JPS6012330B2 - Manufacturing method of resorcinol - Google Patents
Manufacturing method of resorcinolInfo
- Publication number
- JPS6012330B2 JPS6012330B2 JP51022684A JP2268476A JPS6012330B2 JP S6012330 B2 JPS6012330 B2 JP S6012330B2 JP 51022684 A JP51022684 A JP 51022684A JP 2268476 A JP2268476 A JP 2268476A JP S6012330 B2 JPS6012330 B2 JP S6012330B2
- Authority
- JP
- Japan
- Prior art keywords
- present
- reaction
- dinitrobenzene
- resorcinol
- dihydroxybenzene
- 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.)
- Expired
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)
Description
【発明の詳細な説明】
本発明はｍ−ジニトロベンゼンからしゾルシンを製造す
る方法の改良に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to improvements in the process for producing m-dinitrobenzene mustard solcin.
更に詳しくはｍージニトロベンゼンのニトロ基を水酸基
に変えてレゾルシンを製造する方法に関する。本発明者
らはさきにｏ、ｍまたはｐージニトロベンゼンなどの芳
香族ニトロ化合物を酸性硫酸アルカリ金属塩、硫酸アル
カリ金属塩、酸性硫酸アンモニウム塩および硫酸アンモ
ニウム塩からなる群から選ばれた１種または２種以上の
塩の存在下に水と反応させることにより種々のフェノー
ル類を製造し得ることを見出しこの方法を提供した。More specifically, the present invention relates to a method for producing resorcinol by changing the nitro group of m-dinitrobenzene to a hydroxyl group. The present inventors first prepared aromatic nitro compounds such as o-, m-, or p-dinitrobenzene by combining one or two aromatic nitro compounds selected from the group consisting of acidic alkali metal sulfates, alkali metal sulfates, acidic ammonium sulfates, and ammonium sulfates. The present inventors have discovered that various phenols can be produced by reacting them with water in the presence of more than one type of salt, and have provided this method.
しかし乍らこの反応は、例えばｏ、ｍまたはｐージニト
ロベンゼンの何れのニトロ化合物を用いた場合において
もｏ−ジヒドロキシベンゼン（カテコール）およびｐ一
ジヒドロキシベンゼン（ハイドロキノン）が優先的に生
成され、ｍ−ジヒドロキシベンゼン（レゾルシン）は優
先的に生成されるｏ一ジヒドロキシベンゼンまたはｐ一
ジヒドロキシベンゼンの例えば１０分の１量にも満たな
い程度にしか生成し難い。本発明者らは上記した実情に
鑑み、ｍージニトロベンゼンよりｍ−ジヒドロキシベン
ゼンを高収率で得る方法について鋭意検討した結果、通
常用いられる水素添加用触媒と無機酸との存在下に反応
系に水素を添加することが極めて有効であることを見出
し、本発明に到達した。However, in this reaction, o-dihydroxybenzene (catechol) and p-dihydroxybenzene (hydroquinone) are preferentially produced, regardless of whether a nitro compound such as o-, m-, or p-dinitrobenzene is used; -Dihydroxybenzene (resorcin) is difficult to produce, for example, in an amount less than one-tenth of the preferentially produced o-dihydroxybenzene or p-dihydroxybenzene. In view of the above-mentioned circumstances, the present inventors conducted intensive studies on a method for obtaining m-dihydroxybenzene from m-dinitrobenzene in high yield. The present invention was achieved by discovering that it is extremely effective to add hydrogen to.
即ち、本発明は無機酸と水素添加用触媒との存在下ｍー
ジニトロベンゼンと水素および水とを反応させることか
らなるレゾルシンの製造方法である。That is, the present invention is a method for producing resorcinol, which comprises reacting m-dinitrobenzene with hydrogen and water in the presence of an inorganic acid and a hydrogenation catalyst.
本発明において用いられる水素添加用触媒としては、白
金またはその酸化物を含有する触媒、すなわち白金含有
触媒である。The hydrogenation catalyst used in the present invention is a catalyst containing platinum or an oxide thereof, that is, a platinum-containing catalyst.
本発明で使用される前記水素添加用触媒の使用量に関し
ても特に制限はないが、その使用量が増大するほど反応
速度が増大する煩向にあり、通常ｍ−ジニトロベンゼン
１モルに対して０．００１〜１００夕の範囲である。本
発明の方法において用いられるもう一つの触媒である無
機酸としては、硫酸、りん酸またはけし、タングステン
酸から選ばれた無機酸が用いられる。本発明で使用され
る無機酸触媒の濃度に関しては特に制限がないが、触媒
の種類及び濃度によって生成するレゾルシンの収率及び
選択率に影響があるので、触媒活性及び経済性を考慮し
て適宜選択され、通常０．０１〜１０モルノその範囲で
用いられる。There is no particular restriction on the amount of the hydrogenation catalyst used in the present invention, but as the amount used increases, the reaction rate tends to increase. It is in the range of .001 to 100 evenings. As another inorganic acid catalyst used in the method of the present invention, an inorganic acid selected from sulfuric acid, phosphoric acid, poppy, and tungstic acid is used. There is no particular restriction on the concentration of the inorganic acid catalyst used in the present invention, but since the yield and selectivity of the resorcinol produced are affected by the type and concentration of the catalyst, it may be appropriate to It is selected and usually used in the range of 0.01 to 10 mol.
本発明による反応の反応条件は、反応速度、収率、選択
率等を考慮して選ぶ事ができる。The reaction conditions for the reaction according to the present invention can be selected in consideration of reaction rate, yield, selectivity, etc.
まづｐＨに関しては特に制限はないが、ＰＨＯ〜９の範
囲で適当に選ぶ事ができる。First, there is no particular restriction on the pH, but it can be appropriately selected within the range of PHO to 9.
本発明に用いる反応温度に関しては、一般に１５０〜３
００ＣＯの範囲である。Regarding the reaction temperature used in the present invention, generally 150 to 3
It is in the range of 00CO.
反応温度が高くなる程、反応速度が大きくなるが創生物
が増加するので適当な反応温度を選ぶ必要がある。本発
明に用いる反応圧力に関しては特に制限はないが、常圧
または高圧の水素雰囲気で実施することができ、好まし
い水素圧は０〜２００ｋ９／地の範囲である。As the reaction temperature increases, the reaction rate increases, but the number of created organisms increases, so it is necessary to select an appropriate reaction temperature. There is no particular restriction on the reaction pressure used in the present invention, but the reaction can be carried out in a hydrogen atmosphere at normal pressure or high pressure, and the preferred hydrogen pressure is in the range of 0 to 200 k9/kg.
本発明に用いる反応装置に関しては、特に制限はなく、
一般に回分式または連続式の液相用の反応装置が用いら
れる。There are no particular restrictions on the reaction apparatus used in the present invention,
Batch or continuous liquid phase reactors are generally used.
連続式では本発明による触媒を含む水溶液とｍージニト
ロベンゼンとを水素雰囲気下で並流または向流で接触せ
しめ、反応器から排出する反応液からしゾルシンを蒸溜
分離したのち残液を反応器に循環する方法によって実施
することができる。次に実施例により本発明をさらに説
明する。In the continuous system, an aqueous solution containing the catalyst of the present invention and m-dinitrobenzene are brought into contact with each other in parallel or countercurrent flow under a hydrogen atmosphere, and after distilling and separating the mustard solcin from the reaction liquid discharged from the reactor, the remaining liquid is transferred to the reactor. This can be carried out by a method of cycling through the process. Next, the present invention will be further explained by examples.
実施例内容２００の‘の蝿投機つきチタン製オートクレ
ープ中にｍージニトロベンゼン８．４夕、下表に示すよ
うな種および量の水素添加触媒並びに無機酸触媒、およ
び水９Ｍを入れ、オートクレープ中の空気を窒素ガスで
置換し、水素を封入した後、オートクレープを潰拝しな
がら加熱昇温し、下表に示すような反応温度で２時間反
応を行った結果を下表に示した。Example Contents 8.4 m dinitrobenzene, hydrogenation catalysts and inorganic acid catalysts of the species and amounts shown in the table below, and 9 M of water were placed in a 200 ml titanium autoclave. After replacing the air in the crepe with nitrogen gas and filling it with hydrogen, the autoclave was heated while being crushed, and the reaction was carried out for 2 hours at the reaction temperature shown in the table below.The results are shown in the table below. Ta.
Claims (1)
た無機酸とパラジウム含有触媒との存在下ｍ−ジニトロ
ベンゼンと水素および水とを反応させることを特徴とす
るレゾルシンの製造方法。1. A method for producing resorcinol, which comprises reacting m-dinitrobenzene with hydrogen and water in the presence of an inorganic acid selected from sulfuric acid, phosphoric acid, or silicotungstic acid and a palladium-containing catalyst.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP51022684A JPS6012330B2 (en) | 1976-03-04 | 1976-03-04 | Manufacturing method of resorcinol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP51022684A JPS6012330B2 (en) | 1976-03-04 | 1976-03-04 | Manufacturing method of resorcinol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS52106828A JPS52106828A (en) | 1977-09-07 |
| JPS6012330B2 true JPS6012330B2 (en) | 1985-04-01 |
Family
ID=12089680
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51022684A Expired JPS6012330B2 (en) | 1976-03-04 | 1976-03-04 | Manufacturing method of resorcinol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6012330B2 (en) |
-
1976
- 1976-03-04 JP JP51022684A patent/JPS6012330B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS52106828A (en) | 1977-09-07 |
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