JPS61286347A - Production of 2,4,6-tribromophenyl acrylate - Google Patents
Production of 2,4,6-tribromophenyl acrylateInfo
- Publication number
- JPS61286347A JPS61286347A JP60125128A JP12512885A JPS61286347A JP S61286347 A JPS61286347 A JP S61286347A JP 60125128 A JP60125128 A JP 60125128A JP 12512885 A JP12512885 A JP 12512885A JP S61286347 A JPS61286347 A JP S61286347A
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- chloropropionyl chloride
- tribromophenol
- mol
- chloride
- 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
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
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は他の重合性モノマー類と共重合させることによ
り、共重合樹脂に難燃性または高屈折率を賦与するため
１（有用な２，４．６−）リブロモフェニルアクリレー
トの製造方法に関する。Detailed Description of the Invention (Industrial Field of Application) The present invention aims to impart flame retardancy or a high refractive index to a copolymer resin by copolymerizing it with other polymerizable monomers. , 4.6-) relates to a method for producing ribromophenyl acrylate.
（従来の技術）
２．４．６−ドリブロモフエニルアクリレートの製造法
としては、従来２，４．６−）リブロモフェノールとア
クリル酸クロライドから合成する方法（日本化学会誌、
１９７４年（４巻）７７９〜７８３頁）および２，４．
６−１リプロモフエノールとアクリル酸および塩化チオ
ニルによる合成方法（特開昭５０−１３７９３８ ）が
知られている。(Prior art) As a method for producing 2.4.6-dribromophenyl acrylate, a conventional method of synthesizing it from 2,4.6-)ribromophenol and acrylic acid chloride (Journal of the Chemical Society of Japan,
1974 (4 volumes, pp. 779-783) and 2, 4.
A synthetic method using 6-1 lipromophenol, acrylic acid and thionyl chloride (Japanese Patent Application Laid-Open No. 137938/1983) is known.
前者の方法において、アクリル酸クロライドはアクリル
酸と塩化チオニルから製造されるものであり１本質的に
は両者ともに塩化チオニルを必要とするものである。こ
の塩化チオニルを用いる反応は亜硫酸ガスの発生を併う
ものであり、工業的に必ずしも有利な方法とは云えない
。In the former method, acrylic acid chloride is produced from acrylic acid and thionyl chloride, both of which essentially require thionyl chloride. This reaction using thionyl chloride involves the generation of sulfur dioxide gas, and cannot necessarily be said to be an industrially advantageous method.
（発明が解決しようとする問題点）
本発明の課題はアクリル酸クロライドを原料とする従来
方法の欠点を解消し、より工業的に２゜４．６−１リブ
ロモフエニルアクリレートを製造する方法を提供するこ
とである。(Problems to be Solved by the Invention) The problem of the present invention is to solve the drawbacks of the conventional method using acrylic acid chloride as a raw material, and to develop a method for producing 2°4.6-1 ribomophenyl acrylate more industrially. It is to provide.
（問題点を解決するための手段）
本発明者らは、上記課題達成のために、従来、原料とし
て用いられていたアクリル酸クロライドに替わるものと
して、アクリル酸クロライドにくらべると容易に得られ
る。すなわち、アクリル酸マタハβ−クロロプロピオン
酸とフォスゲンとの反応により容易に得られるβ−クロ
ロプロピオニルクロライドを原料とする２、４．６−）
リブロモフェニルアクリレートの製造方法について鋭意
検討した。(Means for Solving the Problems) In order to achieve the above-mentioned problems, the present inventors have found that they can be easily obtained as a substitute for acrylic acid chloride, which has been conventionally used as a raw material, compared to acrylic acid chloride. That is, 2,4.6-) which uses β-chloropropionyl chloride easily obtained by the reaction of acrylic acid and β-chloropropionic acid with phosgene as a raw material.
A method for producing ribromophenyl acrylate was intensively studied.
その結果、β−クロロプロピオニルクロライドを原料と
して使用すると１選択された塩酸捕獲剤および特定され
た反応条件によって、２，４．６− ） ＩＪ ブロモ
フェノールとβ−クロロプロピオニルクロライドを反応
させると、エステル化反応とオレフィン化反応を２段階
に行わせることなく、比較的温和な条件で同時に進行す
ることを見出し。As a result, when β-chloropropionyl chloride is used as a raw material, depending on the selected hydrochloric acid scavenger and the specified reaction conditions, 2,4.6-)IJ When bromophenol and β-chloropropionyl chloride are reacted, the ester It was discovered that the chemical reaction and the olefin reaction can proceed simultaneously under relatively mild conditions, without having to perform them in two stages.
本発明を完成するに到った。The present invention has now been completed.
すなわち０本発明は２ 、４ 、６−トリブロモフェノ
ールを極性有機溶媒中、−１０〜３５℃の温度で、２，
４．６−ＩＪジブロモェノール１モルに対して１．８〜
２．５０モルの苛性ソーダまたは苛性カリ水溶液の存在
下β−クロロプロピオニルクロライドと反応させるとと
を特徴とする２、４゜６−トリブロモフェニルアクリレ
ートの製造方法である。That is, the present invention provides 2,4,6-tribromophenol in a polar organic solvent at a temperature of -10 to 35°C.
4.6-IJ 1.8 to 1 mole of dibromoenol
A process for producing 2,4°6-tribromophenyl acrylate, which comprises reacting with β-chloropropionyl chloride in the presence of 2.50 mol of caustic soda or caustic potassium aqueous solution.
本発明の方法に用いる極性有機溶媒としては。The polar organic solvent used in the method of the present invention includes:
２．４．６−トリブロモフェノールを溶解し、かつ水と
相溶性の良い有機溶媒であれば、いずれも使用できるが
、好ましくはアセトン、メチルエチルケトンなどのケト
ン類またはＮ、Ｎ−ジメチルフォルムアミド、ジメチル
スルフオキシドを用いる。その使用量は２ ＋ ４ ＋
６−ト’）ブロモフェノールに対して１〜２０重量倍
である。また使用する苛性ソーダまたは苛性カリ水溶液
の濃度について制限はないが、水溶液として安定な５０
重量％以下が好ましく、使用する苛性ソーダまたは苛性
カリの使用量は、２．４．６−トリブロモフェノールに
対して１．８〜２．５ モル比である。苛性ソーダま
たは苛性カリが１．８モル比未満では、未反応の２．４
．６−）リブロモフェノールの残存量が多くなり、製品
中に混入して重合を阻害する原因になり易く、また２、
５ モル比を越えるとβ−クロロプロピオニルクロラ
イドの加水分解反応を起し易くなり、β−クロロプロピ
オニルクロライドをベースとする２、４．６−ドリブロ
モフエニルアクリレートの収率が低下する。Any organic solvent can be used as long as it dissolves 2.4.6-tribromophenol and is compatible with water, but preferably ketones such as acetone and methyl ethyl ketone, or N,N-dimethylformamide, Using dimethyl sulfoxide. The amount used is 2 + 4 +
6-t') 1 to 20 times the weight of bromophenol. There are no restrictions on the concentration of caustic soda or caustic potassium aqueous solution used, but 50% is stable as an aqueous solution.
The amount of caustic soda or potassium hydroxide used is preferably 1.8 to 2.5 molar ratio to 2.4.6-tribromophenol. If the molar ratio of caustic soda or caustic potash is less than 1.8, unreacted 2.4
．． 6-) The residual amount of ribromophenol increases, which tends to mix into the product and inhibit polymerization;
If the molar ratio exceeds 5, the hydrolysis reaction of β-chloropropionyl chloride tends to occur, and the yield of 2,4,6-dribromophenyl acrylate based on β-chloropropionyl chloride decreases.
また、使用するβ−クロロプロピオニルクロライドの使
用量は２，４．６−トリブロモフェノールに対して０，
９〜１，２５モル比である。In addition, the amount of β-chloropropionyl chloride used is 0.
The molar ratio is 9 to 1.25.
β−クロロプロピオニルクロライドが０．９モル比未満
では、上記同様に未反応の２．４．６−ト！Ｊブロモフ
エノールの残存量が多くなり、また１、２５モル比を越
えるとβ−クロロプロピオニルクロライドの残存量が増
加し１反応液に水を加えたのちに晶出する固体粉末に刺
激臭を残す原因となるばかりでなく、再結晶化工程で重
合反応物を生成し。If the molar ratio of β-chloropropionyl chloride is less than 0.9, unreacted 2,4,6-t! The residual amount of J-bromophenol increases, and when the molar ratio exceeds 1.25, the residual amount of β-chloropropionyl chloride increases, leaving a pungent odor in the solid powder that crystallizes after adding water to the reaction solution. It not only causes the reaction, but also generates polymerization reactants during the recrystallization process.
製品に混入する原因となり易い。It can easily become a cause of contamination in products.
さらに１本発明における反応温度は一１Ｏ〜３５℃であ
るが、特に好ましくは０〜１０℃である。Furthermore, the reaction temperature in the present invention is -10 to 35°C, particularly preferably 0 to 10°C.
低過ぎる場合は、２，４．６−ドリブロモフエニルーβ
−クロロプロピオネートからのオレフィン化反応が進み
にくくなり、高過ぎる場合は、β−クロロプロピオニル
クロライドの加水分解を起し。If it is too low, 2,4.6-dribromophenyl β
- The olefinization reaction from chloropropionate becomes difficult to proceed, and if the temperature is too high, hydrolysis of β-chloropropionyl chloride occurs.
収率の低下を起すのみならず、２．４．６−トＩＪブロ
モフエニルアクリレートの加水分解反応も併発する。Not only does this result in a decrease in yield, but also a hydrolysis reaction of 2,4,6-IJ bromophenyl acrylate occurs.
かくして１本発明の方法の一般的実施態様としては、２
，４．６−）リプロモフェノールを極性有機溶媒に溶解
した液を攪きまぜ、かつ、内温を一１０〜３５℃になる
ように冷却しながら、２゜４ 、６− ） ＩＪ ブロ
モフェノール１モルに対し、 １．８〜２．５０モルの
苛性ソーダまたは苛性カリ水溶液を全量加えたのち、０
．９〜１．２５モルのβ−クロロプロピオニルクロライ
ドを滴下ロートから２〜８時間かげて滴下するか、また
は１．８〜２．５ モルの苛性ソーダまたは苛性カリ
水溶液と０．９〜１．２５モルノβ−クロロプロピオニ
ルクロライドを別々の滴下ロートより同時に２〜８時間
かけて滴下することにより２．４．６−ドリブロモフエ
ニルアクリレートを高収率で生成させることができる。Thus, 1. General embodiments of the method of the invention include 2.
, 4.6-) IJ bromophenol while stirring the solution of libromophenol dissolved in a polar organic solvent and cooling it to an internal temperature of -10 to 35°C. After adding 1.8 to 2.50 moles of caustic soda or caustic potassium aqueous solution to 1 mole,
．． 9 to 1.25 moles of β-chloropropionyl chloride is added dropwise from the dropping funnel over a period of 2 to 8 hours, or 1.8 to 2.5 moles of caustic soda or aqueous caustic potassium solution and 0.9 to 1.25 moles of β By simultaneously dropping -chloropropionyl chloride from separate dropping funnels over a period of 2 to 8 hours, 2.4.6-dribromophenyl acrylate can be produced in high yield.
さらに、この反応液に水を加えることにより２，４゜を
６−ドリプロモフエールアクリレートの粗結晶〆晶出さ
せ、濾過により粗結晶を取り出し、これをアルコール９
％にイソプロピルアルコールを再結晶化溶剤として再結
晶化を行うことにより、所望の２．’４．６−トリブロ
モフェニルアクリレートを高純度でかつ高収率で得るこ
とができる。Furthermore, by adding water to this reaction solution, 2,4° was crystallized into crude crystals of 6-dolibromophere acrylate, the crude crystals were taken out by filtration, and this was mixed with alcohol 9
% by recrystallizing using isopropyl alcohol as a recrystallization solvent. '4,6-Tribromophenyl acrylate can be obtained with high purity and high yield.
（作用および効果）
本発明の方法によれば、２．４．６−）ＩＪジブロモェ
ノールにβ−クロロプロピオニルクロライドを極性有機
溶媒中、苛性ソーダまたは苛性カリ水溶液の存在下に反
応させてエステル化とオレフィン化とを同時に進行させ
、２段階の反応によることなく、一段の反応で２．４．
６−トＩＪブロモフエニルアクリレートを得ることがで
きる。(Functions and Effects) According to the method of the present invention, 2.4.6-) IJ dibromoenol is reacted with β-chloropropionyl chloride in a polar organic solvent in the presence of caustic soda or caustic potassium aqueous solution to esterify and olefin. 2.4. in a single step reaction without a two-step reaction.
6-tIJ bromophenyl acrylate can be obtained.
この方法に用いるβ−クロロプロピオニルクロライドは
工業的に入手し易い原料であり１本発明の方法は経済的
にも、工業的にも工業的価値のある製造方法である。β-chloropropionyl chloride used in this method is an industrially easily available raw material, and the method of the present invention is an industrially valuable manufacturing method both economically and industrially.
（実施例） 以下、実施例により本発明を詳述する。(Example) Hereinafter, the present invention will be explained in detail with reference to Examples.
例中に示す部はすべて重量部である。All parts shown in the examples are parts by weight.
実施例１
アセトン５０部に２ 、４ 、６−１−リプロモフェノ
ール１６．５部（０，０５モル）を加え、攪きまぜなが
ら内容液の温度が５℃になるように冷却し、２５重量％
苛性ソーダ水溶液１６．８部（０，１１モル）を加えた
のち、β−クロロプロピオニルクロライド６．５部（０
，０５モル）を２時間かけて滴下したのち、攪きまぜを
２時間続げた。次に水６５部を加えると粉末状の固体が
析出した。固体を沖過して分離したのちイソプロピルア
ルコールから再結晶化を行ない、１７．５部の無色の柱
状結晶を得た。融点７８〜７９℃１元素分析値はＣ；２
８．１０重量％（計算値２８．０９重量％）、 Ｉ−Ｔ
； １．１４重量％（１，３１重量％）、Ｂｒ；６２
．１８重量％ （６２，２９重量％）液体クロマトグラ
フィーによる分析から純度９９％であり、２．４．６−
１リブロモフエノールをベースとした収率９０モル％で
あった。Example 1 16.5 parts (0.05 mol) of 2,4,6-1-lipromophenol was added to 50 parts of acetone, and cooled while stirring so that the temperature of the contents reached 5°C. weight%
After adding 16.8 parts (0.11 mol) of caustic soda aqueous solution, 6.5 parts (0.11 mol) of β-chloropropionyl chloride was added.
, 05 mol) was added dropwise over 2 hours, and stirring was continued for 2 hours. Next, 65 parts of water was added to precipitate a powdery solid. After the solid was separated by filtration, it was recrystallized from isopropyl alcohol to obtain 17.5 parts of colorless columnar crystals. Melting point 78-79℃ 1 elemental analysis value C; 2
8.10% by weight (calculated value 28.09% by weight), I-T
; 1.14% by weight (1,31% by weight), Br; 62
．． 18% by weight (62.29% by weight) Analysis by liquid chromatography showed a purity of 99%, 2.4.6-
The yield was 90 mol% based on 1ribromophenol.
実施例２
Ｎ、Ｎ−ジメチルフォルムアミド３００部に２゜４．６
−１リブロモフェノール９９．０部（０，３０モル）を
溶解させ、攪きまぜを行ない内温を１０℃に保ちながら
３５％苛性カリ水溶液１０６．０部（０，６６モル）お
よびβ−クロロプロピオニルクロライド３８．７部（０
，３０モル）を別々の滴下ロートから３時間かけて滴下
したのち、攪きまぜを２時間続けた。次に水６００部を
加えてなお攪きまぜを続けると粉末状の固体が析出した
。濾過して得た固体をイソプロピルアルコールで再結晶
化を行ない無色のプリズム状結晶ｉ ０６． ｉ部を得
た。Example 2 2°4.6 to 300 parts of N,N-dimethylformamide
-1 Libromophenol (99.0 parts (0.30 mol)) was dissolved, stirred, and while maintaining the internal temperature at 10°C, 106.0 parts (0.66 mol) of a 35% caustic potassium aqueous solution and β-chloro 38.7 parts of propionyl chloride (0
, 30 mol) were added dropwise from separate dropping funnels over 3 hours, and stirring was continued for 2 hours. Next, 600 parts of water was added and stirring was continued to precipitate a powdery solid. The solid obtained by filtration was recrystallized with isopropyl alcohol to obtain colorless prismatic crystals i 06. I got part i.
液体クロマトグラフィーによる分析から純度９９％テア
リ、２，４．６−）リブロモフェノールをベースとした
収率は９１モル％であった。Analysis by liquid chromatography showed that the purity was 99% and the yield was 91 mol% based on 2,4.6-)ribromophenol.
Claims (1)
中、−１０〜３５℃の温度で２，４，６−トリブロモフ
ェノール１モルに対して１．８〜２．５モルの苛性ソー
ダまたは苛性カリ水溶液および０．９〜１．２５モルの
β−クロロプロピオニルクロライドを加えてエステル化
反応およびオレフィン化反応を同時に行うことを特徴と
する２，４，６−トリブロモフェニルアクリレートの製
造方法。1) 2,4,6-tribromophenol in a polar organic solvent at a temperature of -10 to 35°C with 1.8 to 2.5 mol of caustic soda per 1 mol of 2,4,6-tribromophenol or A method for producing 2,4,6-tribromophenyl acrylate, which comprises adding an aqueous caustic potassium solution and 0.9 to 1.25 mol of β-chloropropionyl chloride to simultaneously carry out an esterification reaction and an olefination reaction.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60125128A JPH0649666B2 (en) | 1985-06-11 | 1985-06-11 | Process for producing 2,4,6-tribromophenyl acrylate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60125128A JPH0649666B2 (en) | 1985-06-11 | 1985-06-11 | Process for producing 2,4,6-tribromophenyl acrylate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61286347A true JPS61286347A (en) | 1986-12-16 |
| JPH0649666B2 JPH0649666B2 (en) | 1994-06-29 |
Family
ID=14902542
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60125128A Expired - Lifetime JPH0649666B2 (en) | 1985-06-11 | 1985-06-11 | Process for producing 2,4,6-tribromophenyl acrylate |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0649666B2 (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5679833A (en) * | 1993-09-15 | 1997-10-21 | Allied Colloids Limited | Synthesis of vinyl esters |
| WO1998050340A1 (en) * | 1997-05-09 | 1998-11-12 | Minnesota Mining And Manufacturing Company | High index of refraction monomers |
| US5932626A (en) * | 1997-05-09 | 1999-08-03 | Minnesota Mining And Manufacturing Company | Optical product prepared from high index of refraction brominated monomers |
| US6107364A (en) * | 1997-05-09 | 2000-08-22 | 3M Innovative Properties Company | Methyl styrene as a high index of refraction monomer |
| US6355754B1 (en) | 1997-05-09 | 2002-03-12 | 3M Innovative Properties Company | High refractive index chemical composition and polymers and polymeric material derived therefrom |
| JP2009029801A (en) * | 2007-07-02 | 2009-02-12 | Mitsubishi Chemicals Corp | Naphthohydroquinone mono(meth)acrylate and method for producing the same |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4943531A (en) * | 1972-08-30 | 1974-04-24 | ||
| JPS5091416A (en) * | 1973-12-07 | 1975-07-22 | Facit Ab |
-
1985
- 1985-06-11 JP JP60125128A patent/JPH0649666B2/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4943531A (en) * | 1972-08-30 | 1974-04-24 | ||
| JPS5091416A (en) * | 1973-12-07 | 1975-07-22 | Facit Ab |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5679833A (en) * | 1993-09-15 | 1997-10-21 | Allied Colloids Limited | Synthesis of vinyl esters |
| WO1998050340A1 (en) * | 1997-05-09 | 1998-11-12 | Minnesota Mining And Manufacturing Company | High index of refraction monomers |
| US5932626A (en) * | 1997-05-09 | 1999-08-03 | Minnesota Mining And Manufacturing Company | Optical product prepared from high index of refraction brominated monomers |
| US6107364A (en) * | 1997-05-09 | 2000-08-22 | 3M Innovative Properties Company | Methyl styrene as a high index of refraction monomer |
| US6355754B1 (en) | 1997-05-09 | 2002-03-12 | 3M Innovative Properties Company | High refractive index chemical composition and polymers and polymeric material derived therefrom |
| JP2009029801A (en) * | 2007-07-02 | 2009-02-12 | Mitsubishi Chemicals Corp | Naphthohydroquinone mono(meth)acrylate and method for producing the same |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0649666B2 (en) | 1994-06-29 |
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