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Redox Shuttle Additives

Argonne National Laboratory

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<p align="LEFT">
	<i><font color="#808285" size="1"><font color="#808285" size="1">Charge Transfer Mechanism for Li-ion Battery Overcharge Protection &mdash; The boron and fluorine additive is in the electrolyte. When the battery is overcharged, the redox shuttle will be oxidized by losing an electron to the positive electrode. The radical cation formed will then diffuse back to the negative electrode, causing the cation to obtain an electron and be reduced. The net reaction is to shuttle electrons from the positive electrode to the negative electrode without causing chemical damage to the battery.</font></font></i></p>

Charge Transfer Mechanism for Li-ion Battery Overcharge Protection — The boron and fluorine additive is in the electrolyte. When the battery is overcharged, the redox shuttle will be oxidized by losing an electron to the positive electrode. The radical cation formed will then diffuse back to the negative electrode, causing the cation to obtain an electron and be reduced. The net reaction is to shuttle electrons from the positive electrode to the negative electrode without causing chemical damage to the battery.

Technology Marketing Summary

As the demand for hybrid and electric vehicles continues to grow, so does the demand for lithium-ion batteries that are safer, more powerful, and less expensive. These Argonne additives will help meet that demand.

Description

A series of novel redox shuttle additives for lithium ion batteries for the purpose of overcharge protection and increased battery safety.  The additives not only can provide excellent overcharge protection in lithium-ion batteries but are also compatible with conventional carbonate-based electrolytes. These novel shuttle additives also provide improved solubility in carbonate based electrolyte.

Benefits
  • Prevent overcharge and improves safety,
  • Balance cell in a battery pack,
  • Reduce cost, and
  • Increase battery reliability.
Applications and Industries
  • Electrodes used in batteries for
  • Electric and plug-in hybrid electric vehicles;
  • Portable electronic devices;
  • Medical devices; and
  • Space, aeronautical, and defense-related devices.
Patents and Patent Applications
ID Number
Title and Abstract
Primary Lab
Date
Patent 7,851,092
Patent
7,851,092
Redox shuttles for overcharge protection of lithium batteries
The present invention is generally related to electrolytes containing novel redox shuttles for overcharge protection of lithium-ion batteries. The redox shuttles are capable of thousands hours of overcharge tolerance and have a redox potential at about 3-5.5 V vs. Li and particularly about 4.4-4.8 V vs. Li. Accordingly, in one aspect the invention provides electrolytes comprising an alkali metal salt; a polar aprotic solvent; and a redox shuttle additive that is an aromatic compound having at least one aromatic ring with four or more electronegative substituents, two or more oxygen atoms bonded to the aromatic ring, and no hydrogen atoms bonded to the aromatic ring; and wherein the electrolyte solution is substantially non-aqueous. Further there are provided electrochemical devices employing the electrolyte and methods of making the electrolyte.
Argonne National Laboratory 12/14/2010
Issued
Application 20110294018
Application
20110294018
REDOX SHUTTLES FOR HIGH VOLTAGE CATHODES
A compound has general Formula I, II, III, or IV: ##STR00001## where X and Y are independently a group of Formula (A): ##STR00002## and Z a group of Formula (B): ##STR00003## The compounds may be used in electrolytes and electrochemical devices.
Argonne National Laboratory 05/24/2011
Filed
Application 20110294003
Application
20110294003
POLYETHER-FUNCTIONALIZED REDOX SHUTTLE ADDITIVES FOR LITHIUM ION BATTERIES
Compounds may have general Formula I, II, or III: ##STR00001## where R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are independently H, F, Cl, Br, CN, NO.sub.2, a alkyl group, a haloalkyl group, a phosphate group, a polyether group; or R.sup.1 and R.sup.2, or R.sup.3 and R.sup.4, or R.sup.2 and R.sup.3 (in the case of Formula II) may join together to form a fused ring on the benzene ring; and X and Z are independently a group of Formula A: ##STR00002## where R.sup.5 and R.sup.6 and R.sup.7 are independently H, F, Cl, Br, CN, NO.sub.2, a alkyl group, a haloalkyl group, a phosphate group, or a polyether group; R.sup.7 is H, F, Cl, Br, CN, NO.sub.2, a alkyl group, a haloalkyl group, a phosphate group, or a polyether group; n is an integer from 1 to 8; and m is an integer from 1 to 13. Such compounds may be used as redox shuttles in electrolytes for use in electrochemical cells, batteries and electronic devices.
Argonne National Laboratory 05/24/2011
Filed
Patent 8,283,074
Patent
8,283,074
Electrolyte salts for nonaqueous electrolytes
Metal complex salts may be used in lithium ion batteries. Such metal complex salts not only perform as an electrolyte salt in a lithium ion batteries with high solubility and conductivity, but also can act as redox shuttles that provide overcharge protection of individual cells in a battery pack and/or as electrolyte additives to provide other mechanisms to provide overcharge protection to lithium ion batteries. The metal complex salts have at least one aromatic ring. The aromatic moiety may be reversibly oxidized/reduced at a potential slightly higher than the working potential of the positive electrode in the lithium ion battery. The metal complex salts may also be known as overcharge protection salts.
10/09/2012
Issued
Patent 8,877,390
Patent
8,877,390
Redox shuttles for lithium ion batteries
Compounds may have general Formula IVA or IVB. ##STR00001## where, R.sup.8, R.sup.9, R.sup.10, and R.sup.11 are each independently selected from H, F, Cl, Br, CN, NO.sub.2, alkyl, haloalkyl, and alkoxy groups; X and Y are each independently O, S, N, or P; and Z' is a linkage between X and Y. Such compounds may be used as redox shuttles in electrolytes for use in electrochemical cells, batteries and electronic devices.
Argonne National Laboratory 11/04/2014
Issued
Patent 9,203,112
Patent
9,203,112
Redox shuttles having an aromatic ring fused to a 1,1,4,4-tetrasubstituted cyclohexane ring
An electrolyte includes an alkali metal salt; an aprotic solvent; and a redox shuttle additive including an aromatic compound having at least one aromatic ring fused with at least one non-aromatic ring, the aromatic ring having two or more oxygen or phosphorus-containing substituents.
12/01/2015
Issued
Technology Status
Technology IDDevelopment StageAvailabilityPublishedLast Updated
IN-05-012, IN-08-024, IN-09-082, IN-09-084, IN-09-086, IN-10-076, IN-11-128DevelopmentAvailable07/16/201307/16/2013

Contact ANL About This Technology

To: Elizabeth Brewer<partners@anl.gov>