JP3231048B2 - Method for producing tetramethylammonium hydrogen carbonate aqueous solution for producing quaternary ammonium hydroxide by electrolysis - Google Patents
Method for producing tetramethylammonium hydrogen carbonate aqueous solution for producing quaternary ammonium hydroxide by electrolysisInfo
- Publication number
- JP3231048B2 JP3231048B2 JP10105091A JP10105091A JP3231048B2 JP 3231048 B2 JP3231048 B2 JP 3231048B2 JP 10105091 A JP10105091 A JP 10105091A JP 10105091 A JP10105091 A JP 10105091A JP 3231048 B2 JP3231048 B2 JP 3231048B2
- Authority
- JP
- Japan
- Prior art keywords
- tetramethylammonium
- producing
- aqueous solution
- methanol
- carbonate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【０００１】[0001]
【産業上の利用分野】本発明は、電気分解によつて水酸
化第四アンモニウムを製造するための炭酸水素テトラメ
チルアンモニウム水溶液の製造方法に関する。The present invention relates to, go-between water acid electrolysis
The present invention relates to a method for producing an aqueous solution of tetramethylammonium bicarbonate for producing quaternary ammonium fluoride.
【０００２】[0002]
【従来の技術】例えば、特開昭６３−２４０８０号公報
に記載されているように、炭酸ジメチルとトリメチルア
ミンとをメタノール溶媒中で反応させて、炭酸ジテトラ
メチルアンモニウムを主成分として含む反応混合物を
得、これより反応溶媒と未反応原料を蒸留にて除去した
後、得られた蒸留残留物を再度、水に溶解し、蒸留し
て、残留メタノールを更に除去して、炭酸ジテトラメチ
ルアンモニウム、炭酸水素テトラメチルアンモニウム又
はこれらの混合物を得、これらを再度、水に溶解させて
水溶液とし、これを電気分解に付して、水酸化第四アン
モニウムを得ることが知られている。しかし、このよう
な方法によつて、炭酸ジテトラメチルアンモニウム、炭
酸水素テトラメチルアンモニウム又はこれらの混合物を
得、その水溶液を電気分解して、水酸化第四アンモニウ
ムを得る方法によれば、反応工程が多く、生産性に劣
る。 2. Description of the Related Art For example, Japanese Patent Application Laid-Open No. 63-24080
Dimethyl carbonate and trimethyl alcohol as described in
With methanol in a methanol solvent to give ditetracarbonate.
Reaction mixture containing methyl ammonium as the main component
From which the reaction solvent and unreacted raw materials were removed by distillation.
Afterwards, the distillation residue obtained is again dissolved in water and distilled.
To further remove residual methanol and ditetramethyl carbonate
Ammonium, tetramethylammonium bicarbonate or
Obtains these mixtures and dissolves them again in water
An aqueous solution, which was subjected to electrolysis,
It is known to obtain monium. But like this
Ditetramethylammonium carbonate, charcoal
Tetramethylammonium oxyhydrogen or a mixture thereof
The aqueous solution is electrolyzed to obtain a quaternary ammonium hydroxide.
According to the method for obtaining a system, the number of reaction steps is large and productivity is poor.
【０００３】[0003]
【発明が解決しようとする課題】本発明は、電気分解に
よって水酸化第四アンモニウムを製造するための従来の
炭酸水素テトラメチルアンモニウム水溶液の製造におけ
る上記した問題を解決するためになされたものであつ
て、炭酸ジメチルとトリメチルアミンとをメタノールの
存在下で反応させて、炭酸テトラメチルアンモニウムメ
チルを含む反応混合物を得た後、この炭酸テトラメチル
アンモニウムメチルの加水分解と脱メタノールを同時に
行なつて、電気分解によって水酸化第四アンモニウムを
製造するために好適に用いることができる炭酸水素テト
ラメチルアンモニウム水溶液を生産性よく製造する方法
に関する。SUMMARY OF THE INVENTION The present invention relates to electrolysis.
Therefore, the conventional method for producing quaternary ammonium hydroxide
In order to solve the above-mentioned problems in the production of an aqueous solution of tetramethylammonium hydrogencarbonate , dimethylcarbonate and trimethylamine are converted to methanol.
Reaction in the presence of tetramethylammonium carbonate
After obtaining a reaction mixture containing tyl, the hydrolysis of tetramethylammonium methyl carbonate and the removal of methanol are simultaneously carried out, and quaternary ammonium hydroxide is obtained by electrolysis.
The present invention relates to a method for producing a tetramethylammonium hydrogencarbonate aqueous solution which can be suitably used for production with high productivity.
【０００４】[0004]
【課題を解決するための手段】本発明による電気分解に
よつて水酸化第四アンモニウムを製造するための炭酸水
素テトラメチルアンモニウム水溶液の製造方法は、炭酸
ジメチルとトリメチルアミンとをメタノールの存在下で
反応させて炭酸テトラメチルアンモニウムメチルを含む
反応混合物を得た後、この反応混合物に水を加えつつ、
炭酸テトラメチルアンモニウムメチルを加水分解すると
同時に脱メタノールすることを特徴とする。SUMMARY OF THE INVENTION In the electrolysis according to the present invention ,
Thus, the method for producing an aqueous solution of tetramethylammonium hydrogen carbonate for producing quaternary ammonium hydroxide is based on the reaction of dimethyl carbonate and trimethylamine in the presence of methanol to obtain a reaction mixture containing tetramethylammonium methyl carbonate. , While adding water to the reaction mixture,
It is characterized in that tetramethylammonium methyl carbonate is hydrolyzed and methanol is removed at the same time.
【０００５】本発明の方法において、炭酸テトラメチル
アンモニウムメチルは、炭酸ジメチルとトリメチルアミ
ンとをメタノールの存在下で反応させることによつて製
造される。トリメチルアミンは、通常、炭酸ジメチルに
対して0.８〜３モル比の範囲で用いられ、また、反応溶
剤としてのメタノールは、通常、炭酸ジメチルに対する
重量比にて５以下、好ましくは0.５〜2.０の範囲で用い
られる。反応は、常圧又は加圧下、好ましくは密閉系で
６０〜１８０℃、好ましくは８０〜１５０℃で0.５〜１
０時間、好ましくは２〜６時間行なわれる。反応方式
は、バツチ方式によつてもよく、また、炭酸ジメチルの
メタノール溶液中にトリメチルアミンを連続的に供給す
る部分連続方式によつてもよい。In the method of the present invention, tetramethylammonium methyl carbonate is produced by reacting dimethyl carbonate with trimethylamine in the presence of methanol. Trimethylamine is generally used in a range of 0.8 to 3 mol ratio to dimethyl carbonate, and methanol as a reaction solvent is usually 5 or less in weight ratio to dimethyl carbonate, preferably 0.5 to 0.5. Used in the range of 2.0. The reaction is carried out at normal pressure or under pressure, preferably in a closed system at 60 to 180 ° C, preferably at 80 to 150 ° C for 0.5 to 1 hour.
It is carried out for 0 hour, preferably for 2 to 6 hours. The reaction method may be a batch method or a partial continuous method in which trimethylamine is continuously supplied into a methanol solution of dimethyl carbonate.
【０００６】次いで、本発明の方法によれば、このよう
にして得られた炭酸テトラメチルアンモニウムメチルを
含む反応混合物に超純水を加えながら、炭酸テトラメチ
ルアンモニウムメチルを加水分解すると同時に脱メタノ
ールすることによつて、直ちに炭酸水素テトラメチルア
ンモニウム水溶液を得る。炭酸テトラメチルアンモニウ
ムメチルを含む反応混合物に加える水の量は、全反応時
間にわたつて、炭酸テトラメチルアンモニウムメチルに
対して、５〜１００モル比、好ましくは１０〜５０モル
比の範囲である。このように、本発明によれば、炭酸テ
トラメチルアンモニウムメチルを含む反応混合物に水を
加えながら、同時に未反応の炭酸ジメチル、トリメチル
アミン、メタノール及び水を留去し、かくして、炭酸テ
トラメチルアンモニウムメチルの加水分解と脱メタノー
ルを同時に行なう。Then, according to the method of the present invention, while adding ultrapure water to the thus obtained reaction mixture containing tetramethylammonium methyl carbonate, the tetramethylammonium methyl carbonate is hydrolyzed and methanol is removed at the same time. Thus, an aqueous solution of tetramethylammonium bicarbonate is immediately obtained. The amount of water added to the reaction mixture containing methyl tetramethylammonium carbonate is in the range of 5 to 100 molar ratio, preferably 10 to 50 molar ratio, based on the tetramethylammonium methyl carbonate over the entire reaction time. Thus, according to the present invention, while adding water to the reaction mixture containing tetramethylammonium methyl carbonate, at the same time, unreacted dimethyl carbonate, trimethylamine, methanol and water are distilled off. Hydrolysis and demethanol are performed simultaneously.
【０００７】ここに、反応温度は、０〜１２０℃、好ま
しくは３０〜１００℃であり、反応圧力は１０〜５００
mmHg、好ましくは１００〜３００mmHgの範囲であり、反
応時間は、１０分乃至２０時間、好ましくは３０分乃至
１０時間の範囲である。このようにして得られた炭酸水
素テトラメチルアンモニウムの水溶液を適宜濃度に希釈
し、これを常法に従つて電気分解すれば、水酸化第四ア
ンモニウム水溶液を得る。炭酸水素テトラメチルアンモ
ニウムの電気分解は、隔膜によつて隔てられた陰極室と
陽極室とを備えた電解槽を用いて、電解槽の陰極室内に
例えば１〜５％程度の水酸化第四アンモニウム水溶液を
循環させると共に、陽極室内に５〜３０％程度の炭酸水
素テトラメチルアンモニウム水溶液を循環させながら、
電流密度５〜３０Ａ／dm2 の条件で直流電圧を印加して
電気分解を行なう。電気分解の進行に伴つて陽極室には
炭酸水素テトラメチルアンモニウムを補充し、陰極室の
水酸化第四アンモニウム水溶液を抜き出せば、連続して
電気分解を行なうことができる。The reaction temperature is 0 to 120 ° C., preferably 30 to 100 ° C., and the reaction pressure is 10 to 500 ° C.
The reaction time is in the range of 10 minutes to 20 hours, preferably in the range of 30 minutes to 10 hours. The aqueous solution of tetramethylammonium hydrogen carbonate thus obtained is diluted to an appropriate concentration and electrolyzed according to a conventional method to obtain an aqueous quaternary ammonium hydroxide solution. For the electrolysis of tetramethylammonium hydrogen carbonate, for example, about 1 to 5% quaternary ammonium hydroxide is used in an electrolytic cell having a cathode chamber and an anode chamber separated by a diaphragm. While circulating the aqueous solution, while circulating a 5 to 30% aqueous solution of tetramethylammonium bicarbonate in the anode chamber,
Electrolysis is performed by applying a DC voltage under the conditions of a current density of 5 to 30 A / dm 2 . As the electrolysis proceeds, the anode chamber is replenished with tetramethylammonium hydrogencarbonate, and the aqueous solution of quaternary ammonium hydroxide in the cathode chamber is withdrawn, whereby the electrolysis can be performed continuously.
【０００８】[0008]
【発明の効果】以上のように、本発明の方法によれば、
炭酸ジメチルとトリメチルアミンとをメタノールの存在
下で反応させて炭酸テトラメチルアンモニウムメチルを
含む反応混合物を得た後、この反応混合物に水を加えつ
つ、炭酸テトラメチルアンモニウムメチルを加水分解す
ると同時に脱メタノールすることによつて、工程を短縮
化、簡略化でき、短時間に生産性よく炭酸水素テトラメ
チルアンモニウムを得ることができ、更には、残存メタ
ノール量の少ない炭酸水素テトラメチルアンモニウム水
溶液を得ることができる。As described above, according to the method of the present invention,
After reacting dimethyl carbonate and trimethylamine in the presence of methanol to obtain a reaction mixture containing tetramethylammonium methyl carbonate, while adding water to the reaction mixture, hydrolyze the tetramethylammonium methyl carbonate and simultaneously remove methanol. Thereby, the process can be shortened and simplified, tetramethylammonium hydrogencarbonate can be obtained with high productivity in a short time, and further, an aqueous solution of tetramethylammonium hydrogencarbonate having a small amount of residual methanol can be obtained. .
【０００９】[0009]
実施例１ 炭酸ジメチル１９０ｇ（2.１モル）、トリメチルアミン
１２４ｇ（2.１モル）及びメタノール１９０ｇを反応器
内に仕込み、１２５℃で３時間反応させた。得られた反
応生成物の組成は、トリメチルアミン0.８重量％、炭酸
ジメチル1,３重量％、メタノール３7.８重量％及び炭酸
テトラメチルアンモニウムメチル６0.１重量％（収率９
6.６％）であつた。Example 1 190 g (2.1 mol) of dimethyl carbonate, 124 g (2.1 mol) of trimethylamine and 190 g of methanol were charged in a reactor and reacted at 125 ° C. for 3 hours. The composition of the obtained reaction product was 0.8% by weight of trimethylamine, 1.3% by weight of dimethyl carbonate, 37.8% by weight of methanol, and 60.1% by weight of tetramethylammonium methyl carbonate (yield: 9%).
6.6%).
【００１０】この６０％炭酸テトラメチルアンモニウム
メチルのメタノール溶液２2.５重量部に対して、超純水
２9.４重量部の割合を４０段の蒸留塔の中央部から合計
にて３７１重量部／時でフイードしながら、ボトム温度
９０℃、トツプ温度４3.５℃、圧力３００mmHgで連続蒸
留して、トツプからは６7.２重量部／時、サイドからは
１４4.４重量部／時、ボトムからは１５9.５重量部／時
にて留分を得た。The ratio of 29.4 parts by weight of ultrapure water to 22.5 parts by weight of the methanol solution of 60% tetramethylammonium methyl carbonate was 371 parts by weight in total from the center of the 40-stage distillation column. Continuous feed at a bottom temperature of 90 ° C, a top temperature of 43.5 ° C, and a pressure of 300mmHg while feeding at time, 67.2 parts by weight / hour from the top, 144.4 parts by weight / hour from the side, and from the bottom Yielded a fraction at 159.5 parts by weight / hour.
【００１１】トツプ留分の組成は、トリメチルアミン1.
９重量％、炭酸ジメチル3.１重量％、メタノール９4.９
重量％、水0.１重量％、サイド留分の組成は、メタノー
ル１2.３９重量％、水８7.５７重量％、また、ボトム留
分の組成は、炭酸水素テトラメチルアンモニウム５4.８
重量％、水４5.２重量％であつた。この炭酸水素テトラ
メチルアンモニウム水溶液を超純水にて濃度１５％に希
釈し、電気分解に供した。The composition of the top fraction is trimethylamine 1.
9% by weight, dimethyl carbonate 3.1% by weight, methanol 94.9
% Of water, 0.1% by weight of water, composition of side fraction: 12.39% by weight of methanol, 87.57% by weight of water, and composition of bottom fraction: tetramethylammonium hydrogencarbonate 54.8%
% Of water and 45.2% by weight of water. This aqueous solution of tetramethylammonium bicarbonate was diluted with ultrapure water to a concentration of 15% and subjected to electrolysis.
【００１２】用いた電解槽は、白金属金属酸化物被覆チ
タンからなる陽極とニツケルからなる陰極とナフイオン
膜（デユポン社製）を備えたもので、この電解槽の陽極
室内に上記濃度１５％の炭酸水素テトラメチルアンモニ
ウム水溶液を滞留時間１０秒にて循環させ、陰極室内に
濃度５％の第四水酸化アンモニウム水溶液を滞留時間１
８秒にて循環させながら、陰極と陽極との間に電圧１５
Ｖ、電流密度３０Ａ／dm2 の直流電圧を印加し、陽極室
には炭酸水素テトラメチルアンモニウム水溶液を補充
し、陰極室からはそれに見合う量を抜き出した。１０時
間後、水酸化第四アンモニウム１９3.８を含む水溶液を
得た。 実施例２ 実施例１と同様にして炭酸テトラメチルアンモニウムメ
チルを含む反応生成物を得た。反応器に超純水７６０ｇ
を加えながら、同時にメタノールと水を６０℃／２００
mmHgの条件下に反応器から留去して、炭酸テトラメチル
アンモニウムメチルの加水分解と脱メタノールを同時に
行なつた。反応終了後、反応器から６０％濃度の炭酸水
素テトラメチルアンモニウムを定量的に得た。The electrolytic cell used was provided with an anode made of white metal oxide coated titanium, a cathode made of nickel, and a naphion membrane (manufactured by DuPont). An aqueous solution of tetramethylammonium hydrogen carbonate is circulated for a residence time of 10 seconds, and a quaternary ammonium hydroxide aqueous solution having a concentration of 5% is retained in the cathode chamber for a residence time of 1 second.
While circulating for 8 seconds, a voltage of 15 was applied between the cathode and the anode.
V, a DC voltage of a current density of 30 A / dm 2 was applied, an aqueous solution of tetramethylammonium bicarbonate was replenished in the anode compartment, and an appropriate amount was extracted from the cathode compartment. After 10 hours, an aqueous solution containing 193.8 quaternary ammonium hydroxide was obtained. Example 2 A reaction product containing tetramethylammonium methyl carbonate was obtained in the same manner as in Example 1. 760 g of ultrapure water in the reactor
While adding methanol and water at 60 ° C / 200
The reaction mixture was distilled off from the reactor under the condition of mmHg, and hydrolysis of tetramethylammonium methyl carbonate and demethanol were simultaneously performed. After the completion of the reaction, a 60% concentration of tetramethylammonium bicarbonate was quantitatively obtained from the reactor.
───────────────────────────────────────────────────── フロントページの続き (56)参考文献 特開 昭63−284148（ＪＰ，Ａ) 特開 昭63−132863（ＪＰ，Ａ) (58)調査した分野(Int.Cl.7，ＤＢ名) C07C 211/00 C07C 209/00 ＣＡ（ＳＴＮ)────────────────────────────────────────────────── (5) References JP-A-63-284148 (JP, A) JP-A-63-132863 (JP, A) (58) Fields investigated (Int. Cl. 7 , DB name) C07C 211/00 C07C 209/00 CA (STN)
Claims (3)
ノールの存在下で反応させて炭酸テトラメチルアンモニ
ウムメチルを含む反応混合物を得た後、この反応混合物
に水を加えつつ、炭酸テトラメチルアンモニウムメチル
を加水分解すると同時に脱メタノールすることを特徴と
する電気分解によつて水酸化第四アンモニウムを製造す
るための炭酸水素テトラメチルアンモニウム水溶液の製
造方法。1. A reaction mixture containing tetramethylammonium methyl carbonate by reacting dimethyl carbonate and trimethylamine in the presence of methanol, and then hydrolyzing the tetramethylammonium methyl carbonate while adding water to the reaction mixture. To produce quaternary ammonium hydroxide by electrolysis, which is characterized by simultaneously removing methanol .
For producing an aqueous solution of tetramethylammonium hydrogen carbonate for use in production.
ムメチルに対して５〜１００モル比の水を加えつつ、炭
酸テトラメチルアンモニウムメチルを加水分解すると同
時に脱メタノールすることを特徴とする請求項１記載の
炭酸水素テトラメチルアンモニウム水溶液の製造方法。2. The method according to claim 1, wherein water is added to the reaction mixture in a molar ratio of 5 to 100 with respect to tetramethylammonium methyl carbonate to hydrolyze the tetramethylammonium methyl carbonate and simultaneously remove methanol. A method for producing an aqueous solution of tetramethylammonium hydrogen carbonate.
ムメチルに対して５〜１００モル比の水を加えつつ、温
度０〜１２０℃、圧力１０〜５００mmHgの条件下に炭酸
テトラメチルアンモニウムメチルを加水分解すると同時
に脱メタノールすることを特徴とする請求項１記載の炭
酸水素テトラメチルアンモニウム水溶液の製造方法。3. Hydrolysis of tetramethylammonium methyl carbonate at a temperature of 0 to 120 ° C. and a pressure of 10 to 500 mmHg while adding water to the reaction mixture in a molar ratio of 5 to 100 with respect to tetramethylammonium methyl carbonate. The method for producing an aqueous solution of tetramethylammonium bicarbonate according to claim 1, wherein the methanol is removed simultaneously.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10105091A JP3231048B2 (en) | 1991-05-02 | 1991-05-02 | Method for producing tetramethylammonium hydrogen carbonate aqueous solution for producing quaternary ammonium hydroxide by electrolysis |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10105091A JP3231048B2 (en) | 1991-05-02 | 1991-05-02 | Method for producing tetramethylammonium hydrogen carbonate aqueous solution for producing quaternary ammonium hydroxide by electrolysis |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04334353A JPH04334353A (en) | 1992-11-20 |
| JP3231048B2 true JP3231048B2 (en) | 2001-11-19 |
Family
ID=14290296
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10105091A Expired - Lifetime JP3231048B2 (en) | 1991-05-02 | 1991-05-02 | Method for producing tetramethylammonium hydrogen carbonate aqueous solution for producing quaternary ammonium hydroxide by electrolysis |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3231048B2 (en) |
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| JP2010116349A (en) * | 2008-11-13 | 2010-05-27 | Tosoh Corp | New n,n,n-trimethyl-1-adamantane ammonium methyl carbonate |
| JP2010138087A (en) * | 2008-12-10 | 2010-06-24 | Tosoh Corp | Method for producing n,n,n-trialkyladamantane ammonium alkyl carbonate |
| JP5428501B2 (en) * | 2009-04-28 | 2014-02-26 | 東ソー株式会社 | Structure directing agent for zeolite production |
| JP5655910B2 (en) * | 2013-08-12 | 2015-01-21 | 東ソー株式会社 | Process for producing novel N, N, N-trimethyl-1-adamantanammonium methyl carbonate |
-
1991
- 1991-05-02 JP JP10105091A patent/JP3231048B2/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8095257B2 (en) | 2007-02-16 | 2012-01-10 | Denso Corporation | Electronic control apparatus having self-diagnosis function |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH04334353A (en) | 1992-11-20 |
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