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United States Patent Office Patented Sept 3,403,186 United States Patent Office Patented Sept. 24, 1968 2 sible paths. For instance, phosphoric acid (U.S. 2,752,- 3,403,186 398) inhibits a discoloration of a phenol which is acceler STABILIZATION OF PHENOLS ated by contact with metal (steel containers, ducts, valves, Hans L. Schlichting, Grand Island, and Ellis I. Lichtblau, and so forth). But as known and illustrated later, the Kenmore, N.Y., assignors to Hooker Chemical Corpo 5 stabilization is less effective if the phenol is also exposed ration, Niagara Falls, N.Y., a corporation of New York to air and/or sunlight and/or additional trace amounts No Drawing. Filed Nov. 30, 1965, Ser. No. 510,683 of caustic or acids, such as hydrochloric acid, sulfuric 14 Claims. (CI. 260-621) acid, and so forth. Other stabilizers, for instance organic polybasic carboxylic acids (U.S. 2,672,485), or Schiff's bases (British 787,859) or amino acids (British 807,736) ABSTRACT OF THE DISCLOSURE 10 may inhibit more or less effectively a discoloration of a A mixture of a trivalent phosphorus-containing organic phenol which is promoted and accelerated by exposure to compound of the formula air and/or sunlight and/or additional trace amounts of Z. acids or alkalies. But the stabilization is less effective 5 (almost nil) if the phenol is also exposed to metal and/or P2 metal oxides, as for instance steel, iron, rust, and so Zer forth. where Z can be hydroxyl, Z and Z' can be hydrogen and It has now been found that a mixture of an aromatic Z, Z and Z' are selected from the group consisting of o-hydroxycarboxylic acid, such as salicylic acid or hy alkyl of one to twelve carbon atoms, phenyl, phenoxy, 20 droxyisophthalic acid, with a polycarboxylic acid, such substituted phenyl, substituted phenoxy, where the sub as citric acid or oxalic acid, and with an ester of a phos stituents are selected from alkyl of one to eight carbon phorus acid, such as alkyl or aryl phosphites, preferably, atoms, chloro and bromo groups, and substituted phenoxy however, where practical, a triphenyl phosphite, wherein where the substituents are selected from alkyl of one to the phenyl group corresponds with the phenol to be pro 25 tected, represents an effective stabilizer-mix preventing eight carbon atoms, chloro and bromo groups, and an a discoloration of a phenol under substantially all condi organic acid selected from an aromatic ortho-hydroxy tions that occur in commercial practice. The trivalent carboxylic acid of the formula phosphorus-containing organic compounds to be used as gooH stabilizers in this invention are selected from phosphites, 30 phosphonites, phosphinites and phosphines whose general OE formulae are: X Péo-RO-R P40-RO-R p4RutO-R p4RivRIII where X is selected from the group consisting of hydrogen, 35 alkyl of one to five carbon atoms, and carboxyl groups, Yo-Ri. Yui Ytv Yv and a saturated polycarboxylic acid containing from two Phosphite Phosphonite Phosphinite Phosphine to ten carbon atoms and from two to three carboxyl groups, each agent present being in a stabilizing propor Not included within the scope of this invention are penta tion, can be used to stabilize phenol, halophenols, alkyl 40 valent phosphorus-containing compounds, such as com phenols, and related products against deterioration in col pounds containing a (P=O) group. or and odor with age. A synergistic effect is suggested. For purposes of this invention these four formulae can be regrouped and defined by one formula This invention relates to the stabilization of phenol 45 (C6H5OH), halophenols, alkylphenols, and related prod P-Z2 ucts. More particularly, this invention relates to a method for improving the resistance of said compounds against Yn deterioration in color and odor with age and to com pounds effective as stabilizers for them. 50 where Z can be hydroxyl, Z and Z' can be hydrogen and It is well known that phenols, including halo- and alkyl Z, Z and Z' can be the same or different, alkyl of one to phenols, though carefully purified, tend to discolor on twelve carbon atoms, alkoxy of one to twelve carbon exposure to light and air. If trace impurities are present, atoms, phenyl, phenoxy, substituted phenyl where the which are often unavoidable in a commercial scale oper- . substituents are selected from alkyl of one to eight car ation, the formation of colored material is even more ac 55 bon atoms, chloro and bromo groups, and substituted celerated. This discoloration appears to stem from the phenoxy where the substituents are selected from alkyl of formation of oxidation products of the phenol. The reac one to eight carbon atoms, chloro and bromo groups. tion mechanism of this oxidation reaction is complicated, More than one such trivalent phosphorus-containing com involving radicals, ions, and ionic radicals as well. pound may be used. Numerous compounds have been claimed as effective 60 Examples of phosphite esters to be used in this invention inhibitors of deterioration of color and odor. The com are: trimethyl phosphite, triethyl phosphite, tri(2-ethyl pounds hitherto known as stabilizers for phenol may ef hexyl)phosphite, tridecyl phosphite, trilauryl phosphite, fectively inhibit one (or maybe more) reaction path(s) triphenyl phosphite, tri(o-cresyl)phosphite, tri(o-chloro in the complex oxidation reaction, but not all of the pos phenyl)phosphite, tri(bromophenyl)phosphite, diphenyl 3,403,186 3 4. decyl phosphite, phenyldidecyl phosphite, dimethyl phos of the stabilizer-mix comprising an o-hydroxycarboxylic phite ((CHO)2PHO), diethyl phosphite acid, an aliphatic polycarboxylic acid and an ester of a phosphorus-containing acid to a phenol, preferably im mediately after the phenol has been distilled, is highly dibutyl phosphite ((CHO)2PHO), di(2-ethylhexyl)- effective in inhibiting a change in color of the phenol, phosphite ((CaHO)2PHO), dilauryl phosphite even under extreme storage conditions, such as being held in a molten state and in steel containers contaminated with caustic, scale and rust; or being held in a molten phenyl neopentyl phosphite, nonylphenyl neopentyl phos state exposed to the daily sunlight in glass containers con phite, diphenyl phosphite ((C6H5O)2PHO), di(o-cresyl)- taminated with caustic, scale and rust. phosphite, di(chlorophenyl)phosphite, di(bromophenyl)- 0 Each agent is present in a stabilizing amount. The phosphite, diphenyl decyl phosphite, and the like. amount of the stabilizer-mix employed corresponds to be Examples of phosphonites to be used in this invention tween about 0.001 percent and about 0.5 percent, pref are: dimethyl methylphosphonite, diethyl methylphos erably between about 0.002 percent and about 0.02 per phonite, di(n-butyl)-hydrogen phosphonite, diphenyl 5 cent by weight of the phenol. In any event, the total phenylphosphonite, di(o-cresyl)- o-cresylphosphonite, stabilizer-mix is present in a stabilizing proportion. di(o- chlorophenyl)o - chlorophenylphosphonite, diamyl It has surprisingly been found that the incorporation amylphosphonite, dibenzyl methylphosphonite, and the with a phenol of a stabilizing amount of (a) triphenyl like. phosphite, (b) salicylic or hydroxyisophthalic acid, and Examples of phosphinites to be used in this invention 20 (c) citric or oxalic acid, inhibits most effectively color are: methyl dimethylphosphinite, ethyl diethylphosphinite, development than the incorporation of any one of the methyl di(n-butyl) phosphinite, phenyl diphenylphosphi components alone. The components may normally be nite, o-cresyl di(o-cresyl) phosphinite, o-chlorophenyl di(o- mixed in equal amounts by weight. However, different chlorophenyl)phosphinite, benzyl dimethylphosphinite, ratios may also be used for economical reasons or be and the like. 25 cause a certain ratio of trace impurities or other pro Examples of phosphines to be used in this invention are: moters of color are expected in the phenol. For instance, tri(n-butyl)phosphine, diphenyl phosphine, triphenyl phos the ratio of component (a) (triphenyl phosphite) may phine, di(o-cresyl)phosphine, tri(o-cresyl)phosphine, di be increased in case of extended exposure to iron surfaces. (o- chlorophenyl) - phosphine, tri(o-chlorophenyl) phos If these iron surfaces are heavily corroded with rust, Scale phine, dicyclohexyl phosphine, and the like. 30 and various metal oxides thus likely to be present, the The trivalent phosphorus-containing organic compound ratio of component (c) (citric or oxalic acid) may be can be used in admixture with other agents to stabilize advantageously increased. If extended exposure to Sun the phenol. Especially preferred among these is an organic light is expected, component (b) (salicylic or hydroxyiso acid component to be used in the stabilizer-mix, selected phthalic acid) may be mixed in a higher ratio. from aromatic ortho-hydroxy-carboxylic acids and satu 35 Chelating agents not effective in preventing a discolor rated aliphatic polycarboxylic acids. The aromatic ortho ation as such, may effectively supplement the claimed hydroxycarboxylic acids to be used as stabilizers are of stabilizer-mix as defined in this invention in case of ex the formula: treme corrosion. These commonly known effects of che lating agents to dissolve and/or to inactivate harmful sus gooH 40 pension of metals and metal oxides may be additionally OH supplied to supplement the effectiveness of the claimed X stabilizer-mix. A chelating agent, however, cannot re place either one of the component agents without a drastic reduction of the color inhibitor effects. Suitable chelating where X is selected from hydrogen, alkyl of one to five 45 agents are, for instance, ethylenediamine-N,N,N',N'- carbon atoms, and carboxyl groups. Illustrative of these tetraacetic acid, or preferably because of a more favorable compounds are salicylic acid, 4-methylsalicylic acid, 4 solubility 1,2-diaminocyclohexane-N,N,N',N'-tetraacetic tertiary butylsalicylic acid, hydroxyterephthalic acid, and acid. 4-hydroxyisophthalic acid; however, other acids within Phenols to be stabilized by the method of this invention the defined formula may also be used.
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