JPH02264754A - Production of (tribromomethyl) phenyl sulfone - Google Patents
Production of (tribromomethyl) phenyl sulfoneInfo
- Publication number
- JPH02264754A JPH02264754A JP8835989A JP8835989A JPH02264754A JP H02264754 A JPH02264754 A JP H02264754A JP 8835989 A JP8835989 A JP 8835989A JP 8835989 A JP8835989 A JP 8835989A JP H02264754 A JPH02264754 A JP H02264754A
- Authority
- JP
- Japan
- Prior art keywords
- phenyl sulfone
- tribromomethyl
- reaction
- hypobromite
- alkali
- 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
- DWWMSEANWMWMCB-UHFFFAOYSA-N tribromomethylsulfonylbenzene Chemical compound BrC(Br)(Br)S(=O)(=O)C1=CC=CC=C1 DWWMSEANWMWMCB-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- JCDWETOKTFWTHA-UHFFFAOYSA-N methylsulfonylbenzene Chemical compound CS(=O)(=O)C1=CC=CC=C1 JCDWETOKTFWTHA-UHFFFAOYSA-N 0.000 claims abstract description 26
- 238000000034 method Methods 0.000 claims abstract description 17
- JGJLWPGRMCADHB-UHFFFAOYSA-N hypobromite Chemical compound Br[O-] JGJLWPGRMCADHB-UHFFFAOYSA-N 0.000 claims abstract description 16
- CRWJEUDFKNYSBX-UHFFFAOYSA-N sodium;hypobromite Chemical compound [Na+].Br[O-] CRWJEUDFKNYSBX-UHFFFAOYSA-N 0.000 claims abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000003513 alkali Substances 0.000 claims abstract description 11
- 239000002904 solvent Substances 0.000 claims abstract description 7
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 3
- 238000005893 bromination reaction Methods 0.000 claims description 7
- 230000031709 bromination Effects 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 abstract description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Substances [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract description 4
- 239000006227 byproduct Substances 0.000 abstract description 3
- 239000011342 resin composition Substances 0.000 abstract description 3
- -1 NaOH or KOH Chemical class 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- 239000013078 crystal Substances 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000007900 aqueous suspension Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 150000003457 sulfones Chemical class 0.000 description 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- RLOBRCXIAWJACX-UHFFFAOYSA-N dibromomethylsulfonylbenzene Chemical compound BrC(Br)S(=O)(=O)C1=CC=CC=C1 RLOBRCXIAWJACX-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 239000003791 organic solvent mixture Substances 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- ORQYPOUSZINNCB-UHFFFAOYSA-N potassium;hypobromite Chemical compound [K+].Br[O-] ORQYPOUSZINNCB-UHFFFAOYSA-N 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- SFKTYEXKZXBQRQ-UHFFFAOYSA-J thorium(4+);tetrahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[Th+4] SFKTYEXKZXBQRQ-UHFFFAOYSA-J 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/14—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/04—Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- 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）
本発明は感光性樹脂組成物の一構成成分である（トリブ
ロモメチル）フェニルスルホンの製造法に関する。DETAILED DESCRIPTION OF THE INVENTION (Industrial Field of Application) The present invention relates to a method for producing (tribromomethyl)phenyl sulfone, which is a component of a photosensitive resin composition.
感光性樹脂組成物中における（トリブロモメチル）フェ
ニルスルホンは、ロイコ染料等との組合せにおいて光発
色し、感光性樹脂の露光部、未露光部のコントラストを
良好にしたり、活性線照射によりハロゲンラジカルを発
生させ、ハロゲン化水素を生成し、感光性樹脂と基材と
の密着性を向上せしめ、耐めっき性を高める等の重要な
作用があるといわれており、産業上の利用価値はきわめ
て大きい。(Tribromomethyl) phenyl sulfone in the photosensitive resin composition produces photocolor when combined with leuco dye, etc., improves the contrast between exposed and unexposed areas of the photosensitive resin, and removes halogen radicals by irradiation with actinic rays. It is said to have important effects such as generating hydrogen halide, improving the adhesion between the photosensitive resin and the base material, and increasing plating resistance, and has extremely high industrial value. .
（従来の技術）
（発明が解決しようとする問題点）
メチルフェニルスルホンを原料とし、（トリブロモメチ
ル）フェニルスルホンを得る方法としてＪ、Ｏｒｇ、Ｃ
ｈｅｒｎ、、５１巻、３３６９頁、１９８６年記載の方
法が知られている。(Prior art) (Problems to be solved by the invention) J, Org, C as a method for obtaining (tribromomethyl) phenyl sulfone using methyl phenyl sulfone as a raw material.
Hern, Vol. 51, p. 3369, 1986, is known.
この方法においては、臭素化剤として次亜臭素酸ナトリ
ウムを用い、ジオキサン−水の混合溶媒中、メチルフェ
ニルスルホンを均一に溶解し、強アルカリ性の下、室温
にて２４時間を要して反応を行ない、（トリブロモメチ
ル）フェニルスルホンを得ている。In this method, sodium hypobromite is used as a brominating agent, methylphenylsulfone is uniformly dissolved in a mixed solvent of dioxane and water, and the reaction takes 24 hours at room temperature under strong alkalinity. (tribromomethyl) phenyl sulfone was obtained.
しかしながら、この方法はアルカリおよび次亜臭素酸ナ
トリウムの使用量が、原料のメチルフェニルスルホンに
対し、各々２１．５倍モルおよび６倍モルと非常に多く
、特に次亜臭素酸ナトリウムは理論量（３倍モル）の２
倍量使用しなければならない。However, in this method, the amounts of alkali and sodium hypobromite used are extremely large, 21.5 times the mole and 6 times the mole of the raw material methylphenylsulfone, respectively.In particular, sodium hypobromite is used in a theoretical amount ( 3 times mole) of 2
Must use double the amount.
さらに反応時間も２４時間という長時間を要し、しかも
、得られた（トリブロモメチル）フェニルスルホンは純
度が悪く、使用については再結晶を要する等工業的実施
に際しては、決して優れた方法とはいい難い。我々のト
レース実験では、反応温度を高くすると、次亜臭素酸ナ
トリウムの添加途中で反応が進行しなくなり、目的物を
低収率でしか得られなかった。Furthermore, the reaction time is as long as 24 hours, and the obtained (tribromomethyl)phenyl sulfone has poor purity and requires recrystallization before use.This method is by no means an excellent method for industrial implementation. Good and difficult. In our trace experiments, when the reaction temperature was raised, the reaction stopped progressing during the addition of sodium hypobromite, and the desired product could only be obtained in low yield.
（問題点を解決するための手段）
そこで本発明者等は、反応が途中で進行しなくなる原因
を追求し、次のような知見を得た。(Means for Solving the Problems) Therefore, the present inventors investigated the cause of the reaction stopping midway through, and obtained the following knowledge.
（１） 次亜臭素酸ナトリウムがジオキサン−水混合
溶媒中のジオキサンと反応して、目的とする臭素化反応
に与らないで消費される。(1) Sodium hypobromite reacts with dioxane in the dioxane-water mixed solvent and is consumed without participating in the desired bromination reaction.
（２） 次亜臭素酸ナトリウムとジオキサンとの反応
は、文献記載の室温にても十分進行するが、高温ではさ
らに促進される。(2) The reaction between sodium hypobromite and dioxane proceeds satisfactorily even at the room temperature described in the literature, but is further accelerated at high temperatures.
（３） 得られた（トリブロモメチル）フェニルスル
ホン中に、副生じた（ジブロモメチル）フェニルスルホ
ンが含まれる。(3) The obtained (tribromomethyl) phenyl sulfone contains by-product (dibromomethyl) phenyl sulfone.
これらの問題を解決するため、水−ジオキサン系のジオ
キサンに代えて、次亜臭素酸ナトリウムにより酸化され
難く、また、メチルフェニルスルホンを溶解する有機溶
媒を種々検討したが、結局は、ジオキサン同様、次亜臭
素酸す［・リウムにより酸化され、適当な溶媒を見出す
ことはできなかった。In order to solve these problems, we investigated various organic solvents that are resistant to oxidation by sodium hypobromite and that dissolve methylphenylsulfone in place of water-dioxane-based dioxane, but in the end, like dioxane, It was oxidized by sodium hypobromite and no suitable solvent could be found.
そこで本発明者等は水−有機溶媒混合系に代えて、水単
独を反応溶媒として用いることに想到し、鋭意検討の結
果、アルカリの存在下に前記反応を行なうと意外にもメ
チルフェニルスルホンの臭素化が短時間で効率よ（行な
われることを見出し、本発明を完成するに至った。この
場合、アルカリは本来水不溶性の結晶であるメチルフェ
ニルスルホンを液状とする作用があるが、反応系は均一
とはならず、液−液の不均一二相系となる。しかし反応
が進行するに従って、生成した（トリブロモメチル）フ
ェニルスルホンは固体として析出するため、最終的には
固−液系で反応は終了する。Therefore, the present inventors came up with the idea of using water alone as a reaction solvent instead of a water-organic solvent mixture system, and as a result of intensive studies, they found that methylphenylsulfone was unexpectedly The present inventors discovered that bromination can be carried out efficiently in a short period of time, leading to the completion of the present invention. In this case, the alkali has the effect of making methylphenylsulfone, which is originally a water-insoluble crystal, into a liquid state, but the reaction system is not homogeneous and becomes a liquid-liquid heterogeneous two-phase system.However, as the reaction progresses, the generated (tribromomethyl)phenyl sulfone precipitates as a solid, so it ultimately becomes a solid-liquid system. The reaction ends in the system.
この時、（トリブロモメチル）フェニルスルホンは全量
が固体として反応系に安定して存在するため、ジオキサ
ンを用いた場合に、それに溶解した（トリブロモメチル
）フェニルスルホンからの副反応による純度低下といっ
た問題がなく、高純度の（トリブロモメチル）フェニル
スルホンを簡単な工程で収率よく得ることができる。At this time, (tribromomethyl) phenyl sulfone exists stably in the reaction system as a solid in its entirety, so when dioxane is used, there is a possibility that the purity will decrease due to side reactions from (tribromo methyl) phenyl sulfone dissolved in dioxane. There are no problems and highly pure (tribromomethyl)phenyl sulfone can be obtained in good yield through a simple process.
以上述べた如く、本発明の要旨は、メチルフェニルスル
ホンを臭素化して（トリブロモメチル）フェニルスルホ
ンを得るに際し、アルカリの存在下、水を溶媒として用
いることを特徴とする（トリブロモメチル）フェニルス
ルホンの製造法である。As stated above, the gist of the present invention is to obtain (tribromomethyl)phenyl sulfone by using water as a solvent in the presence of an alkali when brominating methylphenylsulfone to obtain (tribromomethyl)phenyl sulfone. This is a method for producing sulfone.
Ｂ「
本発明の方法によると、次亜臭素酸塩は全てメチルフェ
ニルスルホンとの反応に用いられるため、その使用量は
、メチルフェニルスルホンに対して３．１〜３．５倍モ
ルで十分である。B: According to the method of the present invention, all of the hypobromite is used in the reaction with methylphenylsulfone, so the amount used is 3.1 to 3.5 times the molar amount of methylphenylsulfone. be.
次亜臭素酸塩としては、次亜臭素酸ナトリウム。Sodium hypobromite is a hypobromite.
次亜臭素酸カリウムなどが挙げられるが、なかでも次亜
臭素酸ナトリウムが好適に用いられる。その濃度は、１
．０〜３０％の任意の濃度のものが使用司能である。Examples include potassium hypobromite, among which sodium hypobromite is preferably used. Its concentration is 1
．． Any concentration from 0 to 30% may be used.
反応に用いるアルカリとし′−（゛。゛は、水酸化ナト
リウム、水酸化カリウ１１などのアルカリ金属の水酸化
物が挙げられ、その量は、メチルフェニルスルホンに対
し、０．５〜２倍モルで十分であり、これにより本来水
不溶性の結晶Ｃあるメチルフエ−４４スルホンは液状と
なる。The alkali used in the reaction is an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide, and the amount thereof is 0.5 to 2 times the mole of methylphenylsulfone. is sufficient, and as a result, the methylphene-44 sulfone, which is essentially water-insoluble crystal C, becomes liquid.
反応は通常、メチルフェニルスルホンの水懸濁液に前記
濃度の次亜臭素酸ナトリウム水溶液を滴下して行なう。The reaction is usually carried out by dropping an aqueous solution of sodium hypobromite at the above concentration into an aqueous suspension of methylphenylsulfone.
一方臭素化反応生成物である（トリブロモメチル）フェ
ニルスルホンは、水に難溶性であるため、反応後に析出
する結晶をン濾過Ｊ−るだけで高純度の製品を得ること
ができる。On the other hand, since (tribromomethyl) phenyl sulfone, which is a bromination reaction product, is poorly soluble in water, a highly pure product can be obtained simply by filtering the crystals that precipitate after the reaction.
本発明の方法に、よれば、反応溶媒として有機溶剤を使
用しないため、溶剤回収操作を必要とせず工業的実施に
あた−って゛は特に有利である、溶媒として用いる水の
爪は特に限定されるものではないが、前述のごとく臭素
化反応生成物である（トリブロモメチル）フェニルスル
ホン・が１．水に難溶性であり、反応の途中から析出し
、てくるためスラリー濃度および容積効率を考慮１−で
決定する必要がある。その量は原料メチルフェニルスル
ポン１モルに対ｉ、 ｓ ｏ ｏ・〜２０００ｇが適量
である。According to the method of the present invention, since no organic solvent is used as a reaction solvent, there is no need for a solvent recovery operation, which is particularly advantageous in industrial implementation. However, as mentioned above, the bromination reaction product (tribromomethyl)phenylsulfone is 1. Since it is sparingly soluble in water and precipitates during the reaction, it is necessary to take slurry concentration and volumetric efficiency into account when deciding. The appropriate amount is i, so o.~2000 g per 1 mole of raw material methylphenyl sulfone.
反応温度は３０〜ｉｏｏ’ｅが好まｊ、い、、この温度
範囲では（トリブロモメチル）フェニルスルホンの結晶
状態も良好で、好結果が得られる。：３０°Ｃ未満では
反応速度が遅く、反応に長時間を要し、１００℃を超え
ると分解生成物を生ずるおそれがあり、いずれも得策で
ない。The reaction temperature is preferably 30 to ioo'e. In this temperature range, the crystal state of (tribromomethyl)phenyl sulfone is also good and good results can be obtained. : If it is less than 30°C, the reaction rate will be slow and the reaction will take a long time, and if it exceeds 100°C, decomposition products may be produced, so neither is a good idea.
本発明において原料としで用いるメチルフェニルスルホ
ンは、公知の物質であり、種々の方法により容易に得る
ことができる。Methylphenyl sulfone, which is used as a raw material in the present invention, is a known substance and can be easily obtained by various methods.
その１例を挙げると
１） ヂオアニソールの酸化による方法３゜２） ベニ
／セ゛ンとメタンスルホニルクロリドフリーデルクラフ
ト反応による方法。Examples include 1) a method based on the oxidation of dioanisole; 2) a method based on the Friedel-Crafts reaction with beni/thane and methanesulfonyl chloride.
などがある。and so on.
臭素化は、前述のごとく次亜臭素酸ナトリウノ・水溶液
をメチルフェニルスルホンの水懸濁液に滴下する方法の
ほかに、メチルフェニルスルホンとアルカリよりなる水
懸濁液中に、臭素を滴１・シて反応を行なわぜることも
Ｌ″ｉ’Ｊ能である。臭素を摘手する場合は、次亜臭素
酸塩の生成のために必要なアルカリ口を過剰に用いるこ
とはいうまでもない。Bromination can be carried out by dropping aqueous solution of sodium hypobromite into an aqueous suspension of methylphenylsulfone as described above, or by adding 1 drop of bromine into an aqueous suspension of methylphenylsulfone and an alkali. It is also possible to carry out the reaction by removing bromine.It goes without saying that when removing bromine, an excessive amount of alkali is used to produce hypobromite. .
いずれの場合にても得られる（トリブロモメチル）フェ
ニルスルホンは高純度であり、特に再結晶などの操作を
必要とはし７ない，−。The (tribromomethyl)phenyl sulfone obtained in either case is of high purity and does not require any particular operations such as recrystallization.
（実施例）
以下に本発明の方法を実施例をもって詐細に説明するが
、本発明は本実施例により何ら制約を受けるものではな
い。(Example) The method of the present invention will be explained in detail below using Examples, but the present invention is not limited in any way by the Examples.
実施例１
メチルフェニルスルホン４６．８ ｇ （０．３ ０モ
ル）。Example 1 Methylphenyl sulfone 46.8 g (0.30 mol).
９５％水酸化ナトリウム１２．６ｇ（０、３０モル）お
よび水３７０ｇよりなる混合液を６０’Ｃとした後、２
４ｗｔ％の次亜臭素酸ナトリウム水溶液４ ９ １ ｇ
（（、、）、９ ９モル）を同温度で３時間かけて滴
下した。さらに同温度で１時間撹拌した後、反応液を４
０℃に冷却し、結晶と１，て析出し７ている（トリブロ
モメチル）フェニルスルホンをか取１。A mixed solution consisting of 12.6 g (0.30 mol) of 95% sodium hydroxide and 370 g of water was heated to 60'C, and then heated to 2
4 wt% sodium hypobromite aqueous solution 491 g
((,,), 99 mol) was added dropwise over 3 hours at the same temperature. After further stirring at the same temperature for 1 hour, the reaction solution was
Cool to 0°C, and collect crystals and precipitated (tribromomethyl)phenyl sulfone.
た。得られた結晶を水洗後乾燥すると１ １． ３．
６ ｇ’（収率９６，４％）ｒｎｐ、１４６．３℃であ
った。Ta. When the obtained crystals are washed with water and dried, 11. 3.
6 g' (yield 96.4%) rnp, 146.3°C.
実施例２
メチルフェニルスルホン４６、８ｇ（０．３０モル）９
５％水酸化大トリウム１． ０４，２ ｇ （２．４７
５モル）および水６００ｇよりなる混合液を１００Ｃと
した。この液に臭素１５８ｇ（０．９９モル）を２時間
を要して滴］ミした後、反応液温を６０℃とし同温度で
３時間撹拌した。実施例１と同様に処理すると１１２．
８ｇ（収率９５．７％）の（トリブロモメチル）フェニ
ルスルホンが得られた。ｍ ｐ 。Example 2 Methylphenyl sulfone 46, 8 g (0.30 mol) 9
5% major thorium hydroxide 1. 04.2 g (2.47
A mixed solution consisting of 5 moles) and 600 g of water was set at 100C. After 158 g (0.99 mol) of bromine was added dropwise to this solution over a period of 2 hours, the temperature of the reaction solution was brought to 60° C., and the mixture was stirred at the same temperature for 3 hours. When processed in the same manner as in Example 1, 112.
8 g (yield 95.7%) of (tribromomethyl)phenylsulfone was obtained. m p.
］、４６．６°ｃ。], 46.6°c.
実施例３〜７
反応温度を表−１のごと（かえた以外は、実施例１と同
様に反応を行ない（トリブロモメチル）フェニルスルホ
ンを得た。結果を表−１に示す。Examples 3 to 7 The reaction was carried out in the same manner as in Example 1 except that the reaction temperature was changed as shown in Table 1 (tribromomethyl) phenyl sulfone was obtained. The results are shown in Table 1.
表
（発明の効果）
本発明においては、原料であるメチルフェニルスルホン
を臭素化し、（トリブロモメチル）フェニルスルホンを
得るに際し、メチルフェニルスルホンを溶解させるため
の有機溶媒を必要としない。Table (Effects of the Invention) In the present invention, when the raw material methylphenylsulfone is brominated to obtain (tribromomethyl)phenylsulfone, an organic solvent for dissolving the methylphenylsulfone is not required.
そのため臭素化剤として用いられる次亜臭素酸塩または
臭素は、有機溶媒との反応に消費されることなく全てメ
チルフェニルスルホンとの反応に用いられる。Therefore, the hypobromite or bromine used as a brominating agent is not consumed in the reaction with the organic solvent, but is entirely used in the reaction with methylphenylsulfone.
このことにより本発明には、
ｌ） 使用する臭素化剤は、原料のメチルフェニルスル
ホンに対しほぼ理論量でよい。Therefore, the present invention has the following advantages: l) The brominating agent used may be used in approximately the stoichiometric amount based on the raw material methylphenylsulfone.
２） 使用するアルカリ量は従来法に比べて１７１Ｏ以
下でよい。2) The amount of alkali used may be less than 171 O compared to the conventional method.
３） 副生物の生成がなく、再結晶などの煩雑な操作を
することなく高純度の製品を得ることができる。3) There is no generation of by-products, and high purity products can be obtained without complicated operations such as recrystallization.
４） 有機溶媒の回収操作が不要となる。4) No need for organic solvent recovery operation.
などの効果がみられ、工業的に実施するにあたり有利と
なる。The following effects can be seen, which is advantageous for industrial implementation.
Claims (5)
モメチル）フェニルスルホンを得るに際し、アルカリの
存在下、水を溶媒として用いることを特徴とする（トリ
ブロモメチル）フェニルスルホンの製造法。(1) A method for producing (tribromomethyl) phenyl sulfone, which comprises using water as a solvent in the presence of an alkali when brominating methyl phenyl sulfone to obtain (tribromomethyl) phenyl sulfone.
とする請求項（１）記載の方法。(2) The method according to claim (1), characterized in that the bromination is carried out using hypobromite.
求項（２）記載の方法。(3) The method according to claim (2), wherein the hypobromite is sodium hypobromite.
項（１）記載の方法。(4) The method according to claim (1), wherein the bromination is carried out at a temperature range of 30 to 100°C.
（１）記載の方法。(5) The method according to claim (1), wherein the alkali is an alkali metal hydroxide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1088359A JPH0670001B2 (en) | 1989-04-06 | 1989-04-06 | Method for producing (tribromomethyl) phenyl sulfone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1088359A JPH0670001B2 (en) | 1989-04-06 | 1989-04-06 | Method for producing (tribromomethyl) phenyl sulfone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02264754A true JPH02264754A (en) | 1990-10-29 |
| JPH0670001B2 JPH0670001B2 (en) | 1994-09-07 |
Family
ID=13940616
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1088359A Expired - Lifetime JPH0670001B2 (en) | 1989-04-06 | 1989-04-06 | Method for producing (tribromomethyl) phenyl sulfone |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0670001B2 (en) |
-
1989
- 1989-04-06 JP JP1088359A patent/JPH0670001B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0670001B2 (en) | 1994-09-07 |
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