JP4220619B2 - Method for producing indene carbonate - Google Patents
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- JP4220619B2 JP4220619B2 JP19570599A JP19570599A JP4220619B2 JP 4220619 B2 JP4220619 B2 JP 4220619B2 JP 19570599 A JP19570599 A JP 19570599A JP 19570599 A JP19570599 A JP 19570599A JP 4220619 B2 JP4220619 B2 JP 4220619B2
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Description
【０００１】
【発明の属する技術分野】
本発明は、樹脂原料や化学品中間体として有用である炭酸インデンの製造方法に関し、更に詳しくはアルキルインダンジオール、ハロゲン化インダノールなどを原料とし、アミン類の炭酸塩、無機炭酸塩、炭酸塩型陰イオン交換樹脂または炭酸ガスと反応させる炭酸インデンの製造方法に関する。
【０００２】
【従来の技術】
従来の炭酸インデンの製造方法としては、インデンから１，２−インダンジオールを合成した後、１，１’−カルボニルジイミダゾールを作用させて炭酸インデンを製造する方法（R.C.White,P.Drew and R.Moorman,J.Heterocycl.Chem,25,1781(1988)）、また、１，２−インダンジオールにホスゲンを作用させて炭酸インデンを製造する方法（R.A.Austin and C.P.Lillya,J.Org.Chem,34(5),1327(1969)）などが一般的に知られている。
【０００３】
【発明が解決しようとする課題】
しかしながら、上記従来方法は、高価な原料を使用する、あるいは毒性の強い原料を必要とするなど、工業的な量産プロセスへの適用には問題がある。従って本発明の目的は、安価で危険性の少ない原料を使用して、量産プロセスにも適用できる炭酸インデンの製造方法を提供することである。
【０００４】
【課題を解決するための手段】
上記目的は以下の本発明によって達成される。即ち、本発明は、下記一般式（１）
【０００５】
本発明者らは、インダンジオールまたはハロゲン化インダノール、あるいはそれらのアルキル置換化合物と炭酸塩とを反応させるか、好ましくは炭酸雰囲気において炭酸塩と反応させることにより、簡便に炭酸インデンを製造できることを発見した。尚、本発明においては「炭酸塩」とは重炭酸塩も含む意味で使用されている。
【０００６】
【発明の実施の形態】
次に好ましい実施の形態を挙げて本発明を更に詳細に説明する。
本発明において原料として使用する前記一般式（１）で表わされる化合物としては、例えば、５−メチル−１，２−インダンジオール、４−エチル−１，２−インダンジオールなどのインダンジオール類、２−クロロ−１−インダノール、２−ブロモ−５−エチル−１−インダノール、１−クロロ−５−メチル−２−インダノール、１−ブロモ−２−インダノールのようなハロゲン化インダノールが挙げられる。これらの原料の純度は、特に限定されず、高純度のものでも低純度のものでも構わないが、不純物は反応に不活性な化合物であることが好ましい。反応に活性な不純物であっても、反応に対する影響が僅かであるなら、特に含まれていても本発明を実施する上で何ら差し支えない。
【０００７】
本発明で反応に使用する炭酸塩としては、例えば、メチルアミン、エチルアミン、ジエチルアミン、トリエチルアミン、エチレンジアミン、ベンジルトリメチルアンモニウム、テトラエチルアンモニウム、ピリジン、キノリンなどのアミン類の炭酸塩もしくは重炭酸塩、ジエチルアミノエチル基、トリメチルアミノメチル基などのイオン交換基を有する炭酸塩または重炭酸塩型の陰イオン交換樹脂、あるいは炭酸ナトリウム、炭酸カリウム、炭酸マグネシウム、炭酸カルシウム、ハイドロタルサイトのような無機炭酸塩が挙げられる。これらの中では、特に上記のアミン類の炭酸塩もしくは重炭酸塩が好ましい。
【０００８】
反応に際しては反応原料をそのまま混合してもよいが、反応原料、特に炭酸塩を均一に分散させるために反応に際しては溶媒を使用することが望ましい。溶媒としては、水や、アセトニトリル、メタノールなどの極性溶媒、トルエン、ベンゼンなどの無極性溶媒が挙げられる。溶媒は単体でも２種類の混合溶液でもよく、混合溶媒の場合にはその１成分が水でもよい。本発明において、反応温度は−１０〜１５０℃、好ましくは２０〜８０℃の範囲である。反応は大気圧下で行うことができる。必要に応じて加圧してもよい。
【０００９】
反応は、場合によっては溶媒を使用して原料及び炭酸塩を混合し、所定の反応温度に保ちながら攪拌することで進行するが、反応時間を短縮し、炭酸インデンへの選択性を高めるために、反応溶液中に、例えば、炭酸ガスをバブリングするなどして反応を炭酸雰囲気に保って行なうことが望ましい。使用する炭酸ガスの量は反応系を炭酸ガス雰囲気に維持できる量であればよい。また、炭酸ガスの純度は特に限定されないが、不純物は反応に不活性な化合物であることが好ましい。
【００１０】
本発明の方法における炭酸塩の使用量は、反応系を炭酸雰囲気に維持しない場合には、前記一般式（１）で表わされる原料のモル数に対して１〜２０倍モル、好ましくは１〜２倍モルである。一方、反応系を炭酸雰囲気に維持して反応を行なう場合には、炭酸塩の使用量は前記一般式（１）で表わされる原料のモル数に対して０．１〜２０倍モル、好ましくは０．５〜２倍モルである。この場合には反応によって消費された炭酸イオンは、反応雰囲気を維持している炭酸ガスによって補填されるので、炭酸塩は触媒的作用を有し、１倍モル以下でも反応は進行する。炭酸塩の使用量が１倍モル（炭酸雰囲気でない場合）あるいは０．１倍モル（炭酸雰囲気の場合）よりも少ないと、反応が著しく遅くなってしまう。また、使用量が２０倍モルより多くても、反応速度は大幅には改善されず、経済的ではない。これら炭酸塩は、別途調製して反応系に添加してもよいし、アミンや陰イオン交換樹脂に炭酸ガスを吹き込んで系内で発生させてもよい。
【００１１】
本発明の方法により生成した炭酸インデンは、反応後の反応液中に炭酸塩等の固体が懸濁している場合はそれらの固体を濾過分離後、濾液中の溶媒を留去することで得られる。また、反応後の反応液中に炭酸塩または他の無機物が溶解している場合は、適当な有機溶剤で炭酸インデンを抽出し、この溶剤を留去することで目的とする炭酸インデンが得られる。さらに純度の高い炭酸インデン製品は、適当な有機溶媒から再結晶を行うなどの通常の精製方法により容易に得ることができる。
【００１２】
【実施例】
次に実施例を挙げて本発明をさらに具体的に説明する。
実施例１
コンデンサー、温度計、ガス吹き込み管を備えた３００ｍｌ容の三つ口フラスコに、trans−２−ブロモ−１−インダノール８．０ｇ（０．０３７６ｍｏｌ）、ベンジルトリメチルアンモニウム炭酸塩１１．９ｇ（０．０５６３ｍｏｌ）およびアセトニトリル２００ｇを入れて混合した。この反応溶液を５０℃に保ちながら、炭酸ガスを１時間吹き込んだ。反応終了後、溶液を放冷して室温に戻した後、懸濁している固体を濾過分離した。濾液からアセトニトリルを留去した後、トルエン１００ｇを加えた。固体を濾過分離し、濾液からトルエンを留去し、炭酸インデンを晶出させた。これにより結晶性生成物５．８０ｇを得た。ＧＣ分析より、この生成物は純度９５重量％であった。
【００１３】
実施例２
実施例１と同じ反応器に、trans−２−ブロモ−１−インダノール８．０ｇ（０．０３７６ｍｏｌ）、ベンジルトリメチルアンモニウム炭酸塩１１．９ｇ（０．０５６３ｍｏｌ）およびトルエン２００ｇを入れ、混合した。この反応溶液を５０℃に保ちながら、炭酸ガスを６時間吹き込んだ。反応終了後、溶液を放冷して室温に戻した後、懸濁している固体を濾過分離した。濾液からトルエンを留去し、炭酸インデンを晶出させた。これにより結晶性生成物５．８３ｇを得た。ＧＣ分析により純度９７．６重量％であった。
【００１４】
実施例３
実施例１と同じ反応器に、trans−２−ブロモ−１−インダノール４．０ｇ（０．０１８８ｍｏｌ）、塩基性炭酸マグネシウム（重質）２０．０ｇ（０．２３８ｍｏｌ）およびアセトニトリル１００ｇを入れ、混合した。この反応溶液を５０℃に保ちながら、炭酸ガスを６時間吹き込んだ。反応終了後、溶液を放冷して室温に戻した後、懸濁している固体を濾過分離した。濾液からアセトニトリルを留去し、炭酸インデンを晶出させた。これにより結晶性生成物１．９０ｇを得た。ＧＣ分析により純度は９５．２重量％であった。
【００１５】
実施例４
実施例１と同じ反応器に、trans−２−ブロモ−１−インダノール８．０ｇ（０．０３７６ｍｏｌ）、陰イオン交換樹脂（炭酸型）８．０ｇおよびアセトニトリル２００ｇを入れ、混合する。この反応溶液を５０℃に保ちながら、炭酸ガスを８時間吹き込んだ。反応終了後、溶液を放冷して室温に戻した後、沈殿している固体を濾過分離した。濾液からアセトニトリルを留去し、炭酸インデンを晶出させた。これにより結晶性生成物３．７６ｇを得た。ＧＣ分析により純度は９３重量％であった。
【００１６】
実施例５
実施例１と同じ反応器に、１０．１重量％トリエチルアミン水溶液５０ｇを入れ、２５℃に保ちながら炭酸ガスを１時間吹き込んでアミンの炭酸塩を生成させた。反応後、trans−２−ブロモ−１−インダノール７．１ｇ（０．０３３３ｍｏｌ）、アセトニトリル１７７ｇを加え、５０℃に保ち、炭酸ガスをさらに２時間吹き込んだ。反応終了後、溶液を室温まで放冷した後、トルエン１００ｇを加えて、炭酸インデンを抽出した。分液後、有機層からエバポレーションにより溶媒を除去した。これにより結晶性生成物４．９８ｇを得た。ＧＣ分析により純度９４．６重量％であった。
【００１７】
実施例６
実施例５と同じ反応器に、１０．１重量％トリエチルアミン水溶液５０ｇを入れ、２５℃に保ちながら炭酸ガスを１時間吹き込んでアミンの炭酸塩を生成させた。反応後、trans−２−ブロモ−１−インダノール７．１ｇ（０．０３３３ｍｏｌ）、アセトニトリル１７７ｇを加え、５０℃に保ち、炭酸ガスをさらに２時間吹き込んだ。反応終了後、溶液を室温まで放冷した後、溶媒を留去した。さらに、残った化合物を室温で真空乾燥し、結晶性生成物５．２０ｇを得た。純度はＧＣ分析により９７．３重量％であった。
【００２０】
実施例７
コンデンサー、温度計、ガス吹き込み管を備えた２００ｍｌ容の三つ口フラスコに１０．１重量％トリエチルアミン水溶液３３．３ｇを入れ、２５℃に保ちながら炭酸ガスを１時間吹き込んでアミンの炭酸塩を生成させた。反応後、trans−２−ブロモ−１−インダノール４．７３ｇ（０．０２２２ｍｏｌ）、アセトニトリル１１０ｇを加え、５０℃に保ちながら攪拌した。そのまま６時間反応を行った。反応終了後、溶液を室温まで放冷した後、溶媒を留去した。さらに残った化合物を室温で真空乾燥し、結晶性生成物４．０５ｇを得た。ＧＣ分析の結果、純度は７５．６重量％であった。
【００２１】
実施例８
コンデンサー、温度計、ガス吹き込み管を備えた３００ｍｌ容の三つ口フラスコに、１０．１重量％トリエチルアミン水溶液５０ｇを入れ、２５℃に保ちながら炭酸ガスを１時間吹き込んでアミンの炭酸塩を生成させた。反応後、２−クロロ−５−メチル−１−インダノール７．５６ｇ（０．０３３３ｍｏｌ）、アセトニトリル１７０ｇを加え、５０℃に保ち、炭酸ガスをさらに６時間吹き込んだ。反応終了後、溶液を室温まで放冷した後、トルエン１００ｇを加えて、炭酸インデンを抽出した。分液後、有機層からエバポレーションにより溶媒を除去した。これにより結晶性生成物４．５０ｇを得た。ＧＣ分析の結果、純度７７．４重量％であった。
【００２３】
実施例９
実施例８と同じ反応器に、１０．１重量％トリエチルアミン水溶液５０ｇを入れ、２５℃に保ちながら炭酸ガスを１時間吹き込んでアミンの炭酸塩を生成させた。反応後、１，２−インダンジオール５．０ｇ（０．０３３３ｍｏｌ）、アセトニトリル１７０ｇを加え、５０℃に保ち、炭酸ガスをさらに６時間吹き込んだ。反応終了後、溶液を室温まで放冷した後、トルエン１００ｇを加えて、炭酸インデンを抽出した。分液後、有機層からエバポレーションにより溶媒を除去した。これにより結晶性生成物４．６５ｇを得た。ＧＣ分析の結果、純度９０．６重量％であった。
【００２４】
【発明の効果】
本発明によれば、インダンジオール、ハロゲン化インダノールおよびそれらのアルキル置換体から、炭酸インデンを簡便に高純度で製造することができる。[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a method for producing a carbonic indene is useful as a resin material and chemical intermediates, and further details alkyl indane diol, a etc. halogenated Indano Le as a starting material, the carbonate of amines, inorganic carbonates, The present invention relates to a method for producing indene carbonate which is reacted with a salt type anion exchange resin or carbon dioxide gas.
[0002]
[Prior art]
As a conventional method for producing indene carbonate, 1,2-indanediol is synthesized from indene and then reacted with 1,1′-carbonyldiimidazole to produce indene carbonate (RCWhite, P. Drew and R. Moorman, J. Heterocycl. Chem, 25, 1781 (1988)), and a method for producing indene carbonate by reacting phosgene with 1,2-indanediol (RAAustin and CPLillya, J. Org. Chem, 34 (5 ), 1327 (1969)) are generally known.
[0003]
[Problems to be solved by the invention]
However, the above conventional methods have problems in application to industrial mass production processes such as using expensive raw materials or requiring highly toxic raw materials. Accordingly, an object of the present invention is to provide a method for producing indene carbonate which can be applied to a mass production process using a raw material which is inexpensive and less dangerous.
[0004]
[Means for Solving the Problems]
The above object is achieved by the present invention described below. That is, the present invention provides the following general formula (1)
[0005]
The present inventors have, Lee Ndanjioru or halogenated indanol, or either reacting a and carbonate their alkyl-substituted compounds, preferably by reacting with a carbonate in a carbon atmosphere, found to be able to easily produce carbonic indene did. In the present invention, “carbonate” is used to include bicarbonate.
[0006]
DETAILED DESCRIPTION OF THE INVENTION
Next, the present invention will be described in more detail with reference to preferred embodiments.
Examples of the compound represented by the general formula (1) used as a raw material in the present invention include indandiols such as 5 -methyl-1,2-indanediol and 4-ethyl-1,2-indanediol, 2 Halogenated indanols such as -chloro-1-indanol, 2-bromo-5-ethyl-1-indanol, 1-chloro-5-methyl-2-indanol, 1-bromo-2-indanol. The purity of these raw materials is not particularly limited and may be high purity or low purity, but the impurity is preferably a compound inert to the reaction. Even if impurities are active in the reaction, they may be included in the practice of the present invention even if they are particularly included if they have a slight influence on the reaction.
[0007]
Examples of the carbonate used in the reaction in the present invention include carbonates or bicarbonates of amines such as methylamine, ethylamine, diethylamine, triethylamine, ethylenediamine, benzyltrimethylammonium, tetraethylammonium, pyridine, quinoline, diethylaminoethyl group, and the like. , Carbonate or bicarbonate type anion exchange resins having an ion exchange group such as trimethylaminomethyl group, or inorganic carbonates such as sodium carbonate, potassium carbonate, magnesium carbonate, calcium carbonate and hydrotalcite. . Among these, carbonates or bicarbonates of the above amines are particularly preferable.
[0008]
In the reaction, the reaction raw materials may be mixed as they are, but it is desirable to use a solvent in the reaction in order to uniformly disperse the reaction raw materials, particularly carbonate. Examples of the solvent include water, polar solvents such as acetonitrile and methanol, and nonpolar solvents such as toluene and benzene. The solvent may be a simple substance or a mixed solution of two kinds, and in the case of a mixed solvent, one component thereof may be water. In the present invention, the reaction temperature is −10 to 150 ° C., preferably 20 to 80 ° C. The reaction can be carried out under atmospheric pressure. You may pressurize as needed.
[0009]
In some cases, the reaction is carried out by mixing the raw materials and carbonate using a solvent and stirring while maintaining the predetermined reaction temperature, but in order to shorten the reaction time and increase the selectivity to indene carbonate. It is desirable to carry out the reaction in a carbon dioxide atmosphere by, for example, bubbling carbon dioxide in the reaction solution. The amount of carbon dioxide used may be an amount that can maintain the reaction system in a carbon dioxide atmosphere. The purity of the carbon dioxide gas is not particularly limited, but the impurity is preferably a compound that is inert to the reaction.
[0010]
The amount of carbonate used in the method of the present invention is 1 to 20 times mol, preferably 1 to 1 mol with respect to the number of moles of the raw material represented by the general formula (1) when the reaction system is not maintained in a carbonic acid atmosphere. 2 moles. On the other hand, when the reaction is carried out while maintaining the reaction system in a carbonic acid atmosphere, the amount of carbonate used is 0.1 to 20 times the moles of the raw material represented by the general formula (1), preferably 0.5 to 2 moles. In this case, carbonate ions consumed by the reaction are supplemented by carbon dioxide gas maintaining the reaction atmosphere, so that the carbonate has a catalytic action, and the reaction proceeds even when it is less than 1 mol. If the amount of carbonate used is less than 1 mole (when not in a carbon dioxide atmosphere) or 0.1 mole (when in a carbon dioxide atmosphere), the reaction will be remarkably slow. Moreover, even if the usage-amount is more than 20 times mole, reaction rate is not improved significantly and it is not economical. These carbonates may be prepared separately and added to the reaction system, or may be generated in the system by blowing carbon dioxide into an amine or anion exchange resin.
[0011]
The indene carbonate produced by the method of the present invention can be obtained by distilling off the solvent in the filtrate after separating the solid by filtration when a solid such as carbonate is suspended in the reaction solution after the reaction. . When carbonate or other inorganic substances are dissolved in the reaction solution after the reaction, the indene carbonate is obtained by extracting the indene carbonate with an appropriate organic solvent and distilling off the solvent. . Further, a highly pure indene carbonate product can be easily obtained by an ordinary purification method such as recrystallization from an appropriate organic solvent.
[0012]
【Example】
Next, the present invention will be described more specifically with reference to examples.
Example 1
In a 300 ml three-necked flask equipped with a condenser, a thermometer and a gas blowing tube, 8.0 g (0.0376 mol) of trans-2-bromo-1-indanol and 11.9 g (0.0563 mol) of benzyltrimethylammonium carbonate were added. ) And 200 g of acetonitrile were mixed. While maintaining the reaction solution at 50 ° C., carbon dioxide gas was blown for 1 hour. After completion of the reaction, the solution was allowed to cool to room temperature, and the suspended solid was separated by filtration. After acetonitrile was distilled off from the filtrate, 100 g of toluene was added. The solid was separated by filtration, and toluene was distilled off from the filtrate to crystallize indene carbonate. This gave 5.80 g of crystalline product. This product was 95% pure by GC analysis.
[0013]
Example 2
In the same reactor as in Example 1, 8.0 g (0.0376 mol) of trans-2-bromo-1-indanol, 11.9 g (0.0563 mol) of benzyltrimethylammonium carbonate and 200 g of toluene were mixed. Carbon dioxide gas was blown in for 6 hours while maintaining the reaction solution at 50 ° C. After the completion of the reaction, the solution was allowed to cool to room temperature, and the suspended solid was separated by filtration. Toluene was distilled off from the filtrate to crystallize indene carbonate. This gave 5.83 g of crystalline product. According to GC analysis, the purity was 97.6% by weight.
[0014]
Example 3
In the same reactor as in Example 1, 4.0 g (0.0188 mol) of trans-2-bromo-1-indanol, 20.0 g (0.238 mol) of basic magnesium carbonate (heavy) and 100 g of acetonitrile were mixed and mixed. did. Carbon dioxide gas was blown in for 6 hours while maintaining the reaction solution at 50 ° C. After completion of the reaction, the solution was allowed to cool to room temperature, and the suspended solid was separated by filtration. Acetonitrile was distilled off from the filtrate to crystallize indene carbonate. This gave 1.90 g of crystalline product. According to GC analysis, the purity was 95.2% by weight.
[0015]
Example 4
In the same reactor as in Example 1, 8.0 g (0.0376 mol) of trans-2-bromo-1-indanol, 8.0 g of an anion exchange resin (carbonic acid type) and 200 g of acetonitrile are mixed. While maintaining the reaction solution at 50 ° C., carbon dioxide gas was blown for 8 hours. After completion of the reaction, the solution was allowed to cool to room temperature, and the precipitated solid was separated by filtration. Acetonitrile was distilled off from the filtrate to crystallize indene carbonate. This gave 3.76 g of crystalline product. According to GC analysis, the purity was 93% by weight.
[0016]
Example 5
In the same reactor as in Example 1, 50 g of a 10.1 wt% triethylamine aqueous solution was placed, and carbon dioxide was blown in for 1 hour while maintaining the temperature at 25 ° C. to produce an amine carbonate. After the reaction, 7.1 g (0.0333 mol) of trans-2-bromo-1-indanol and 177 g of acetonitrile were added, and the temperature was maintained at 50 ° C., and carbon dioxide gas was blown for another 2 hours. After completion of the reaction, the solution was allowed to cool to room temperature, and then 100 g of toluene was added to extract indene carbonate. After separation, the solvent was removed from the organic layer by evaporation. This gave 4.98 g of crystalline product. According to GC analysis, the purity was 94.6% by weight.
[0017]
Example 6
In the same reactor as in Example 5, 50 g of a 10.1 wt% triethylamine aqueous solution was added, and carbon dioxide was blown in for 1 hour while maintaining the temperature at 25 ° C. to produce an amine carbonate. After the reaction, 7.1 g (0.0333 mol) of trans-2-bromo-1-indanol and 177 g of acetonitrile were added, and the temperature was maintained at 50 ° C., and carbon dioxide gas was blown for another 2 hours. After completion of the reaction, the solution was allowed to cool to room temperature, and then the solvent was distilled off. Further, the remaining compound was vacuum-dried at room temperature to obtain 5.20 g of a crystalline product. The purity was 97.3% by weight by GC analysis.
[0020]
Example 7
Into a 200 ml three-necked flask equipped with a condenser, thermometer, and gas blowing tube, 33.3 g of a 10.1 wt% triethylamine aqueous solution was placed, and carbon dioxide was blown in for 1 hour while maintaining at 25 ° C. to produce an amine carbonate I let you. After the reaction, 4.73 g (0.0222 mol) of trans-2-bromo-1-indanol and 110 g of acetonitrile were added and stirred while maintaining at 50 ° C. The reaction was carried out for 6 hours. After completion of the reaction, the solution was allowed to cool to room temperature, and then the solvent was distilled off. Further, the remaining compound was vacuum-dried at room temperature to obtain 4.05 g of a crystalline product. The results of GC analysis, the purity was Tsu der 75.6% by weight.
[0021]
Example 8
A 300 ml three-necked flask equipped with a condenser, a thermometer, and a gas blowing tube was charged with 50 g of a 10.1 wt% triethylamine aqueous solution, and carbon dioxide was blown for 1 hour while maintaining at 25 ° C. to produce an amine carbonate. It was. After the reaction, 7.56 g (0.0333 mol) of 2-chloro-5-methyl-1-indanol and 170 g of acetonitrile were added, and the temperature was kept at 50 ° C., and carbon dioxide gas was blown for another 6 hours. After completion of the reaction, the solution was allowed to cool to room temperature, and 100 g of toluene was added to extract indene carbonate. After separation, the solvent was removed from the organic layer by evaporation. This gave 4.50 g of crystalline product. As a result of GC analysis, the purity was 77.4% by weight.
[0023]
Example 9
In the same reactor as in Example 8 , 50 g of a 10.1 wt% triethylamine aqueous solution was added, and carbon dioxide was blown in for 1 hour while maintaining the temperature at 25 ° C. to produce an amine carbonate. After the reaction, 5.0 g (0.0333 mol) of 1,2-indanediol and 170 g of acetonitrile were added, and the temperature was maintained at 50 ° C., and carbon dioxide gas was further blown for 6 hours. After completion of the reaction, the solution was allowed to cool to room temperature, and 100 g of toluene was added to extract indene carbonate. After separation, the solvent was removed from the organic layer by evaporation. This gave 4.65 g of a crystalline product. As a result of GC analysis, the purity was 90.6% by weight.
[0024]
【The invention's effect】
According to the present invention, it is possible to indane diol, halogenated Indano Le us and their alkyl substitution products are prepared in a simple high purity carbonate indene.
Claims (3)
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| JP19570599A JP4220619B2 (en) | 1999-07-09 | 1999-07-09 | Method for producing indene carbonate |
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| JP19570599A JP4220619B2 (en) | 1999-07-09 | 1999-07-09 | Method for producing indene carbonate |
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| BR112013014972B1 (en) | 2010-12-15 | 2020-12-29 | Queen's University At Kingston | method for removing a solute from the aqueous solution or for concentrating the diluted aqueous solution by modulating the ionic strength of an aqueous solution |
| CN112409190B (en) * | 2020-11-05 | 2022-03-01 | 河南大学 | Method for efficiently synthesizing cyclic carbonate by using amine salt ionic liquid as catalyst |
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