JPS63132863A - Production of quaternary ammonium bicarbonate - Google Patents
Production of quaternary ammonium bicarbonateInfo
- Publication number
- JPS63132863A JPS63132863A JP27875586A JP27875586A JPS63132863A JP S63132863 A JPS63132863 A JP S63132863A JP 27875586 A JP27875586 A JP 27875586A JP 27875586 A JP27875586 A JP 27875586A JP S63132863 A JPS63132863 A JP S63132863A
- Authority
- JP
- Japan
- Prior art keywords
- carbonate
- quaternary ammonium
- reaction
- monoaryl
- water
- 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.)
- Granted
Links
- 125000001453 quaternary ammonium group Chemical group 0.000 title claims abstract description 22
- 229910000013 Ammonium bicarbonate Inorganic materials 0.000 title claims description 11
- 235000012538 ammonium bicarbonate Nutrition 0.000 title claims description 11
- 239000001099 ammonium carbonate Substances 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims abstract description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 abstract description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract description 9
- -1 diaryl carbonate Chemical compound 0.000 abstract description 6
- 239000002798 polar solvent Substances 0.000 abstract description 6
- 239000002994 raw material Substances 0.000 abstract description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 4
- 239000004094 surface-active agent Substances 0.000 abstract description 3
- 150000003512 tertiary amines Chemical class 0.000 abstract description 3
- 239000012298 atmosphere Substances 0.000 abstract description 2
- 239000002537 cosmetic Substances 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 239000011261 inert gas Substances 0.000 abstract description 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 abstract 2
- 229910052786 argon Inorganic materials 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 4
- VFHDWENBWYCAIB-UHFFFAOYSA-M hydrogen carbonate;tetramethylazanium Chemical compound OC([O-])=O.C[N+](C)(C)C VFHDWENBWYCAIB-UHFFFAOYSA-M 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- HNPSEFNIHZRDED-UHFFFAOYSA-M propan-2-yl carbonate;tetramethylazanium Chemical compound C[N+](C)(C)C.CC(C)OC([O-])=O HNPSEFNIHZRDED-UHFFFAOYSA-M 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- OOOCZCRRNJUEAI-UHFFFAOYSA-M COC([O-])=O.C[N+](CCOC)(C)C Chemical compound COC([O-])=O.C[N+](CCOC)(C)C OOOCZCRRNJUEAI-UHFFFAOYSA-M 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- CFQGDIWRTHFZMQ-UHFFFAOYSA-N argon helium Chemical compound [He].[Ar] CFQGDIWRTHFZMQ-UHFFFAOYSA-N 0.000 description 1
- HWRODCJWUXAYAN-UHFFFAOYSA-M benzyl carbonate;tetramethylazanium Chemical compound C[N+](C)(C)C.[O-]C(=O)OCC1=CC=CC=C1 HWRODCJWUXAYAN-UHFFFAOYSA-M 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- YOUGRGFIHBUKRS-UHFFFAOYSA-N benzyl(trimethyl)azanium Chemical compound C[N+](C)(C)CC1=CC=CC=C1 YOUGRGFIHBUKRS-UHFFFAOYSA-N 0.000 description 1
- FYFYNZWCZYQKDI-UHFFFAOYSA-M benzyl(trimethyl)azanium;hydrogen carbonate Chemical compound OC([O-])=O.C[N+](C)(C)CC1=CC=CC=C1 FYFYNZWCZYQKDI-UHFFFAOYSA-M 0.000 description 1
- FHKVBKRABWGIMY-UHFFFAOYSA-M benzyl(trimethyl)azanium;methyl carbonate Chemical compound COC([O-])=O.C[N+](C)(C)CC1=CC=CC=C1 FHKVBKRABWGIMY-UHFFFAOYSA-M 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- NGLPJVQRIWSYNR-UHFFFAOYSA-M butyl carbonate;tetramethylazanium Chemical compound C[N+](C)(C)C.CCCCOC([O-])=O NGLPJVQRIWSYNR-UHFFFAOYSA-M 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- LPZLBGMZIPSQLR-UHFFFAOYSA-M diethyl(dimethyl)azanium;methyl carbonate Chemical compound COC([O-])=O.CC[N+](C)(C)CC LPZLBGMZIPSQLR-UHFFFAOYSA-M 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- LMASIWYRIYEBTQ-UHFFFAOYSA-M ethyl carbonate;tetraethylazanium Chemical compound CCOC([O-])=O.CC[N+](CC)(CC)CC LMASIWYRIYEBTQ-UHFFFAOYSA-M 0.000 description 1
- RTLSHXRUAOBZFH-UHFFFAOYSA-M ethyl carbonate;tetramethylazanium Chemical compound C[N+](C)(C)C.CCOC([O-])=O RTLSHXRUAOBZFH-UHFFFAOYSA-M 0.000 description 1
- KOLFZBNEVBCHPP-UHFFFAOYSA-M ethyl(trimethyl)azanium;hydrogen carbonate Chemical compound [H+].[O-]C([O-])=O.CC[N+](C)(C)C KOLFZBNEVBCHPP-UHFFFAOYSA-M 0.000 description 1
- QSPNICWOGNKGSW-UHFFFAOYSA-M ethyl(trimethyl)azanium;methyl carbonate Chemical compound COC([O-])=O.CC[N+](C)(C)C QSPNICWOGNKGSW-UHFFFAOYSA-M 0.000 description 1
- OCRBIIUIIUDBTL-UHFFFAOYSA-N ethylazanium;methyl carbonate Chemical compound CC[NH3+].COC([O-])=O OCRBIIUIIUDBTL-UHFFFAOYSA-N 0.000 description 1
- YOMFVLRTMZWACQ-UHFFFAOYSA-N ethyltrimethylammonium Chemical compound CC[N+](C)(C)C YOMFVLRTMZWACQ-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- XWQNMWZQUXUMKJ-UHFFFAOYSA-M methyl carbonate tetrapropylazanium Chemical compound COC([O-])=O.CCC[N+](CCC)(CCC)CCC XWQNMWZQUXUMKJ-UHFFFAOYSA-M 0.000 description 1
- WJKZTELBRDUZPO-UHFFFAOYSA-M methyl carbonate;tetrabutylazanium Chemical compound COC([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC WJKZTELBRDUZPO-UHFFFAOYSA-M 0.000 description 1
- KROCSLWRPISNQV-UHFFFAOYSA-M methyl carbonate;tetraethylazanium Chemical compound COC([O-])=O.CC[N+](CC)(CC)CC KROCSLWRPISNQV-UHFFFAOYSA-M 0.000 description 1
- YKLKUNBKAPXTEZ-UHFFFAOYSA-M methyl carbonate;tetramethylazanium Chemical compound COC([O-])=O.C[N+](C)(C)C YKLKUNBKAPXTEZ-UHFFFAOYSA-M 0.000 description 1
- WBUMLCSOSWGRSZ-UHFFFAOYSA-M methyl carbonate;trimethyl(propyl)azanium Chemical compound COC([O-])=O.CCC[N+](C)(C)C WBUMLCSOSWGRSZ-UHFFFAOYSA-M 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- RCVRMFKFWLKGMC-UHFFFAOYSA-M phenyl carbonate;tetramethylazanium Chemical compound C[N+](C)(C)C.[O-]C(=O)OC1=CC=CC=C1 RCVRMFKFWLKGMC-UHFFFAOYSA-M 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- FAJJNVLASATDOW-UHFFFAOYSA-M propyl carbonate;trimethyl(propyl)azanium Chemical compound CCCOC([O-])=O.CCC[N+](C)(C)C FAJJNVLASATDOW-UHFFFAOYSA-M 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、第四級アンモニウム重炭酸塩の製造方法に関
する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a method for producing quaternary ammonium bicarbonate.
第四級アンモニウム重炭酸塩は、界面活性剤として、ま
た界面活性剤の原料として広く使用されており、あるい
は医薬品、化粧品の原料としても有用なものである。Quaternary ammonium bicarbonate is widely used as a surfactant and as a raw material for surfactants, and is also useful as a raw material for pharmaceuticals and cosmetics.
近年、第四級アンモニウム重炭酸塩から誘導される第四
級アンモニウム水酸化物は電子工業、半導体産業におい
てＩＣ，ＬＳＩなどの製造工程でウェハーの洗浄液、エ
ツチング液、現像液などへと多岐にわたり使用されてい
る。In recent years, quaternary ammonium hydroxide derived from quaternary ammonium bicarbonate has been used in a wide range of applications such as wafer cleaning solutions, etching solutions, and developing solutions in the manufacturing process of ICs and LSIs in the electronics and semiconductor industries. has been done.
本発明にかかる第四級アンモニウム重炭酸塩は、一般に
例えば（１１第四級アンモニウム水酸化物を炭酸化する
か、あるいは（２）第四級アンモニウムクロライドに炭
酸ガスとアンモニア水とを反応させることにより得るこ
とができる。The quaternary ammonium bicarbonate according to the present invention can generally be produced by, for example, (11) carbonating quaternary ammonium hydroxide, or (2) reacting quaternary ammonium chloride with carbon dioxide gas and aqueous ammonia. It can be obtained by
しかし、上記の（１）の方法は工業的には実用的でなく
、又（２）の方法は反応工程が煩雑でまた副生物が多い
などの問題点がある。However, the above method (1) is not industrially practical, and the method (2) has problems such as complicated reaction steps and many by-products.
本発明は、上記の現状に鑑み、純度の高い第四級アンモ
ニウム重炭酸塩を製造する方法を提供するにある。In view of the above-mentioned current situation, the present invention provides a method for producing highly pure quaternary ammonium bicarbonate.
本発明者らは、上記した問題点を解決すべく種々の検討
を行った結果、第四級アンモニウムアルキルあるいはモ
ノアリール炭酸塩と水とを反応させることにより目的と
する第四級アンモニウム重炭酸塩を製造する方法を見出
した。As a result of various studies to solve the above-mentioned problems, the present inventors have discovered that the desired quaternary ammonium bicarbonate can be produced by reacting a quaternary ammonium alkyl or monoaryl carbonate with water. discovered a method of manufacturing.
すなわち、本発明は、第四級アンモニウムモノアルキル
あるいはモノアリール炭酸塩と水とを反応させることを
特徴とする第四級アンモニウム重炭酸塩の製造方法に関
する。That is, the present invention relates to a method for producing a quaternary ammonium bicarbonate, which comprises reacting a quaternary ammonium monoalkyl or monoaryl carbonate with water.
本発明の方法は下記式で表される。The method of the present invention is represented by the following formula.
Ｒ１
本発明に用いられる第四級アンモニウムモノアルキルあ
るいはモノアリール炭酸塩は一般式で表される（式中、
Ｒ，、Ｒ，、Ｒ，はＣ１〜Ｃ６のアルキル基、アルケニ
ル基、フェニル基、ベンジル基ヲ示し、式中Ｒ４，Ｒｓ
はｃ、ｘ（：ｅのアルキル基または了り−ル基を示す）
。具体的には、テトラメチルアンモニウム−メチル炭酸
塩、テトラメチルアンモニウム−エチル炭酸塩、テトラ
メチルアンモニウム−イソプロピル炭酸塩、 テトラメ
チルアンモニウム−ｎ−ブチル炭酸塩、テトラメチルア
ンモニウム−フェニル炭酸塩、テトラメチルアンモニウ
ム−ベンジル炭酸塩、テトラエチルアンモニウム−メチ
ル炭酸塩、テトラエチルアンモニウム−エチル炭酸塩、
テトラプロピルアンモニウム−メチル炭酸塩、テトラブ
チルアンモニウム−メチル炭酸塩、トリメチルエチルア
ンモニウム−メチル炭酸塩、トリメチルプロピルアンモ
ニウム−メチル炭酸塩、トリメチルプロピルアンモニウ
ム−プロピル炭酸塩、トリメチルベンジルアンモニウム
−メチル炭酸塩、トリメチルヒドロキシエチルアンモニ
ウム−メチル炭酸塩、トリメチルメトキシエチルアンモ
ニウム−メチル炭酸塩、トリノチルエチルアンモニウム
ーベンジル炭酸塩、ジメチルジエチルアンモニウム−メ
チル炭酸塩、等が例示される。R1 The quaternary ammonium monoalkyl or monoaryl carbonate used in the present invention is represented by the general formula (in the formula,
R,,R,,R,represents a C1 to C6 alkyl group, alkenyl group, phenyl group, or benzyl group, and in the formula, R4,Rs
is c, x (represents an alkyl group or an alkyl group of e)
. Specifically, tetramethylammonium-methyl carbonate, tetramethylammonium-ethyl carbonate, tetramethylammonium-isopropyl carbonate, tetramethylammonium-n-butyl carbonate, tetramethylammonium-phenyl carbonate, tetramethylammonium -benzyl carbonate, tetraethylammonium-methyl carbonate, tetraethylammonium-ethyl carbonate,
Tetrapropylammonium-methyl carbonate, tetrabutylammonium-methyl carbonate, trimethylethylammonium-methyl carbonate, trimethylpropylammonium-methyl carbonate, trimethylpropylammonium-propyl carbonate, trimethylbenzylammonium-methyl carbonate, trimethyl hydroxy Examples include ethyl ammonium-methyl carbonate, trimethylmethoxyethylammonium-methyl carbonate, trinotylethylammonium-benzyl carbonate, dimethyldiethylammonium-methyl carbonate, and the like.
この様な第四級アンモニウムモノアルキル炭酸塩あるい
はモノアリール炭酸塩は、例えば、米国特許第２６３５
１００号に示されるように、アルコール等の極性溶媒の
存在下または非存在下に炭酸ジアルキルあるいは炭酸ジ
アリールと第三級アミンとを反応させることにより容易
に得ることができる。Such quaternary ammonium monoalkyl carbonates or monoaryl carbonates are described, for example, in US Pat.
As shown in No. 100, it can be easily obtained by reacting dialkyl carbonate or diaryl carbonate with a tertiary amine in the presence or absence of a polar solvent such as alcohol.
本発明において、水は反応原料であると共に、反応溶媒
として作用するので、−ａ的に使用する第四級アンモニ
ウムアルキル炭酸塩あるいはモノアリール炭酸塩に対し
て理論量以上使用され、好ましくは２〜３０倍（モル）
である。従って水は過剰に使用されるが、余りにも多量
であると反応後の分離、除去に時間を要するので得策で
ない。In the present invention, water is a reaction raw material and also acts as a reaction solvent, so it is used in a stoichiometric amount or more with respect to the quaternary ammonium alkyl carbonate or monoaryl carbonate used as -a, preferably 2 to 30 times (mol)
It is. Therefore, water is used in excess, but too much water is not a good idea since it takes time to separate and remove it after the reaction.
本発明の方法においては、アルコール類、ニトリル類、
酸アミド類等の極性溶媒を使用することができる。極性
溶媒を使用することにより、反応初期の反応速度を高め
ることができ全体の反応を短時間に行うことができる。In the method of the present invention, alcohols, nitriles,
Polar solvents such as acid amides can be used. By using a polar solvent, the reaction rate at the initial stage of the reaction can be increased and the entire reaction can be carried out in a short time.
さらに反応収率を高める効果もある。Furthermore, it has the effect of increasing the reaction yield.
この様な極性溶媒としては、例えば、メタノール、エタ
ノール、プロパツール、等の脂肪族低級アルコール類、
ベンアルアルコールの様な一価芳香族アルコール、エチ
レングリコールの様なグリコール類、Ｎ、Ｎ−ジメチル
ホルムアミドの様な酸アミド類、アセトニトリルの様な
ニトリル類が例示されるが、これら極性溶媒はその沸点
が余り高くないものが好ましく、沸点５０〜２００℃の
範囲にあるものがよ（、好ましくはメタノール、エタノ
ール、プロパツール、アセトニトリル等が反応後の分離
操作などの点から好適である。Examples of such polar solvents include aliphatic lower alcohols such as methanol, ethanol, propatool, etc.
Examples include monohydric aromatic alcohols such as ben-alcohol, glycols such as ethylene glycol, acid amides such as N,N-dimethylformamide, and nitrites such as acetonitrile. It is preferable that the boiling point is not too high, preferably in the range of 50 to 200° C. (Preferably, methanol, ethanol, propatool, acetonitrile, etc. are suitable from the viewpoint of separation operation after the reaction, etc.).
これら極性溶媒の使用量は原料第四級アンモニウムモノ
アルキル炭酸塩あるいはモノアリール炭酸塩に対して０
．５〜３０倍量（重量）であり、通常は１〜２０倍量、
好ましくは２〜１０倍量が使用される本発明の方法を実
施する際の反応温度は、 ｍ的には３０〜３００℃の範
囲であるが、実際には反応速度、原料の第四級アンモニ
ウムモノアルキル炭酸塩あるいはモノアリール炭酸塩お
よび目的物の第四級アンモニウム重炭酸塩の分解等を考
慮する必要があり、通常は４０〜２５０℃好ましくは５
０〜２００℃である。The amount of these polar solvents used is 0 based on the raw material quaternary ammonium monoalkyl carbonate or monoaryl carbonate.
．． 5 to 30 times the amount (weight), usually 1 to 20 times the amount,
The reaction temperature when carrying out the method of the present invention, which is preferably used in an amount of 2 to 10 times, is in the range of 30 to 300°C, but in reality, the reaction rate It is necessary to take into consideration the decomposition of monoalkyl carbonates or monoaryl carbonates and the target quaternary ammonium bicarbonate, and the temperature is usually 40 to 250°C, preferably 5°C.
The temperature is 0 to 200°C.
なお、本発明は、必要に応じて、窒素、アルゴンヘリウ
ム、あるいは水素ガス等の反応に影響を与えない不活性
ガス雰囲気下で反応させることもできる。 又、本発明
は回分式、半回分式あるいは連続式何れの方法でも実施
し得る。In addition, in the present invention, the reaction can be carried out under an atmosphere of an inert gas that does not affect the reaction, such as nitrogen, argon helium, or hydrogen gas, if necessary. Furthermore, the present invention can be carried out in any of the batch, semi-batch or continuous methods.
本発明は、炭酸ジアルキルあるいは炭酸ジアリールと第
三級アミンとから得られる第四級アンモニウムモノアル
キル炭酸塩あるいはモノアリール炭酸塩と水とを反応さ
せることにより第四級アンモニウム重炭酸塩の製造を高
収率で行うことができる新規な方法でり、工業的にきわ
めて有意義な方法である。The present invention improves the production of quaternary ammonium bicarbonate by reacting a quaternary ammonium monoalkyl carbonate or monoaryl carbonate obtained from a dialkyl or diaryl carbonate and a tertiary amine with water. This is a new method that can be carried out with high yield, and is an extremely meaningful method industrially.
以下に本発明の実施例を示す。Examples of the present invention are shown below.
実施例 １゜
３００ｍ ｌの内容積のオートクレーブに、テトラメチ
ルアンモニウム七ツメチル炭酸塩１０８．０ｇ、水７２
．０ｇ、を導入し、加熱、攪拌した。反応器内の温度が
１００℃に達した後その温度で３時間反応を継続させた
。反応終了後、生成物を分析した結果、テトラメチルア
ンモニウム重炭酸塩が９６．７χ（モル）の収率で得ら
れた。Example 1 In an autoclave with an internal volume of 300 ml, 108.0 g of tetramethylammonium 7-methyl carbonate and 72 g of water were added.
．． 0 g was introduced, heated and stirred. After the temperature inside the reactor reached 100°C, the reaction was continued at that temperature for 3 hours. After the reaction was completed, the product was analyzed, and as a result, tetramethylammonium bicarbonate was obtained in a yield of 96.7χ (mol).
実施例 ２
実施例１で使用したと同様の反応器に、テトラメチルア
ンモニウムモメチル炭酸塩８６．４ｇ、水９３゜６ｇ、
を導入し、加熱攪拌した。反応器内の温度が１００℃に
達した後その温度で３時間反応を継続させた。反応終了
後、生成物を分析した結果、テトラメチルアンモニウム
重炭酸塩が９７．１χ（モル）の収率で得られた。Example 2 In a reactor similar to that used in Example 1, 86.4 g of tetramethylammonium momethyl carbonate, 93.6 g of water,
was introduced and heated and stirred. After the temperature inside the reactor reached 100°C, the reaction was continued at that temperature for 3 hours. After the reaction was completed, the product was analyzed and it was found that tetramethylammonium bicarbonate was obtained in a yield of 97.1x (mol).
実施例 ３
実施例１で使用したと同様の反応器に、テトラメチルア
ンモニウムモメチル炭酸塩１０８．０ｇ 、水７２．０
ｇ 、メタノール３２．０ｇを導入し、加熱攪拌した。Example 3 In a reactor similar to that used in Example 1, 108.0 g of tetramethylammonium momethyl carbonate and 72.0 g of water were added.
32.0 g of methanol were introduced, and the mixture was heated and stirred.
反応器内の温度が１００℃に達した後その温度で３時間
反応を継続させた。反応終了後、生成物を分析した結果
、テトラメチルアンモニウム重炭酸塩が９８．５χ（モ
ル）の収率で得られた。After the temperature inside the reactor reached 100°C, the reaction was continued at that temperature for 3 hours. After the reaction was completed, the product was analyzed and it was found that tetramethylammonium bicarbonate was obtained in a yield of 98.5x (mol).
実施例 ４
実施例１で使用したと同様の反応器に、トリメチルエチ
ルアンモニウムモメチル炭酸塩１１４．１ｇ。Example 4 In a reactor similar to that used in Example 1, 114.1 g of trimethylethylammonium momethyl carbonate.
水７５．６ｇ、を導入し、加熱攪拌した。反応器内の温
度が１２０℃に達した後その温度で３時間反応を継続さ
せた。反応終了後、生成物を分析した結果トリメチルエ
チルアンモニウム重炭酸塩が９６，３χ（モル）の収率
で得られた。75.6 g of water was introduced, and the mixture was heated and stirred. After the temperature inside the reactor reached 120°C, the reaction was continued at that temperature for 3 hours. After the reaction was completed, the product was analyzed and trimethylethylammonium bicarbonate was obtained in a yield of 96.3 x (mol).
実施例 ５
実施例１で使用したと同様の反応器に、テトラメチルア
ンモニウム−イソプロピル炭ｐ塩８８．５ｇ水４５．Ｏ
ｇ、を導入し、加熱攪拌した。反応器内の温度が１２０
℃に達した後その温度で３時間反応を継続させた。反応
終了後、生成物を分析した結果テトラメチルアンモニウ
ム重炭酸塩が９５．０χ（モル）の収率で得られた。Example 5 In a reactor similar to that used in Example 1, 88.5 g of tetramethylammonium-isopropyl carbonate salt were added 45.5 g of water. O
g, and heated and stirred. The temperature inside the reactor is 120
After reaching °C, the reaction was continued at that temperature for 3 hours. After the reaction was completed, the product was analyzed and it was found that tetramethylammonium bicarbonate was obtained in a yield of 95.0x (mol).
実施例 ６
実施例１で使用したと同様の反応器に、トリメチルベン
ジルアンモニウムモメチル炭酸Ｊｆｌ １１２．５ｇ、
水５５．０ｇ、を導入し、加熱攪拌した。反応器内の温
度が１２０℃に達した後その温度で３時間反応を継続さ
せた。反応終了後、生成物を分析した結果トリメチルベ
ンジルアンモニウム重炭酸塩が９５゜７χ（モル）の収
率で得られた。Example 6 In a reactor similar to that used in Example 1, 112.5 g of trimethylbenzylammonium momethyl carbonate Jfl,
55.0 g of water was introduced, and the mixture was heated and stirred. After the temperature inside the reactor reached 120°C, the reaction was continued at that temperature for 3 hours. After the reaction was completed, the product was analyzed and trimethylbenzylammonium bicarbonate was obtained in a yield of 95.7x (mol).
Claims (1)
炭酸塩と水とを反応させることを特徴とする第四級アン
モニウム重炭酸塩の製造方法A method for producing a quaternary ammonium bicarbonate, which comprises reacting a quaternary ammonium monoalkyl or monoaryl carbonate with water.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27875586A JPH0742256B2 (en) | 1986-11-25 | 1986-11-25 | Method for producing quaternary ammonium bicarbonate |
| US07/120,150 US4776929A (en) | 1986-11-25 | 1987-11-12 | Process for production of quaternary ammonium hydroxides |
| EP87117020A EP0269949B1 (en) | 1986-11-25 | 1987-11-18 | Process for producing a high purity quaternary ammonium hydroxide |
| DE87117020T DE3785548T2 (en) | 1986-11-25 | 1987-11-18 | Process for the production of a high-purity quaternary ammonium hydroxide. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27875586A JPH0742256B2 (en) | 1986-11-25 | 1986-11-25 | Method for producing quaternary ammonium bicarbonate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63132863A true JPS63132863A (en) | 1988-06-04 |
| JPH0742256B2 JPH0742256B2 (en) | 1995-05-10 |
Family
ID=17601743
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP27875586A Expired - Lifetime JPH0742256B2 (en) | 1986-11-25 | 1986-11-25 | Method for producing quaternary ammonium bicarbonate |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0742256B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005029715A (en) * | 2003-07-08 | 2005-02-03 | National Institute Of Advanced Industrial & Technology | Method for producing bio-diesel fuel |
| EP2522682A1 (en) | 2005-03-15 | 2012-11-14 | Polyplastics Co., Ltd. | Unstable terminal group decomposer, and stabilized polyacetal resin, manufacturing method, composition and molded article using the same |
-
1986
- 1986-11-25 JP JP27875586A patent/JPH0742256B2/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005029715A (en) * | 2003-07-08 | 2005-02-03 | National Institute Of Advanced Industrial & Technology | Method for producing bio-diesel fuel |
| EP2522682A1 (en) | 2005-03-15 | 2012-11-14 | Polyplastics Co., Ltd. | Unstable terminal group decomposer, and stabilized polyacetal resin, manufacturing method, composition and molded article using the same |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0742256B2 (en) | 1995-05-10 |
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