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Ube Industries : "High-Purity Vinylene Carbonate, Nonaqueous Electrolytic Solution, and Electricity Storage Device Including Same" in Patent Application Approval...

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06/22/2017 | 11:07pm CEST

"High-Purity Vinylene Carbonate, Nonaqueous Electrolytic Solution, and Electricity Storage Device Including Same" in Patent Application Approval Process (USPTO 20170162915)

By a News Reporter-Staff News Editor at Life Science Weekly -- A patent application by the inventors ABE, Koji (Sakai-shi, JP); ITO, Akikazu (Sakai-shi, JP); SHIKITA, Shoji (Sakai-shi, JP), filed on June 23, 2015, was made available online on June 15, 2017, according to news reporting originating from Washington, D.C., by NewsRx correspondents (see also Ube Industries, Ltd.).

This patent application is assigned to Ube Industries, Ltd.

The following quote was obtained by the news editors from the background information supplied by the inventors: "It is widely known that vinylene carbonate (hereinafter also referred to as 'VC') is useful as an additive for an electrolytic solution for lithium secondary batteries, and it is known that a high-purity VC having a low content of chlorine impurities is useful as an additive of electrolytic solutions (see PTLs 1, 4, and 5). As a purification method of VC, there are proposed various methods, such as distillation, crystallization, or a combined method of the both, etc. (see PTL 2). In addition, there is known a method in which a crude vinylene carbonate is treated with urea at 140.degree. C. and then distilled, followed by purification in a static melt crystallizer (see PTL 3).

"A conventional VC containing 100 ppm or more of chlorine impurities was colored brown to yellow. By controlling it such that the content of the chlorine impurities is 100 ppm or less, it became possible to make the VC transparent (see NPL 1)."

In addition to the background information obtained for this patent application, NewsRx journalists also obtained the inventors' summary information for this patent application: "Technical Problem

"The high-purity VC of PTL 1 is VC that is extremely less in impurities. Nevertheless, according to the Wickbold combustion-ion chromatography method, the content of chlorine impurities is not zero.

"According to the production method of high-purity VC of PTL 2, the production must be carried out by crystallization with a mixed solvent of toluene and hexane and further distillation, and thus, it is a batch type. Moreover, it may not be said that the production method of PTL 2 is useful as a method of reducing the content of chlorine impurities to substantially zero, and it has become clear that the production method of PTL 2 is not always said to be industrially an efficient method.

"In addition, according to the purification method of PTL 3, since the VC is exposed to high heat for a long period of time, during this, a reaction of a minute amount of chlorine, hydrogen chloride, etc. with VC occurs, too, resulting in not only a loss of VC but also formation of chlorine-containing by-products. When the resulting distillate is further purified by the static melt crystallizer, not only it is necessary to perform discontinuous switching of the operation between attachment and sweating of crystals, and no counter-current contact effect is brought. Thus, it has become clear that the purification method of PTL 3 is a purification method in which the impurities are hardly removed.

"In the working examples of PTL 4, though VC having a total chlorine amount of 14 ppm is described, VC having a total chlorine amount of less than 14 ppm is not specifically corroborated.

"In PTL 5, a nonaqueous electrolytic solution containing VC having a content of a specified chlorine compound of 10 ppm or less is described.

"In the working examples of PTL 5, the detection of an ether group containing a chlorine atom, which is represented by a specified general formula (1), is performed by gas chromatography. For that reason, the content of chlorine impurities cannot be quantitatively determined unless a detection peak of each of the ether compounds is specified. Although PTL 5 describes that the content of chlorine-containing vinyl ether-based impurities was reduced, it does not describe at all the reduction of the content of other chlorine impurities that are not a vinyl ether-based material. If only a distillation operation described in PTL 5 is performed, it is impossible to remove all of various chlorine-substituted compounds and a chlorine ion. Moreover, according to the gas chromatography, only a part of chlorine impurities can be detected. From the foregoing matters, it may be considered that when the chlorine impurities of vinylene carbonate obtained in the working examples of PTL 1 are measured by the Wickbold combustion-ion chromatography method, the content of the chlorine impurities becomes about several 10 ppm.

"In the light of the above, in the aforementioned PTLs 1 to 5, it is merely disclosed that the content of chlorine impurities as the impurities is reduced to a low concentration, and VC in which the content of chlorine impurities is highly reduced to zero has not been known. As a matter of course, these PTLs 1 to 5 neither describe nor suggest their battery performances, and thus, there was no way to know the battery performances of VC having the content of chlorine impurities of zero.

"A problem of the present invention is to provide a high-purity VC in which the content of chlorine impurities is reduced to zero, in other words, a high-purity VC that does not substantially contain impurities at all, a nonaqueous electrolytic solution containing the foregoing high-purity VC, and an energy storage device using the same.

"Solution to Problem

"In order to solve the aforementioned problem, the present inventors made extensive and intensive investigations. As a result, they have successfully reduced the content of chlorine impurities in VC to substantially zero and found that a special phenomenon takes place thereby.

"The present inventors have found that as a simple and easy industrial method of reducing the content of chlorine impurities in VC ultimately, such VC can be produced on an industrial scale through crystallization accompanied by solid-liquid counter-current contact, leading to accomplishment of the present invention. The high-purity VC obtained by the foregoing production method, in which the content of chlorine impurities is reduced to zero is a colorless, transparent liquid in a nitrogen atmosphere similar to a conventional VC containing chlorine impurities in an amount of about 100 ppm or less and 10 ppm or more; however, the present inventors have found a peculiar phenomenon in which when exposed in air, the high-purity VC takes on a yellow-green color in terms of the Munsell color system (see FIG. 2).

"In the production method of an electrolytic solution for lithium ion batteries, which is classified into Class I petroleums or Class II petroleums, there is a concern of ignition or contamination by water. Therefore, in general, commonsensically, such an electrolytic solution is not exposed in an oxygen-containing atmosphere (for example, in air, etc.), so that it was difficult to discover this phenomenon. Moreover, in a conventional VC containing chlorine impurities in an amount of about 100 ppm or less and 10 ppm or more, even when exposed in an oxygen-containing atmosphere, the foregoing VC was still colorless and transparent and did not take on a yellow-green color.

"The present inventors have found that in an energy storage device, such as a lithium secondary battery using a nonaqueous electrolytic solution containing a high-purity VC that when exposed in this oxygen-containing atmosphere, takes on a yellow-green color, etc., an output property at a low temperature and a cycle property over an extremely long period of time are improved.

"Specifically, the present invention provides the following [1] to [13]. [1] A high-purity vinylene carbonate (hereinafter also referred to as 'high-purity VC') that is VC having the content of chlorine impurities of zero as detected by the Wickbold combustion-ion chromatography method and having a Hazen unit color number (hereinafter referred to as 'APHA') in a nitrogen atmosphere of 10 or less. [2] The high-purity VC as set forth above in [1], wherein when stored at 45.degree. C. for 7 days in an oxygen-containing atmosphere, the VC has an APHA of 100 or more. [3] The high-purity VC as set forth above in [1], wherein when stored at 45.degree. C. for 7 days in an oxygen-containing atmosphere, the VC takes on a yellow-green color in a range of from 10Y to 10GY in terms of a hue circle of the Munsell color system. [4] The high-purity VC as set forth above in [1], wherein a melting point at atmospheric pressure is 20.degree. C. or higher and lower than 22.degree. C. [5] The high-purity VC as set forth above in [1], wherein the chlorine impurities as detected by the Wickbold combustion-ion chromatography method are calculated as converted into a chlorine atom in a manner that a sample is dissolved in a solvent and subjected to oxyhydrogen flame combustion treatment, an obtained gas is absorbed in a sodium carbonate aqueous solution, and a chlorine ion in the absorption solution is measured by ion chromatography. [6] A method for producing the high-purity VC as set forth above in [1], wherein the vinylene carbonate is produced by a method including the following steps (A) to (C):

"(A) a step of scraping crude VC crystals crystallized in a crystallization tank by using a scraper and precipitating the VC crystals in a bottom of a melt purification tower;

"(B) a step of bringing the precipitated VC crystals and a part of the VC molten liquid melted in the bottom of the melt purification tower into counter-current contact with each other; and

"(C) a step of extracting a part of the VC molten liquid from the bottom of the melt purification tower. [7] A nonaqueous electrolytic solution having an electrolyte salt dissolved in a nonaqueous solvent, the nonaqueous electrolytic solution including the high-purity VC as set forth above in [1]. [8] The nonaqueous electrolytic solution as set forth above in [7], including 0.1 to 1.5 mass % of LiPO.sub.2F.sub.2 in the nonaqueous electrolytic solution. [9] The nonaqueous electrolytic solution as set forth above in [7], including 1 to 50 ppm of HF in the nonaqueous electrolytic solution. [10] The nonaqueous electrolytic solution as set forth above in [7], wherein a ratio in concentration between LiPO.sub.2F.sub.2 and HF ((HF concentration)/(LiPO.sub.2F.sub.2 amount) in the nonaqueous electrolytic solution is 1/15,000 to 1/20. [11] An energy storage device including a positive electrode, a negative electrode, and a nonaqueous electrolytic solution having an electrolyte salt dissolved in a nonaqueous solvent, wherein the nonaqueous electrolytic solution is the nonaqueous electrolytic solution as set forth above in any of [7] to [10]. [12] A method for producing the high-purity VC as set forth above in [1] to [5], including bringing crude VC crystals containing chlorine impurities and a part of a molten liquid of the crude VC into solid-liquid counter-current contact with each other. [13] The method for producing the high-purity VC as set forth above in [12], including the following steps (A) to (C):

"(A) a step of scraping crude VC crystals crystallized in a crystallization tank by using a scraper and precipitating the VC crystals in a bottom of a melt purification tower;

"(B) a step of bringing the precipitated VC crystals and a part of the VC molten liquid melted in the bottom of the melt purification tower into counter-current contact with each other; and

"(C) a step of extracting a part of the VC molten liquid from the bottom of the melt purification tower.

"Advantageous Effects of Invention

"In accordance with the present invention, it is possible to provide a high-purity VC that is entirely free from chlorine impurities as defected by the Wickbold combustion-ion chromatography method, a nonaqueous electrolytic solution containing the foregoing high-purity VC, and an energy storage device using the same.

"The energy storage device using the nonaqueous electrolytic solution containing a high-purity VC of the present invention is able to improve an output property at a low temperature and a cycle property over a long period of time. In particular, with respect to the cycle property, a high discharge capacity can be maintained over an extremely long period of time, thereby enabling a life of the energy storage device to be significantly extended, and therefore, the energy storage device of the present invention has an energy saving effect.

"As for the evaluation of the cycle property, though the evaluation has hitherto been performed in terms of cycles of about 50 to 100 cycles, the energy storage device using the nonaqueous electrolytic solution containing a high-purity VC of the present invention exhibits an excellent effect even in the evaluation of a cycle property over an extremely long period of time as 1,000 cycles, the evaluation of which has not hitherto been performed."

URL and more information on this patent application, see: ABE, Koji; ITO, Akikazu; SHIKITA, Shoji. High-Purity Vinylene Carbonate, Nonaqueous Electrolytic Solution, and Electricity Storage Device Including Same. Filed June 23, 2015 and posted June 15, 2017. Patent URL: http://appft.uspto.gov/netacgi/nph-Parser?Sect1=PTO1&Sect2=HITOFF&d=PG01&p=1&u=%2Fnetahtml%2FPTO%2Fsrchnum.html&r=1&f=G&l=50&s1=%2220170162915%22.PGNR.&OS=DN/20170162915&RS=DN/20170162915

Keywords for this news article include: Anions, Alkalies, Chlorine, Halogens, Carbonates, Chalcogens, Carbonic Acid, Ube Industries Ltd.

Our reports deliver fact-based news of research and discoveries from around the world. Copyright 2017, NewsRx LLC

(c) 2017 NewsRx LLC, source Health Newsletters

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Sales 2018 680 650 M
EBIT 2018 -
Net income 2018 24 514 M
Debt 2018 143 350 M
Yield 2018 2,11%
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P/E ratio 2019 10,29
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