JPS6012329B2 - Manufacturing method of resorcinol - Google Patents
Manufacturing method of resorcinolInfo
- Publication number
- JPS6012329B2 JPS6012329B2 JP51022682A JP2268276A JPS6012329B2 JP S6012329 B2 JPS6012329 B2 JP S6012329B2 JP 51022682 A JP51022682 A JP 51022682A JP 2268276 A JP2268276 A JP 2268276A JP S6012329 B2 JPS6012329 B2 JP S6012329B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- present
- 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
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (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−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 previously prepared aromatic nitro compounds such as o, m, or p-dinitrobenzene with one or two 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−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一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−ジヒドロキシベンゼンまたはｐ一
ジヒドロキシベンゼソの例えば１ひげの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 (resorcinol) is hardly produced in an amount that is less than, for example, one whisker of o-dihydroxybenzene or p-dihydroxybenzene, which is preferentially produced. 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, and found that hydrogen was added to the reaction system in the presence of a commonly used hydrogenation catalyst. We have found that it is extremely effective to do so, and have arrived at the present invention.
即ち、本発明は水素添加用触媒の存在下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 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、パ
ラジウム、白金またはそれらの酸化物であり、これらは
混合物として使用することもできる。The hydrogenation catalyst used in the present invention is palladium, platinum or oxides thereof, and they can also be used as a mixture.
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
速度が増大する額向にあり、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。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 increases. It is in the range of .001 to 100 evenings. The reaction conditions for the reaction according to the present invention can be selected in consideration of reaction rate, yield, selectivity, etc.
まず軸に関しては特に制限はないが、舟０〜９の範囲で
適当に選ぶ事ができる。First of all, there are no particular restrictions on the axis, but it can be selected appropriately within the range of boats 0 to 9.
本発明の反応に用いる反応温度に関しては、一般に１５
０〜３００℃の範囲である。Regarding the reaction temperature used in the reaction of the present invention, generally 15
It is in the range of 0 to 300°C.
反応温度が高くなる程、反応速度が大きくなるが副生物
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の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０〜２００ｋｇ／地の範囲である。As the reaction temperature increases, the reaction rate increases, but by-products increase, so it is necessary to select an appropriate reaction temperature. The reaction pressure used in the present invention is not particularly limited, 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 kg/ground.
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−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 according to the present invention and m-dinitrobenzene are brought into contact with each other in cocurrent or countercurrent 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【の擬梓機につきチタン製オートク
レープ中にｍ−ジニトロベンゼン８．４夕、５２の５％
Ｐｔ−Ｃまたは５％Ｐｄ一Ｃおよび水９０夕を入れ「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、オートクレープを燭拝しながら加熱昇温し、反
応圧力５０ｋｇ′の、反応温度２５０℃で２時間反応を
行った。Example contents 8.4 hours of m-dinitrobenzene, 5% of 52 in a titanium autoclave for a 200 [simulated Azusa machine]
After adding Pt-C or 5% Pd-C and water for 90 minutes, the air in the autoclave was replaced with nitrogen gas and hydrogen was sealed in. The autoclave was then heated and heated to a reaction pressure of 50 kg. The reaction was carried out at a reaction temperature of 250° C. for 2 hours.
Claims (1)
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法。1. A method for producing resorcinol, which comprises reacting m-dinitrobenzene with hydrogen and water in the presence of a palladium- or platinum-containing catalyst.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP51022682A JPS6012329B2 (en) | 1976-03-04 | 1976-03-04 | Manufacturing method of resorcinol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP51022682A JPS6012329B2 (en) | 1976-03-04 | 1976-03-04 | Manufacturing method of resorcinol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS52106826A JPS52106826A (en) | 1977-09-07 |
| JPS6012329B2 true JPS6012329B2 (en) | 1985-04-01 |
Family
ID=12089621
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51022682A Expired JPS6012329B2 (en) | 1976-03-04 | 1976-03-04 | Manufacturing method of resorcinol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6012329B2 (en) |
-
1976
- 1976-03-04 JP JP51022682A patent/JPS6012329B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS52106826A (en) | 1977-09-07 |
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