JPH06145091A - Production of aromatic ether compound - Google Patents
Production of aromatic ether compoundInfo
- Publication number
- JPH06145091A JPH06145091A JP4294917A JP29491792A JPH06145091A JP H06145091 A JPH06145091 A JP H06145091A JP 4294917 A JP4294917 A JP 4294917A JP 29491792 A JP29491792 A JP 29491792A JP H06145091 A JPH06145091 A JP H06145091A
- Authority
- JP
- Japan
- Prior art keywords
- solvent
- aromatic ether
- ether compound
- compound
- mol
- 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
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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
【０００１】[0001]
【産業上の利用分野】本発明は、芳香族エ−テル化合物
の製造に関するものである。FIELD OF THE INVENTION The present invention relates to the production of aromatic ether compounds.
【０００２】[0002]
【従来の技術】一般に芳香族水酸化物は融点が高く、炭
酸アルキルエステルはそれに比べて沸点が低いという特
徴がある。また、芳香族水酸化物は炭酸アルキルエステ
ルには溶解しにくい。これらのことにより、目的とする
芳香族エ−テル化合物は上記に示した原料で製造する
時、反応は必然的に加圧条件となる。反応条件が加圧と
なると、固定費や比例費が増加する。2. Description of the Related Art Generally, aromatic hydroxides have a high melting point and carbonic acid alkyl esters have a lower boiling point. In addition, aromatic hydroxide is difficult to dissolve in alkyl carbonate ester. Due to these facts, when the target aromatic ether compound is produced from the above-mentioned raw materials, the reaction is necessarily a pressurized condition. When the reaction condition is pressurized, fixed cost and proportional cost increase.
【０００３】また、従来より反応において溶媒を使用す
るという概念はあったが、上述の条件における芳香族エ
−テル化合物の製造においては詳細には検討されていな
い。溶媒としてジオキサンを使用している実施例（特公
昭６１−４３３３４）もあるが、触媒があまり有効でな
いため反応速度が遅い（比較例２にて補足説明）。ま
た、反応速度を早くするため塩基性の強い触媒を使用す
ると、溶媒が分解したり、副反応が起こりやすくなる可
能性がある。（比較例３にて補足説明）。Although there has been the concept of using a solvent in the reaction, it has not been studied in detail in the production of aromatic ether compounds under the above-mentioned conditions. There is also an example (Japanese Patent Publication No. Sho 61-43334) using dioxane as a solvent, but the reaction rate is slow because the catalyst is not very effective (supplementary explanation in Comparative Example 2). Further, if a catalyst having a strong basicity is used to accelerate the reaction rate, the solvent may be decomposed or side reactions may easily occur. (Supplementary explanation in Comparative Example 3).
【０００４】[0004]
【発明が解決しようとする課題】本発明の目的は、前述
の問題点を解決し、加圧操作を必要とせずに効率よく芳
香族エ−テル化合物を製造する方法を提供することであ
る。SUMMARY OF THE INVENTION An object of the present invention is to solve the above-mentioned problems and to provide a method for efficiently producing an aromatic ether compound without requiring a pressurizing operation.
【０００５】[0005]
【課題を解決するための手段】即ち、本発明はアルカリ
性触媒の存在下で、フェノ−ル類を炭酸アルキルエステ
ルと反応させる芳香族エ−テル化合物の製造方法におい
て、含窒素複素環式化合物又はアミド結合を持つ化合物
を溶媒として用いることを特徴とする芳香族エ−テル化
合物の製造方法である。That is, the present invention provides a method for producing an aromatic ether compound in which a phenol is reacted with a carbonic acid alkyl ester in the presence of an alkaline catalyst. A method for producing an aromatic ether compound, which comprises using a compound having an amide bond as a solvent.
【０００６】アルカリ性触媒とは例えばＮａＯＨ、ＫＯ
Ｈ、Ｃａ（ＯＨ）２、Ｋ２ＣＯ３、ＭｇＣＯ３等であ
り、また、ＮａＯＣＨ３やＮａＯＣ２Ｈ５のような有機
物との塩であってもよい。また、アンバ−リストのよう
なイオン交換樹脂を触媒として使用することもできる。The alkaline catalyst is, for example, NaOH or KO.
H, a Ca (OH) 2, K 2 CO 3, MgCO 3 , etc., may also be a salt with an organic, such as NaOCH 3 and NaOC 2 H 5. Also, an ion exchange resin such as Amberlyst can be used as a catalyst.
【０００７】フェノ−ル類とは例えばフェノ−ルであり
カテコ−ル、ハイドロキノンのような多価フェノ−ルで
あり、グアイアコ−ル、ｐ−クロロフェノ−ルのような
置換フェノ−ルであり、メチルハイドロキノンのような
置換多価フェノ−ルである。置換基について特に制限は
ない。The phenols are, for example, phenol and polyvalent phenols such as catechol and hydroquinone, and substituted phenols such as guaiacol and p-chlorophenol. It is a substituted polyphenol such as methylhydroquinone. There is no particular limitation on the substituent.
【０００８】特に、本発明より前述した問題点が解決さ
れるようなものとしては、融点の高いものがより効果が
期待される。In particular, the one having a high melting point is expected to be more effective as a solution to the above-mentioned problems according to the present invention.
【０００９】炭酸アルキルエステルとは、例えばジメチ
ルカ−ボネ−トやジエチルカ−ボネ−ト等であり、これ
らは目的とするエ−テル化合物の構造によって選択され
る。溶媒としてはピリジン、ピコリン、キノリン等のピ
リジン及びピリジン誘導体や、Ｎ，Ｎ−ジメチルホルム
アミド、Ｎ，Ｎ−ジエチルホルムアミド等のホルムアミ
ド化合物、Ｎ，Ｎ−ジメチルアセトアミド等のアセトア
ミド化合物等が好ましい。また、Ｎ−メチル−２−ピロ
リドン等も使用できる。これらは常温で液体であるもの
がより好ましい。The carbonic acid alkyl ester is, for example, dimethyl carbonate or diethyl carbonate, and these are selected depending on the structure of the target ether compound. As the solvent, pyridine and pyridine derivatives such as pyridine, picoline and quinoline, formamide compounds such as N, N-dimethylformamide and N, N-diethylformamide, acetamide compounds such as N, N-dimethylacetamide and the like are preferable. Further, N-methyl-2-pyrrolidone or the like can also be used. It is more preferable that these are liquids at room temperature.
【００１０】フェノ−ル類は炭酸アルキルエステルと、
当量又は過剰もしくは不足量で反応させることができ
る。好ましい割合は、フェノ−ル類１モルに対し炭酸ジ
アルキルエステル０．１〜１０モルである。また触媒の
量は、一般にフェノ−ル類１モルに対し、０．０００１
〜１０モルであり、０．００１〜０．０１モルが好まし
い。The phenols are carbonic acid alkyl esters,
It is possible to react in an equivalent amount or an excess amount or an insufficient amount. The preferred ratio is 0.1 to 10 mol of carbonic acid dialkyl ester with respect to 1 mol of phenols. The amount of the catalyst is generally 0.0001 with respect to 1 mol of the phenols.
10 to 10 mol, preferably 0.001 to 0.01 mol.
【００１１】溶媒量は、原料のフェノ−ル数１０ｇに対
し１ｇ〜１００００ｇが好ましい。原料及び触媒は溶媒
に溶解することが好ましいが、必ずしも全部が溶解して
いる必要はない。The amount of the solvent is preferably 1 g to 10000 g per 10 g of the raw material phenol. The raw material and the catalyst are preferably dissolved in the solvent, but it is not always necessary that all are dissolved.
【００１２】反応温度は、溶媒の種類によっては適宜選
択されるが、一般に１００〜３００℃で、溶媒の沸点以
下でも可能であるが、副生するアルコ−ルを遂次抜き取
ることにより反応が促進される（特開昭６２−２４６５
３３）ので、そのために溶媒の沸点で反応させるのが好
ましい。アルコ−ルを抜き取る方法は特に限定されるも
のではないが、蒸留や吸着、膜分離等が好ましく使用で
きる。The reaction temperature is appropriately selected depending on the kind of the solvent, but it is generally 100 to 300 ° C., and it is possible to be lower than the boiling point of the solvent, but the reaction is promoted by successively extracting the by-produced alcohol. (Japanese Patent Laid-Open No. 62-2465)
33), and therefore it is preferable to react at the boiling point of the solvent. The method for extracting the alcohol is not particularly limited, but distillation, adsorption, membrane separation and the like can be preferably used.
【００１３】以下に実施例を示し、さらに詳しく本発明
を説明する。The present invention will be described in more detail with reference to the following examples.
【００１４】[0014]
【比較例１】ソックスレ−抽出器を装置として用いる。Comparative Example 1 A Soxhlet extractor is used as a device.
【００１５】３００ｍｌの４口丸底フラスコにハイドロ
キノン（ＨＱ）を１１．０ｇ（０．１ｍｏｌ）、ジメチ
ルカ−ボネ−トを１８．００ｇ（０．２ｍｏｌ）、炭酸
カリウムを０．６９ｇ（５ｍｍｏｌ）を仕込む。溶媒は
使用しない。反応により副生したメタノ−ルを除去する
ため充填部にモレキュラ−シ−ブ（ＭＳ−４Ａ）を３
０．０ｇ充填する。オイルバスで加熱し、オイル温度１
２０〜１５０℃、リフラックス状態で反応させる。８時
間後のＨＱ転化率は０％であった。In a 300 ml 4-neck round bottom flask, 11.0 g (0.1 mol) of hydroquinone (HQ), 18.00 g (0.2 mol) of dimethyl carbonate and 0.69 g (5 mmol) of potassium carbonate were added. Prepare. No solvent is used. Molecular sieve (MS-4A) was added to the packing part to remove methanol by-produced by the reaction.
Fill with 0.0 g. Heat in oil bath, oil temperature 1
The reaction is carried out in a reflux state at 20 to 150 ° C. The HQ conversion rate after 8 hours was 0%.
【００１６】[0016]
【比較例２】ソックスレ−抽出器を装置として用いる。Comparative Example 2 A Soxhlet extractor is used as a device.
【００１７】３００ｍｌの４口丸底フラスコにＨＱを１
１．０ｇ（０．１ｍｏｌ）、ジメチルカ−ボネ−トを１
８．００ｇ（０．２ｍｏｌ）、溶媒かつ触媒としてピリ
ジンを１００ｍｌ仕込む。充填部にモレキュラ−シ−ブ
（ＭＳ−４Ａ）を３０．０ｇ充填する。オイルバスで加
熱し、オイル温度１７０〜２００℃、リフラックス状態
で反応させる。５２０分後のＨＱ転化率は２９％、ハイ
ドロキノンモノメチルエ−テル（ＭＱ）の選択率１００
％であった。Add 1 HQ to a 300 ml 4-neck round bottom flask.
1.0 g (0.1 mol) of dimethyl carbonate
Charge 8.00 g (0.2 mol) and 100 ml of pyridine as a solvent and a catalyst. 30.0 g of molecular sieve (MS-4A) is charged in the filling part. The mixture is heated in an oil bath and reacted at an oil temperature of 170 to 200 ° C in a reflux state. After 520 minutes, the HQ conversion was 29%, and the hydroquinone monomethyl ether (MQ) selectivity was 100.
%Met.
【００１８】[0018]
【実施例１】ソックスレ−抽出器を装置として用いる。Example 1 A Soxhlet extractor is used as a device.
【００１９】３００ｍｌの４口丸底フラスコにＨＱを１
１．０ｇ（０．１ｍｏｌ）、ジメチルカ−ボネ−トを１
８．００ｇ（０．２ｍｏｌ）、炭酸カリウムを０．６９
ｇ（５ｍｍｏｌ）、溶媒としてピリジンを１００ｍｌ仕
込む。充填部にモレキュラ−シ−ブ（ＭＳ−４Ａ）を３
０．０ｇ充填する。オイルバスで加熱し、オイル温度１
７０〜２００℃、リフラックス状態で反応させる。１７
０分後のＨＱ転化率１５％、ＭＱの選択率１００％であ
り、５２０分後のＨＱ転化率４８％、ＭＱの選択率９８
％、ハイドロキノンジメチルエ−テル（ＨＱＤＭＥ）の
選択率２％であった。Add 1 HQ to a 300 ml 4-neck round bottom flask.
1.0 g (0.1 mol) of dimethyl carbonate
8.00 g (0.2 mol), 0.69 potassium carbonate
g (5 mmol) and 100 ml of pyridine as a solvent are charged. 3 molecular sieves (MS-4A) in the filling part
Fill with 0.0 g. Heat in oil bath, oil temperature 1
The reaction is performed at 70 to 200 ° C. in a reflux state. 17
The HQ conversion rate after 0 minutes was 15%, the MQ selectivity was 100%, and the HQ conversion rate after 520 minutes was 48% and the MQ selectivity was 98.
%, And the selectivity of hydroquinone dimethyl ether (HQDME) was 2%.
【００２０】[0020]
【比較例３】ソックスレ−抽出器を装置として用いる。Comparative Example 3 A Soxhlet extractor is used as a device.
【００２１】３００ｍｌの４口丸底フラスコにハイドロ
キノン（ＨＱ）を１１．０ｇ（０．１ｍｏｌ）、ジメチ
ルカ−ボネ−トを１８．００ｇ（０．２ｍｏｌ）、炭酸
カリウムを０．６９ｇ（５ｍｍｏｌ）、溶媒としてシク
ロヘキサノンを１００ｍｏｌ仕込む。充填部にモレキュ
ラ−シ−ブ（ＭＳ−４Ａ）を３０．０ｇ充填する。オイ
ルバスで加熱し、オイル温度１７０〜２００℃、リフラ
ックス状態で反応させる。４９０分後のＨＱ転化率６０
％、ハイドロキノンモノメチルエ−テル（ＭＱ）の選択
率７３％、ハイドロキノンジメチルエ−テル（ＨＱＤＭ
Ｅ）の選択率２７％であったが、ガスクロマトグラフィ
−分析において、シクロヘキサノンに由来する生成物を
含む上記物質以外（原料、溶媒、生成物以外）の不純物
がピ−ク面積百分率で約１５％含まれることを確認し
た。In a 300 ml four-neck round bottom flask, 11.0 g (0.1 mol) of hydroquinone (HQ), 18.00 g (0.2 mol) of dimethyl carbonate and 0.69 g (5 mmol) of potassium carbonate were added. 100 mol of cyclohexanone is charged as a solvent. 30.0 g of molecular sieve (MS-4A) is charged in the filling part. The mixture is heated in an oil bath and reacted at an oil temperature of 170 to 200 ° C in a reflux state. HQ conversion 60 after 490 minutes
%, Hydroquinone monomethyl ether (MQ) selectivity 73%, hydroquinone dimethyl ether (HQDM)
Although the selectivity of E) was 27%, gas chromatography analysis revealed that impurities other than the above substances (other than raw materials, solvents and products) including products derived from cyclohexanone were about 15% in terms of peak area percentage. Confirmed to be included.
【００２２】[0022]
【実施例２】ソックスレ−抽出器を装置として用いる。Example 2 A Soxhlet extractor is used as a device.
【００２３】３００ｍｌの４口丸底フラスコにハイドロ
キノン（ＨＱ）を１１．０ｇ（０．１ｍｏｌ）、ジメチ
ルカ−ボネ−トを１８．００ｇ（０．２ｍｏｌ）、炭酸
カリウムを０．６９ｇ（５ｍｍｏｌ）、溶媒としてＮ，
Ｎ−ジメチルホルムアミドを１００ｍｌ仕込む。充填部
にモレキュラ−シ−ブ（ＭＳ−４Ａ）を３０．０ｇ充填
する。オイルバスで加熱し、オイル温度１７０〜２００
℃、リフラックス状態で反応させる。１５０分後のＨＱ
転化率４２％、ハイドロキノンモノメチルエ−テル（Ｈ
Ｑ）の選択率７２％、ハイドロキノンジメチルエ−テル
（ＨＱＤＭＥ）の選択率２８％であり、５００分後のＨ
Ｑ転化率９９％、ＭＱの選択率１２％、ＨＱＤＭＥの選
択率８８％であった。また、ガスクロマトグラフィ−に
おける不純物の割合は約０．５％であった。In a 300 ml four-necked round bottom flask, 11.0 g (0.1 mol) of hydroquinone (HQ), 18.00 g (0.2 mol) of dimethyl carbonate and 0.69 g (5 mmol) of potassium carbonate, N as a solvent
Charge 100 ml of N-dimethylformamide. 30.0 g of molecular sieve (MS-4A) is charged in the filling part. Heated in an oil bath, oil temperature 170-200
React in the reflux condition at ℃. HQ after 150 minutes
42% conversion, hydroquinone monomethyl ether (H
The selectivity of Q) is 72%, the selectivity of hydroquinone dimethyl ether (HQDME) is 28%, and H after 500 minutes
The Q conversion was 99%, the MQ selectivity was 12%, and the HQDME selectivity was 88%. The ratio of impurities in gas chromatography was about 0.5%.
【００２４】[0024]
【発明の効果】本発明によれば、含窒素複素環式化合物
又はアミド結合を持つ化合物を溶媒として使用すること
により、上記の反応が大気圧以下の圧力で行うことがで
きる。これにより設備費、用役費を抑制することが可能
となり、目的とする芳香族エ−テル化合物をより安価で
製造することができる。また、溶媒が安定であるため、
塩基性び強い触媒の使用が可能であり、反応速度を大き
くできる。さらに、不純物の量を最小限に抑えることが
できるので、精製の負担が小さくコストを抑えることが
できる。INDUSTRIAL APPLICABILITY According to the present invention, the above reaction can be carried out under atmospheric pressure by using a nitrogen-containing heterocyclic compound or a compound having an amide bond as a solvent. This makes it possible to reduce equipment costs and utility costs, and to produce the desired aromatic ether compound at a lower cost. Also, since the solvent is stable,
It is possible to use a basic and strong catalyst, and the reaction rate can be increased. Further, since the amount of impurities can be minimized, the burden of purification is small and the cost can be suppressed.
Claims (3)
類を炭酸アルキルエステルと反応させる芳香族エ−テル
化合物の製造方法において、含窒素複素環式化合物又は
アミド結合を持つ化合物を溶媒として用いることを特徴
とする芳香族エ−テル化合物の製造方法。1. A method for producing an aromatic ether compound in which a phenol is reacted with a carbonic acid alkyl ester in the presence of an alkaline catalyst, a nitrogen-containing heterocyclic compound or a compound having an amide bond is used as a solvent. A method for producing an aromatic ether compound, comprising:
アルキルホルムアミド又はアルキルアセトアミドを用い
ることを特徴とする請求項１記載の芳香族エ−テル化合
物の製造方法。2. A solvent such as pyridine or a pyridine derivative,
The method for producing an aromatic ether compound according to claim 1, wherein alkylformamide or alkylacetamide is used.
とを特徴とする請求項１記載の芳香族エ−テル化合物の
製造方法。3. The method for producing an aromatic ether compound according to claim 1, wherein an alkali metal salt is used as the catalyst.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4294917A JPH06145091A (en) | 1992-11-04 | 1992-11-04 | Production of aromatic ether compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4294917A JPH06145091A (en) | 1992-11-04 | 1992-11-04 | Production of aromatic ether compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH06145091A true JPH06145091A (en) | 1994-05-24 |
Family
ID=17813930
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4294917A Pending JPH06145091A (en) | 1992-11-04 | 1992-11-04 | Production of aromatic ether compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH06145091A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0846672A1 (en) * | 1996-12-05 | 1998-06-10 | ENICHEM S.p.A. | Process for the synthesis of 2-hydroxy-4-alkyloxy benzophenone |
| US6794547B2 (en) | 2001-02-23 | 2004-09-21 | Snpe | Process for the synthesis of aryl alkyl monoethers |
| CN113509947A (en) * | 2021-07-21 | 2021-10-19 | 陕西煤业化工技术研究院有限责任公司 | Catalyst for synthesizing p-methyl anisole and preparation method and application thereof |
-
1992
- 1992-11-04 JP JP4294917A patent/JPH06145091A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0846672A1 (en) * | 1996-12-05 | 1998-06-10 | ENICHEM S.p.A. | Process for the synthesis of 2-hydroxy-4-alkyloxy benzophenone |
| US5849955A (en) * | 1996-12-05 | 1998-12-15 | Enichem S.P.A. | Process for the synthesis of 2-hydroxy-4-alkyloxy benzophenone |
| US6794547B2 (en) | 2001-02-23 | 2004-09-21 | Snpe | Process for the synthesis of aryl alkyl monoethers |
| CN113509947A (en) * | 2021-07-21 | 2021-10-19 | 陕西煤业化工技术研究院有限责任公司 | Catalyst for synthesizing p-methyl anisole and preparation method and application thereof |
| CN113509947B (en) * | 2021-07-21 | 2023-09-26 | 陕西煤业化工技术研究院有限责任公司 | Catalyst for synthesizing p-methylanisole as well as preparation method and application thereof |
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