a —CHO, an —OH, or a —CH.sub.2OH group, a single bond or a double bond is present at the respective location of one of the dotted lines, at least one double bond is present when X is an OH group, and the 3-isopentyl or 3-isopent-2-enyl residue is connected to the ring in the ortho, meta, or para position to the X group, as perfuming and/or flavouring agents.

The invention further relates to fragrance and flavour compositions containing one or more of these compounds, perfumed or flavoured articles comprising one or more of these compounds and corresponding processes for imparting, modifying and/or enhancing certain odour notes.

The present invention primarily concerns the use of compounds of the following formula (I)

##STR00001##

wherein X represents an oxygen atom, a —CHO, an —OH, or a —CH.sub.2OH group, a single bond or a double bond is present at the respective location of one of the dotted lines, at least one double bond is present when X is an OH group, and the 3-isopentyl or 3-isopent-2-enyl residue is connected to the ring in the ortho, meta, or para position to the X group, as perfuming and/or flavouring agents.

The invention further relates to fragrance and flavour compositions containing one or more of these compounds, perfumed or flavoured articles comprising one or more of these compounds and corresponding processes for imparting, modifying and/or enhancing certain odour notes.