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United States Patent (19) 11 Patent Number: 4,488,944 Stutts Et Al

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United States Patent (19) 11 Patent Number: 4,488,944 Stutts Et Al United States Patent (19) 11 Patent Number: 4,488,944 Stutts et al. 45) Date of Patent: Dec. 18, 1984 (54) ELECTROCATALYTHC OXDATION OF FOREIGN PATENT DOCUMENTS (POLY)ALKYLENE GLYCOLS 1051614 12/1966 United Kingdom .................. 2O4/78 (75) Inventors: Kenneth J. Stutts; Karel A. J. Snoble, OTHER PUBLICATIONS both of Midland, Mich. J. Kaulen et al., Synthesis 513 (1979). (73) Assignee: The Dow Chemical Company, G. Vertes et al., Tet. 28, pp. 37-42 (1972). Midland, Mich. M. Fleishmann et al., J. Chem. Soc. Perkin II, 1396, (1972). Appl. No.: 543,199 G. Vertes et al., Acta, Chem. Acad. Sci. Hung, 67 (1971). (21) M. Fleishmann et al., J. Electroanal. Chem. 31, 39 Filed: Oct. 19, 1983 (1971). 22) P. M. Robertson, J. Electrochem. Soc., 130 (3) (1983). (51) Int. Cl. ................................................ C25B 3/02 Primary Examiner-R. L. Andrews (52) U.S. Cl. .................................... 204/79; 204/56 R Attorney, Agent, or Firm--Douglas N. Deline Field of Search ................................ 204/79, 56 R (58) (57) ABSTRACT (56) References Cited Dicarboxylic acids are prepared by oxidation of (poly U.S. PATENT DOCUMENTS )alkylene glycols with electrochemically generated nickel-oxide hydroxide. 3,725,290 4/1973 Nelson et al. ....................... 252/10 3,929,873 12/1975 Gammans ....... ... 260/531 R 3,969,200 7/1976 Nohe et al. ........................... 204/79 10 Claims, No Drawings 4,488,944 1. 2 preparation of polymers, especially polyesters that are ELECTROCATALYTIC OXEDATION OF useful molding resins. es (POLY)ALKYLENE GLYCOLS DETAILED DESCRIPTION OF THE BACKGROUND OF THE INVENTION 5 INVENTION The present invention relates to a novel process for The (poly)alkylene glycols for use in the present the preparation of dicarboxylic acids from (poly)alky invention include the well-known (poly)ethylene gly lene glycols. More particularly, the present invention cols, i.e., compounds of the formula: relates to the oxidation of (poly)alkylene glycols such as 10 HOCH2CH2O-(-CH2CH2O-)-CH2CH2OH diethylene glycol employing electrochemically gener wherein n is an integer from 0 to 10. Also included are ated nickel-oxide hydroxide, NiO(OH). (poly)propylene or (poly)butylene glycols as well as It is already known to prepare carboxylic acids by mixed glycols of ethylene oxide, propylene oxide or chemical oxidation of (poly)alkylene glycols. For exam butylene oxide. ple, in U.S. Pat. No. 3,725,290 it was taught that nitric 15 Preferred (poly)alkylene glycol reactants are (poly acid will oxidize diethylene glycol to diglycolic acid in )ethylene glycols. Most preferred is diethylene glycol high yield. Similarly in U.S. Pat. No. 3,929,873, a pro that results in the corresponding commercial chelating cess for the heterogeneous platinum catalyzed air oxida agent, diglycolic acid, tion of (poly)ethylene glycols was disclosed. Certain The oxidation is accomplished by electrochemically strong chemical oxidants are unsuited for the oxidation 20 generated nickel-oxide hydroxide, NiO(OH). Prefera of (poly)glycol ethers due to degradation of ether link bly, the nickel-oxide hydroxide is continuously regener ages or over-oxidation to the carbonate instead of the ated by electric current during the oxidation process. acid product. Several methods exist for the electrochemical genera Electrochemically prepared nickel (III) oxide hy tion of nickel-oxide hydroxide. One suitable process is droxide is already known to be suitable for the oxidation 25 Kandler deposition from a nickel salt solution. The of primary alcohols. J. Kaulen et al. in Synthesis, 513 process is described in several references including M. (1979), taught such an electrochemical oxidation of Fleischmann et al., J. Chem. Soc. Perkin II, 1396 (1972) numerous aliphatic alcohols, including furfuryl alcohol, or G. Vertes et al., Acta Chem. Acad. Sci Hung, 67 an aromatic ether, Ibid., at 514. (1971). Briefly, the nickel-oxide hydroxide is electro In GB No. 1,051,614, ethylene glycol, which contains 30 chemically formed as an active surface layer on an no ether linkages, was oxidized by use of electrochemi electrode by conversion of a previously deposited cally prepared nickel-oxide hydroxide and a nickel an nickel (II) hydroxide layer. ode. The product was glycolic acid. According to one process, an electrode is immersed G. Vertes et al., Tet. 28, 37-42 (1972), reported that in an aqueous solution of a nickel salt and charged so as no chemical difference could be detected between ac 35 to cause the precipitation of nickel (II) hydroxide onto tive nickel hydroxide prepared chemically and the ac the electrode surface. Suitable nickel salts include ni tive species formed on a nickel hydroxide electrode. trates, sulfates, etc. A preferred salt is nickel(II) nitrate. Further research by the present inventors illustrated Additional counterions such as acetate are also present. that chemically prepared NiO2H, prepared by action of Best results are obtained if the solution initially is modi hydrogen peroxide on aqueous nickel salt solutions was 40 fied by addition of hydroxide ion so as to be neutral or not suitable in oxidizing ether alcohols, especially (poly even slightly basic. Then upon application of an electric )alkylene glycols. The products formed included unac current nitrate ions are reduced to ammonia thereby ceptable amounts of formates, carbonates and other quickly forming a basic solution around the electrode over-oxidation or ether-cleavage products. leading to precipitation of nickel hydroxide. A suitable 45 aqueous solution comprises 0.1 N nickel salt, 0.1 M SUMMARY OF THE INVENTION sodium acetate and 0.005 M sodium hydroxide. Pre According to the present invention there is provided ferred electrodes are metal electrodes, especially nickel a process for preparing dicarboxylic acids correspond or platinum. The electrode to be employed as the ing to the formula: counter electrode may be iron, stainless steel, etc. 50 Multiple layers of nickel (II) hydroxide may be de HOOCCHR’O-(-CHR'CHRO-)-CHRCOOH posited, if desired, by alternately reversing the polarity wherein R' independently each occurrence is hydrogen, of the two electrodes and recharging until sufficient methyl or ethyl, and n is an integer from 0 to 10, com nickel(II) hydroxide is deposited. prising contacting a (poly)alkylene glycol correspond Once the nickel(II) hydroxide layer is prepared, it is ing to the formula: 55 converted to nickel-oxide hydroxide by contacting with hydroxide ion and applying electric potential of positive polarity. The resulting nickel-oxide hydroxide coating wherein R' and n are as previously defined, with elec may alternatively be referred to as activated nickel trochemically generated nickel-oxide hydroxide. hydroxide or nickel peroxide. Surprisingly, the electrochemically generated nickel 60 Nickel-oxide hydroxide prepared in the preceding oxide hydroxide employed in the present process does manner is stable for several minutes or even hours. not substantially over-oxidize the (poly)alkylene glycol Upon contacting the nickel-oxide hydroxide with the nor are ether linkages substantially affected by the oxi (poly)alkylene glycol, the oxidation takes place and the dation. desired dicarboxylic acid is prepared in high yields. The The dicarboxylic acid products prepared by the in 65 oxidation may take place neat, but preferably occurs in vented process are useful chelating agents for use in an aqueous electrolyte optionally containing a solvent synthetic detergent formulations. The products are also such as an alcohol to aid in solubilizing the (poly)alky usefully employed as corrosion inhibitors and in the lene glycol and an alkali metal hydroxide. By passing a 4,488,944 3 4. current through the electrolyte during the oxidation, galvanostatic cycling in the presence of both hydroxide the nickel-oxide hydroxide is continuously regenerated ion and the (poly)alkylene glycol to be oxidized. In this and serves to catalytically oxidize the (poly)alkylene manner, no pretreatment of the electrode other than glycol. cleaning in the usual manner need be performed, The above process for preparing nickel-oxide hy thereby greatly simplifying startup and preparation of droxide could be employed in a commercial process, the nickel-oxide hydroxide layer as well as regeneration however, the inconvenience of preparing electrodes of the nickel-oxide peroxide during operation. The pres prior to the oxidation by using two separate treatment ence of two nickel electrodes results in generation of steps according to the Kandler process indicates that substantially only the desired dicarboxylic acid prod commercial application would be accomplished only O ucts along with hydrogen and oxygen during the gal with difficulty. vanostatic cycling process. Accordingly, the present invented process employs As previously mentioned, the galvanostatic cycling as a preferred embodiment thereof the electrochemical process requires the use of current densities well in generation of the nickel-oxide hydroxide oxidant in situ excess of those associated with the active voltametric without use of the precipitation technique. The nickel 15 wave due to generation of nickel hydroxide. During the oxide hydroxide is prepared on a nickel anode by the cycling process, the electrode is charged into the re technique of galvanostatic cycling. By the term gal gions of oxygen and hydrogen evolution. vanostatic cycling is meant that an electrical pulse train The oxidation of (poly)alkylene oxide is accom of first one polarity then
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