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United States Patent Office Patented Oct 3,764,385 United States Patent Office Patented Oct. 9, 1973 2 3,764,385 a high energy density electric battery by utilizing Li or ELECTREC BATTERY USENG COMPLEXED N. Al anodes with a charge transfer agent comprising Li salts ORGANIC LITHUM SALTS AS CHARGE in either their molten or solid state. These batteries have TRANSFERAGENT been described in U.S. Pats. 3,445,288; 3,506,490; and Arthur W. Langer, Jr., Watchung, and Thomas A. 5 3,506,492. All the batteries so described must be oper Whitney, Linden, N.J., assignors to Esso Research and ated at temperatures in excess of 250 C. Engineering Company A new approach to designing a high energy density bat No Drawing. Continuation-in-part of application Ser. No. 808,328, Mar. 18, 1969. This application Dec. 22, 1970, tery has been described in U.S. Pat. No. 3,404,042. The Ser. No. 100,813 batteries described therein represent an improvement over Int, C. H01m 29/00, 43/00 10 the prior art. U.S. C. 136-6R 6 Claims SUMMARY OF THE INVENTION Novel batteries are described herein which are not sub ABSTRACT OF THE DISCLOSURE ject to the problems encountered in the prior art, More An electric battery which is characterized by use there 5 specifically, the electric batteries of the instant invention in of a complexed inorganic lithium salt as the charge achieve high energy densities by utilizing as a charge trans transfer agent between the electrodes. The electric bat fer agent a complex of an inorganic lithium salt and a tery can be a primary or a secondary electrical energy monomeric or polymeric polyfunctional Lewis base. The first component of the charge transfer agent of this storage device, and in a preferred embodiment the com invention is an inorganic lithium salt having a lattice plexed lithium salt is dissolved in an aromatic solvent. 20 energy no greater than about that of lithium hydride, pref erably no greater than about 210 kilocalories per mole CROSS REFERENCE TO RELATED APPLICATIONS (measured at about 18 C.). The lattice energies of var This case is a continuation-in-part of U.S. application ious inorganic lithium salts may be found in the "Hand Ser. No. 808,328, filed on Mar. 18, 1969, in the names of 25 book of Electrochemical Constants' by Roger Parsons Arthur W. Langer, Jr. and Thomas A. Whitney. (Academic Press, 1959). The lithium salts useful for this invention must have BACKGROUND OF THE INVENTION less than the requisite maximum lattice energy and must (1) Field of the invention also be inorganic in nature; they will normally have melt 30 ing points less than about 650 C. The term "inorganic,” This invention relates to an electric battery which is for the purposes of this invention, means that (1) there characterized by use therein of a complexed inorganic is no hydrocarbon radical bonded directly to the lithium lithium Salt as the charge transfer agent between the elec atom and (2) any hydrocarbon radical present in the trodes. The electric battery can be a primary or a second anion moiety must be indirectly bonded to the lithium. ary electrical energy storage device, and in a preferred 35 through a third atom which cannot be nitrogen, oxygen, embodiment the complexed lithium salt is dissolved in an phosphorus or sulfur. Thus, lithium compounds such as aromatic solvent. n-butyllithium and phenyllithium do not meet criteria (1) (2) Prior art and are outside the scope of this invention. Similarly, It is desirable to achieve maximum energy density (watt compounds of the type LiOR, LiNHR or LiNR2, LiSR, hrs./lb.) and maximum current density (watts./lb.) in 40 LiPR2 LiOOCR do not meet criteria (2) and are there an electric battery. Since one of the large contributors to fore outside the scope of this invention. On the other hand, the Weight of a battery is the charge transfer agent, it compounds of the type LiNH2, LiCN, LiSCN, LiSH, has been deemed desirable to substitute lower density or LiCOs, LiHCO3, LiAlR2Cl2, LiAlH(OR)3, LiBH(OR3), ganic solutions for the aqueous solutions primarily used. LiAIRaH, etc. are within the scope of this invention. Another advantage of using organic solutions as the 45 Specific nonlimiting examples of useful inorganic lith charge transfer agent is that certain desirable electrode ium salts are those in which the anion is: amide, azide, materials can be utilized. For example, Li, which is the chlorate, cyanide, fluosulfonate, chloride, bromide or oretically capable of the highest energy density of all the iodide, hydrogen sulfate, hydrosulfide, iodate, nitrate, hy anodic materials, cannot be used with an aqueous charge pochlorite, nitrite, sulfate, thiocyanate, perchlorate, Brs, transfer agent because of its inherent instability in water 13, CIBr2, IBr2, ICl4, BrF4, IFs, etc. and other aprotic media. The organic solutions which 50 Also useful are those inorganic lithium salts in which have been used fall into two categories, each with its own the anion is a complex metal anion which may be repre disadvantages. sented by the formula R'MXm wherein n is an integer In Electrochemical Technology, vol. 6, No. 1-2, Jan of 0 to 6 inclusive depending on the valence of M, m is uary-February 1968, pp. 28-35, a series of electric bat an integer and (n--in-1) equals the valence of M, X teries are described which are capable of yielding high 55 is a halogen, R' is a C1-Cao alkyl, aryl or aralkyl radical energy densities. These batteries utilize a lithium anode, and M is a metal selected from the group consisting of a charge transfer medium comprising LiClO4 or LiAlCl4 beryllium, magnesium, Group I-B elements, Group II-B dissolved in a solvent selected from the group consisting elements, Group III elements, Group IV-A elements other of acetonitrile, dimethyl formamide, propionitrile, di 60 than carbon and silicon, Group V-A elements other than methyl sulfoxide, methylacetate, 4-butyrolactone, nitro nitrogen; and the transition metals, i.e. subgroup B of methane, 2-pentanone, propylene carbonate and dimethyl Groups IV through VIII. The Periodic Table employed in carbonate, and a AgCl, cathode. Various problems with describing this invention is that which appears on the back these systems are encountered due to the tendency of the cover of "Handbook of Chemistry and Physics' (Chemi solvent to undergo oxidation and reduction reactions dur cal Rubber Co., 49th Edition). ing battery use. Further, the more effective solvents of 65 Nonlimiting examples of useful complex metal anions this series, i.e., propylene carbonate, dimethylformamide, include the hydridoaluminates, the hydridoborates, the dimethyl sulfoxide, and similar solvents such as hexa chloroaluminates (tetra-, hepta-, etc.), the aluminum al methylphosphoramide are expensive. Batteries which also kyl halides AuBra, BF4, BeCl4, SnCls, PF6, TiCl, FeCl utilize these solvents are described in U.S. Pat. No. 3,514 Cr(CO)5I, MnOls, Ni(CN)4, VFs, HgCl, BH, UF 337. These batteries suffer from the same disadvantages. 70 AsF6, etc. It is also known in the art that it is possible to achieve Preferably, the inorganic lithium salt is one of the 3,764,385 3 4 following: lithium chloride, lithium bromide, lithium iodide, lithium aluminum hydride, lithium borohydride, (IV) (R)b (O) lithium nitrate, lithium nitrite, lithium hexafluorophos phate, lithium tetrafluoborate, lithium tetraphenylborate, lithium perchlorate, lithium azide, LiAsF6, and LiBeF. wherein a is 1 or 2, depending on the valence of Y or Y'; The most preferred inorganic lithium saits are LiBr, b is 0 or 1, depending on the valence of Y or Y'; c is LiI, LiBH, LiAlH4 LiBF4, and combinations thereof. 0 an integer of 0 to 10,000, inclusive; d is 0, 1 or 2, de The complexing agent contains at least two function pending on the valence of Y or Y'; e is an integer of 0 alities; at least one functionality is a secondary amine to 3, inclusive; R is the same or different C1-C alkyl group, a tertiary amine group, an amine oxide group, a radical; R' is hydrogen when d is 0 or is the same or secondary phosphine group, a thioether group, a sulfone different C1-C4 alkyl radical or C-C aryl or aralkyl group or a sulfoxide group; at least one other functionality 5 radical when d is 0, 1 or 2; Y is a nitrogen, sulfur or is a secondary amine group, a tertiary amine group, a sec phosphorus atom; Y is a nitrogen, oxygen, sulfur or ondary phosphine group, a tertiary phosphine group, a phosphorus atom; and Z is a nonreactive radical selected thioether group, or an ether group. from the group consisting of (1) Ca-Cio cycloaliphatic The terms "amine oxide group' and "phosphine oxide or aromatic radicals and their lower alkyl derivatives group,” for the purposes of this invention mean that the 20 wherein said radicals are attached to the Y and Y atoms underlying amine and phosphine must be tertiary (rather in Formula I and the nitrogen atoms in Formula II at than primary or secondary) in nature. Thus, the desired 1,2-positions on the aromatic rings or 1,2- or 1,3-posi "amine oxide group' and "phosphine oxide group” have tions on the cycloaliphatic rings; and (2) 1 to 4 meth the formulas: ylenic radicals, wherein each methylenic radical contains 25 0 to 2 monovalent hydrocarbon radicals of 1 to 6 carbon 9 atoms. R-N-R and R-N-R Preferably, the chelating Lewis base has (a) at least R R one Y being nitrogen and at least one Y being oxygen (i.e. an aminoether) or (b) all the Y and Y atoms being The oxides of primary or secondary amines or phosphines 30 the same atom (i.e.
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