JPH08119911A - Production of choline carbonate and choline bicarbonate having high purity - Google Patents
Production of choline carbonate and choline bicarbonate having high purityInfo
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- JPH08119911A JPH08119911A JP25576094A JP25576094A JPH08119911A JP H08119911 A JPH08119911 A JP H08119911A JP 25576094 A JP25576094 A JP 25576094A JP 25576094 A JP25576094 A JP 25576094A JP H08119911 A JPH08119911 A JP H08119911A
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- choline
- carbonate
- bicarbonate
- purity
- bis
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Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、炭酸コリン乃至重炭酸
コリンの製造方法に関するもので、より詳細には副生物
を含むコリンから、高純度のコリン炭酸塩乃至コリン重
炭酸塩を製造する方法に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for producing choline carbonate or choline bicarbonate, and more particularly to a method for producing high-purity choline carbonate or choline bicarbonate from choline containing by-products. Regarding
【０００２】[0002]
【従来の技術】本発明者らは既に、「第四級アンモニウ
ムハイドロオキサイド乃至その塩の包接錯体並びに該包
接錯体の製造方法」（特願平６−３８８９４号）におい
て、第四級アンモニウムハイドロオキサイド乃至その塩
の包接錯体並びに該包接錯体の製造方法を提案してい
る。2. Description of the Related Art The present inventors have already described in the description of "inclusion complex of quaternary ammonium hydroxide or a salt thereof and a method for producing the inclusion complex" (Japanese Patent Application No. 6-38894). An inclusion complex of hydroxide or a salt thereof and a method for producing the inclusion complex are proposed.
【０００３】コリンは、強塩基性物質であり、フォトレ
ジスト現像液として使用されているが、コリン製造時に
副生する副生物を除くことは不可能で、従来は副生物共
存下で利用されている。Although choline is a strongly basic substance and is used as a photoresist developing solution, it is impossible to remove by-products produced as a by-product during the production of choline, and it has been conventionally used in the presence of by-products. There is.
【０００４】[0004]
【発明が解決しようとする課題】コリンは、一般的に式
（１）に従って製造される。Choline is generally produced according to formula (1).
【０００５】[0005]
【化１】 Embedded image
【０００６】この反応の副生物として、式（２）の化合
物が推定されている。As a by-product of this reaction, the compound of formula (2) is presumed.
【０００７】[0007]
【化２】 Embedded image
【０００８】この副生物は、コリンに更にエチレンオキ
サイドが逐次的に付加反応したもので、ｎ＝１および２
が主なものである。従来のコリン水溶液中には、上記副
生物がコリンに対して２〜３重量％程度含まれている。This by-product is obtained by sequentially adding ethylene oxide to choline, and n = 1 and 2
Is the main one. The above-mentioned by-product is contained in the conventional choline aqueous solution in an amount of about 2 to 3% by weight with respect to choline.
【０００９】この副生物は、コリン反応条件の改良、蒸
留、再結晶、吸着など一般的な化学的物理的操作処理で
は、生成抑制や除去は実用上不可能である。副生物を含
まない高純度コリンを製造することが出来れば、フォト
レジスト現像液としての更なる用途拡大につながるのみ
ならず、医薬、農薬および機能性材料などの分野におけ
る新規用途開拓が期待できる。This by-product cannot be practically suppressed or removed by general chemical and physical operation treatments such as improvement of choline reaction conditions, distillation, recrystallization and adsorption. If high-purity choline containing no by-products can be produced, not only will it lead to further expansion of applications as a photoresist developer, but it can also be expected to open up new applications in fields such as pharmaceuticals, agricultural chemicals and functional materials.
【００１０】本発明者らは、前記提案の特願平６−３８
８９４号に引き続き鋭意研究を重ねた結果、高純度炭酸
コリン乃至重炭酸コリンの製造方法を見いだし本発明に
至った。The inventors of the present invention have proposed the above-mentioned Japanese Patent Application No. 6-38.
As a result of repeated intensive research after No. 894, a method for producing high-purity choline carbonate or choline bicarbonate was found, and the present invention was accomplished.
【００１１】即ち、本発明の目的は、副生物を含まない
高純度炭酸コリン乃至重炭酸コリンの製造方法を提供す
るものである。なお、本発明において得られる高純度炭
酸コリン乃至重炭酸コリンは、イオン交換膜を隔膜とす
る電気分解法により高純度コリンとして提供可能であ
る。That is, an object of the present invention is to provide a method for producing high-purity choline carbonate or choline bicarbonate that does not contain by-products. The high-purity choline carbonate or choline bicarbonate obtained in the present invention can be provided as high-purity choline by an electrolysis method using an ion exchange membrane as a diaphragm.
【００１２】[0012]
【課題を解決するための手段】本発明によれば、コリン
の分子包接錯体と炭酸ガスを反応させ高純度の炭酸コリ
ン乃至重炭酸コリンを製造することを特徴とする高純度
炭酸コリン乃至重炭酸コリンの製造方法が提供される。According to the present invention, a high-purity choline carbonate or heavy-carbon choline carbonate is produced by reacting a molecular inclusion complex of choline with carbon dioxide gas. A method for producing choline carbonate is provided.
【００１３】本発明によれば、不純物を含有するコリン
水溶液と１，１′−ビス−β−ナフトールを反応させ、
得られるコリンの分子包接錯体と炭酸ガスを反応させて
高純度の炭酸コリン乃至重炭酸コリンを製造することを
特徴とする高純度の炭酸コリン乃至重炭酸コリンの製造
方法が提供される。According to the present invention, an aqueous choline solution containing impurities is reacted with 1,1'-bis-β-naphthol,
A process for producing high-purity choline carbonate or choline bicarbonate, which comprises reacting the obtained molecular inclusion complex of choline with carbon dioxide to produce high-purity choline carbonate or choline bicarbonate.
【００１４】[0014]
【作用】ある化合物が他の分子を取り込んで錯体を形成
するとき、この錯体を分子包接錯体といい、前者の化合
物をホスト分子、後者の分子をゲスト分子という。When a compound incorporates another molecule to form a complex, this complex is called a molecular inclusion complex, the former compound is called a host molecule, and the latter molecule is called a guest molecule.
【００１５】本発明は、コリン水溶液中のコリンのみが
１，１′−ビス−β−ナフトール等のホスト分子と分子
包接錯体を形成し、副生物とは分子包接錯体を形成しな
いという新規な知見に基づくものであり、コリン水溶液
と１，１′−ビス−β−ナフトール等のホスト分子を反
応させて、副生物を含まないコリン包接錯体を得、次い
でコリン包接錯体を水に分散させ、炭酸ガスを吹き込ん
で、高純度の炭酸コリン乃至重炭酸コリンを水溶液の形
で得るものである。The present invention is novel in that only choline in an aqueous solution of choline forms a molecular inclusion complex with a host molecule such as 1,1'-bis-β-naphthol and does not form a molecular inclusion complex with a by-product. Based on such findings, an aqueous solution of choline is reacted with a host molecule such as 1,1′-bis-β-naphthol to obtain a choline inclusion complex containing no by-products, and then the choline inclusion complex is added to water. By dispersing and blowing carbon dioxide gas, high-purity choline carbonate or choline bicarbonate is obtained in the form of an aqueous solution.
【００１６】即ち、コリン包接錯体に取り込まれていた
コリンは、炭酸ガスと反応して水溶性の重炭酸コリン或
いは炭酸コリンとなり、水に溶解して重炭酸コリン或い
は炭酸コリンの水溶液が得られる。この反応は次式
（３）、（４）及び（５）で表される。That is, the choline incorporated in the choline inclusion complex reacts with carbon dioxide gas to become water-soluble choline bicarbonate or choline carbonate, and is dissolved in water to obtain an aqueous solution of choline bicarbonate or choline carbonate. . This reaction is represented by the following equations (3), (4) and (5).
【００１７】[0017]
【化３】 Embedded image
【００１８】[0018]
【化４】 [Chemical 4]
【００１９】[0019]
【化５】 Embedded image
【００２０】[0020]
【発明の好適態様】本発明に使用するホスト化合物とし
ては、例えば特公平６−２１０１７号公報に記載されて
いるフェノール化合物を挙げることができるが、特に好
適なものとして、１，１′−ビス−β−ナフトール、即
ち、下記式（６）の化合物が使用される。BEST MODE FOR CARRYING OUT THE INVENTION As the host compound used in the present invention, for example, a phenol compound described in Japanese Patent Publication No. 6-21017 can be mentioned, and particularly preferable one is 1,1'-bis. -Β-naphthol, that is, the compound of the following formula (6) is used.
【００２１】[0021]
【化６】 [Chemical 6]
【００２２】本発明に使用するゲスト化合物はコリンで
あり、式（１）の方法で製造されるコリン水溶液を原料
として使用可能である。The guest compound used in the present invention is choline, and the choline aqueous solution produced by the method of the formula (1) can be used as a raw material.
【００２３】本発明の高純度炭酸コリン乃至重炭酸コリ
ンの製造は、以下のような簡単な方法で実施可能であ
る。The high-purity choline carbonate or choline bicarbonate of the present invention can be produced by the following simple method.
【００２４】１，１′−ビス−β−ナフトールおよびコ
リン水溶液を１，１′−ビス−β−ナフトール／コリン
＝１／１ 又は１／２(モル比）となるような割合で、純
水と共に反応器に仕込み、加熱溶解させる。なお使用す
るコリン水溶液は、式（１）の方法で製造され、一般的
に式（２）の副生物をコリンに対して数重量％程度含ん
でいる。The 1,1'-bis-β-naphthol and choline aqueous solution was diluted with pure water in a ratio such that 1,1'-bis-β-naphthol / choline = 1/1 or 1/2 (molar ratio). Along with this, it is charged into a reactor and heated to dissolve. The aqueous choline solution used is produced by the method of formula (1), and generally contains the by-product of formula (2) in an amount of about several wt% with respect to choline.
【００２５】加熱溶解後、１，１′−ビス−β−ナフト
ールとコリンの分子包接錯体の結晶が直ちに析出する。
約１時間攪拌後、室温まで冷却して、濾過または遠心分
離後、水洗、乾燥し、副生物を含まない高純度分子包接
錯体を８０モル％以上の高収率で得ることが出来る。After dissolution by heating, crystals of a molecular inclusion complex of 1,1'-bis-β-naphthol and choline are immediately precipitated.
After stirring for about 1 hour, cooling to room temperature, filtration or centrifugation, washing with water and drying, a high-purity molecular inclusion complex containing no by-products can be obtained in a high yield of 80 mol% or more.
【００２６】得られた高純度分子包接錯体に純水を加
え、炭酸ガスを吹き込んだ後、１，１′−ビス−β−ナ
フトールを不溶結晶として濾過または遠心分離で除去す
ると、副生物を含まない高純度炭酸コリン乃至重炭酸コ
リン水溶液を得ることが出来る。なお、この水溶液中に
は、ホスト化合物の１，１′−ビス−β−ナフトールは
混入していない。Pure water was added to the obtained high-purity molecular inclusion complex, carbon dioxide gas was blown into it, and 1,1'-bis-β-naphthol was removed as an insoluble crystal by filtration or centrifugation to remove by-products. It is possible to obtain a highly pure choline carbonate or choline bicarbonate aqueous solution that does not contain it. The host compound 1,1'-bis-β-naphthol was not mixed in this aqueous solution.
【００２７】また、回収した１，１′−ビス−β−ナフ
トールは再使用可能であり、回収率はほぼ定量的であ
る。The recovered 1,1'-bis-β-naphthol can be reused, and the recovery rate is almost quantitative.
【００２８】[0028]
【実施例】以下、実施例を挙げて本発明を具体的に説明
するが、本発明はこれらの例によって何ら制限されるも
のではない。なお、包接錯体の１，１′−ビス−β−ナ
フトール／コリンの分子包接比は、ＮＭＲ（６０ＭＨ
ｚ）で、コリン水溶液中のコリン含量は、塩酸中和滴定
で、コリン水溶液、コリン包接錯体、炭酸コリン乃至重
炭酸コリン水溶液および分離母液中の式（２）で述べた
副生物は、イオンクロマトグラフィーで定量した。The present invention will be specifically described below with reference to examples, but the present invention is not limited to these examples. The molecular inclusion ratio of 1,1′-bis-β-naphthol / choline of the inclusion complex was determined by NMR (60 MH
In step z), the choline content in the aqueous choline solution is determined by hydrochloric acid neutralization titration, and the by-product described in the formula (2) in the aqueous choline solution, the choline inclusion complex, the aqueous choline carbonate solution or the aqueous choline bicarbonate solution and the separated mother liquor is an ion. It was quantified by chromatography.
【００２９】（実施例１） １，１′−ビス−β−ナフトール／コリン包接錯体の合
成 １，１′−ビス−β−ナフトール１．１４５ｇ（４．０
ｍｍｏｌ）と４７．７５重量％コリン水溶液２．０３０
ｇ（８．０ｍｍｏｌ）を、純水１０ｇに加え加熱溶解し
た。コリン水溶液中の副生物は、コリンに対して１．８
４重量％であった。加熱溶解後、直ちに結晶が析出し
た。更に、純水２０ｇを加え、濾過、水洗、乾燥後、
１，１′−ビス−β−ナフトール／コリン包接錯体を
１．４６０ｇ（収率８９．６０モル％）得た。融点測定
では、２１０〜２１３℃で分解しながら溶けた。また、
ＮＭＲから、包接錯体の分子比は、１，１′−ビス−β
−ナフトール／コリン＝１／１であった。包接錯体中の
コリンをイオンクロマトグラフィーで分析したところ、
副生物は、検出限界以下であった。また、包接錯体分離
母液および水洗液中のコリンは、合計０．５３５ｇ
（４．４ｍｍｏｌ）であった。(Example 1) Synthesis of 1,1'-bis-β-naphthol / choline inclusion complex 1,1'-bis-β-naphthol 1.145 g (4.0
mmol) and 47.75 wt% choline aqueous solution 2.030
g (8.0 mmol) was added to 10 g of pure water and dissolved by heating. The by-product in the choline aqueous solution is 1.8 with respect to choline.
It was 4% by weight. Crystals precipitated immediately after heating and dissolution. Furthermore, after adding 20 g of pure water, filtering, washing with water and drying,
1.460 g (yield 89.60 mol%) of 1,1′-bis-β-naphthol / choline inclusion complex was obtained. In melting point measurement, it melted while decomposing at 210 to 213 ° C. Also,
From NMR, the molecular ratio of the inclusion complex was 1,1′-bis-β.
-Naphthol / choline = 1/1. When choline in the inclusion complex was analyzed by ion chromatography,
By-products were below the detection limit. In addition, the total amount of choline in the inclusion complex separation mother liquor and the washing liquid was 0.535 g.
(4.4 mmol).
【００３０】（実施例２） １，１′−ビス−β−ナフトール／コリン包接錯体から
炭酸コリン乃至重炭酸コリンの合成 実施例１で得た副生物を含まない１，１′−ビス−β−
ナフトール／コリン包接錯体１．２４６ｇ（３．２ｍｍ
ｏｌ）を純水３０ｇに加え、攪拌しながら炭酸ガスを吹
き込んだ。不溶結晶を濾過、水洗して、高純度炭酸コリ
ン乃至重炭酸コリン水溶液５０．９３９ｇ（コリン換算
重量 ０．３７ｇ，３．１ｍｍｏｌ）を得た。収率９
５．４０モル％であった。この高純度炭酸コリン乃至重
炭酸コリン水溶液は、副生物を含んでいなかった。ま
た、不溶結晶は乾燥後、０．８５０ｇ（３．０ｍｍｏ
ｌ）を回収した。この不溶結晶は、ＩＲより１，１′−
ビス−β−ナフトールであることを確認した。回収率
は、９２．８０％であった。(Example 2) Synthesis of choline carbonate or choline bicarbonate from 1,1'-bis-β-naphthol / choline inclusion complex 1,1'-bis-containing no by-product obtained in Example 1 β-
Naphthol / choline inclusion complex 1.246 g (3.2 mm
ol) was added to 30 g of pure water, and carbon dioxide gas was blown in while stirring. The insoluble crystals were filtered and washed with water to obtain 50.939 g of a highly pure choline carbonate or choline bicarbonate aqueous solution (choline equivalent weight: 0.37 g, 3.1 mmol). Yield 9
It was 5.40 mol%. This high-purity choline carbonate or choline bicarbonate aqueous solution contained no by-products. In addition, the insoluble crystals were dried and dried at 0.850 g (3.0 mmo).
l) was recovered. This insoluble crystal is 1,1'-
It was confirmed to be bis-β-naphthol. The recovery rate was 92.80%.
【００３１】（実施例３） １，１′−ビス−β−ナフトール／コリン包接錯体の合
成 １，１′−ビス−β−ナフトール１．１４５ｇ（４．０
ｍｍｏｌ）と４７．７５重量％コリン水溶液１．０１４
ｇ（４．０ｍｍｏｌ）を、純水１０ｇに加え加熱溶解し
た。コリン水溶液中の副生物はコリンに対して１．８４
重量％であった。加熱溶解後、直ちに結晶が析出した。
更に、純水２０ｇを加え、濾過、水洗、乾燥後、１，
１′−ビス−β−ナフトール／コリン包接錯体を１．０
９０ｇ（収率７８．４０モル％）を得た。融点測定で
は、１０５〜１１０℃で分解しながら溶解した。ＮＭＲ
から包接錯体の分子比は、１，１′−ビス−β−ナフト
ール／コリン＝２／１であった。この包接錯体には、副
生物は含まれていなかった。また、分離母液中には、コ
リンが０．２６０ｇ（２．０ｍｍｏｌ）残存していた。Example 3 Synthesis of 1,1′-bis-β-naphthol / choline inclusion complex 1,1′-bis-β-naphthol 1.145 g (4.0)
mmol) and 47.75 wt% choline aqueous solution 1.014
g (4.0 mmol) was added to 10 g of pure water and dissolved by heating. The by-product in the choline aqueous solution is 1.84 with respect to choline.
% By weight. Crystals precipitated immediately after heating and dissolution.
Furthermore, after adding 20 g of pure water, filtering, washing with water and drying, 1,
1'-bis-β-naphthol / choline inclusion complex was added to 1.0
90 g (yield 78.40 mol%) was obtained. In melting point measurement, it was dissolved while decomposing at 105 to 110 ° C. NMR
Therefore, the molecular ratio of the inclusion complex was 1,1′-bis-β-naphthol / choline = 2/1. This inclusion complex contained no by-products. Further, 0.260 g (2.0 mmol) of choline remained in the separated mother liquor.
【００３２】（実施例４） １，１′−ビス−β−ナフトール／コリン包接錯体の合
成 １，１′−ビス−β−ナフトール４２．９０ｇ（０．１
５ｍｍｏｌ）と４７．７５重量％コリン水溶液７６．１
３ｇ（０．３０ｍｍｏｌ）を、純水３５０ｇに加え５０
℃で溶解した。コリン水溶液中の副生物は、コリンに対
して１．８４重量％であった。加熱溶解後、直ちに結晶
が析出した。５０℃で、１時間攪拌後、水４５０ｇを加
え、室温まで冷却した。冷却後、結晶を純水で２回水洗
し、乾燥して、１，１′−ビス−β−ナフトール／コリ
ン包接錯体を、５３．０ｇ（収率８８．２モル％）得
た。ＮＭＲから、包接錯体の分子比は、１，１′−ビス
−β−ナフトール／コリン＝１／１であった。この包接
錯体は、副生物を含んでいなかった。なお、分離母液お
よび水洗水中のコリンは、合計２０．１８ｇ（０．１６
６ｍｍｏｌ）であった。Example 4 Synthesis of 1,1′-bis-β-naphthol / choline inclusion complex 1,1′-bis-β-naphthol 42.90 g (0.1
5 mmol) and 47.75 wt% choline aqueous solution 76.1
Add 3 g (0.30 mmol) to 350 g of pure water and add 50
Melted at ° C. The by-product in the choline aqueous solution was 1.84% by weight based on choline. Crystals precipitated immediately after heating and dissolution. After stirring at 50 ° C. for 1 hour, 450 g of water was added and the mixture was cooled to room temperature. After cooling, the crystals were washed twice with pure water and dried to obtain 53.0 g (yield 88.2 mol%) of 1,1′-bis-β-naphthol / choline inclusion complex. From the NMR, the molecular ratio of the inclusion complex was 1,1′-bis-β-naphthol / choline = 1/1. This inclusion complex was free of by-products. The total amount of choline in the separated mother liquor and washing water was 20.18 g (0.16 g).
6 mmol).
【００３３】（実施例５） １，１′−ビス−β−ナフトール／コリン包接錯体から
炭酸コリン乃至重炭酸コリンの合成 実施例４で得た副生物を含まない１，１′−ビス−β−
ナフトール／コリン包接錯体４８．９０ｇ（０．１２ｍ
ｏｌ）を純水４００ｇに加え、攪拌しながら炭酸ガスを
吹き込んだ。不溶結晶を濾過、水洗して、炭酸コリン乃
至重炭酸コリン水溶液５００ｇ（コリン換算重量１２．
６０ｇ，０．１０４ｍｏｌ）を得た。収率８６．７０モ
ル％であった。イオンクロマトグラフィーで、炭酸コリ
ン乃至重炭酸コリン水溶液中の副生物を分析したが、検
出限界であった。不溶結晶は、乾燥後、ＩＲより１，
１′−ビス−β−ナフトールであることを確認した。回
収率は、ほぼ定量的であった。(Example 5) Synthesis of choline carbonate or choline bicarbonate from 1,1'-bis-β-naphthol / choline inclusion complex 1,1'-bis-containing no by-product obtained in Example 4 β-
Naphthol / choline inclusion complex 48.90g (0.12m
ol) was added to 400 g of pure water, and carbon dioxide gas was blown in while stirring. Insoluble crystals were filtered and washed with water to give 500 g of choline carbonate or choline bicarbonate aqueous solution (choline equivalent weight: 12.
60 g, 0.104 mol) was obtained. The yield was 86.70 mol%. By-products in the aqueous solution of choline carbonate or choline bicarbonate were analyzed by ion chromatography, but the detection limit was reached. The insoluble crystals were dried to give 1,
It was confirmed to be 1'-bis-β-naphthol. The recovery rate was almost quantitative.
【００３４】（比較例１）１，１′−ビス（４−ヒドロ
キシフェニル）−シクロヘキサン２．６８０ｇ（１０．
００ｍｍｏｌ）と４７．７５重量％コリン水溶液２．５
４ｇ（１０．００ｍｍｏｌ）を、純水１０ｇに加え、加
熱溶解した。コリン水溶液中の副生物は、コリンに対し
て１．８４重量％であった。加熱溶解後、一夜、室温で
放置した。次いで、純水２０ｇを加え、濾過、乾燥後、
１，１′−ビス（４−ヒドロキシフェニル）−シクロヘ
キサン／コリン包接錯体３．２０ｇ（収率９７．３モル
％）を得た。ＮＭＲから、この包接錯体の分子比は、
１，１′−ビス（４−ヒドロキシフェニル）−シクロヘ
キサン／コリン＝２／１であった。融点は、１１９〜１
５１℃でシャープではなかった。この包接錯体中の不純
物は、コリンに対して１．８４重量％であり、全く精製
されていなかった。この包接錯体３．１７ｇ（４．８０
ｍｍｏｌ）を純水３０ｇに加え、攪拌しながら炭酸ガス
を吹き込んだ。不溶結晶を濾過、水洗し、炭酸コリン乃
至重炭酸コリン水溶液７０．６０ｇ（コリン換算重量
０．５０１ｇ，４．１０ｍｍｏｌ）を得た。イオンクロ
マトグラフィーで、炭酸コリン乃至重炭酸コリン水溶液
中の副生物は、コリン換算重量に対して１．８２重量％
であり、全く精製されていなかった。(Comparative Example 1) 2,1'-bis (4-hydroxyphenyl) -cyclohexane 2.680 g (10.
00 mmol) and 47.75 wt% choline aqueous solution 2.5
4 g (10.00 mmol) was added to 10 g of pure water and dissolved by heating. The by-product in the choline aqueous solution was 1.84% by weight based on choline. After dissolution by heating, the mixture was left overnight at room temperature. Then, add 20 g of pure water, filter and dry,
3.20 g (yield 97.3 mol%) of 1,1'-bis (4-hydroxyphenyl) -cyclohexane / choline inclusion complex was obtained. From NMR, the molecular ratio of this inclusion complex is
It was 1,1'-bis (4-hydroxyphenyl) -cyclohexane / choline = 2/1. Melting point is 119-1
It was not sharp at 51 ° C. Impurities in this inclusion complex were 1.84% by weight with respect to choline and were not purified at all. This inclusion complex 3.17 g (4.80
(mmol) was added to 30 g of pure water, and carbon dioxide gas was blown in while stirring. The insoluble crystals were filtered and washed with water to obtain 70.60 g of choline carbonate or choline bicarbonate aqueous solution (choline equivalent weight 0.501 g, 4.10 mmol). By ion chromatography, the by-product in the choline carbonate or choline bicarbonate aqueous solution was 1.82% by weight based on the choline-converted weight.
And was not purified at all.
【００３５】[0035]
【発明の効果】本発明によれば、コリンに更にエチレン
オキサイドが付加した化合物を副生物として含むコリン
水溶液と１，１′−ビス−β−ナフトールのごときホス
ト分子を反応させて得られる副生物を含まないコリン包
接錯体を、炭酸ガスと反応させて高純度炭酸コリン乃至
重炭酸コリン水溶液を得ることが出来る。INDUSTRIAL APPLICABILITY According to the present invention, a by-product obtained by reacting an aqueous solution of choline containing a compound obtained by further adding ethylene oxide to choline as a by-product with a host molecule such as 1,1′-bis-β-naphthol. It is possible to obtain a highly pure choline carbonate or choline bicarbonate aqueous solution by reacting a choline inclusion complex containing no with carbon dioxide gas.
【００３６】なお、高純度炭酸コリン乃至重炭酸コリン
は、イオン交換膜を隔膜とする電気分解法により高純度
コリンとすることが可能である。コリンは、強塩基性化
合物であり、フォトレジスト現像液として極めて有用で
ある。High-purity choline carbonate or choline bicarbonate can be converted into high-purity choline by an electrolysis method using an ion exchange membrane as a diaphragm. Choline is a strongly basic compound and is extremely useful as a photoresist developer.
Claims (3)
させ高純度の炭酸コリン乃至重炭酸コリンを製造するこ
とを特徴とする高純度炭酸コリン乃至重炭酸コリンの製
造方法。1. A method for producing high-purity choline carbonate or choline bicarbonate, which comprises reacting a molecular inclusion complex of choline with carbon dioxide gas to produce high-purity choline carbonate or choline bicarbonate.
ト分子とし且つ１，１′−ビス−β−ナフトールをホス
ト分子とすることを特徴とする請求項１記載の製造方
法。2. The production method according to claim 1, wherein the molecular inclusion complex of choline uses choline as a guest molecule and 1,1′-bis-β-naphthol as a host molecule.
１′−ビス−β−ナフトールを反応させ、得られるコリ
ンの分子包接錯体と炭酸ガスを反応させて高純度の炭酸
コリン乃至重炭酸コリンを製造することを特徴とする高
純度の炭酸コリン乃至重炭酸コリンの製造方法。3. A choline aqueous solution containing impurities and 1,
1'-bis-β-naphthol is reacted, and the obtained molecular inclusion complex of choline is reacted with carbon dioxide gas to produce high-purity choline carbonate or choline bicarbonate. Method for producing choline bicarbonate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25576094A JP3471442B2 (en) | 1994-10-20 | 1994-10-20 | Method for producing high-purity choline carbonate or choline bicarbonate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25576094A JP3471442B2 (en) | 1994-10-20 | 1994-10-20 | Method for producing high-purity choline carbonate or choline bicarbonate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH08119911A true JPH08119911A (en) | 1996-05-14 |
| JP3471442B2 JP3471442B2 (en) | 2003-12-02 |
Family
ID=17283250
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP25576094A Expired - Fee Related JP3471442B2 (en) | 1994-10-20 | 1994-10-20 | Method for producing high-purity choline carbonate or choline bicarbonate |
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| Country | Link |
|---|---|
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109748808A (en) * | 2018-12-26 | 2019-05-14 | 济南蓬勃生物技术有限公司 | A kind of preparation method of Choline Bicarbonate and carbonate |
-
1994
- 1994-10-20 JP JP25576094A patent/JP3471442B2/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109748808A (en) * | 2018-12-26 | 2019-05-14 | 济南蓬勃生物技术有限公司 | A kind of preparation method of Choline Bicarbonate and carbonate |
| CN109748808B (en) * | 2018-12-26 | 2021-12-24 | 济南蓬勃生物技术有限公司 | Preparation method of choline bicarbonate and carbonate |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3471442B2 (en) | 2003-12-02 |
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