JPS647981B2 - - Google Patents
Info
- Publication number
- JPS647981B2 JPS647981B2 JP56142331A JP14233181A JPS647981B2 JP S647981 B2 JPS647981 B2 JP S647981B2 JP 56142331 A JP56142331 A JP 56142331A JP 14233181 A JP14233181 A JP 14233181A JP S647981 B2 JPS647981 B2 JP S647981B2
- Authority
- JP
- Japan
- Prior art keywords
- temperature
- reaction
- carried out
- acid catalyst
- range
- 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
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 239000003377 acid catalyst Substances 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- -1 alkylene imine Chemical class 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
- 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
- 150000001298 alcohols Chemical class 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
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 5
- 150000004985 diamines Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- KFIGICHILYTCJF-UHFFFAOYSA-N n'-methylethane-1,2-diamine Chemical compound CNCCN KFIGICHILYTCJF-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000000034 method Methods 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
- 238000004817 gas chromatography Methods 0.000 description 2
- SCZVXVGZMZRGRU-UHFFFAOYSA-N n'-ethylethane-1,2-diamine Chemical compound CCNCCN SCZVXVGZMZRGRU-UHFFFAOYSA-N 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
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 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
- 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
- 238000004508 fractional distillation Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 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モノアルキルア
ミンとからＮ−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。
Ｎ−アルキルアルキレンジアミンの製造方法と
して、例えば特開昭55−167258号明細書からエチ
レンジアミンとハロゲン化エチルを特定条件下で
反応させＮ−エチルエチレンジアミンを製造する
方法が知られている。しかし、アルキレンイミン
とモノアルキルアミンとから、商業的にＮ−アル
キルアルキレンジアミンを製造する方法は、まだ
知られていない。
本発明者らは、このような現状に鑑み、アルキ
レンイミンおよびモノアルキルアミンを出発原料
とするＮ−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で反応させることに
よりＮ−アルキルアルキレンジアミンを効率良く
製造することができ、そして密閉系で特定の反応
条件下で反応させることによりＮ−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Ｎ−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 N-alkyl alkylene diamine from an alkylene imine and a monoalkyl amine. As a method for producing N-alkylalkylenediamine, a method for producing N-ethylethylenediamine by reacting ethylenediamine and ethyl halide under specific conditions is known, for example, from JP-A-55-167258. However, a method for commercially producing N-alkyl alkylene diamine from alkylene imine and monoalkyl amine is not yet known. In view of the current situation, the present inventors have conducted intensive research on a method for producing N-alkylalkyl diamine using alkylene imine and monoalkyl amine as starting materials. By reacting in a closed system, N-alkylalkylene diamine can be efficiently produced, and by reacting in a closed system under specific reaction conditions, the yield of N-alkyl alkylene diamine can be dramatically increased. With this discovery, the present invention has been completed. The method for producing N-alkylalkylene 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
R2NH2
（式中、R2は炭素数１〜３個のアルキル基を表
わす。）
で示されるモノアルキルアミンを、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、モノアルキルア
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Ｎ−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、上記一般
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。モノアルキ
ルアミンは、上記一般式で示されるもので、例え
ばモノメチルアミン、モノエチルアミン、モノプ
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モノ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モルに対してモノアルキルアミン２〜
５モルの比率とするのが適当である。当該比率が
２末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を越えるとモノアルキルアミン回
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、モノ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。
Ｎ−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
Ｎ−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、モノメチルアミン155ｇ（５モル）およ
び15wt％塩酸・メチルアルコール溶液73ｇを仕
込み、密閉した。120℃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120℃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−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
93mol％であつた。
反応生成物を蒸留して沸点116℃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−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、モノメチルアミンの代りに
モノエチ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−エチルエチレンジアミンの収
率は80mol％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−メチルプロピレンジアミンの収
率は68mol％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−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、モノ
メチルアミン155ｇ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−メチルエチレンジアミン
の収率は30mol％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 1 represents hydrogen or a methyl group.) Alkyleneimine represented by the general formula R 2 NH 2 (In the formula, R 2 represents an alkyl group having 1 to 3 carbon atoms.) A monoalkylamine represented by is used in a ratio of 2 to 5 moles of the latter to 1 mole of the former, and the mixture is heated at 90 to 150°C in a monohydric lower aliphatic alcohol solvent in the presence of an acid catalyst in a closed system. It is characterized in that the reaction is carried out at a temperature in the range of . The reaction is carried out using an acid catalyst, a monoalkylamine, and a monovalent aliphatic lower alcohol.
Adding the alkyleneimine continuously or intermittently to the mixture maintained at a temperature in the range of 90-150°C,
The yield of N-alkyl alkylene diamine can be dramatically increased by maintaining the reaction system at the temperature after the completion of the addition, if necessary. 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 monoalkylamine is represented by the above general formula, and includes, for example, monomethylamine, monoethylamine, monopropylamine, etc., and can be used singly or as a mixture of two or more. As the acid catalyst, various acids such as hydrochloric acid and sulfuric acid can be mentioned, and 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 use of a solvent is essential; if it is not used, the yield of the target product will decrease. The reaction between the alkyleneimine and the monoalkylamine is carried out in a closed system, i.e. under spontaneous pressure or external pressure, at a reaction temperature of 90-150°C, preferably
It can be carried out by keeping the temperature in the range of 100 to 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. The ratio of both in the total amount of reactants used is 2 to 1 mole of monoalkylamine to 1 mole of alkyleneimine.
A ratio of 5 moles is suitable. 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 monoalkylamine recovered increases, which is not industrially advantageous. Then, the reactant, acid catalyst, and solvent can be charged into a reactor all at once and reacted, or the reactant can be added continuously or intermittently to a solvent containing an acid catalyst and kept at a temperature in the range of 90 to 150 °C. The desired product can be obtained by adding an alkyleneimine continuously or intermittently to a mixture consisting of an acid catalyst, a monoalkylamine, and a solvent kept at a temperature in the range of 90 to 150°C. Accordingly, the yield of the target product can be dramatically increased by maintaining the reaction system at the temperature and allowing the reaction to occur even after the completion of the addition. The N-alkylalkylene diamine can be easily separated from the reaction product following a fractional distillation procedure. According to the production method of the present invention, N-alkylalkylene diamine can be produced in high yield through simple production steps. Hereinafter, the present invention will be explained in more detail with reference to Examples. Example 1 An autoclave with a capacity of 500 c.c. was charged with 90 g of methyl alcohol, 155 g (5 moles) of monomethylamine, and 73 g of a 15 wt % hydrochloric acid/methyl alcohol solution, and the autoclave was sealed. Raise and maintain the temperature at 120℃, under stirring,
43 g (1 mol) of ethyleneimine was added over 1 hour, and after the addition was complete, the mixture was stirred for an additional 2 hours at a temperature of 120°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 it was found that the yield of N-methylethylenediamine was the same as that of ethyleneimine.
It was 93 mol%. The reaction product was distilled to obtain a fraction with a boiling point of 116°C.
The fraction was confirmed to be N-methylethylenediamine by gas chromatography, mass spectrometry, and NMR. Example 2 The reaction was carried out in the same manner as in Example 1 except that monoethylamine was used instead of monomethylamine. The yield of N-ethylethylenediamine was 80 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-methylpropylene diamine was 68 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. The yield of N-methylethylenediamine was as shown in Table 1. Comparative Example 1 90 g of water and 155 g of monomethylamine 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 2 hours. The yield of N-methylethylenediamine was 30 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。
第１表から明らかなように、本発明に従えば、
Ｎ−アルキルアルキレンジアミン（目的物）を高
収率で製造できる。[Table] *Reactants, catalyst and solvent were charged into the autoclave at once.
As is clear from Table 1, according to the present invention,
N-alkyl alkylene diamine (target product) can be produced in high yield.
Claims (1)
す。） で示されるアルキレンイミンと一般式 R2NH2 （式中、R2は炭素数１〜３個ののアルキル基を
表わす。） で示されるモノアルキルアミンを、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Ｎ−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、モノ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モノア
ルキルアミンおよびアルキレンイミンを別々にま
たは一諸に、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 an alkyleneimine represented by the general formula R 2 NH 2 (wherein R 2 has 1 carbon number) ~3 alkyl groups) is used in a ratio of 2 to 5 moles of the latter to 1 mole of the former, and monovalent monoalkylamines are used in a closed system in the presence of an acid catalyst. 1. A method for producing N-alkyl alkylene diamine, which comprises reacting in a lower aliphatic alcohol solvent at a temperature in the range of 90 to 150°C. 2 The reaction is carried out using an acid catalyst, a monoalkylamine and 1
The alkylene imine is added continuously or intermittently to a mixture consisting of aliphatic lower alcohols of 100 to 150°C and kept at a temperature in the range of 90 to 150°C, and if necessary, the reaction system is maintained at the temperature even after the addition is completed. maintain,
The manufacturing method according to claim 1, which is carried out. 3. The reaction is carried out by continuously or intermittently adding a monoalkylamine and an alkylene imine to a monohydric aliphatic lower alcohol containing an acid catalyst and maintained at a temperature in the range of 90 to 150°C. 2. The manufacturing method according to claim 1, wherein the reaction system is maintained at the temperature as required even after the addition is completed.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56142331A JPS5846041A (en) | 1981-09-11 | 1981-09-11 | Preparation of n-alkylalkylenediamine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56142331A JPS5846041A (en) | 1981-09-11 | 1981-09-11 | Preparation of n-alkylalkylenediamine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5846041A JPS5846041A (en) | 1983-03-17 |
| JPS647981B2 true JPS647981B2 (en) | 1989-02-10 |
Family
ID=15312859
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56142331A Granted JPS5846041A (en) | 1981-09-11 | 1981-09-11 | Preparation of n-alkylalkylenediamine |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5846041A (en) |
Families Citing this family (2)
| 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 |
-
1981
- 1981-09-11 JP JP56142331A patent/JPS5846041A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5846041A (en) | 1983-03-17 |
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