JPS62120329A - Production of bromobenzene - Google Patents
Production of bromobenzeneInfo
- Publication number
- JPS62120329A JPS62120329A JP60259724A JP25972485A JPS62120329A JP S62120329 A JPS62120329 A JP S62120329A JP 60259724 A JP60259724 A JP 60259724A JP 25972485 A JP25972485 A JP 25972485A JP S62120329 A JPS62120329 A JP S62120329A
- Authority
- JP
- Japan
- Prior art keywords
- benzene
- polybromobenzene
- aluminum chloride
- bromobenzene
- dibromobenzene
- 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.)
- Pending
Links
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
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、各種の医薬、農業、染料などの中間体として
有用なブロモベンゼンの製造法に関する。DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to a method for producing bromobenzene, which is useful as an intermediate for various medicines, agriculture, dyes, and the like.
（従来の技術）
ブロモベンゼンをベンゼンと臭素あるいは臭化物から製
造する方法は知られている。（カーク・オスマー曙、エ
ンサイクロペディアオブケミカルテクノロジー（ジョン
ウイリーアンドサンズ）（第３版）、４巻、２３２真他
）。(Prior Art) A method for producing bromobenzene from benzene and bromine or bromide is known. (Kirk Osmer Akebono, Encyclopedia of Chemical Technology (John Willey and Sons) (3rd edition), vol. 4, 232 true et al.).
しかしながら、ベンゼンとポリブロモベンゼンからブロ
モベンゼンを製造する方法については知られていない。However, no method is known for producing bromobenzene from benzene and polybromobenzene.
（発明が解決しようとする問題点）
ブロモベンゼンをベンゼンと臭素等から製造する際に、
ジブロモベンゼン、トリブロモベンゼンが相当量副生じ
、ベンゼン、臭素等の損失をもたらす。この副生するポ
リブロモベンゼンをブロモベンゼンに転換する方法は知
られていない。(Problems to be solved by the invention) When producing bromobenzene from benzene and bromine, etc.
A considerable amount of dibromobenzene and tribromobenzene are produced as by-products, resulting in loss of benzene, bromine, etc. There is no known method for converting this by-produced polybromobenzene into bromobenzene.
（問題点を解決するための手段）
本発明者らは、ジブロモベンゼンやトリブロモベンゼン
をブロモベンゼンに転換する方法について鋭意検討を重
ねた結果、ベンゼンとポリブロモベンゼンを液相におい
て塩化アルミニウムを触媒に用いて反応させる事によっ
て選択性良くブロモベンゼンが得られる事を見出し、本
発明を完成するに至った。(Means for Solving the Problems) As a result of extensive studies on a method for converting dibromobenzene and tribromobenzene into bromobenzene, the present inventors discovered that aluminum chloride is catalyzed in benzene and polybromobenzene in a liquid phase. The present inventors discovered that bromobenzene can be obtained with good selectivity by reacting the compound using the following methods, and have completed the present invention.
すなわち、本発明は、ベンゼンとポリブロモベンゼンを
液相で反応させてブロモベンゼンを製造する際に、塩化
アルミニウムを触媒として用いる事を特徴とするブロモ
ベンゼンの製造法を提供するものである。That is, the present invention provides a method for producing bromobenzene, which is characterized in that aluminum chloride is used as a catalyst when producing bromobenzene by reacting benzene and polybromobenzene in a liquid phase.
本発明に用いられる塩化アルミニウムの量は特に制限は
ないが、あまり少なすぎると、反応速度が極めて遅くな
り、又、あまり多すぎると経済的に不利になるため、好
ましくは、ベンゼンとポリブロモベンゼンの和に対して
０．０５〜１０重量％、さらに好ましくは、０．１〜５
重量％の範囲で用いられる。The amount of aluminum chloride used in the present invention is not particularly limited, but if it is too small, the reaction rate will be extremely slow, and if it is too large, it will be economically disadvantageous. Therefore, it is preferable to use benzene and polybromobenzene. 0.05 to 10% by weight, more preferably 0.1 to 5% by weight based on the sum of
It is used in a range of % by weight.
本発明に用いられるポリブロモベンゼンとはジブロモベ
ンゼンとトリブロモベンゼンである。ベンゼンとポリブ
ロモベンゼンの割合は（１）式で定義されるベンゼン／
ポリブロモベンゼン比で０．１〜１００であり、好まし
くは１〜５０であり、さらに好ましくは２〜２０である
。The polybromobenzenes used in the present invention are dibromobenzene and tribromobenzene. The ratio of benzene and polybromobenzene is defined by the formula (1): benzene/polybromobenzene
The polybromobenzene ratio is 0.1 to 100, preferably 1 to 50, and more preferably 2 to 20.
ベンゼン／ポリブロモベンゼン比；
ベンゼン（モル）
本発明における反応温度は原料を液相に保てる温度であ
れは特に制限はないが、あまり低温では塩化アルミニウ
ムの原料への溶解度が小さいため反応速度が極めて遅く
なり、又、あまり高温では、タール状生成物が多量に副
生ずるため、好ましくは、４０〜２００℃、さらに好ま
しくは、５０〜１５０℃の範囲で行われる。Benzene/polybromobenzene ratio; Benzene (mol) The reaction temperature in the present invention is not particularly limited as long as the raw material can be kept in a liquid phase, but if the temperature is too low, the reaction rate will be extremely low due to the low solubility of aluminum chloride in the raw material. The temperature is preferably 40 to 200°C, more preferably 50 to 150°C, since it becomes slow and a large amount of tar-like products are produced at too high a temperature.
本発明における圧力は原料を液相に保てる圧力であれば
どのような圧力でも良く、大気圧以上が好ましい。The pressure in the present invention may be any pressure as long as it can maintain the raw material in a liquid phase, and is preferably at least atmospheric pressure.
塩化アルミニウムは加水分解により失活し易いので、本
発明に用いられるベンゼンならびにポリブロモベンゼン
は水分含有量の少ない方が望ましい。Since aluminum chloride is easily deactivated by hydrolysis, it is desirable that the benzene and polybromobenzene used in the present invention have a low water content.
本発明における反応方式は流通方式９回分力式いずれで
も良い。The reaction method in the present invention may be either a circulation method or a 9-dose force method.
本発明の方法における生成物は塩化アルミニウムを分離
後、蒸留などの方式により回収できる。The product of the method of the present invention can be recovered by distillation or the like after separating aluminum chloride.
塩化アルミニウムの分離は水を加えて加水分解し抽出す
る方法などにより実施できる。Separation of aluminum chloride can be carried out by adding water to perform hydrolysis and extraction.
（発明の効果）
本発明の方法によりブロモベンゼン製造の際に副生ずる
ポリブロモベンゼンをブロモベンゼンに転喚し、ブロモ
ベンゼン製造原料の損失をなくすことができる。(Effects of the Invention) By the method of the present invention, polybromobenzene produced as a by-product during bromobenzene production can be converted to bromobenzene, thereby eliminating the loss of raw materials for bromobenzene production.
実施例を使って本発明を説明する。The invention will be explained using examples.
転化率２選択率は、以下の式によって求めた。The conversion rate 2 selectivity was determined by the following formula.
・ジブロモベンゼン転化量＝原料中のジブロモベンゼン
（ｍｏｌ）、生成物中のジブロモベンゼン（ｎ＋ｏｌ）
・トリブロモベンゼン転化量＝原料中のトリブロモベン
ゼン（ｍｏｌ）−生成物中のトリブロモベンゼン（ｍｏ
ｌ）とする。・Dibromobenzene conversion amount = dibromobenzene (mol) in the raw material, dibromobenzene (n+ol) in the product ・Tribromobenzene conversion amount = tribromobenzene (mol) in the raw material - tribromobenzene (mol) in the product
l).
ジブロモベンゼン転化率＝
ＩＷｔ Ｔ’）甲のシフロモベンゼン（ｍｏｌ）トリブ
ロモベンゼン転化率＝
ブロモベンゼン選択率＝
〔実施例１〕
ベンゼン（含水１６０ｐｐｍ） ５５ ｇとＯ−ブロ
モベンゼン（含水量１１００ｐｐ＋） ３５ｇを混合し
た均一溶液にＡｌＣｌ５１．０ｇ （１，１重量％）を
加え、耐圧容器中で８０℃で１時間攪拌して反応させた
。得られた溶液に、水１００ｇを加えて相分離させた後
、オイル相をガスクロマトグラフィーで分析した。その
結果、ジブロモベンゼン転化率＝９８％、ブロモベンゼ
ン選択率＝９２％であった。Dibromobenzene conversion rate = IWt T') Cyfromobenzene (mol) of A 51.0 g (1.1% by weight) of AlCl was added to a homogeneous solution obtained by mixing 35 g of AlCl, and the mixture was stirred at 80° C. for 1 hour to react in a pressure container. After adding 100 g of water to the obtained solution and causing phase separation, the oil phase was analyzed by gas chromatography. As a result, the dibromobenzene conversion rate was 98% and the bromobenzene selectivity was 92%.
〔実施例２〕
ベンゼン（含水量１０１００ｐｐ １０ ｇに、ｐ−ジ
ブロモベンゼン５ｇをとかして均一溶液に、ＱｌＩＣｌ
ｚｏ、 １ ｇ （０，７重量％）を加え、耐圧容器中
で１１０℃で３０分撹拌して反応させた。得られた溶液
に、水２０ｇを加えて相分離させた後、オイル相をガス
クロマトグラフィーで分析した。その結果、ジブロモベ
ンゼン転化率＝９６％、ブロモベンゼン選択率＝９３％
であった。[Example 2] Benzene (water content 10,100 pp 10 g, p-dibromobenzene 5 g was dissolved to make a homogeneous solution, QlICl
zo, 1 g (0.7% by weight) was added and reacted by stirring at 110° C. for 30 minutes in a pressure container. After adding 20 g of water to the obtained solution and causing phase separation, the oil phase was analyzed by gas chromatography. As a result, dibromobenzene conversion rate = 96%, bromobenzene selectivity = 93%
Met.
〔実施例３〕
ベンゼン（含水量３０ｐｐ＋ｓ） ３０ｇに一−ジブロ
モベンゼン（含水量８０Ｇ１ｐａ） ２０ｇを溶かした
均一溶液にＡｊ？Ｃｊ？ａ １．０ｇ （２，０重量％
）を加え、密閉容器中で４０℃、４時間攪拌して反応を
行った。得られた溶液に水５０ｇを加え相分離させた後
、オイル相をガスクロで分析した。その結果、ジブロモ
ベンゼン転化率＝９７％、ブロモベンゼン選択率＝９２
％であった。[Example 3] Aj? Cj? a 1.0g (2.0% by weight
) was added, and the reaction was carried out by stirring in a closed container at 40°C for 4 hours. After adding 50 g of water to the obtained solution and causing phase separation, the oil phase was analyzed by gas chromatography. As a result, dibromobenzene conversion rate = 97%, bromobenzene selectivity = 92
%Met.
〔実施例４〕
ベンゼン（含水量６０ｐｐｍ） １０ ｇに１．２．４
−１−ジブロモベンゼン５ｇを溶かした均一溶液に、Ａ
ｌＣｌ５Ｏ，２ｇ （１，３重量％）を加え、ガラス製
密閉容器中で７０℃、１時間攪拌して反応を行った。得
られた溶液に水２０ｇを加え相分離させた後、オイル相
をガスクロで分析した。その結果、１．２．４−トリブ
ロモベンゼン転化＄ ＝ １００％、ブロモベンゼン選
択率＝９２％であった。[Example 4] Benzene (water content 60 ppm) 1.2.4 per 10 g
- In a homogeneous solution of 5 g of 1-dibromobenzene, A
2 g (1.3% by weight) of lCl5O was added, and the reaction was carried out by stirring at 70° C. for 1 hour in a closed glass container. After adding 20 g of water to the obtained solution and causing phase separation, the oil phase was analyzed by gas chromatography. As a result, 1.2.4-tribromobenzene conversion $ = 100%, bromobenzene selectivity = 92%.
〔実施例５〕
ベンゼン（含水量８０ｐｐｍ） １００ｇにｐ−ジブロ
モベンゼン１０ｇ、Ｏ−ジブロモベンゼン３５ｇ、ｒａ
−ジブロモベンゼン２ｇ、１，２．４−トリブロモベン
ゼン１ｇを溶かした均一溶液に、ＡｌＣｌ１ｚ １．２
ｇ（０，８重量％）を加え、ガラス製耐圧容器中で８０
℃、２時間攪拌して反応を行った。得られた溶液に水１
００ｇを加え相分離させた後、オイル相をガスクロで分
析した。その結果、ジブロモベンゼン転化率＝９７％、
１．２．４− ）ジブロモベンゼン転化率＝１００％
、ブロモベンゼン選択率＝９１％であった。[Example 5] 100 g of benzene (water content 80 ppm), 10 g of p-dibromobenzene, 35 g of O-dibromobenzene, ra
- In a homogeneous solution of 2 g of dibromobenzene and 1 g of 1,2.4-tribromobenzene, add 1.2 g of AlCl1z.
g (0.8% by weight) and 80% by weight in a glass pressure container.
The reaction was carried out by stirring at ℃ for 2 hours. Add 1 part water to the resulting solution
After adding 00g and causing phase separation, the oil phase was analyzed by gas chromatography. As a result, dibromobenzene conversion rate = 97%,
1.2.4-) Dibromobenzene conversion rate = 100%
, bromobenzene selectivity=91%.
Claims (3)
てブロモベンゼンを製造する際に、塩化アルミニウムを
触媒として用いることを特徴とするブロモベンゼンの製
造法(1) A method for producing bromobenzene characterized by using aluminum chloride as a catalyst when producing bromobenzene by reacting benzene and polybromobenzene in a liquid phase.
ベンゼンの和に対して０．０５〜１０重量％である特許
請求の範囲第１項記載の方法(2) The method according to claim 1, wherein the amount of aluminum chloride is 0.05 to 10% by weight based on the sum of benzene and polybromobenzene.
の範囲第１項記載の方法(3) The method according to claim 1, wherein the reaction temperature is in the range of 40 to 200°C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60259724A JPS62120329A (en) | 1985-11-21 | 1985-11-21 | Production of bromobenzene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60259724A JPS62120329A (en) | 1985-11-21 | 1985-11-21 | Production of bromobenzene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS62120329A true JPS62120329A (en) | 1987-06-01 |
Family
ID=17338064
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60259724A Pending JPS62120329A (en) | 1985-11-21 | 1985-11-21 | Production of bromobenzene |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62120329A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4808759A (en) * | 1986-08-11 | 1989-02-28 | Montedipe S.P.A. | Process for the catalytic trans-halogenation of a poly-iodo-benzene |
| US4822929A (en) * | 1986-08-11 | 1989-04-18 | Montedipe S.P.A. | Process for the catalytic trans-halogenation of a polyiodo-benzene, and, in particular, of a di-iodo-benzene |
-
1985
- 1985-11-21 JP JP60259724A patent/JPS62120329A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4808759A (en) * | 1986-08-11 | 1989-02-28 | Montedipe S.P.A. | Process for the catalytic trans-halogenation of a poly-iodo-benzene |
| US4822929A (en) * | 1986-08-11 | 1989-04-18 | Montedipe S.P.A. | Process for the catalytic trans-halogenation of a polyiodo-benzene, and, in particular, of a di-iodo-benzene |
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