WO2011136890A1 - Organosilicon glycol-based electrolytes with a hydroxy terminus - Google Patents

Organosilicon glycol-based electrolytes with a hydroxy terminus Download PDF

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Publication number
WO2011136890A1
WO2011136890A1 PCT/US2011/030415 US2011030415W WO2011136890A1 WO 2011136890 A1 WO2011136890 A1 WO 2011136890A1 US 2011030415 W US2011030415 W US 2011030415W WO 2011136890 A1 WO2011136890 A1 WO 2011136890A1
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electrolyte
electrolytes
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mixture
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French (fr)
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Robert C. West
Jose A. Pena Hueso
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Wisconsin Alumni Research Foundation
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Priority to JP2013507966A priority patent/JP2013526055A/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/0825—Preparations of compounds not comprising Si-Si or Si-cyano linkages
    • C07F7/083—Syntheses without formation of a Si-C bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
    • H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
    • H01G9/004—Details
    • H01G9/022—Electrolytes; Absorbents
    • H01G9/035—Liquid electrolytes, e.g. impregnating materials
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M6/00—Primary cells; Manufacture thereof
    • H01M6/14—Cells with non-aqueous electrolyte
    • H01M6/16—Cells with non-aqueous electrolyte with organic electrolyte
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00—Secondary cells; Manufacture thereof
    • H01M10/05—Accumulators with non-aqueous electrolyte
    • H01M10/052—Li-accumulators
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00—Secondary cells; Manufacture thereof
    • H01M10/05—Accumulators with non-aqueous electrolyte
    • H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
    • H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
    • H01M10/0566—Liquid materials
    • H01M10/0569—Liquid materials characterised by the solvents
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M2300/00—Electrolytes
    • H01M2300/0002—Aqueous electrolytes
    • H01M2300/0014—Alkaline electrolytes
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M6/00—Primary cells; Manufacture thereof
    • H01M6/14—Cells with non-aqueous electrolyte
    • H01M6/16—Cells with non-aqueous electrolyte with organic electrolyte
    • H01M6/162—Cells with non-aqueous electrolyte with organic electrolyte characterised by the electrolyte
    • H01M6/164—Cells with non-aqueous electrolyte with organic electrolyte characterised by the electrolyte by the solvent
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
    • Y02E60/10—Energy storage using batteries

Definitions

  • the present invention relates to ionic
  • electrolytes useful in connection with electrolytic capacitors and certain other energy storage devices.
  • hydroxy terminated organosilicon electrolytes that are particularly useful in an aqueous electrolytic capacitor environment.
  • organosilicon based electrolytes for energy storage applications.
  • Various of these organ silicon compounds have low vapor pressure, high flash point, and withstand high operating voltages.
  • Me 3 Si -CH 2 OCH 2 CH 2 OCH 2 CH 2 OCH 2 CH 2 OCH 2 CH 2 -OH (and various related compounds) as intermediates in the production of azacrown ethers. Apart from the fact that their syntheses required use of relatively expensive Me 3 Si-CH 2 I , there was no suggestion in their article to use these intermediates as electrolytes.
  • an electrolyte comprising:
  • R lf R 2 and R 3 are the same or different, and each is selected from the group consisting of alkyl moieties of less than five carbons. Most preferably each of R lf R 2 and R 3 is CH 3 . In any event, both m and n are less than 10, with m and n both most preferably lower than 5, and even more preferably with n equal to 2, 3 or 4.
  • electrolytic capacitors is triethylammonium azelaate, e.g. at less than 2% of the electrolyte.
  • other conventional salts useful with such energy storage devices can be included. See e.g. U.S. patent application publication 2010/0053847 regarding varied salts useful with such capacitors.
  • Various lithium based salts are also known to be compatible with a variety of organosilicon electrolytes.
  • Electrolytes can be created with mixtures of multiple such compounds. Alternatively, one of these compounds can be used with other materials (e.g. ethylene glycols; ditrimethyl silane terminated compounds) .
  • the electrolytes of the present invention are particularly suitable for use in environments where they will be exposed to/mixed with water.
  • aluminum electrolytic capacitors typically add a few percent of water to their electrolytic solution to help repair the aluminum material .
  • the invention provides an energy storage device (e.g. an electrolytic capacitor) which has such an electrolyte.
  • an energy storage device e.g. an electrolytic capacitor
  • the invention provides methods of producing hydroxy terminated organosilicon compounds having the following formula:
  • m and n are both less than 10, preferably both less than 5.
  • HO (CH 2 CH 2 0) r -0H with sodium cation, and then reacts the resultant with Me 3 Si (CH 2 ) q Cl and iodide anion.
  • q and r are both less than 10.
  • the present invention provides electrolytes that are highly useful in energy storage devices where the electrolyte contains or is exposed to water (e.g. especially in aluminum
  • electrolytic capacitors These electrolytes resist hydrolysis, can be used at relatively high voltages, and have reduced flammability concerns. Note that as n increases the flashpoint of these compounds also
  • the present invention also provides improved methods of synthesizing such compounds.
  • e 3 Si(CH 2 )I a starting material used in prior art syntheses, is undesirably expensive. Its use is avoided by replacing that compound with Me 3 Si(CH 2 )Cl and catalytic amounts of iodide anion, and adjusting concentrations and reaction conditions to minimize undesired byproducts.
  • Example 1 Mixture of 75% Me 3 Si - CH 2 OCH 2 CH 2 0CH 2 CH 2 -OH with about 20% HO-CH 2 CH 2 OCH 2 CH 2 OH , and about 5% Me 3 Si-CH 2 OCH 2 CH 2 OCH 2 CH 2 OCH 2 CH 2 -SiMe 3
  • Example 2 product the Example 1 mixture was dissolved in 500mL of water plus 1.5L of methanol and the nonpolar impurities extracted with hexane (2x75mL) . The solvent was then evaporated and the remaining compound dissolved in 1.5L of hexane and extracted with water (2xl00mL) . The solvent was then evaporated. Yield 115mL, 98% pure.
  • Example 3 compound distilled. Yield 180 g, 95% pure.
  • electrolyte salt preferably at less than 2%, and use that material in an energy storage device such as an aluminum electrolytic capacitor.
  • electrolytes can also have mixed therein various polyethylene glycol compounds and/or a
  • the present invention provides improved electrolytes, particularly electrolytes suitable for use in aqueous electrolytic capacitor environments. Improved methods for making them are also described.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Electrochemistry (AREA)
  • Power Engineering (AREA)
  • Organic Chemistry (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Manufacturing & Machinery (AREA)
  • General Chemical & Material Sciences (AREA)

Abstract

Disclosed are hydroxy terminated alkylsilane ethers with oligoethylene oxide substituents. They are suitable for use as electrolyte solvents and particularly well suited for use with aqueous environment electrolytic capacitors. Methods for synthesizing these compounds are also disclosed.

Description

ORGANOSILICON GLYCOL-BASED ELECTROLYTES WITH A HYDROXY TERMINUS
CROSS-REFERENCE TO RELATED APPLICATIONS
[0001] This application claims priority based on U.S. Serial No. 12/770,183 which was filed April 30, 2010.
FEDERALLY SPONSORED RESEARCH/DEVELOPMENT
[0002] This invention was made with United States government support awarded by the following agencies: NSF
0724469. The United States has certain rights in this invention.
BACKGROUND OF THE INVENTION
[0003] The present invention relates to ionic
electrolytes useful in connection with electrolytic capacitors and certain other energy storage devices.
More particularly it relates to hydroxy terminated organosilicon electrolytes that are particularly useful in an aqueous electrolytic capacitor environment.
[0004] Over the past decade our laboratory has been developing organosilicon based electrolytes for energy storage applications. Various of these organ silicon compounds have low vapor pressure, high flash point, and withstand high operating voltages.
[0005] For example, we previously reported the synthesis of some alkyl terminated trimethylsilyl oligoethylene glycol ethers in L. Zhang et al . , Highly
Conductive Trimethylsilyl Oligo (ethylene oxide)
Electrolytes For Energy Storage Applications, 18 J.
Mater. Chem. 3713-3717 (2008) . These materials had high ionic conductivity, good electrochemical stability, and good cycling performance when used as electrolyte solvents in lithium-ion cells. However, they were susceptible to being hydrolyzed under some conditions.
[0006] We also reported in U.S. patent application publication 2007/0065728 the concept of placing an alkyl spacer in such alkyl terminated compounds between the trimethylsilyl group and the remainder of the molecule. This helped the molecule resist hydrolysis. However, the compounds still did not achieve desired performance in certain environments.
[0007 ] One reason is that a variety of electrolytic capacitors use water to repair aluminum defects. See generally descriptions of electrolytic capacitors in U.S. patent 6,058,006. Conventional aluminum electrolytic capacitors sometimes use an electrolyte mix of gamma- butyrolactone , diethylene glycol, triethylammonium azelaate, and water. To achieve the advantages of our alkyl terminated organosilicon compounds with this type of capacitor there were attempts to replace the gamma- butyrolactone and diethylene glycol with them. However, alkyl terminated organosilicon electrolytes typically had performance issues in this environment.
[0008 ] In U. Yoon et al . , Efficient And Regioselective Photocyclization Reactions Of N- [ (ω- Trimethylsilylmethoxy) Polyoxalkyl] Phthalimides To
Azacrown Ethers, 41 Heterocycles 2665-2682 (1995) the authors reported the synthesis of Me3Si - CH2OCH2CH2OCH2CH2 OCH2CH2-OH, Me3Si- CH20CH2CH20CH2CH2-OH and
Me3Si -CH2OCH2CH2OCH2CH2OCH2CH2-OH (and various related compounds) as intermediates in the production of azacrown ethers. Apart from the fact that their syntheses required use of relatively expensive Me3Si-CH2I , there was no suggestion in their article to use these intermediates as electrolytes.
[ 0009 ] There is therefore a need for additional improvements with respect to organosilicon electrolytes for energy storage devices, particularly improvements relating to compatibility with water environments. SUMMARY OF THE INVENTION
[0010] In one aspect the invention provides an electrolyte comprising:
[0011] a salt; and
[0012] at least one compound having the following formula :
[0013] R2
[0014] I
[0015] Ri-Si- (CH2)m(OCH2CH2)n-OH
[0016] I
[0017] R3
[0018] In this compound Rlf R2 and R3 are the same or different, and each is selected from the group consisting of alkyl moieties of less than five carbons. Most preferably each of Rlf R2 and R3 is CH3. In any event, both m and n are less than 10, with m and n both most preferably lower than 5, and even more preferably with n equal to 2, 3 or 4.
[0019] One preferred salt for use with such
electrolytic capacitors is triethylammonium azelaate, e.g. at less than 2% of the electrolyte. However, alternatively other conventional salts useful with such energy storage devices can be included. See e.g. U.S. patent application publication 2010/0053847 regarding varied salts useful with such capacitors. Various lithium based salts are also known to be compatible with a variety of organosilicon electrolytes.
[0020] Electrolytes can be created with mixtures of multiple such compounds. Alternatively, one of these compounds can be used with other materials (e.g. ethylene glycols; ditrimethyl silane terminated compounds) .
[0021] The electrolytes of the present invention are particularly suitable for use in environments where they will be exposed to/mixed with water. For example, aluminum electrolytic capacitors typically add a few percent of water to their electrolytic solution to help repair the aluminum material .
[0022] In another aspect the invention provides an energy storage device (e.g. an electrolytic capacitor) which has such an electrolyte.
[0023] In yet another form the invention provides methods of producing hydroxy terminated organosilicon compounds having the following formula:
[0024] CH3
[0025] I
[0026] CH3-Si- (CH2)mO(CH2CH20)n-OH
[0027] I
[0028] CH3
[0029] In these compounds m and n are both less than 10, preferably both less than 5. To produce them one reacts HO (CH2CH20) r-0H with sodium cation, and then reacts the resultant with Me3Si (CH2) qCl and iodide anion. Here, q and r are both less than 10.
[0030] It will be appreciated that the present invention provides electrolytes that are highly useful in energy storage devices where the electrolyte contains or is exposed to water (e.g. especially in aluminum
electrolytic capacitors) . These electrolytes resist hydrolysis, can be used at relatively high voltages, and have reduced flammability concerns. Note that as n increases the flashpoint of these compounds also
increases .
[0031] The present invention also provides improved methods of synthesizing such compounds. In this regard, e3Si(CH2)I, a starting material used in prior art syntheses, is undesirably expensive. Its use is avoided by replacing that compound with Me3Si(CH2)Cl and catalytic amounts of iodide anion, and adjusting concentrations and reaction conditions to minimize undesired byproducts. [ 0032 ] The above and still other advantages of the present invention will be apparent from the description that follows. It should be appreciated, however, that the following description is merely of the preferred embodiments. The claims should therefore be looked to in order to understand the more comprehensive nature of the claimed invention.
[ 0033 ] DESCRIPTION OF THE PREFERRED EMBODIMENTS
[0034 ] We first describe improved syntheses for producing hydroxy terminated organosilicon compounds having the following formula:
[ 0035 ] CH3
[0036 ] I
[ 0037 ] CHa-Si- (CH2) m0 (CH2CH20) n-OH
[ 0038 ] I
[ 0039 ] CH3
[0040 ] Example 1 - Mixture of 75% Me3Si - CH2OCH2CH20CH2CH2-OH with about 20% HO-CH2CH2OCH2CH2OH , and about 5% Me3Si-CH2OCH2CH2OCH2CH2OCH2CH2-SiMe3
[ 0041 ] 700mL of diethyleneglycol are mixed with 38g of powdered NaOH and the mixture is stirred under vacuum at 80°C for 4 hours to eliminate most of the water produced in the reaction. After this time the NaOH was
essentially completely dissolved and the liquid no longer boiling.
[0042 ] The temperature was then lowered to 70 °C and 21g of Nal was added. Note that increasing the Nal levels above 20% molar equivalent would greatly increase byproducts and cost, and we selected our sodium iodide level lower accordingly.
[0043 J Vacuum is no longer needed at this point and the mixture is stirred until all Nal dissolves (about 30 minutes) . Then 116 g of chloromethyltrimethylsilane are added,, and the mixture is stirred for 3 hours at 70 °C and 1 hour at 80°C. After this 200 mL of water are added to the mixture and it is extracted with hexane (4x300mL) , the hexane is evaporated in rotovapor and the compound distilled. This lead to an initial yield of 160g of the 75/20/5 mixture. Interestingly, even this intermediate mixture turned out to have significant utility as an electrolyte .
[ 0044 ] Example 2 - e3Si-CH2OCH2CH2OCH2CH2-OH
[ 0045 ] In order to obtain a higher purity of the
Example 2 product, the Example 1 mixture was dissolved in 500mL of water plus 1.5L of methanol and the nonpolar impurities extracted with hexane (2x75mL) . The solvent was then evaporated and the remaining compound dissolved in 1.5L of hexane and extracted with water (2xl00mL) . The solvent was then evaporated. Yield 115mL, 98% pure.
[0046 ] Example 3 - Me3Si-CH2OCH2CH2OCH2CH20CH2CH2-OH
[0047 ] 700mL of triethyleneglycol are mixed with 45g of powdered NaOH and the mixture is stirred under vacuum at 90 °C for 3 hours to eliminate most of the water produced in the reaction. After this time the NaOH should be completely dissolved and the liquid no longer boiling.
[0048 ] The temperature is then lowered to 70 °C and 24 g of Nal are added. Vacuum is no longer needed and the mixture is stirred until all Nal dissolves (about 30 minutes) . Then 135 g of chloromethyltrimethylsilane are added and the mixture is stirred for 3 hours at 70°C and
1 hour at 80°C. After this 70 mL of water are added to the mixture and it is extracted with hexane (3x300mL) .
[0049 ] Half of the solvent is evaporated in rotavapor and 50mL of water are added to extract polar impurities. After that the remaining hexane is evaporated and the
Example 3 compound distilled. Yield 180 g, 95% pure.
[0050 ] Example 4- Me3Si- CH20CH2CH2OCH2CH20CH2CH2OCH2CH2-OH
[0051 ] 400mL of tetraethyleneglycol are mixed with 18.5g of powdered NaOH and the mixture is stirred under vacuum at 90 °C for 3 hours to eliminate most of the water produced in the reaction. After this time the NaOH should be completely dissolved and the liquid no longer boiling. The temperature is lowered to 70°C and 10.5 g of Nal are added .
[ 0052 ] Vacuum is no longer needed and the mixture is stirred until all Nal dissolves (about 30 minutes) . Then 56.4 g of chloromethyltrimethylsilane are added and the mixture is stirred for 3 hours at 70°C and 1 hour at 80°C. After this 50 mL of water are added to the mixture and it is extracted with hexane (3x200mL) . The solvent is evaporated in rotavapor and the compound distilled. After this 50mL of water are added and lOmL of hexane to extract nonpolar impurities. The water is evaporated in the rotavapor to give the compound. Yield 80 g.
[ 0053 ] Once we have a desired electrolyte (or
electrolyte mixture) one can add a conventional
electrolyte salt, preferably at less than 2%, and use that material in an energy storage device such as an aluminum electrolytic capacitor.
[ 0054 ] In addition to compound (s) of the present invention the electrolytes can also have mixed therein various polyethylene glycol compounds and/or a
ditrimethyl silane terminated electrolyte.
[ 0055 ] Various electrolytes of the present invention have been tested in aluminum electrolytic capacitors.
They have been found to resist hydrolysis and to be otherwise compatible with an aqueous environment, while still achieving other desirable properties expected from their alkyl terminated counterparts .
[0056 ] While various embodiments of the present invention have been described above, the present
invention is not limited to just these disclosed
examples. There are other modifications that are meant to be within the scope of the invention and claims. For example, m and n could have larger numbers than the preferred embodiments exemplify.
[ 0057 ] Thus, the claims should be looked to in order to judge the full scope of the invention.
[ 0058 ] Industrial Applicability
[ 0059 ] The present invention provides improved electrolytes, particularly electrolytes suitable for use in aqueous electrolytic capacitor environments. Improved methods for making them are also described.

Claims

Claims We claim:
1. An electrolyte comprising:
a salt ; and
at least one compound having the following formula:
R2
Ri-Si - (CH2)mO(CH2CH20)n-OH
R3
wherein Rx, R2 and R3 are the same or different, and each is selected from the group consisting of alkyl moieties of less than five carbons; and
wherein m and n are both less than 10.
2. The electrolyte of claim 1 wherein each of R1# R2 and R3 is CH3.
3. The electrolyte of claim 1, wherein m is lower than 5.
4. The electrolyte of claim 1, wherein n is 2 or 3 or 4.
5. The electrolyte of claim 1, further comprising water .
6. The electrolyte of claim 1, further comprising an ethylene glycol .
7. The electrolyte of claim 1, further comprising a ditrimethyl silane terminated electrolyte.
8. The electrolyte of claim 1 positioned in an energy storage device.
9. The electrolyte of claim 8, wherein the energy storage device is an aluminum electrolytic capacitor.
10. A method of producing a compound having the following formula:
CH3
I
CH3-S1- (CH2)raO(CH2CH20)n-OH
CH3
wherein m and n are both less than 10;
comprising:
the method comprising:
reacting HO (CH2CH20) r-0H with sodium cation; and then reacting the resultant with Me3Si (CH2) qCl and iodide anion;
wherein q and r are both less than 10.
11. The method of claim 10, wherein during the reaction the iodide anion is present at no more than 20% of the molarity of Me3Si (CH2) qCl .
PCT/US2011/030415 2010-04-30 2011-03-30 Organosilicon glycol-based electrolytes with a hydroxy terminus Ceased WO2011136890A1 (en)

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