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WO2018030564A1 - Procédé de préparation d'un liquide ionique électrolytique contenant un groupe éther et ayant une conductivité ionique élevée - Google Patents

Procédé de préparation d'un liquide ionique électrolytique contenant un groupe éther et ayant une conductivité ionique élevée Download PDF

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Publication number
WO2018030564A1
WO2018030564A1 PCT/KR2016/008949 KR2016008949W WO2018030564A1 WO 2018030564 A1 WO2018030564 A1 WO 2018030564A1 KR 2016008949 W KR2016008949 W KR 2016008949W WO 2018030564 A1 WO2018030564 A1 WO 2018030564A1
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Prior art keywords
ionic liquid
electrolyte
methylpiperidinium
group
producing
Prior art date
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Ceased
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PCT/KR2016/008949
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English (en)
Korean (ko)
Inventor
유정복
최정철
윤효상
송준용
주소경
이동엽
김완주
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Chemtech Research Inc
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Chemtech Research Inc
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Priority to KR1020197002698A priority Critical patent/KR102127081B1/ko
Priority to PCT/KR2016/008949 priority patent/WO2018030564A1/fr
Publication of WO2018030564A1 publication Critical patent/WO2018030564A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • 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
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
    • H01G11/00—Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors; Processes for the manufacture thereof or of parts thereof
    • H01G11/54—Electrolytes
    • H01G11/58—Liquid electrolytes
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M8/00—Fuel cells; Manufacture thereof
    • H01M8/08—Fuel cells with aqueous electrolytes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10F—INORGANIC SEMICONDUCTOR DEVICES SENSITIVE TO INFRARED RADIATION, LIGHT, ELECTROMAGNETIC RADIATION OF SHORTER WAVELENGTH OR CORPUSCULAR RADIATION
    • H10F10/00—Individual photovoltaic cells, e.g. solar cells
    • 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
    • H01M2300/0017—Non-aqueous electrolytes
    • H01M2300/0025—Organic electrolyte
    • 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
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • 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
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/542—Dye sensitized solar cells
    • 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
    • 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
    • Y02E60/13—Energy storage using capacitors
    • 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
    • Y02E60/30—Hydrogen technology
    • Y02E60/50—Fuel cells

Definitions

  • the present invention relates to a method for preparing an ionic liquid including an ether group having excellent thermal stability by TGA for a secondary battery electrolyte and having high ionic conductivity and an electrochemical window in solution. More specifically, the present invention has a cation in which an ether group is introduced into imidazolium (Imidazolium), pyrrolidinium (Pyrrolidinium), piperidinium (Piperidinium), morphorinium (Morpholinium), ammonium (temonium), and tetra Tetrafluoroborate (BF 4 ), Hexafluorophosphate (PF 6 ), Bisfluorosulfonylimide (FSI) and Bistrifluoromethanesulfonylimide (TFSI)
  • the present invention relates to a method for preparing an ionic liquid for an secondary battery energy storage device (ESS) electrolyte comprising an ether group.
  • ESS secondary battery energy storage device
  • the redox flow battery is a secondary battery in which charging and discharging occur due to the redox reaction of the electrolyte.
  • the main difference from the general battery is that the charge and discharge are performed while circulating the electrolyte in which energy is stored.
  • the charging and discharging is carried out in a stack where oxidation and reduction electrochemical reactions occur, and the electricity is stored in the electrolyte in a separate tank.
  • the battery stores power in the electrolyte. Can be discharged.
  • the redox flow battery has some commercialized water systems, but has a problem of low energy density of less than 26WH / L and low cell voltage of less than 1.25V. There is a limit.
  • a non-aqueous redox flow battery electrolyte having excellent thermal stability and high ionic conductivity and voltage is prepared by preparing an ionic liquid including ether group in a new cation.
  • imidazolium (Imidazolium), Pyrrolididinium (Pyrrolidinium), Piperidinium, Morpholinium (Morpholinium), Ammonium (Ammonium) using 1-bromoethylmethylether (1-Bromoethylmethylether) substituted by a reaction containing a cation containing a methoxyethyl ether group Tetrafluoroborate (BF 4 ), Hexafluorophosphate (Hexafluorophosphate: PF 6 ), bisfluorosulfonylimide (FSI) and bistrifluoromethanesulfonylimide (TFSI) in a method for producing an ionic liquid having an anion.
  • the ionic liquid for electrolytes containing an ether group in the cation has a thermal stability of more than 388 ° C and a high ionic conductivity of more than 40.1 mS / cm in solution phase as a result of differential thermal gravimetric analysis (TGA) analysis.
  • TGA differential thermal gravimetric analysis
  • ionic liquid substituted with an alkyl group in cation with a range of 2.0V or more is produced.
  • Non-aqueous redox flow battery, electrolyte for lithium ion secondary battery, ultra capacitor, capacitor, dye-sensitized solar cell The present invention has been completed as the energy storage device electrolyte and electrochromic (EC) material such as electrolyte are expected to be very high.
  • the cations include 1-bromoethyl methyl in methylimidazolium, methylpyrrolidinium, methylpiperidinium, methylmorpholinium, and triethylammonium.
  • An ionic liquid is provided having 1.0-1.2 equivalents of bisfluorosulfonylimide (FSI) and bistrifluoromethanesulfonylimide (TFSI) as anions.
  • FSI bisfluorosulfonylimide
  • TFSI bistrifluoromethanesulfonylimide
  • thermogravimetric analysis is in the range of 290 ⁇ 430 °C
  • Solution preparation for ionic conductivity measurements ranges from 31.0 to 46.0 mS / cm at 25 ° C in ionic liquid 1 molar (mol / L) acetonitrile, 0.1 mol + vanadium acetoacetonite 0.1 mol + acetonitrile
  • the electrochemical potential window is between 3.5 and 6.0 V.
  • the ionic liquid of the present invention has a very high ionic conductivity, a high decomposition point and a wide electrochemical potential window due to the improvement of the thermal decomposition temperature, and therefore, an electrolyte and an ultracapacitor for a non-aqueous redox flow battery and a lithium ion secondary battery.
  • High capacity capacitors), capacitors, dye-sensitized solar cell electrolytes such as electrolytes and electrochromic (EC) materials can be widely used.
  • the ionic liquid containing an ether group in the cation according to the present invention has an excellent thermal stability of 388 ° C. on average, and has a wide electrochemical potential window of at least 40.0 mS / cm and at least 5.1 V. It is thought to be very useful as an electrolyte and electrochromic (EC) material for energy storage devices such as flow batteries, lithium ion secondary batteries, ultra capacitors, capacitors, and dye-sensitized solar cells.
  • EC electrochromic
  • the present invention is a method for producing an ionic liquid including an ether group having excellent thermal stability by TGA for a secondary battery electrolyte and having a high ionic conductivity and an electrochemical window in solution.
  • the present invention has a cation in which an ether group is introduced into imidazolium (Imidazolium), pyrrolidinium (Pyrrolidinium), piperidinium (Piperidinium), morpholinium (Morpholinium), and ammonium (Ammonium), and tetrafluoro Tetrafluoroborate (BF 4 ), Hexafluorophosphate (PF 6 ), Bisfluorosulfonylimide (FSI) and Bistrifluoromethanesulfonylimide (TFSI) as anions
  • ESS energy storage device
  • Ether ether
  • the anion may be selected from tetrafluoroborate (BF 4 ), hexafluorophosphate (PF 6 ), bisfluorosulfonylimide (FSI) and bistrifluoromethanesulfonyl Imide (Bistrifluoromethanesulfonylimide (TFSI)) can be selected from the group consisting of.
  • the anion may be selected from sodium tetrafluoroborate (NaBF 4 ), potassium hexafluorofluorophosphate (KPF 6 ), lithium bisfluorosulfonylimide (LiFSI), and lithium bistrifluorofluoride.
  • Rho methanesulfonylimide Lithiumbistrifluoromethanesulfonylimide: LiTFSI).
  • the anion may be selected from hydrotetrafluoroborate (HBF 4 ), hydrohexafluorophosphate (HPF 6 ), hydrobisfluorosulfonylimide (HFSI) and hydrobistrifluorofluoro. It can be selected from the group consisting of acid reagents such as mydsulithiumbistrifluoromethanesulfonylimide (HTFSI).
  • a reagent such as 2-Bromoethyl methyl ether, 2-Chloroethyl methyl ether, 2-Iodoethyl ether or more.
  • methylimidazolium (Methylimidazolium), methylpyrrolidinium (Methylpyrrolidinium), methylpiperidinium (Methylpiperidinium), methylmorpholinium (Methylmorpholinium) and triethylammonium (Triethylammonium) is 1.0 ⁇ 10mol Sodium tetrafluoroborate (NaBF 4 ), potassium hexafluorophosphate (KPF 6 ), lithium bisfluorosulfonylimide (LiFSI) and lithium bistrifluoromethanesulfonyl 0.8-10 mol of imide (Lithiumbistrifluoromethanesulfonylimide: LiTFSI) is added to the reaction, followed by synthesis of an organic layer to prepare an ionic liquid for electrolyte.
  • LiTFSI lithium bisfluorosulfonylimide
  • methylimidazolium (Methylimidazolium), methylpyrrolidinium (Methylpyrrolidinium), methylpiperidinium (Methylpiperidinium), methylmorpholinium (Methylmorpholinium) and triethylammonium (Triethylammonium) is 1.0 ⁇ 10mol Hydrotetrafluoroborate (HBF 4 ), Hydrohexafluorofluorophosphate (HPF 6 ), Hydrobisfluorosulfonylimide (HFSI), Hydrobistrifluoromethanesulfonyl Reaction and synthesis are performed by adding 0.8-10 mol of mead (Hydrolithiumbistrifluoromethanesulfonylimide: HTFSI) to prepare an ionic liquid for electrolyte.
  • an electrolyte or a conductive solvent of ACN (Acetonitrile), EC (Ethylene carbonate), PC (Propylene carbonate), and DMC (Dimethyl) are mixed with an ionic liquid + Vanadium (III) Acetylacetonate + Acetonitrile.
  • Ether used for electrolyte composition such as carbonate), DEC (Diethyl carbonate), EMC (Ethyl methyl carbonate), EA (Ethylene acetate), and DMM (Dipropylene glycol dimethyl ether), DME (Dimethyl ether), DEE (Diethyl ether)
  • a mixed composition of an ionic liquid containing an (Ether) group and a conductive solvent may be used.
  • the ionic liquid according to the present invention is a non-aqueous redox flow battery, a lithium ion secondary battery, an ultracapacitor (ultra capacitor), an energy storage device electrolyte such as a capacitor, a dye-sensitized solar cell electrolyte, and electrochromic (EC). ) Can be used as a material.
  • the components of the product as described above may be used as composition additives, regulators or promoters or main raw materials.
  • the structural information of the ionic liquid synthesized according to the following preparation was measured by 1 H-, 19 F-NMR, and the basis of thermal stability was determined by TGA, and the ion conductivity (mS / cm) and electricity by LSV.
  • the chemical potential window (V) was measured and the result is described in each Example.
  • MeoMIM-Br Add 40 g (0.181 mol) of MeoMIM-Br to a round flask, add distilled water, add 62.3 g (0.217 mol) of LiTFSI, and stir at room temperature for 12 hours. After the reaction was completed, the solvent was removed by distillation under reduced pressure to obtain 71.62 g of MeoMIM-TFSI.
  • MeoMIM-Br Add 40 g (0.181 mol) of MeoMIM-Br to a round flask, add 23.8 g (0.217 mol) of acetone and NaBF 4 , and stir at room temperature for 12 hours. After the reaction was completed, the solvent was removed using distillation under reduced pressure to obtain 40.06 g of MeoMIM-BF 4 .
  • MeoMIM-Br 40 g (0.181 mol) of MeoMIM-Br is added to a round flask, and 50 ml of CH 2 Cl 2 and 39.9 g (0.217 mol) of KPF 6 are added thereto, followed by stirring at room temperature for 12 hours. After the reaction was completed, the solvent was distilled under reduced pressure to obtain 49.20 g of MeoMIM-PF 6 .
  • MeoMPyr-Br 41.85 g (0.186 mol) of MeoMPyr-Br is added to a round flask, distilled water is added, and 49.12 g (0.224 mol) of LiTFSI is added thereto, followed by stirring at room temperature for 12 hours. After the reaction was completed, the solvent was removed by distillation under reduced pressure to obtain 55.8 g of MeoMPyr-TFSI.
  • MeoMPyr-Br 58.98 g (0.263 mol) of MeoMPyr-Br is added to a round flask, and acetone and 34.67 g (0.315 mol) of NaBF 4 are added thereto, followed by stirring at room temperature for 12 hours. After the reaction was completed, the solvent was removed by distillation under reduced pressure to obtain 58.2 g of MeoMPyr-BF 4 .
  • MeoMPyr-Br 46.99 g (0.209 mol) of MeoMPyr-Br is added to a round flask, and 50 ml of CH 2 Cl 2 and 46.31 g (0.251 mol) of KPF 6 are added thereto, followed by stirring at room temperature for 12 hours. After the reaction was completed, the mixture was extracted and distilled under reduced pressure to obtain 57.6 g of MeoMPyr-PF 6 .
  • MeoMPip-Br 32.83 g (0.14 mol) of MeoMPip-Br is added to a round flask, distilled water is added, 47.48 g (0.17 mol) of LiTFSI is added, and the mixture is stirred at room temperature for 12 hours. After the reaction is completed, the mixture is extracted and the organic layer is removed by distillation under reduced pressure to obtain 58.8 g of MeoMPip-TFSI.
  • MeoMMor-Br in a round flask, add distilled water, add 46.94g (0.163 mol) of LiTFSI, and stir at room temperature for 12 hours. After the reaction was completed, the mixture was extracted, and the organic layer was removed by distillation under reduced pressure to obtain 58.8 g of MeoMMor-TFSI.
  • MeoMMor-Br 47.6 g (0.20 mol) of MeoMMor-Br is added to a round flask, and 50 ml of CH 2 Cl 2 and 44.15 g (0.24 mol) of KPF 6 are added thereto, followed by stirring at room temperature for 12 hours. After the reaction was completed, the solvent was distilled under reduced pressure to obtain 7.2 g of MeoMMor-PF 6 .
  • Triethyl-2- methoxyethanaminitetrafluoroborate (MeoTEA-BF 4 )
  • MeoMIM-Br 47.21 g (0.20 mol) of MeoMIM-Br is added to a round flask, and 50 ml of CH 2 Cl 2 and 43.42 g (0.24 mol) of KPF 6 are added thereto, followed by stirring at room temperature for 12 hours. After the reaction was completed, the mixture was extracted and distilled under reduced pressure to obtain 56.4 g of MeoTEA-PF 6 .

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Abstract

L'objectif de la présente invention est de fournir un liquide ionique comprenant un groupe éther au niveau d'un cation, les liquides ioniques, ayant un cation comprenant un groupe méthoxyéthyl éther à la méthylimidazolium, le méthylpyrrolidinium, le méthylpyridinium, le méthylmorpholinium et le triéthylammonium et ayant, en tant qu'anion, le tétrafluoroborate, hexafluorophosphate, le bisfluorosulfonylimide, et le bistrifluorométhanesulfonylimide, a une excellente stabilité thermique d'une moyenne TGA de 388 °C, une conductivité ionique de 40,0 mS/cm ou plus, et une fenêtre électrochimique de 5,1 V ou plus.
PCT/KR2016/008949 2016-08-12 2016-08-12 Procédé de préparation d'un liquide ionique électrolytique contenant un groupe éther et ayant une conductivité ionique élevée Ceased WO2018030564A1 (fr)

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KR1020197002698A KR102127081B1 (ko) 2016-08-12 2016-08-12 높은 이온전도도를 갖는 전해질용 이온성 액체 제조방법
PCT/KR2016/008949 WO2018030564A1 (fr) 2016-08-12 2016-08-12 Procédé de préparation d'un liquide ionique électrolytique contenant un groupe éther et ayant une conductivité ionique élevée

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PCT/KR2016/008949 WO2018030564A1 (fr) 2016-08-12 2016-08-12 Procédé de préparation d'un liquide ionique électrolytique contenant un groupe éther et ayant une conductivité ionique élevée

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109941978A (zh) * 2019-04-25 2019-06-28 浙江科峰锂电材料科技有限公司 制备双氟磺酰亚胺铵及双氟磺酰亚胺碱金属盐的方法
CN112898458A (zh) * 2021-01-15 2021-06-04 中国科学院兰州化学物理研究所 一种聚合离子液体及其制备方法和应用、超级电容器电解液
CN115295882A (zh) * 2022-08-29 2022-11-04 珠海中科先进技术研究院有限公司 一种锂离子电池电解液及其制备方法和应用

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KR20140076325A (ko) * 2012-12-12 2014-06-20 삼성정밀화학 주식회사 이온성 액체를 포함하는 고체 전해질
KR20160026644A (ko) * 2014-08-29 2016-03-09 삼성전자주식회사 복합체, 그 제조방법, 이를 포함하는 전해질 및 리튬이차전지

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2011012033A (ja) * 2009-07-06 2011-01-20 Sanyo Chem Ind Ltd イオン液体
JP2011236161A (ja) * 2010-05-11 2011-11-24 Mazda Motor Corp イオン液体およびその製造方法、並びに同イオン液体を用いた蓄電装置
KR20140046611A (ko) * 2012-10-08 2014-04-21 한양대학교 산학협력단 이온성 액체 고분자 전해질용 조성물, 이에 의해 제조된 이온성 액체 고분자 전해질 및 이를 포함하는 리튬이차전지
KR20140076325A (ko) * 2012-12-12 2014-06-20 삼성정밀화학 주식회사 이온성 액체를 포함하는 고체 전해질
KR20160026644A (ko) * 2014-08-29 2016-03-09 삼성전자주식회사 복합체, 그 제조방법, 이를 포함하는 전해질 및 리튬이차전지

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109941978A (zh) * 2019-04-25 2019-06-28 浙江科峰锂电材料科技有限公司 制备双氟磺酰亚胺铵及双氟磺酰亚胺碱金属盐的方法
CN112898458A (zh) * 2021-01-15 2021-06-04 中国科学院兰州化学物理研究所 一种聚合离子液体及其制备方法和应用、超级电容器电解液
CN112898458B (zh) * 2021-01-15 2022-01-07 中国科学院兰州化学物理研究所 一种聚合离子液体及其制备方法和应用、超级电容器电解液
CN115295882A (zh) * 2022-08-29 2022-11-04 珠海中科先进技术研究院有限公司 一种锂离子电池电解液及其制备方法和应用

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KR102127081B1 (ko) 2020-06-25

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