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United States Patent (19) 11 Patent Number: 5,449,387 Hawkins Et Al

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United States Patent (19) 11 Patent Number: 5,449,387 Hawkins Et Al USOO5449387A United States Patent (19) 11 Patent Number: 5,449,387 Hawkins et al. 45 Date of Patent: Sep. 12, 1995 54 CERIUM (IV) CATALYST COMPOUNDS 4,264,335 4/1981 Bello et al. AND PROMOTING COMBUSTION OF 4,545,923 10/1985 Gradeff et al. ...................... 252/309 HYDROCARBON FUELS THEREWTH 4,599,201 8/1986 Gradeff et al. 4,886,624 12/1989 Gradeff et al. ....................... 534/15 75 Inventors: Ian M. Hawkins, Lancashire, United 4,920,204 4/1990 Gradeff et al. ... ... 534/15 Kingdom; Heiko H. K. Mauermann, 5,002,747 3/1991 Le Loarer ......... ... 42.3/592 Plainsboro, N.J. 5,023,070 6/1991 Le Loarer ........................... 423/592 5,132,048 7/1992 Picard-Seon et al. ........... 252/313.1 73 Assignee: Rhone-Poulenc Chemicals Limited, 5,145,605 9/1992 Chane-Ching . Hertfordshire, United Kingdom 5,279,789 1/1994 Le Loarer et al. ................ 423/21.1 21 Appl. No.: 184,197 FOREIGN PATENT DOCUMENTS 22 Filed: Jan. 18, 1994 0433133 6/1991 European Pat. Off. 1475971 6/1977 United Kingdom . Related U.S. Application Data Primary Examiner-Prince Willis, Jr. (63. Continuation-in-part of Ser. No. 77,362, Jun. 17, 1993, Assistant Examiner-Alan D. Diamond abandoned. Attorney, Agent, or Firm-Burns, Doane, Swecker & 30 Foreign Application Priority Data Mathis Jun. 17, 1992 GB United Kingdom ................. 9212811 57 ABSTRACT Sep. 23, 1992 GB United Kingdom ................. 922O16 Novel cerium (IV) oxidic compounds, well suited as Jun. 17, 1993 AU) Australia .............................. 934.1332 catalysts, e.g., for the clean combustion of hydrocarbon Jun. 17, 1993 BR) Brazil ................................... 9302397 fuels and for the "drying' of paint compositions, each Jun. 17, 1993 (CA) Canada ................................. 2098666 Ce(IV) atom of which being coordinated with two Jun. 17, 1993 CN China .............................. 93.108921.2 anions of an organic oxyacid advantageously having a Jun. 17, 1993 (EP) European Pat. Off. ... 93304760 pKa greater than 1, preferably greater than 2, or a mix Jun. 17, 1993 HU Hungary .............................. 930.1765 ture of such oxyacids, and the oxidic oxygen atom or Jun. 17, 1993 JP Japan .................. ... S-146035 atoms of which being other than those comprising the Jun. 17, 1993 (KR) Rep. of Korea ..................... 93.11.21 organic oxyacids; representative such novel cerium Jun. 17, 1993 MX Mexico ........... ... 933631 (IV) oxidic compounds, whether yellow crystalline Jun. 17, 1993 NO Norway ................................. 932232 solids or yellow liquids, have the formula: 51) Int. Cl. ......................... C10L 1/12; C01F 17/00 52 U.S. Cl. ........................................ 44/364; 44/354; 44/358; 534/16; 554/72; 556/1 58) Field of Search ................. 44/364, 355, 356, 354, 44/357,358; 534/15, 16; 554/72; 556/1; in which the radicals A, which may be the same or 562/600; 252/313.1; 106/1.05, 14.36, 27 B:28 different, are each the residue of an organic oxyacid of A, 30 C formula AH, p is an integer ranging from 0 to 5, n ranges from 0 to 2 and m is an integer ranging from 1 to 56) References Cited 12. U.S. PATENT DOCUMENTS 3,231,592 1/1966 McCord . 28 Claims, 7 Drawing Sheets U.S. Patent Sep. 12, 1995 Sheet 1 of 7 5,449,387 0037 (9) 008 00Z? (€) 838|W[INBAVNA 000Z00,72008Z,00ZE0098 (L) 00|| 08 09 000*7 0Z?Ilfil-' 3DNWLWSNWRL / U.S. Patent Sep. 12, 1995 Sheet 2 of 7 5,449,387 0037 (9) 009 00ZI. 000Z 00372 008Z B|W0IJO(AI)HD (1) 08 09 OZ 000*/ OZI.'Z51-y 3ONWWSNW. M. U.S. Patent Sep. 12, 1995 Sheet 3 of 7 5,449,387 00,7 (G) 008 00ZI, (€) 000Z 839VNT'NBWM (!) 0000*) 00|| 08 09 OZ 3DNWLWSNWR / U.S. 5,449,387 09%9:2900|| DLOR WERSION Oil BM RAMANOR HC2S U.S. Patent Sep. 12, 1995 Sheet 5 of 7 5,449,387 RPR/CRA/P-An/LABORATORE RAMAN 93 HRD 024 46. R93 ##9 Z$$| 12# 09%939001 #98 668 918 Q6/-/ DLOR WERSON 0 IBM RAMANOR HC2S U.S. Patent Sep. 12, 1995 Sheet 6 of 7 5,449,387 2192 G19 00; (UUU)JINIT(110X3 (MUU)’MOd}}}SWT W083W/TH103dS DOR WERSON 0 IBM RAMANOR HG2S U.S. Patent Sep. 12, 1995 Sheet 7 of 7 5,449,387 93 HRD 09 G!!! Z| 9. 09% GZ9001 G18 996 DLOR WERSON iO BM RAMANOR HC2S 5,449,387 1. 2 in aqueous solution, a cerium (IV) salt with a salt of said CERIUM (IV) CATALYST COMPOUNDS AND organic oxyacid advantageously having a pKa greater PROMOTING COMBUSTION OF than 1, or with a mixture of salts of organic oxyacids, at HYDROCARBON FUELS THEREWITH least one of which advantageously having a pKa greater CROSS-REFERENCE TO PARENT than 1. APPLICATION BRIEF DESCRIPTION OF THE DRAWINGS This is a continuation-in-part of our application Ser. FIGS. 1, 2 and 3 are infrared spectra of the com No. 08/077,362, filed Jun. 17, 1993, now abandoned and pounds of Examples 2, 4 and 8 according to the present assigned to the assignee hereof. O invention; FIG. 4 is a Raman spectrum of the compound of BACKGROUND OF THE INVENTION Example 23 according to this invention; 1. Field of the Invention FIGS. 5 and 6 are Raman spectra of compounds The present invention relates to novel cerium (IV) prepared according to U.S. Pat. No. 4,599,201/EP-A- oxidic compounds and to the preparation and applica 15 0,093,627; and tions thereof, and, more especially, to novel cerium (IV) FIG. 7 is a Raman spectrum of octoic acid, per se. oxidic compounds that are soluble in organic solvents, notably the hydrocarbons, or are convertible into ce DETAILED DESCRIPTION OF BEST MODE rium (IV) oxidic compounds that are soluble in such AND PREFERRED EMBODIMENTS OF THE hydrocarbons. 20 INVENTION 2. Description of the Prior Art More particularly according to the present invention, It is known to this art that cerium serves as a catalyst the organic oxyacid is preferably a carboxylic acid, but for numerous applications. In particular, it is useful for may also be an organic sulfuric, sulfonic, phosphoric or catalyzing the crosslinking of film-forming composi phosphonic acid having an appropriate pKa. The sub tions which dry via atmospheric oxidation, e.g., paint 25 ject novel cerium (IV) oxidic compounds are storage films, and it has been described as a catalyst for the stable in the pure state and also when dissolved in a oxidation of combustion residues and exhaust gases of hydrocarbon solvent, and the cerium (IV) content hydrocarbon fuels, e.g., diesel fuels, as described in U.S. thereof is at least 90%, typically at least 95%, and often Pat. No. 4,522,631. at least 99% of the total cerium content. For these various applications, it is important to pro The novel cerium (IV) oxidic compounds are ob duce cerium compounds in the cerium (IV) valence tained as yellow crystalline solids, or as yellow liquids. state, which is often the catalytically active state. Such They may be represented by the formula: cerium (IV) compounds are soluble in organic solvents, stable, and can be stored at high cerium concentrations. U.S. Pat. No. 4,599,201 to Gradeffetal, and counter 35 part EP-A-0093,627, both assigned to the assignee in which the radicals A, which may be the same or hereof, describe the synthesis of ceric carboxylates different, are each the residue of an organic oxyacid as which are soluble in organic solvents, from a solution of defined above of formula AH, p is an integer ranging a cerium (III) compound which is oxidized in an or from 0 to 5, n ranges from 0 to 2 and p is an integer ganic medium. Although this process presents several 40 ranging from 1 to 12. More particularly, in preferably is advantages, it also presents the following disadvan 0 or 2, p is 4, and m is 6. The cerium (IV) oxidic com tages: pounds containing the organic oxyacid residues in (1) the final products obtained are ill-defined and in which n is greater than 0 (preferably 2) are liquids particular comprise a mixture of cerium (III) and ce which are miscible with organic hydrocarbon solvents. rium (IV) values in which the proportion of Ce(IV) is 45 When n is 0, the compounds are crystalline solids not above 75%; which, if not soluble in hydrocarbon solvents, may be (2) the solutions obtained are extremely viscous and solubilized by reacting same with an acid, or a mixture their long term stability is doubtful; of acids, to provide a product in which n is greater than (3) hydrogen peroxide must be used; and O, e.g., is 2. (4) a fraction of the cerium values is lost, in the form X-ray analysis of the novel compounds, when crystal of water-soluble byproducts. lized, have shown that at least in certain instances the cerium atoms are arranged at the apexes of an octahe SUMMARY OF THE INVENTION dron with each of the eight faces capped by a triply Accordingly, a major object of the present invention bridging oxygen atom, and twelve carboxylic acid resi is the provision of novel cerium (IV) oxidic compounds 55 dues arranged in bidentate configuration along the that are improvedly soluble in organic solvents, and edges of the octahedron. In addition, two unidentate which otherwise avoid or conspicuously ameliorate the oxygen atoms, believed to be in hydroxyl groups, are above disadvantages and drawbacks to date character attached to two opposite cerium atoms of the Ce6 octa izing the state of this art.
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