JPH09227499A - Sulfonation of phenols - Google Patents
Sulfonation of phenolsInfo
- Publication number
- JPH09227499A JPH09227499A JP3597096A JP3597096A JPH09227499A JP H09227499 A JPH09227499 A JP H09227499A JP 3597096 A JP3597096 A JP 3597096A JP 3597096 A JP3597096 A JP 3597096A JP H09227499 A JPH09227499 A JP H09227499A
- Authority
- JP
- Japan
- Prior art keywords
- sulfonation
- phenols
- butyl
- solvent
- sulfonating agent
- 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
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、ニトロ系溶媒を使用せ
ずに、フェノ−ル類のスルホン化物を製造する方法に関
する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for producing a sulfonated phenol compound without using a nitro solvent.
【０００２】[0002]
【従来の技術】スルホン化されたフェノ−ル類はスルホ
ン基をいれることによって水溶性をなすことが出来るの
で、染料あるいは医薬の中間体、写真薬品およびその中
間体として広く使用されている。2. Description of the Related Art Sulfonated phenols can be made water-soluble by incorporating a sulfone group, and are therefore widely used as intermediates for dyes or pharmaceuticals, photographic chemicals and their intermediates.
【０００３】フェノ−ル類は硫酸、発煙硫酸、クロロス
ルホン酸、亜硫酸ガス、ジアルキル硫酸等で容易にスル
ホン化されることが知られている。古くは、スルホン化
物の着色を低減する為、米国特許2487,586(1949)にはニ
トロベンゼン中でレゾルシンをクロロスルホン酸を用い
てスルホン化することが記載されているが、ニトロベン
ゼンという特殊な溶剤(硝酸繊維素)しか使用されていな
い。It is known that phenols are easily sulfonated with sulfuric acid, fuming sulfuric acid, chlorosulfonic acid, sulfurous acid gas, dialkyl sulfuric acid and the like. In the past, in order to reduce the coloration of sulfonates, U.S. Pat. Only fibrin nitrate) is used.
【０００４】また、独国特許820,659(1959) には、亜硫
酸ガスでスルホン化することが記載されているが、スル
ホン化の制御が困難なことと大がかりな排ガス対策設備
が必要である。Further, German Patent 820,659 (1959) describes sulfonation with sulfurous acid gas, but it is difficult to control sulfonation and a large-scale exhaust gas countermeasure facility is required.
【０００５】また、近年では硫酸水溶液でスルホン化す
る方法 (Collect.Czech.Chem.Commun.32(8),3004-23(19
67))、濃硫酸やニトロメタン溶媒中で亜硫酸ガスを使用
してスルホン化する方法(Recl.Trav.Chim.Pays-Bas 107
(9),543-548(1988) Recl.Trav.Chim.Pays-Bas 108,7-1
3(1989))等の技術的な研究がされているが、いずれの方
法もモノスルホン化、ジスルホン化、トリスルホン化を
選択的に制御するのが困難である。In recent years, a method of sulfonating with an aqueous solution of sulfuric acid (Collect.Czech.Chem.Commun. 32 (8), 3004-23 (19
67)), sulfonation using sulfurous acid gas in concentrated sulfuric acid or nitromethane solvent (Recl. Trav. Chim. Pays-Bas 107
(9), 543-548 (1988) Recl.Trav.Chim.Pays-Bas 108,7-1
3 (1989)) and the like, but it is difficult to selectively control monosulfonation, disulfonation or trisulfonation by any of the methods.
【０００６】特に、亜硫酸ガスを使用する場合、自己分
解性の危険があるニトロメタン溶媒を使用しているばか
りでなく、スルホン化の選択性が低い上に置換基として
水酸基が入っていると水酸基とも反応してしまう欠点が
ある。[0006] In particular, when sulfurous acid gas is used, not only is a nitromethane solvent that has a risk of self-decomposing property used, but also when sulfonation selectivity is low and a hydroxyl group is contained as a substituent, both It has the drawback of reacting.
【０００７】また、その他のスルホン化溶媒としてエ−
テル類が知られているが、エチルエ−テルの様なアルキ
ルエ−テル類では爆発の危険性が高く、ジオキサンの様
な環状エ−テル類では有害性が高いので工業的には好ま
しくない。Further, as another sulfonation solvent,
Tereth are known, but alkyl ethers such as ethyl ether have a high risk of explosion, and cyclic ethers such as dioxane are highly harmful, which is not industrially preferable.
【０００８】[0008]
【発明が解決しようとする課題】安全で着色が無くかつ
不純物の副生が少なく選択的にスルホン化する工業的な
製造法の開発が強く望まれている。従って本発明の目的
は、高価で爆発の危険性があるニトロ系溶媒、また、爆
発の危険性の高いエ−テル類、有害性の高いジオキサン
類の溶媒を使用する事なく、フェノ−ル類のスルホン化
を選択的かつ定量的に行う方法を提供することにある。There is a strong demand for the development of an industrial production method which is safe, has no coloration, has little by-product of impurities, and is selectively sulfonated. Therefore, an object of the present invention is to use a nitro solvent which is expensive and has a risk of explosion, an ether having a high risk of explosion, and a solvent of dioxane having a high toxicity, and a phenol compound. Another object of the present invention is to provide a method for selectively and quantitatively performing sulfonation of benzene.
【０００９】[0009]
【課題が解決しようとする手段】本発明の上記目的は、
フェノ−ル類をスルホン化剤によりスルホン化する反応
において、炭酸ジアルキル溶媒を用いることを特徴とす
る、フェノ−ル類のスルホン化を行う方法により達成さ
れた。The above objects of the present invention are as follows.
In a reaction for sulfonating phenols with a sulfonating agent, it was achieved by a method for sulfonating phenols, which is characterized by using a dialkyl carbonate solvent.
【００１０】以下、本発明を更に詳細に説明する。本発
明に用いられるフェノ−ル類とは、一般式(１)で表され
る化合物である。Hereinafter, the present invention will be described in more detail. The phenols used in the present invention are compounds represented by the general formula (1).
【化１】 式中、Ｒ1、R2は水素原子、メチル、エチル、n-プロピ
ル、イソプロピル、n-ブチル、 iso-ブチル、sec-ブチ
ル、tert-ブチルなどの炭素数１〜１０のアルキル基を
示し、それぞれ同一または異なった基でも良い。Embedded image In the formula, R 1 and R 2 represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms such as methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, They may be the same or different groups.
【００１１】本発明に用いられる硫酸系、亜硫酸系スル
ホン化剤としては硫酸、発煙硫酸、クロロスルホン酸、
ジアルキル硫酸等が好ましく、特にクロロスルホン酸が
好ましい。Sulfuric acid-based and sulfite-based sulfonating agents used in the present invention include sulfuric acid, fuming sulfuric acid, chlorosulfonic acid,
Dialkyl sulfuric acid and the like are preferable, and chlorosulfonic acid is particularly preferable.
【００１２】本発明に用いられる炭酸ジアルキル溶媒と
は、一般式(２)で表される化合物であるThe dialkyl carbonate solvent used in the present invention is a compound represented by the general formula (2).
【化２】 式中、Ｒ1、R2はメチル、エチル、n-プロピル、イソプロ
ピル、n-ブチル、iso-ブチル、sec-ブチル、tert-ブチ
ルなどの炭素数１〜４の低級アルキル基を示し、それぞ
れ同一または異なった基でも良い。Embedded image In the formula, R 1 and R 2 represent a lower alkyl group having 1 to 4 carbon atoms such as methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, tert-butyl and the like, and are the same. Or different groups may be used.
【００１３】本発明に用いられる溶媒の使用量は、フェ
ノ−ル類に対しては重量で１〜１００倍で有ることが好
ましく、更に好ましくは２〜２０倍である。反応温度に
ついては特に制限は無いが、温度が低すぎると反応が遅
くなり、高すぎると反応の選択性が落ちるばかりでな
く、分解反応が進行することから、−２０℃〜９０℃
（沸点）が好ましく、更にこのましくは−１０〜２０℃
である。The amount of the solvent used in the present invention is preferably 1 to 100 times, and more preferably 2 to 20 times, the weight of the phenols. The reaction temperature is not particularly limited, but if the temperature is too low, the reaction becomes slow, and if it is too high, not only the selectivity of the reaction decreases but also the decomposition reaction proceeds, so that the reaction temperature is -20 ° C to 90 ° C.
(Boiling point) is preferable, and more preferably -10 to 20 ° C.
It is.
【００１４】本発明において硫酸系、亜硫酸系スルホン
化剤の使用量は目的とする生成物と異なるが、例えば、
モノスルホン体を得る場合には、クロロ硫酸のようなハ
ロゲン硫酸を使用すると、原料１モルに対して０．５〜
１．５モル使用するのが好ましく、更に好ましくは０．
８〜１．２モルである。また、ジスルホン体を得る場合
には原料１モルに対して１．５モル以上使用されること
が好ましく、更に好ましくは１．８〜２．５モルであ
る。In the present invention, the amount of the sulfuric acid-based and sulfite-based sulfonating agents used is different from that of the intended product.
In the case of obtaining a monosulfone compound, when halogenated sulfuric acid such as chlorosulfuric acid is used, 0.5 to 0.5 mol per mol of the raw material
It is preferably used in an amount of 1.5 mol, more preferably 0.1.
It is 8 to 1.2 mol. Further, when a disulfone compound is obtained, it is preferably used in an amount of 1.5 mol or more, more preferably 1.8 to 2.5 mol, based on 1 mol of the raw material.
【００１５】[0015]
【実施例】以下に実施例を挙げて本発明をさらに詳しく
説明するが、本発明はこれらに限定されるものではな
い。 実施例１ レゾルシノール（６６．０ｇ、０．６ｍｏｌ）を炭酸ジ
メチル３００ｍＬに溶解させ、５℃以下で撹拌しなが
ら、あらかじめ用意したクロロスルホン酸（７３．４
ｇ）と炭酸ジメチル（１６８ｍＬ）の混合液をゆっくり
と滴下した。滴下終了後さらに２時間 撹拌した。核磁
気共鳴装置で求められた転化率９９％で４位にスルホン
基が選択的に入る(δ値:６.５ppm)。EXAMPLES The present invention will be described in more detail with reference to the following Examples, but it should not be construed that the present invention is limited thereto. Example 1 Resorcinol (66.0 g, 0.6 mol) was dissolved in 300 mL of dimethyl carbonate and stirred at 5 ° C. or lower while being prepared in advance with chlorosulfonic acid (73.4).
A mixture of g) and dimethyl carbonate (168 mL) was slowly added dropwise. After the completion of dropping, the mixture was stirred for another 2 hours. At a conversion of 99% determined by a nuclear magnetic resonance apparatus, a sulfone group selectively enters the 4-position (δ value: 6.5 ppm).
【００１６】実施例２ カテコ−ル（６６．０ｇ、０．６ｍｏｌ）を炭酸ジメチ
ル３００ｍＬに溶解させ、５℃以下で撹拌しながら、あ
らかじめ用意したクロロスルホン酸（７３．４ｇ）と炭
酸ジメチル（１６８ｍＬ）の混合液をゆっくりと滴下し
た。滴下終了後さらに２時間 撹拌した。核磁気共鳴装
置で求められた転化率９７％で４位にスルホン基が選択
的に入る(δ値:６.８ppm)。Example 2 Catechol (66.0 g, 0.6 mol) was dissolved in 300 mL of dimethyl carbonate, and chlorosulfonic acid (73.4 g) and dimethyl carbonate (168 mL) prepared in advance were stirred with stirring at 5 ° C or lower. ) Was slowly added dropwise. After the completion of dropping, the mixture was stirred for another 2 hours. With a conversion of 97% determined by a nuclear magnetic resonance apparatus, a sulfone group selectively enters the 4-position (δ value: 6.8 ppm).
【００１７】実施例３ ヒドロキノン（６６．０ｇ、０．６ｍｏｌ）を炭酸ジメ
チル３００ｍＬに溶解させ、５℃以下で撹拌しながら、
あらかじめ用意したクロロスルホン酸（７３．４ｇ）と
炭酸ジメチル（１６８ｍＬ）の混合液をゆっくりと滴下
した。滴下終了後さらに２時間 撹拌した。核磁気共鳴
装置で求められた転化率９８％で２位にスルホン基が選
択的に入る(δ値:７.３ppm)。Example 3 Hydroquinone (66.0 g, 0.6 mol) was dissolved in 300 mL of dimethyl carbonate and stirred at 5 ° C. or lower while stirring.
A mixed liquid of chlorosulfonic acid (73.4 g) and dimethyl carbonate (168 mL) prepared in advance was slowly added dropwise. After the completion of dropping, the mixture was stirred for another 2 hours. The sulfone group selectively enters the 2-position at a conversion of 98% determined by a nuclear magnetic resonance apparatus (δ value: 7.3 ppm).
【００１８】実施例４ レゾルシノール（６６．０ｇ、０．６ｍｏｌ）を炭酸ジ
エチル３３０ｍＬに溶解させ、５℃以下で撹拌しなが
ら、あらかじめ用意したクロロスルホン酸（７３．４
ｇ）と炭酸ジエチル（１７０ｍＬ）の混合液をゆっくり
と滴下した。滴下終了後さらに２時間 撹拌した。核磁
気共鳴装置で求められた転化率９９％で４位にスルホン
基が選択的に入る(δ値:６.５ppm)。Example 4 Resorcinol (66.0 g, 0.6 mol) was dissolved in 330 mL of diethyl carbonate and stirred at 5 ° C. or lower with stirring to prepare chlorosulfonic acid (73.4).
A mixture of g) and diethyl carbonate (170 mL) was slowly added dropwise. After the completion of dropping, the mixture was stirred for another 2 hours. At a conversion of 99% determined by a nuclear magnetic resonance apparatus, a sulfone group selectively enters the 4-position (δ value: 6.5 ppm).
【００１９】実施例５ ３−メトキシフェノ−ル（７４．４ｇ、０．６ｍｏｌ）
を炭酸ジメチル３００ｍＬに溶解させ、５℃以下で撹拌
しながら、あらかじめ用意したクロロスルホン酸（７
３．４ｇ）と炭酸ジメチル（１６８ｍＬ）の混合液をゆ
っくりと滴下した。滴下終了後さらに２時間 撹拌し
た。核磁気共鳴装置で求められた転化率９９％で４位に
スルホン基が選択的に入る(δ値:６.５ppm)。Example 5 3-Methoxyphenol (74.4 g, 0.6 mol)
Was dissolved in 300 mL of dimethyl carbonate, and the chlorosulfonic acid (7
A mixture of 3.4 g) and dimethyl carbonate (168 mL) was slowly added dropwise. After the completion of dropping, the mixture was stirred for another 2 hours. At a conversion of 99% determined by a nuclear magnetic resonance apparatus, a sulfone group selectively enters the 4-position (δ value: 6.5 ppm).
【００２０】実施例６ ２−メトキシフェノ−ル（７４．４ｇ、０．６ｍｏｌ）
を炭酸ジメチル３００ｍＬに溶解させ、５℃以下で撹拌
しながら、あらかじめ用意したクロロスルホン酸（７
３．４ｇ）と炭酸ジメチル（１６８ｍＬ）の混合液をゆ
っくりと滴下した。滴下終了後さらに２時間 撹拌し
た。核磁気共鳴装置で求められた転化率９７％で４位に
スルホン基が選択的に入る(δ値:６.９ppm)。Example 6 2-Methoxyphenol (74.4 g, 0.6 mol)
Was dissolved in 300 mL of dimethyl carbonate, and the chlorosulfonic acid (7
A mixture of 3.4 g) and dimethyl carbonate (168 mL) was slowly added dropwise. After the completion of dropping, the mixture was stirred for another 2 hours. At a conversion of 97% determined by a nuclear magnetic resonance apparatus, a sulfone group selectively enters the 4-position (δ value: 6.9 ppm).
───────────────────────────────────────────────────── フロントページの続き (72)発明者 下崎 隆司 静岡県磐田郡浅羽町大野6909−９ 株式会 社コニカケミカル内 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Takashi Shimozaki 6909-9 Ono, Asaba-cho, Iwata-gun, Shizuoka Konica Chemical Co., Ltd.
Claims (7)
ホン化する反応にあたり、炭酸ジアルキル溶媒中で反応
させることを特徴とする、フェノ−ル類のスルホン化方
法。1. A method for sulfonation of phenols, which comprises reacting the phenols with a sulfonating agent in a dialkyl carbonate solvent.
ル類、レゾルシン類、ヒドロキノン類のフェノ−ル類化
合物から選ばれる少なくとも１種をスルホン化剤により
スルホン化する反応において、炭酸ジアルキル溶媒を用
いることを特徴とする、フェノ−ル類のスルホン化方
法。2. The phenols are phenols and catechols.
In the reaction of sulfonation of at least one selected from phenols such as phenols, resorcins and hydroquinones with a sulfonating agent, a dialkyl carbonate solvent is used. .
n-プロピル、イソプロピル、n-ブチル、iso-ブチル、se
c-ブチル、 tert-ブチルなどの炭素数１〜４の低級アル
キル基の炭酸ジアルキル溶媒である請求項１記載のスル
ホン化方法。3. The dialkyl carbonate solvent is methyl, ethyl,
n-propyl, isopropyl, n-butyl, iso-butyl, se
The sulfonation method according to claim 1, which is a dialkyl carbonate solvent having a lower alkyl group having 1 to 4 carbon atoms, such as c-butyl and tert-butyl.
請求項１記載のスルホン化方法。4. The sulfonation method according to claim 1, wherein the sulfonating agent is a sulfuric acid type or a sulfite type.
ル、レゾルシンである請求項２記載のスルホン化方法。5. The phenols are phenol and catechol.
The sulfonation method according to claim 2, wherein the sulfonation is resorcinol.
酸ジエチルまたは、炭酸ジイソプロピルから選ばれる１
種または２種以上の溶媒である請求項１記載のフェノ−
ル類のスルホン化方法。6. The dialkyl carbonate solvent is selected from dimethyl carbonate, diethyl carbonate or diisopropyl carbonate.
The pheno according to claim 1, which is one kind or two or more kinds of solvents.
Method for sulfonation of resins.
請求項１記載のスルホン化方法。7. The sulfonation method according to claim 1, wherein the sulfonating agent is chlorosulfonic acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3597096A JPH09227499A (en) | 1996-02-23 | 1996-02-23 | Sulfonation of phenols |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3597096A JPH09227499A (en) | 1996-02-23 | 1996-02-23 | Sulfonation of phenols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH09227499A true JPH09227499A (en) | 1997-09-02 |
Family
ID=12456790
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3597096A Pending JPH09227499A (en) | 1996-02-23 | 1996-02-23 | Sulfonation of phenols |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH09227499A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2791057A1 (en) * | 1999-03-17 | 2000-09-22 | 3V Sigma Spa | Benzophenone sulfonic acids preparation, useful as sunscreens against UV- A and UV-B, comprises reacting non-sulfonated benzophenone with chlorosulfonic acid in dialkylcarbonate solvent medium |
| US6936732B2 (en) | 2001-09-22 | 2005-08-30 | Jonathan Simon Hill | Sulphonation of phenols |
| CN102796029A (en) * | 2011-05-23 | 2012-11-28 | 辽宁石油化工大学 | Clean synthesis process for cosmetic grade 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid |
| JP2019516781A (en) * | 2016-04-07 | 2019-06-20 | ツェーエムブルー プロイェクト アーゲー | Sulfonated aromatic compounds |
| US11450854B2 (en) | 2017-02-13 | 2022-09-20 | Cmblu Energy Ag | Redox flow battery electrolytes |
| US11788228B2 (en) | 2017-02-13 | 2023-10-17 | Cmblu Energy Ag | Methods for processing lignocellulosic material |
| US11831017B2 (en) | 2018-02-13 | 2023-11-28 | Cmblu Energy Ag | Redox flow battery electrolytes |
| US11891349B2 (en) | 2018-02-13 | 2024-02-06 | Cmblu Energy Ag | Aminated lignin-derived compounds and uses thereof |
-
1996
- 1996-02-23 JP JP3597096A patent/JPH09227499A/en active Pending
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2791057A1 (en) * | 1999-03-17 | 2000-09-22 | 3V Sigma Spa | Benzophenone sulfonic acids preparation, useful as sunscreens against UV- A and UV-B, comprises reacting non-sulfonated benzophenone with chlorosulfonic acid in dialkylcarbonate solvent medium |
| US6936732B2 (en) | 2001-09-22 | 2005-08-30 | Jonathan Simon Hill | Sulphonation of phenols |
| CN102796029A (en) * | 2011-05-23 | 2012-11-28 | 辽宁石油化工大学 | Clean synthesis process for cosmetic grade 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid |
| JP2019516781A (en) * | 2016-04-07 | 2019-06-20 | ツェーエムブルー プロイェクト アーゲー | Sulfonated aromatic compounds |
| US11008284B2 (en) | 2016-04-07 | 2021-05-18 | Cmblu Projekt Ag | Sulfonated aromatic compounds |
| JP2022000431A (en) * | 2016-04-07 | 2022-01-04 | ツェーエムブルー プロイェクト アーゲー | Sulfonated aromatic compounds |
| US11225756B2 (en) | 2016-04-07 | 2022-01-18 | Cmblu Projekt Ag | Method for producing low molecular weight aromatic lignin-derived compounds |
| US11773537B2 (en) | 2016-04-07 | 2023-10-03 | Cmblu Energy Ag | Sulfonated lignin-derived compounds and uses thereof |
| US11450854B2 (en) | 2017-02-13 | 2022-09-20 | Cmblu Energy Ag | Redox flow battery electrolytes |
| US11788228B2 (en) | 2017-02-13 | 2023-10-17 | Cmblu Energy Ag | Methods for processing lignocellulosic material |
| US11831017B2 (en) | 2018-02-13 | 2023-11-28 | Cmblu Energy Ag | Redox flow battery electrolytes |
| US11891349B2 (en) | 2018-02-13 | 2024-02-06 | Cmblu Energy Ag | Aminated lignin-derived compounds and uses thereof |
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