JP5046214B2 - 1−ブテンを酸化的脱水素化して1,3−ブタジエンを製造するためのビスマス・モリブデン・鉄の複合酸化物触媒及びその製造方法 - Google Patents
1−ブテンを酸化的脱水素化して1,3−ブタジエンを製造するためのビスマス・モリブデン・鉄の複合酸化物触媒及びその製造方法 Download PDFInfo
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- JP5046214B2 JP5046214B2 JP2009240253A JP2009240253A JP5046214B2 JP 5046214 B2 JP5046214 B2 JP 5046214B2 JP 2009240253 A JP2009240253 A JP 2009240253A JP 2009240253 A JP2009240253 A JP 2009240253A JP 5046214 B2 JP5046214 B2 JP 5046214B2
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- bismuth
- catalyst
- molybdenum
- butadiene
- iron
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- 239000003054 catalyst Substances 0.000 title claims description 99
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 title claims description 80
- 238000004519 manufacturing process Methods 0.000 title claims description 20
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 title description 47
- 238000005839 oxidative dehydrogenation reaction Methods 0.000 title description 24
- DTDQFVRSJWCWNK-UHFFFAOYSA-N [Fe].[Bi].[Mo] Chemical compound [Fe].[Bi].[Mo] DTDQFVRSJWCWNK-UHFFFAOYSA-N 0.000 title description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 73
- 229910052797 bismuth Inorganic materials 0.000 claims description 38
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 35
- 229910052750 molybdenum Inorganic materials 0.000 claims description 34
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 32
- 229910052742 iron Inorganic materials 0.000 claims description 32
- 239000011733 molybdenum Substances 0.000 claims description 32
- 239000002131 composite material Substances 0.000 claims description 30
- 229910044991 metal oxide Inorganic materials 0.000 claims description 24
- 150000004706 metal oxides Chemical class 0.000 claims description 24
- 239000000243 solution Substances 0.000 claims description 19
- 239000011259 mixed solution Substances 0.000 claims description 15
- 239000002243 precursor Substances 0.000 claims description 9
- 239000000047 product Substances 0.000 claims description 5
- 239000012692 Fe precursor Substances 0.000 claims description 4
- 239000003637 basic solution Substances 0.000 claims description 3
- 238000001027 hydrothermal synthesis Methods 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 36
- 230000000694 effects Effects 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 238000000034 method Methods 0.000 description 15
- 239000012153 distilled water Substances 0.000 description 8
- 238000010304 firing Methods 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 7
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 7
- 238000001354 calcination Methods 0.000 description 7
- 150000002500 ions Chemical class 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 229910017604 nitric acid Inorganic materials 0.000 description 7
- 238000002441 X-ray diffraction Methods 0.000 description 6
- BYUANIDVEAKBHT-UHFFFAOYSA-N [Mo].[Bi] Chemical compound [Mo].[Bi] BYUANIDVEAKBHT-UHFFFAOYSA-N 0.000 description 6
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 230000007423 decrease Effects 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- YLSLSHTYFFBCKG-UHFFFAOYSA-N bismuth;oxomolybdenum Chemical compound [Mo].[Bi]=O YLSLSHTYFFBCKG-UHFFFAOYSA-N 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 4
- VSOYJNRFGMJBAV-UHFFFAOYSA-N N.[Mo+4] Chemical compound N.[Mo+4] VSOYJNRFGMJBAV-UHFFFAOYSA-N 0.000 description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 description 4
- 238000006356 dehydrogenation reaction Methods 0.000 description 4
- RXPAJWPEYBDXOG-UHFFFAOYSA-N hydron;methyl 4-methoxypyridine-2-carboxylate;chloride Chemical compound Cl.COC(=O)C1=CC(OC)=CC=N1 RXPAJWPEYBDXOG-UHFFFAOYSA-N 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229910015902 Bi 2 O 3 Inorganic materials 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- MVFCKEFYUDZOCX-UHFFFAOYSA-N iron(2+);dinitrate Chemical compound [Fe+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O MVFCKEFYUDZOCX-UHFFFAOYSA-N 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 238000000197 pyrolysis Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000012265 solid product Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 238000000975 co-precipitation Methods 0.000 description 2
- -1 ethylene, propylene, butene Chemical class 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 2
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 229910003208 (NH4)6Mo7O24·4H2O Inorganic materials 0.000 description 1
- QYIGOGBGVKONDY-UHFFFAOYSA-N 1-(2-bromo-5-chlorophenyl)-3-methylpyrazole Chemical compound N1=C(C)C=CN1C1=CC(Cl)=CC=C1Br QYIGOGBGVKONDY-UHFFFAOYSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- 229910016870 Fe(NO3)3-9H2O Inorganic materials 0.000 description 1
- 229910000608 Fe(NO3)3.9H2O Inorganic materials 0.000 description 1
- 229910017299 Mo—O Inorganic materials 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 229910001308 Zinc ferrite Inorganic materials 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 229910000416 bismuth oxide Inorganic materials 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- DKUYEPUUXLQPPX-UHFFFAOYSA-N dibismuth;molybdenum;oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[Mo].[Mo].[Bi+3].[Bi+3] DKUYEPUUXLQPPX-UHFFFAOYSA-N 0.000 description 1
- TYIXMATWDRGMPF-UHFFFAOYSA-N dibismuth;oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Bi+3].[Bi+3] TYIXMATWDRGMPF-UHFFFAOYSA-N 0.000 description 1
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 1
- 238000005265 energy consumption Methods 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
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- 150000004698 iron complex Chemical class 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 235000013847 iso-butane Nutrition 0.000 description 1
- 239000007788 liquid Substances 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
- 229910003455 mixed metal oxide Inorganic materials 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 238000006479 redox reaction Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 239000006200 vaporizer Substances 0.000 description 1
- WGEATSXPYVGFCC-UHFFFAOYSA-N zinc ferrite Chemical compound O=[Zn].O=[Fe]O[Fe]=O WGEATSXPYVGFCC-UHFFFAOYSA-N 0.000 description 1
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Description
1−ブテンから1,3−ブタジエンを製造するBMF(Bi、Mo、Fe)触媒を水熱反応させて共沈法で製造した。
焼成温度による影響を調査するために、実施例1で製造したBMF0.75触媒を110℃で24時間乾燥した後、電気炉で450、550、650、750℃で焼成して複合金属酸化物触媒を製造した。
実施例1と異なる組成比を有する複合金属酸化物触媒を製造した。ビスマス、モリブデン、鉄のモル比が各々3:2:1となるように硝酸ビスマス5.8gと硝酸3.0gを蒸留水21gに添加して60℃でよく溶けるように十分に攪拌した。同様の方法で硝酸鉄1.6gと硝酸1.0gを蒸留水7.0gに添加して60℃でよく溶けるように十分に攪拌した。この2つの溶液をモリブデンアンモニウム1.4gと蒸留水14gが混合されている溶液に徐々に添加しながらよく攪拌した。そして、アンモニア水(NH4OH、デグァン化学、28%)を徐々に添加しながらpHを5.0に調節した。
複合酸化物触媒の活性を比較するために実施例1の方法と同様に行うが、鉄を添加せずに、ビスマスとモリブデンの含量のみを変化させた触媒を製造した。硝酸ビスマス16.5gと硝酸8.5gを蒸留水60gに添加して60℃でよく溶けるように十分に攪拌した。この溶液をモリブデンアンモニウム6.0gと蒸留水60gが混合されている溶液に徐々に添加しながらよく攪拌した。その後、アンモニア水を徐々に添加しながらpH5.0に調節した。60℃で水熱反応をさせながら蒸発乾燥機を利用して共沈した固体生成物を得た後、110℃で24時間乾燥させた。
実施例1〜3及び比較例で製造した触媒を使用して常圧流通式反応器で1−ブテンの酸化的脱水素化反応を実施した。
実施例1、3で製造したBMF、BMF'触媒を使用し、試験例1で説明した反応装置と実験方法により実施した反応結果を下記の表6に示した。
触媒の活性低下程度を確認するために、実施例1で製造し、試験例2で活性が最も優れたBMF0.65触媒を使用して、反応時間による1−ブテンの酸化的脱水素化反応の転換率と選択度を下記の表7に示した。
Claims (2)
- ビスマス、モリブデン及び鉄を1:1:0.5〜1.25のモル比で含み、且つBi 3 FeMo 2 O 12 相及びFe 2 (MoO 4 ) 3 相を含むことを特徴とする1,3−ブタジエン製造用ビスマス、モリブデン及び鉄の複合金属酸化物触媒。
- (a)ビスマス前駆体と鉄前駆体を60℃で溶解し、ビスマス前駆体溶液と鉄前駆体溶液を混合する第1工程、
(b)モリブデン前駆体溶液に前記混合溶液を添加し、塩基性溶液にて混合溶液のpHを調節する第2工程、
(c)前記pHが調節された混合溶液を60℃で水熱反応させ水熱反応生成物を得る第3工程、及び
(d)前記水熱反応による生成物を蒸発乾燥機を用いて乾燥した後、加熱して焼成させる第4工程と、
を含む1,3−ブタジエン製造用ビスマス、モリブデン及び鉄の複合金属酸化物触媒の製造方法。
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