Provided is a solid acid catalyst for use in oxidation of a substrate in the coexistence of oxygen and ozone (solid acid catalyst for oxygen-ozone-coexisting oxidation). The solid acid catalyst enables oxidation of the substrate with a high conversion. This solid acid catalyst for oxygen-ozone-coexisting oxidation is a solid acid catalyst for use in an oxidation reaction to oxidize a substrate (A) in the coexistence of oxygen and ozone. The solid acid catalyst includes a transition metal in the form of an elementary substance, a compound, or an ion, and a support supporting the transition metal. The support includes, at least in its surface, a strong acid or super strong acid having a Hammett acidity function (H.sub.0) of −9 or less. The support is preferably a pellet or particle made of a fluorinated sulfonic acid resin, or a support including a solid and a layer of a fluorinated sulfonic acid resin disposed on the solid.

Provided is a method of purifying a terpenoid amino alcohol derivative, including providing a crude terpenoid amino alcohol derivative; performing an acid/base crystallization process of the crude terpenoid amino alcohol derivative to obtain an organic salt; and reacting the organic salt with NaOH and toluene to obtain a purified terpenoid amino alcohol derivative. Also provided is a method of preparing p-mentha-2,8-diene-1-ol from the purified terpenoid amino alcohol derivative.

Provided is a method of purifying a terpenoid amino alcohol derivative, including providing a crude terpenoid amino alcohol derivative; performing an acid/base crystallization process of the crude terpenoid amino alcohol derivative to obtain an organic salt; and reacting the organic salt with NaOH and toluene to obtain a purified terpenoid amino alcohol derivative. Also provided is a method of preparing p-mentha-2,8-diene-1-ol from the purified terpenoid amino alcohol derivative.

The present disclosure relates to an organometallic framework modified using a compound having a hydroxyl group (—OH), a catalyst for a hydrogenation reaction including the same, and a method of manufacturing the same. The catalyst according to the present disclosure has high activity to the hydrogenation reaction even at a low temperature of 30 to 40° C., thus making low-grade waste heat usable.

The present disclosure relates to an organometallic framework modified using a compound having a hydroxyl group (—OH), a catalyst for a hydrogenation reaction including the same, and a method of manufacturing the same. The catalyst according to the present disclosure has high activity to the hydrogenation reaction even at a low temperature of 30 to 40° C., thus making low-grade waste heat usable.

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 discloses a nickel/titanium oxide-silicon oxide catalyst for synthesizing terpinene-4-ol as well as a preparation method and method of synthesizing terpinene-4-ol using the same. The preparation method includes the steps of catalyst preparation, terpinene-4-ol synthesis and the like are disclosed in the present invention. The preparation method includes the following steps: firstly, preparing a mixed colloid of TiO.sub.2 and SiO.sub.2 by using a sol-gel method, and then centrifuging, washing, drying and roasting is performed to prepare a TiO.sub.2—SiO.sub.2 binary oxide; then, preparing Ni/TiO2-SiO2 by dipping in a nickel nitrate solution, and preparing a supported catalyst by drying and roasting; and finally, adopting a terpinolene-4, 8-epoxide a raw material, carrying out isomerization under the dual catalytic action of TiO2-SiO2 and Ni of the supported catalyst, and carrying out hydrogenation to prepare terpinene-4-ol. The preparation method can combine isomerization and hydrogenation reaction on the same catalyst, has good selectivity on terpinene-4-ol, and is simple to operate and high in product yield.

The present invention discloses a nickel/titanium oxide-silicon oxide catalyst for synthesizing terpinene-4-ol as well as a preparation method and method of synthesizing terpinene-4-ol using the same. The preparation method includes the steps of catalyst preparation, terpinene-4-ol synthesis and the like are disclosed in the present invention. The preparation method includes the following steps: firstly, preparing a mixed colloid of TiO.sub.2 and SiO.sub.2 by using a sol-gel method, and then centrifuging, washing, drying and roasting is performed to prepare a TiO.sub.2—SiO.sub.2 binary oxide; then, preparing Ni/TiO2-SiO2 by dipping in a nickel nitrate solution, and preparing a supported catalyst by drying and roasting; and finally, adopting a terpinolene-4, 8-epoxide a raw material, carrying out isomerization under the dual catalytic action of TiO2-SiO2 and Ni of the supported catalyst, and carrying out hydrogenation to prepare terpinene-4-ol. The preparation method can combine isomerization and hydrogenation reaction on the same catalyst, has good selectivity on terpinene-4-ol, and is simple to operate and high in product yield.

The invention comprises novel chiral metal complex compounds of the formula ##STR00001## wherein M, PR.sup.2, R.sup.3 and R.sup.4 are outlined in the description, its stereoisomers, in the form as a neutral complex or a complex cation with a suitable counter ion. The chiral metal complex compounds can be used in asymmetric reactions, particularly in asymmetric reductions of ketones, imines or oximes.

The invention comprises novel chiral metal complex compounds of the formula ##STR00001## wherein M, PR.sup.2, R.sup.3 and R.sup.4 are outlined in the description, its stereoisomers, in the form as a neutral complex or a complex cation with a suitable counter ion. The chiral metal complex compounds can be used in asymmetric reactions, particularly in asymmetric reductions of ketones, imines or oximes.