A catalytic system containing a titanium zeolite of structure type MWW optionally containing zinc and containing at least one of an inorganic potassium salt and an organic potassium salt is provided. The catalyst system is useful in the preparation of propylene oxide.

Direct epoxidation of propene is carried out on electrochemically tuned mixed oxide catalyst surfaces in a single chamber reactor with mixed reaction gas of hydrocarbon and oxygen. Yield and selectivity improvement compared to platinum- or silver-based noble metal catalysts have been demonstrated for the same reactor set up. Increase in propylene oxide yield has been demonstrated when a cell voltage is applied.

In alternative embodiments the invention provides methods for synthesizing AB-007 (also called loxistatin, E64d, EST or ((2S,3S)-trans-epoxysuccinyl-L-leucyl-amido-3-methylbutane ethyl ester) and its acid form E64c (loxistatin acid), and various synthetic intermediates, and deuterated forms of these compounds, and stereoisomers thereof. In alternative embodiments the invention provides a tosylate salt of AB-007-4 or a tosylate salt of L-leucine isoamylamine, or equivalents thereof. A synthetic scheme of the invention provides kilogram quantities of AB-007 manufactured according to current good manufacturing practices (cGMP's), consistent with US FDA requirements for human use. In alternative embodiments the invention provides a tosylate salt of AB-007-4 or a tosylate salt of L-leucine isoamylamine, or equivalents thereof.

In alternative embodiments the invention provides methods for synthesizing AB-007 (also called loxistatin, E64d, EST or ((2S,3S)-trans-epoxysuccinyl-L-leucyl-amido-3-methylbutane ethyl ester) and its acid form E64c (loxistatin acid), and various synthetic intermediates, and deuterated forms of these compounds, and stereoisomers thereof. In alternative embodiments the invention provides a tosylate salt of AB-007-4 or a tosylate salt of L-leucine isoamylamine, or equivalents thereof. A synthetic scheme of the invention provides kilogram quantities of AB-007 manufactured according to current good manufacturing practices (cGMP's), consistent with US FDA requirements for human use. In alternative embodiments the invention provides a tosylate salt of AB-007-4 or a tosylate salt of L-leucine isoamylamine, or equivalents thereof.

The present invention provides a method for producing a 4,4,7-trifluoro-1,2,3,4-tetrahydro-5H-1-benzazepine compound which has an superior agonistic activity to an arginine vasopressin V2 receptor and is useful as an active ingredient for a pharmaceutical composition for preventing and/or treating urinary frequency, urinary incontinence, enuresis, central diabetes insipidus, nocturia, nocturnal enuresis, or the like; and useful intermediates for use in the methods. The production method of the present invention is suitable for the industrial production of a medicament, because of a smaller number of steps, a higher yield, and a lower cost, as compared with the methods in the related art.

A process for at least partially reactivating the catalytic activity of at least a partially deactivated catalyst following a reaction cycle, the catalyst having been used in a catalytic reaction process for hydrogenating an aromatic epoxide to produce a hydrogenated aliphatic epoxide; said process including contacting the at least partially deactivated catalyst with an oxygen-containing source at a temperature of less than about 100 C. and in the presence of a reactivation solvent for a pre-determined period of time sufficient to at least partially re-oxidize and reactivate the catalyst for further use; and a catalytic reaction process for hydrogenating an aromatic epoxide to produce a hydrogenated aliphatic epoxide including the above reactivating process step; and optionally including a step for washing the deactivated catalyst with a solvent prior to re-oxidizing the deactivated catalyst.

A process for at least partially reactivating the catalytic activity of at least a partially deactivated catalyst following a reaction cycle, the catalyst having been used in a catalytic reaction process for hydrogenating an aromatic epoxide to produce a hydrogenated aliphatic epoxide; said process including contacting the at least partially deactivated catalyst with an oxygen-containing source at a temperature of less than about 100 C. and in the presence of a reactivation solvent for a pre-determined period of time sufficient to at least partially re-oxidize and reactivate the catalyst for further use; and a catalytic reaction process for hydrogenating an aromatic epoxide to produce a hydrogenated aliphatic epoxide including the above reactivating process step; and optionally including a step for washing the deactivated catalyst with a solvent prior to re-oxidizing the deactivated catalyst.

The present invention provides a method for producing a 4,4,7-trifluoro-1,2,3,4-tetrahydro-5H-1-benzazepine compound which has an superior agonistic activity to an arginine vasopressin V2 receptor and is useful as an active ingredient for a pharmaceutical composition for preventing and/or treating urinary frequency, urinary incontinence, enuresis, central diabetes insipidus, nocturia, nocturnal enuresis, or the like; and useful intermediates for use in the methods. The production method of the present invention is suitable for the industrial production of a medicament, because of a smaller number of steps, a higher yield, and a lower cost, as compared with the methods in the related art.

The present invention provides a method for producing a 4,4,7-trifluoro-1,2,3,4-tetrahydro-5H-1-benzazepine compound which has an superior agonistic activity to an arginine vasopressin V2 receptor and is useful as an active ingredient for a pharmaceutical composition for preventing and/or treating urinary frequency, urinary incontinence, enuresis, central diabetes insipidus, nocturia, nocturnal enuresis, or the like; and useful intermediates for use in the methods. The production method of the present invention is suitable for the industrial production of a medicament, because of a smaller number of steps, a higher yield, and a lower cost, as compared with the methods in the related art.

Methods for making epoxidized fatty acid alkyl esters. Such epoxidized fatty acid alkyl esters can be prepared by epoxidizing a natural oil with an acid and a peroxide. Residual acid in the epoxidized natural oil is not neutralized, such as with a base, prior to esterification to produce the epoxidized fatty acid alkyl esters. Epoxidized fatty acid alkyl esters can be employed in plasticizers, either alone or in combination with other plasticizers, such as epoxidized natural oils. Such plasticizers in turn may be used in the formation of polymeric compositions.