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WO2012133149A1 - Procédé de production directe de peroxyde d'hydrogène au moyen d'un oxyde de titane du type brookite - Google Patents

Procédé de production directe de peroxyde d'hydrogène au moyen d'un oxyde de titane du type brookite Download PDF

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Publication number
WO2012133149A1
WO2012133149A1 PCT/JP2012/057454 JP2012057454W WO2012133149A1 WO 2012133149 A1 WO2012133149 A1 WO 2012133149A1 JP 2012057454 W JP2012057454 W JP 2012057454W WO 2012133149 A1 WO2012133149 A1 WO 2012133149A1
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Prior art keywords
hydrogen peroxide
catalyst
directly producing
producing hydrogen
titanium oxide
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Ceased
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PCT/JP2012/057454
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English (en)
Japanese (ja)
Inventor
石原　達己
常昭 岩切
加藤　賢治
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Kyushu University NUC
Mitsubishi Gas Chemical Co Inc
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Kyushu University NUC
Mitsubishi Gas Chemical Co Inc
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    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B15/00—Peroxides; Peroxyhydrates; Peroxyacids or salts thereof; Superoxides; Ozonides
    • C01B15/01—Hydrogen peroxide
    • C01B15/029—Preparation from hydrogen and oxygen
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
    • B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
    • B01J21/063—Titanium; Oxides or hydroxides thereof
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2235/00—Indexing scheme associated with group B01J35/00, related to the analysis techniques used to determine the catalysts form or properties
    • B01J2235/15—X-ray diffraction
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
    • B01J23/44—Palladium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/48—Silver or gold
    • B01J23/52—Gold
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
    • B01J35/61—Surface area
    • B01J35/613—10-100 m2/g
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/02—Impregnation, coating or precipitation
    • B01J37/0201—Impregnation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
    • B01J23/42—Platinum
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/48—Silver or gold
    • B01J23/50—Silver
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/70—Catalysts, in general, characterised by their form or physical properties characterised by their crystalline properties, e.g. semi-crystalline

Definitions

  • the present invention relates to a method for producing hydrogen peroxide by directly reacting hydrogen and oxygen, and more particularly, a method for producing hydrogen peroxide directly using a catalyst containing brookite-type titanium oxide and a specific active metal. About.
  • hydrogen peroxide Since hydrogen peroxide has an oxidizing power and a strong bleaching and sterilizing action, it is used as a bleaching and sterilizing agent for paper, pulp, fiber, processed fishery products and the like. In addition, it is an important industrial product widely used for oxidation reactions including epoxidation and hydroxylation. Furthermore, hydrogen peroxide is used for surface cleaning in the semiconductor industry, for chemical polishing of copper, tin and other copper alloy surfaces, for etching electronic circuits, and the like. And since hydrogen peroxide is only water and oxygen even if it decomposes, it is positioned as important from the viewpoint of green chemistry, and has attracted attention as an alternative material for chlorine bleach.
  • hydrogen peroxide is produced by an organic method, an anthraquinone method, an electrolysis method or the like, and an anthraquinone method is used as an industrial production method.
  • the anthraquinone method has a number of steps such as reduction, oxidation of the anthraquinone medium, extraction of the generated hydrogen peroxide, purification, concentration, etc., and the capital investment cost is high.
  • There are environmental problems such as use and release of organic solvents into the atmosphere.
  • Patent Document 4 in a method for producing hydrogen peroxide from oxygen and hydrogen under pressure in a sulfuric acid aqueous solution using a platinum group catalyst, by allowing halogen ions such as bromide ions to coexist in the aqueous solution, This shows that high concentration hydrogen peroxide can be selectively produced. That is, in the conventional technique, in order to obtain hydrogen peroxide with a high selectivity in a method for producing hydrogen peroxide with high concentration by catalytically reacting oxygen and hydrogen in a reaction medium, 2 MPa or more. It was necessary to carry out the reaction under high pressure.
  • Patent Document 6 discloses a high concentration peroxidation under low pressure by catalytically reacting oxygen and hydrogen using an aqueous solution as a reaction medium on a catalyst in which titania and a platinum group metal are supported on a carrier that is difficult to crush.
  • a method for producing hydrogen peroxide that makes it possible to obtain hydrogen.
  • Patent Document 7 discloses a suspension obtained by suspending a titanium-containing silicate porous body in a solution (metal salt-containing solution) in which a Pd salt and an Au salt are dissolved, and preparing a suspension.
  • a method for producing a catalyst is described in which a liquid is irradiated with ultraviolet rays to deposit metal fine particles containing an alloy of Pd and Au on the surface of a titanium-containing porous silicate.
  • this method is a method in which a metal is supported on a suspended catalyst by a photoprecipitation method, and the performance of the catalyst is poor because the supported component is not supported in a highly dispersed manner.
  • Patent Document 8 as a method for improving a catalyst for producing direct hydrogen peroxide, a catalyst carrier is acid-washed, and gold and / or palladium, conveniently depositing gold and palladium on the washing carrier at the same time, is used as a catalyst. It is described that the precursor is formed and then the catalyst precursor is preferably heat treated at a temperature of 400 ° C. or higher to form a catalyst comprising gold, palladium or gold and palladium particles. And it is described that silica, titania, alumina, ferric oxide, zeolite or activated carbon is used as a carrier.
  • the production conditions are water / methanol and water / acetone, which are unsuitable for obtaining a purified hydrogen peroxide final product from an industrial standpoint, and the reaction pressure is as high as 1 MPa or more.
  • US Pat. No. 6,057,097 contains at least one metal selected from groups 7 to 11 of the periodic table and is supported on SiO 2 functionalized by acidic groups bonded to the surface of those metals.
  • a catalyst for obtaining hydrogen has been proposed, but the reaction pressure is as high as 9.6 MPa, and further, a reaction in a methanol system, and a purification step is required to obtain a final product.
  • Patent Document 10 proposes a method for producing hydrogen peroxide including a step of reacting hydrogen and oxygen in a solvent in the presence of a cationic polymer containing a noble metal and a halogen-containing anion. It is a reaction in the medium.
  • the present invention has been made based on the background as described above, and can achieve high selectivity and yield even under a low pressure of about 1 atm without using an organic solvent in an aqueous medium.
  • An object is to provide a method capable of producing hydrogen peroxide directly and stably from oxygen.
  • the present inventors have conducted intensive studies on the relationship between the crystal structure of titanium oxide (titania) and the production rate and selectivity of hydrogen peroxide.
  • brookite-type titanium oxide was used as a carrier.
  • Hydrogen peroxide was produced by reacting hydrogen and oxygen in the presence of a catalyst supporting at least one active metal selected from the group consisting of platinum, palladium, silver and gold. The inventors have found that the selectivity and yield are improved in a well-balanced manner and have reached the present invention.
  • ⁇ 1> A step of reacting hydrogen and oxygen in the presence of a catalyst in which at least one active metal selected from the group consisting of platinum, palladium, silver, and gold is supported on brookite-type titanium oxide.
  • This is a direct method for producing hydrogen peroxide.
  • ⁇ 2> The method for directly producing hydrogen peroxide according to ⁇ 1>, wherein the weight of the active metal is 0.01 to 10% by weight with respect to the brookite type titanium oxide.
  • ⁇ 3> The method for directly producing hydrogen peroxide according to ⁇ 1> or ⁇ 2>, wherein the catalyst is hydrogen-reduced at a temperature of 400 ° C. or higher in advance.
  • ⁇ 4> The method for directly producing hydrogen peroxide according to any one of ⁇ 1> to ⁇ 3>, wherein the catalyst is reduced with hydrazine.
  • ⁇ 5> The peroxide according to any one of ⁇ 1> to ⁇ 4>, wherein the catalyst further supports one or more selected from the group consisting of ruthenium, rhodium, iridium, and osmium. This is a direct production method of hydrogen.
  • ⁇ 6> The method for directly producing hydrogen peroxide according to any one of ⁇ 1> to ⁇ 5>, wherein the active metal is palladium and / or gold.
  • ⁇ 7> The method for directly producing hydrogen peroxide according to ⁇ 6>, wherein the active metals are palladium and gold, and the molar ratio of palladium / gold is 0.1 to 10.
  • ⁇ 8> The method for directly producing hydrogen peroxide according to any one of ⁇ 1> to ⁇ 7>, wherein the brookite-type titanium oxide has a specific surface area of at least 50 m 2 / g.
  • ⁇ 9> The method for directly producing hydrogen peroxide according to any one of ⁇ 1> to ⁇ 8>, wherein hydrogen peroxide is produced in the absence of an organic solvent.
  • ⁇ 10> The method for directly producing hydrogen peroxide according to any one of ⁇ 1> to ⁇ 9> above, wherein an inorganic acid selected from hydrogen halide or sulfuric acid is added to the reaction system and reacted.
  • ⁇ 11> The method for directly producing hydrogen peroxide according to ⁇ 10>, wherein the addition amount of the inorganic acid is 0.01 to 10% by weight based on the reaction solution.
  • a brookite type titanium oxide is used as a catalyst carrier, whereby the reaction rate of hydrogen peroxide, The selectivity and yield can be improved in a well-balanced manner, and a highly concentrated aqueous hydrogen peroxide solution can be obtained in a short reaction time.
  • a purification step is not required to obtain a final product.
  • FIG. 1 is a diagram showing an X-ray diffraction of a catalyst obtained in Example 1.
  • FIG. 2 is a diagram showing an X-ray diffraction of a catalyst obtained in Example 2.
  • any brookite type titanium oxide can be used without particular limitation.
  • the specific surface area is important as the catalyst carrier, and the brookite type titanium oxide as the catalyst carrier in the present invention preferably has a large specific surface area, preferably 10 m 2 / g or more, particularly preferably 50 m 2 / g or more. preferable. Further, the upper limit of the specific surface area is preferably 150 m 2 / g or less, and more preferably 100 m 2 / g or less.
  • the catalyst used in the present invention is one in which at least one active metal selected from the group consisting of platinum, palladium, silver and gold is supported on the above brookite type titanium oxide as a carrier.
  • platinum, palladium, silver or gold can be used alone or as a mixture or as an alloy for the active metal.
  • one or more selected from the group consisting of ruthenium, osnium, rhodium and iridium can be used as a mixture or alloy as long as the effects of the present invention are not impaired. .
  • the active metal it is preferable to use palladium and / or gold as the active metal.
  • the molar ratio of palladium / gold varies depending on the dispersion state of the active metal when supported on brookite-type titanium oxide as a carrier, but is preferably 0.1 to 10, and more preferably 1 to 5.
  • the active metal supported on the carrier is preferably 0.01 to 10% by weight, more preferably 0.05 to 5% by weight based on the carrier.
  • the amount of catalyst used is preferably 1 to 100 g / l, more preferably 5 to 40 g / l, based on the reaction solution.
  • a method for supporting the active metal on brookite-type titanium oxide a method in which the titanium oxide is suspended in an aqueous solution in which a metal salt of the active metal is dissolved and then reduced and supported by a reducing agent is also preferably used.
  • a reducing agent oxalic acid, hydrazine or formalin can be used, and hydrazine is preferably used.
  • an inorganic acid to the reaction system for reaction.
  • the amount of inorganic acid added is preferably 0.01 to 10% by weight based on the reaction solution.
  • this inorganic acid application of hydrogen halide or sulfuric acid is preferable, and it is preferable to add either or both of them.
  • the reaction temperature during the synthesis reaction is preferably from 0 to 100 ° C., particularly preferably from 5 to 50 ° C.
  • the pressure of the reaction is not particularly limited, but is preferably atmospheric pressure to 10M Pascal, and particularly preferably atmospheric pressure to 2M Pascal.
  • the reaction time is usually 0.1 to 100 hours, preferably 0.5 to 10 hours. This reaction can be carried out either batchwise or continuously. Further, the flow rates of the hydrogen gas and oxygen gas as raw materials are preferably such that the explosion range is avoided and oxygen is excessive with respect to hydrogen.
  • the hydrogen reaction rate is preferably 30% or more, and more preferably 40% or more.
  • the selectivity for hydrogen peroxide is preferably 40% or more, and more preferably 60% or more.
  • the yield of hydrogen peroxide is preferably 25% or more.
  • Example 1 Showa Denko high surface area brookite type titania (specific surface area 74 m 2 / g) 10 g, HAuCl 4 0.05 g and PdCl 2 0.12 g were suspended in 300 ml of water and heated to 60 ° C. NaOH (2.5 ⁇ 10 ⁇ 4 mol / ml) was added until pH 10 and then a 3% aqueous hydrazine solution was added dropwise. When the color change ceased, the end of the reduction was judged, and the water was removed by heating until it became semi-liquid while stirring with a magnetic stirrer. Further, after removing the magnetic stirrer, the magnetic stirrer was dried overnight in a 85 ° C. dryer.
  • NaOH 2.5 ⁇ 10 ⁇ 4 mol / ml
  • the dried sample was sized to 0.5 to 1.8 mm and subjected to reduction treatment for 4 hours in a H 2 stream at 450 ° C. and 40 ml / min to obtain a black granular catalyst.
  • the obtained catalyst was examined for X-ray diffraction. The result is shown in FIG.
  • Example 2 (Evaporation to dryness method) Showa Denko high surface area brookite type titania (specific surface area 74 m 2 / g) 10 g, HAuCl 4 0.05 g and PdCl 2 0.12 g were suspended in 100 ml of water. While stirring with a magnetic stirrer, the water was removed by heating until it became semi-liquid. Furthermore, after removing the magnetic stirrer, it was dried at 60 ° C. overnight. The dried sample was pulverized, sized to 0.5 to 1.18 mm, and reduced for 4 hours in a H 2 stream at 450 ° C. and 40 ml / min to obtain a black granular catalyst. The obtained catalyst was examined for X-ray diffraction. The result is shown in FIG. Hydrogen peroxide was produced in the same manner as in Example 1 except that the catalyst obtained above was used. The obtained results are shown in Table 1.
  • Example 3 Showa Denko high surface area brookite type titania (specific surface area 74 m 2 / g) 10 g, HAuCl 4 0.086 g and PdCl 2 0.203 g were suspended in 300 ml of water and heated to 60 ° C. NaOH (2.5 ⁇ 10 ⁇ 4 mol / ml) was added until pH 10 and 3% aqueous hydrazine solution was added dropwise. When the color change ceased, the end of the reduction was judged, and the water was removed by heating until it became semi-liquid while stirring with a magnetic stirrer. Further, after removing the magnetic stirrer, the magnetic stirrer was dried overnight in an 85 ° C. dryer. The dried sample was sized to 0.5 to 1.8 mm to obtain a granular catalyst. Hydrogen peroxide was produced in the same manner as in Example 1 except that the catalyst obtained above was used. The obtained results are shown in Table 1.
  • Example 4 Showa Denko high surface area brookite type titania (specific surface area 74 m 2 / g) 10 g and PdCl 2 0.203 g were suspended in 300 ml of water and heated to 60 ° C. NaOH (2.5 ⁇ 10 ⁇ 4 mol / ml) was added until pH 10 and 3% aqueous hydrazine solution was added dropwise. When the color change ceased, the end of the reduction was judged, and the water was removed by heating until it became semi-liquid while stirring with a magnetic stirrer. Further, after removing the magnetic stirrer, the magnetic stirrer was dried overnight in an 85 ° C. dryer. The dried sample was sized to 0.5 to 1.8 mm to obtain a granular catalyst. Hydrogen peroxide was produced in the same manner as in Example 1 except that the catalyst obtained above was used. The obtained results are shown in Table 1.
  • Example 5 Showa Denko high surface area brookite type titania (specific surface area 74m 2 / g) 10g, PdCl 2 0.203g and Pt (NH 3 ) 4 Cl 2 ⁇ H 2 O 0.22g suspended in 300ml water up to 60 ° C Heated. NaOH (2.5 ⁇ 10 ⁇ 4 mol / ml) was added until pH 10 and 3% aqueous hydrazine solution was added dropwise. When the color change ceased, the end of the reduction was judged, and the water was removed by heating until it became semi-liquid while stirring with a magnetic stirrer. Further, after removing the magnetic stirrer, the magnetic stirrer was dried overnight in an 85 ° C. dryer. The dried sample was sized to 0.5 to 1.8 mm to obtain a granular catalyst. Hydrogen peroxide was produced in the same manner as in Example 1 except that the catalyst obtained above was used. The obtained results are shown in Table 1.
  • the dried sample was sized to 0.5 to 1.8 mm and subjected to reduction treatment for 4 hours in a H 2 stream at 450 ° C. and 40 ml / min to obtain a black granular catalyst.
  • Hydrogen peroxide was produced in the same manner as in Example 1 except that the catalyst obtained above was used. The obtained results are shown in Table 1.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Inorganic Chemistry (AREA)
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Abstract

L'invention concerne un procédé de production directe de peroxyde d'hydrogène consistant à faire réagir de l'hydrogène et de l'oxygène en présence d'un catalyseur dans lequel au moins un type de métal actif sélectionné dans le groupe constitué par le platine, le palladium, l'argent et l'or est déposé sur un oxyde de titane du type brookite.
PCT/JP2012/057454 2011-03-30 2012-03-23 Procédé de production directe de peroxyde d'hydrogène au moyen d'un oxyde de titane du type brookite Ceased WO2012133149A1 (fr)

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JP2011074746A JP2014114167A (ja) 2011-03-30 2011-03-30 ブルッカイト型の酸化チタンを用いた過酸化水素の直接製造法
JP2011-074746 2011-03-30

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014010372A1 (fr) * 2012-07-10 2014-01-16 三菱瓦斯化学株式会社 Procédé pour la production de peroxyde d'hydrogène

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111517276B (zh) * 2019-02-02 2021-12-24 国家纳米科学中心 一种光催化分解水制备氢气和双氧水的方法

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JPS5518646B2 (fr) * 1975-12-10 1980-05-20
JP2004518604A (ja) * 2000-12-21 2004-06-24 アルコ　ケミカル　テクノロジィ，　エル．ピー． 過酸化水素の製造方法
JP2009500171A (ja) * 2005-07-11 2009-01-08 ユニバーシティ・カレッジ・カーディフ・コンサルタンツ・リミテッド 触媒の改良
JP2010143810A (ja) * 2008-12-22 2010-07-01 Kyushu Univ イオン性液体を用いた過酸化水素の直接製造法

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Publication number Priority date Publication date Assignee Title
JPS5518646B2 (fr) * 1975-12-10 1980-05-20
JP2004518604A (ja) * 2000-12-21 2004-06-24 アルコ　ケミカル　テクノロジィ，　エル．ピー． 過酸化水素の製造方法
JP2009500171A (ja) * 2005-07-11 2009-01-08 ユニバーシティ・カレッジ・カーディフ・コンサルタンツ・リミテッド 触媒の改良
JP2010143810A (ja) * 2008-12-22 2010-07-01 Kyushu Univ イオン性液体を用いた過酸化水素の直接製造法

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Title
KOHEI MODA ET AL.: "Ti02 Tanji Pd-Au Shokubai ni yoru H2 karano Chokusetsu H202 Gosei", DAI 105 KAI SHOKUBAI TORONKAI TORONKAI A YOKOSHU, 24 March 2010 (2010-03-24), pages 123, XP008176216 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014010372A1 (fr) * 2012-07-10 2014-01-16 三菱瓦斯化学株式会社 Procédé pour la production de peroxyde d'hydrogène
JP2014015353A (ja) * 2012-07-10 2014-01-30 Mitsubishi Gas Chemical Co Inc 過酸化水素の製造方法
US9919923B2 (en) 2012-07-10 2018-03-20 Mitsubishi Gas Chemical Company, Inc. Method for producing hydrogen peroxide

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