SA113340550B1 - محفزات اختزال متضمنة بلاتينيوم ورديوم - Google Patents
محفزات اختزال متضمنة بلاتينيوم ورديوم Download PDFInfo
- Publication number
- SA113340550B1 SA113340550B1 SA113340550A SA113340550A SA113340550B1 SA 113340550 B1 SA113340550 B1 SA 113340550B1 SA 113340550 A SA113340550 A SA 113340550A SA 113340550 A SA113340550 A SA 113340550A SA 113340550 B1 SA113340550 B1 SA 113340550B1
- Authority
- SA
- Saudi Arabia
- Prior art keywords
- rhodium
- platinum
- catalyst
- zirconia
- carrier
- Prior art date
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 title claims abstract description 248
- 239000010948 rhodium Substances 0.000 title claims abstract description 122
- 229910052697 platinum Inorganic materials 0.000 title claims abstract description 121
- 239000003054 catalyst Substances 0.000 title claims abstract description 116
- 229910052703 rhodium Inorganic materials 0.000 title claims abstract description 116
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 title abstract description 108
- 230000009467 reduction Effects 0.000 title description 6
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims abstract description 124
- 239000000203 mixture Substances 0.000 claims abstract description 26
- 238000000034 method Methods 0.000 claims abstract description 24
- 239000011148 porous material Substances 0.000 claims abstract description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 12
- 229910002076 stabilized zirconia Inorganic materials 0.000 claims abstract description 9
- 229910052751 metal Inorganic materials 0.000 claims description 59
- 239000002184 metal Substances 0.000 claims description 59
- 239000001257 hydrogen Substances 0.000 claims description 52
- 229910052739 hydrogen Inorganic materials 0.000 claims description 52
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 42
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 40
- 239000002245 particle Substances 0.000 claims description 34
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 31
- 239000011707 mineral Substances 0.000 claims description 31
- 239000000758 substrate Substances 0.000 claims description 26
- 125000001183 hydrocarbyl group Chemical class 0.000 claims description 25
- 239000000463 material Substances 0.000 claims description 24
- 239000001361 adipic acid Substances 0.000 claims description 21
- 235000011037 adipic acid Nutrition 0.000 claims description 20
- -1 acyl oxy hydrogen Chemical compound 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 150000002500 ions Chemical class 0.000 claims description 14
- 230000008569 process Effects 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 11
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 10
- 229910052721 tungsten Inorganic materials 0.000 claims description 10
- 239000010937 tungsten Substances 0.000 claims description 10
- 150000002739 metals Chemical class 0.000 claims description 9
- 150000002596 lactones Chemical class 0.000 claims description 8
- 239000000956 alloy Substances 0.000 claims description 7
- 229910045601 alloy Inorganic materials 0.000 claims description 7
- 239000002638 heterogeneous catalyst Substances 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 239000012876 carrier material Substances 0.000 claims description 6
- 238000013461 design Methods 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 239000002019 doping agent Substances 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 229910021645 metal ion Inorganic materials 0.000 claims description 2
- BALRIWPTGHDDFF-UHFFFAOYSA-N rhodium Chemical compound [Rh].[Rh] BALRIWPTGHDDFF-UHFFFAOYSA-N 0.000 claims 11
- 230000001681 protective effect Effects 0.000 claims 2
- 241000196324 Embryophyta Species 0.000 claims 1
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 claims 1
- 238000005275 alloying Methods 0.000 claims 1
- 208000027697 autoimmune lymphoproliferative syndrome due to CTLA4 haploinsuffiency Diseases 0.000 claims 1
- ODOJGYBXTZYZCP-UHFFFAOYSA-N molybdenum palladium Chemical compound [Mo].[Pd].[Pd].[Pd] ODOJGYBXTZYZCP-UHFFFAOYSA-N 0.000 claims 1
- 238000004416 surface enhanced Raman spectroscopy Methods 0.000 claims 1
- 229910044991 metal oxide Inorganic materials 0.000 abstract description 12
- 150000001735 carboxylic acids Chemical class 0.000 abstract description 5
- 239000002131 composite material Substances 0.000 abstract description 4
- 239000000243 solution Substances 0.000 description 23
- 150000001875 compounds Chemical class 0.000 description 21
- 238000006392 deoxygenation reaction Methods 0.000 description 16
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- DSLZVSRJTYRBFB-LLEIAEIESA-N D-glucaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O DSLZVSRJTYRBFB-LLEIAEIESA-N 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 239000000969 carrier Substances 0.000 description 10
- 238000001035 drying Methods 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- 230000002829 reductive effect Effects 0.000 description 9
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 8
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- 229910052750 molybdenum Inorganic materials 0.000 description 8
- 239000011733 molybdenum Substances 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 239000012298 atmosphere Substances 0.000 description 7
- 150000001991 dicarboxylic acids Chemical class 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 238000011068 loading method Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 5
- 125000004423 acyloxy group Chemical group 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- QRFNDAVXJCGLFB-GJPGBQJBSA-N (3r,3ar,6s,6ar)-3,6-dihydroxy-3,3a,6,6a-tetrahydrofuro[3,2-b]furan-2,5-dione Chemical compound O1C(=O)[C@H](O)[C@H]2OC(=O)[C@@H](O)[C@H]21 QRFNDAVXJCGLFB-GJPGBQJBSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
- 235000015107 ale Nutrition 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- NOWPEMKUZKNSGG-UHFFFAOYSA-N azane;platinum(2+) Chemical compound N.N.N.N.[Pt+2] NOWPEMKUZKNSGG-UHFFFAOYSA-N 0.000 description 4
- 239000010779 crude oil Substances 0.000 description 4
- 238000006356 dehydrogenation reaction Methods 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- 230000008021 deposition Effects 0.000 description 4
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 4
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 4
- 238000005470 impregnation Methods 0.000 description 4
- 238000004806 packaging method and process Methods 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- MFDMDFYYLGDEGT-UHFFFAOYSA-K [Rh](Cl)(Cl)Cl.[Rh] Chemical compound [Rh](Cl)(Cl)Cl.[Rh] MFDMDFYYLGDEGT-UHFFFAOYSA-K 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- PXXKQOPKNFECSZ-UHFFFAOYSA-N platinum rhodium Chemical compound [Rh].[Pt] PXXKQOPKNFECSZ-UHFFFAOYSA-N 0.000 description 3
- NWAHZABTSDUXMJ-UHFFFAOYSA-N platinum(2+);dinitrate Chemical compound [Pt+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O NWAHZABTSDUXMJ-UHFFFAOYSA-N 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- VXNYVYJABGOSBX-UHFFFAOYSA-N rhodium(3+);trinitrate Chemical compound [Rh+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VXNYVYJABGOSBX-UHFFFAOYSA-N 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- XECPAIJNBXCOBO-MMPJQOAZSA-N D-glucaro-1,4-lactone Chemical compound OC(=O)[C@@H](O)[C@H]1OC(=O)[C@H](O)[C@H]1O XECPAIJNBXCOBO-MMPJQOAZSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000917703 Leia Species 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
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- 150000001721 carbon Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000012018 catalyst precursor Substances 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
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- 125000005843 halogen group Chemical group 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
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- 239000000543 intermediate Substances 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
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- 239000002923 metal particle Substances 0.000 description 2
- 238000001465 metallisation Methods 0.000 description 2
- CSJDCSCTVDEHRN-UHFFFAOYSA-N methane;molecular oxygen Chemical compound C.O=O CSJDCSCTVDEHRN-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
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- XECPAIJNBXCOBO-XHGCLVTGSA-N (2r)-2-[(2s,3r,4s)-3,4-dihydroxy-5-oxooxolan-2-yl]-2-hydroxyacetic acid Chemical compound OC(=O)[C@H](O)[C@H]1OC(=O)[C@@H](O)[C@H]1O XECPAIJNBXCOBO-XHGCLVTGSA-N 0.000 description 1
- IUQNAGFJAIOCNL-UHFFFAOYSA-N 2,3,4-trihydroxy-5-oxohexanedioic acid Chemical compound OC(=O)C(O)C(O)C(O)C(=O)C(O)=O IUQNAGFJAIOCNL-UHFFFAOYSA-N 0.000 description 1
- DMCRIWYMGHUFJK-UHFFFAOYSA-N 2,3,5-trihydroxy-4-oxohexanedioic acid Chemical compound OC(=O)C(O)C(O)C(=O)C(O)C(O)=O DMCRIWYMGHUFJK-UHFFFAOYSA-N 0.000 description 1
- HLMXWUYOTWZKHB-UHFFFAOYSA-N 2-aminoethanol;platinum Chemical compound [Pt].NCCO HLMXWUYOTWZKHB-UHFFFAOYSA-N 0.000 description 1
- KWSLGOVYXMQPPX-UHFFFAOYSA-N 5-[3-(trifluoromethyl)phenyl]-2h-tetrazole Chemical compound FC(F)(F)C1=CC=CC(C2=NNN=N2)=C1 KWSLGOVYXMQPPX-UHFFFAOYSA-N 0.000 description 1
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- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 239000002028 Biomass Substances 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N Bisphenol A Natural products C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
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- 101150105088 Dele1 gene Proteins 0.000 description 1
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- 239000004677 Nylon Substances 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
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- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
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- UYVZCGGFTICJMW-UHFFFAOYSA-N [Ir].[Au] Chemical compound [Ir].[Au] UYVZCGGFTICJMW-UHFFFAOYSA-N 0.000 description 1
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- 150000001408 amides Chemical class 0.000 description 1
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- 230000002210 biocatalytic effect Effects 0.000 description 1
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- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
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- CETPSERCERDGAM-UHFFFAOYSA-N ceric oxide Chemical compound O=[Ce]=O CETPSERCERDGAM-UHFFFAOYSA-N 0.000 description 1
- 229910000422 cerium(IV) oxide Inorganic materials 0.000 description 1
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- QCDFRRQWKKLIKV-UHFFFAOYSA-M chloroplatinum Chemical compound [Pt]Cl QCDFRRQWKKLIKV-UHFFFAOYSA-M 0.000 description 1
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- 238000003795 desorption Methods 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 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
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
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- 239000000834 fixative Substances 0.000 description 1
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- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- MMHWNKSVQDCUDE-UHFFFAOYSA-N hexanedioic acid;terephthalic acid Chemical compound OC(=O)CCCCC(O)=O.OC(=O)C1=CC=C(C(O)=O)C=C1 MMHWNKSVQDCUDE-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
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- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
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- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
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- 238000005259 measurement Methods 0.000 description 1
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- 239000000178 monomer Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- VXAPDXVBDZRZKP-UHFFFAOYSA-N nitric acid phosphoric acid Chemical compound O[N+]([O-])=O.OP(O)(O)=O VXAPDXVBDZRZKP-UHFFFAOYSA-N 0.000 description 1
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- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
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- 230000037361 pathway Effects 0.000 description 1
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- SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 1
- MWZNPHHDRLXXHO-UHFFFAOYSA-N rhodium;hydrate Chemical compound O.[Rh] MWZNPHHDRLXXHO-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
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- 229910001379 sodium hypophosphite Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
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- 230000003068 static effect Effects 0.000 description 1
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- 238000003756 stirring Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- FBEIPJNQGITEBL-UHFFFAOYSA-J tetrachloroplatinum Chemical compound Cl[Pt](Cl)(Cl)Cl FBEIPJNQGITEBL-UHFFFAOYSA-J 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- 229910021654 trace metal Inorganic materials 0.000 description 1
- RUDFQVOCFDJEEF-UHFFFAOYSA-N yttrium(III) oxide Inorganic materials [O-2].[O-2].[O-2].[Y+3].[Y+3] RUDFQVOCFDJEEF-UHFFFAOYSA-N 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
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- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/46—Ruthenium, rhodium, osmium or iridium
- B01J23/464—Rhodium
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- 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
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
- B01J21/063—Titanium; Oxides or hydroxides thereof
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
- B01J21/066—Zirconium or hafnium; Oxides or hydroxides thereof
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- 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
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
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- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/61—Surface area
- B01J35/613—10-100 m2/g
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/64—Pore diameter
- B01J35/651—50-500 nm
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- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/0201—Impregnation
- B01J37/0205—Impregnation in several steps
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/024—Multiple impregnation or coating
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
-
- 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
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/18—Carbon
-
- 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
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/56—Platinum group metals
- B01J23/58—Platinum group metals with alkali- or alkaline earth metals
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- 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
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nanotechnology (AREA)
Applications Claiming Priority (1)
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| WO2013090031A2 (en) | 2011-12-14 | 2013-06-20 | Rennovia, Inc. | Water concentration reduction process |
| WO2013126250A1 (en) | 2012-02-23 | 2013-08-29 | Rennovia, Inc. | Production of caprolactam from adipic acid |
| WO2015084265A1 (en) * | 2013-12-04 | 2015-06-11 | Agency For Science, Technology And Research | Chemical process to convert mucic acid to adipic acid |
| FI3878552T3 (fi) | 2014-04-29 | 2023-04-25 | Archer Daniels Midland Co | Prosessi aldoosin selektiivistä hapettumista varten |
| US11253839B2 (en) | 2014-04-29 | 2022-02-22 | Archer-Daniels-Midland Company | Shaped porous carbon products |
| BR112017005823B1 (pt) | 2014-09-29 | 2023-03-28 | Archer-Daniels-Midland Company | Processo para a preparação de um extrato |
| US10464048B2 (en) | 2015-10-28 | 2019-11-05 | Archer-Daniels-Midland Company | Porous shaped metal-carbon products |
| US10722867B2 (en) | 2015-10-28 | 2020-07-28 | Archer-Daniels-Midland Company | Porous shaped carbon products |
| EP3402787A4 (en) | 2016-01-13 | 2019-11-27 | Stora Enso Oyj | PROCESS FOR THE PREPARATION OF 2,5-FURANDIC ACETIC ACID AND INTERMEDIATES AND DERIVATIVES THEREOF |
| FI20165451A (fi) * | 2016-05-31 | 2017-12-01 | Teknologian Tutkimuskeskus Vtt Oy | Jatkuvatoiminen menetelmä mukonihapon valmistamiseksi aldaarihaposta |
| WO2018048394A1 (en) * | 2016-09-07 | 2018-03-15 | South Dakota Board Of Regents | Thermally stabilized redox materials and applications thereof |
| SG11201913469PA (en) | 2017-07-12 | 2020-01-30 | Stora Enso Oyj | Purified 2,5-furandicarboxylic acid pathway products |
| JP7158953B2 (ja) * | 2017-08-18 | 2022-10-24 | 中国石油化工股▲ふん▼有限公司 | 重質芳香族炭化水素から軽質芳香族炭化水素を製造するための触媒、その製造方法及び適用 |
| CN107556186B (zh) * | 2017-10-17 | 2019-06-18 | 北京大学 | 一种由葡萄糖二酸制备己二酸的方法 |
| KR102829802B1 (ko) * | 2018-08-29 | 2025-07-03 | 현대자동차주식회사 | 아디픽산의 제조방법 |
| CN112441912B (zh) * | 2019-08-28 | 2023-05-05 | 中国石油化工股份有限公司 | 一种低碳饱和脂肪酸的制备方法 |
| KR102310957B1 (ko) * | 2019-11-13 | 2021-10-12 | 한국과학기술원 | 액상화합물 기반 수소저장용 탈수소화 반응 촉매 및 그 제조방법 |
| SE2330605A1 (en) * | 2023-12-21 | 2025-06-22 | Stora Enso Oyj | Heterogenous pt-based catalyst |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53144506A (en) | 1977-05-20 | 1978-12-15 | Noguchi Kenkyusho | Method of reducing polyalcohols |
| US4400468A (en) | 1981-10-05 | 1983-08-23 | Hydrocarbon Research Inc. | Process for producing adipic acid from biomass |
| US5487987A (en) | 1993-09-16 | 1996-01-30 | Purdue Research Foundation | Synthesis of adipic acid from biomass-derived carbon sources |
| US5516960A (en) | 1994-08-02 | 1996-05-14 | Board Of Regents, The University Of Texas System | Process for producing hydrocarbon fuels |
| US5945369A (en) * | 1994-12-09 | 1999-08-31 | Kabushiki Kaisha Toyota Chuo Kenkyusho | Catalyst for purifying exhaust gases and process for producing the same |
| IT1271312B (it) * | 1994-12-21 | 1997-05-27 | Enirisorse Spa | Procedimento sol-gel per ottenere sfere,microsfere o rivestimenti di monoliti a forma cellulare,costituiti da ossido di zirconio puro o misto ad altri ossidi,utili come catalizzatori o supporti per catalizzatori |
| JP2001278822A (ja) * | 1999-11-05 | 2001-10-10 | Asahi Kasei Corp | ジオール混合物の製造方法 |
| FR2818638B1 (fr) * | 2000-12-27 | 2003-02-07 | Rhodia Polyamide Intermediates | Procede de preparation d'acides carboxyliques par carbonylation au palladium |
| JP4032652B2 (ja) * | 2001-02-23 | 2008-01-16 | 株式会社豊田中央研究所 | 複合酸化物粉末及びその製造方法 |
| US7022644B2 (en) * | 2002-02-20 | 2006-04-04 | Engelhard Corporation | Hydrogen sulfide-suppressing catalyst compositions |
| JP2005138024A (ja) * | 2003-11-06 | 2005-06-02 | Sekisui Chem Co Ltd | 水素化芳香族化合物からの脱水素反応用触媒とその触媒を利用した水素製造方法 |
| US7220701B2 (en) * | 2003-11-24 | 2007-05-22 | Exxonmobil Chemical Patents Inc. | Catalyst and process for selective hydrogenation |
| JP2006043654A (ja) * | 2004-08-09 | 2006-02-16 | Toyota Motor Corp | 排ガス浄化触媒及びその製造方法 |
| JP2006159021A (ja) * | 2004-12-03 | 2006-06-22 | Toyota Motor Corp | 排ガス浄化用触媒 |
| US20090305882A1 (en) * | 2006-02-03 | 2009-12-10 | Saint-Gobain Ceramics & Plastics, Inc. | Articles Comprising Tetragonal Zirconia and Methods of Making the Same |
| US20070215484A1 (en) | 2006-03-15 | 2007-09-20 | Peterson Otis G | Electrochemical conversion of polyalcohols to hydrocarbons |
| EP1920830A1 (en) * | 2006-11-08 | 2008-05-14 | L'AIR LIQUIDE, Société Anonyme pour l'Etude et l'Exploitation des Procédés Georges Claude | Group VIII and ceria/zirconia containing catalysts for catalytic hydrocarbon reforming or oxidation |
| JP4752977B2 (ja) * | 2008-09-02 | 2011-08-17 | 日産自動車株式会社 | 排気ガス浄化用触媒及びその製造方法 |
| US8669397B2 (en) * | 2009-06-13 | 2014-03-11 | Rennovia, Inc. | Production of adipic acid and derivatives from carbohydrate-containing materials |
| EP2440514B1 (en) * | 2009-06-13 | 2018-08-22 | Archer-Daniels-Midland Company | Production of adipic acid and derivatives from carbohydrate-containing materials |
| WO2011109051A1 (en) * | 2010-03-05 | 2011-09-09 | Rennovia, Inc. | Adipic acid composition |
| WO2013090031A2 (en) | 2011-12-14 | 2013-06-20 | Rennovia, Inc. | Water concentration reduction process |
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| IN2014DN10247A (enExample) | 2015-08-07 |
| AR114347A2 (es) | 2020-08-26 |
| KR20150018815A (ko) | 2015-02-24 |
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| ES2822593T3 (es) | 2021-05-04 |
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| CN104582847A (zh) | 2015-04-29 |
| US9468908B2 (en) | 2016-10-18 |
| US20130310605A1 (en) | 2013-11-21 |
| EP2849884A1 (en) | 2015-03-25 |
| SG11201407554UA (en) | 2014-12-30 |
| DK2849884T3 (da) | 2020-10-12 |
| JP6200946B2 (ja) | 2017-09-20 |
| WO2013173372A1 (en) | 2013-11-21 |
| EP2849884B1 (en) | 2020-09-09 |
| HK1208197A1 (en) | 2016-02-26 |
| JP2015523197A (ja) | 2015-08-13 |
| EA028465B1 (ru) | 2017-11-30 |
| EA201492103A1 (ru) | 2015-02-27 |
| BR112014028474A2 (pt) | 2017-06-27 |
| BR112014028474B1 (pt) | 2021-12-07 |
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