JPS6261010B2 - - Google Patents
Info
- Publication number
- JPS6261010B2 JPS6261010B2 JP8194680A JP8194680A JPS6261010B2 JP S6261010 B2 JPS6261010 B2 JP S6261010B2 JP 8194680 A JP8194680 A JP 8194680A JP 8194680 A JP8194680 A JP 8194680A JP S6261010 B2 JPS6261010 B2 JP S6261010B2
- Authority
- JP
- Japan
- Prior art keywords
- cyclohexanetriol
- reaction
- pyrogallol
- dehydrogenation
- palladium
- 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
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 claims description 28
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 22
- IZSANPWSFUSNMY-UHFFFAOYSA-N cyclohexane-1,2,3-triol Chemical compound OC1CCCC(O)C1O IZSANPWSFUSNMY-UHFFFAOYSA-N 0.000 claims description 14
- 229940079877 pyrogallol Drugs 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 12
- 229910052763 palladium Inorganic materials 0.000 claims description 11
- 229910052714 tellurium Inorganic materials 0.000 claims description 7
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 claims description 7
- 239000011261 inert gas Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 description 15
- 238000006356 dehydrogenation reaction Methods 0.000 description 12
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- PFURGBBHAOXLIO-UHFFFAOYSA-N cyclohexane-1,2-diol Chemical compound OC1CCCCC1O PFURGBBHAOXLIO-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 150000001339 alkali metal compounds Chemical class 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 229910001873 dinitrogen Inorganic materials 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 101100010166 Mus musculus Dok3 gene Proteins 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- FNTHQRXVZDCWSP-UHFFFAOYSA-N cyclohexane-1,1,2-triol Chemical class OC1CCCCC1(O)O FNTHQRXVZDCWSP-UHFFFAOYSA-N 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical group OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- JQPFYXFVUKHERX-UHFFFAOYSA-N 2-hydroxy-2-cyclohexen-1-one Natural products OC1=CCCCC1=O JQPFYXFVUKHERX-UHFFFAOYSA-N 0.000 description 1
- NTUQPJNKERXQPA-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-5-ol Chemical compound OC1CCCC2OC12 NTUQPJNKERXQPA-UHFFFAOYSA-N 0.000 description 1
- 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
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 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
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000001649 bromium compounds Chemical class 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
- 238000001354 calcination Methods 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 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
- OILAIQUEIWYQPH-UHFFFAOYSA-N cyclohexane-1,2-dione Chemical compound O=C1CCCCC1=O OILAIQUEIWYQPH-UHFFFAOYSA-N 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical class OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229940074391 gallic acid Drugs 0.000 description 1
- 235000004515 gallic acid Nutrition 0.000 description 1
- 230000000887 hydrating effect Effects 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000035484 reaction time Effects 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
- 238000000926 separation method Methods 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】
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。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing pyrogallol by dehydrogenating 1,2,3-cyclohexanetriol.
ピロガロールは生理活性物質等の有機合成中間
体として極めて有用な化合物であるが、現在は天
然物から抽出した没食子酸の熱分解により製造さ
れ、高価であるために利用の途に制限を受けてい
る。 Pyrogallol is an extremely useful compound as an intermediate for organic synthesis of physiologically active substances, etc., but currently it is produced by thermal decomposition of gallic acid extracted from natural products, and its use is limited due to its high price. .
シクロヘキサノール類の脱水素によりフエノー
ル類を製造する方法についてはよく知られてお
り、たとえばDokl.Akad.Nank.SSSR185，145
（1969）には１，２−シクロヘキサンジオールの
脱水素によるカテコールの製造法が、Dokl.
Akad.Nank.SSSR，198，1354（1971）には１，
２，３−シクロヘキサントリオールの脱水素によ
るピロガロールの製造法が記載されている。いず
れの方法においても、触媒としては活性炭にパラ
ジウムおよび炭酸カリウムを担持したものが使用
され、水素気流中で300℃の温度条件下に気相脱
水素を行なつている。 Methods for producing phenols by dehydrogenation of cyclohexanols are well known; for example, Dokl.Akad.Nank.SSSR 185 , 145
(1969) described a method for producing catechol by dehydrogenation of 1,2-cyclohexanediol, as described by Dokl.
1 in Akad.Nank.SSSR, 198 , 1354 (1971),
A process for the preparation of pyrogallol by dehydrogenation of 2,3-cyclohexanetriol is described. In both methods, a catalyst in which palladium and potassium carbonate are supported on activated carbon is used, and gas phase dehydrogenation is carried out at a temperature of 300° C. in a hydrogen stream.
本発明者らは上記文献に記載された反応を追試
したところ１，２−シクロヘキサンジオールの脱
水素反応においてはほぼ同様の結果が得られる
が、１，２，３−シクロヘキサントリオールの脱
水素反応においては主生成物として得られるのは
カテコールであり、ピロガロールの選択率は非常
に小さかつた。本発明者らは１，２，３−シクロ
ヘキサントリオールの脱水素反応においてピロガ
ロールの選択率を高めるために種々検討した結
果、パラジウムおよびテルルを含有する触媒の存
在下に、１，２，３−シクロヘキサントリオール
を窒素ガスなどの不活性気流中で脱水素するとピ
ロガロールの選択率が飛躍的に高くなることを見
い出し、本発明に到達したものである。すなわ
ち、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にあ
たり、該反応を、パラジウムおよびテルルを含有
する触媒の存在下に不活性気流中で行なうことが
特徴であり、１，２−シクロヘキサンジオールの
脱水素反応が、水素気流中で行なつても不活性気
流中で行なつても殆ど選択性は変わらない反応で
あるのとは対称的に本発明方法ではピロガロール
の選択率が数倍にも向上する。 The present inventors conducted a follow-up experiment on the reaction described in the above literature, and found that almost the same results were obtained in the dehydrogenation reaction of 1,2-cyclohexanediol, but in the dehydrogenation reaction of 1,2,3-cyclohexanetriol. The main product obtained was catechol, and the selectivity for pyrogallol was very small. The present inventors conducted various studies to increase the selectivity of pyrogallol in the dehydrogenation reaction of 1,2,3-cyclohexanetriol. The present invention was achieved based on the discovery that the selectivity of pyrogallol increases dramatically when triol is dehydrogenated in an inert gas stream such as nitrogen gas. That is, the present invention is characterized in that, in producing pyrogallol by dehydrogenating 1,2,3-cyclohexanetriol, the reaction is carried out in the presence of a catalyst containing palladium and tellurium in an inert gas stream. In contrast to the dehydrogenation reaction of 1,2-cyclohexanediol, which has almost no difference in selectivity whether it is carried out in a hydrogen stream or in an inert gas stream, the method of the present invention The selectivity of pyrogallol is improved several times.
以下に本発明を詳細に説明する。 The present invention will be explained in detail below.
本発明方法における原料である１，２，３−シ
クロヘキサントリオールは公知の方法で製造され
る。たとえば、シクロヘキセンを酸化して得られ
る１，２−エポキシシクロヘキサン−３−オール
を水和することにより製造される。１，２，３−
シクロヘキサントリオールにはその立体構造の相
違により３種類の異性体が存在するが、本発明方
法においてはそのいずれをも使用することができ
る。１，２，３−シクロヘキサントリオールはそ
のままあるいは水などの溶媒に溶解して反応系に
供給される。 1,2,3-cyclohexanetriol, which is a raw material in the method of the present invention, is produced by a known method. For example, it is produced by hydrating 1,2-epoxycyclohexan-3-ol obtained by oxidizing cyclohexene. 1, 2, 3-
There are three types of isomers of cyclohexanetriol due to differences in their steric structures, and any of them can be used in the method of the present invention. 1,2,3-cyclohexanetriol is supplied to the reaction system as it is or dissolved in a solvent such as water.
触媒としては、パラジウムおよびパラジウム１
グラム原子に対して0.02〜２グラム原子、好まし
くは0.05〜0.5グラム原子のテルルを含有する触
媒が使用される。これらの金属は、好ましくは、
活性炭、シリカ、アルミナ、シリコンカーバイド
等の担体に担持して使用される。担体へのパラジ
ウムおよびテルルの担持はこれらの金属の化合物
の水溶液中に担体を浸漬したのち焼成し次いで水
素気流中で還元する方法などの公知の方法で行な
うことができる。パラジウムの担持量は１〜50重
量％程度とすることが好ましい。本発明方法にお
いては、パラジウムおよびテルルにさらにアルカ
リ金属化合物を添加した触媒を使用することによ
り、ピロガロールの選択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、硝酸塩、臭化物、塩化物、有機酸
が一例として挙げられる。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、吸着法あるいは噴霧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、テルルおよ
びアルカリ金属化合物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。 As a catalyst, palladium and palladium 1
Catalysts containing 0.02 to 2 gram atoms, preferably 0.05 to 0.5 gram atoms of tellurium per gram atom are used. These metals are preferably
It is used supported on a carrier such as activated carbon, silica, alumina, or silicon carbide. Palladium and tellurium can be supported on the carrier by a known method such as immersing the carrier in an aqueous solution of a compound of these metals, calcining it, and then reducing it in a hydrogen stream. The amount of palladium supported is preferably about 1 to 50% by weight. In the method of the present invention, the selectivity of pyrogallol can be further improved by using a catalyst in which an alkali metal compound is further added to palladium and tellurium. Examples of alkali metal compounds include sulfates, carbonates, nitrates, bromides, chlorides, and organic acids such as sodium, potassium, rubidium, and cesium. These alkali metal compounds can be supported on a carrier by conventional methods such as dipping, evaporation to dryness, adsorption, or spraying. is not particularly limited. The amount of the alkali metal compound supported is not particularly limited, but is usually 0.3 to 30% by weight, preferably 1 to 30% by weight based on the total weight of the catalyst.
It is appropriately selected within the range of 10% by weight.
本発明による１，２，３−シクロヘキサントリ
オールの脱水素反応は、窒素、アルゴン、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100〜500℃、好ましくは150
〜350℃の温度条件下、常圧ないしは減圧下で行
なわれる。上記反応は液相でも気相でも行ない得
るが、通常の温度、圧力条件では気相で行なわ
れ、また、触媒成分の一つであるアルカリ金属化
合物の溶出を防止するためにも気相で行なうこと
が好ましい。また、反応系に水を存在させること
により触媒寿命を延長することができるので、原
料の１，２，３−シクロヘキサントリオールを水
に溶解して反応系に供給することは非常に好まし
い実施態様である。 The dehydrogenation reaction of 1,2,3-cyclohexanetriol according to the present invention is carried out at 100 to 500°C, preferably at 150°C while flowing an inert gas that does not participate in the reaction, such as nitrogen, argon, carbon dioxide, water vapor, or methane.
It is carried out at a temperature of ~350°C under normal pressure or reduced pressure. The above reaction can be carried out in a liquid phase or a gas phase, but under normal temperature and pressure conditions it is carried out in a gas phase, and also in order to prevent the elution of the alkali metal compound, which is one of the catalyst components. It is preferable. Furthermore, since the presence of water in the reaction system can extend the life of the catalyst, it is a very preferred embodiment to dissolve the raw material 1,2,3-cyclohexanetriol in water and supply it to the reaction system. be.
本発明方法においては、ピロガロールとともに
カテコール、１，２シクロヘキサンジオン等が副
生するが、蒸留、晶析などの公知の分離手段でそ
れぞれを分離取得することができる。 In the method of the present invention, catechol, 1,2 cyclohexanedione, etc. are produced as by-products along with pyrogallol, but each can be separated and obtained by known separation means such as distillation and crystallization.
次に本発明を実施例により更に具体的に説明す
る。 Next, the present invention will be explained in more detail with reference to Examples.
実施例 １
パラジウム、テルルおよび硫酸カリウムをそれ
ぞれ3.0wt％、5.8wt％および2.5wt％含有する活
性炭担持脱水素触媒１mlを反応管に充填して300
℃に加熱し、窒素ガスをGHSV2900hr-1で、10wt
％、１，２，３−シクロヘキサントリオール水溶
液をLHSV2.5hr-1で流通させ、脱水素反応を行な
つた。反応開始後６時間を経過した時点における
１，２，３−シクロヘキサントリオールの転化率
は99.3％であり、ピロガロールおよびカテコール
の選択率はそれぞれ55.9％および41.6％であつ
た。Example 1 A reaction tube was charged with 1 ml of an activated carbon-supported dehydrogenation catalyst containing 3.0 wt%, 5.8 wt%, and 2.5 wt% of palladium, tellurium, and potassium sulfate, respectively.
Heated to ℃, nitrogen gas GHSV2900hr -1 , 10wt
%, 1,2,3-cyclohexanetriol aqueous solution was passed through at LHSV 2.5 hr -1 to perform a dehydrogenation reaction. The conversion rate of 1,2,3-cyclohexanetriol at 6 hours after the start of the reaction was 99.3%, and the selectivity of pyrogallol and catechol were 55.9% and 41.6%, respectively.
比較例 １
パラジウム1.5wt％および炭酸カリウム4wt％
を含有する活性炭触媒を使用し、水素ガスを
GHSV5000hr-1で流通させ、10wt％１，２，３−
シクロヘキサントリオール水溶液のLHSVを
2.2hr-1に変更したこと以外は実施例１と同様に
反応を行なつた。その結果、１，２，３−シクロ
ヘキサントリオールの転化率は100％であつた
が、ピロガロールの選択率は僅か4.8％で、主生
成物はカテコールであつた。Comparative example 1 Palladium 1.5wt% and potassium carbonate 4wt%
hydrogen gas using an activated carbon catalyst containing
Distributed at GHSV5000hr -1 , 10wt%1,2,3-
LHSV of cyclohexanetriol aqueous solution
The reaction was carried out in the same manner as in Example 1 except that the reaction time was changed to 2.2 hr -1 . As a result, the conversion rate of 1,2,3-cyclohexanetriol was 100%, but the selectivity of pyrogallol was only 4.8%, and the main product was catechol.
実施例 ２
パラジウムおよびテルルをそれぞれ3.0wt％お
よび5.8wt％含有する活性炭担持脱水素触媒0.5ml
を使用し、窒素ガスのGHSVを9000hr-1に、10wt
％１，２，３−シクロヘキサントリオール水溶液
のLHSVを55hr-1に変更したこと以外は実施例１
と同様に反応を行なつた。その結果反応開始後１
時間を経過した時点における１，２，３−シクロ
ヘキサントリオールの転化率は56.3％、ピロガロ
ールの選択率は38.0％であつた。Example 2 0.5ml of activated carbon-supported dehydrogenation catalyst containing 3.0wt% and 5.8wt% of palladium and tellurium, respectively
using nitrogen gas GHSV of 9000hr -1 , 10wt
Example 1 except that the LHSV of the 1,2,3-cyclohexanetriol aqueous solution was changed to 55 hr -1
The reaction was carried out in the same manner. As a result, after the start of the reaction 1
At the time point, the conversion rate of 1,2,3-cyclohexanetriol was 56.3%, and the selectivity of pyrogallol was 38.0%.
Claims (1)
在下に、１，２，３−シクロヘキサントリオール
を不活性気流中で脱水素することを特徴とするピ
ロガロールの製造方法。1. A method for producing pyrogallol, which comprises dehydrogenating 1,2,3-cyclohexanetriol in an inert gas stream in the presence of a catalyst containing palladium and tellurium.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8194680A JPS577430A (en) | 1980-06-17 | 1980-06-17 | 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 |
|---|---|---|---|
| JP8194680A JPS577430A (en) | 1980-06-17 | 1980-06-17 | Preparation of pyrogallol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS577430A JPS577430A (en) | 1982-01-14 |
| JPS6261010B2 true JPS6261010B2 (en) | 1987-12-18 |
Family
ID=13760662
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8194680A Granted JPS577430A (en) | 1979-12-12 | 1980-06-17 | Preparation of pyrogallol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS577430A (en) |
-
1980
- 1980-06-17 JP JP8194680A patent/JPS577430A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS577430A (en) | 1982-01-14 |
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