RU2009122732A - Способ гидроокисления с использованием катализатора, полученного из кластерного комплекса золота - Google Patents
Способ гидроокисления с использованием катализатора, полученного из кластерного комплекса золота Download PDFInfo
- Publication number
- RU2009122732A RU2009122732A RU2009122732/04A RU2009122732A RU2009122732A RU 2009122732 A RU2009122732 A RU 2009122732A RU 2009122732/04 A RU2009122732/04 A RU 2009122732/04A RU 2009122732 A RU2009122732 A RU 2009122732A RU 2009122732 A RU2009122732 A RU 2009122732A
- Authority
- RU
- Russia
- Prior art keywords
- pph
- gold
- aupph
- catalyst
- pph3
- Prior art date
Links
- 239000003054 catalyst Substances 0.000 title claims abstract 11
- 238000000034 method Methods 0.000 title claims abstract 11
- 239000010931 gold Substances 0.000 claims abstract 41
- 239000000203 mixture Substances 0.000 claims abstract 30
- 229910052737 gold Inorganic materials 0.000 claims abstract 11
- 239000003446 ligand Substances 0.000 claims abstract 11
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims abstract 9
- 239000002245 particle Substances 0.000 claims abstract 6
- 239000012018 catalyst precursor Substances 0.000 claims abstract 4
- 239000002105 nanoparticle Substances 0.000 claims abstract 4
- 239000010936 titanium Substances 0.000 claims abstract 4
- 229910052709 silver Inorganic materials 0.000 claims abstract 3
- 239000004332 silver Substances 0.000 claims abstract 3
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims abstract 2
- 150000001408 amides Chemical class 0.000 claims abstract 2
- 150000001412 amines Chemical class 0.000 claims abstract 2
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract 2
- 239000013078 crystal Substances 0.000 claims abstract 2
- 150000004820 halides Chemical class 0.000 claims abstract 2
- 238000010438 heat treatment Methods 0.000 claims abstract 2
- 150000003949 imides Chemical class 0.000 claims abstract 2
- 150000002466 imines Chemical class 0.000 claims abstract 2
- 150000002903 organophosphorus compounds Chemical class 0.000 claims abstract 2
- 239000002243 precursor Substances 0.000 claims abstract 2
- 239000000126 substance Substances 0.000 claims abstract 2
- 150000007944 thiolates Chemical class 0.000 claims abstract 2
- 150000003573 thiols Chemical class 0.000 claims abstract 2
- 229910052719 titanium Inorganic materials 0.000 claims abstract 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 11
- 150000001336 alkenes Chemical class 0.000 claims 6
- 239000003085 diluting agent Substances 0.000 claims 6
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 4
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims 2
- 239000007789 gas Substances 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000007788 liquid Substances 0.000 claims 2
- 239000007791 liquid phase Substances 0.000 claims 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000012071 phase Substances 0.000 claims 2
- LWJHSQQHGRQCKO-UHFFFAOYSA-N 1-prop-2-enoxypropane Chemical compound CCCOCC=C LWJHSQQHGRQCKO-UHFFFAOYSA-N 0.000 claims 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 claims 1
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 claims 1
- RMZIOVJHUJAAEY-UHFFFAOYSA-N Allyl butyrate Chemical compound CCCC(=O)OCC=C RMZIOVJHUJAAEY-UHFFFAOYSA-N 0.000 claims 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims 1
- -1 aliphatic alcohols Chemical class 0.000 claims 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims 1
- 229910052786 argon Inorganic materials 0.000 claims 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 229910002092 carbon dioxide Inorganic materials 0.000 claims 1
- 239000001569 carbon dioxide Substances 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 238000000151 deposition Methods 0.000 claims 1
- 150000001993 dienes Chemical class 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- 239000001307 helium Substances 0.000 claims 1
- 229910052734 helium Inorganic materials 0.000 claims 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 229910052741 iridium Inorganic materials 0.000 claims 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims 1
- JFZUABNDWZQLIJ-UHFFFAOYSA-N methyl 2-[(2-chloroacetyl)amino]benzoate Chemical compound COC(=O)C1=CC=CC=C1NC(=O)CCl JFZUABNDWZQLIJ-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 150000005673 monoalkenes Chemical class 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 229910000510 noble metal Inorganic materials 0.000 claims 1
- 229910052762 osmium Inorganic materials 0.000 claims 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 229930015698 phenylpropene Natural products 0.000 claims 1
- 229910052697 platinum Inorganic materials 0.000 claims 1
- 229920000728 polyester Polymers 0.000 claims 1
- 229920000570 polyether Polymers 0.000 claims 1
- 229920005862 polyol Polymers 0.000 claims 1
- 150000003077 polyols Chemical class 0.000 claims 1
- POSICDHOUBKJKP-UHFFFAOYSA-N prop-2-enoxybenzene Chemical compound C=CCOC1=CC=CC=C1 POSICDHOUBKJKP-UHFFFAOYSA-N 0.000 claims 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 claims 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 229910052703 rhodium Inorganic materials 0.000 claims 1
- 239000010948 rhodium Substances 0.000 claims 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims 1
- 229910052707 ruthenium Inorganic materials 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 230000008021 deposition Effects 0.000 abstract 1
- HASCQPSFPAKVEK-UHFFFAOYSA-N dimethyl(phenyl)phosphine Chemical compound CP(C)C1=CC=CC=C1 HASCQPSFPAKVEK-UHFFFAOYSA-N 0.000 abstract 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
-
- 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
- B01J23/48—Silver or gold
- B01J23/52—Gold
-
- 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
- B01J23/66—Silver or gold
-
- 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
- B01J29/89—Silicates, aluminosilicates or borosilicates of titanium, zirconium or hafnium
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/1691—Coordination polymers, e.g. metal-organic frameworks [MOF]
-
- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/20—Catalysts, in general, characterised by their form or physical properties characterised by their non-solid state
- B01J35/23—Catalysts, in general, characterised by their form or physical properties characterised by their non-solid state in a colloidal state
-
- 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
- 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
-
- 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
- B01J37/0203—Impregnation the impregnation liquid containing organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/04—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen
- C07D301/08—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen in the gaseous phase
- C07D301/10—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen in the gaseous phase with catalysts containing silver or gold
-
- 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
- B01J2229/00—Aspects of molecular sieve catalysts not covered by B01J29/00
- B01J2229/10—After treatment, characterised by the effect to be obtained
- B01J2229/18—After treatment, characterised by the effect to be obtained to introduce other elements into or onto the molecular sieve itself
- B01J2229/186—After treatment, characterised by the effect to be obtained to introduce other elements into or onto the molecular sieve itself not in framework positions
-
- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/32—Addition reactions to C=C or C-C triple bonds
- B01J2231/324—Cyclisations via conversion of C-C multiple to single or less multiple bonds, e.g. cycloadditions
- B01J2231/325—Cyclopropanations
-
- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/70—Oxidation reactions, e.g. epoxidation, (di)hydroxylation, dehydrogenation and analogues
- B01J2231/72—Epoxidation
-
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/10—Complexes comprising metals of Group I (IA or IB) as the central metal
- B01J2531/18—Gold
-
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/60—Complexes comprising metals of Group VI (VIA or VIB) as the central metal
- B01J2531/62—Chromium
-
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/84—Metals of the iron group
- B01J2531/842—Iron
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Compounds (AREA)
Abstract
1. Каталитическая композиция, содержащая наночастицы золота, осажденные на частицах нанопористого титаносиликатного носителя, причем катализатор получают способом, включающим осаждение кластерного комплекса золото-лиганд на нанопористый титаносиликатный носитель в условиях, достаточных для образования предшественника катализатора, и последующий нагрев и/или химическую обработку предшественника катализатора в условиях, достаточных для образования катализатора. ! 2. Композиция по п.1, в которой наночастицы золота имеют срединный размер частиц в диапазоне от 0,8 нм до менее 8 нм. ! 3. Композиция по п.1, в которой золото загружают на носитель в количестве более 10 ч./млн и менее 20000 ч./млн в расчете на общую массу катализатора. ! 4. Композиция по п.1, в которой нанопористый титансодержащий носитель представляет собой нанопористый титаносиликат, выбранный из группы, состоящей из TS-1, TS-2, Ti-бета, Ti-MCM-41, Ti-MCM-48, Ti-SBA-15 и Ti-SBA-3. ! 5. Композиция по п.4, в которой нанопористый титаносиликат имеет MFI кристаллическую структуру и атомное отношение Si:Ti более 5:1 и менее 1000:1. ! 6. Композиция по п.1, в которой лиганд выбран из фосфорорганических соединений, тиолатов, тиолов, аминов, иминов, амидов, имидов, монооксида углерода, галогенидов и их смесей. ! 7. Композиция по п.1, в которой кластер золота выбран из группы, состоящей из Au3, Au4, Au5, Au6, Au7, Au8, Au9, Au10, Au11, Au12, Au13, Au(20±2), Au(55±5), Au(101±10) и их смесей, и кластер необязательно дополнительно содержит серебро. ! 8. Композиция по п.7, в которой кластерный комплекс золото-лиганд выбран из (Ph3PAu)3OBF4, [(AuPPh3)3O]PF6, Au5(PPh3)4Cl, Au6(PPh3)6(BF4)2, Au6(PPh3)6(NO3)2, Au6(PPh3)6(PF6)2, Au8(PPh3)8(NO3)2, Au8(PPh3)7(NO3)2, Au9(PPh3)8(NO3)3, Au10(PPh3)5(C6F5)4, Au11Cl3{(m-CF3C6H4)3P}7, Au11(PPh3)7(PF6)3, [Au13(PMe2Ph)10Cl2](PF6
Claims (17)
1. Каталитическая композиция, содержащая наночастицы золота, осажденные на частицах нанопористого титаносиликатного носителя, причем катализатор получают способом, включающим осаждение кластерного комплекса золото-лиганд на нанопористый титаносиликатный носитель в условиях, достаточных для образования предшественника катализатора, и последующий нагрев и/или химическую обработку предшественника катализатора в условиях, достаточных для образования катализатора.
2. Композиция по п.1, в которой наночастицы золота имеют срединный размер частиц в диапазоне от 0,8 нм до менее 8 нм.
3. Композиция по п.1, в которой золото загружают на носитель в количестве более 10 ч./млн и менее 20000 ч./млн в расчете на общую массу катализатора.
4. Композиция по п.1, в которой нанопористый титансодержащий носитель представляет собой нанопористый титаносиликат, выбранный из группы, состоящей из TS-1, TS-2, Ti-бета, Ti-MCM-41, Ti-MCM-48, Ti-SBA-15 и Ti-SBA-3.
5. Композиция по п.4, в которой нанопористый титаносиликат имеет MFI кристаллическую структуру и атомное отношение Si:Ti более 5:1 и менее 1000:1.
6. Композиция по п.1, в которой лиганд выбран из фосфорорганических соединений, тиолатов, тиолов, аминов, иминов, амидов, имидов, монооксида углерода, галогенидов и их смесей.
7. Композиция по п.1, в которой кластер золота выбран из группы, состоящей из Au3, Au4, Au5, Au6, Au7, Au8, Au9, Au10, Au11, Au12, Au13, Au(20±2), Au(55±5), Au(101±10) и их смесей, и кластер необязательно дополнительно содержит серебро.
8. Композиция по п.7, в которой кластерный комплекс золото-лиганд выбран из (Ph3PAu)3OBF4, [(AuPPh3)3O]PF6, Au5(PPh3)4Cl, Au6(PPh3)6(BF4)2, Au6(PPh3)6(NO3)2, Au6(PPh3)6(PF6)2, Au8(PPh3)8(NO3)2, Au8(PPh3)7(NO3)2, Au9(PPh3)8(NO3)3, Au10(PPh3)5(C6F5)4, Au11Cl3{(m-CF3C6H4)3P}7, Au11(PPh3)7(PF6)3, [Au13(PMe2Ph)10Cl2](PF6)3, Au13(PPh3)4[S(CH2)11(CH3)]4, [Au13(PPh2CH2PPh2)6](NO3)4, Au55(Ph2PC6H4SO3Na·2H2O)12Cl6, Au55(PPh3)12Cl6, кластерных комплексов золото-лиганд, имеющих средний размер частиц золота примерно 1,4 нм, и их смесей; причем в вышеуказанных комплексах Ph означает фенил и Me означает метил.
9. Композиция по п.1, в которой кластерный комплекс золото-лиганд дополнительно содержит благородный металл, выбранный из группы, состоящей из рутения, родия, палладия, осмия, иридия и платины и их смесей, и необязательно дополнительно содержит серебро.
10. Композиция по п.8, в которой кластерный комплекс золото-лиганд выбран из [(PPh3)(CO)Pt(AuPPh3)6](PF6)2, [(PPh3)Pt(AuPPh3)6](NO3)2, [Pd(AuPPh3)8](NO3)2, [H4(PPh3)2Re(AuPPh3)5](PF6)2, [PPh3Pt(AuPPh3)6](PF6)2, [H(PPh3)Pt(AuPPh3)7](NO3), [Pt(AuPPh3)7(Ag)2](NO3)3, [Pd(AuPPh3)8](PF6)2, [Pt(AuPPh3)8](NO3)2, [Pt(AuPPh3)8](PF6)2, [(PPh3)Pt(AuPPh3)8(Ag)](NO3)2 и [Pt2(AuPPh3)10(Ag)13]Cl7 и их смесей.
11. Способ получения оксида олефина, включающий контактирование олефина, имеющего, по меньшей мере, три атома углерода, с кислородом в присутствии водорода и в присутствии катализатора, имеющего состав по п.1, причем контактирование проводят в условиях реакции, достаточных для образования оксида олефина.
12. Способ по п.11, в котором олефин выбран из С3-12 моноолефина или диолефина, пропилена, бутадиена, циклопентадиена, дициклопентадиена, стирола, α-метилстирола, дивинилбензола, аллилового спирта, простого диаллилового эфира, простого аллилэтилового эфира, аллилбутирата, аллилацетата, аллилбензола, простого аллилфенилового эфира, простого аллилпропилового эфира, аллиланизола и их смесей.
13. Способ по п.11, в котором, когда процесс проводят в газовой фазе, используют разбавитель, выбранный из группы, состоящей из гелия, азота, аргона, метана, диоксида углерода, водяного пара и их смесей; или, когда процесс проводят в жидкой фазе, используют разбавитель, выбранный из С6-15 ароматических углеводородов, хлорированных С1-10 углеводородов, С1-10 алифатических спиртов, хлорированных С1-10 алканолов, простых С2-20 эфиров и жидких простых полиэфиров, многоатомных спиртов и сложных полиэфиров.
14. Способ по п.11, в котором разбавитель используют в газовой фазе в количестве более 0 и менее 90 мол.% в расчете на общее число молей олефина, кислорода, водорода и разбавителя; или в котором используют жидкий разбавитель (или растворитель) в жидкой фазе в количестве более 5 и менее 95 мас.% в расчете на общую массу олефина и разбавителя.
15. Способ по п.11, в котором процесс гидроокисления проводят при температуре более 160°С и менее 300°С и давлении от атмосферного до 500 фунт/кв. дюйм (3448 кПа).
16. Композиция предшественника катализатора, содержащая кластерный комплекс золото-лиганд, осажденный на частицы нанопористого титаносиликатного носителя.
17. Композиция предшественника катализатора по п.16, в которой кластерный комплекс золото-лиганд имеет диаметр (или самый большой размер) более 0,54±0,04 нм.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US85973806P | 2006-11-17 | 2006-11-17 | |
| US60/859,738 | 2006-11-17 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2009122732A true RU2009122732A (ru) | 2010-12-27 |
| RU2445159C2 RU2445159C2 (ru) | 2012-03-20 |
Family
ID=39168720
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2009122732/04A RU2445159C2 (ru) | 2006-11-17 | 2007-11-07 | Способ гидроокисления с использованием катализатора, полученного из кластерного комплекса золота |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US8288311B2 (ru) |
| EP (1) | EP2086674B1 (ru) |
| JP (1) | JP2010510048A (ru) |
| KR (1) | KR20090083906A (ru) |
| CN (2) | CN101534941B (ru) |
| AT (1) | ATE527057T1 (ru) |
| BR (1) | BRPI0716682A2 (ru) |
| ES (1) | ES2372548T3 (ru) |
| MX (1) | MX2009005173A (ru) |
| MY (1) | MY145792A (ru) |
| RU (1) | RU2445159C2 (ru) |
| WO (1) | WO2008063880A1 (ru) |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007137412A1 (en) * | 2006-05-26 | 2007-12-06 | Lakehead University | Nanoporous material |
| JP2010222333A (ja) * | 2009-03-25 | 2010-10-07 | Hokkaido Univ | Ａｕ１３クラスタ及び金クラスタの製造方法 |
| CN102781582B (zh) * | 2009-11-06 | 2017-03-29 | 加利福尼亚大学董事会 | 具有可到达的金属表面的金属胶体 |
| KR101268280B1 (ko) | 2010-12-28 | 2013-05-28 | 연세대학교 산학협력단 | 광촉매 활성을 갖는 금 클러스터 이산화티타늄 나노 복합체, 그 제조방법 및 이를 이용한 유기염료 분해방법 |
| US8617502B2 (en) | 2011-02-07 | 2013-12-31 | Cristal Usa Inc. | Ce containing, V-free mobile denox catalyst |
| JP5794294B2 (ja) * | 2011-03-04 | 2015-10-14 | トヨタ自動車株式会社 | 金属粒子及びそれを含む排ガス浄化用触媒並びにそれらの製造方法 |
| ES2396896B1 (es) * | 2011-05-19 | 2014-01-16 | Sumitomo Chemical Company, Limited | Proceso para producir óxido de olefina. |
| CN105148999B (zh) * | 2011-06-10 | 2017-09-05 | 因温斯特技术公司 | 镍金属配体催化剂形成上的改进 |
| GB201111819D0 (en) | 2011-07-11 | 2011-08-24 | Johnson Matthey Plc | Catalyst and method for its preparation |
| WO2013027677A1 (ja) | 2011-08-23 | 2013-02-28 | トヨタ自動車株式会社 | 排ガス用浄化触媒およびその製造方法 |
| WO2013096039A1 (en) | 2011-12-22 | 2013-06-27 | 3M Innovative Properties Company | Ethylene removal agent |
| JP5943280B2 (ja) * | 2012-06-12 | 2016-07-05 | 公立大学法人首都大学東京 | 金クラスター触媒及びその製造方法 |
| US20140081040A1 (en) * | 2012-09-20 | 2014-03-20 | Lyondell Chemical Technology, L.P. | Process for pre-treatment of a catalyst support and catalyst prepared therefrom |
| WO2014083772A1 (ja) * | 2012-11-30 | 2014-06-05 | 国立大学法人広島大学 | 金属ナノ粒子複合体の製造方法およびその方法により製造された金属ナノ粒子複合体 |
| CN102962029A (zh) * | 2012-12-11 | 2013-03-13 | 常州大学 | 一种造纸废水的处理剂 |
| RU2016143167A (ru) * | 2014-04-22 | 2018-05-23 | Сабик Глобал Текнолоджис Б.В. | Способ синтеза наночастиц золота (au) на носителе для реакций эпоксидирования |
| NL2013836B1 (en) | 2014-11-20 | 2016-10-10 | Univ Delft Tech | Production of nanostructured materials. |
| JP6461663B2 (ja) * | 2015-03-20 | 2019-01-30 | 高知県公立大学法人 | 酸化チタン触媒およびその製造方法 |
| WO2017040121A1 (en) * | 2015-08-28 | 2017-03-09 | Lyondell Chemical Technology, L.P. | Epoxidation processes and catalysts for use therein |
| US9849445B2 (en) * | 2015-09-28 | 2017-12-26 | Uchicago Argonne, Llc | Subnanometer to nanometer transition metal CO oxidation catalysts |
| US10647621B2 (en) * | 2015-11-30 | 2020-05-12 | Adelaide Research and Innovation, The University of Adelaide | Photocatalytic conversion of carbon dioxide and water into substituted or unsubstituted hydrocarbon(s) |
| CN105344383B (zh) * | 2015-12-11 | 2018-07-20 | 中国科学院上海高等研究院 | 一种载体TiO2及其制备方法与应用 |
| CN107405612B (zh) * | 2015-12-28 | 2020-09-15 | 丰田自动车株式会社 | 簇载持催化剂及其制造方法 |
| CN106040303B (zh) * | 2016-06-30 | 2018-07-20 | 苏州大学张家港工业技术研究院 | β–二亚胺基二价稀土硼氢配合物在催化酮与硼烷硼氢化反应中的应用 |
| CN106040304B (zh) * | 2016-06-30 | 2018-06-26 | 苏州大学 | β–二亚胺基二价稀土硼氢配合物在催化醛与硼烷硼氢化反应中的应用 |
| WO2019004318A1 (ja) * | 2017-06-27 | 2019-01-03 | トヨタ自動車株式会社 | クラスター担持多孔質担体及びその製造方法 |
| US10753247B2 (en) * | 2018-02-22 | 2020-08-25 | GM Global Technology Operations LLC | Bi-metallic oxidation catalyst materials and appurtenant devices and systems |
| KR102134767B1 (ko) * | 2018-06-01 | 2020-08-26 | 한국과학기술연구원 | Au-Pt 합금을 포함하는 촉매, 이의 제조방법 및 이를 이용한 과산화수소 합성 방법 |
| CN109399659A (zh) * | 2018-11-16 | 2019-03-01 | 华东理工大学 | 一种小尺寸金纳米颗粒负载的钛硅沸石及其制备方法 |
| CN109647506A (zh) * | 2019-02-03 | 2019-04-19 | 华东理工大学 | 一种负载型金催化剂制备方法和用途 |
| CN110465327B (zh) * | 2019-08-24 | 2022-07-15 | 中海油天津化工研究设计院有限公司 | 一种高活性重芳烃轻质化催化剂及其制备方法 |
| WO2021066411A1 (ko) * | 2019-09-30 | 2021-04-08 | 주식회사 엘지화학 | 프로필렌의 암모산화용 촉매, 이의 제조 방법, 및 이를 이용한 프로필렌의 암모산화 방법 |
| WO2021066409A1 (ko) * | 2019-09-30 | 2021-04-08 | 주식회사 엘지화학 | 프로필렌의 암모산화용 촉매, 이의 제조 방법, 이를 이용한 프로필렌의 암모산화 방법 |
| CN112973681B (zh) * | 2019-12-16 | 2022-11-08 | 中国科学院大连化学物理研究所 | 一种金属纳米团簇催化剂在醇一步法制备缩醛中的应用 |
| CN111393271B (zh) * | 2020-05-06 | 2023-05-02 | 复旦大学 | 一种用于催化烃类化合物与氧气反应的协同催化氧化方法 |
| CN113912569B (zh) * | 2020-07-10 | 2024-04-26 | 中国石油化工股份有限公司 | 可降低稀释气用量的丙烯直接环氧化的方法 |
| CN111939974A (zh) * | 2020-08-20 | 2020-11-17 | 江苏博霖环保科技有限公司 | 一种净化室内甲醛的钛硅分子筛复合材料的制备方法 |
| CN114618568B (zh) * | 2020-12-09 | 2023-08-15 | 中国石油化工股份有限公司 | Ti-β分子筛在制甲烷氧化偶联反应催化剂中的应用以及镱系催化剂及其制备方法和应用 |
| CN114471700A (zh) * | 2022-02-28 | 2022-05-13 | 华东理工大学 | 用于丙烯氢氧环氧化的物理混合式催化剂及制备方法和应用 |
| CN115155653A (zh) * | 2022-08-12 | 2022-10-11 | 华东理工大学 | 一种硫助剂修饰的钛硅分子筛固载金催化剂及其制备方法与应用 |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4425672A1 (de) * | 1994-07-20 | 1996-01-25 | Basf Ag | Oxidationskatalysator, Verfahren zu seiner Herstellung und Oxidationsverfahren unter Verwendung des Oxidationskatalysators |
| JP2615432B2 (ja) | 1994-10-28 | 1997-05-28 | 工業技術院長 | 金−酸化チタン含有触媒による炭化水素の部分酸化方法 |
| DE19600708A1 (de) | 1996-01-11 | 1997-07-17 | Basf Ag | Oxidationskatalysator mit einem Gehalt an Lanthanoidmetallen, Verfahren zu seiner Herstellung und Oxidationsverfahren unter Verwendung des Oxidationskatalysators |
| DE19609301C2 (de) * | 1996-03-09 | 1998-12-10 | Veba Oel Ag | Clusterbeladene Träger |
| DE19623609A1 (de) * | 1996-06-13 | 1997-12-18 | Basf Ag | Oxidationskatalysator und Verfahren zur Herstellung von Epoxiden aus Olefinen, Wasserstoff und Sauerstoff unter Verwendung des Oxidationskatalysators |
| KR100449422B1 (ko) | 1996-07-01 | 2005-02-23 | 다우 글로벌 테크놀로지스 인크. | 티타노실리케이트상의금을포함하는촉매조성물및이를사용하는올레핀옥사이드의제조방법 |
| US6323351B1 (en) * | 1997-06-30 | 2001-11-27 | The Dow Chemical Company | Process for the direct oxidation of olefins to olefin oxides |
| US6562986B2 (en) * | 1997-06-30 | 2003-05-13 | Dow Global Technologies, Inc. | Process for the direct oxidation of olefins to olefin oxides |
| JP4016121B2 (ja) * | 1997-09-05 | 2007-12-05 | 独立行政法人産業技術総合研究所 | 炭化水素部分酸化用触媒及び含酸素有機化合物の製造方法 |
| DE69911195T2 (de) * | 1998-04-15 | 2004-07-15 | Dow Global Technologies, Inc., Midland | Verfahren zur direktoxidation von olefinen zu olefinoxiden |
| BR9917025B1 (pt) * | 1998-12-16 | 2010-10-19 | processo para preparar um óxido de olefina, composição de catalisador e processo para regenerá-la. | |
| US6821923B1 (en) * | 1999-04-08 | 2004-11-23 | Dow Global Technologies Inc. | Method of preparing a catalyst containing gold and titanium |
| AU4335100A (en) * | 1999-04-08 | 2000-10-23 | Dow Chemical Company, The | Process for the hydro-oxidation of olefins to olefin oxides using oxidized gold catalyst |
| JP2001026422A (ja) * | 1999-05-10 | 2001-01-30 | Nippon Shokubai Co Ltd | 金含有複合体の製造方法 |
| CN1160149C (zh) * | 2000-02-22 | 2004-08-04 | 阿科化学技术公司 | 采用改进的催化剂组合物的直接环氧化方法 |
| BR0211796A (pt) * | 2001-08-01 | 2004-08-03 | Dow Global Technologies Inc | Método para aumentar a vida útil de um catalisador de hidro-oxidação |
| AU2003209327A1 (en) | 2002-01-23 | 2003-09-02 | Huntsman International Llc | Gas-phase process and catalyst for the preparation of propylene oxide |
| US7081433B2 (en) * | 2003-03-12 | 2006-07-25 | The United States Of America As Represented By The Secretary Of The Navy | Catalytic three dimensional aerogels having mesoporous nanoarchitecture |
| PL1977816T3 (pl) | 2003-09-26 | 2012-01-31 | 3M Innovative Properties Co | Katalizatory, środki aktywujące, środki nośne i związane z nimi metody przydatne przy tworzeniu takich układów katalitycznych zwłaszcza, gdy katalizator jest osadzany na środkach nośnych poprzez fizyczne osadzanie z fazy gazowej |
| EP1776187A1 (en) | 2004-07-06 | 2007-04-25 | University College Cardiff Consultants, Ltd. | Supported gold catalysts |
| US7432384B2 (en) * | 2005-10-25 | 2008-10-07 | Lyondell Chemical Technology, L.P. | Direct epoxidation process |
-
2007
- 2007-11-07 EP EP07844932A patent/EP2086674B1/en not_active Not-in-force
- 2007-11-07 MX MX2009005173A patent/MX2009005173A/es active IP Right Grant
- 2007-11-07 KR KR1020097010091A patent/KR20090083906A/ko not_active Application Discontinuation
- 2007-11-07 JP JP2009537275A patent/JP2010510048A/ja active Pending
- 2007-11-07 BR BRPI0716682-6A2A patent/BRPI0716682A2/pt not_active IP Right Cessation
- 2007-11-07 CN CN200780042532XA patent/CN101534941B/zh not_active Expired - Fee Related
- 2007-11-07 ES ES07844932T patent/ES2372548T3/es active Active
- 2007-11-07 US US12/445,547 patent/US8288311B2/en not_active Expired - Fee Related
- 2007-11-07 WO PCT/US2007/083859 patent/WO2008063880A1/en active Application Filing
- 2007-11-07 AT AT07844932T patent/ATE527057T1/de not_active IP Right Cessation
- 2007-11-07 RU RU2009122732/04A patent/RU2445159C2/ru not_active IP Right Cessation
- 2007-11-07 CN CN2011101880310A patent/CN102309987A/zh active Pending
- 2007-11-07 MY MYPI20092020A patent/MY145792A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MX2009005173A (es) | 2009-05-25 |
| CN101534941B (zh) | 2012-07-18 |
| KR20090083906A (ko) | 2009-08-04 |
| BRPI0716682A2 (pt) | 2013-09-24 |
| CN102309987A (zh) | 2012-01-11 |
| ES2372548T3 (es) | 2012-01-23 |
| RU2445159C2 (ru) | 2012-03-20 |
| JP2010510048A (ja) | 2010-04-02 |
| CN101534941A (zh) | 2009-09-16 |
| WO2008063880A1 (en) | 2008-05-29 |
| MY145792A (en) | 2012-04-30 |
| US8288311B2 (en) | 2012-10-16 |
| ATE527057T1 (de) | 2011-10-15 |
| US20100076208A1 (en) | 2010-03-25 |
| EP2086674A1 (en) | 2009-08-12 |
| EP2086674B1 (en) | 2011-10-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2009122732A (ru) | Способ гидроокисления с использованием катализатора, полученного из кластерного комплекса золота | |
| Guthertz et al. | Half-sandwich ruthenium carbene complexes link trans-hydrogenation and gem-hydrogenation of internal alkynes | |
| Guzman et al. | Simultaneous presence of cationic and reduced gold in functioning MgO-supported CO oxidation catalysts: Evidence from X-ray absorption spectroscopy | |
| Fürstner | From understanding to prediction: Gold-and platinum-based π-acid catalysis for target oriented synthesis | |
| JP2010510048A5 (ru) | ||
| Bianchini et al. | The mechanism of the Ru-assisted C− C bond cleavage of terminal alkynes by water | |
| Barton et al. | Kinetic study of a direct water synthesis over silica-supported gold nanoparticles | |
| Gomez-Suarez et al. | Influence of a very bulky N-heterocyclic carbene in gold-mediated catalysis | |
| Blackburn et al. | Reactive deposition of conformal palladium films from supercritical carbon dioxide solution | |
| Thompson | New advances in gold catalysis part II | |
| Terry et al. | Covalent heterogenization of a discrete Mn (II) bis-phen complex by a metal-template/metal-exchange method: An epoxidation catalyst with enhanced reactivity | |
| Vargas et al. | Adsorption of activated ketones on platinum and their reactivity to hydrogenation: a DFT study | |
| Shvo et al. | New ruthenium complexes in the catalytic hydrogenation of alkynes. Study of structure and mechanism | |
| Hierso et al. | Platinum, palladium and rhodium complexes as volatile precursors for depositing materials | |
| Dai et al. | Water-enhanced selective hydrogenation of cinnamaldehyde to cinnamyl alcohol on RuSnB/CeO2 catalysts | |
| Xu et al. | Introducing frustrated Lewis pairs to metal–organic framework for selective hydrogenation of N-heterocycles | |
| Flückiger et al. | Iron (II)‐Catalyzed Asymmetric Hydrosilylation of Acetophenone | |
| CN109928864A (zh) | 一种多功能复合催化剂及其在合成气直接制乙醇的应用 | |
| CN1376151A (zh) | 催化剂的制备及环氧化方法 | |
| Ohki et al. | [{(η5‐C5Me5) Fe} 2 (μ‐H) 4]: A Novel Dinuclear Iron Tetrahydrido Complex | |
| Fan et al. | Air-Stable Half-Sandwich Iridium Complexes as Aerobic Oxidation Catalysts for Imine Synthesis | |
| Luo et al. | Controlled selectivity through reversible inhibition of the catalyst: stereodivergent semihydrogenation of alkynes | |
| TW593130B (en) | Direct synthesis of hydrogen peroxide in a new multicomponent solvent system | |
| JP2012504596A (ja) | ホスフィノオキシドベースのルテニウム錯体を有するエステル基又はカルボニル基の水素化 | |
| Haukka et al. | Catalytic activity of ruthenium 2, 2′-bipyridine derived catalysts in 1-hexene hydroformylation and 1-heptanal hydrogenation |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20131108 |