JPS62178546A - Production of alkyl 1-hydroxy-2-naphthoate - Google Patents
Production of alkyl 1-hydroxy-2-naphthoateInfo
- Publication number
- JPS62178546A JPS62178546A JP61021044A JP2104486A JPS62178546A JP S62178546 A JPS62178546 A JP S62178546A JP 61021044 A JP61021044 A JP 61021044A JP 2104486 A JP2104486 A JP 2104486A JP S62178546 A JPS62178546 A JP S62178546A
- Authority
- JP
- Japan
- Prior art keywords
- hydroxy
- naphthoic acid
- alkyl
- producing
- solvent
- 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）
本発明はアルキル−１−ヒドロキシ−２−ナフトエ酸の
製造方法に係り、更に詳しくはｌ−ヒドロキシ−２−ナ
フトエ酸とジアルキル硫酸とよりアルキル−１−ヒドロ
キシ−２−ナフトエ酸を製造する方法に関するものであ
る。Detailed Description of the Invention (Industrial Field of Application) The present invention relates to a method for producing alkyl-1-hydroxy-2-naphthoic acid, and more specifically, it relates to a method for producing alkyl-1-hydroxy-2-naphthoic acid, and more specifically, it relates to a method for producing alkyl-1-hydroxy-2-naphthoic acid, and more specifically, it relates to a method for producing alkyl-1-hydroxy-2-naphthoic acid. The present invention relates to a method for producing -1-hydroxy-2-naphthoic acid.
（従来の技術）
アルキル−１−ヒドロキシ−２−ナフトエ酸は掻めて有
用な化合物であって、特にカラー写真材料、染料顔料な
どの製造にあたっては欠くことの出来ない中間体であり
、近年、感圧紙や怒熱紙用の発色助剤として多量に消費
されようとしている征目されるべき化合物である。(Prior Art) Alkyl-1-hydroxy-2-naphthoic acid is an extremely useful compound, and is an indispensable intermediate especially in the production of color photographic materials, dyes and pigments, and in recent years, It is a compound that should be exploited as it is about to be consumed in large quantities as a coloring aid for pressure-sensitive paper and thermal paper.
これらの用途の使用に耐えるアルキル−１−ヒドロキシ
−２−ナフトエ酸の特色としては特に高純度であること
が必要であり、とりわけ原料である１−ヒドロキシ−２
−ナフトエ酸が製品中に含有されることは極端に制限さ
れなければならず、例えば′１−ヒドロキシ−２−ナフ
トエ酸の含有量は０．０１％以下に規制しないと上記用
途には化合物としての価値が発揮されないことが多い。The characteristics of alkyl-1-hydroxy-2-naphthoic acids that can be used in these applications require particularly high purity.
-The content of naphthoic acid in products must be extremely limited; for example, the content of '1-hydroxy-2-naphthoic acid must be regulated to 0.01% or less for the above uses as a compound. value is often not realized.
ところで、かかるアルキル−１−ヒドロキシ−２−ナフ
トエ酸に関しては、その優れた製造方法は殆ど知られて
おらず、僅かに例えば特開昭５９−１６７５４４号公報
などにその例が示されているにすぎない。By the way, with regard to such alkyl-1-hydroxy-2-naphthoic acids, almost no excellent manufacturing method is known, and only a few examples are shown in JP-A-59-167544. Only.
しかも、この方法も同公報の詳細にあるようにすぐれた
品實の製品を得るためには原料であるオキシナフトエ酸
を極めて特殊で、かつ工業的に実施しに（い精製条件で
精製することが必要であり、実用化には問題を残してい
る。Moreover, as detailed in the same publication, in order to obtain a product of excellent quality, this method requires extremely special and industrially difficult purification conditions for the raw material oxynaphthoic acid. is necessary, and there are still problems in practical implementation.
その他、後述の比較例に示したようなアルキル−２−ヒ
ドロキシ−３−ナフトエ酸の製造方法に類似した方法も
一方において考えられるが、この方法も上記の如き用途
の使用に耐える品位の目的物を得るには難がある。On the other hand, a method similar to the method for producing alkyl-2-hydroxy-3-naphthoic acid as shown in the comparative example described below is also considered, but this method also produces a product with a quality that can be used for the above-mentioned purposes. It is difficult to obtain.
（発明が解決しようとする問題点）
本発明者は、上述の如き実状に対処し、工業的に有利な
アルキル−１−ヒドロキシ−２−ナフトエ酸の製造方法
について鋭意検討を重ね、その結果、１−ヒドロキシ−
２−ナフトエ酸とジアルキル硫酸とを反応させるにあた
り、脂肪族ケトン類を溶媒として用い、かつ、炭酸アル
カリ又は重炭酸アルカリの存在下で反応せしめることに
より、前記開示された方法の如（原料を特別に精製する
こともなく工業的に容易に実施できることを知見するに
至り、本発明に到達した。(Problems to be Solved by the Invention) In order to address the above-mentioned circumstances, the present inventor has conducted extensive studies on an industrially advantageous method for producing alkyl-1-hydroxy-2-naphthoic acid, and as a result, 1-hydroxy-
In reacting 2-naphthoic acid and dialkyl sulfuric acid, aliphatic ketones are used as a solvent and the reaction is carried out in the presence of an alkali carbonate or an alkali bicarbonate. It was discovered that the process can be easily carried out industrially without further purification, leading to the present invention.
（問題点を解決するための手段）
即ち、本発明の特徴とするところは、１−ヒドロキシ−
２−ナフトエ酸とジアルキル硫酸とよりアルキル−１−
ヒドロキシ−２−ナフトエ酸を製造するに際し、脂肪族
ケトン類を溶媒とし、かつ炭酸アルカリまたは重炭酸ア
ルカリの存在下で反応せしめることにある。(Means for solving the problems) That is, the feature of the present invention is that 1-hydroxy-
2-naphthoic acid and dialkyl sulfate and alkyl-1-
In producing hydroxy-2-naphthoic acid, the reaction is carried out using an aliphatic ketone as a solvent and in the presence of an alkali carbonate or an alkali bicarbonate.
ここで、本発明に使用されるジアルキル硫酸は通常、ジ
メチル硫酸またはジエチル硫酸である。Here, the dialkyl sulfate used in the present invention is usually dimethyl sulfate or diethyl sulfate.
そして、これらの使用モル比としては１−ヒドロキシ−
２−ナフトエ酸に対して１．０〜１．５、好ましくは１
．０〜１．２である。若し、１．０以下であれば反応が
充分に完結せず、未反応が残り、一方、１．５以上では
副反応物が生じるので、上記便用モル比が好適である。The molar ratio of these used is 1-hydroxy-
1.0 to 1.5, preferably 1 to 2-naphthoic acid
．． It is 0 to 1.2. If it is less than 1.0, the reaction will not be completed sufficiently and unreacted substances will remain, while if it is more than 1.5, side reactants will be produced, so the above convenient molar ratio is suitable.
又、反応用の溶媒は具体的にはアセトン、メチルエチル
ケトン、メチルイソプロピルケトン、メチルイソプチル
ケトンが挙げられ、その使用量はｌ−ヒドロキシ−２−
ナフトエ酸に対して２．０〜１ｓ、ｏｎ量倍であるが、
経済性より好ましくは３．Ｏ〜６．ｏｉｕｔ倍である。Specific examples of the solvent for the reaction include acetone, methyl ethyl ketone, methyl isopropyl ketone, and methyl isobutyl ketone, and the amount used is l-hydroxy-2-
2.0 to 1 s, twice the amount of on, compared to naphthoic acid,
Preferably 3. from economical point of view. O~6. It is oiut times.
更に炭酸アルカリまたは重炭酸アルカリとしては炭酸ナ
トリウム、炭酸カリウム、重炭酸ナトリウム、重炭酸カ
リウムの単味又は任意の混合物が使用され、その使用量
はｌ−ヒドロキシ−２−す°フトエ酸に対して０．５〜
３．０モル倍、好ましくは０．５〜１．５モル倍である
。Further, as the alkali carbonate or alkali bicarbonate, sodium carbonate, potassium carbonate, sodium bicarbonate, or potassium bicarbonate may be used alone or in any mixture, and the amount used is based on l-hydroxy-2-sulphthoic acid. 0.5～
The amount is 3.0 times by mole, preferably 0.5 to 1.5 times by mole.
この場合も３．０モル倍以上では副反応物の生成が起こ
る。In this case as well, if the amount is 3.0 moles or more, by-products will be produced.
なお、反応温度は通常、高められた温度が選定され、例
えば３０〜１１０℃、好ましくは５０〜８０℃である。Note that the reaction temperature is usually selected to be elevated, for example 30 to 110°C, preferably 50 to 80°C.
か（して、反応を円滑に進行せしめた後、副生じた無機
塩をろ過等により除去し、得られた溶液を深冷すると原
料である１−ヒドロキシ−２−ナフトエ酸を実質的に全
く含有しないアルキル−１−ヒドロキシ−２−ナフトエ
酸が得られる。After allowing the reaction to proceed smoothly, the by-product inorganic salts are removed by filtration, etc., and the resulting solution is deeply cooled to completely remove the raw material 1-hydroxy-2-naphthoic acid. A free alkyl-1-hydroxy-2-naphthoic acid is obtained.
このアルキル−１−ヒドロキシ−２−ナフトエ酸の収率
は通常、８５〜９５％であり、極めて好効率である。The yield of this alkyl-1-hydroxy-2-naphthoic acid is usually 85 to 95%, which is an extremely high efficiency.
ここで、得られるアルキル−１−ヒドロキシ−２−ナフ
トエ酸は具体的にはメチル−１−ヒドロキシ−２−ナフ
トエ酸またはエチル＝１−ヒドロキシ−２−ナフトエ酸
である。Here, the alkyl-1-hydroxy-2-naphthoic acid obtained is specifically methyl-1-hydroxy-2-naphthoic acid or ethyl-1-hydroxy-2-naphthoic acid.
（実施例）
以下、史に本発明方法の具体的な実施例を比較例と共に
説明する。(Examples) Hereinafter, specific examples of the method of the present invention will be described together with comparative examples.
比較例−１
先ず、メチル−２−ヒドロキシ−３−ナフトエ酸の製造
につき説明する。Comparative Example-1 First, the production of methyl-2-hydroxy-3-naphthoic acid will be explained.
ジャーナル・オブ・ザ・ケミカル ソサエティ・オブ・
ロンドン（Ｊｏｕｒｎａｌ ｏｆ ｔｈｅ Ｃｈｅｍｉ
ｃａｌＳｏｃｉｅｔｙ ｏｆ Ｌｏｎｄｏｎ） ９７
、 １７４ Ｂ 、に記載の方法に′Ｉ＄して用水の
メタノール１００ｇ、２−ヒドロキシ−３−ナフトエ酸
３７．６ｇおよび９８％硫酸２０．０ｇの混合物を６８
℃にて撹拌しつつ１２時間保った。Journal of the Chemical Society of
London (Journal of the Chemi
CalSociety of London) 97
, 174 B, a mixture of 100 g of methanol, 37.6 g of 2-hydroxy-3-naphthoic acid, and 20.0 g of 98% sulfuric acid was added to 68
The mixture was kept at ℃ for 12 hours with stirring.
その後、冷却して１５℃とし生成した結晶をろ別し、メ
タノールで洗浄後、乾燥したところ、２−ヒドロキシ−
３−ナフトエ酸を全く含有しないメチル−２−ヒドロキ
シ−３−ナフトエ酸を９１％の収率で得た。Thereafter, the crystals formed were cooled to 15°C, filtered out, washed with methanol, and dried, resulting in 2-hydroxy-
Methyl-2-hydroxy-3-naphthoic acid containing no 3-naphthoic acid was obtained with a yield of 91%.
比較例−２
次に上記方法に準じてメチル−１−ヒドロキシ−２−ナ
フトエ酸の製造も試みた。即ち、上記比較例１における
２−ヒドロキシ、−３−ナフトエ酸に替えｌ−ヒドロキ
シ−２−ナフトエ酸を使用した。Comparative Example 2 Next, an attempt was made to produce methyl-1-hydroxy-2-naphthoic acid according to the above method. That is, 1-hydroxy-2-naphthoic acid was used instead of 2-hydroxy-3-naphthoic acid in Comparative Example 1 above.
その結果は反応は数１０パーセントの１−ヒドロキシ−
２−ナフトエ酸を残存させたまま停止した。The results showed that the reaction was several tens of percent 1-hydroxy-
The reaction was stopped with 2-naphthoic acid remaining.
常法により結晶を取り出し、再結晶操作により精製を試
みたが、■−ヒドロキシ−２−ナフトエ酸の含有量を０
．５％以下とするには工業的手段では掻めて困難であっ
た。Crystals were extracted by a conventional method and purification was attempted by recrystallization, but the content of ■-hydroxy-2-naphthoic acid was reduced to 0.
．． It was extremely difficult to reduce the content to 5% or less using industrial means.
実施例−ｌ
アセトン８４５ｇ、１−ヒドロキシ−２−ナフトエ酸１
８８ｇ、炭酸カリウム８０ｇの混合物を５０℃として撹
拌し、ジメチル硫酸１３６．０ｇを２時間で滴下し、５
０〜６０℃にて３時間保った。その後、５５℃にて無機
塩をろ別し、５℃にて結晶をろ別し、アセトン水溶液、
次いで水で洗浄し乾燥したところ、ｌ−ヒドロキシ−２
−ナフトエ酸を全く含有しないメチル−１−ヒドロキシ
−２−ナフトエ酸を収率９３％で得た。Example-l Acetone 845g, 1-hydroxy-2-naphthoic acid 1
A mixture of 88 g of potassium carbonate and 80 g of potassium carbonate was stirred at 50°C, and 136.0 g of dimethyl sulfuric acid was added dropwise over 2 hours.
It was kept at 0-60°C for 3 hours. Thereafter, inorganic salts were filtered out at 55°C, crystals were filtered out at 5°C, and an acetone aqueous solution,
Then, when washed with water and dried, l-hydroxy-2
-Methyl-1-hydroxy-2-naphthoic acid containing no naphthoic acid was obtained in a yield of 93%.
このものは前記本発明の意図する用途になんら差し支え
なく使用できるものであった。This product could be used without any problem for the intended purpose of the present invention.
実施例−２
実施例−１においてジメチル硫酸にかえ同モルのジエチ
ル硫酸を用いた。その結果、１−ヒドロキシ−２−ナフ
トエ酸を全く含有しないエチル−１−ヒドロキシ−２−
ナフトエ酸を収率９１％で得た。Example 2 In Example 1, the same molar amount of diethyl sulfate was used instead of dimethyl sulfate. As a result, ethyl-1-hydroxy-2-
Naphthoic acid was obtained with a yield of 91%.
このものも前記実施例−１と同様、本発明の意図する前
記用途に適合するものであった。Like Example 1, this product was also suitable for the intended use of the present invention.
実施例−３
実施例−１においてアセトンに替え同重量のメチルエチ
ルケトンを用いた。ただし反応温度を６０〜６５℃とし
た。その結果、収率９２％で目的物を得た。このものの
品笛も極めて優秀であり、充分に上記用途に耐え得るも
のであった。Example 3 In Example 1, the same weight of methyl ethyl ketone was used instead of acetone. However, the reaction temperature was 60 to 65°C. As a result, the desired product was obtained with a yield of 92%. The quality of this whistle was also extremely good, and it was able to withstand the above-mentioned uses.
実施例〜４
実施例−１において炭酸カリウムに替え、同モルの炭酸
ナトリウムを使用し、目的物を８８％の収率で得た。Example 4 In Example 1, the same molar amount of sodium carbonate was used instead of potassium carbonate, and the target product was obtained in a yield of 88%.
また、炭酸ナトリウムに替え倍モルの■炭酸ナトリウム
を用いて収率８７％で目的物を得た。Further, by replacing sodium carbonate with twice the molar amount of sodium carbonate, the desired product was obtained in a yield of 87%.
これらのものも、前例同様、充分前記用途の使用に耐え
得るものであった。Like the previous example, these products were also able to withstand the above-mentioned uses.
比較例−３
実施例−１においてアセトンに替え、同重量の下表の各
溶媒を用いたところ、いずれの場合も生成物の純度は極
めて劣悪であった。その状況を表中に併記する。Comparative Example 3 In Example 1, the same weight of each solvent listed in the table below was used in place of acetone, and in all cases the purity of the product was extremely poor. The situation is also listed in the table.
表中には生成物中の１−ヒドロキシ−２−ナフトエ酸に
含まれる不純物の含量（％）を示した。The table shows the content (%) of impurities contained in 1-hydroxy-2-naphthoic acid in the product.
比較例−４
実施例−１において炭酸カリウムに替え同モルの水酸化
ナトリウムを用いた。Comparative Example-4 In Example-1, the same molar amount of sodium hydroxide was used instead of potassium carbonate.
溶媒アセトンの変性物が生成し、かつ目的物は全く次工
程の使用に耐え得ないことが判明した。It was found that a modified product of the solvent acetone was produced and the target product could not be used in the next step at all.
（発明の効果）
本発明は前記各実施例より明らかなように、脂肪族ケト
ン類を溶媒とし、かつ、炭酸アルカリまたは重炭酸アル
カリの存在下で反応せしめることにより前述した１−ヒ
ドロキシ−２−ナフトエ酸の含量の少ないアルキル＝１
−ヒドロキシ−２−ナフトエ酸を有利に製造することが
でき、近時、その用途が征目され、益々、消費拡大が期
待されるアルキル−１−ヒドロキシ−２−ナフトエ酸の
製造方法として今後における実用上、頗る顕著な効果を
奏する。(Effects of the Invention) As is clear from the above-mentioned Examples, the present invention provides the above-mentioned 1-hydroxy-2- Alkyl with low content of naphthoic acid = 1
-Hydroxy-2-naphthoic acid can be produced advantageously, and its use has recently been explored, and it is expected to be used in the future as a method for producing alkyl-1-hydroxy-2-naphthoic acid, whose consumption is expected to increase further. In practical terms, it has a remarkable effect.
Claims (1)
とよりなるアルキル＝１−ヒドロキシ−２−ナフトエ酸
を製造するにあたり脂肪族ケトン類を溶媒とし、かつ、
炭酸アルカリまたは重炭酸アルカリの存在下で反応せし
めることを特徴とするアルキル＝１−ヒドロキシ−２−
ナフトエ酸の製造方法。 ２、脂肪族ケトン類がアセトン、メチルエチルケトン、
メチルイソプロピルケトン、メチルイソプチルケトンか
らなる群より選ばれた少なくとも１つであるアルキル１
−ヒドロキシ−２−ナフトエ酸の製造方法。 ３、炭酸アルカリまたは重炭酸アルカリが炭酸ナトリウ
ム、炭酸カリウム、重炭酸ナトリウムまたは重炭酸カリ
ウムからなる群より選ばれた少なくとも１つであるアル
キル＝１−ヒドロキシ−２−ナフトエ酸の製造方法。 ４、アルキル＝１−ヒドロキシ−２−ナフトエ酸がメチ
ル＝１−ヒドロキシ−２−ナフトエ酸またはエチル＝１
−ヒドロキシ−２−ナフトエ酸であるアルキル＝１−ヒ
ドロキシ−２−ナフトエ酸の製造方法。[Claims] In producing an alkyl 1-hydroxy-2-naphthoic acid consisting of 1,1-hydroxy-2-naphthoic acid and dialkyl sulfuric acid, an aliphatic ketone is used as a solvent, and
Alkyl 1-hydroxy-2- characterized in that it is reacted in the presence of an alkali carbonate or an alkali bicarbonate.
Method for producing naphthoic acid. 2. Aliphatic ketones include acetone, methyl ethyl ketone,
Alkyl 1 which is at least one selected from the group consisting of methyl isopropyl ketone and methyl isobutyl ketone
- A method for producing hydroxy-2-naphthoic acid. 3. A method for producing alkyl 1-hydroxy-2-naphthoic acid, wherein the alkali carbonate or alkali bicarbonate is at least one selected from the group consisting of sodium carbonate, potassium carbonate, sodium bicarbonate, or potassium bicarbonate. 4, alkyl=1-hydroxy-2-naphthoic acid is methyl=1-hydroxy-2-naphthoic acid or ethyl=1
- A method for producing alkyl 1-hydroxy-2-naphthoic acid, which is hydroxy-2-naphthoic acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61021044A JPS62178546A (en) | 1986-01-31 | 1986-01-31 | Production of alkyl 1-hydroxy-2-naphthoate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61021044A JPS62178546A (en) | 1986-01-31 | 1986-01-31 | Production of alkyl 1-hydroxy-2-naphthoate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS62178546A true JPS62178546A (en) | 1987-08-05 |
Family
ID=12043931
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61021044A Pending JPS62178546A (en) | 1986-01-31 | 1986-01-31 | Production of alkyl 1-hydroxy-2-naphthoate |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62178546A (en) |
-
1986
- 1986-01-31 JP JP61021044A patent/JPS62178546A/en active Pending
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