JPH0283367A - Novel mercapto compound and production thereof - Google Patents
Novel mercapto compound and production thereofInfo
- Publication number
- JPH0283367A JPH0283367A JP23379288A JP23379288A JPH0283367A JP H0283367 A JPH0283367 A JP H0283367A JP 23379288 A JP23379288 A JP 23379288A JP 23379288 A JP23379288 A JP 23379288A JP H0283367 A JPH0283367 A JP H0283367A
- Authority
- JP
- Japan
- Prior art keywords
- carbon atoms
- alkali
- mercapto compound
- alkyl
- formula
- 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.)
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- 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）
本発明は新規メルカプト化合物およびその製造方法に関
する。DETAILED DESCRIPTION OF THE INVENTION (Industrial Application Field) The present invention relates to a novel mercapto compound and a method for producing the same.
（従来の技術）
本発明の一般式（Ｉ）に属するようなメルカプト化合物
に関する報告は従来なく、かかる化合物は新規である。(Prior Art) There has been no report on a mercapto compound belonging to the general formula (I) of the present invention, and such a compound is new.
（発明が解決しようとする課題）
本発明の目的は新規メルカプト化合物およびその製造方
法を提供することにある。(Problems to be Solved by the Invention) An object of the present invention is to provide a novel mercapto compound and a method for producing the same.
（課題を解決するための手段）
本発明は一般式（Ｉ）
（式中、Ｒ１は炭素数１〜２０のアルキル基または炭素
数１〜３のヒドロキシアルキル基、Ｒ２及びＲ３は炭素
数１〜３のアルキル基または炭素数１〜３のヒドロキシ
アルキル基を示し、Ｘはハロゲン原子を示す、）
で表わされる新規メルカプト化合物およびその製造方法
に関する。(Means for Solving the Problems) The present invention is based on the general formula (I) (wherein R1 is an alkyl group having 1 to 20 carbon atoms or a hydroxyalkyl group having 1 to 3 carbon atoms, and R2 and R3 are 3 alkyl group or a hydroxyalkyl group having 1 to 3 carbon atoms, and X represents a halogen atom) and a method for producing the same.
本発明の新規メルカプト化合物としては、具体的には２
−メルカプトエチル−トリメチルアンモニウムクロライ
ド、２−メルカプトエチル−ジメチルエチルアンモニウ
ムクロライド、２−メルカプトエチル−ジメチルプロピ
ルアンモニウムクロライド、２−メルカプトエチル−ジ
メチルブチルアンモニウムクロライド、２−メルカプト
エチル−ジメチルオクチルアンモニウムブロマイド、２
メルカプトエチル−ジエチルラウリルアンモニウムブロ
マイド、２−メルカプトエチル−トリヒドロキシエチル
アンモニウムクロライド、２−メルカプトエチル−トリ
２−ヒドロキシプロピルアンモニウムクロライド等が挙
げられる。Specifically, the novel mercapto compounds of the present invention include 2
-Mercaptoethyl-trimethylammonium chloride, 2-mercaptoethyl-dimethylethylammonium chloride, 2-mercaptoethyl-dimethylpropylammonium chloride, 2-mercaptoethyl-dimethylbutylammonium chloride, 2-mercaptoethyl-dimethyloctylammonium bromide, 2
Examples include mercaptoethyl-diethyl lauryl ammonium bromide, 2-mercaptoethyl-trihydroxyethylammonium chloride, 2-mercaptoethyl-tri2-hydroxypropylammonium chloride, and the like.
さらに、本発明者等は前記−数式（Ｉ）で示される化合
物は以下の方法で容易に製造できることを見い出した。Furthermore, the present inventors have discovered that the compound represented by formula (I) above can be easily produced by the following method.
（１）システアミン又はシステアミン塩を溶媒中でアル
カリの存在下、１０〜１００°Ｃ５常圧又は加圧下で炭
素数１〜２０のハロゲン化アルキル及び炭素数１〜３の
ハロゲン化アルキルとを反応させることにより前記−数
式（Ｉ）で示されるメルカプト化合物を製造することが
できる。(1) Cysteamine or cysteamine salt is reacted with an alkyl halide having 1 to 20 carbon atoms and an alkyl halide having 1 to 3 carbon atoms in a solvent in the presence of an alkali at 10 to 100° C5 under normal pressure or pressure. By doing so, the mercapto compound represented by the above formula (I) can be produced.
本発明で用いる溶媒としては、メタノール、エタノール
、ｎ−プロパツール、ｌ５Ｏ−１０パノール等の低級ア
ルコールが好ましい。As the solvent used in the present invention, lower alcohols such as methanol, ethanol, n-propanol, and 15O-10 panol are preferred.
またアルカリは、ナトリウムメチラート、ナトリウムエ
チラート等のアルカリ金属アルコラード又は水酸化ナト
リウム、水酸化カリウム等のアルカリ金属水酸化物が好
ましい、又システアミン塩は塩酸塩、硫酸塩等を用いる
ことができる。Further, the alkali is preferably an alkali metal alcoholade such as sodium methylate or sodium ethylate, or an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide, and the cysteamine salt may be a hydrochloride, a sulfate, or the like.
（２）ジメチルチアゾリジンを、溶媒中アルカリの存在
下、１０〜１００℃常圧又は加圧下で炭素数１〜２０の
ハロゲン化アルキルと反応させた後、塩酸又は硫酸等の
鉱酸を加え、５０〜１５０℃に加熱することによりチア
ゾリジン環を開環させ、これにアルカリを加え、２０〜
１００℃、常圧又は加圧下で炭素数１〜３のハロゲン化
アルキルを反応させることにより前記−数式（Ｉ）で示
されるメルカプト化合物を製造することができる。(2) Dimethylthiazolidine is reacted with an alkyl halide having 1 to 20 carbon atoms in the presence of an alkali in a solvent at 10 to 100°C under normal pressure or pressure, then a mineral acid such as hydrochloric acid or sulfuric acid is added, The thiazolidine ring is opened by heating to ~150°C, an alkali is added to this, and the thiazolidine ring is heated to ~150°C.
The mercapto compound represented by formula (I) above can be produced by reacting an alkyl halide having 1 to 3 carbon atoms at 100° C. under normal pressure or increased pressure.
用いる溶媒としては、メタノール、エタノール、ｎ−プ
ロパツール、１ｓｏ−プロパツール等の低級アルコール
が好ましい、また、アルカリはナトリウムメチラート、
ナトリウムエチラート等のアルカリ金属アルコラード又
は水酸化ナトリウム、水酸化カリウム等のアルカリ金属
水酸化物が好ましい。As the solvent used, lower alcohols such as methanol, ethanol, n-propanol, and 1so-propanol are preferable, and the alkali is sodium methylate,
Alkali metal alcoholades such as sodium ethylate or alkali metal hydroxides such as sodium hydroxide and potassium hydroxide are preferred.
（発明の効果）
本発明の一般式（Ｉ）
（式中、Ｒ１は炭素数１〜２０のアルキル基または炭素
数１〜３のヒドロキシアルキル基、Ｒ２及びＲ３は炭素
数１〜３のアルキル基または炭素数１〜３のヒドロキシ
アルキル基を示し、Ｘはハロゲン原子を示す、）
で表わされる新規メルカプト化合物は簡便に製造できる
ようになった。(Effects of the Invention) General formula (I) of the present invention (wherein, R1 is an alkyl group having 1 to 20 carbon atoms or a hydroxyalkyl group having 1 to 3 carbon atoms, and R2 and R3 are alkyl groups having 1 to 3 carbon atoms. or represents a hydroxyalkyl group having 1 to 3 carbon atoms, and X represents a halogen atom) A new mercapto compound represented by the following can now be easily produced.
（実施例）
以下、実施例に従って、本発明を更に具体的に説明する
が、本発明の範囲をこれらの実施例に限定するものでは
ない。(Examples) Hereinafter, the present invention will be explained in more detail according to Examples, but the scope of the present invention is not limited to these Examples.
実施例１
温度計、撹拌装置及び冷却器を備えた反応器にメタノー
ル１９５ｇ、２８％ナトリウムメチラートメタノール溶
１１９０ｇ、ジメチルチアゾリジン１１７ｇを加えて混
合し、これに撹拌下１０’Ｃで臭化ラウリル２４９．２
ｇを添加し、その後５０℃で２時間反応を継続した。析
出した結晶をろ別した後、得られたろ液に３６％Ｈｃｒ
ｔｏｉ。Example 1 195 g of methanol, 1190 g of 28% sodium methylate methanol solution, and 117 g of dimethylthiazolidine were added to a reactor equipped with a thermometer, a stirring device, and a condenser, and mixed, and 249 g of lauryl bromide was added at 10'C with stirring. .2
g was added, and the reaction was then continued at 50° C. for 2 hours. After filtering out the precipitated crystals, 36% Hcr was added to the obtained filtrate.
toi.
３ｇを加え、２時間還流し、チアゾリジン環を開環させ
た。これに４０％水酸化ナトリウム水溶液１００ｇを冷
却しながら添加した後、有機層を分取し、これに２８％
ナトリウムメチラートメタノール溶液１９０ｒを加え、
撹拌下１０°Ｃで臭化エチル２７３ｇを添加し、３０℃
で５時間反応を継続した。軽質分を減圧上蒸留除去し、
１ｓｏ−プロパツールに再溶解させ、不溶の無機塩を除
去した後、ＳＯ−プロパツールを減圧加熱して除去し、
２−メルカプトエチル−ジエチルラウリルアンモニウム
ブロマイドの淡黄色透明な液体３０２ｇを得た。3 g was added and refluxed for 2 hours to open the thiazolidine ring. After adding 100 g of 40% sodium hydroxide aqueous solution to this while cooling, the organic layer was separated and added to 28%
Add 190 r of sodium methylate methanol solution,
273 g of ethyl bromide was added at 10°C with stirring, and the mixture was heated to 30°C.
The reaction was continued for 5 hours. Light components are removed by distillation under reduced pressure.
After redissolving in 1so-propertool and removing insoluble inorganic salts, SO-propertool is removed by heating under reduced pressure,
302 g of a pale yellow transparent liquid of 2-mercaptoethyl-diethyl lauryl ammonium bromide was obtained.
得られた液体の元素分析結果は以下の通りであった。The results of elemental analysis of the obtained liquid were as follows.
ＣＡ Ｈ２ｉ 反χ 針
計算値 ５６．５１ １０．５１！ ３．６８ ８．
３８実測値 ５６．４０ １０．４５ ３．７１ ８．
２５第１図にこの液体の赤外吸収スペクトルを示したが
、第１図のスペクトルには２５８０ａｎ−１及び２５４
０ａｎ にＨ３伸縮振動、１３８０ａａ−’に４級ア
ンモニウム塩に起因するＣＮ伸縮振動が特徴的なシグナ
ルとして観察される。CA H2i anti-χ needle calculation value 56.51 10.51! 3.68 8.
38 Actual value 56.40 10.45 3.71 8.
25 Figure 1 shows the infrared absorption spectrum of this liquid.
H3 stretching vibration at 0an and CN stretching vibration caused by the quaternary ammonium salt at 1380aa-' are observed as characteristic signals.
さらに第２図にこの液体の１Ｈ−ＮＭＲ（７ＭＳ標準）
スペクトルを示したが、各ピークのシフト値は以下のよ
うに帰属された。Furthermore, Fig. 2 shows the 1H-NMR (7MS standard) of this liquid.
The spectrum was shown, and the shift values of each peak were assigned as follows.
１３Ｅ
Ｉｔｓ−ＣＨ２−ＣＨ２−Ｎ−ＣＨ２−（ＣＩ＋２）
１ｏ−ＣＨ３八 ＢＣＩＦ Ｇ１
１Ｃ■２Ｄ
１１３Ｅ
Ａ １．７ＰＰＭ Ｄ ２．６ＰＰＭ
Ｇ １．３ＰＰＨＢ ２．６ＰＰＨＥ １．
ＯＰＰＭ １１ ０．９ＰＰ１４Ｃ２，６ＰＰＭ
Ｆ ２．６ＰＰＭ実施例２
温度計、撹拌装置及び冷却器を備えた反応器にメタノー
ル１９５ｇ、システアミン塩酸塩１１３゜５ｇ加えて混
合し、これに撹拌下１０″Ｃで２８％ナトリウムメチラ
ートメタノール溶１５７０．を添加し、続いて臭化ラウ
リル２４９．２ｆを添加し、５０℃で２時間反応を継続
しな、いったん冷却し、１０℃にて臭化エチル２７３ｇ
を添加し、３０℃で５時間反応を継続した。軽質分を減
圧下、蒸留除去し、１ｓｏ−プロパツールに再溶解させ
、不溶の無機塩を除去した後、１ｓｏ−プロパツールを
減圧加熱して除去し、２−メルカプトエチル−ジエチル
ラウリルアンモニウムブロマイドの淡黄色透明な液体３
１５ｇを得た。13E Its-CH2-CH2-N-CH2-(CI+2)
1o-CH38 BCIF G1
1C■2D 113E A 1.7PPM D 2.6PPM
G 1.3PPHB 2.6PPHE 1.
OPPM 11 0.9PP14C2,6PPM
F 2.6 PPM Example 2 195 g of methanol and 113.5 g of cysteamine hydrochloride were added to a reactor equipped with a thermometer, a stirrer, and a condenser and mixed, and a 28% sodium methylate methanol solution was added to this at 10"C with stirring. 1570. was added, followed by 249.2f of lauryl bromide, and the reaction was continued at 50°C for 2 hours. Once cooled, 273g of ethyl bromide was added at 10°C.
was added, and the reaction was continued at 30°C for 5 hours. Light components were removed by distillation under reduced pressure, redissolved in 1so-propatol, and insoluble inorganic salts were removed.The 1so-propatol was then removed by heating under reduced pressure to form 2-mercaptoethyl-diethyllauryl ammonium bromide. Pale yellow transparent liquid 3
15g was obtained.
第１図は実施例１で得られた２−メルカプトエチル−ジ
エチルラウリルアンモニウムブロマイドの赤外吸収スペ
クトルを示す図面である。FIG. 1 is a drawing showing an infrared absorption spectrum of 2-mercaptoethyl-diethyl lauryl ammonium bromide obtained in Example 1.
Claims (3)
素数１〜３のヒドロキシアルキル基、Ｒ＿２及びＲ＿３
は炭素数１〜３のアルキル基または炭素数１〜３のヒド
ロキシアルキル基を示し、Ｘはハロゲン原子を示す。） で表わされる新規メルカプト化合物。(1) General formula (I) ▲Mathematical formulas, chemical formulas, tables, etc.▼... (I) (In the formula, R_1 is an alkyl group with 1 to 20 carbon atoms or a hydroxyalkyl group with 1 to 3 carbon atoms, R_2 and R_3
represents an alkyl group having 1 to 3 carbon atoms or a hydroxyalkyl group having 1 to 3 carbon atoms, and X represents a halogen atom. ) A new mercapto compound represented by
０のハロゲン化アルキル及び炭素数１〜３のハロゲン化
アルキルとを溶媒中、アルカリの存在下で反応させるこ
とを特徴とする新規メルカプト化合物の製造方法。(2) Cysteamine or cysteamine salt and carbon number 1-2
1. A method for producing a novel mercapto compound, which comprises reacting an alkyl halide of 0 and an alkyl halide having 1 to 3 carbon atoms in a solvent in the presence of an alkali.
ン化アルキルとを溶媒中アルカリの存在下で反応させ、
これに酸を加えてチアゾリジン環を開環した後、アルカ
リを加え、炭素数１〜３のハロゲン化アルキルとを反応
させることを特徴とする新規メルカプト化合物の製造方
法。(3) reacting dimethylthiazolidine with an alkyl halide having 1 to 20 carbon atoms in a solvent in the presence of an alkali,
A method for producing a novel mercapto compound, which comprises adding an acid to the thiazolidine ring to open the thiazolidine ring, and then adding an alkali to react with an alkyl halide having 1 to 3 carbon atoms.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63233792A JP2522823B2 (en) | 1988-09-20 | 1988-09-20 | Novel mercapto compound and method for producing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63233792A JP2522823B2 (en) | 1988-09-20 | 1988-09-20 | Novel mercapto compound and method for producing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0283367A true JPH0283367A (en) | 1990-03-23 |
| JP2522823B2 JP2522823B2 (en) | 1996-08-07 |
Family
ID=16960641
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63233792A Expired - Lifetime JP2522823B2 (en) | 1988-09-20 | 1988-09-20 | Novel mercapto compound and method for producing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2522823B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7757671B2 (en) | 2006-09-29 | 2010-07-20 | Denso Corporation | Fuel feed apparatus |
-
1988
- 1988-09-20 JP JP63233792A patent/JP2522823B2/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7757671B2 (en) | 2006-09-29 | 2010-07-20 | Denso Corporation | Fuel feed apparatus |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2522823B2 (en) | 1996-08-07 |
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