JP2021521331A - ヒドロホルミル化反応に使用する合成ガスを生成するための方法 - Google Patents
ヒドロホルミル化反応に使用する合成ガスを生成するための方法 Download PDFInfo
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- 238000007037 hydroformylation reaction Methods 0.000 title claims abstract description 34
- 238000000034 method Methods 0.000 title claims description 30
- 239000007789 gas Substances 0.000 claims abstract description 79
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 49
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 45
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 38
- 238000006243 chemical reaction Methods 0.000 claims abstract description 29
- 239000001257 hydrogen Substances 0.000 claims abstract description 27
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 26
- 239000007788 liquid Substances 0.000 claims abstract description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000000203 mixture Substances 0.000 claims abstract description 16
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000004519 manufacturing process Methods 0.000 claims abstract description 14
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 13
- 239000007787 solid Substances 0.000 claims abstract description 13
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 9
- 238000001816 cooling Methods 0.000 claims abstract description 9
- 239000002994 raw material Substances 0.000 claims abstract description 8
- 239000007791 liquid phase Substances 0.000 claims abstract description 5
- 238000001704 evaporation Methods 0.000 claims abstract description 3
- 239000000376 reactant Substances 0.000 claims abstract description 3
- 238000005868 electrolysis reaction Methods 0.000 claims description 19
- 239000000463 material Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 description 17
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 11
- 230000008901 benefit Effects 0.000 description 11
- 239000001301 oxygen Substances 0.000 description 11
- 150000001336 alkenes Chemical class 0.000 description 8
- 238000001035 drying Methods 0.000 description 5
- 239000000446 fuel Substances 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000003889 chemical engineering Methods 0.000 description 3
- 238000002309 gasification Methods 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- -1 diols) Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- MWRWFPQBGSZWNV-UHFFFAOYSA-N Dinitrosopentamethylenetetramine Chemical compound C1N2CN(N=O)CN1CN(N=O)C2 MWRWFPQBGSZWNV-UHFFFAOYSA-N 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 229940112112 capex Drugs 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 239000003575 carbonaceous material Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000005810 carbonylation reaction Methods 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000002848 electrochemical method Methods 0.000 description 1
- 238000003487 electrochemical reaction Methods 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- FEBLZLNTKCEFIT-VSXGLTOVSA-N fluocinolone acetonide Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O FEBLZLNTKCEFIT-VSXGLTOVSA-N 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 239000002737 fuel gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000000629 steam reforming Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 231100000925 very toxic Toxicity 0.000 description 1
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Abstract
Description
CO2+H2<−>CO+H2O
反応に使用される水素は、固体酸化物電解セル(SOEC)またはSOECスタックを用いて水蒸気から生成することができる。本発明によれば、H2は、SOECまたはSOECスタック内の水蒸気から、典型的には700℃に近い高温で生成される。SOECまたはSOECスタックからの排出ガスは、SOECの作動温度に近い温度でH2およびH2Oを含む。この排出ガスはCO2と共に直接的にRWGS反応器に導かれることができる。RWGS反応器は、典型的には加熱反応器であるが、断熱反応器でもよい。RWGS反応器においては、上記のRWGS反応が進行する。RWGS反応は平衡限界であるため、RWGS反応器からの排出ガスにはH2、CO、H2OおよびCO2が含まれる。大部分の水蒸気が液体水として凝縮するまで、排出ガスを冷却することによって水を除去する。ガスのさらなる乾燥は、例えば乾燥カラムを使用することによって達成され得る。CO2は圧力スイング吸着装置などを用いて除去することができるが、そのような装置は非常に高価である。本発明によれば、CO2はヒドロホルミル化反応後まで除去されない。これは費用の節約となり、付加的な利点を提示する。
H2O(カソード)→H2(カソード)+1/2O2(アノード)(1)
H2+CO2<−>H2O+CO (2)
−セルまたはセルスタックが作動するのに十分な温度において、固体酸化物電解セル(SOEC)またはSOECスタックへ水蒸気を供給する一方で、前記セルまたはセルスタックに電流を供給して、水蒸気の水素への部分的な変換を行う工程、
−任意選択で、原料ガス流を冷却することによって、水蒸気の少なくとも一部を液体水として凝縮させ、残った生成物ガスをこの液体から分離することによって、残った水蒸気の一部または全部を原料ガス流から除去する工程、
−RWGS反応が起こるRWGS反応器のための供給材料として、
外部源からのCO2と共にH2を含む排出SOECガスを利用し、CO2およびH2の一部をCOおよびH2Oに変換する工程、
−原料ガス流を冷却することによって、水蒸気の少なくとも一部を液体水として凝縮させ、残った生成物ガスをこの液体から分離することによって、残った水蒸気の一部または全部を原料ガス流から除去する工程、
および
−RWGS反応器へとCO2を再利用しながら、反応物として一酸化炭素および水素を利用する液相ヒドロホルミル化のためにCO、CO2およびH2を含む前記ガス混合物を使用する工程。
実施例1
H2O電気分解
75個のセルからなるSOECスタックを、50Aの電解電流を加えながら、流速100Nl/分の水蒸気(約80g/分の液体水流速に相当する)でカソードに供給しながら、平均700℃で作動する。上記の式(4)に基づいて、このような条件下でのHOの変換は26%である。すなわち、スタックのカソード面から出るガスは、26%のH2Oと74%のH2から成る。
RWGSを組み合わせたH2O電解
75セルから成るSOECスタックを、50Aの電解電流を加えながら蒸気を全流量100Nl/minでカソードに供給しながら、平均温度700°Cで作動させた。スタックにおいては、水蒸気は52%の変換で反応(1)に従って電気化学的にH2に変換される。この排出ガスは100Nl/分のCO2とともに、SOECから直接的にRWGS反応器に供給される。したがって、H2のO/CO2供給率は50:50になる。RWGS反応器に供給されるガスは、0%CO、50%CO2、26%H2および24%H2Oの構成となる。RWGS反応により、水素の一部がCOの生成に使用される。RWGS反応器は700℃で等温で作動する。したがって、RWGS反応器から出るガスの構成は、10.7%CO、39.3%CO2、15.3%H2、および34.7%Oである。生成物ガスのCO:H2の比率は1:1.43である。
RWGSを組み合わせたH2O電解
この例は、総H2O/CO2供給率が41:59であることを除いて、例2と同様に実施される。RWGS反応器から出るガスの構成は、13.2%CO、45.8%CO2、13.0%H2および28.0%Oである。生成物ガスのCO:H2の比率は約1:1である。
RWGSを組み合わせたH2O電解
この例は、SOECスタックからの排出カソードガスを冷却することにより、水蒸気が濃縮され液状の水とされ、分離器で取り出されることを除いて、実施例2と同様に実施される。したがって、RWGS反応器に供給されるガスは、0%CO、50%CO2、50%H2および0%H2Oの概算構成となる。RWGS反応のため、水素の一部を用いてCOを発生させた。RWGS反応器を700℃で等温で作動させる。したがって、RWGS反応器から出るガスの概算組成は、22%CO、28%CO2、28%H2、22%H2Oである。したがって、生成物ガスのCO:H2の比率は1:1.27になる。
Claims (2)
- ヒドロホルミル化プラントに使用するための一酸化炭素、二酸化炭素および水素を含むガス混合物の生成方法であって、以下の工程:
−水を蒸発させ水蒸気とする工程、
−セルまたはセルスタックが作動するのに十分な温度において、固体酸化物電解セル(SOEC)またはSOECスタックへ水蒸気を供給する一方で、前記セルまたはセルスタックに電流を供給して、水蒸気の水素への部分的な変換を行う工程、
−任意選択で、原料ガス流を冷却することによって、水蒸気の少なくとも一部を液体水として凝縮させ、残った生成物ガスをこの液体から分離することによって、残った水蒸気の一部または全部を原料ガス流から除去する工程、
−RWGS反応が起こる逆水ガスシフト(RWGS)反応器のための供給材料として、
外部源からのCO2と共にH2を含む排出SOECガスを利用し、CO2およびH2の一部をCOおよびH2Oに変換する工程、
−原料ガス流を冷却することによって、水蒸気の少なくとも一部を液体水として凝縮させ、残った生成物ガスをこの液体から分離することによって、残った水蒸気の一部または全部を原料ガス流から除去する工程、
および
−RWGS反応器へとCO2を再利用しながら、反応物として一酸化炭素および水素を利用する液相ヒドロホルミル化のためにCO、CO2およびH2を含む前記ガス混合物を使用する工程
を含む前記方法。 - SOECまたはSOECスタック中のH2Oの電解によりH2が生成される温度が、700℃付近である、請求項1に記載の方法。
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