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Unreleak Se A 3,409,707 United States Patent Office Patented Nov. 5, 1968 1. 2 The following is a typical embodiment of equation 3,409,707 (C), above: DI THO PHOSPHORUS PHOSPHONIUMSALTS Martin Grayson, Norwalk, Patricia Tarpey Keough, Ridge 69 g 6 Na2CO3 e) 6 field, and Michael McKay Rauhut, Norwalk, Conn, as (CH3)3P CHCH, OCCH.Cl -> (CH3)3P CH=CH-Cl signors to American Cyanamid Company, Stamford, More specifically, in generic Equations A, B and C, Conn., a corporation of Maine No Drawing. Application Feb. 12, 1964, Ser. No. 344,224, above, R, R2 and R3 each represent alkyl C1-C1s, sub now Patent No. 3,299,143, dated Jan. 17, 1967, which stituted alkyl C1-C1, cycloalkyl, and aryl; X represents is a continuation of application Ser. No. 256,124, Feb. 4, halogen, such as bromo, chloro and iodo, and tetraphenyl 1963. Divided and this application Oct. 30, 1964, Ser. borate; and Y in Equations B and C represents the res No. 407,873 0 idue of an acylating agent as shown in the specific em 4 Claims. (C. 260-931) bodiments, supra. Typical tertiary phosphine reactants are the following: trimethylphosphine, tirethylphosphine, tripropylphos phine, tributylphosphine, tripentylphosphine, trihexyl ABSTRACT OF THE DISCLOSURE 5 phosphine, triheptylphosphine, trioctylphosphine, tri Phosphonium salt derivatives of the formula onylphosphine, tridecylphosphine, triundecylphosphine, S A tridodecylphosphine, tritridecylphosphine, tritetradecyl phosphine, tripentadecylphosphine, trihexadecylphos phine, dodecyldiethylphosphine, dioctylpropylphosphine, unreleakA. se 20 diethylbutylphosphine, butylethylhexylphosphine, tri(2- wherein R, R2, R, A, A and X are as hereinafter de methoxypentyl) phosphine, tris - 2 - cyanoethylphos fined. The compounds are useful as fire retardants in phine, diethyl - 2 - ethoxyheptylphosphine, tricyclo plastics. propylphosphine, tricyclohexylphosphine, triphenylphos phine, diphenylnaphthylphosphine, trixylylphosphine, tri 25 tolylphosphine, tris(para - ethoxyphenyl)phosphine, tris The instant application is a division of U.S. applica (para - chlorophenyl)phosphine, tris(2 - chlorophenyl) tion Ser. No. 344,224, filled Feb. 12, 1964, now U.S. phosphine, tris(3 - bromophenyl)phosphine, and the like. Patent 3,299,143, issued Jan. 17, 1967, which in turn was Typical esterifying agents follow: lower alkanoic a continuation of U.S. application Ser. No. 256,124 filed 30 anhydrides, such as acetic anhydride, propionic anhy Feb. 4, 1963, now abandoned. dride, butanoic anhydride; lower alkanoic acids, such as The present invention relates to organophosphorus com formic acid, acetic acid, propionic acid, butanoic acid; pounds and to a method of preparing same. More par acylating (C-C8 alkanoyl) halides, such as acetyl ticularly, the instant discovery concerns phosphonium chloride, propionyl bromide, butyryl iodide, octanoyl salt derivatives of tertiary phosphines. chloride, dodecanoyl bromide, stearyl chloride, hexanoyl It has been found that tertiary phosphines generally bromide; isopropenyl acetate; aryl sulfonyl halides, such will react with halo-substituted ethanol to produce the as para - toluenesulfonyl chloride, phenyl sulfonyl bro corresponding trialkyl-, tricycloalkyl-, or tri-aryl-2-hy mide, 2,4 - dimethylphenylsulfonyl chloride; alkyl droxyethylphosphonium salts. In turn, these salts may be (lower) chloroformates, such as ethylchloroformate, acylated using a lower alkanoic anhydride, lower 40 butylchloroformate; alkyl (lower) carbonates, such as alkanoic acid, or the like, to produce their correspond diethylcarbonate, dipropylcarbonate, dibutylcarbonate; ing trialkyl-, tricycloalkyl, or triary1 - 2 - acetoxyethyl ketene; dimethyl sulfate; nitrosyl chloride; and trimethyl phosphonium salts. phosphate. The following equations illustrate this general reac In Equation C, above, typical suitable inorganic and organic bases are: alkali metal hydroxides, such as so tion: 45 dium hydroxide, potassium hydroxide, lithium hydroxide; (A) RR2R3P -- XCHCH-OH - RRR-FCHCH,0Hs€9 alkali metal carbonates, such as sodium carbonate, potas sium carbonate, lithium carbonate; alkaline earth metal (B) esterifying agent hydroxides, such as magnesium hydroxide, barium hy R1,R2R3P CHCHOH.X -- - - - --> 50 droxide, calcium hydroxide; alkaline earth metal carbon ates, such as magnesium carbonate, barium carbonate, calcium carbonate; activated alumina; and quaternary am R, R2, R3 each representing, as will be seen hereinafter, monium hydroxides, such as tetraalkyl (lower) ammo alkyl, cycloalkyl and aryl, nium hydroxides, including tetramethylammonium hy X representing halogen or tetraphenyl borate, and Y rep droxide, tetrapropylammonium hydroxide, and tetraben resenting the residue of an acylating or esterifying 55 Zylammonium hydroxide; and basic ion exchange resins. agent. The following is a typical embodiment of generic The reaction in Equation A hereinabove is carried out Equations A and B, above: at a temperature in the range of 30° C. to 250° C., pref erably 60° C. to 180° C. The Equation Breaction. above, 60 is best carried out at a temperature in the range of 5 C. to 150 C. As to Equation C, above, this reaction is gen erally carried out at a temperature in the range of 20° C. O to 180° C., preferably 50° C. to 150° C. Each of these three reactions may be carried out at 65 atmospheric, sub-atmospheric or super-atmospheric pres The trialkyl-, tricycloalkyl-, and triary1 - 2 - acetoxy Sure; preferably, however, reaction is carried out at atmos ethylphosphonium salts prepared as above may, in turn, pheric pressure. By the same token, the ratio of the re be converted to their corresponding vinylphosphonium actants in each of Equations A, B and C is not critical, an salts according to the following general equation: excess of either reactant, in each equation, with respect (C) 6 G base €E) 6 70 R1R2R3P CHCHOY,X - R1R2R3P CH-scCHX Typical are:polymeric quarternary ammonium salts, e.g., in which R, R2, R3, Y and X are the same as above. polymeric trimethylbenzyl ammonium chloride, etc. 3 3,409,707 4. to the other being suitable. In Equation B, however, an moles), and tributylphosphine (204 grams, 1.01 moles) excess of about 10% by weight of the acylating agent rela are combined under nitrogen and refluxed at 85 C. tive to the phosphonium salt reactant is preferred. Gen overnight with stirring. A heavy oil forms within an hour. erally in Equations A and C stoichiometric amounts of Isopropenyl acetate (320 grams, 3.2 moles) and 48% the reactants are employed. 5 HBr (3 drops) are slowly added to the reaction mixture The reactions of Equation A, above, are best carried which is then refluxed 18 hours. Volatile components out in the presence of an inert organic solvent, i.e., a are removed in vacuo at 70° C. Product (372.5 grams; solvent which does not enter into or otherwise interfere 99.9% yield) remains as a thick hygroscopic oil, which with the reaction under the conditions contemplated here could be forced to crystallize by stirring in a benzene in. Typical solvents are dimethoxyethane, dioxane, ethyl petroleum ether. (boiling point 30° C.-60 C.) mixture. acetate, tetrahydrofuran, and the like. 10 Crystalline tributyl-2-acetoxyethylphosphonium salt is The reactions of Equation B similarly are best carried obtained from part of the oily product by freeze drying out in the presence of an inert organic solvent of the type a benzene solution of the oil. described for Equation A, as well as acetic acid, dimethyl Example III-Tributyl-2-acetoxyethylphosphonium formamide, diglyme, and the like. " tetraphenylborate As to Equation C, typical suitable inert organic Solvents in which the phosphonium salt is solvent, which solvents Tributyl-2-acetoxyethylphosphonium bromide oil (16.2 do not interfere or enter into reaction to any substantial grams produced as in Example II, above) is dissolved degree, are dimethoxyethane, dioxane, dimethylformam in water and treated with sodium tetraphenylboror ide, diglyme, acetonitrile, ethylacetate, tetrahydrofuran, 20 (15 grams) dissolved in water. A white precipitate ap and other like linear and cyclic ethers, acetate esters pears which is filtered and recrystallized from ethanol (lower alkyl). containing enough acetonitrile to cause solution at the Alternatively, it has been found pursuant to the instant boiling point of the mixture. Tributyl-2-acetoxyethyl discovery that the products of Equation A, above, may phosphonium tetraphenylborate (16.7 grams) is obtained be converted directly to the products of Equation C, 25 with melting point of 177 C-179 C. Analysis of prod thusly, D uct (Found: C, 76.65; H, 8.83; P, 5.24. C40H5O2BP requires: C, 78.93; H, 8.94; P, 5.10%.) Example IV.- Triphenyl-2-acetoxyethylphosphonium iodide in the presence of any base given above for Equation C 30 and at a temperature in the range of 100 C. to 250 C. 2-iodoethylacetate is prepared from the nucleophilic As in Equation C, a solvent of the type given hereinabove exchange reaction of sodium iodide and 2-chloroethyl for Equation C is suitable and herein contemplated. If acetate in refluxing acetone under nitrogen (boiling point desired, the reaction may be carried out in the presence 86° C.-90° C. at 33 milliliters mercury). Triphenyl of a dehydrating agent, such as a siliceous agent includ 35 phosphine (7.35 grams) is reacted with 2-iodoethyl ing silica (e.g. silica gel), silica-alumina, and the like, in acetate (24 grams) under nitrogen with stirring at 80 which other inert organic solvents are also suitable, e.g. C. for 4.5 hours. The excess 2-iodoethylacetate
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