WO2022209360A1 - 一酸化炭素を製造する方法、及び一酸化炭素製造装置 - Google Patents
一酸化炭素を製造する方法、及び一酸化炭素製造装置 Download PDFInfo
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- WO2022209360A1 WO2022209360A1 PCT/JP2022/005731 JP2022005731W WO2022209360A1 WO 2022209360 A1 WO2022209360 A1 WO 2022209360A1 JP 2022005731 W JP2022005731 W JP 2022005731W WO 2022209360 A1 WO2022209360 A1 WO 2022209360A1
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- carbon monoxide
- catalyst
- reactor
- group
- base material
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- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 title claims abstract description 49
- 229910002091 carbon monoxide Inorganic materials 0.000 title claims abstract description 48
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 25
- 239000003054 catalyst Substances 0.000 claims abstract description 51
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims abstract description 50
- 150000001875 compounds Chemical class 0.000 claims abstract description 30
- 235000019253 formic acid Nutrition 0.000 claims abstract description 25
- 239000002994 raw material Substances 0.000 claims abstract description 25
- 239000000463 material Substances 0.000 claims abstract description 23
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims abstract description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 24
- 230000002378 acidificating effect Effects 0.000 claims description 19
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- 239000007788 liquid Substances 0.000 claims description 11
- 239000007769 metal material Substances 0.000 claims description 7
- 239000011159 matrix material Substances 0.000 claims description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000000741 silica gel Substances 0.000 claims description 3
- 229910002027 silica gel Inorganic materials 0.000 claims description 3
- TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical compound FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 abstract description 3
- 238000000354 decomposition reaction Methods 0.000 abstract description 3
- 239000007789 gas Substances 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 238000007599 discharging Methods 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000006200 vaporizer Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Images
Classifications
-
- 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
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/02—Sulfur, selenium or tellurium; Compounds thereof
- B01J27/053—Sulfates
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B32/00—Carbon; Compounds thereof
- C01B32/40—Carbon monoxide
Definitions
- the present disclosure relates to a method for producing carbon monoxide and a carbon monoxide production apparatus.
- Formic acid and formic acid alkyl esters generate carbon monoxide by decomposition.
- a method for producing carbon monoxide using formic acid as a raw material for example, a method using a zeolite-based catalyst previously modified with a mineral acid is known (Patent Document 1).
- the present disclosure relates to a novel method for producing carbon monoxide from formic acid or formic acid alkyl ester.
- One aspect of the present disclosure includes a step of generating carbon monoxide by decomposing at least one raw material compound of formic acid or formic acid alkyl ester in the presence of a base material and a catalyst containing an acidic group chemically bonded to the base material. to a method of producing carbon monoxide, including
- Another aspect of the present disclosure relates to a carbon monoxide production apparatus comprising a reactor, and a catalyst disposed in the reactor and containing a base material and acidic groups chemically bonded to the base material.
- carbon monoxide can be efficiently produced.
- the method or apparatus according to one aspect of the present disclosure is advantageous in terms of reaction stability, ease of wastewater treatment, and suppression of equipment corrosion, since acid components are less eluted from the catalyst.
- FIG. 1 is a schematic diagram illustrating one embodiment of a carbon monoxide production apparatus of the present disclosure
- a method for producing carbon monoxide according to the present disclosure comprises: in the presence of a base material and a catalyst containing an acidic group chemically bonded to the base material, monoxide is produced by decomposing at least one raw material compound of formic acid or a formic acid alkyl ester. A step of producing carbon is included.
- the raw material compound can be formic acid, formic acid alkyl ester, or a combination thereof.
- Formic acid alkyl esters may be, for example, methyl formate or ethyl formate.
- the base material that constitutes the catalyst may be porous.
- the matrix may be a non-metallic material, for example a non-metallic material selected from activated carbon, silica gel, and perfluorocarbons.
- a non-metallic material selected from activated carbon, silica gel, and perfluorocarbons.
- the acidic group that constitutes the catalyst may be, for example, a sulfonic acid group, a carboxyl group, a hydroxy group, or a combination thereof, or a sulfonic acid group.
- a sulfonic acid group can be easily introduced into a base material such as a nonmetallic material by chemical bonding.
- a sulfonic acid group ( --SO.sub.3H) may be bonded to the compound species constituting the base material through a single bond.
- the base material that constitutes the catalyst is preferably activated carbon. In this case, the catalytic activity is increased, the reaction efficiency is improved, and the cost can be suppressed.
- the amount of acidic groups in the catalyst may be 0.03 mmol or more per 1 g of the mass of the catalyst containing the base material and acidic groups, or 0.04 mmol or more, or 0.05 mmol or more. There may be.
- the amount of acidic groups in the catalyst may be 1.0 mmol or less, 0.50 mmol or less, or 0.10 mmol or less per gram of catalyst mass.
- a catalyst with an acidic group introduced by chemical bonding can be synthesized by a normal method, and a commercially available catalyst can also be used.
- a reaction that produces carbon monoxide can proceed.
- a carbon monoxide production apparatus having a reactor and a catalyst placed in the reactor may be prepared in advance, and a gas or liquid containing a raw material compound may be supplied into the reactor.
- the raw material compound may be commercially available formic acid or formic acid alkyl ester.
- a gas containing the vapor of the raw material compound may be generated from a solution containing the raw material compound and supplied to the reactor.
- a solution containing the starting compound may be supplied to the reactor. Supplying a gas containing a raw material compound tends to be superior in terms of reaction efficiency.
- the concentration of the raw material compound solution is not particularly limited, but from the viewpoint of energy efficiency, it may be 40% by mass or more based on the mass of the solution.
- the solution of the starting compound may be, for example, an aqueous solution of formic acid.
- the catalyst, raw material compound, or both may be heated.
- the heating temperature is 100 to 300° C.
- the reaction tends to proceed particularly efficiently while suppressing the generation of by-products such as hydrogen.
- the heating temperature may be 100 to 150.degree.
- the reactor can be, for example, a reaction vessel or a reaction tower.
- a gas containing a raw material compound may be continuously supplied to a reaction tower as a reactor in which a catalyst is arranged.
- a continuous supply of gas allows continuous production of carbon monoxide.
- One reaction tower may be used, or a large number of reaction towers may be connected.
- a reactor composed of a large number of reaction towers is advantageous in terms of suppressing uneven flow velocity distribution in the reactor and securing a heat transfer area for heating.
- the gas or liquid containing the catalyst and the starting compound may be placed in a reactor (reaction pot) and then the gas or liquid containing the catalyst and starting compound may be heated.
- the reactor can be made of a non-metallic material such as carbon. Reactors made of non-metallic materials are less susceptible to corrosion by formic acid and carbon monoxide and less likely to affect the reaction. If the heating temperature is relatively low (eg, 100-150° C.), it is easy to apply a reactor with a surface treated with glass lining.
- the reactor When a gas or liquid containing a raw material compound is continuously supplied to a reactor, the reactor usually has an inlet and an outlet for supplying or discharging the gas or liquid, which are connected to an external flow path. be.
- the feed rate of the raw material compound to be supplied is appropriately adjusted according to the amount of acidic groups and the like.
- the feed rate of the raw material compound may be in the range of 0.1 to 1000 [1/hour].
- a method for producing carbon monoxide includes removing unreacted feedstock compounds and by-products from the product (gas or liquid) containing carbon monoxide withdrawn from the reactor, and removing water from the product. and performing.
- Raw compounds and by-products can be removed by conventional washing methods, resulting in high purity carbon monoxide.
- Raw compounds and carbon dioxide can be easily removed by, for example, caustic soda.
- the purity of carbon monoxide in the product after removal of water, raw compounds and by-products by these steps can be 99.99% or higher.
- Such high-purity carbon monoxide can be used in various applications including the semiconductor manufacturing field.
- FIG. 1 is a schematic diagram showing one embodiment of the carbon monoxide production apparatus of the present disclosure.
- the carbon monoxide production apparatus 10 of the present disclosure includes a reactor 1 and a catalyst 2 arranged within the reactor 1 .
- Catalyst 2 includes a matrix and acidic groups chemically bonded to the matrix.
- the reactor 1 also has an inlet 1a and an outlet 1b for supplying or discharging gas or liquid. Outside the reactor 1, the inlet 1a is connected to a channel 3 for supplying at least one raw compound of formic acid or formic acid alkyl ester, and the outlet 1b is connected to a channel 4 for discharging gas or liquid.
- the carbon monoxide production device 10 includes a heating device (not shown) for heating the catalyst 2, the raw material compound or both of them, and a device (not shown) for removing unreacted raw material compounds and by-products from the product containing carbon monoxide. not shown) and may optionally further comprise a device (not shown) for removing water from the product.
- the raw material compound is supplied to the reactor 1 through the inlet 1 a through the flow path 3 and passes through the catalyst 2 . At this time, in the presence of the catalyst, carbon monoxide is produced by decomposition of the raw material compound. Products containing carbon monoxide are discharged from outlet 1 b of reactor 1 through flow path 4 . Carbon monoxide is thus produced.
- Example 1 Activated carbon and a catalyst having a sulfonic acid group chemically bonded to the activated carbon (manufactured by Futamura Chemical, trade name: CE20-96142DH, amount of sulfonic acid group: 0.05 to 0.10 mmol per gram of catalyst (including activated carbon and sulfonic acid group) ) was prepared. 25 g of this catalyst was packed in a column having an inner diameter of 2.5 cm and a length of 25 cm. While the column packed with the catalyst was externally heated to 140° C., 6 g of formic acid vapor at 120° C. generated by passing a formic acid aqueous solution with a concentration of 76% by weight through a vaporizer was supplied from one end of the column.
- a catalyst having a sulfonic acid group chemically bonded to the activated carbon manufactured by Futamura Chemical, trade name: CE20-96142DH, amount of sulfonic acid group: 0.05 to 0.10 mmol per gram of catalyst
- the gas discharged from the other end of the column was passed through an aqueous caustic soda solution with a concentration of 20% by weight and then water in that order.
- a caustic soda aqueous solution removed trace amounts of carbon dioxide contained in the gas.
- the amount of hydrogen in the gas is quantified by gas chromatography equipped with a PDD (Pulsed Discharge Detector) as a detector. From the flow rate, the conversion of formic acid and the selectivity to carbon monoxide were determined. The conversion was 21% and the selectivity to carbon monoxide was greater than 99.99%.
- Comparative example 1 A column having a length of 10 cm was filled with 22 g (50 mL) of granular activated carbon having no sulfonic acid group (manufactured by Takeda Pharmaceutical Co., Ltd., trade name: Shirasagi G2X). A carbon monoxide production test was conducted in the same manner as in Example 1, except that this packed column was used. Analysis of the gas discharged from the column confirmed that no carbon monoxide was produced.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Carbon And Carbon Compounds (AREA)
- Catalysts (AREA)
Abstract
Description
活性炭及び活性炭に化学結合したスルホン酸基を有する触媒(フタムラ化学製、商品名:CE20-96142DH、スルホン酸基の量:触媒(活性炭及びスルホン酸基を含む)1g当たり0.05~0.10mmol)を準備した。この触媒25gを内径2.5cm、長さ25cmのカラムに充填した。触媒が充填されたカラムを外部から140℃に加熱しながら、カラムの一方の端部から、濃度76重量%の蟻酸水溶液が気化器を通過することによって生成した120℃の蟻酸の蒸気を、6g/時間の供給速度で送り込んだ。カラムの他方の端部から排出されたガスを、濃度20重量%の苛性ソーダ水溶液、及び水の順で通過させた。苛性ソーダ水溶液によって、ガス中に含まれる微量の二酸化炭素が除去された。苛性ソーダ水溶液及び水を通過したガスを冷却及び乾燥してから、ガス中の水素量を、検出器としてPDD(Pulsed Discharge Detector)を備えたガスクロマトグラフィーによって定量し、求められた水素量及びガスの流量から、蟻酸の転化率と一酸化炭素への選択率を求めた。転化率は21%で、一酸化炭素への選択率は99.99%以上であった。
長さ10cmのカラムに、スルホン酸基を有しない粒状の活性炭(武田薬品工業製、商品名:白鷺G2X)22g(50mL)を充填した。この充填されたカラムを用いたこと以外は実施例1と同様にして、一酸化炭素の生成試験を行った。カラムから排出されたガスの分析の結果、一酸化炭素が生成しないことが確認された。
Claims (14)
- 母材及び該母材に化学結合した酸性基を含む触媒の存在下で、蟻酸又は蟻酸アルキルエステルのうち少なくとも一方の原料化合物の分解によって一酸化炭素を生成させる工程を含む、一酸化炭素を製造する方法。
- 前記酸性基がスルホン酸基である、請求項1に記載の方法。
- 前記母材が、非金属材料である、請求項1又は2に記載の方法。
- 前記非金属材料が、活性炭、シリカゲル、及びパーフルオロカーボンからなる群より選ばれる少なくとも1種を含む、請求項3に記載の方法。
- 前記触媒における前記酸性基の量が、前記触媒の質量1g当たり0.03mmol以上である、請求項1~4のいずれか一項に記載の方法。
- 前記触媒における前記酸性基の量が、前記触媒の質量1g当たり1.0mmol以下である、請求項1~5のいずれか一項に記載の方法。
- 前記原料化合物の分解によって一酸化炭素を生成させる工程において、前記触媒が100~300℃に加熱される、請求項1~6のいずれか一項に記載の方法。
- 前記触媒が反応器内に配置され、前記反応器に前記原料化合物を含むガス又は液体が供給される、請求項1~7のいずれか一項に記載の方法。
- 反応器と、
前記反応器内に配置された、母材及び該母材に化学結合した酸性基を含む触媒と、
を備える、一酸化炭素製造装置。 - 前記酸性基がスルホン酸基である、請求項9に記載の一酸化炭素製造装置。
- 前記母材が、非金属材料である、請求項9又は10に記載の一酸化炭素製造装置。
- 前記非金属材料が、活性炭、シリカゲル、及びパーフルオロカーボンからなる群より選ばれる少なくとも1種を含む、請求項11に記載の一酸化炭素製造装置。
- 前記触媒における前記酸性基の量が、前記触媒の質量1g当たり0.03mmol以上である、請求項9~12のいずれか一項に記載の一酸化炭素製造装置。
- 前記触媒における前記酸性基の量が、前記触媒の質量1g当たり1.0mmol以下である、請求項9~13のいずれか一項に記載の一酸化炭素製造装置。
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Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH107413A (ja) * | 1996-06-18 | 1998-01-13 | Sumitomo Seika Chem Co Ltd | 高純度一酸化炭素の製造方法 |
JP2002173302A (ja) * | 2000-12-04 | 2002-06-21 | Mitsubishi Gas Chem Co Inc | 一酸化炭素および水素の混合ガスの製造方法 |
KR101851606B1 (ko) * | 2016-11-10 | 2018-04-24 | 충북대학교 산학협력단 | 개미산 분해반응을 통해 고순도 일산화탄소를 제조하기 위한 HPW/TiO2 촉매 및 이의 제조방법 |
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- 2022-02-14 WO PCT/JP2022/005731 patent/WO2022209360A1/ja active Application Filing
- 2022-02-14 KR KR1020237037103A patent/KR20230162680A/ko unknown
- 2022-02-14 JP JP2023510613A patent/JPWO2022209360A1/ja active Pending
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH107413A (ja) * | 1996-06-18 | 1998-01-13 | Sumitomo Seika Chem Co Ltd | 高純度一酸化炭素の製造方法 |
JP2002173302A (ja) * | 2000-12-04 | 2002-06-21 | Mitsubishi Gas Chem Co Inc | 一酸化炭素および水素の混合ガスの製造方法 |
KR101851606B1 (ko) * | 2016-11-10 | 2018-04-24 | 충북대학교 산학협력단 | 개미산 분해반응을 통해 고순도 일산화탄소를 제조하기 위한 HPW/TiO2 촉매 및 이의 제조방법 |
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