Disclosed herein are methods for synthesizing fatty olefin metathesis products of high Z-isomeric purity from olefin feedstocks of low Z-isomeric purity. The methods include contacting a contacting an olefin metathesis reaction partner, such as acylated alkenol or an alkenal acetal, with an internal olefin in the presence of a Z-selective metathesis catalyst to form the fatty olefin metathesis product. In various embodiments, the fatty olefin metathesis products are insect pheromones. Pheromone compositions and methods of using them are also described.

Disclosed herein are methods for synthesizing fatty olefin metathesis products of high Z-isomeric purity from olefin feedstocks of low Z-isomeric purity. The methods include contacting a contacting an olefin metathesis reaction partner, such as acylated alkenol or an alkenal acetal, with an internal olefin in the presence of a Z-selective metathesis catalyst to form the fatty olefin metathesis product. In various embodiments, the fatty olefin metathesis products are insect pheromones. Pheromone compositions and methods of using them are also described.

A process for making sorbic acid from renewable materials is provided. The process comprises converting acetic acid to ketene; converting acetaldehyde to crotonaldehyde; reacting the ketene with the crotonaldehyde to produce a polyester; and converting the polyester to sorbic acid. Renewable materials are incorporated by one of the following methods: a) the acetic acid is produced by reacting methanol derived from renewable organic material with carbon monoxide, b) the acetic acid is a biobased acetic acid, c) the crotonaldehyde is a biobased crotonaldehyde, d) the crotonaldehyde is produced by converting a biobased acetaldehyde to crotonaldehyde, e) the crotonaldehyde is produced by converting acetaldehyde to crotonaldehyde and the acetaldehyde is produced from bioethylene, or any combination of a), b), c), d) and e).

A process for making sorbic acid from renewable materials is provided. The process comprises converting acetic acid to ketene; converting acetaldehyde to crotonaldehyde; reacting the ketene with the crotonaldehyde to produce a polyester; and converting the polyester to sorbic acid. Renewable materials are incorporated by one of the following methods: a) the acetic acid is produced by reacting methanol derived from renewable organic material with carbon monoxide, b) the acetic acid is a biobased acetic acid, c) the crotonaldehyde is a biobased crotonaldehyde, d) the crotonaldehyde is produced by converting a biobased acetaldehyde to crotonaldehyde, e) the crotonaldehyde is produced by converting acetaldehyde to crotonaldehyde and the acetaldehyde is produced from bioethylene, or any combination of a), b), c), d) and e).

The present invention relates to a process for preparing a (4Z)-11,11-dialkoxy-4-undecenyltriarylphosphonium halide compound of the following general formula (3-Z): wherein Y represents a halogen atom, Ar represents, independently of each other, an aryl group, and R.sup.1 and R.sup.2 represent, independently of each other, a monovalent hydrocarbon group having 1 to 15 carbon atoms, or R.sup.1 and R.sup.2 may form together a divalent hydrocarbon group, R.sup.1-R.sup.2, having 2 to 10 carbon atoms, the process comprising: subjecting a (7Z)-11-halo-1,1-dialkoxy-7-undecene compound of the following general formula (1-Z): wherein X.sup.1 represents a halogen atom, and R.sup.1 and R.sup.2 are as defined above to a phosphonium salt formation reaction with a phosphine compound of the following general formula (2): wherein Ar is as defined above to form the (4Z)-11,11-dialkoxy-4-undecenyltriarylphosphonium halide compound (3-Z).

##STR00001##

The present invention also relates to a compound of the following general formula (A): L(CH.sub.2).sub.3CH═CH(CH.sub.2).sub.5CH(OR.sup.1)(OR.sup.2) (A) wherein R.sup.1 and R.sup.2 are as defined above.

The present invention relates to a process for preparing a (4Z)-11,11-dialkoxy-4-undecenyltriarylphosphonium halide compound of the following general formula (3-Z): wherein Y represents a halogen atom, Ar represents, independently of each other, an aryl group, and R.sup.1 and R.sup.2 represent, independently of each other, a monovalent hydrocarbon group having 1 to 15 carbon atoms, or R.sup.1 and R.sup.2 may form together a divalent hydrocarbon group, R.sup.1-R.sup.2, having 2 to 10 carbon atoms, the process comprising: subjecting a (7Z)-11-halo-1,1-dialkoxy-7-undecene compound of the following general formula (1-Z): wherein X.sup.1 represents a halogen atom, and R.sup.1 and R.sup.2 are as defined above to a phosphonium salt formation reaction with a phosphine compound of the following general formula (2): wherein Ar is as defined above to form the (4Z)-11,11-dialkoxy-4-undecenyltriarylphosphonium halide compound (3-Z).

##STR00001##

The present invention also relates to a compound of the following general formula (A): L(CH.sub.2).sub.3CH═CH(CH.sub.2).sub.5CH(OR.sup.1)(OR.sup.2) (A) wherein R.sup.1 and R.sup.2 are as defined above.

Provided herein novel processes for preparing carotenoids, substantially pure carotenoids (such as substantially pure trans crocetin diesters and substantially pure trans sodium crocetinate), pharmaceutical compositions, and related methods of treatment and uses. The provided compositions have uses in treating diseases, disorders and conditions associated with, but not limited to, infection, ARDS, endotoxemia, inflammation, sepsis, ischemia, hypoxia, shock, stroke, lung injury, wound healing, traumatic injury, reperfusion injury, cardiovascular disease, kidney disease, liver disease, inflammatory disease, metabolic disease, pulmonary disorders, blood related disorders and hyperproliferative diseases such as cancer. Methods of making, and using the aqueous solutions and pharmaceutical compositions are also provided.

Provided herein novel processes for preparing carotenoids, substantially pure carotenoids (such as substantially pure trans crocetin diesters and substantially pure trans sodium crocetinate), pharmaceutical compositions, and related methods of treatment and uses. The provided compositions have uses in treating diseases, disorders and conditions associated with, but not limited to, infection, ARDS, endotoxemia, inflammation, sepsis, ischemia, hypoxia, shock, stroke, lung injury, wound healing, traumatic injury, reperfusion injury, cardiovascular disease, kidney disease, liver disease, inflammatory disease, metabolic disease, pulmonary disorders, blood related disorders and hyperproliferative diseases such as cancer. Methods of making, and using the aqueous solutions and pharmaceutical compositions are also provided.

Provided are a method for efficiently producing an asymmetric conjugated diyne from an inexpensive and safe alternative compound to hydroxylamine hydrochloride and a method for producing a Z,Z-conjugated diene compound from the asymmetric conjugated diyne compound thus obtained. More specifically, provided is a method for producing an asymmetric conjugated diyne compound comprising a step of subjecting a terminal alkyne compound (1): HC≡C—Z.sup.1—Y.sup.1 to a coupling reaction with an alkynyl halide (2): Y.sup.2—Z.sup.2—C≡C—X by using sodium borohydride in water and an organic solvent in the presence of a copper catalyst and a base to obtain the asymmetric conjugated diyne compound (3): Y.sup.2—Z.sup.2—C≡C—C≡C—Z.sup.1—Y.sup.1. In addition, provided is a method for producing a Z,Z-conjugated diene compound by reducing the resulting asymmetric conjugated diyne compound, or the like.

Provided are a method for efficiently producing an asymmetric conjugated diyne from an inexpensive and safe alternative compound to hydroxylamine hydrochloride and a method for producing a Z,Z-conjugated diene compound from the asymmetric conjugated diyne compound thus obtained. More specifically, provided is a method for producing an asymmetric conjugated diyne compound comprising a step of subjecting a terminal alkyne compound (1): HC≡C—Z.sup.1—Y.sup.1 to a coupling reaction with an alkynyl halide (2): Y.sup.2—Z.sup.2—C≡C—X by using sodium borohydride in water and an organic solvent in the presence of a copper catalyst and a base to obtain the asymmetric conjugated diyne compound (3): Y.sup.2—Z.sup.2—C≡C—C≡C—Z.sup.1—Y.sup.1. In addition, provided is a method for producing a Z,Z-conjugated diene compound by reducing the resulting asymmetric conjugated diyne compound, or the like.