JPS6261009B2 - - Google Patents
Info
- Publication number
- JPS6261009B2 JPS6261009B2 JP6607380A JP6607380A JPS6261009B2 JP S6261009 B2 JPS6261009 B2 JP S6261009B2 JP 6607380 A JP6607380 A JP 6607380A JP 6607380 A JP6607380 A JP 6607380A JP S6261009 B2 JPS6261009 B2 JP S6261009B2
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- palladium
- arsenic
- reaction
- cyclohexanetriol
- 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
- 239000003054 catalyst Substances 0.000 claims description 26
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 claims description 20
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 18
- 229940079877 pyrogallol Drugs 0.000 claims description 10
- 229910052763 palladium Inorganic materials 0.000 claims description 9
- IZSANPWSFUSNMY-UHFFFAOYSA-N cyclohexane-1,2,3-triol Chemical compound OC1CCCC(O)C1O IZSANPWSFUSNMY-UHFFFAOYSA-N 0.000 claims description 8
- 229910052785 arsenic Inorganic materials 0.000 claims description 7
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052737 gold Inorganic materials 0.000 claims description 6
- 239000010931 gold Substances 0.000 claims description 6
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 5
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 5
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims description 5
- 229910052711 selenium Inorganic materials 0.000 claims description 5
- 239000011669 selenium Substances 0.000 claims description 5
- 229910052709 silver Inorganic materials 0.000 claims description 5
- 239000004332 silver Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 229910052939 potassium sulfate Inorganic materials 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 150000001339 alkali metal compounds Chemical class 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000006356 dehydrogenation reaction Methods 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 4
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 4
- 235000011151 potassium sulphates Nutrition 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- DJHGAFSJWGLOIV-UHFFFAOYSA-N Arsenic acid Chemical compound O[As](O)(O)=O DJHGAFSJWGLOIV-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229940000488 arsenic acid Drugs 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 235000013162 Cocos nucifera Nutrition 0.000 description 2
- 244000060011 Cocos nucifera Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- FNTHQRXVZDCWSP-UHFFFAOYSA-N cyclohexane-1,1,2-triol Chemical compound OC1CCCCC1(O)O FNTHQRXVZDCWSP-UHFFFAOYSA-N 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- QYHFIVBSNOWOCQ-UHFFFAOYSA-N selenic acid Chemical compound O[Se](O)(=O)=O QYHFIVBSNOWOCQ-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- -1 organic acid salts Chemical class 0.000 description 1
- SWELZOZIOHGSPA-UHFFFAOYSA-N palladium silver Chemical compound [Pd].[Ag] SWELZOZIOHGSPA-UHFFFAOYSA-N 0.000 description 1
- GPNDARIEYHPYAY-UHFFFAOYSA-N palladium(ii) nitrate Chemical compound [Pd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O GPNDARIEYHPYAY-UHFFFAOYSA-N 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- MUSFRELEIXGPKU-UHFFFAOYSA-N selanylidenepalladium Chemical compound [Pd]=[Se] MUSFRELEIXGPKU-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 description 1
- 229940071536 silver acetate Drugs 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
本発明は1,2,3−シクロヘキサントリオー
ルを脱水素してピロガロールを製造する方法に関
するものである。
さらに本発明者らは1,2,3−シクロヘキサ
ントリオールを、不活性気流中、パラジウムなど
の白金族金属触媒の存在下に脱水素してピロガロ
ールを得る方法を見出し、出願した(特願昭54−
161097)。本発明者はひきつづき、ピロガロール
の収率をさらに高めるべく努力を続けた結果、新
規な触媒系を見出し、本発明に到達したものであ
る。
本発明方法の特徴は、1,2,3−シクロヘキ
サントリオールの脱水素反応に、触媒としてパラ
ジウムならびに金、銀、ヒ素およびセレンより選
ばれる少くとも一種を使用することにあり、高い
ピロガロール収率が得られる。
以下、本発明を詳細に説明する。
触媒としてはパラジウムに金、銀、ヒ素、セレ
ンのいずれかを添加したものが用いられ、その添
加量は添加すべき元素の種類により最適添加量に
若干の差は存在するが、パラジウムに対し原子比
で2〜200%、より好ましくは5〜50%である。
触媒は担体に担持して使用されるのが好まし
い。担体としては活性炭、シリカ、アルミナ等の
多孔質で表面積の大きいものを使用するのが好ま
しいが、なかでも活性炭が特に好適である。
触媒を調製するには、通常、パラジウムならび
に金、銀、ヒ素およびセレンより選ばれる少くと
も一種の適当な化合物、例えば、塩化パラジウ
ム、硝酸パラジウム、塩化金酸、酢酸銀、ヒ酸、
セレン酸等の溶液を別途にあるいは混合して調製
し、これを担体に含浸、噴霧等適当な手段で担持
させたのち、公知の方法、例えば、水素気流中で
加熱するなどの方法で還元して行なうことができ
る。あるいは、一旦パラジウムのみを担持した触
媒を調製し、還元後、さらに金、銀、ヒ素または
セレンを担持し再還元を行なつて触媒を調製する
ことも可能である。パラジウムの担持量は1〜30
重量%程度とすることが好ましい。
本発明方法においては、触媒に、さらにアルカ
リ金属化合物を添加したものを使用することによ
り、活性を増大させ、なおかつピロガロールの収
率を一層向上させることができる。アルカリ金属
化合物としては、ナトリウム、カリウム、ルビジ
ウム、セシウムなどの硫酸塩、炭酸塩、塩化物、
有機酸塩などが例示される。これらのアルカリ金
属化合物を担体に担持するには、浸漬法、蒸発乾
固法などの通常の方法で行なうことが可能であ
り、パラジウムおよび金、銀、ヒ素、セレンの添
加元素と、アルカリ金属化合物とを担持する順序
については特に制限されない。アルカリ金属化合
物の担持量は、特に限定されるものではないが、
通常は触媒全重量に対して0.3〜30重量%、好ま
しくは1〜10重量%の範囲内で適宜選択される。
本発明方法による1,2,3−シクロヘキサン
トリオールの脱水素反応は、窒素、二酸化炭素、
水蒸気、メタン等の反応に関与しない不活性な気
体の流通下に行なうのが好ましい。反応は液相で
も気相でも行ないうる。しかしながら、反応生成
物からの触媒の分離などの点からみて気相で行な
うことが好ましい。反応温度は50〜500℃、好ま
しくは150〜350℃程度が好適である。圧力は若干
の加圧下としても反応は進行するが、常圧ないし
は減圧で反応を行なうのがより好ましい。
本発明方法において得られたピロガロールは、
カテコール等の副生物から、蒸留、晶析等の分離
手段で精製分離取得することができる。
次に本発明を実施例により更に具体的に説明す
る。
実施例 1
塩化パラジウム2.5gを濃塩酸6mlに溶解し、
これに塩化金酸0.931gを加え、水を加えて全量
を15mlとした水溶液にヤシガラ活性炭5gを減圧
下に浸漬し、一夜放置したのち70℃に加熱乾固し
た。このものにさらに10%硫酸カリウム水溶液を
一時間浸漬させたのち蒸発乾固し、窒素気流中
100℃で1時間加熱したのち、水素気流中400℃で
還元し、硫酸カリウム2.5wt%を含むパラジウ
ム・金/活性炭触媒を調製した。
この触媒0.5mlをガラス管に充填し、300℃に加
熱しながら、窒素ガスをGHSV5000hr-1で流通さ
せた。
ここに1,2,3−シクロヘキサントリオール
の10wt%水溶液をLHSV2.7hr-1で流通させ、常
圧で連続的に脱水素反応を行なつた。生成物を氷
水で冷却し、気液分離後、ガスクロマトグラフイ
および高速液体クロマトグラフイにより分析を行
なつた。反応開始後1時間時点での1,2,3−
シクロヘキサントリオールの転化率およびピロガ
ロールの選択率は各々86.8%および71.4%であつ
た。
実施例 2〜4
〈パラジウム−銀触媒の調製〉
塩化パラジウム2.5gを濃塩酸6mlに溶解し、
水を加えて全量を15mlとした溶液にヤシガラ活性
炭5gを減圧下に浸漬し、一昼夜放置後70℃に加
熱乾固した。ついで窒素気流中150℃に1時間保
つたのち、水素気流中400℃で3時間パラジウム
を還元した。
一方、硝酸銀0.243gを水15mlに溶解し、この
溶液に上記のパラジウムを担持した触媒を浸漬
し、同様に乾固、乾燥したのち、実施例1と同様
の方法で2.5wt%の硫酸カリウムを担持させた。
次いで水素気流中400℃で3時間還元を行ない、
パラジウム〜銀〜硫酸カリウム触媒を得た。
〈パラジウム−ヒ素触媒の調製〉
塩化パラジウム2.5gを濃塩酸6mlに溶解し、
これにヒ酸0.301gを加え、水を添加して全量を
15mlに希釈し、以下実施例1と同様に乾固、硫酸
カリウムの担持および還元を経てパラジウム〜ヒ
素〜硫酸カリウム触媒を得た。
〈パラジウム−セレン触媒の調製〉
ヒ酸の代わりにセレン酸(40wt%水溶液)
0.819gを使用したこと以外はパラジウム−ヒ素
触媒の調製と同様の方法により、パラジウム〜セ
レン〜硫酸カリウム触媒を調製した。
以上の触媒を使用し、実施例1と同一の条件で
1,2,3−シクロヘキサントリオールの脱水素
反応を行なつて得られた結果を表−1に示す。
The present invention relates to a method for producing pyrogallol by dehydrogenating 1,2,3-cyclohexanetriol. Furthermore, the present inventors discovered a method for obtaining pyrogallol by dehydrogenating 1,2,3-cyclohexanetriol in the presence of a platinum group metal catalyst such as palladium in an inert gas stream, and filed an application (Japanese Patent Application No. −
161097). The present inventor continued to make efforts to further increase the yield of pyrogallol, and as a result, discovered a new catalyst system and arrived at the present invention. A feature of the method of the present invention is that palladium and at least one selected from gold, silver, arsenic, and selenium are used as catalysts in the dehydrogenation reaction of 1,2,3-cyclohexanetriol, and a high yield of pyrogallol is achieved. can get. The present invention will be explained in detail below. The catalyst used is palladium with gold, silver, arsenic, or selenium added, and although there are slight differences in the optimum amount depending on the type of element to be added, The ratio is 2 to 200%, more preferably 5 to 50%. The catalyst is preferably used supported on a carrier. As the carrier, it is preferable to use a carrier that is porous and has a large surface area, such as activated carbon, silica, alumina, etc. Among them, activated carbon is particularly suitable. To prepare the catalyst, palladium and at least one suitable compound selected from gold, silver, arsenic and selenium, such as palladium chloride, palladium nitrate, chloroauric acid, silver acetate, arsenic acid,
A solution of selenic acid or the like is prepared separately or mixed, and the solution is impregnated onto a carrier by an appropriate means such as spraying, and then reduced by a known method such as heating in a hydrogen stream. can be done. Alternatively, it is also possible to prepare a catalyst by first preparing a catalyst on which only palladium is supported, and after reduction, further supporting gold, silver, arsenic, or selenium and performing re-reduction. The amount of palladium supported is 1 to 30
It is preferable to set it to about % by weight. In the method of the present invention, by using a catalyst to which an alkali metal compound is added, the activity can be increased and the yield of pyrogallol can be further improved. Alkali metal compounds include sulfates, carbonates, chlorides of sodium, potassium, rubidium, cesium, etc.
Examples include organic acid salts. These alkali metal compounds can be supported on a carrier by conventional methods such as immersion method and evaporation drying method. There is no particular restriction on the order in which they are carried. The amount of alkali metal compound supported is not particularly limited, but
It is usually selected as appropriate within the range of 0.3 to 30% by weight, preferably 1 to 10% by weight based on the total weight of the catalyst. In the dehydrogenation reaction of 1,2,3-cyclohexanetriol according to the method of the present invention, nitrogen, carbon dioxide,
It is preferable to carry out the reaction under the flow of an inert gas that does not participate in the reaction, such as water vapor or methane. The reaction can be carried out in liquid or gas phase. However, from the viewpoint of separation of the catalyst from the reaction product, it is preferable to carry out the reaction in a gas phase. The reaction temperature is suitably 50 to 500°C, preferably about 150 to 350°C. Although the reaction proceeds even under slightly increased pressure, it is more preferable to carry out the reaction under normal pressure or reduced pressure. Pyrogallol obtained by the method of the present invention is
It can be purified and separated from by-products such as catechol by separation means such as distillation and crystallization. Next, the present invention will be explained in more detail with reference to Examples. Example 1 2.5 g of palladium chloride was dissolved in 6 ml of concentrated hydrochloric acid,
To this was added 0.931 g of chloroauric acid, and water was added to make a total volume of 15 ml. In the aqueous solution, 5 g of coconut shell activated carbon was immersed under reduced pressure, left overnight, and then heated to dryness at 70°C. This material was further immersed in a 10% potassium sulfate aqueous solution for one hour, then evaporated to dryness, and then placed in a nitrogen stream.
After heating at 100°C for 1 hour, the mixture was reduced at 400°C in a hydrogen stream to prepare a palladium/gold/activated carbon catalyst containing 2.5% by weight of potassium sulfate. A glass tube was filled with 0.5 ml of this catalyst, and nitrogen gas was passed through the tube at a GHSV of 5000 hr -1 while heating the tube to 300°C. A 10 wt % aqueous solution of 1,2,3-cyclohexanetriol was passed through the reactor at a LHSV of 2.7 hr -1 to carry out a continuous dehydrogenation reaction at normal pressure. The product was cooled with ice water, separated into gas and liquid, and then analyzed by gas chromatography and high performance liquid chromatography. 1,2,3- at 1 hour after the start of the reaction
The conversion rate of cyclohexanetriol and the selectivity of pyrogallol were 86.8% and 71.4%, respectively. Examples 2 to 4 <Preparation of palladium-silver catalyst> 2.5 g of palladium chloride was dissolved in 6 ml of concentrated hydrochloric acid,
5 g of coconut shell activated carbon was immersed under reduced pressure in a solution made up to 15 ml by adding water, and after being left overnight, it was heated to dryness at 70°C. The mixture was then kept at 150°C in a nitrogen stream for 1 hour, and then the palladium was reduced at 400°C in a hydrogen stream for 3 hours. On the other hand, 0.243 g of silver nitrate was dissolved in 15 ml of water, the above-mentioned palladium-supported catalyst was immersed in this solution, dried, and then 2.5 wt% potassium sulfate was added in the same manner as in Example 1. carried it.
Next, reduction was performed at 400°C for 3 hours in a hydrogen stream,
A palladium-silver-potassium sulfate catalyst was obtained. <Preparation of palladium-arsenic catalyst> Dissolve 2.5 g of palladium chloride in 6 ml of concentrated hydrochloric acid,
Add 0.301g of arsenic acid to this and add water to make up the entire amount.
The mixture was diluted to 15 ml, dried to dryness, supported on potassium sulfate, and reduced in the same manner as in Example 1 to obtain a palladium-arsenic-potassium sulfate catalyst. <Preparation of palladium-selenium catalyst> Selenic acid (40wt% aqueous solution) instead of arsenic acid
A palladium-selenium-potassium sulfate catalyst was prepared in the same manner as the palladium-arsenic catalyst except that 0.819 g was used. Table 1 shows the results obtained by dehydrogenating 1,2,3-cyclohexanetriol using the above catalyst under the same conditions as in Example 1.
【表】
比較例 1
塩化金酸を使用しなかつたこと以外は実施例1
と同様に触媒を調製し、得られたパラジウム〜硫
酸カリウム触媒を使用して実施例1と同一条件で
1,2,3−シクロヘキサントリオールの脱水素
反応を行なつたところ、1,2,3−シクロヘキ
サントリオールの転化率は51.1%、ピロガロール
の選択率は59.2%であつた。[Table] Comparative Example 1 Example 1 except that chloroauric acid was not used
A catalyst was prepared in the same manner as above, and the dehydrogenation reaction of 1,2,3-cyclohexanetriol was carried out under the same conditions as in Example 1 using the obtained palladium-potassium sulfate catalyst. -The conversion rate of cyclohexanetriol was 51.1%, and the selectivity of pyrogallol was 59.2%.
Claims (1)
媒の存在下に脱水素してピロガロールを製造する
方法において、パラジウムならびに金、銀、ヒ素
およびセレンより選ばれる少くとも一種を触媒と
して使用することを特徴とするピロガロールの製
造法。1. A method for producing pyrogallol by dehydrogenating 1,2,3-cyclohexanetriol in the presence of a catalyst, characterized in that at least one member selected from palladium and gold, silver, arsenic and selenium is used as a catalyst. A method for producing pyrogallol.
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP6607380A JPS56161338A (en) | 1980-05-19 | 1980-05-19 | Preparation of pyrogallol |
US06/213,900 US4319054A (en) | 1979-12-12 | 1980-12-08 | Process for producing pyrogallol |
EP80107874A EP0031530B1 (en) | 1979-12-12 | 1980-12-12 | Process for producing pyrogallol |
DE8080107874T DE3067213D1 (en) | 1979-12-12 | 1980-12-12 | Process for producing pyrogallol |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP6607380A JPS56161338A (en) | 1980-05-19 | 1980-05-19 | Preparation of pyrogallol |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS56161338A JPS56161338A (en) | 1981-12-11 |
JPS6261009B2 true JPS6261009B2 (en) | 1987-12-18 |
Family
ID=13305294
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP6607380A Granted JPS56161338A (en) | 1979-12-12 | 1980-05-19 | Preparation of pyrogallol |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS56161338A (en) |
-
1980
- 1980-05-19 JP JP6607380A patent/JPS56161338A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS56161338A (en) | 1981-12-11 |
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