JP7371102B2 - 炭素ベースの貴金属-遷移金属複合触媒及びこれの製造方法 - Google Patents
炭素ベースの貴金属-遷移金属複合触媒及びこれの製造方法 Download PDFInfo
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- JP7371102B2 JP7371102B2 JP2021537980A JP2021537980A JP7371102B2 JP 7371102 B2 JP7371102 B2 JP 7371102B2 JP 2021537980 A JP2021537980 A JP 2021537980A JP 2021537980 A JP2021537980 A JP 2021537980A JP 7371102 B2 JP7371102 B2 JP 7371102B2
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- 239000003054 catalyst Substances 0.000 title claims description 137
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 title claims description 109
- 229910052723 transition metal Inorganic materials 0.000 title claims description 85
- 229910052799 carbon Inorganic materials 0.000 title claims description 84
- 238000004519 manufacturing process Methods 0.000 title claims description 39
- 239000002905 metal composite material Substances 0.000 title claims description 22
- 229910052751 metal Inorganic materials 0.000 claims description 50
- 239000002184 metal Substances 0.000 claims description 50
- 238000005984 hydrogenation reaction Methods 0.000 claims description 45
- 239000002131 composite material Substances 0.000 claims description 35
- 229910000510 noble metal Inorganic materials 0.000 claims description 33
- 150000003624 transition metals Chemical class 0.000 claims description 33
- 239000002243 precursor Substances 0.000 claims description 21
- 238000001556 precipitation Methods 0.000 claims description 20
- 229910052707 ruthenium Inorganic materials 0.000 claims description 20
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 19
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical group OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 claims description 19
- 229910052718 tin Inorganic materials 0.000 claims description 19
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 18
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 15
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 15
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 13
- 239000007864 aqueous solution Substances 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 239000011148 porous material Substances 0.000 claims description 10
- 239000010948 rhodium Substances 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 8
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- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 8
- 125000003158 alcohol group Chemical group 0.000 claims description 7
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 7
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
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- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 6
- 150000002576 ketones Chemical group 0.000 claims description 6
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 6
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 claims description 6
- 230000009467 reduction Effects 0.000 claims description 6
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 5
- 229910052733 gallium Inorganic materials 0.000 claims description 5
- 239000007789 gas Substances 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052763 palladium Inorganic materials 0.000 claims description 5
- 229910052697 platinum Inorganic materials 0.000 claims description 5
- 229910052702 rhenium Inorganic materials 0.000 claims description 5
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims description 5
- 229910052703 rhodium Inorganic materials 0.000 claims description 5
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 5
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 4
- 239000001361 adipic acid Substances 0.000 claims description 4
- 235000011037 adipic acid Nutrition 0.000 claims description 4
- 239000002041 carbon nanotube Substances 0.000 claims description 4
- 229910021393 carbon nanotube Inorganic materials 0.000 claims description 4
- 239000013078 crystal Substances 0.000 claims description 4
- 125000001142 dicarboxylic acid group Chemical group 0.000 claims description 4
- 229910021389 graphene Inorganic materials 0.000 claims description 4
- 229910002804 graphite Inorganic materials 0.000 claims description 4
- 239000010439 graphite Substances 0.000 claims description 4
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
- 239000012670 alkaline solution Substances 0.000 claims description 3
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 3
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 235000006408 oxalic acid Nutrition 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
- 229910044991 metal oxide Inorganic materials 0.000 claims description 2
- 150000004706 metal oxides Chemical class 0.000 claims description 2
- 230000001376 precipitating effect Effects 0.000 claims description 2
- 125000003172 aldehyde group Chemical group 0.000 claims 1
- TWHMVKPVFOOAMY-UHFFFAOYSA-N octanedioic acid Chemical compound OC(=O)CCCCCCC(O)=O.OC(=O)CCCCCCC(O)=O TWHMVKPVFOOAMY-UHFFFAOYSA-N 0.000 claims 1
- 238000002161 passivation Methods 0.000 claims 1
- 238000000034 method Methods 0.000 description 64
- 238000006243 chemical reaction Methods 0.000 description 29
- 239000000203 mixture Substances 0.000 description 19
- 239000000243 solution Substances 0.000 description 16
- 230000008569 process Effects 0.000 description 15
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 14
- 229910017604 nitric acid Inorganic materials 0.000 description 14
- 230000000694 effects Effects 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 10
- 239000012153 distilled water Substances 0.000 description 10
- 238000005470 impregnation Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 8
- 238000002149 energy-dispersive X-ray emission spectroscopy Methods 0.000 description 8
- 238000005342 ion exchange Methods 0.000 description 8
- -1 cyclohexanedicarboxylic acid hexane dicarboxylic acid Chemical compound 0.000 description 7
- 150000002739 metals Chemical class 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 150000001299 aldehydes Chemical group 0.000 description 6
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 238000006722 reduction reaction Methods 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- 230000003197 catalytic effect Effects 0.000 description 5
- 229910052987 metal hydride Inorganic materials 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- FJJYHTVHBVXEEQ-UHFFFAOYSA-N 2,2-dimethylpropanal Chemical compound CC(C)(C)C=O FJJYHTVHBVXEEQ-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- FTZILAQGHINQQR-UHFFFAOYSA-N 2-Methylpentanal Chemical compound CCCC(C)C=O FTZILAQGHINQQR-UHFFFAOYSA-N 0.000 description 4
- BYGQBDHUGHBGMD-UHFFFAOYSA-N 2-methylbutanal Chemical compound CCC(C)C=O BYGQBDHUGHBGMD-UHFFFAOYSA-N 0.000 description 4
- YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 description 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 4
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- VEIOBOXBGYWJIT-UHFFFAOYSA-N cyclohexane;methanol Chemical compound OC.OC.C1CCCCC1 VEIOBOXBGYWJIT-UHFFFAOYSA-N 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- GGCUUOGRTPMFQK-UHFFFAOYSA-N dimethyl cyclohexane-1,1-dicarboxylate Chemical compound COC(=O)C1(C(=O)OC)CCCCC1 GGCUUOGRTPMFQK-UHFFFAOYSA-N 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000002638 heterogeneous catalyst Substances 0.000 description 4
- 150000004681 metal hydrides Chemical class 0.000 description 4
- NUJGJRNETVAIRJ-UHFFFAOYSA-N octanal Chemical compound CCCCCCCC=O NUJGJRNETVAIRJ-UHFFFAOYSA-N 0.000 description 4
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
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- 239000002841 Lewis acid Substances 0.000 description 2
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- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
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- 125000003342 alkenyl group Chemical group 0.000 description 2
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- 125000004122 cyclic group Chemical group 0.000 description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
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- 238000001035 drying Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
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- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
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- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
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- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
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- 229910001128 Sn alloy Inorganic materials 0.000 description 1
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- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- VQASCEOIYMPLRA-UHFFFAOYSA-N [C].[Sn].[Ru] Chemical compound [C].[Sn].[Ru] VQASCEOIYMPLRA-UHFFFAOYSA-N 0.000 description 1
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- 125000003545 alkoxy group Chemical group 0.000 description 1
- 238000005275 alloying Methods 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
- 125000003277 amino group Chemical group 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
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Description
[メカニズム1]
(特許文献2)中国特開公報103785418号(2014.05.14)
(特許文献3)中国特開公報106423202号(2017.02.22)
(特許文献4)米国登録特許公報2009-0131247号(2009.05.21)
本発明の実施例に従うと、前記貴金属-遷移金属は均一な混合相をなすことを特徴とする。
図2は本発明の一実施例に従った初期湿潤含浸法で製造したRu-Sn/C-IWI触媒のSTEM-EDX分析結果である。
四つ口フラスコに30gの炭素担体と300gの蒸留水、そして60%濃度の300gの硝酸溶液を順に投入する。還流冷却装置が付着された撹拌機を利用して95℃で3時間加熱攪拌して前記炭素懸濁液を常温に冷やせる。酸処理された炭素懸濁液は減圧濾過を通じて沈殿物を収得するし、残存する有無機物の除去のため洗浄する。この時、濾過液のpHが7になるまで何回distilled waterを使用して洗浄した。収得した炭素粉末は100℃オーブンで24時間の間乾燥させて触媒の担体に使用した。
触媒の製造装置は1000ml用量の五ツ口フラスコを利用して各枝に還流冷却器、pH電極、高速撹拌機(overhead stirrer)、温度センサー及び沈殿剤注入管を付着させて使用する。先ず、還流冷却装置が付着されたフラスコに前記[製造例1]で製造された炭素担体10gと蒸留水300mlを入れ分散させて80℃の温度で約1時間攪拌させる(400rpm)。ルテニウム-錫前駆体溶液を作るため30mlの0.05mのHCl溶液にRuCl3.3H2O 3.9gとSnCl2.2H2O 3.5gを同時に溶解させた後400rpmの速度で30分の間攪拌した。ルテニウム-錫前駆体溶液を炭素担体が分散されている80℃の炭素担体分散液に添加した後1時間の間攪拌してあげる。沈殿剤(1MのNH4OH)をルテニウム-錫-炭素担体混合溶液に漸進的に追加して(5cc/min)最終pHを6に合わせた後、1時間攪拌しながら維持する。沈殿が終わった後、沈殿溶液を常温に冷やせた後、回収した沈殿物は80℃以上の蒸留水で洗浄して残存有無機物たちを除去してあげる。洗浄が終わった後沈殿物は100℃convection ovenで乾燥する。これを水素(100cc/min H2:30/N2:70)を流しながら500℃で3時間の間還元させた後、窒素(100cc/min)を流しながら室温に冷やせた。以後3%酸素/窒素混合ガス(100cc/min Air:15/N2:85)を1時間の間流しながら不動態化して触媒を製造した。前記のように製造された触媒を“Ru-Sn/C-DP”で表記する。
30wt%硝酸で前処理した炭素担体にルテニウムと錫を担持するためルテニウム前駆体(3.9gのRuCl3.3H2O)と錫前駆体(3.5gのSnCl2.2H2O)を蒸留水に溶かした後二つの前駆体を一気に担持する初期湿潤含浸法で担持した。以後100℃convectionオーブンで12時間の間乾燥する。これを水素(100cc/min H2:30/N2:70)を流しながら500℃で3時間の間還元させた後、窒素(100cc/min)を流しながら室温に冷やせた。以後3%酸素/窒素混合ガス(100cc/min Air:15/N2:85)を1時間の間流しながら不動態化して触媒を製造した。前記のように製造された触媒を“Ru-Sn/C-IWI”と表記する。
前記実施例1及び比較例2で製造された触媒に対して、各触媒のSTEM-EDX(Energy Dispersive X-Ray spectroscopy) mapping結果をそれぞれ[図1]及び[図2]に表せた。[図1]は[実施例1]で本発明に従った、沈積-沈殿法を使用したRu-Sn/C触媒を表れるし、[図2]は[比較例1]で初期湿潤含浸法で製造したRu-Sn/C-IWI触媒のSTEM-EDX分析結果を表せる。
Dicarboxylic acidで代表されるCHDAの水素化反応を通じた通じたCHDM転換実験を行った。本反応は最大作業圧力が100barである耐酸性のtitanium-lined stainless材質の回分式反応器(batch reactor)で遂行した。反応器に反応物であるCHDAと触媒を重量比で3.75:1になるように注入し、反応溶媒では蒸留水を充填した。この時溶媒対比反応物の量は1.6wt%で固定した。以後水素を反応圧力である90barまで加圧した後水素感知器を通じて反応器のleak可否を確認した後減圧及び換気(purge)して反応器内部の酸素を全て除去した。水素化反応は反応器の内部温度を反応温度(230℃)まで加熱後、水素雰囲気の反応圧力(90bar)で加圧及び維持しながらoverhead stirrerを利用して反応混合物を1000rpmで6時間攪拌しながら進行した。metal filterを通じて反応時間別生成物をsamplingしたし、N,O-Bis(trimethylsilyl) trifluoroacetamide (BSTFA)でsilylationをした後、HP-1カラム(Agilent)が具備されたガスクロマトグラフィー(DS-SCIENCE)を利用して生成物及び残余反応物を分析した。触媒活性(activity)は時間に従った生成物の転換率(Conversion)及び収率(Yield)で比べたし、下記に[数学式1]~[数学式3]で表せた。
[数学式1]
[数学式2]
[数学式3]
Claims (15)
- 炭素を担体として用いる貴金属-遷移金属水素化複合触媒であって、
複合触媒100重量部に対して前記貴金属は10~20重量部、前記遷移金属は10~20重量部を含み、全体の貴金属-遷移金属は複合触媒100重量部に対して20~40重量部を含む、炭素を担体として用いる貴金属-遷移金属複合触媒であり、
前記複合触媒は水素化反応に利用され、
前記貴金属はパラジウム(Pd)、ロジウム(Rh)、ルテニウム(Ru)及び白金(Pt)からなる群から選択された1種以上であり、そして
前記遷移金属は錫(Sn)、鉄(Fe)、レニウム(Re)及びガリウム(Ga)からなる群から選択された1種以上であることを特徴とする炭素を担体として用い、そして
前記貴金属-遷移金属は均一な混合相をなす、貴金属-遷移金属水素化複合触媒。 - 貴金属-遷移金属は活性金属で、活性金属の金属結晶サイズが(metal crystallite size)1~20nmであることを特徴とする、請求項1に記載の、炭素を担体として用いる貴金属-遷移金属水素化複合触媒。
- 前記貴金属と遷移金属とは前記担体に貴金属1モル当たり遷移金属0.5モル~3モルの範囲で担持されていることを特徴とする、請求項1に記載の、炭素を担体として用いる貴金属-遷移金属水素化複合触媒。
- 前記貴金属-遷移金属複合触媒の平均粒子サイズ(d50)は3~50μmである、請求項1に記載の、炭素を担体として用いる貴金属-遷移金属水素化複合触媒。
- 前記炭素は活性炭、カーボンブラック、黒鉛、グラフェン、規則的なメソポーラス炭素(ordered mesoporous carbon、OMC)及び炭素ナノチューブからなる群から選択された1種以上であることを特徴とする、請求項1に記載の、炭素を担体として用いる貴金属-遷移金属水素化複合触媒。
- 前記炭素は比表面積が100~1,500m2/g範囲であり、細孔容積(pore volume)は0.1~1.5ml/g範囲であることを特徴とする、請求項1に記載の、炭素を担体として用いる貴金属-遷移金属水素化複合触媒。
- 前記炭素は2~25nmの規則的なメソ孔を持つことを特徴とする、請求項1に記載の、炭素を担体として用いる貴金属-遷移金属水素化複合触媒。
- 前記水素化反応はジカルボン酸官能基(dicarboxylic acid group)をジアルコール官能基(dialcohol group)に還元することを特徴とする、請求項1に記載の、炭素を担体として用いる貴金属-遷移金属水素化複合触媒。
- 前記水素化反応はカルボン酸官能基、アルデヒド官能基又はケトン官能基をアルコール官能基に還元することを特徴とする、請求項1に記載の、炭素を担体として用いる貴金属-遷移金属水素化複合触媒。
- 前記カルボン酸官能基は蓚酸(oxalic acid)、マロン酸(malonic acid)、琥珀酸(succinic acid)、グルタル酸(glutaric acid)、アジピン酸(adipic acid)、ピメリン酸(pimelic acid)、スベリン酸(suberic acid)、アゼライン酸(azelaic acid)、セバシン酸(sebacic acid)、フタル酸(phthalic acid)、イソフタル酸(isopthalic acid)、シクロヘキサンジカルボン酸(cyclohexane dicarboxylic acid)及びテレフタル酸(terephthalic acid)からなる群から選択された1種以上であることを特徴とする、請求項9に記載の、炭素を担体として用いる貴金属-遷移金属水素化複合触媒。
- (a)炭素担体を溶媒に分散させた担体分散液を製造する段階;
(b)担体分散液に貴金属-遷移金属前駆体水溶液及び沈殿剤を投入して金属酸化物又は金属水和物を前記炭素担体に担持させて沈殿する段階;及び
(c)前記沈殿物を還元及び不動態化する段階を含む、請求項1に記載の炭素を担体として用いる貴金属-遷移金属水素化複合触媒の製造方法であって、
貴金属-遷移金属複合触媒は複合触媒100重量部に対して前記貴金属は10~20重量部、前記遷移金属は10~20重量部を含み、全体の貴金属-遷移金属は複合触媒100重量部に対して20~40重量部を含み、
前記(b)段階で貴金属はパラジウム(Pd)、ロジウム(Rh)、ルテニウム(Ru)及び白金(Pt)からなる群から選択される1種以上であり、そして
前記(b)段階で遷移金属は錫(Sn)、鉄(Fe)、レニウム(Re)及びガリウム(Ga)からなる群から選択された1種以上であることを特徴とする、請求項1に記載の炭素を担体として用いる貴金属-遷移金属水素化複合触媒の製造方法。 - 前記(b)段階の沈殿はアルカリ性溶液沈殿剤を使用して、沈殿剤はヒドロキシド(OH-)、カーボネイト(C03 2-)、及び尿素(Urea)からなる群から選択された1種以上を含むことを特徴とする、請求項11に記載の炭素を担体として用いる貴金属-遷移金属水素化複合触媒の製造方法。
- 前記(b)段階の沈殿で沈殿物の製造の時のpHは3~7であることを特徴とする、請求項11に記載の炭素を担体として用いる貴金属-遷移金属水素化複合触媒の製造方法。
- 前記(c)段階の還元は水素雰囲気で300~600℃の範囲で行うことを特徴とする、請求項11に記載の炭素を担体として用いる貴金属-遷移金属水素化複合触媒の製造方法。
- 前記(c)段階の不動態化は1~20%酸素が含まれた窒素混合ガスで不動態化することを特徴とする、請求項11に記載の炭素を担体として用いる貴金属-遷移金属水素化複合触媒の製造方法。
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KR101504672B1 (ko) * | 2013-03-27 | 2015-03-23 | 서울대학교산학협력단 | 균일한 기공 구조의 전이금속-탄소 복합체에 담지된 귀금속 담지 촉매, 그 제조 방법 및 상기 촉매를 이용하여 숙신산으로부터 1,4-부탄디올과 디메틸숙시네이트의 혼합물을 제조하는 방법 |
CN104549251A (zh) * | 2013-10-28 | 2015-04-29 | 中国石油化工股份有限公司 | 用于1,4-环己烷二甲醇合成的催化剂及其制备方法 |
CN104549494B (zh) | 2013-10-28 | 2017-06-20 | 中国石油化工股份有限公司 | 合成1,4‑环己烷二甲醇的催化剂 |
KR101572846B1 (ko) * | 2014-03-20 | 2015-11-30 | 서울대학교산학협력단 | 규칙적인 중형기공구조를 갖는 레늄-구리-탄소 복합체 촉매, 그 제조방법 및 상기 촉매를 이용한 1,4-부탄디올의 생산 방법 |
KR101578071B1 (ko) * | 2015-05-20 | 2015-12-16 | 주식회사 디알액시온 | 귀금속 담지 촉매의 고분산 제조 방법 |
CN107365286B (zh) * | 2016-05-11 | 2019-12-27 | 中国石油化工股份有限公司 | 一种合成2,5-呋喃二甲酸的方法 |
CN106423202A (zh) | 2016-09-14 | 2017-02-22 | 中溶科技股份有限公司 | 一种醋酸加氢制备乙醇的铑钌复合催化剂的制备方法 |
KR102238560B1 (ko) | 2017-12-29 | 2021-04-08 | 한화솔루션 주식회사 | 고선택 전환이 가능한 탄소 기반의 귀금속-전이금속 촉매 및 이의 제조방법 |
RU2675361C1 (ru) | 2018-08-06 | 2018-12-19 | Федеральное государственное бюджетное учреждение науки Ордена Трудового Красного Знамени Институт нефтехимического синтеза им. А.В. Топчиева Российской академии наук (ИНХС РАН) | Способ получения катализатора и способ гидрирования нефтеполимерных смол в его присутствии |
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2018
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EP3907000A1 (en) | 2021-11-10 |
US11969711B2 (en) | 2024-04-30 |
KR20200082915A (ko) | 2020-07-08 |
JP2023153810A (ja) | 2023-10-18 |
JP2022515852A (ja) | 2022-02-22 |
EP3907000A4 (en) | 2022-11-02 |
US20220062868A1 (en) | 2022-03-03 |
CN113272055A (zh) | 2021-08-17 |
CN113272055B (zh) | 2023-12-29 |
WO2020141748A1 (ko) | 2020-07-09 |
KR102287646B1 (ko) | 2021-08-06 |
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