An object of the present invention is to provide a method of purifying a phosphorus compound, which method is capable of reducing the generation of a by-product during distillation. The method of method of purifying a phosphorus compound according to the present invention includes the steps of: obtaining a mixture containing a specific phosphorus compound, a specific alkenyl phosphorus compound and a transition metal complex; and subjecting the resulting mixture to distillation after adding a Lewis acid to the mixture, to obtain a first distillate containing the specific phosphorus compound.

[Problem to be Solved] An object of the present invention is to provide a method of producing an alkenyl phosphorus compound.

[Solution to Problem] The method of producing an alkenyl phosphorus compound according to the present invention is a method of allowing a specific phosphorus compound to react with a specific alkynyl compound in the presence of a transition metal complex, a Lewis acid and a low-polarity additive, to produce a specific alkenyl phosphorus compound.

Disclosed are a trifluoromethyl alkenylphosphonate derivative and preparation method therefor. The preparation method comprises the following steps: dissolving an acetylene derivative, an iodine compound, and a phosphorus reagent in a solvent for reaction at the temperature from the room temperature to 100 C. to obtain the trifluoromethyl alkenylphosphonate derivative. In the present invention, the acetylene derivative is used as a starting material, and the raw materials are easily available and diversified; products obtained by using the method of the present invention have various types and can be directly used and also used for other further reactions; moreover, the method disclosed in the present invention has the advantages of short steps, mild reaction conditions, simple reaction operation and post-treatment processes, and high yield, and is suitable for large-scale production.

Provided is a method for producing an alkenyl phosphorus compound which can produce an alkenyl phosphorus compound efficiently even with a smaller amount of a catalyst used than that used conventionally, and further which can maintain catalytic activity to produce an alkenyl phosphorus compound in high yield even at a larger reaction scale, and which can also be applied to quantity synthesis at an industrial scale using a conventional batch reactor or continuous reactor. A method for producing an alkenyl phosphorus compound, comprising: a step of reacting a compound represented by the following formula (1): ##STR00001## [In formula (1), R.sup.1 represents OR.sup.3 or R.sup.3, R.sup.2 represents OR.sup.4 or R.sup.4, and R.sup.3 and R.sup.4 represent, for example, each independently a substituted or unsubstituted alkyl group.] with a compound represented by the following formula (2): ##STR00002## [In formula (2), R.sup.5 represents, for example, a hydrogen atom, or a substituted or unsubstituted alkyl group.] to produce the phosphorus alkenyl compound presented by at least any of the following formulas (3a) or (3b): ##STR00003## [In formulas (3a) and (3b), R.sup.1 and R.sup.2 have the same meaning as defined in formula (1), and R.sup.5 has the same meaning as defined in formula (2).], In which the compound represented by formula (1) is reacted with the compound represented by formula (2) using a transition metal catalyst, and a phosphorus oxo acid compound having an intramolecular PH bond.

Provided is a method for producing an alkenyl phosphorus compound which can produce an alkenyl phosphorus compound efficiently even with a smaller amount of a catalyst used than that used conventionally, and further which can maintain catalytic activity to produce an alkenyl phosphorus compound in high yield even at a larger reaction scale, and which can also be applied to quantity synthesis at an industrial scale using a conventional batch reactor or continuous reactor.

A method for producing an alkenyl phosphorus compound, comprising: a step of reacting a compound represented by the following formula (1):

##STR00001## [In formula (1), R.sup.1 represents OR.sup.3 or R.sup.3, R.sup.2 represents OR.sup.4 or R.sup.4, and R.sup.3 and R.sup.4 represent, for example, each independently a substituted or unsubstituted alkyl group.] with a compound represented by the following formula (2):

R.sup.5CCH(2) [In formula (2), R.sup.5 represents, for example, a hydrogen atom, or a substituted or unsubstituted alkyl group.] to produce the phosphorus alkenyl compound presented by at least any of the following formulas (3a) or (3b):

##STR00002## [In formulas (3a) and (3b), R.sup.1 and R.sup.2 have the same meaning as defined in formula (1), and R.sup.5 has the same meaning as defined in formula (2).],

In which the compound represented by formula (1) is reacted with the compound represented by formula (2) using a transition metal catalyst, and a phosphorus oxo acid compound having an intramolecular PH bond.

Disclosed is a linoleic acid derivative of Formula (I) below including a hydrophobic part C.sub.17H.sub.31 linked to a polar head part A: ##STR00001## wherein the polar head part A is selected from A.sup.1 to A.sup.4 below: ##STR00002## or a pharmaceutically/food quality acceptable salt thereof.

A flame-retardant vanillin-derived small molecule, a process for forming a flame-retardant polymer, and an article of manufacture comprising a material that contains the flame-retardant vanillin-derived small molecule are disclosed. The flame-retardant vanillin-derived small molecule can be synthesized from vanillin obtained from a bio-based source, and can have at least one phosphoryl or phosphonyl moiety with phenyl, allyl, or thioether substituents. The process for forming the flame-retardant polymer can include reacting a diol vanillin derivative and a flame-retardant phosphorus-based molecule to form the flame-retardant vanillin-derived small molecule, and binding the flame-retardant vanillin-derived small molecule to a polymer. The material in the article of manufacture can be flame-retardant, and contain the flame-retardant vanillin-derived small molecules. Examples of materials that can be in the article of manufacture can include resins, plastics, adhesives, polymers, etc.

A method of making a phosphono-phosphate compound is disclosed. The method involves a first step of mixing a first component comprising a phosphonic acid, a phosphonate or mixtures thereof, with a second component comprising a source of phosphoric acid or phosphate. The mixture has a molar phosphorous ratio of the first component to the second component of from 1:1 to 1:10. The second step involves either physically or chemically dehydrating the mixture to produce a phosphono-phosphate compound.

Disclosed are novel phosphono-phosphate compounds, monomers, and polymer compositions that have targeted uses with divalent cations and surfaces having divalent cations. These compounds can be used to deliver actives to surfaces such as calcium hydroxyapatite.

A limonene-based flame-retardant compound, a method of making a flame-retardant polymer, and an article of manufacture comprising a material that includes a limonene-based flame-retardant compound. In an embodiment, the method includes forming a limonene-based derivative; forming a phosphorus-based flame-retardant molecule; reacting the limonene-based derivative with the phosphorus-based flame-retardant molecule to form a limonene-based flame-retardant compound; and forming a flame-retardant polymer from the limonene-based flame-retardant compound. In some embodiments, the limonene-based flame-retardant compound has variable functionality including vinyl, epoxide, methylene bridges, and thioethers.