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US4038459A Expired / Lapsed US ⏱️ 0.0 years remaining

Halogen complexing alcohols and nitriles

Assignee: Tracer Technologies Inc
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Filing: 1976-03-17
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Granted: 1977-07-26
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Expires: 1996-03-17
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Abstract

Abstract Halogen complexing alcohols and nitriles are disclosed as additives for use in complexing halogens in cells and batteries of the type which utilize the electrochemical reaction X 2 ⃡2X - , where X is Br, Cl, I, or a combination of these halides. The alcohols and nitriles form insoluble oil-like complexes with the halogens which prevent the halogens from being dissolved in the electrolyte of the cell or battery in which they are used.

Inventors

  • 👤 Alfred M. Ajami
  • 👤 Fraser M. Walsh
  • 👤 Dennis N. Crouse

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-01 17:11
CPC Classifications
H; H01; H01M; H01M8/00; H01M8/18; H01M8/184; H01M10/00; H01M10/36; H01M10/365; H01M4/00; H01M4/02; H01M4/36; H01M4/60; Y; Y02; Y02E; Y02E60/00; Y02E60/10; Y02E60/30; Y02E60/50

Claims Analysis

Total Claims: 28
Claim 1
Independent Claim 144 words
A process for improving the performance of current delivering electrochemical systems of the type which utilize a substance selected from the group consisting of bromine, chlorine, iodine, polyhalogen complexes, and mixtures thereof as its electrochemically active agent, said process comprising adding to the electrolyte of said system an additive comprising an alcohol or nitrile, which exists as a relatively insoluble liquid in aqueous metal halide solutions at 30° C. in the presence of one and more than one molar equivalent of halogen for every alcohol or cyano group in the additive, said additive being selected from the group consisting of compounds having the formulae: Z(--R--CN).sub.m Z(--R--OH).sub.m where R is an aliphatic group containing 1 to 8 carbon atoms, m is a number from 1 to 6, and Z is any chemical functionality which does not render the additive's halogen complex crystalline at 30° C.
Claim 2
Dependent Claim 144 words
A process for improving the performance of current delivering electrochemical systems of the type which utilize a substance selected from the group consisting of bromine, chlorine, iodine, polyhalogen complexes, and mixtures thereof as its electrochemically active agent, said process comprising adding to the electrolyte of said system an additive comprising an alcohol or nitrile, which exists as a relatively insoluble liquid in aqueous metal halide solutions at 30° C. in the presence of one and more than one molar equivalent of halogen for every alcohol or cyano group in the additive, said additive being selected from the group consisting of compounds having the formulae: Z(--R--CN).sub.m Z(--R--OH).sub.m where R is an aliphatic group containing 1 to 8 carbon atoms, m is a number from 1 to 6, and Z is any chemical functionality which does not render the additive's halogen complex crystalline at 30° C.
Claim 3
Dependent Claim 32 words
The process as set forth in claim 1 wherein Z is selected from the group consisting of alkyls, amides, carbocycles, carboxylates, halocarbons, halides, hydrogen, phosphonates, siloxanes, sulfonates, sulfones, sultones, and combinations thereof.
Claim 4
Dependent Claim 20 words
The process as set forth in claim 1 wherein Z is selected from the group consisting of halogen complexing functionalities.
Claim 5
Dependent Claim 46 words
The process as set forth in claim 3 wherein Z is selected from the group consisting of ammoniums, ammonium hydrohalides, amidimidines, amine oxides, betaines, esters, ethers, phosphobetaines, phosphoniums, pyridiniums, pyridyls, quaternary ammoniums, quaternary O-alkyl hydroxylammoniums, sulfobetaines, sulfoniums, sydnones, tertiary amines, tertiary amine hydrohalides, and combinations thereof.
Claim 6
Dependent Claim 36 words
The process as set forth in claim 1 where the additive is selected from the group consisting of: N-3-hydroxypropyl-N,N,N-triethyl ammonium bromide N-butyl-N,N-diethyl-N-2-hydroxyethyl ammonium bromide N,n-diethyl-N-2-hydroxyethyl-N-octyl ammonium bromide N-2-cyanoethyl-N,N-diethyl-N-methyl ammonium bromide N-2-cyanoethyl-N,N,N-triethyl ammonium bromide N-3-cyanopropyl-N,N,N-triethyl ammonium bromide.
Claim 7
Dependent Claim 169 words
An electrochemical cell comprising a case, a porous, conductive halogen electrode, an Me electrode where Me is selected from the group consisting of zinc and cadmium, an aqueous electrolyte containing an inorganic salt of the formula MX, where M is selected from the group consisting of cadmium and zinc and X is chosen from the group consisting of bromide, chloride, iodide, or combination of these halide ions, and an additive dissolved in said electrolyte comprising a compound, which exists as a relatively insoluble liquid in aqueous metal halide solutions at 30° C. in the presence of one or more than one molar equivalent of halogen for every alcohol or cyano group in the additive, said additive being selected from the group consisting of compounds having the following structural formulae: Z(--R--CN).sub.m Z(--R--OH).sub.m where R is an aliphatic group containing 1 to 8 carbon atoms, m is a number from 1 to 6, and Z is any chemical functionality which does not render the additive's halogen complex crystalline at 30° C.
Claim 8
Dependent Claim 169 words
An electrochemical cell comprising a case, a porous, conductive halogen electrode, an Me electrode where Me is selected from the group consisting of zinc and cadmium, an aqueous electrolyte containing an inorganic salt of the formula MX, where M is selected from the group consisting of cadmium and zinc and X is chosen from the group consisting of bromide, chloride, iodide, or combination of these halide ions, and an additive dissolved in said electrolyte comprising a compound, which exists as a relatively insoluble liquid in aqueous metal halide solutions at 30° C. in the presence of one or more than one molar equivalent of halogen for every alcohol or cyano group in the additive, said additive being selected from the group consisting of compounds having the following structural formulae: Z(--R--CN).sub.m Z(--R--OH).sub.m where R is an aliphatic group containing 1 to 8 carbon atoms, m is a number from 1 to 6, and Z is any chemical functionality which does not render the additive's halogen complex crystalline at 30° C.
Claim 9
Dependent Claim 32 words
The cell as set forth in claim 6 wherein Z is selected from the group consisting of alkyls, amides, carbocycles, carboxylates, halocarbons, halides, hydrogen, phosphonates, siloxanes, sulfonates, sulfones, sultones, and combinations thereof.
Claim 10
Dependent Claim 51 words
The cell as set forth in claim 6 wherein Z is selected from the group consisting of halogen complexing functionalities such as ammoniums, ammonium hydrohalides, amidimidines, amine oxides, betaines, esters, ethers, phosphobetaines, phosphoniums, pyridiniums, pyridyls, quaternary ammoniums, quaternary O-alkyl hydroxylammoniums, sulfobetaines, sulfoniums, sydnones, tertiary amines, tertiary amine hydrohalides, and combinations thereof.
Claim 11
Dependent Claim 38 words
The cell as set forth in claim 6 wherein said additive is a compound selected from the group consisting of: N-3-hydroxypropyl-N,N,N-triethyl ammonium bromide N-butyl-N,N-diethyl-N-2-hydroxyethyl ammonium bromide N,n-diethyl-N-2-hydroxyethyl-N-octyl ammonium bromide N-2-cyanoethyl-N,N-diethyl-N-methyl ammonium bromide N-2-cyanoethyl-N,N,N-triethyl ammonium bromide N-3-cyanopropyl-N,N,N-triethyl ammonium bromide.
Claim 12
Dependent Claim 15 words
The cell as set forth in claim 6 wherein said cell is a secondary cell.
Claim 13
Dependent Claim 15 words
The cell as set forth in claim 6 wherein said cell is a primary cell.
Claim 14
Dependent Claim 28 words
The cell as set forth in claim 6 further comprising means for storing the complex produced during charging to enable said cell to functions as a fuel cell.
Claim 15
Dependent Claim 15 words
The cell as set forth in claim 12 further comprising means for recirculating the electrolyte.
Claim 16
Dependent Claim 15 words
The cell as set forth in claim 13 further comprising means for storing said additive.
Claim 17
Dependent Claim 158 words
A water insoluble liquid complex substantially insoluble in water at 30° C. for use in electrochemical cells of the type which utilizes a halogen selected from the group consisting of chlorine, bromine, iodine, polyhalogen complexes, and mixtures thereof, said complex consisting essentially of a substance selected from the group consisting of chlorine, bromine, iodine, polyhalogen complexes, and mixtures thereof combined with an additive comprising an alcohol or nitrile, which exists as a relatively insoluble liquid in aqueous metal halide solutions at 30° C. in the presence of one and more than one molar equivalent of halogen for every alcohol or cyano group in the additive, said additive being selected from the group consisting of compounds having the formulae: Z(--R--CN).sub.m Z(--R--OH).sub.m where R is an aliphatic group containing 1 to 8 carbon atoms, m is a number from 1 to 6, and Z is any chemical functionality which does not render the additive's halogen complex crystalline at 30° C.
Claim 18
Dependent Claim 158 words
A water insoluble liquid complex substantially insoluble in water at 30° C. for use in electrochemical cells of the type which utilizes a halogen selected from the group consisting of chlorine, bromine, iodine, polyhalogen complexes, and mixtures thereof, said complex consisting essentially of a substance selected from the group consisting of chlorine, bromine, iodine, polyhalogen complexes, and mixtures thereof combined with an additive comprising an alcohol or nitrile, which exists as a relatively insoluble liquid in aqueous metal halide solutions at 30° C. in the presence of one and more than one molar equivalent of halogen for every alcohol or cyano group in the additive, said additive being selected from the group consisting of compounds having the formulae: Z(--R--CN).sub.m Z(--R--OH).sub.m where R is an aliphatic group containing 1 to 8 carbon atoms, m is a number from 1 to 6, and Z is any chemical functionality which does not render the additive's halogen complex crystalline at 30° C.
Claim 19
Dependent Claim 32 words
The complex as set forth in claim 15 wherein Z is selected from the group consisting of alkyls, amides, carbocycles, carboxylates, halocarbons, halides, hydrogen, phosphonates, siloxanes, sulfonates, sulfones, sultones, and combinations thereof.
Claim 20
Dependent Claim 20 words
The complex as set forth in claim 15 wherein Z is selected from the group consisting of halogen complexing functionalities.
Claim 21
Dependent Claim 46 words
The complex as set forth in claim 15 wherein Z is selected from the group consisting of ammoniums, ammonium hydrohalides, amidimidines, amine oxides, betaines, esters, ethers, phosphobetaines, phosphoniums, pyridiniums, pyridyls, quaternary ammoniums, quaternary O-alkyl hydroxylammoniums, sulfobetaines, sulfoniums, sydnones, tertiary amines, tertiary amine hydrohalides, and combinations thereof.
Claim 22
Dependent Claim 35 words
The complex as set forth in claim 15 wherein Z is selected from the group consisting of: N-3-hydroxypropyl-N,N,N-triethyl ammonium bromide N-butyl-N,N-diethyl-N-2-hydroxyethyl ammonium bromide N,n-diethyl-N-2-hydroxyethyl-N-octyl ammonium bromide N-2-cyanoethyl-N,N-diethyl-N-methyl ammonium bromide N-2-cyanoethyl-N,N,N-triethyl ammonium bromide N-3-cyanopropyl-N,N,N-triethyl ammonium bromide.
Claim 23
Dependent Claim 175 words
A battery of the type including a casing, an Me electrode, where Me is a metal selected from the group consisting of cadmium and zinc, a plurality of counter electrodes spaced apart from said Me electrode, a bipolar electrode interposed between each adjacent pair of said counter electrodes, an aqueous electrolyte containing an inorganic salt of the formula MX, where M is selected from the group consisting of bromide, chloride, iodide, and combinations thereof, and an additive in said electrolyte comprising an alcohol or nitrile, which exists as a relatively insoluble liquid in aqueous metal halide solutions at 30° C. in the presence of one and more than one molar equivalent of halogen for every alcohol or cyano group in the additive, said additive being selected from the group consisting of compounds having the formulae: Z(--R--CN).sub.m Z(--R--OH).sub.m where R is an aliphatic group containing 1 to 8 carbon atoms, m is a number from 1 to 6, and Z is any chemical functionality which does not render the additive's halogen complex crystalline at 30° C.
Claim 24
Dependent Claim 175 words
A battery of the type including a casing, an Me electrode, where Me is a metal selected from the group consisting of cadmium and zinc, a plurality of counter electrodes spaced apart from said Me electrode, a bipolar electrode interposed between each adjacent pair of said counter electrodes, an aqueous electrolyte containing an inorganic salt of the formula MX, where M is selected from the group consisting of bromide, chloride, iodide, and combinations thereof, and an additive in said electrolyte comprising an alcohol or nitrile, which exists as a relatively insoluble liquid in aqueous metal halide solutions at 30° C. in the presence of one and more than one molar equivalent of halogen for every alcohol or cyano group in the additive, said additive being selected from the group consisting of compounds having the formulae: Z(--R--CN).sub.m Z(--R--OH).sub.m where R is an aliphatic group containing 1 to 8 carbon atoms, m is a number from 1 to 6, and Z is any chemical functionality which does not render the additive's halogen complex crystalline at 30° C.
Claim 25
Dependent Claim 32 words
The battery as set forth in claim 20 wherein Z is selected from the group consisting of alkyls, amides, carbocycles, carboxylates, halocarbons, halides, hydrogen, phosphonates, siloxanes, sulfonates, sulfones, sultones, and combinations thereof.
Claim 26
Dependent Claim 20 words
The battery as set forth in claim 20 wherein Z is selected from the group consisting of halogen complexing functionalities.
Claim 27
Dependent Claim 38 words
The battery as set forth in claim 20 wherein said additive is a compound selected from the group consisting of: N-2-hydroxypropyl-N,N,N-triethyl ammonium bromide N-butyl-N,N-diethyl-N-2-hydroxyethyl ammonium bromide N,n-diethyl-N-2-hydroxyethyl-N-octyl ammonium bromide N-2-cyanoethyl-N,N-diethyl-N-methyl ammonium bromide N-2-cyanoethyl-N,N,N-triethyl ammonium bromide N-3-cyanopropyl-N,N,N-triethyl ammonium bromide.
Claim 28
Dependent Claim 18 words
The battery as set forth in claim 20 further comprising means for storing the complex produced during charging.

References Cited (Backward Citations)

US3811945A Cited
US3816177A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1980-07-25 1981-01-24 1981-07-26 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1984-07-25 1985-01-24 1985-07-26 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1988-07-25 1989-01-24 1989-07-26 $7700.00 Window Closed / Lapsed

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