JPS62129257A - Production of benzylamine - Google Patents
Production of benzylamineInfo
- Publication number
- JPS62129257A JPS62129257A JP26941285A JP26941285A JPS62129257A JP S62129257 A JPS62129257 A JP S62129257A JP 26941285 A JP26941285 A JP 26941285A JP 26941285 A JP26941285 A JP 26941285A JP S62129257 A JPS62129257 A JP S62129257A
- Authority
- JP
- Japan
- Prior art keywords
- benzonitrile
- catalyst
- ammonia
- benzylamine
- reaction
- 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
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、ベンゾニトリルを接触水素添加し、収率よ（
ベンジルアミンを製造する方法に関する。[Detailed Description of the Invention] <Industrial Application Field> The present invention involves the catalytic hydrogenation of benzonitrile to improve the yield (
The present invention relates to a method for producing benzylamine.
ベンジルアミンは、工業原料として有用な化合物であり
、医薬・染料・界面活性剤・化学薬品等多方面にわたっ
て使用されている。Benzylamine is a compound useful as an industrial raw material, and is used in a wide range of fields such as medicines, dyes, surfactants, and chemicals.
〈従来技術及び問題点〉
従来、ベンゾニトリルを接触水素添加してベンジルアミ
ンを合成する方法は公知である。<Prior Art and Problems> Conventionally, a method for synthesizing benzylamine by catalytic hydrogenation of benzonitrile is known.
例えば、特開昭５１−１０１９３０ではベンゾニトリル
と水素を連続的に触媒床上で交流接触させ、ベンジルア
ミンを得ているが、この場合同時に副生物としてジベン
ジルアミンが生成している。For example, in JP-A-51-101930, benzonitrile and hydrogen are brought into continuous AC contact on a catalyst bed to obtain benzylamine, but in this case dibenzylamine is also produced as a by-product.
又、米国特許４２５４０５９ ではルテニウム−ホス
フィン錯体触媒を用いてベンゾニトリルを水素添加して
いるが、この場合ルテニウムは貴金属の一種であり、同
触媒はかなり高価なものになり、経済的とは決して言え
ない。Furthermore, in U.S. Pat. No. 4,254,059, benzonitrile is hydrogenated using a ruthenium-phosphine complex catalyst, but in this case, ruthenium is a type of noble metal, and the catalyst is quite expensive, making it far from economical. do not have.
〈問題点を解決するための手段〉
そこで、本発明者は鋭意検討を重ねた結果、発明を完成
するに到った。即ち、本発明はアンモニアの共存下で、
ベンゾニトリルを接触水素添加せしめることを特徴とす
るベンジルアミンの製造法である。<Means for Solving the Problems> Therefore, the inventors of the present invention have made extensive studies and have completed the invention. That is, in the present invention, in the coexistence of ammonia,
This is a method for producing benzylamine, which is characterized by catalytic hydrogenation of benzonitrile.
ところで、該反応機構は第１図の通り、出発原料が広範
囲の触媒によって接触的に還元され、各中間体を経て目
的物あるいは副生物に到るものと推察される。By the way, the reaction mechanism is as shown in FIG. 1, and it is presumed that the starting material is catalytically reduced by a wide range of catalysts, and the target product or by-product is reached through various intermediates.
第１図
以下に本発明をより詳しく説明する。本発明において原
料に用いるベンゾニトリルは一般的に工業原料として容
易に入手可能であり、特別の精製等を要しない。The present invention will be explained in more detail below in FIG. Benzonitrile used as a raw material in the present invention is generally easily available as an industrial raw material and does not require any special purification.
アンモニアの添加量はベンゾニトリルに対して０２〜２
．０モル倍、好ましくは０，５〜１．５モル倍の範囲で
使用される。同数１直より少な（・とジベンジルアミン
の副生率が増加し、それより多いと反応後のアンモニア
回収工程でのアンモニアロスが増加するので不都合であ
る。The amount of ammonia added is 02 to 2 to benzonitrile.
．． It is used in an amount of 0 mol, preferably 0.5 to 1.5 mol. If the number is less than one shift, the by-product rate of dibenzylamine will increase, and if it is more than that, the ammonia loss in the ammonia recovery step after the reaction will increase, which is disadvantageous.
触媒は、一般的な水素添加用触媒のうち、安価なラネー
ニッケルあるいはラネーコバルトが好適に使用される。Among common hydrogenation catalysts, Raney nickel or Raney cobalt is preferably used as the catalyst.
その使用量はベンゾニトリルに対して２〜１２ｗｔ％、
好ましくは５〜ｌＱｗｔ％の範囲である。The amount used is 2 to 12 wt% based on benzonitrile.
Preferably it is in the range of 5 to 1Qwt%.
又、通常、反応溶媒として非還元性の極性溶媒、例えば
、水、メタノール、エタノール等が利用され、その使用
量はベンジエ） ＩＪルに対して、１．０〜５．０重量
倍の範囲から選ばれる。In addition, a non-reducing polar solvent such as water, methanol, ethanol, etc. is usually used as a reaction solvent, and the amount used is from 1.0 to 5.0 times the weight of benzene. To be elected.
本発明における反応温度は５０〜１５０°Ｃの範囲で実
施可能であるが、反応速度等を考慮すれば８０〜１２０
℃の範囲が望ましい。又、反応圧力（水素分圧）は５０
〜１５０ｋｇＺｃ４Ｇの範囲なら任意であるが、反応装
置の設計上の問題点及び該反応性ルネＯ〜１２０ｋｇ／
ｃＡＧの範囲が好ましい。The reaction temperature in the present invention can be carried out in the range of 50 to 150°C, but considering the reaction rate etc.
A range of ℃ is desirable. Also, the reaction pressure (hydrogen partial pressure) is 50
-150 kgZc4G is arbitrary, but there are problems in the design of the reactor and the reactive Rene O-120 kg/
A range of cAG is preferred.
このようにして得られた反応粗液は通電、触媒を戸別し
た後、アンモニア−メタノールを常圧で留去させる。留
去したアンモニアはスクラバーにて冷却されたメタノー
ルに吸収され、反応系ヘリサイクルされる。一方、脱溶
媒後の粗ベンジルアミンは、一般に用いられる蒸溜設備
によって容易に精製される。The reaction crude liquid thus obtained is energized, the catalyst is removed, and then the ammonia-methanol is distilled off at normal pressure. The distilled ammonia is absorbed by cooled methanol in a scrubber and recycled to the reaction system. On the other hand, the crude benzylamine after desolvation is easily purified using commonly used distillation equipment.
〈発明の効果）
本発明の方法によれば、前記した従来技術の欠点を排除
し、例えばラネーニッケルあるいはラネーコバルトの如
き安価な触媒が使用でき、ジベンジルアミンの副生を抑
制する等、しかも収率よく、容易に目的物を得ることが
できる。<Effects of the Invention> According to the method of the present invention, the drawbacks of the prior art described above can be eliminated, an inexpensive catalyst such as Raney nickel or Raney cobalt can be used, and the by-product of dibenzylamine can be suppressed. You can get what you want quickly and easily.
〈実施例〉
次に、実施例及び比較例を挙げて本発明を具体的に説明
する。<Example> Next, the present invention will be specifically explained by giving examples and comparative examples.
実施例１゜
１βの電磁攪拌式オートクレーブを使用して、ベンゾニ
トリル１１０ｇを、アンモニア性メタノール（アンモエ
フ６度１２．９ ｗｔ％）２８７ｇに溶解しくアンモニ
ア／出発原料＝２．０６モル倍）、ラネーニッケル触媒
１ｏｇを添加した後、反応温度１００’Ｃに加熱し、水
素圧力１００ ｋｌｉ’／ ｃｒｆｒ Ｇで反応させた
。Example 1 Using a 1β electromagnetic stirring autoclave, 110 g of benzonitrile was dissolved in 287 g of ammoniacal methanol (Ammoev 6 degrees 12.9 wt%) (ammonia/starting material = 2.06 mole times), Raney nickel. After adding 1 og of catalyst, it was heated to a reaction temperature of 100'C and reacted at a hydrogen pressure of 100 kli'/crfr G.
結果、２時間後の反応粗液のガスクロマトゲ注１）
ラフ分析 によると、ベンゾニトリＩ・は完全に消失
し、生成物としてはベンジルアミン９２．９％、ジベン
ジルアミン１．７８％、その他５．３２％であった。As a result, gas chromatography Note 1) rough analysis of the crude reaction solution after 2 hours revealed that benzonitrile I had completely disappeared, and the products were 92.9% benzylamine, 1.78% dibenzylamine, and 5 others. It was .32%.
注１） 数値はメタノールを除いた百分率を表わす。以
下同じ。Note 1) Values represent percentages excluding methanol. same as below.
次いで、２０段の多孔板塔を使用して、触媒を戸別した
反応粗液３５０ｇを常圧で脱メタノール（脱アンモニア
）した後、得られた缶液を、１００ Ｔｏｒｒの減圧下
、還流比５で清潔し、ベンジルアミン１０５ｇを得た（
主留分１０８〜１１４℃／ １００ Ｔｏｒｒ） （純
度９９．２％）。Next, using a 20-stage perforated plate column, 350 g of the reaction crude liquid from which the catalyst had been removed was demethanolated (deammoniated) at normal pressure, and the resulting bottom liquid was heated to a reflux ratio of 5 under a reduced pressure of 100 Torr. to obtain 105 g of benzylamine (
Main fraction 108-114°C/100 Torr) (purity 99.2%).
全収率は９１．９％であった。The overall yield was 91.9%.
比較例
実施例１と同じ条件でアンモニアを添加せずに反応を行
なった。Comparative Example A reaction was carried out under the same conditions as in Example 1 without adding ammonia.
結果、２時間後の反応粗液のガスクロマトグラフ分非身
ンジルアミン６１．１％、ジベンジルアミン２０．４％
であった（ベンゾニトリル転化率９９．２％）。As a result, gas chromatograph analysis of the crude reaction solution after 2 hours showed 61.1% dibenzylamine and 20.4% dibenzylamine.
(Benzonitrile conversion rate 99.2%).
実施例２゜
触媒濃度（対出発原料）を５．０Ｗ％及びアンモニア／
出発原料を第１表に示した数値に変更し、実施例１と同
じ条件で反応を行なった。Example 2゜Catalyst concentration (based on starting material) was 5.0W% and ammonia/
The starting materials were changed to the values shown in Table 1, and the reaction was carried out under the same conditions as in Example 1.
結果、２時間後の反応粗液のガスクロマトグラフ分析は
第１表の通り。As a result, gas chromatography analysis of the reaction crude liquid after 2 hours is as shown in Table 1.
第１表
実施例３゜
触媒をラネーコパル）１０ｇに変更し、実施例１と同じ
条件で反応を行なった。Table 1 Example 3 The reaction was carried out under the same conditions as in Example 1 except that the catalyst was changed to 10 g of Raney Copal.
結果、２時間後の反応粗液のガスクロマトグラフ分析で
はベンジルアミン９２．７％、ジベンジルアミン２．２
６％であった（ベンゾニトリル転化率１００％）。As a result, gas chromatographic analysis of the reaction crude liquid after 2 hours revealed that benzylamine was 92.7% and dibenzylamine was 2.2%.
6% (benzonitrile conversion rate 100%).
特詐出願人 ダイセル化学工業株式会社special fraud applicant Daicel Chemical Industries, Ltd.
Claims (1)
せしめることを特徴とするベンジルアミンの製造法A method for producing benzylamine, characterized by catalytic hydrogenation of benzonitrile in the coexistence of ammonia.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60269412A JP2811065B2 (en) | 1985-12-02 | 1985-12-02 | Method for producing benzylamine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60269412A JP2811065B2 (en) | 1985-12-02 | 1985-12-02 | Method for producing benzylamine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62129257A true JPS62129257A (en) | 1987-06-11 |
| JP2811065B2 JP2811065B2 (en) | 1998-10-15 |
Family
ID=17472053
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60269412A Expired - Lifetime JP2811065B2 (en) | 1985-12-02 | 1985-12-02 | Method for producing benzylamine |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2811065B2 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1036785A1 (en) * | 1999-03-02 | 2000-09-20 | Bayer Aktiengesellschaft | Process for the preparation of bis(trifluoromethyl)benzylamines |
| JP2005534690A (en) * | 2002-08-01 | 2005-11-17 | ビーエーエスエフ アクチェンゲゼルシャフト | Process for producing aminoalkoxybenzylamine and aminoalkoxybenzonitrile as intermediates |
| US7179944B2 (en) | 2003-03-11 | 2007-02-20 | Wyeth | Process for preparation of phenethylamine derivatives |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2022517681A (en) * | 2019-01-25 | 2022-03-09 | エスアールエフ リミテッド | Methods for Preparing Halogenated Benzylamine and its Intermediates |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51101930A (en) * | 1975-01-16 | 1976-09-08 | Miles Lab | |
| JPS55104235A (en) * | 1979-02-01 | 1980-08-09 | Suntech | Hydrogenation of aromatic nitrile to primary amine |
| JPS5923857A (en) * | 1982-07-28 | 1984-02-07 | Kawasaki Steel Corp | Production of galvanized steel plate subjected to alloying treatment on only one side |
-
1985
- 1985-12-02 JP JP60269412A patent/JP2811065B2/en not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51101930A (en) * | 1975-01-16 | 1976-09-08 | Miles Lab | |
| JPS55104235A (en) * | 1979-02-01 | 1980-08-09 | Suntech | Hydrogenation of aromatic nitrile to primary amine |
| JPS5923857A (en) * | 1982-07-28 | 1984-02-07 | Kawasaki Steel Corp | Production of galvanized steel plate subjected to alloying treatment on only one side |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1036785A1 (en) * | 1999-03-02 | 2000-09-20 | Bayer Aktiengesellschaft | Process for the preparation of bis(trifluoromethyl)benzylamines |
| US6137011A (en) * | 1999-03-02 | 2000-10-24 | Bayer Aktiengesellschaft | Process for the preparation of bistrifluoromethylbenzylamines |
| JP2005534690A (en) * | 2002-08-01 | 2005-11-17 | ビーエーエスエフ アクチェンゲゼルシャフト | Process for producing aminoalkoxybenzylamine and aminoalkoxybenzonitrile as intermediates |
| US7179944B2 (en) | 2003-03-11 | 2007-02-20 | Wyeth | Process for preparation of phenethylamine derivatives |
| US7563931B2 (en) | 2003-03-11 | 2009-07-21 | Wyeth | Process for preparation of phenethylamine derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2811065B2 (en) | 1998-10-15 |
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