JP5055536B2 - Highly immobilized carbon dioxide - Google Patents
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- 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
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- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
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Description
本発明は、新規な二酸化炭素の高度固定化物に関し、詳しくは電気化学電池に使用されるカーボネート誘導体である二酸化炭素の高度固定化物に関する。 The present invention relates to a novel highly immobilized product of carbon dioxide, and more particularly to a highly immobilized product of carbon dioxide, which is a carbonate derivative used in electrochemical cells.
カーボネート類は、リチウムイオン電池用電解質、電気二重層キャパシタ用電解質、アルカリ金属電気化学電池用電解質などに利用されている化合物群である。 Carbonates are a group of compounds that are used in electrolytes for lithium ion batteries, electrolytes for electric double layer capacitors, electrolytes for alkali metal electrochemical cells, and the like.
これまでその電気化学的な機能を高めるために、環状カーボネート官能基を有するポリマーが提案されたり（特許文献１）、新規なグリセリンジカーボネートが提案されたり（特許文献２）、環状カーバメート等が提案されている（特許文献３）。
しかし、電解質は衝撃を与えるとしばしば発火するなど問題があるものの、積極的に安全性の対策がなされてこなかった。 However, although electrolytes often ignite when impacted, no safety measures have been actively taken.
本発明者は、電解質の電気化学機能に、難燃性の機能を付加した新たなカーボネート類を開発し、安全性に寄与することを見出し、本発明に至った。 The inventor of the present invention has developed new carbonates in which a flame retardant function is added to the electrochemical function of the electrolyte, and has found that it contributes to safety, and has led to the present invention.
本発明の課題は、電気化学機能に、難燃性の機能を付加した新たなカーボネート類を提供することにある。 The subject of this invention is providing the new carbonate which added the flame retardance function to the electrochemical function.
本発明者は、電気化学機能に、難燃性の機能を付加した新たなカーボネート類を開発に鋭意研究の結果、電気化学電池に使用されるカーボネート誘導体の多くが、二酸化炭素が固定された形の分子構造であることに注目し、分子中に二酸化炭素由来の部分ができるだけ多いカーボネート類を開発した。これらは熱分解時に二酸化炭素が発生し、自己消火型の難燃性の機能が付加された材料である。 As a result of earnest research on the development of new carbonates having a flame retardant function in addition to the electrochemical function, the present inventor has found that most of the carbonate derivatives used in electrochemical cells have carbon dioxide fixed. In particular, we have developed carbonates with as many carbon dioxide-derived moieties as possible in the molecule. These carbon dioxide generated during pyrolysis, is a material function is added for flame retardancy of a self-extinguishing type.
即ち、上記課題は、以下の各発明によって解決される。 That is, the said subject is solved by each following invention.
(請求項１)
下記一般式（１）で表されることを特徴とする二酸化炭素の高度固定化物。
〔式中、Aは酸素原子またはNHを表す。〕
(Claim 1)
A highly immobilized product of carbon dioxide, which is represented by the following general formula (1).
[Wherein, A represents an oxygen atom or NH. ]
（請求項２）
下記一般式（２）で表されることを特徴とする二酸化炭素の高度固定化物。
〔式中、Aは酸素原子またはNHを表す。〕
(Claim 2)
A highly immobilized product of carbon dioxide, which is represented by the following general formula (2).
[Wherein, A represents an oxygen atom or NH. ]
（請求項３）
下記一般式（３）で表されることを特徴とする二酸化炭素の高度固定化物。
〔式中、Aは酸素原子またはNHを表す。〕
(Claim 3)
A highly immobilized product of carbon dioxide, which is represented by the following general formula (3).
[Wherein, A represents an oxygen atom or NH. ]
本発明によると、電気化学機能に、難燃性の機能を付加した新たな二酸化炭素の高度固定化物を提供できる。 ADVANTAGE OF THE INVENTION According to this invention, the highly fixed thing of the new carbon dioxide which added the flame retardance function to the electrochemical function can be provided.
本発明は、新規な二酸化炭素の高度固定化物を提供するものであり、その構造式は、上記一般式（１）、（２）又は（３）で表される。これらは熱分解時に二酸化炭素が発生し、自己消火型の難燃性の機能が付加された材料となるので、本発明の新規化合物は、電気化学機能に、難燃性の機能が付加されたものである。 The present invention provides a novel highly-immobilized product of carbon dioxide, whose structural formula is represented by the above general formula (1), (2) or (3). These carbon dioxide generated during pyrolysis, since the function of the flame retardancy of a self-extinguishing type is added to the material, the novel compounds of the present invention, the electrochemical function, is added function of the flame retardant It is a thing.
本発明に係る一般式（１）、（２）又は（３）で表される二酸化炭素の高度固定化物は、該化合物の分子量のうち二酸化炭素由来の部分が５０％を超えることが好ましい。分子量のうち二酸化炭素由来の部分が５０％を超えると、電気化学機能に、難燃性の機能がより高度に付加されたものとなり好ましい。 In the highly immobilized product of carbon dioxide represented by the general formula (1), (2) or (3) according to the present invention, the carbon dioxide-derived part of the molecular weight of the compound preferably exceeds 50%. When the carbon dioxide-derived portion of the molecular weight exceeds 50%, it is preferable that the flame retardance function is added to the electrochemical function to a higher degree.
本発明の一般式（１）で示す化合物であるトリカーボネート〔(式中、Aはすべて酸素原子（O）)は、下記化７で示す式のようにグリシドールとエピクロロヒドリンから、塩基(例えば炭酸カリウム)およびオニウム塩(例えばテトラブチルアンモニウムブロマイド)存在下で、超臨界二酸化炭素で処理することにより、合計３分子の二酸化炭素を固定してワンポットで得ることができる。 Tricarbonate which is a compound represented by the general formula (1) of the present invention [wherein A is all oxygen atoms (O)] is obtained from glycidol and epichlorohydrin as shown in the following formula (7). For example, by treating with supercritical carbon dioxide in the presence of potassium carbonate) and onium salt (for example, tetrabutylammonium bromide), a total of three molecules of carbon dioxide can be fixed and obtained in one pot.
この反応は段階的に行うことができ、環状カーボネートのアルコールと環状カーボネートの塩化物とを入手後、上記と同様に反応しても得られる。 This reaction can be carried out stepwise, and can also be obtained by reacting in the same manner as described above after obtaining the cyclic carbonate alcohol and the cyclic carbonate chloride.
環状カーボネートの塩化物単独でも、上記の反応条件をやや厳しくすることでトリカーボネートを得ることができる。 Even with a cyclic carbonate chloride alone, tricarbonate can be obtained by slightly tightening the above reaction conditions.
環状カーボネートのアルコールは、ホスゲンやトリホスゲンのようなホスゲン等価体と、ピリジン中で処理してもトリカーボネートを得ることができる。 Tricarbonate can be obtained by treating a cyclic carbonate alcohol with a phosgene equivalent such as phosgene or triphosgene in pyridine.
環状カーボネート誘導体の代わりに環状ウレタンのアルコールやハライドを用いて同様な反応を行うと、環状ウレタンカーボネートが得られる。 When a similar reaction is carried out using alcohol or halide of cyclic urethane instead of the cyclic carbonate derivative, cyclic urethane carbonate is obtained.
環状カーボネートや環状ウレタンのアミンを原料に用いるとウレタン結合や尿素結合で環状化合物を連結した化合物が得られる。 When a cyclic carbonate or cyclic urethane amine is used as a raw material, a compound in which a cyclic compound is linked by a urethane bond or a urea bond is obtained.
上記一般式（１）、（２）又は（３）で示される化合物の例示化合物は、式中のAに、酸素原子またはNHを導入したものが挙げられる。 Examples of the compound represented by the general formula (1), (2) or (3) include those in which an oxygen atom or NH is introduced into A in the formula.
以下、本発明の実施例について説明するが、かかる実施例によって本発明が限定されるものではない。 Examples of the present invention will be described below, but the present invention is not limited to these examples.
（実施例1）
50mlステンレス製オートクレーブに、炭酸カリウム(1.385 g)とテトラブチルアンモニウムブロマイド(0.081 g)を秤量瓶で測りとったもの、グリシドール(0.38 g)、エピクロロヒドリン(0.75 g)およびDMSO(0.8 g)の順に加え、室温で液化二酸化炭素(13.5 g)を導入し、100℃に加熱すると超臨界状態(7.4 MPa)となり１時間撹拌反応させた。
(Example 1)
In a 50 ml stainless steel autoclave, potassium carbonate (1.385 g) and tetrabutylammonium bromide (0.081 g) measured with a weighing bottle, glycidol (0.38 g), epichlorohydrin (0.75 g) and DMSO (0.8 g) In this order, liquefied carbon dioxide (13.5 g) was introduced at room temperature, and when heated to 100 ° C., the mixture became supercritical (7.4 MPa) and allowed to react for 1 hour.
反応後、反応容器を氷冷し減圧した後容器を開け、アセトニトリルで生成物を抽出し、無機化合物をろ過で除いた。ろ液を濃縮すると、下記構造式のトリカーボネートが1.15 g得られた。 After the reaction, the reaction vessel was ice-cooled and decompressed, then the vessel was opened, the product was extracted with acetonitrile, and the inorganic compound was removed by filtration. When the filtrate was concentrated, 1.15 g of tricarbonate having the following structural formula was obtained.
アセトニトリルから再結晶するとmp155.5-157.0℃の無色の結晶が得られた。IR (KBr) 1760,1792cm2; 1H-NMR (400 MHz, DMSO) δ=4.28〜4.32 (2H, m), 4.36 (2H, ddd, J=12.2, 5.2, 0.8 Hz), 4.41 (2H, ddd, J=12.2, 2.8, 0.8 Hz), 4.58 (2H, t, J=8.8 Hz), 5.04〜5.09 (2H, m); 13C-NMR (100 Hz, DMSO) δ=65.7, 67.2, 74.0, 153.8, 154.8. Recrystallization from acetonitrile gave colorless crystals of mp155.5-157.0 ° C. IR (KBr) 1760,1792cm 2 ; 1 H-NMR (400 MHz, DMSO) δ = 4.28 ~ 4.32 (2H, m), 4.36 (2H, ddd, J = 12.2, 5.2, 0.8 Hz), 4.41 (2H, ddd, J = 12.2, 2.8, 0.8 Hz), 4.58 (2H, t, J = 8.8 Hz), 5.04 to 5.09 (2H, m); 13 C-NMR (100 Hz, DMSO) δ = 65.7, 67.2, 74.0 , 153.8, 154.8.
（実施例２）
100mlステンレス製オートクレーブに、炭酸カリウム(4.13 g)とテトラブチルアンモニウムブロマイド(0.024 g)、4-ヒドロキシメチル-1,3-ジオキソラン-2-オン(1.77 g)、4-クロロメチル-1,3-ジオキソラン-2-オン(3.0 g)および液化二酸化炭素を加え90℃に加熱し、9 MPaで2時間撹拌反応した。反応後、実施例１と同様に処理し、実施例１と同一の構造式のトリカーボネートが3.03 g得られた。
(Example 2)
To a 100 ml stainless steel autoclave, potassium carbonate (4.13 g) and tetrabutylammonium bromide (0.024 g), 4-hydroxymethyl-1,3-dioxolan-2-one (1.77 g), 4-chloromethyl-1,3- Dioxolan-2-one (3.0 g) and liquefied carbon dioxide were added, and the mixture was heated to 90 ° C. and stirred at 9 MPa for 2 hours. After the reaction, the same treatment as in Example 1 was performed to obtain 3.03 g of tricarbonate having the same structural formula as in Example 1.
（実施例３）
30 mlフラスコに4-ヒドロキシメチル-1,3-ジオキソラン-2-オン(0.59 g)を加え乾燥ピリジン(5 ml)で溶解する。フラスコを冷却しながらトリホスゲン(1.48 g)を徐々に加え、室温で1時間撹拌反応する。反応後、析出した塩酸塩をろ別し、ろ液を濃縮すると、実施例１と同一の構造式のトリカーボネートが0.61 g得られた。
(Example 3)
Add 4-hydroxymethyl-1,3-dioxolan-2-one (0.59 g) to a 30 ml flask and dissolve with dry pyridine (5 ml). While the flask is cooled, triphosgene (1.48 g) is gradually added, and the mixture is stirred at room temperature for 1 hour. After the reaction, the precipitated hydrochloride was filtered off and the filtrate was concentrated to obtain 0.61 g of tricarbonate having the same structural formula as in Example 1.
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| TWI385838B (en) * | 2009-06-15 | 2013-02-11 | Taiwan Hopax Chems Mfg Co Ltd | Electrolyte for electrochemical device and the electrochemical device thereof |
| CN101931107B (en) * | 2009-06-24 | 2012-10-10 | 聚和国际股份有限公司 | Electrolyte for electrochemical device and electrochemical device |
| FR2952933B1 (en) * | 2009-11-20 | 2012-05-25 | Centre Nat Rech Scient | BISCARBONATE PRECURSORS, PROCESS FOR PREPARING THEM AND USES THEREOF |
| JP5936375B2 (en) * | 2012-02-02 | 2016-06-22 | 大阪瓦斯株式会社 | Flame retardant composition and polycarbonate resin composition |
| JP5851350B2 (en) * | 2012-06-04 | 2016-02-03 | 大阪瓦斯株式会社 | Carbon dioxide purification method |
| CN107591557B (en) * | 2016-07-08 | 2019-05-21 | 深圳新宙邦科技股份有限公司 | A kind of non-aqueous electrolyte for lithium ion cell and the lithium ion battery using the electrolyte |
| JP6402238B2 (en) * | 2016-12-27 | 2018-10-10 | 花王株式会社 | Method for producing glyceric acid ester |
| WO2018124148A1 (en) * | 2016-12-27 | 2018-07-05 | 花王株式会社 | Method for producing glyceric acid ester |
| JP6402239B2 (en) * | 2016-12-27 | 2018-10-10 | 花王株式会社 | Method for producing glyceric acid ester |
| WO2018124147A1 (en) | 2016-12-27 | 2018-07-05 | 花王株式会社 | Method for manufacturing 1,3-dioxane-5-one |
| JP6393396B2 (en) * | 2016-12-27 | 2018-09-19 | 花王株式会社 | Method for producing glyceric acid ester |
| US10829482B2 (en) | 2016-12-27 | 2020-11-10 | Kao Corporation | Method for producing glyceric acid ester |
| CN108808086B (en) | 2017-04-28 | 2020-03-27 | 深圳新宙邦科技股份有限公司 | Lithium ion battery non-aqueous electrolyte and lithium ion battery |
| CN108808065B (en) * | 2017-04-28 | 2020-03-27 | 深圳新宙邦科技股份有限公司 | Lithium ion battery non-aqueous electrolyte and lithium ion battery |
| CN108808084B (en) | 2017-04-28 | 2020-05-08 | 深圳新宙邦科技股份有限公司 | Lithium ion battery non-aqueous electrolyte and lithium ion battery |
| CN108808066B (en) * | 2017-04-28 | 2020-04-21 | 深圳新宙邦科技股份有限公司 | Lithium ion battery non-aqueous electrolyte and lithium ion battery |
| CN108933292B (en) | 2017-05-27 | 2020-04-21 | 深圳新宙邦科技股份有限公司 | Lithium ion battery non-aqueous electrolyte and lithium ion battery |
| CN109326824B (en) | 2017-07-31 | 2020-04-21 | 深圳新宙邦科技股份有限公司 | Lithium ion battery non-aqueous electrolyte and lithium ion battery |
| CN109326823B (en) | 2017-07-31 | 2020-04-21 | 深圳新宙邦科技股份有限公司 | Lithium ion battery non-aqueous electrolyte and lithium ion battery |
| CN109950621B (en) * | 2017-12-21 | 2022-05-03 | 深圳新宙邦科技股份有限公司 | Lithium ion battery non-aqueous electrolyte and lithium ion battery |
| CN109994776B (en) * | 2017-12-29 | 2022-05-03 | 深圳新宙邦科技股份有限公司 | Lithium ion battery non-aqueous electrolyte and lithium ion battery |
| CN109994779A (en) * | 2017-12-29 | 2019-07-09 | 深圳新宙邦科技股份有限公司 | A kind of non-aqueous electrolyte for lithium ion cell and lithium ion battery |
| CN110444804B (en) * | 2018-05-04 | 2021-02-12 | 深圳新宙邦科技股份有限公司 | Lithium ion battery non-aqueous electrolyte and lithium ion battery |
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| JP2002175837A (en) * | 2000-12-06 | 2002-06-21 | Nisshinbo Ind Inc | Polymer gel electrolyte and secondary battery, and electric double-layer capacitor |
| US6602976B2 (en) * | 2001-05-05 | 2003-08-05 | Lithdyne International | Polycarbonate oligomers and polymers for use in electrolytes |
| JP2003040885A (en) * | 2001-07-27 | 2003-02-13 | Toyota Motor Corp | Glycerol dicarbonate derivative, non-aqueous electrolyte solution produced by using the same, polymer electrolyte and cell |
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