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UNITED STATES PATENT OFFICE 2,683,168 PREPARATHON of ORGANO PHOSPHONY, CHELORADES Warren Jensen, Ponca City, Okla., and James O

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UNITED STATES PATENT OFFICE 2,683,168 PREPARATHON of ORGANO PHOSPHONY, CHELORADES Warren Jensen, Ponca City, Okla., and James O Patented July 6, 1954 2,683,168 UNITED STATES PATENT OFFICE 2,683,168 PREPARATHON OF ORGANO PHOSPHONY, CHELORADES Warren Jensen, Ponca City, Okla., and James O. Claytoia, Berkeley, Calif., assigno's to California, Research Corporation, San Francisco, Calif., a corporation of Delaware No Drawing. Application December 22, 1950, Serial No. 202,396 8 Claims. (CI. 260-543) 1. 2 This invention relates to a method of prepar vide a means of preparing phosphonyl compounds ing phosphonyl chlorides and the like by the wherein the phosphorus atom is directly con reaction of an organic compound with phosphorus nected to an aliphatic carbon aton. trichloride in the presence of oxygen. it is another object of this invention to provide This application is a continuation-in-part of 5 a means of converting an aliphatic carbon-to Our Copending application, Serial No. 86,856 hydrogen bond to an aliphatic carbon-to-phoS (filed April 11, 1949 which has been abandoned, phorus bond. and was a continuation-in-part of application It is a further object of this invention to pro Serial No. 716,182 (filed December 12, 1946), which wide a more economical means of obtaining or has also been abandoned). O gano phosphorus compounds having a carbon-to Phosphonyl chloride and their derivatives are phosphorus linkage. useful in various arts. For example, certain It is a still further object of this invention to phosphonyl chloride derivatives (e.g., phosphonic provide a means of obtaining organo phosphorus acids and Salts and esters thereof) are useful compounds having a carbon-to-phosphorus link as lubricating oil additives, fire retardants, and age by a method using inexpensive compounds textile treatnig agents; others are useful in the essentially hydrocarbon in structure and phOS preparation of wetting agents, emulsifying agents, phorustrichloride as reactants, which method Will plasticizers, dispersing agents; and still others proceed without the necessity of using high tem are useful as antistripping agents for asphalt peratures and expensive catalysts and will give paving compositions, asphalt pipe-coating com 20 high yields of useful carbon-to-phosphorus con positions, etc. pounds. Although these compounds are very useful, any extensive uses thereof have been impeded by the These and other objects of this invention Will be laborious and relatively expensive methods of apparent from the following description and the preparation, appended claims. 25 It has been discovered that organo phosphorus Readily usable methods are available for the compounds containing a direct carbon-to-phos preparation of phosphonyl compounds wherein phorus linkage can be prepared by reacting an the phosphorus atom is connected directly to an organic compound with phosphorus trichloride aromatic carbon atom. However, it has been difficult to prepare a phosphonyl compound in the presence of air or oxygen, said organic com Wherein the phosphorus aton is directly con pound containing at least one aliphatic carbon nected to an aliphatic carbon atonia. One meth aton, which aliphatic carbon atom is bonded only od which has been used to produce this latter car to carbon and hydrogen atons, at least one car bon-to-phosphorus linkage consists in heating the bon atom and at least One hydrogen aton, and hydrocarbon with yellow phosphorus to phos Said organic compound being free of Sulfur and phorize the hydrocarbon, followed by air-blowing 3 5 Selenium. to produce phosphonic acids. This method en The following chemical equation shows the re tails the use of high temperatures and the conse action which takes place: quent dangers of phosphorus vapors, besides being (1) g inefficient. Various methods have revolved RH -- PC3 - -2O2 --> R--0 -- HCl around the reaction of phosphorus trichloride 40 With a hydrocarbon, such methods requiring the Cl presence of aluminum chloride or acetic anhy where RH represents the organic compound, dride. These methods are also expensive and which organic compound contains at least one inefficient. aliphatic carbon atom. Heretofore, only methods comparable with the 45 A competing reaction occurs. This competing above have been available for the preparation of reaction, which is believed to supply the energy phOSphonyl compounds having a direct union be of activation for the above reaction and to be tween a carbon and a phosphorus atom. Now, the start of a chain reaction, is as follows: because of the new reaction disclosed hereinbelow, 50 (2) PC3 - -2O2 - POCl3 these phosphony compounds may be prepared on Thus, the reaction mechanism is wholly different a more extensive Scale, which should result in and from those of the processes formerly used to pre permit a more widespread use of these com pare compounds having a carbon-to-phosphorus pounds. linkage. It is a primary object of this invention to pro 55 Organic compounds which may be treated ac 2,688,168 4. 3 ether phosphonyl chloride, monochlordiethyl cording to the process of this invention to form ether phosphonyl chloride, etc. the carbon-to-phosphorus bond inciude cycloali It has been found that certain elements, When phatic hydrošarbons, such as cyclohexane, nnethyl present in the organic compound Or in the reac cyclohexane, diethyl cyclohexane, cetyl cyclohex tion mixture, inhibit the for:riation of the carbon ane, tetii'alin, etc.; aliphatic hydrocarbons, Stlch phosphorus bond according to the nethod of the as propane, butaine, isobutane, pentane, 2-rinethyl present, invention. For example, when Sulfur Or pentane, 3-in-ethyl pentaine, hexane, heptane, oc Seleniuin are present per se Or present as a part tane, isooctane, decane, tetra decane, hexadecane, of the organic compound, the reaction of the Octadecane, hydrogenated olefin polymers; and 10 present, invention does not take place. it has aromatic iny drocarbons substituted by aliphatic been noted that Sulfur and Selenium prevent the or cycloaliphatic radicals, such as toluene, xylene, oxidation of phospicius trichloride by Oxygein hexylbenzene, cetylbenzene, octaflecybenzene, according to the reaction noted in Equation 2 cyclohexyibenzene, etc. Mixtures of hydrocar herein above. Since this oxidaticia appears to ke bons inay be similairly reacted, e. g., gasoline, the first step in a chain reaction leading to the kerosene, inlineral lubricating oil fractions, and formation of a gihosphony chloride, inhibition) paraffin wax. Such Yixtures of petroleum origin of the oxidation prevents the reaction of the must be essentially free of sulfur. Also, Substi resent ii.vezation. tuted hydrocarbons, such as chlorinated hydro When ritro groups (--iNO2) are present in Cel'- carbons, eithers, esters, ketones, etc., and unsatu 20 tain conpouilds (e. g. p-initrotguene), no eac rated hydrogarhons, such as lautene-1, isobu tion takes piace betwee; the aliphatic carion tene-1, octeine-1, isooctene-1, cetene, olefin poly aton and the phosphorus trichloride in the preis mers, etc., may he reacted. Where the substituent ence of oxygen. it is believed that this is Yot Or unsaturated linkage is reactive with the phos. due to inhibition of the oxidation of phosphorus phorus trichloride or oxygen, such reaction con trichloride, but to Steric hindrance of rescia ice petes with the desired reactions leading to the effects. As is norinally true in alli reactions, it is carbon-to-phosphorus linkage, and may indeed obvious that where Steric indiances are to ?o predominate until all of the more reactive group strong, or where resonance effects are powerful, or linkage is consumed. It is, therefore, preferred to use Saturated, unsubstituted hydrocarbons, or the reaction of this invention takes place with to use unsaturated, unsubstituted hydrocarbons, difficulty, if at all. Such steric hindraces and Or to use in Saturated or substituted hydrocar resonance effects are less felt, by aliphatic car bons in which the unsaturated group or the sub bon atois which are further lernoved from the Stituent is unreactive with phosphorus trichloride arolinatic ring, 3.5 in nitro-pheny decane, for and OXygen under the conditions of reaction. example. Further exampies of organic compounds which Although phosphorus trillioride ray be used may be reacted with phosphorus trichloride and in place of phosphorus trichloride, the iatter is oxygen include ethyl chloride, ethyl fluoride, ethyl much preferred. Air, of course, is the preferred bromide, propy chloride, propyl fluoride, propyl oxidizing agent to be used in the reaction, bilt bromide, ainyl chloride, dodecyl chloride, cetyl Other forms of gaseous Cxygen, Such as pure OXY chloride, cetyl broiinide, chlorinated petroleum 4) gen and commercial oxygen, inay be used. WaX, dichloropantane, p-chlorotoluene, p-chloro The reaction may be carried out, in tha gaseous phenyl ethane, cyclohexyl chloride, diethyl ether, or liquid phase, the temperature varying frozia monochlorodiethyl ether, methyl n-butyl ether, elevated temperatures to sub-zero texperatures. isoaray benzyl ether, anisole, veratrole, phenetole, However, it is preferred to operate well below hydroquinone diethyl ether, tetrahydrofurane, cracking temperatures of the organic compotitad tetrahydrogyrane, hexamethyl sorbitol, dibutoxy reactant. The most advantageous range of ten tetra glycol, propyl butyrate, ethyl stea rate, iso perature is about -70° C. to about, --'5° C. butyl phthalate, ethyl cy-naphthyl acetate, nexy The proportions of reactants may be varied benzoate, anyl acetate, amyl laurate, diamyl considerably. As the molar ratio of phosphorus oxalate, di(2-ethylhexyl) phthalate,
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