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United States Patent 0 Ice Patented Feb 1 3,642,956 United States Patent 0 ice Patented Feb. 15, 1972 1 2 reacting nonmetallic acid esters of nonmetals of Groups 3,642,956 III, IV and VI of the Mendeleeif Periodic Table or mix PROCESS FOR THE MANUFACTURE OF NEUTRAL tures of these nonmetallic acid esters, if desired in the POLYPHOSPHORIC ACID ESTERS FROM P205 presence of a solvent, at a temperature within the range AND ORTHOCARBONIC ACID ESTERS ‘ Klaus-Dieter Kampe and Edgar Fischer, both % Farb Ch of —78° C. and 140° C. with phosphorus pentoxide. werke Hoechst AG, Frankfurt am Main, Germany The term1“nonmetallic acid esters” is used herein to No Drawing. Continuation of application Ser. No. mean compounds of the elements boron, carbon, silicon 504,187, Oct. 23, 1965. This application Apr. 15, and sulfur which correspond to one of the following For 1969, Ser. No. 817,280 mulae I to IV. Claims priority, application Ggrmany, Oct. 28, 1964, 10 F Int. (:1. C07f’9/08, 7/02 US. Cl. 260-920 1 Claim (Hammett).(RH): ( R’ > .0 < OR ) .. ABSTRACT OF THE DISCLOSURE 15 A process has been provided for producing neutral poly phosphoric acid ester derivatives which comprises react ing an acid ester with phosphorus pentoxide at a tem perature within the range of —78° C. to +140° C., in 20 the absence of moisture and in a mole ratio of ester to phosphorus pentoxide from 0.02 to 3 moles ester to 1 mole phosphorus pentoxide, said acid ester being de?ned by the formula _ , (R')m-—C(0‘R)n 25 wherein m<+n=4 in which Formula R represents a satu in which R represents a saturated or unsaturated, ox rated, unsaturated, oxalkylated, or halogenated aliphatic alkylated or halogenated aliphatic radical or an aromatic radical, R’ and R” each represent a saturated or unsatu radical of l to 12 carbon atoms, or an aromatic radical of rated, oxalkylated or halogenated aliphatic or cycloaliphat 1 to 12 carbon atoms, and R’ represents a hydrogen, a saturated, unsaturated, oxalkylated, or halogenated ali ic radical or an aromatic radical. In Formula II, R’ may phatic or cycloaliphatic radical of 1 to 12 carbon atoms also represent a hydrogen atom. 1R, R’ and 1R7 may be identical or different and may each contain 1 to 12 carbon or an aromatic radical of 1 to 12 carbon atoms. The com atoms. As oxalkylated aliphatic radicals there are advan pounds are useful as catalysts for the production of poly tageously used methoxy, ethoxy, propoxy or butoxyalkyl acetals. radicals. As halogenated aliphatic radicals, mono-halo alkyl groups may be advantageously used. Furthermore, in This application is a combination of application Ser. the above Formulae I to ‘IV, j, k, l, m and n are whole num No. 504,187, ?led Oct. 23, 1965, now abandoned. bers or zero and must be such that the equations given be The present invention relates to a process for the manu low the said formulae be ful?lled, and n must be greater facture of neutral polyphosphoric acid ester derivatives. than zero in Formulae I, II and IV; in Formula III x is a It is known that neutral polyphosphoric acid esters can whole or fractional number of at least one. Fractional be obtained by reacting alkyl or aryl esters of phosphoric numbers are obtained when, in the case of polyorthosilicic acid with phosphorus pentoxide whereby oily compounds acid esters, mixtures of such esters are used for the re are formed which cannot be distilled. This process has the action. disadvantage that the unreacted proportions of the start 45 Nonmetallic acid esters suitable for use in the process ing products can be separated from the reaction product of the invention are, for example, B(OR)3, R’|B(OR)2, only with di?‘iculty at elevated temperatures. At tempera tures above 120° C., however, neutral polyphosphoric acid. R'R”BO'R, C(‘OR)4, 'HC(OR)3, Si(OR)4, R'Si(-O-R)3, esters, except methyl esters, begin to decompose. The said R’R”Si (OR ) 2, -R’3SiOR, (R0) 3Si—O—-Si—(OR ) 3, process is not, therefore, suited for the manufacture» of. 50 polyphosphoric acid esters that are free from phosphate and phosphoric or polyphosphoric acid. ‘It is furthermore OS(OR)2, and R’SO2(OR) in which R, R’ and R" have known that tetrameric cyclic polyphosphoric acid esters the meanings given above. are formed by the reaction of phosphorus pentoxide with Nonmetallic acid esters particularly suitable for use diethyl ether in chloroform. In this process, a de?nite are, for example, compounds of the formula R'R”Si(O‘R)2 mixture of two known compounds is formed; the reaction in which R, R’ and vR” represent methyl or ethyl groups, requires, however, a relatively long time, which is in or mixtures of such compounds. There may further be convenient especially for the manufacture of relatively used hexa-ethyl-di-orthosilicate and ethylpoly-orthosilicate. large amounts of these polyphosphoric acid esters. More 60 It is also possible to use trimethyl, triethyl or tripropyl over, the course of the reaction depends to a large extent esters of orthoboric acid or the corresponding esters of on the quality of the phosphorus pentoxide used. alkylboric acids in which the alkyl group contains 1 to 4 Now we have found that derivatives of polyphosphoric carbon atoms, or mixtures of such compounds for the re acid esters can be obtained in an advantageous manner by action with phosphorus pentoxide. ' p . 3,642,956, The nonmetallic acid esters are added in a pure state product and other impurities, is decanted. This procedure or in the presence of one of the solvents indicated below of dissolving and precipitation may be repeated as often at a temperature within the range of —78° C. to +140° as desired to remove undesirable impurities substantially C., advantageously —30° C. to +100° C., preferably quantitatively from the polyphosphoric acid ester deriva under an inert gas, for example nitrogen, and with as CPI tives. As precipitating agents, low molecular weight complete an exclusion of moisture as possible, to phos alkanes and cycloalkanes with S to 12 carbon atoms phorus pentoxide in a pure state or in the form of a mix which are liquid at room temperature may advantage ture thereof with one of the solvents named below. The ously be used. Examples of such compounds are hexane, reaction mixture so obtained is stirred or vigorously mixed heptane, octane and cyclohexane. Aliphatic or cyclic thoroughly at a temperature within the range indicated 10 ethers, for example, diethyl ether, tetrahydrofurane, glycol above. The reaction time depends on the reactivity of the dimethyl ether, dioxane and benzene may also be used nonmetallic acid ester and the reaction temperature and as precipitating agents. The nonmetallic acid esters are varies within a few minutes (about 3 to 10 minutes) and in general sufficiently soluble in the organic solvents used about 48 hours. The nonmetallic acid ester is advanta as precipitating agents and are highly soluble in the sol geously used in a molar ratio within the range of 0.005 vent mixtures comprising halogenated hydrocarbons and to 20 moles, advantageously the molar amounts set forth precipitating agents, which are formed in the precipitating in the table given below for each mole of phosphorus process. The precipitation of dissolved polyphosphoric pentoxide. acid ester derivatives may also be used for fractionating In the ?rst column of the table, the type of nonmetallic the products by precipitating fractions with ditferent'de acid ester used is indicated, R, R’ and R” having the grees of solubility one after the other by adding different meanings given above. The second column indicates the amounts of precipitating agent. Fractions that have been range of the molar amounts of the nonmetallic acid obtained in this manner differ from one another with esters within which the nonmetallic acid ester is reacted, respect to their catalytic activity. The polyphosphoric acid for example, with 1 mole of phosphorus pentoxide. Poly ester derivatives are obtained in the form of a colourless orthosilicic acid alkyl esters, in which the alkyl groups to slightly yellowish viscous oil which cannot be distilled may range from methyl to n-pentyl groups, are used in or in the form of an amorphous solid mass. an amount of 0.25 to 3 units of weight for each unit of The polyphosphoric acid ester derivatives constitute weight of phosphorus pentoxide. mixed anhydrides of partially hydrolyzed polyphosphoric TABLE acid esters with partially or completely hydrolyzed non 3O metallic acid esters. These mixed anhydrides contain a Type of nonmetallic Range of molar amounts of non mixture of open-chain, cyclic and combined open-chain/ acid ester: metallic acid ester/ mole P205 cyclic molecules with polyphosphate structures in which B(OR)3 __________________________ __ 0.05-3 phosphorus-oxygen-nonmetal bonds are statistically dis RIB(OR)2 _________________________ __ 0.1-5 tributed. The content of such P-O-nonmetal groupings de R'R'iBOR _________________________ _ _ 0.2-9 pends chie?y on the molar ratio in which the starting C(OR).1 __________________________ __ 0.02-2.5 products have been reacted with one another. It is, how HC(OR)3 _________________________ __ 0.05-3 ever, also in?uenced by the reaction temperature and de IR’C(=OR)3 ________________________ __ 0‘.0s_3 pends also on the individual nonmetals themselves. The Si*(OR)4 __________________________ __ 0.02—2.5 nonmetal atom in the mixed polyphosphoric acid ester (‘RO)3Si—O?'Si(OR)3 ______________ __ 0.0l-2.0 40 anhydrides may be linked to phosphorus atoms via all R’Si(OR)3 ________________________ __ 0.05-3 single-‘bond oxygen functions present in the nonmetallic tR’R”Si(OR)2 ______________________ __ 0.1-5 acid ester or via only a part of these oxygen bonds.
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