CN114829004A - 一种制备Ni-X基氧化物催化剂的方法及其在转移加氢中的应用 - Google Patents
一种制备Ni-X基氧化物催化剂的方法及其在转移加氢中的应用 Download PDFInfo
- Publication number
- CN114829004A CN114829004A CN202080087000.3A CN202080087000A CN114829004A CN 114829004 A CN114829004 A CN 114829004A CN 202080087000 A CN202080087000 A CN 202080087000A CN 114829004 A CN114829004 A CN 114829004A
- Authority
- CN
- China
- Prior art keywords
- alcohol
- solution
- based oxide
- catalyst
- precursor
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 111
- 238000009901 transfer hydrogenation reaction Methods 0.000 title claims abstract description 35
- 238000000034 method Methods 0.000 title claims description 46
- 229920000642 polymer Polymers 0.000 claims abstract description 65
- 238000006243 chemical reaction Methods 0.000 claims abstract description 59
- 229910052751 metal Inorganic materials 0.000 claims abstract description 43
- 239000006185 dispersion Substances 0.000 claims abstract description 33
- -1 aldehyde compound Chemical class 0.000 claims abstract description 21
- 239000012752 auxiliary agent Substances 0.000 claims abstract description 13
- 230000003197 catalytic effect Effects 0.000 claims abstract description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 117
- 239000000243 solution Substances 0.000 claims description 94
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 80
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 66
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 claims description 48
- 239000002243 precursor Substances 0.000 claims description 47
- 239000002184 metal Substances 0.000 claims description 38
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 claims description 36
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 33
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 32
- 239000002904 solvent Substances 0.000 claims description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 32
- 239000000725 suspension Substances 0.000 claims description 27
- 238000005406 washing Methods 0.000 claims description 25
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 24
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 24
- 239000004793 Polystyrene Substances 0.000 claims description 23
- 238000010438 heat treatment Methods 0.000 claims description 23
- 229920002223 polystyrene Polymers 0.000 claims description 23
- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 22
- 239000003513 alkali Substances 0.000 claims description 18
- 238000001035 drying Methods 0.000 claims description 18
- 239000007788 liquid Substances 0.000 claims description 18
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 claims description 16
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 16
- 238000001914 filtration Methods 0.000 claims description 16
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 15
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 15
- 239000012298 atmosphere Substances 0.000 claims description 15
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 claims description 14
- 230000032683 aging Effects 0.000 claims description 14
- 239000011259 mixed solution Substances 0.000 claims description 14
- 239000008367 deionised water Substances 0.000 claims description 13
- 229910021641 deionized water Inorganic materials 0.000 claims description 13
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 claims description 13
- 239000011324 bead Substances 0.000 claims description 11
- 230000001276 controlling effect Effects 0.000 claims description 11
- OOCCDEMITAIZTP-QPJJXVBHSA-N (E)-cinnamyl alcohol Chemical compound OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-N 0.000 claims description 10
- 229910002651 NO3 Inorganic materials 0.000 claims description 10
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 10
- MSHFRERJPWKJFX-UHFFFAOYSA-N 4-Methoxybenzyl alcohol Chemical compound COC1=CC=C(CO)C=C1 MSHFRERJPWKJFX-UHFFFAOYSA-N 0.000 claims description 9
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 claims description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 8
- NEHNMFOYXAPHSD-UHFFFAOYSA-N citronellal Chemical compound O=CCC(C)CCC=C(C)C NEHNMFOYXAPHSD-UHFFFAOYSA-N 0.000 claims description 8
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 8
- 229910052742 iron Inorganic materials 0.000 claims description 8
- 229910052726 zirconium Inorganic materials 0.000 claims description 8
- 239000001431 2-methylbenzaldehyde Substances 0.000 claims description 7
- NOEGNKMFWQHSLB-UHFFFAOYSA-N 5-hydroxymethylfurfural Chemical compound OCC1=CC=C(C=O)O1 NOEGNKMFWQHSLB-UHFFFAOYSA-N 0.000 claims description 7
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical class CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 claims description 7
- 150000001299 aldehydes Chemical class 0.000 claims description 7
- KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 claims description 7
- 229940117916 cinnamic aldehyde Drugs 0.000 claims description 7
- 229910052802 copper Inorganic materials 0.000 claims description 7
- HFJRKMMYBMWEAD-UHFFFAOYSA-N dodecanal Chemical compound CCCCCCCCCCCC=O HFJRKMMYBMWEAD-UHFFFAOYSA-N 0.000 claims description 7
- RJGBSYZFOCAGQY-UHFFFAOYSA-N hydroxymethylfurfural Natural products COC1=CC=C(C=O)O1 RJGBSYZFOCAGQY-UHFFFAOYSA-N 0.000 claims description 7
- 229910052719 titanium Inorganic materials 0.000 claims description 7
- XPNGNIFUDRPBFJ-UHFFFAOYSA-N (2-methylphenyl)methanol Chemical compound CC1=CC=CC=C1CO XPNGNIFUDRPBFJ-UHFFFAOYSA-N 0.000 claims description 6
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims description 6
- PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 claims description 6
- WMPDAIZRQDCGFH-UHFFFAOYSA-N 3-methoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1 WMPDAIZRQDCGFH-UHFFFAOYSA-N 0.000 claims description 6
- JVJFIQYAHPMBBX-UHFFFAOYSA-N 4-hydroxynonenal Chemical compound CCCCCC(O)C=CC=O JVJFIQYAHPMBBX-UHFFFAOYSA-N 0.000 claims description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 6
- 229910052782 aluminium Inorganic materials 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 6
- 229910052804 chromium Inorganic materials 0.000 claims description 6
- 229940043350 citral Drugs 0.000 claims description 6
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 claims description 6
- WTWBUQJHJGUZCY-UHFFFAOYSA-N cuminaldehyde Chemical compound CC(C)C1=CC=C(C=O)C=C1 WTWBUQJHJGUZCY-UHFFFAOYSA-N 0.000 claims description 6
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 claims description 6
- KSMVZQYAVGTKIV-UHFFFAOYSA-N decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 claims description 6
- 229910052749 magnesium Inorganic materials 0.000 claims description 6
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 claims description 6
- GYHFUZHODSMOHU-UHFFFAOYSA-N nonanal Chemical compound CCCCCCCCC=O GYHFUZHODSMOHU-UHFFFAOYSA-N 0.000 claims description 6
- BTFQKIATRPGRBS-UHFFFAOYSA-N o-tolualdehyde Chemical compound CC1=CC=CC=C1C=O BTFQKIATRPGRBS-UHFFFAOYSA-N 0.000 claims description 6
- NUJGJRNETVAIRJ-UHFFFAOYSA-N octanal Chemical compound CCCCCCCC=O NUJGJRNETVAIRJ-UHFFFAOYSA-N 0.000 claims description 6
- ASUAYTHWZCLXAN-UHFFFAOYSA-N prenol Chemical compound CC(C)=CCO ASUAYTHWZCLXAN-UHFFFAOYSA-N 0.000 claims description 6
- 229910052725 zinc Inorganic materials 0.000 claims description 6
- OOCCDEMITAIZTP-UHFFFAOYSA-N allylic benzylic alcohol Natural products OCC=CC1=CC=CC=C1 OOCCDEMITAIZTP-UHFFFAOYSA-N 0.000 claims description 5
- 238000001354 calcination Methods 0.000 claims description 5
- 150000003841 chloride salts Chemical class 0.000 claims description 5
- 229910052759 nickel Inorganic materials 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- DSLRVRBSNLHVBH-UHFFFAOYSA-N 2,5-furandimethanol Chemical compound OCC1=CC=C(CO)O1 DSLRVRBSNLHVBH-UHFFFAOYSA-N 0.000 claims description 4
- 241000134874 Geraniales Species 0.000 claims description 4
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 claims description 4
- 239000005792 Geraniol Substances 0.000 claims description 4
- GLZPCOQZEFWAFX-JXMROGBWSA-N Nerol Natural products CC(C)=CCC\C(C)=C\CO GLZPCOQZEFWAFX-JXMROGBWSA-N 0.000 claims description 4
- WTEVQBCEXWBHNA-YFHOEESVSA-N citral B Natural products CC(C)=CCC\C(C)=C/C=O WTEVQBCEXWBHNA-YFHOEESVSA-N 0.000 claims description 4
- 229930003633 citronellal Natural products 0.000 claims description 4
- 235000000983 citronellal Nutrition 0.000 claims description 4
- 229940113087 geraniol Drugs 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- WPFVBOQKRVRMJB-UHFFFAOYSA-N hydroxycitronellal Chemical compound O=CCC(C)CCCC(C)(C)O WPFVBOQKRVRMJB-UHFFFAOYSA-N 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- KJIOQYGWTQBHNH-UHFFFAOYSA-N undecanol Chemical compound CCCCCCCCCCCO KJIOQYGWTQBHNH-UHFFFAOYSA-N 0.000 claims description 4
- OGCGGWYLHSJRFY-SECBINFHSA-N (+)-alpha-Campholenal Natural products CC1=CC[C@H](CC=O)C1(C)C OGCGGWYLHSJRFY-SECBINFHSA-N 0.000 claims description 3
- CRDAMVZIKSXKFV-FBXUGWQNSA-N (2-cis,6-cis)-farnesol Chemical compound CC(C)=CCC\C(C)=C/CC\C(C)=C/CO CRDAMVZIKSXKFV-FBXUGWQNSA-N 0.000 claims description 3
- WYLYBQSHRJMURN-UHFFFAOYSA-N (2-methoxyphenyl)methanol Chemical compound COC1=CC=CC=C1CO WYLYBQSHRJMURN-UHFFFAOYSA-N 0.000 claims description 3
- YHRUHBBTQZKMEX-YFVJMOTDSA-N (2-trans,6-trans)-farnesal Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\C=O YHRUHBBTQZKMEX-YFVJMOTDSA-N 0.000 claims description 3
- YHRUHBBTQZKMEX-UHFFFAOYSA-N (2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrien-1-al Natural products CC(C)=CCCC(C)=CCCC(C)=CC=O YHRUHBBTQZKMEX-UHFFFAOYSA-N 0.000 claims description 3
- 239000000260 (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol Substances 0.000 claims description 3
- BTSIZIIPFNVMHF-ONEGZZNKSA-N (E)-2-penten-1-ol Chemical compound CC\C=C\CO BTSIZIIPFNVMHF-ONEGZZNKSA-N 0.000 claims description 3
- DTCCTIQRPGSLPT-ONEGZZNKSA-N (E)-2-pentenal Chemical compound CC\C=C\C=O DTCCTIQRPGSLPT-ONEGZZNKSA-N 0.000 claims description 3
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 claims description 3
- TWJPSNFPBZSAEJ-VMPITWQZSA-N (e)-non-1-ene-1,4-diol Chemical compound CCCCCC(O)C\C=C\O TWJPSNFPBZSAEJ-VMPITWQZSA-N 0.000 claims description 3
- JESIHYIJKKUWIS-UHFFFAOYSA-N 1-(4-Methylphenyl)ethanol Chemical compound CC(O)C1=CC=C(C)C=C1 JESIHYIJKKUWIS-UHFFFAOYSA-N 0.000 claims description 3
- SIRPHJCQZYVEES-UHFFFAOYSA-N 1-methylbenzimidazole-2-carbaldehyde Chemical compound C1=CC=C2N(C)C(C=O)=NC2=C1 SIRPHJCQZYVEES-UHFFFAOYSA-N 0.000 claims description 3
- OLUJUQKZMDLFII-UHFFFAOYSA-N 1-phenyloct-1-en-3-ol Chemical compound CCCCCC(O)C=CC1=CC=CC=C1 OLUJUQKZMDLFII-UHFFFAOYSA-N 0.000 claims description 3
- UIFVCPMLQXKEEU-UHFFFAOYSA-N 2,3-dimethylbenzaldehyde Chemical compound CC1=CC=CC(C=O)=C1C UIFVCPMLQXKEEU-UHFFFAOYSA-N 0.000 claims description 3
- HMKKIXGYKWDQSV-SDNWHVSQSA-N 2-Pentyl-3-phenyl-2-propenal Chemical compound CCCCC\C(C=O)=C/C1=CC=CC=C1 HMKKIXGYKWDQSV-SDNWHVSQSA-N 0.000 claims description 3
- IIGNZLVHOZEOPV-UHFFFAOYSA-N 3-Methoxybenzyl alcohol Chemical compound COC1=CC=CC(CO)=C1 IIGNZLVHOZEOPV-UHFFFAOYSA-N 0.000 claims description 3
- JJCKHVUTVOPLBV-UHFFFAOYSA-N 3-Methylbenzyl alcohol Chemical compound CC1=CC=CC(CO)=C1 JJCKHVUTVOPLBV-UHFFFAOYSA-N 0.000 claims description 3
- SEPQTYODOKLVSB-UHFFFAOYSA-N 3-methylbut-2-enal Chemical compound CC(C)=CC=O SEPQTYODOKLVSB-UHFFFAOYSA-N 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- YHRUHBBTQZKMEX-FBXUGWQNSA-N E,E-Farnesal Natural products CC(C)=CCC\C(C)=C/CC\C(C)=C/C=O YHRUHBBTQZKMEX-FBXUGWQNSA-N 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- 230000000996 additive effect Effects 0.000 claims description 3
- OGCGGWYLHSJRFY-UHFFFAOYSA-N alpha-campholenaldehyde Chemical compound CC1=CCC(CC=O)C1(C)C OGCGGWYLHSJRFY-UHFFFAOYSA-N 0.000 claims description 3
- 150000001491 aromatic compounds Chemical class 0.000 claims description 3
- DTCCTIQRPGSLPT-UHFFFAOYSA-N beta-Aethyl-acrolein Natural products CCC=CC=O DTCCTIQRPGSLPT-UHFFFAOYSA-N 0.000 claims description 3
- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 claims description 3
- SIIVGPQREKVCOP-UHFFFAOYSA-N but-1-en-1-ol Chemical compound CCC=CO SIIVGPQREKVCOP-UHFFFAOYSA-N 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 235000000484 citronellol Nutrition 0.000 claims description 3
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 claims description 3
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 claims description 3
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 claims description 3
- 229940043259 farnesol Drugs 0.000 claims description 3
- 229930002886 farnesol Natural products 0.000 claims description 3
- OVWYEQOVUDKZNU-UHFFFAOYSA-N m-tolualdehyde Chemical compound CC1=CC=CC(C=O)=C1 OVWYEQOVUDKZNU-UHFFFAOYSA-N 0.000 claims description 3
- 150000002825 nitriles Chemical class 0.000 claims description 3
- BTSIZIIPFNVMHF-UHFFFAOYSA-N nor-leaf alcohol Natural products CCC=CCO BTSIZIIPFNVMHF-UHFFFAOYSA-N 0.000 claims description 3
- OIGWAXDAPKFNCQ-UHFFFAOYSA-N p-Isopropylbenzyl alcohol Natural products CC(C)C1=CC=C(CO)C=C1 OIGWAXDAPKFNCQ-UHFFFAOYSA-N 0.000 claims description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 3
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- CRDAMVZIKSXKFV-UHFFFAOYSA-N trans-Farnesol Natural products CC(C)=CCCC(C)=CCCC(C)=CCO CRDAMVZIKSXKFV-UHFFFAOYSA-N 0.000 claims description 3
- OFHHDSQXFXLTKC-UHFFFAOYSA-N 10-undecenal Chemical compound C=CCCCCCCCCC=O OFHHDSQXFXLTKC-UHFFFAOYSA-N 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- 230000001172 regenerating effect Effects 0.000 claims description 2
- 230000001105 regulatory effect Effects 0.000 claims description 2
- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 claims 4
- OVBPIULPVIDEAO-UHFFFAOYSA-N N-Pteroyl-L-glutaminsaeure Natural products C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-UHFFFAOYSA-N 0.000 claims 2
- 229960000304 folic acid Drugs 0.000 claims 2
- 235000019152 folic acid Nutrition 0.000 claims 2
- 239000011724 folic acid Substances 0.000 claims 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 claims 1
- 229940089454 lauryl aldehyde Drugs 0.000 claims 1
- 229940057402 undecyl alcohol Drugs 0.000 claims 1
- 239000012018 catalyst precursor Substances 0.000 abstract description 26
- 238000002360 preparation method Methods 0.000 abstract description 10
- 239000007787 solid Substances 0.000 abstract description 9
- 230000000694 effects Effects 0.000 abstract description 8
- 229910021645 metal ion Inorganic materials 0.000 abstract description 7
- 230000003647 oxidation Effects 0.000 abstract description 6
- 238000007254 oxidation reaction Methods 0.000 abstract description 6
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 238000012546 transfer Methods 0.000 abstract description 4
- 238000000926 separation method Methods 0.000 abstract description 3
- 238000001179 sorption measurement Methods 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- 230000001351 cycling effect Effects 0.000 abstract 1
- 230000009881 electrostatic interaction Effects 0.000 abstract 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 40
- 239000005011 phenolic resin Substances 0.000 description 20
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 17
- 238000004817 gas chromatography Methods 0.000 description 17
- 229920001568 phenolic resin Polymers 0.000 description 17
- 239000011541 reaction mixture Substances 0.000 description 17
- 239000011949 solid catalyst Substances 0.000 description 16
- 229910003310 Ni-Al Inorganic materials 0.000 description 15
- 229910003271 Ni-Fe Inorganic materials 0.000 description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
- 238000001816 cooling Methods 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 10
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 10
- 239000012266 salt solution Substances 0.000 description 10
- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 description 9
- 238000005984 hydrogenation reaction Methods 0.000 description 7
- 229960001545 hydrotalcite Drugs 0.000 description 7
- 229910001701 hydrotalcite Inorganic materials 0.000 description 7
- 239000012716 precipitator Substances 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 6
- 150000004706 metal oxides Chemical class 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- KBJMLQFLOWQJNF-UHFFFAOYSA-N nickel(ii) nitrate Chemical compound [Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O KBJMLQFLOWQJNF-UHFFFAOYSA-N 0.000 description 6
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 description 5
- 229910044991 metal oxide Inorganic materials 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000010936 titanium Substances 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000013459 approach Methods 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000001291 vacuum drying Methods 0.000 description 3
- MBDOYVRWFFCFHM-SNAWJCMRSA-N (2E)-hexenal Chemical compound CCC\C=C\C=O MBDOYVRWFFCFHM-SNAWJCMRSA-N 0.000 description 2
- UFLHIIWVXFIJGU-ARJAWSKDSA-N (Z)-hex-3-en-1-ol Chemical compound CC\C=C/CCO UFLHIIWVXFIJGU-ARJAWSKDSA-N 0.000 description 2
- 239000002028 Biomass Substances 0.000 description 2
- FPCCDPXRNNVUOM-UHFFFAOYSA-N Hydroxycitronellol Chemical compound OCCC(C)CCCC(C)(C)O FPCCDPXRNNVUOM-UHFFFAOYSA-N 0.000 description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000012824 chemical production Methods 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 239000012847 fine chemical Substances 0.000 description 2
- 239000002638 heterogeneous catalyst Substances 0.000 description 2
- 239000002815 homogeneous catalyst Substances 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- KMPQYAYAQWNLME-UHFFFAOYSA-N undecanal Chemical compound CCCCCCCCCCC=O KMPQYAYAQWNLME-UHFFFAOYSA-N 0.000 description 2
- BNGXYYYYKUGPPF-UHFFFAOYSA-M (3-methylphenyl)methyl-triphenylphosphanium;chloride Chemical compound [Cl-].CC1=CC=CC(C[P+](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 BNGXYYYYKUGPPF-UHFFFAOYSA-M 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- QXZUUHYBWMWJHK-UHFFFAOYSA-N [Co].[Ni] Chemical compound [Co].[Ni] QXZUUHYBWMWJHK-UHFFFAOYSA-N 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000013064 chemical raw material Substances 0.000 description 1
- 238000000975 co-precipitation Methods 0.000 description 1
- 239000011258 core-shell material Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- MVFCKEFYUDZOCX-UHFFFAOYSA-N iron(2+);dinitrate Chemical compound [Fe+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O MVFCKEFYUDZOCX-UHFFFAOYSA-N 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 239000011943 nanocatalyst Substances 0.000 description 1
- 239000002077 nanosphere Substances 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 0.000 description 1
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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/74—Iron group metals
- B01J23/755—Nickel
-
- B01J35/394—
-
- B01J35/60—
-
- B01J35/61—
Abstract
本发明公开了一种Ni‑X基氧化物催化剂的制备方法及其在醛类化合物转移加氢中应用。以聚合物球为模板，由于金属离子与聚合物球表面之间存在强静电作用，使Ni2+、Xn+和其它金属离子助剂均匀吸附在聚合物表面，并以此为基础在聚合物表面形成的类水滑石结构物质作为催化剂前驱体，可以实现金属元素之间的均匀分散；由于类水滑石均匀覆盖在聚合物球表面，氧化处理脱除聚合物后，可以构筑Ni‑X基氧化物空心球结构；此外，不添加模板剂，可制备具有实心结构的Ni‑X基氧化物催化剂。所获得的催化剂具有高活性比表面积、高分散度高、高传质，生产成本低，易于分离等特点，应用于醛类化合物转移加氢反应中，表现出高催化活性、高选择性、循环稳定性好等特点。
Description
PCT国内申请，说明书已公开。
Claims (16)
- PCT国内申请，权利要求书已公开。
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911328809.6A CN113000049B (zh) | 2019-12-20 | 2019-12-20 | 一种制备Ni-Al基氧化物催化剂的方法 |
| CN2019113288096 | 2019-12-20 | ||
| PCT/CN2020/128198 WO2021120928A1 (zh) | 2019-12-20 | 2020-11-11 | 一种制备Ni-X基氧化物催化剂的方法及其在转移加氢中的应用 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN114829004A true CN114829004A (zh) | 2022-07-29 |
| CN114829004B CN114829004B (zh) | 2024-02-27 |
Family
ID=76382119
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201911328809.6A Active CN113000049B (zh) | 2019-12-20 | 2019-12-20 | 一种制备Ni-Al基氧化物催化剂的方法 |
| CN202080087000.3A Active CN114829004B (zh) | 2019-12-20 | 2020-11-11 | 一种制备Ni-X基氧化物催化剂的方法及其在转移加氢中的应用 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201911328809.6A Active CN113000049B (zh) | 2019-12-20 | 2019-12-20 | 一种制备Ni-Al基氧化物催化剂的方法 |
Country Status (2)
| Country | Link |
|---|---|
| CN (2) | CN113000049B (zh) |
| WO (1) | WO2021120928A1 (zh) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113522294B (zh) * | 2021-08-11 | 2023-08-29 | 中国科学院青岛生物能源与过程研究所 | 一种Ni基催化剂及其制备方法与在还原胺化中的应用 |
| CN114573419A (zh) * | 2022-02-09 | 2022-06-03 | 大连理工大学 | 一种以水作为廉价供氢体的α,β-不饱和醛原位选择性加氢反应工艺 |
| CN114849711B (zh) * | 2022-04-27 | 2023-08-11 | 苏州大学 | 一种金属纳米催化剂、其制备方法及应用 |
| CN115779956B (zh) * | 2022-12-07 | 2024-04-09 | 万华化学集团股份有限公司 | 一种己二腈加氢催化剂的制备方法与应用 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103962140A (zh) * | 2014-05-12 | 2014-08-06 | 北京化工大学 | 一种微球形中空结构镍基加氢催化剂及其制备方法 |
| CN107282050A (zh) * | 2017-07-14 | 2017-10-24 | 成都理工大学 | 一种乙酸自热重整制氢的类水滑石型铁促进镍基催化剂及制备方法 |
| CN109745993A (zh) * | 2017-11-01 | 2019-05-14 | 中国石油天然气股份有限公司 | 一种介孔本体型Mo-Ni加氢脱氧催化剂的制备方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2767221A (en) * | 1953-06-11 | 1956-10-16 | Shell Dev | Production of unsaturated alcohols |
| CN101544355A (zh) * | 2009-05-05 | 2009-09-30 | 北京化工大学 | 一种层状双羟基复合金属氧化物花状微球的水热制备方法 |
| CN101733105B (zh) * | 2009-11-27 | 2012-11-21 | 昆明理工大学 | 以二元类水滑石为前驱体制备的羰基硫水解催化剂及制备方法 |
| CN101797492B (zh) * | 2010-04-16 | 2012-04-04 | 北京化工大学 | 一种层状双羟基复合金属氢氧化物多孔微球的制备方法 |
| CN102078813A (zh) * | 2010-12-13 | 2011-06-01 | 昆明理工大学 | 一种低温下水解羰基硫的催化剂及其制备方法 |
| CN102407121B (zh) * | 2011-10-18 | 2013-07-24 | 华南理工大学 | 一种以X/Ni/Al类水滑石为前驱体的加氢催化剂的制备方法 |
| CN103464165A (zh) * | 2013-08-23 | 2013-12-25 | 东莞上海大学纳米技术研究院 | 一种蜂窝状铈铜复合多元氧化物催化剂、制备方法及应用 |
| CN105289619B (zh) * | 2015-11-19 | 2018-06-29 | 中科合成油技术有限公司 | 镍基催化剂及其制备方法与在5-羟甲基糠醛加氢中的应用 |
| CN109261152A (zh) * | 2018-10-08 | 2019-01-25 | 天津理工大学 | 一种催化糠醛还原的负载型催化剂及其制备方法及应用 |
| CN110180553A (zh) * | 2019-04-04 | 2019-08-30 | 沈阳化工大学 | 一种高效糠醛气相转化为2-甲基呋喃催化剂的方法 |
| CN109942517A (zh) * | 2019-04-19 | 2019-06-28 | 信阳师范学院 | 一种金属氢氧化物催化糠醛转移加氢制备糠醇的方法 |
-
2019
- 2019-12-20 CN CN201911328809.6A patent/CN113000049B/zh active Active
-
2020
- 2020-11-11 WO PCT/CN2020/128198 patent/WO2021120928A1/zh active Application Filing
- 2020-11-11 CN CN202080087000.3A patent/CN114829004B/zh active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103962140A (zh) * | 2014-05-12 | 2014-08-06 | 北京化工大学 | 一种微球形中空结构镍基加氢催化剂及其制备方法 |
| CN107282050A (zh) * | 2017-07-14 | 2017-10-24 | 成都理工大学 | 一种乙酸自热重整制氢的类水滑石型铁促进镍基催化剂及制备方法 |
| CN109745993A (zh) * | 2017-11-01 | 2019-05-14 | 中国石油天然气股份有限公司 | 一种介孔本体型Mo-Ni加氢脱氧催化剂的制备方法 |
Non-Patent Citations (1)
| Title |
|---|
| T.M. JYOTHI等: "Influence of acid–base properties of mixed oxides derived from hydrotalcite-like precursors in the transfer hydrogenation of propiophenone" * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN113000049A (zh) | 2021-06-22 |
| CN113000049B (zh) | 2022-12-23 |
| CN114829004B (zh) | 2024-02-27 |
| WO2021120928A1 (zh) | 2021-06-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN114829004B (zh) | 一种制备Ni-X基氧化物催化剂的方法及其在转移加氢中的应用 | |
| JP7019813B2 (ja) | アセトフェノンの水素化によってα－フェニルエタノールを製造するための触媒、その製造方法および応用 | |
| CN107486234B (zh) | 用于合成气直接转化制备轻质芳烃的催化剂及其制备方法 | |
| CN101455964B (zh) | 一种镍基金属负载型催化剂的制备方法 | |
| CN112169799B (zh) | 采用铁基催化剂进行二氧化碳加氢合成低碳烯烃的方法 | |
| CN109225228B (zh) | 一种镍基核壳结构纳米催化剂及其制备方法与应用 | |
| CN113209958B (zh) | 一种掺杂Zn元素的固溶体催化剂及制备和应用 | |
| CN105727944B (zh) | 一种ZrO2纳米片负载钌催化剂的制备方法 | |
| CN110327933A (zh) | 二氧化碳加氢制备甲醇的催化剂及其制备方法和应用 | |
| CN111905755B (zh) | 一种用于2，2，4，4-四甲基-1，3-环丁二酮加氢的催化剂及其制备方法、应用 | |
| CN111013592A (zh) | 一种具有插层结构的水滑石镍基纳米催化剂及其制备方法与应用 | |
| CN109847756B (zh) | 一种中空结构的镍基纳米催化剂及其制备方法与应用 | |
| CN112547067A (zh) | 用于浆态床甲烷合成反应催化剂的制备方法 | |
| CN105148939A (zh) | 一种高分散负载型PtCo纳米合金催化剂及其制备方法和应用 | |
| CN111686740B (zh) | 合成甲醇催化剂的制法 | |
| CN103331160B (zh) | 基于非贵重金属的高分散铜基催化剂的制备方法 | |
| CN110368953A (zh) | 一种复合氧化物负载铂催化剂及其制备和应用 | |
| CN113828319B (zh) | 一种Cu-Zn-M的复合氧化物催化剂及其制备方法和用途 | |
| CN113952960A (zh) | 一种由合成气制低碳醇的Co-CeO2催化剂、制备方法及应用 | |
| CN110893347A (zh) | 低温高活性镍基双金属甲烷化催化剂及其制备方法与应用 | |
| CN107824191A (zh) | 一种基于三元铜基微球的氧化锆载体催化剂及其制备方法 | |
| CN107442120A (zh) | 一种Cu/ZrO2催化剂及其制备方法和用途 | |
| CN110935478A (zh) | 合成甲醇催化剂的制备方法 | |
| CN112588290B (zh) | 一种草酸酯加氢制乙二醇用铜基催化剂及其制备方法 | |
| CN116510736B (zh) | 一种负载型纳米铜基催化剂及其制备方法与应用 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |