JPS647982B2 - - Google Patents
Info
- Publication number
- JPS647982B2 JPS647982B2 JP56142332A JP14233281A JPS647982B2 JP S647982 B2 JPS647982 B2 JP S647982B2 JP 56142332 A JP56142332 A JP 56142332A JP 14233281 A JP14233281 A JP 14233281A JP S647982 B2 JPS647982 B2 JP S647982B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- temperature
- dialkylamine
- carried out
- mol
- 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
Links
- 125000005265 dialkylamine group Chemical group 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 239000003377 acid catalyst Substances 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 9
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- -1 alkylene imine Chemical class 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 150000004985 diamines Chemical class 0.000 description 4
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- OZDGMOYKSFPLSE-UHFFFAOYSA-N 2-Methylaziridine Chemical compound CC1CN1 OZDGMOYKSFPLSE-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 1
- DMDXQHYISPCTGF-UHFFFAOYSA-N n',n'-dipropylethane-1,2-diamine Chemical compound CCCN(CCC)CCN DMDXQHYISPCTGF-UHFFFAOYSA-N 0.000 description 1
- KVKFRMCSXWQSNT-UHFFFAOYSA-N n,n'-dimethylethane-1,2-diamine Chemical compound CNCCNC KVKFRMCSXWQSNT-UHFFFAOYSA-N 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
本発明は、アルキレンイミンとジアルキルアミ
ンとから非対称アルキルアルキレンジアミンの製
造方法に関するものである。
非対称アルキルアルキレンジアミンの製造方法
として、例えば特公昭45−31446号明細書からエ
チレンイミンとジブチルアミンを塩化アルミニウ
ム存在下に反応させる方法、米国特許第2318729
号（1943）明細書から水溶媒中で両者を反応させ
る方法が知られている。しかし、前者方法では多
量の塩化アルミニウムを必要とするうえ精製工程
でそれを除去する必要があるなどの欠点があり、
また後者方法では収率が低いという重大な欠点を
持つている。
本発明者らは、このような現状に鑑み、アルキ
レンイミンおよびジアルキルアミンを出発原料と
する非対称アルキルアルキレンジアミンの製造方
法について鋭意研究した結果、酸触媒の存在下に
１価の低級アルコール溶媒中特定の反応条件下で
反応させることにより非対称アルキルアルキレン
ジアミンの収率が飛躍的に高くなることを見出し
て、本発明を完成したものである。
本発明の非対称アルキルアルキレンジアミンの
製造方法は、一般式
The present invention relates to a method for producing an asymmetric alkyl alkylene diamine from an alkylene imine and a dialkyl amine. As a method for producing asymmetric alkylalkylene diamines, for example, a method of reacting ethyleneimine and dibutylamine in the presence of aluminum chloride is disclosed in Japanese Patent Publication No. 45-31446, US Patent No. 2318729.
(1943), a method of reacting both in an aqueous solvent is known. However, the former method has drawbacks such as requiring a large amount of aluminum chloride and having to remove it in the refining process.
Moreover, the latter method has a serious drawback of low yield. In view of the current situation, the present inventors have conducted intensive research on a method for producing asymmetric alkylalkylene diamines using alkylene imines and dialkyl amines as starting materials. The present invention was completed by discovering that the yield of asymmetric alkylalkylene diamines can be dramatically increased by carrying out the reaction under the following reaction conditions. The method for producing the asymmetric alkyl alkylene diamine of the present invention has the general formula
【式】 （式中、R1は水素またはメチル基を表わす。） で示されるアルキレンイミンと一般式[Formula] (In the formula, R 1 represents hydrogen or a methyl group.) Alkylene imine and general formula
【式】
（式中、R2は炭素数１〜３個のアルキル基を表
わし、R2とR3は同一または異なる。）
で示されるジアルキルアミンを、前者１モルに対
して後者２〜５モルの比率の量で使用し、密閉系
で、酸触媒の存在下に１価の脂肪族低級アルコー
ル溶媒中90〜150℃の範囲の温度で反応させるこ
とを特徴とする。
そして、当該反応を、酸触媒、ジアルキルアミ
ンおよび１価の脂肪族低級アルコールから成り90
〜150℃の範囲の温度に保たれた混合物にアルキ
レンイミンを連続的または間歇的に添加して、必
要に応じて当該添加終了後も反応系を当該温度に
維持して、行なわせることにより非対称アルキル
アルキレンジアミンの収率を飛躍的に高くでき
る。
本発明におけるアルキレンイミンは、前記一般
式で示されるもので、例えばエチレンイミンおよ
びプロピレンイミンを挙げることができ、１種ま
たは２種の混合物として使用できる。ジアルキル
アミンは、前記一般式で示されるもので、例えば
ジメチルアミン、ジエチルアミン、ジプロピルア
ミンなどを挙げることができ、１種または２種以
上の混合物として使用できる。酸触媒として、
種々の酸、例えば塩酸、硫酸などを挙げることが
でき、特に塩酸が好ましく、アルキレンイミンに
対して１〜５モル％の量で使用できる。
本発明における溶媒は、１価の脂肪族低級アル
コールであり、例えばメチルアルコール、エチル
アルコール、プロピルアルコール、イソプロピル
アルコール、ブチルアルコールなどの炭素数１〜
４の脂肪族アルコールを挙げることができ、特に
メチルアルコール、エチルアルコールなどが好ま
しい。溶媒使用量については、反応溶媒として機
能する量であれば良く特に制限ないが、例えば反
応体全量に対して20〜50wt％の量とすることが
できる。溶媒の使用量は必須で、使用しないと目
的物の収率が低下する。
アルキレンイミンとジアルキルアミンとの反応
は、密閉系で、即ち自然発生圧下または外部から
の加圧下に反応温度を90〜150℃、好ましくは100
〜130℃の範囲に保つて行なうことができる。こ
の際、反応温度を90℃未満の低温としたのでは反
応速度が遅く、また逆に150℃を越える高温とし
ても収率向上に寄与せず系の圧力がいたずらに高
くなるだけで技術的意義のないものである。反応
体の全使用量における両者の比率は、アルキレン
イミン１モルに対してジアルキルアミン２〜５モ
ルの比率とするのが適当である。当該比率が２未
満では反応副生物が多くなり目的物の収率が低下
し、逆に５を越えるとジアルキルアミン回収量が
多くなり工業的に有利でない。そして、反応体、
酸触媒および溶媒を一度に反応器に仕込み反応さ
せる方法や酸触媒を含み90〜150℃の範囲の温度
に保たれた溶媒に反応体を連続的または間歇的に
添加し反応させる方法で目的物を得ることができ
るが、酸触媒、ジアルキルアミンおよび溶媒から
成り90〜150℃の範囲の温度に保たれた混合物に
アルキレンイミンを連続的または間歇的に添加し
て、必要に応じて当該添加終了後も反応系を当該
温度に維持して、反応させることにより目的物の
収率を飛躍的に高くできる。
非対称アルキルアルキレンジアミンは、反応生
成物から分留の手順に従つて容易に分離できる。
本発明の製造方法に従えば、簡単な製造工程で
非対称アルキルアルキレンジアミンを高収率で製
造できる。
以下、実施例により本発明を更に詳しく説明す
る。
実施例 １
容量500c.c.のオートクレーブにメチルアルコー
ル90ｇ、ジメチルアミン135ｇ（３モル）および
15wt％塩酸・メチルアルコール溶液7.3ｇを仕込
み、密閉した。110℃に昇温し維持し、撹拌下、
エチレンイミン43ｇ（１モル）を１時間かけて添
加し、添加終了後110℃の温度でさらに２時間撹
拌した。この間の反応系の圧力は、８Kg／cm2であ
つた。
冷却した後、反応生成物を取出しガスクロマト
グラフイーで分析したところ、Ｎ，Ｎ−ジメチル
エチレンジアミンの収率はエチレンイミンに対し
て87mol％であつた。
反応生成物を蒸留して沸点107℃の留分を得た。
当該留分は、ガスクロマトグラフイー、質量分析
計、NMRによりＮ，Ｎ−ジメチルエチレンジア
ミンであることが確認された。
実施例 ２
実施例１において、ジメチルアミンの代りにジ
エチルアミンを用い、反応温度を120℃とする他
は同様の手順に従つて反応させた。Ｎ，Ｎ−ジエ
チルエチレンジアミンの収率は、70mol％であつ
た。
実施例 ３
実施例１において、エチレンイミンの代りにプ
ロピレンイミンを用いる他は同様の手順に従つて
反応させた。Ｎ，Ｎ−ジメチルプロピレンジアミ
ンの収率は、83mol％であつた。
実施例 ４〜７
実施例１において、第１表に示す反応条件とす
る他は同様の手順に従つて反応させた。Ｎ，Ｎ−
ジメチルエチレンジアミンの収率は、第１表に示
したとおりであつた。
比較例 １
温度計、還流冷却器、撹拌機および滴下装置を
備えた容量500c.c.の四口フラスコに水90ｇ、ジメ
チルアミン135ｇを仕込んだ。60〜70℃に昇温し
維持し、撹拌下、エチレンイミン43ｇを１時間か
けて添加し、添加終了後60〜70℃の温度でさらに
２時間撹拌した。Ｎ，Ｎ−ジメチルエチレンジア
ミンの収率は、40mol％であつた。
比較例 ２
実施例１において、オートクレーブを開放系と
し、反応温度を還流温度とする他は同様の手順に
従つて反応させた。収率は、第１表に示したとお
りであつた。[Formula] (In the formula, R 2 represents an alkyl group having 1 to 3 carbon atoms, and R 2 and R 3 are the same or different.) 2 to 5 mol of the latter is added to 1 mol of the former. It is characterized in that it is used in molar ratio amounts and is reacted in a closed system in the presence of an acid catalyst in a monohydric aliphatic lower alcohol solvent at a temperature in the range of 90 to 150°C. The reaction is then carried out using an acid catalyst, a dialkylamine, and a monovalent aliphatic lower alcohol.
The asymmetric reaction can be achieved by continuously or intermittently adding an alkyleneimine to a mixture kept at a temperature in the range of ~150°C, and maintaining the reaction system at that temperature even after the addition is complete. The yield of alkyl alkylene diamine can be dramatically increased. The alkylene imine in the present invention is represented by the above general formula, and includes, for example, ethyleneimine and propylene imine, which can be used singly or as a mixture of two. The dialkylamine is represented by the above general formula, and includes, for example, dimethylamine, diethylamine, dipropylamine, etc., and can be used alone or as a mixture of two or more. As an acid catalyst,
Various acids can be mentioned, such as hydrochloric acid, sulfuric acid, etc. Hydrochloric acid is particularly preferred and can be used in an amount of 1 to 5 mol %, based on the alkylene imine. The solvent in the present invention is a monovalent aliphatic lower alcohol, such as methyl alcohol, ethyl alcohol, propyl alcohol, isopropyl alcohol, butyl alcohol, etc. having 1 to 1 carbon atoms.
Among them, methyl alcohol, ethyl alcohol and the like are particularly preferred. The amount of solvent to be used is not particularly limited as long as it functions as a reaction solvent, and may be, for example, 20 to 50 wt% based on the total amount of the reactants. The amount of solvent used is essential, and if it is not used, the yield of the target product will decrease. The reaction between alkyleneimine and dialkylamine is carried out in a closed system, i.e. under spontaneous pressure or external pressure, at a reaction temperature of 90 to 150°C, preferably 100°C.
This can be done by keeping the temperature within the range of ~130°C. At this time, if the reaction temperature is set to a low temperature below 90°C, the reaction rate will be slow, and conversely, if the reaction temperature is set to a low temperature exceeding 150°C, it will not contribute to improving the yield and will only unnecessarily increase the system pressure, making it technically meaningless. It is something without. Suitably, the ratio of both reactants in the total amount used is 2 to 5 moles of dialkylamine to 1 mole of alkyleneimine. When the ratio is less than 2, reaction by-products increase and the yield of the target product decreases, while when it exceeds 5, the amount of dialkylamine recovered increases, which is not industrially advantageous. and the reactant,
The desired product can be achieved by either adding the acid catalyst and solvent into a reactor all at once and reacting, or adding the reactants continuously or intermittently to the solvent containing the acid catalyst and keeping the temperature in the range of 90 to 150°C. However, the alkyleneimine can be added continuously or intermittently to a mixture consisting of an acid catalyst, a dialkylamine, and a solvent maintained at a temperature in the range of 90 to 150°C, and the addition can be terminated if necessary. The yield of the target product can be dramatically increased by maintaining the reaction system at the temperature after the reaction and allowing the reaction to proceed. The asymmetric alkyl alkylene diamine can be easily separated from the reaction product following a fractional distillation procedure. According to the production method of the present invention, an asymmetric alkylalkylene diamine can be produced in high yield through a simple production process. Hereinafter, the present invention will be explained in more detail with reference to Examples. Example 1 In an autoclave with a capacity of 500 c.c., 90 g of methyl alcohol, 135 g (3 moles) of dimethylamine, and
7.3g of 15wt% hydrochloric acid/methyl alcohol solution was charged and the container was sealed. Raise the temperature to 110℃ and maintain it while stirring.
43 g (1 mol) of ethyleneimine was added over a period of 1 hour, and after the addition was complete, the mixture was stirred for an additional 2 hours at a temperature of 110°C. The pressure in the reaction system during this time was 8 Kg/cm 2 . After cooling, the reaction product was taken out and analyzed by gas chromatography, and the yield of N,N-dimethylethylenediamine was 87 mol% based on ethyleneimine. The reaction product was distilled to obtain a fraction with a boiling point of 107°C.
The fraction was confirmed to be N,N-dimethylethylenediamine by gas chromatography, mass spectrometry, and NMR. Example 2 A reaction was carried out in accordance with the same procedure as in Example 1 except that diethylamine was used instead of dimethylamine and the reaction temperature was changed to 120°C. The yield of N,N-diethylethylenediamine was 70 mol%. Example 3 The reaction was carried out in accordance with the same procedure as in Example 1, except that propylene imine was used instead of ethylene imine. The yield of N,N-dimethylpropylene diamine was 83 mol%. Examples 4 to 7 The reaction was carried out in the same manner as in Example 1, except that the reaction conditions shown in Table 1 were used. N, N-
The yield of dimethylethylenediamine was as shown in Table 1. Comparative Example 1 90 g of water and 135 g of dimethylamine were charged into a 500 c.c. four-necked flask equipped with a thermometer, reflux condenser, stirrer and dropping device. The temperature was raised to and maintained at 60 to 70°C, and 43 g of ethyleneimine was added over 1 hour while stirring, and after the addition was completed, stirring was continued at a temperature of 60 to 70°C for an additional 2 hours. The yield of N,N-dimethylethylenediamine was 40 mol%. Comparative Example 2 The reaction was carried out in the same manner as in Example 1, except that the autoclave was an open system and the reaction temperature was set to reflux temperature. The yield was as shown in Table 1.
【表】【table】
【表】
＊ 反応体、触媒および溶媒を一度にオートクレーブ
に仕込んだ。
実施例 ８
実施例１において、アミン／イミンのモル比を
５とする他は同様の手順に従つて反応させた。
Ｎ，Ｎ−ジメチルエチレンジアミンの収率は、
92mol％であつた。
実施例 ９
実施例１において、ジメチルアミンの代りにジ
プロピルアミンを用いる他は同様の手順に従つて
反応させた。Ｎ，Ｎ−ジプロピルエチレンジアミ
ンの収率は、67mol％であつた。[Table] *Reactants, catalyst and solvent were charged into the autoclave at once.
Example 8 The reaction was carried out in the same manner as in Example 1, except that the molar ratio of amine/imine was changed to 5.
The yield of N,N-dimethylethylenediamine is
It was 92 mol%. Example 9 The reaction was carried out in accordance with the same procedure as in Example 1 except that dipropylamine was used instead of dimethylamine. The yield of N,N-dipropylethylenediamine was 67 mol%.
Claims (1)
す。） で示されるアルキレンイミンと一般式 【式】 （式中、R2およびR3は炭素数１〜３個のアルキ
ル基を表わし、R2とR3は同一または異なる。） で示されるジアルキルアミンを、前者１モルに対
して後者２〜５モルの比率の量で使用し、密閉系
で、酸触媒の存在下に１価の脂肪族低級アルコー
ル溶媒中90〜150℃の範囲の温度で反応させるこ
とを特徴とする非対称アルキルアルキレンジアミ
ンの製造方法。 ２ 反応は酸触媒ジアルキルアミンおよび１価の
脂肪族低級アルコールから成り90〜150℃の範囲
の温度に保たれた混合物にアルキレンイミンを連
続的または間歇的に添加して、必要に応じて当該
添加終了後も反応系を当該温度に維持して、行な
わせる特許請求の範囲第１項記載の製造方法。 ３ 反応は酸触媒を含み90〜150℃の範囲の温度
に保たれた１価の脂肪族低級アルコールにジアル
キルアミンおよびアルキレンイミンを別々にまた
は一緒に、連続的または間歇的に添加して、必要
に応じて当該添加終了後も反応系を当該温度に維
持して、行なわせる特許請求の範囲第１項記載の
製造方法。[Claims] 1 An alkyleneimine represented by the general formula [formula] (wherein R 1 represents a hydrogen atom or a methyl group) and a general formula [formula] (wherein R 2 and R 3 are carbon A dialkylamine represented by 1 to 3 alkyl groups, and R 2 and R 3 are the same or different is used in a ratio of 2 to 5 mol of the latter to 1 mol of the former, and a closed system A method for producing an asymmetric alkyl alkylene diamine, which is characterized in that the reaction is carried out in the presence of an acid catalyst in a monovalent aliphatic lower alcohol solvent at a temperature in the range of 90 to 150°C. 2 The reaction consists of an acid-catalyzed dialkylamine and a monohydric aliphatic lower alcohol, and the alkyleneimine is added continuously or intermittently to a mixture kept at a temperature in the range of 90 to 150°C, and the addition is carried out as necessary. The manufacturing method according to claim 1, wherein the reaction system is maintained at the same temperature even after the completion of the reaction. 3. The reaction is carried out by adding dialkylamine and alkyleneimine separately or together, continuously or intermittently, to a monohydric aliphatic lower alcohol containing an acid catalyst and maintained at a temperature in the range of 90 to 150 °C. The manufacturing method according to claim 1, wherein the reaction system is maintained at the temperature after the completion of the addition according to the above.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56142332A JPS5846042A (en) | 1981-09-11 | 1981-09-11 | Preparation of asymmetric alkylalkylenediamine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56142332A JPS5846042A (en) | 1981-09-11 | 1981-09-11 | Preparation of asymmetric alkylalkylenediamine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5846042A JPS5846042A (en) | 1983-03-17 |
| JPS647982B2 true JPS647982B2 (en) | 1989-02-10 |
Family
ID=15312885
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56142332A Granted JPS5846042A (en) | 1981-09-11 | 1981-09-11 | Preparation of asymmetric alkylalkylenediamine |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5846042A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5235107A (en) * | 1988-11-22 | 1993-08-10 | Nippon Shokubai Kagaku Kogyo Co., Ltd. | Method of producing ethylenediamines |
| US5262570A (en) * | 1988-11-22 | 1993-11-16 | Nippon Shokubai Kagaku Kogyo Co., Ltd. | Method of producing ethylenediamines |
| DE3934191A1 (en) * | 1989-10-13 | 1991-04-18 | Basf Ag | METHOD FOR PRODUCING N-ALKYL AND N, N-DIALKYL DIAMINOETHANES |
-
1981
- 1981-09-11 JP JP56142332A patent/JPS5846042A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5846042A (en) | 1983-03-17 |
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