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United States Patent Office Patented Sept 3,836,587 United States Patent Office Patented Sept. 17, 1974 2 agent. The following is a typical embodiment of generic 3,836,587 equations (A) and (B), above; ORGANO PHOSPHONIUM SALTS Martin Grayson, Norwalk, and Patricia Tarpey Keough, (n-C4H); P + BrCH, CH, OH - (n-C4H9). e CHCH.OH-Br? Ridgefield, Conn., assignors to American Cyanamid Company, Stamford, Conn. e No Drawing. Application Nov. 17, 1969, Ser. No. 871,628, (n-CH). FoH,CH-OH-Br?+ CH3COC1 - now Patent No. 3,689,601, which is a continuation of abandoned application. Ser. No. 674,107, Oct. 10, 1967, which in turn is a continuation of abandoned applica tion, Ser. No. 292,123, July 1, 1963. Divided and this 0 The trialkyl-, tricycloalkyl-, and triaryl- 2-acetoxyeth application May 22, 1972, Ser. No. 255,770 ylphosphonium salts prepared as above may, in turn, be ... nt. C. C07f 9/28 converted to their corresponding vinylphosphonium salts U.S. C. 260-606.5 F 1. Claim according to the following general equation: e 6 base 69 6 ABSTRACT OF THE DISCLOSURE 5 (C) R1R2R3PCHCHOY-X - RiR2R3P CH=CH-X in which R, R2, R3, Y and X are the same as above. Organo phosphonium salts of the formula: The following is a typical embodiment of equation (A) RR2R3PCHCHQ.exe (C), above: art. prepared by reacting compounds of the formulae: O 20 69 6 Na2CO3 69 G (E), - RR2R3PCHCHOY-X (CH)3PCHCHO CCHC1 - (CH)3P CH-CH Cl More specifically, in generic equations (A), (B) and (C), above R, R and R3 each represent alkyl C1-C1s, (II) RR2R3PCH=CH-X substituted alkyl C-C1s, cycloalkyl, and aryl; X repre with H-Q wherein: X is halogen, Y is the residue of an sents halogen, such as bromo, chloro and iodo, and tetra acylating agent, and Q is the residue of a reactant having phenyi borate; and Y in equations (B) and (C) rep an electronegative group and providing a replaceable resents the residue of an acylating agent as shown in the specific embodiments, supra. hydrogen atom (H) which is replaced by the Typical tertiary phosphine reactants are the following: RiR2R3PCHCH 30 trimethylphosphine, triethylphosphine, tripropylphos phine, tributylphosphine, tripentylphosphine, trihexyl group of compounds I or II in forming the compound A. phosphine, triheptylphosphine, trioctylphosphine, trinon - W. ylphosphine, tridecylphosphine, triundecylphosphine, tri This is a division of copending application Ser. No. dodecylphosphine, tritridecylphosphine, tritetradecylphos 871,628, filed Nov. 17, 1969 now Pat. No. 3,689,601, 35 phine, tripentadecylphosphine, trihexadecylphosphine, do which was a continuation of application Ser. No. 674,107, decyldiethylphosphine, dioctylpropylphosphine, diethyl filed Oct. 10, 1967, now abandoned, which was a con butylphosphine, butylethylhexylphosphine, tri(2-methoxy tinuation of application Ser. No. 292,123, filed July 1, pentyl)phosphine, tris-2-cyanoethylphosphine, diethyl-2- 1963, now abandoned. 40 ethoxyheptylphosphine, tricyclopropylphosphine, tricyclo The present invention relates to organophosphorus hexylphosphine, triphenylphosphine, diphenylnaphthyl compounds and to a method ef preparing same. More phosphine, trixylylphosphine, tritolylphosphine, tris(para particularly, the instant discovery concerns phosphonium ethoxyphenyl)phosphine, tris(para - chlorophenyl)phos Salt derivatives of tertiary phosphines. phine, tris(2-chlorophenyl)phosphine, tris(3-bromophen It has been found that tertiary phosphines generally 45 yl) phosphine, and the like. will react with halo-substituted ethanol to produce the Typical esterifying agents follow: lower alkanoic an corresponding trialkyl-, tricycloalkyl-, or tri-aryl- 2-hy hydrides, such as acetic anhydride, propionic anhydride, droxyethylphosphonium salts. In turn, these salts may be butanoic anhydride; lower alkanoic acids, such as formic acylated using a lower alkanoic anhydride, lower alk acid, acetic acid, propionic acid, butanoic acid; acylating anoic acid, or the like, to produce their corresponding (C2C18 alkanoyl) halides, such as acetyl chloride, propi trialkyl-, tricycloalkyl, or triaryl-2-acetoxyethylphospho 50 onyl bromide, butyryl iodide, octanoyl chloride, dodec pium-salts. anoyl bromide, stearyl chloride, hexanoyl bromide; iso : The following equations illustrate this general reaction: propenyl acetate; aryl sulfonyl halides, such as para toluenesulfonyl chloride, phenyl sulfonyl bromide, 2,4-di (A) R'R'R'P + XCH-CH-OH - 55 methylphenylsulfonyl chloride; alkyl (lower) chlorofor e e mates, such as ethylchloroformate, butylchloroformate; RR2R3PCHCHso H-x alkyl (lower) carbonates, such as diethylcarbonate, di (B) - e e esterifying propylcarbonate, dibutylcarbonate; ketene; dimethyl agent arm-9 sulfate; nitrosyl chloride; and trimethyl phosphate. :R R2R3P CHCHOH-X -- In equation (C), above, typical suitable inorganic and . 60 organic bases are: alkali metal hydroxides, such as so dium hydroxide, potassium hydroxide, lithium hydroxide; R1,R2R3 each representing, as will be seen hereinafter, alkali metal carbonates, such as sodium carbonate, potas alkyl, cycloalkyl and aryl, , sium carbonate, lithium carbonate; alkaline earth metal X representing halogen or tetraphenyl borate, and Y rep hydroxides, such as magnesium hydroxide, barium hy resenting the residue of an acylating or esterifying droxide, calcium hydroxide; alkaline. earth metal carbon 3,836,587 3 4 . ates, such as magnesium carbonate, barium carbonate, EXAMPLE calcium carbonate; activated alumina; and quaternary ammonium hydroxides, such as tetraalkyl (lower)ammo Tributyl-2-hydroxyethylphosphonium tetraphenylborate nium hydroxides, including tetramethylammonium hy droxide, tetrapropylammonium hydroxide, and tetra Tributyl - 2 - hydroxyethylphosphonium bromide, ob benzylammonium hydroxide; and basic ion exchange tained from combining tributylphosphine and 2-bromo resins. ethanol in 1,2-dimethoxyethane and refluxing under The reaction in equation (A) hereinabove is carried nitrogen, is dissolved in water and treated with excess out at a temperature in the range of 30 C. to 250 C., 0.1N sodium tetraphenylboron. The resulting precipitate preferably 60° C. to 180° C. The equation (B) reaction, 0 is filtered and recrystallized from ethanol to yield product above, is best carried out at a temperature in the range tributyl - 2 - hydroxyethylphosphonium tetraphenylborate of 5° C. to 150° C. As to equation (C), above, this re with melting point 124 C-125 C. Analysis of product action is generally carried out at a temperature in the (Found: C, 80.03; H, 9.00; P, 5.35. Cash;52O requires: range of 20° C. to 180° C., preferably 50° C. to 150 C. C, 80.55; H, 9.25; P, 5.47%.) . Each of these three reactions may be carried out at As is evident from this Example, the halide salts of atmospheric, sub-atmospheric or super-atmospheric pres Equation (A) may be converted, in situ or after recovery sure; preferably, however, reaction is carried out at atmos thereof, to the corresponding tetraphenylborate salts. ; pheric pressure. By the same token, the ratio of the reactants in each of equations (A), (B) and (C) is not EXAMPLE II critical, an excess of either reactant, in each equation, with respect to the other being suitable. In equation (B), 20 Tributyl-2-acetoxyethylphosphonium bromide however, an excess of about 10% by weight of the acylat ing agent relative to the phosphonium salt reactant is 1,2-Dimethoxyethane (275 milliliters), freshly distilled preferred. Generally in equations (A) and (C) stoichi from calcium hydride, 2-bromoethanol (133 grams, 106 ometric amounts of the reactants are employed. moles), and tributylphosphine (204 grams, 1.01 moles) The reactions of equation (A), above, are best carried are combined under nitrogen and refluxed at 85° C. over out in the presence of an inert organic solvent, i.e., a night with stirring. A heavy oil forms within an hour. solvent which does not enter into or otherwise interfere Isopropenyl acetate (320 grams, 3.2 moles) and 48% with the reaction under the conditions contemplated here HBr (3 drops) are slowly added to the reaction mixture in. Typical solvents are dimethoxyethane, dioxane, ethyl which is then refluxed 18 hours. Volatile components are acetate, tetrahydrofuran, and the like. 30 removed in vacuo at 70° C. Product (372.5 grams; 99.9% The reactions of equation (B) similarly are best carried yield) remains as a thick hygroscopic oil, which could out in the presence of an inert organic solvent of the be forced to crystallized by stirring in a benzene-petroleum type described for equation (A), as well as acetic acid, ether (boiling point 30° C.-60° C.) mixture. Crystalline dimethylformamide, diglyme, and the like. tributyl-2-acetoxyethylphosphonium salt is obtained from As to equation (C), typical suitable inert organic sol part of the oily product by freeze drying a benzene solu vents in which the phosphonium salt is solvent, which tion of the oil. - solvents do not interfere or enter into reaction to any EXAMPLE II substantial degree, are dimethoxyethane, dioxane, dimeth ylformamide, diglyme, acetonitrile, ethylacetate, tetra 40 Tributyl-2-acetoxyethylphosphonium hydrofuran, and other like linear and cyclic ethers, acetate tetraphenylborate esters (lower alkyl). Tributyl - 2 - acetoxyethylphosphonium ; bromide oil Alternatively, it has been found pursuant to the instant (16.2 grams produced as in Example II, above) is dis discovery that the products of equation (A), above, may solved in water and treated with sodium tetraphenyl be converted directly to the products of equation (C), boron (15 grams) dissolved in water. A white precipi
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