CN109395714A - A kind of catalyst and preparation method thereof prepared using jasmine flower extract - Google Patents
A kind of catalyst and preparation method thereof prepared using jasmine flower extract Download PDFInfo
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- CN109395714A CN109395714A CN201710704244.1A CN201710704244A CN109395714A CN 109395714 A CN109395714 A CN 109395714A CN 201710704244 A CN201710704244 A CN 201710704244A CN 109395714 A CN109395714 A CN 109395714A
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- 239000003054 catalyst Substances 0.000 title claims abstract description 52
- 235000010254 Jasminum officinale Nutrition 0.000 title claims abstract description 32
- 238000002360 preparation method Methods 0.000 title claims abstract description 25
- 239000000284 extract Substances 0.000 title claims abstract description 22
- 240000005385 Jasminum sambac Species 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 35
- 241000207840 Jasminum Species 0.000 claims abstract description 31
- 239000011943 nanocatalyst Substances 0.000 claims abstract description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 91
- 239000002105 nanoparticle Substances 0.000 claims description 18
- 239000003381 stabilizer Substances 0.000 claims description 14
- 239000003638 chemical reducing agent Substances 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 5
- 239000002245 particle Substances 0.000 claims description 5
- 239000002243 precursor Substances 0.000 claims description 4
- 239000004094 surface-active agent Substances 0.000 claims description 3
- JKDRQYIYVJVOPF-FDGPNNRMSA-L palladium(ii) acetylacetonate Chemical compound [Pd+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O JKDRQYIYVJVOPF-FDGPNNRMSA-L 0.000 claims description 2
- 238000011946 reduction process Methods 0.000 claims description 2
- 239000013078 crystal Substances 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 239000012696 Pd precursors Substances 0.000 abstract description 2
- 229910052763 palladium Inorganic materials 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000000126 substance Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000000341 volatile oil Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000725 suspension Substances 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 7
- 150000002940 palladium Chemical class 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- 230000009467 reduction Effects 0.000 description 6
- 238000003860 storage Methods 0.000 description 6
- 238000000605 extraction Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- -1 Technique of Nano Pd Chemical compound 0.000 description 4
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000011668 ascorbic acid Substances 0.000 description 3
- 235000010323 ascorbic acid Nutrition 0.000 description 3
- 229960005070 ascorbic acid Drugs 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 239000003205 fragrance Substances 0.000 description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 238000012805 post-processing Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- GDSOZVZXVXTJMI-SNAWJCMRSA-N (e)-1-methylbut-1-ene-1,2,4-tricarboxylic acid Chemical compound OC(=O)C(/C)=C(C(O)=O)\CCC(O)=O GDSOZVZXVXTJMI-SNAWJCMRSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229920002079 Ellagic acid Polymers 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 238000010668 complexation reaction Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000005672 electromagnetic field Effects 0.000 description 2
- 235000004132 ellagic acid Nutrition 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-O guanidinium Chemical compound NC(N)=[NH2+] ZRALSGWEFCBTJO-UHFFFAOYSA-O 0.000 description 2
- 239000002608 ionic liquid Substances 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 2
- 239000004530 micro-emulsion Substances 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000002893 slag Substances 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- AFSDNFLWKVMVRB-UHFFFAOYSA-N Ellagic acid Chemical compound OC1=C(O)C(OC2=O)=C3C4=C2C=C(O)C(O)=C4OC(=O)C3=C1 AFSDNFLWKVMVRB-UHFFFAOYSA-N 0.000 description 1
- ATJXMQHAMYVHRX-CPCISQLKSA-N Ellagic acid Natural products OC1=C(O)[C@H]2OC(=O)c3cc(O)c(O)c4OC(=O)C(=C1)[C@H]2c34 ATJXMQHAMYVHRX-CPCISQLKSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- LOMVENUNSWAXEN-UHFFFAOYSA-N Methyl oxalate Chemical compound COC(=O)C(=O)OC LOMVENUNSWAXEN-UHFFFAOYSA-N 0.000 description 1
- 241000207834 Oleaceae Species 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 229960002852 ellagic acid Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 235000004515 gallic acid Nutrition 0.000 description 1
- 229940074391 gallic acid Drugs 0.000 description 1
- 239000011964 heteropoly acid Substances 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- FAARLWTXUUQFSN-UHFFFAOYSA-N methylellagic acid Natural products O1C(=O)C2=CC(O)=C(O)C3=C2C2=C1C(OC)=C(O)C=C2C(=O)O3 FAARLWTXUUQFSN-UHFFFAOYSA-N 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000002811 oleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000005691 oxidative coupling reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- GPNDARIEYHPYAY-UHFFFAOYSA-N palladium(ii) nitrate Chemical compound [Pd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O GPNDARIEYHPYAY-UHFFFAOYSA-N 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052594 sapphire Inorganic materials 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- SDKPSXWGRWWLKR-UHFFFAOYSA-M sodium;9,10-dioxoanthracene-1-sulfonate Chemical compound [Na+].O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)[O-] SDKPSXWGRWWLKR-UHFFFAOYSA-M 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000002604 ultrasonography Methods 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
- B01J23/38—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
- B01J23/42—Platinum
-
- 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
- B01J35/30—Catalysts, in general, characterised by their form or physical properties characterised by their physical properties
- B01J35/391—Physical properties of the active metal ingredient
- B01J35/393—Metal or metal oxide crystallite size
-
- 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
- B01J35/30—Catalysts, in general, characterised by their form or physical properties characterised by their physical properties
- B01J35/391—Physical properties of the active metal ingredient
- B01J35/394—Metal dispersion value, e.g. percentage or fraction
-
- 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
- B01J37/16—Reducing
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
- C07C51/44—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/62—Three oxygen atoms, e.g. ascorbic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/06—Peri-condensed systems
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- Chemical & Material Sciences (AREA)
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- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Crystallography & Structural Chemistry (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The catalyst and preparation method thereof that the present invention provides a kind of to be prepared using jasmine flower extract, the catalyst are Pd nanocatalyst, are in particularly good crystal habit.The preparation method restores Pd precursor using jasmine flower extract.The method is especially environmental-friendly, and production cost is low, overall economic efficiency with higher.
Description
Technical field
The invention belongs to catalyst technical fields, and in particular to it is a kind of using jasmine flower extract prepare catalyst and its
Preparation method.
Background technique
It is well known in the art that palladium catalyst although active high, the good performance of selectivity, has in many fields
It is widely used, especially has a wide range of applications in chemical industry and petroleum and organic synthesis field.
The various Preparation Methods of palladium catalyst have obtained extensive research.However, palladium catalyst made from different methods due to
All there are great differences for catalyst granules pattern, purity and dopant type etc., and leading to its catalytic performance, there is also very big differences, no
With the economy and the feature of environmental protection of preparation method, there is also very big differences.
The known synthesis there are many method for palladium, particularly Technique of Nano Pd, the common method of one type include that chemistry is gone back
It is former.However, needing to use reducing agent, especially strong reductant in existing restoring method.In large-scale industrial production
In, for example toxic hydrazine compound of these reducing agents is possible to cause serious adverse effect to operator or environment.This routine
Method be not obviously inconsistent with current green chemical concept.
CN103301852A discloses a kind of preparation method of palladium carbon catalyst, and the method comprising the steps of are as follows: adds in palladium
Add metallic element and carry out hybrid reaction and palldium alloy is made；The palldium alloy is impregnated and restored in adsorption liquid, is done after taking-up
The dry palladium carbon catalyst for obtaining high dispersive type.
CN105126831A discloses a kind of preparation method of nanoscale palladium catalyst, and this method is with room-temperature ion liquid
It is medium that body and water, which are formed by microemulsion system, makes itself and Microemulsion fabricated in situ palladium in such a way that palladium chloride is added dropwise
Nano particle, so that preparation forms a kind of nanoscale palladium catalyst.
CN103357401A discloses a kind of preparation method of palladium-based catalyst, comprising the following steps: A) by carrier, palladium source
It is mixed in the solution with Keggin-type heteropoly acid, obtains suspension；B the pH value of the suspension) is adjusted with alkaline solution, then plus
Enter reducing agent to be reacted, obtains catalyst；C the catalyst is calcined in oxygen atmosphere), obtains palladium-based catalyst.
CN104971738A discloses the preparation method of magnetic Nano palladium catalyst, water-soluble with tetramethylammonium hydroxide first
Secondly the nano oxidized iron particle of liquid processing forms nano oxidized iron particle and metal palladium salt in alcohol and n,N-Dimethylformamide
In the mixed solvent ultrasound, magnetic Nano palladium catalyst is sucked out with magnet from the mixed solvent finally and uses deionized water respectively
It is stored in methanol with after methanol washing.
CN103657643A discloses a kind of method for preparing nano palladium metal catalyst, this method comprises: by carrier with
Function additive carries out graft reaction in organic solvent, adds the organic solution of palladium salt or palladium salt, makes palladium salt and function additive
Occur also to be captured by carrier while complexation reaction, reuses reducing agent for palladium salt and be reduced into metal palladium nano-particles, then
Embedding medium is added, is separated coating reaction, finally obtains the nano palladium metal catalyst of stable solid-carrying type.
CN103007928A discloses a kind of preparation method of palladium nanoparticle catalyst, this method comprises: in a solvent,
At 0 DEG C~100 DEG C, palladium acetate and boric acid compound are acted on, and react -1 hour 1 minute, and palladium nano-particles are made.
CN102423704A discloses a kind of preparation method of palladium nano catalyst used for direct methanoic acid fuel cell, including with
Lower step: high-area carbon is dispersed in water, suspension is obtained；Guanidinium ionic liquid and palladium metal forerunner is added to the suspension
The guanidinium ionic liquid and palladium metal presoma complexation reaction and are formed containing palladium complex by body occurs；It described will be complexed containing palladium
Object reacts to form Pd nano particle and be deposited on the high-area carbon surface with reducing agent, and direct formic acid combustion is obtained after washing, drying
Expect battery palladium nanocatalyst.
WO2007/094903A1 discloses the preparation method of the palladium-gold catalyst of load, and the method includes (a) to make two
Titanium dioxide carrier sulphation；(b) carrier of the sulphation is calcined；It (c) should with palladium salt, gold salt and alkali metal or ammonium compounds dipping
Calcined support；(d) carrier through impregnating is calcined；(e) calcined support of step (d) is restored and is formed and is loaded
Palladium-gold catalyst.
" liquid phase local reduction way prepares palladium-based catalyst ", rain etc., Industrial Catalysis, discloses use at 04 phase in 2015
Liquid phase local reduction way prepares Pd/ α-Al2O3Catalyst, and be applied to CO oxidative coupling synthesizing dimethyl oxalate and react, comparison is real
It issues after examination and approval now, Pd base catalyst made from formaldehyde liquid phase local reduction way has excellent catalytic activity, when Pd load quality score
When down to 0.1%, catalyst still shows higher activity and stability.
Jasmine has been selected in order to seek a kind of palladium catalyst for meeting green chemical concept and its synthetic method, the present invention
Extract carries out the synthesis of palladium catalyst as reducing agent and stabilizer.Jasmine is Oleaceae plants, is evergreen shrubs, is one
Kind fine perfumery plant.Leaf, flower, the root of Jasmine have medical value.Jasmine also has strong fragrance, even more many flowers
Not available for piece, the principle active component of jasmine essential oil is volatile oil, is a kind of fragrance for especially having economic value.How
Its extraction of essential oil by-product is used especially meaningful.
As it was noted above, above-mentioned document and it is other in the prior art, urged in existing palladium catalyst, especially Technique of Nano Pd
In the preparation of agent, the solvent that uses is simultaneously not environmentally and economical.This field needs a kind of economic, environmental protection and effective palladium catalyst
Preparation method and catalyst obtained.
Summary of the invention
In order to solve the above problems simultaneously, the present inventor extracts jasmine essential oil by further investigation and many experiments
In byproduct compounds analysed in depth, attempt to be used for the preparation of palladium catalyst.Meeting environmental protection concept and requirement
Meanwhile improving the overall economic efficiency of the technique.
The present inventor it has been investigated that, jasmine essential oil extracts in by-product the Gallic Acid that contains and anti-
Bad hematic acid or their analog, such as ellagic acid, the compound due to its hydroxyl structure presence and can be converted to fair
Perhaps electric charge transfer and the therefore form as reducing agent.Many such as ellagic acids can also play surfactant in the substance
Effect.These substances can thus play the role of stabilizer and reducing agent simultaneously.
On this basis, it based on the discovery that, in one aspect of the invention, provides a kind of using jasmine flower extract
The catalyst of (i.e. as reducing agent and stabilizer) preparation, the catalyst are Pd nanocatalyst.
Preferably, the crystallite dimension of the Pd nano-catalyst particles is 2nm-50nm, preferably 5nm.
Preferably, described Pd nanometers is in monodisperse status.
Preferably, the Pd nano particle is in polycrystalline structure.
Preferably, the standard deviation of the partial size of the Pd nano particle of the catalyst is less than 5%, and preferably smaller than 3%.Existing
Rarely seen so even-grained Pd nano particle in some Pd catalyst.
Preferably, the precursor of the Pd is Pd (acac)2.The study found that compared with palladium nitrate, Pd (acac)2It can provide
Pd nano particle pattern after optimal reduction, such as with the smallest particle diameter standard deviation.
In another aspect of this invention, a kind of method for preparing above-mentioned catalyst is provided, this method includes using jasmine
Flower extract prepares Pd nano particle as stabilizer and reducing agent, by the precursor of Pd.
Preferably, co-conducer is added in reduction process.It is highly preferred that the co-conducer is borine-tri-n-butylamine network
Close object.The addition of the co-conducer can shorten the recovery time.
In an especially preferred embodiment, surfactant is not added additionally in the preparation process of catalyst
And/or stabilizer.
Specifically, the preparation method includes: the Pd (acac) for taking 0.01-0.1mol/mL2(Sigma Aldrich), will
It is heated to 40-60 DEG C, and the jasmine flower extract for effectively going back commercial weight is then added thereto while agitating, uses 0.01-
The sodium hydroxide solution of 0.08M adjusts pH to 6.0-11.0, reacts 30-60min, obtains Pd nano granule suspension, then into
Row centrifuge separation, washing and drying are to get Pd nano particle.
The study found that the jasmine flower extract plays the role of reducing agent and stabilizer simultaneously.In pervious document
In do not find such report.
Preferably, co-conducer can be added in the specific method.The co-conducer is preferably borine-tri-n-butylamine complexing
Object.Borine-tri-n-butylamine complex compound mole is Pd (acac)21/10-1/5.
More specifically, the preparation method includes: the Pd (ac ac) for taking the 0.025mol/mL of 100mL2, it is heated to
50 DEG C, jasmine flower extract 2.0g is then added thereto while agitating, adjusts pH using the sodium hydroxide solution of 0.05M
To 9.0,60min is reacted, Pd nano granule suspension is obtained, is then centrifuged, washs and dries to get Pd nanometers
Grain.
The present inventor it has been investigated that, enough a effective amount of 3 how are kept in jasmine flower extract, 4,5- trihydroxies
Benzoic acid and ascorbic acid or their analog are extremely important, this is also the key point of the method for the present invention.General jasmine
In flower essential oil extracting method, extraction step and parameter are solely focused on the acquisition of jasmine essential oil fragrance, and the substance by
It is destroyed to serious.For this purpose, the present invention provides the acquisition jasmine flower extracts such as lower section on the basis of previous research
Method is put into micro-wave oven and is dried to weightlessness 60~80%, so method includes the following steps: (1) picks new fresh jasmine flower
After be stored in refrigerator, storage temperature be -5 DEG C~-10 DEG C；(2) flower is shredded, according to colored and water 1: 3~1: 5 ratio
Example mixing, is then distilled, the timing since condenser is collected into condensate liquid outflow, every the flower slag of taking-up in 1~2 hour, together
When be reentered into fresh flower, after continuous still 5-10 times, collect distillate；(3) sodium bicarbonate is added (preferably into distillate
0.01-0.1mol/L), pH value is adjusted to 9.0-12.0, and the petroleum ether for being then incorporated as the 1/3-1/5 of distillate volume is extracted
It takes, repeats aforesaid operations 2-5 times, merge water phase and organic phase (i.e. petroleum ether phase)；(4) dilute hydrochloric acid is added in Xiang Suoshu water phase
(preferably 0.01-0.1mol/L) adjusts pH to 3.0-6.0, is then extracted with chloroform, collect organic phase, is being lower than 60
It is concentrated under reduced pressure at a temperature of DEG C, concentrate is lyophilized to get jasmine flower extract.
The petroleum ether mutually can be used for the preparation of Jasmine volatile oil.
In the method, it is preferable that new storage time of the fresh jasmine after weightlessness in refrigerator be less than 30 days, it is excellent
Choosing was less than 10 days.
The present inventor is the study found that in room temperature storing process, many kinds of substance in flower, especially temperature-sensitivmaterial material
(being all much the active principle in the preparation of Pd nanocatalyst), in the case where flower is rich in moisture, is easy to happen structure
Variation or degradation.Therefore, present invention selection is dried using micro-wave oven to weightless 60~80%, preferably 75%.Microwave heating
It is different from traditional heating method, it is not required to heat transfer process, it can make heating object material itself become calandria, therefore even if
It is the poor material of heat conductivity, heating temperature can also be reached in a very short period of time.For flower heating, hydrone
It is polarized in microwave electromagnetic field, there are dipole characteristics, and as the frequency of electromagnetic field is constantly changing polar orientation, molecule
Make vibration at high speed, generate frictional heat, so that flower is heated up from inner deep, and temperature is consistent everywhere, this of microwave heating is special
Performance enough makes flower be rapidly heated, and reaches the critical point temperature of wherein inactive enzyme, accelerates the migration of flower constitution water, to make temperature
It is minimum to spend sensitive materials loss.Flower after quick dehydration carries out low-temperature storage again, can store for a long time and temperature is sensitive
Substance (including essential oil and ascorbic acid) hardly occur reduce or deteriorate, storage period may be up to 1 year even it is longer.If no
Carry out the quick dehydration of microwave and directly carry out low-temperature storage, then can be lost after 1 year about 30% or more can be used for palladium salt reduction
Active principle such as ascorbic acid.
For the present invention, in step (2), the water is the water containing NaCl.Preferably, the concentration of NaCl is 0.1-
1.0 weight %.
It is further preferred that the extraction stabilizer (or distillation stabilizer) in the water also containing 0.1-0.5 weight %.It steams
The temperature for evaporating extraction may lead the decomposition of temperature-sensitivmaterial material (being much reducing substances).Based on described problem, adopt at present
The measure taken is directed to improve distillation equipment, for example, by using the steaming of pressurization string, continuous still, multiple fractional distillation column distillation and worm-gear type
The forms such as quick steam distillation.These modes spend larger, need biggish investment.For this purpose, the present invention is in distillation process
It joined stabilizer, the thermal decomposition of temperature-sensitivmaterial material can be reduced to a certain extent.The stabilizer is preferably oleoyl two
Amine stabiliser.It is highly preferred that the extraction stabilizer is oleoyl diamine compound shown in lower formula (I):
Experiment shows when the compound is added, and should can effectively improve in distillation process and easily be oxidized substance as resisted
The stability of bad hematic acid, such as even if distillation Extracting temperature improves 20 DEG C, the stability for being easily oxidized substance is also kept not substantially
Become.
Preferably, the Pd catalyst nano-particles of the method for the present invention have (100) and (111) crystal face.It is highly preferred that each
Crystal domain in Pd nano particle has the interface distance of 0.228nm, and the spacing of lattice in (111) face is 0.223nm.Such crystalline substance
Body structure makes all have particularly preferred catalytic activity in the application of many catalyst.
Detailed description of the invention
Fig. 1 is the XRD diagram of the according to embodiments of the present invention 2 Pd nano particles obtained；
Fig. 2 is the TEM figure of the according to embodiments of the present invention 2 Pd nano particles in suspension obtained.
Specific embodiment
Below with reference to following embodiment and comparative example, the present invention is described in further detail, but embodiment party of the invention
Formula is without being limited thereto.
Embodiment 1
New fresh jasmine flower is picked, is put into micro-wave oven and dries to weightlessness 70%, be then stored in refrigerator, storage temperature
Degree is -5 DEG C, and flower is shredded, and mixes according to flower with the ratio of water 1: 4, is then distilled, be collected into condensate liquid from condenser
Outflow starts timing, every the flower slag of taking-up in 1.5 hours, while being reentered into fresh flower, after continuous still 6 times, collects distillate, to
0.01mol/L sodium bicarbonate is added in distillate, adjusts pH value to 9.0, is then incorporated as 1/4 petroleum ether of distillate volume
It is extracted, is repeated aforesaid operations 3 times, merged water phase and petroleum ether phase, the dilute salt of 0.01mol/L is added in Xiang Suoshu water phase
Acid, adjust pH to 4.0, then extracted with chloroform, collect organic phase, 50 DEG C at a temperature of be concentrated under reduced pressure, by concentrate
Freeze-drying is to get jasmine flower extract.
Embodiment 2
Take the Pd (acac) of 100mL 0.025mol/mL2(being purchased from Sigma Aldrich), is heated to 50 DEG C, then
Jasmine flower extract 2.0g made from embodiment 1 is added thereto while agitating, uses the sodium hydroxide solution tune of 0.05M
PH to 9.0 is saved, 60min is reacted, obtains Pd nano granule suspension, be then centrifuged, wash and dry and received to get Pd
Rice grain.
Comparative example 1
The difference of the comparative example and embodiment 2, which is only that, replaces with hydrazine hydrate or boric acid for jasmine flower extract.Due to water
The toxicity for closing hydrazine, needs special operation equipment and safeguard procedures, in addition reaction mixture will pass through special post-processing ability
Discharge.Acid reaction product is also required to allow to discharge by special post-processing.
By above-described embodiment and comparative example clearly it can be seen from method of the invention it is especially environmental-friendly, do not need spy
Different equipment and post-processing, reduces synthesis or production cost, in addition while the extract needed for obtaining reduction Pd precursor,
Jasmine volatile oil can also be made simultaneously, to greatly improve comprehensive utilization value.
This written description discloses the present invention, including optimal mode using example, and also enables those skilled in the art
The manufacture and use present invention.It is of the invention can patentable scope be defined by the claims, and may include this field skill
Other examples that art personnel expect.If this other examples have not different from the structural elements of the literal language of claims
Element, or if this other examples include the equivalent structure element with the literal language of claims without substantial differences,
Then this other examples are intended within the scope of claims.In the case where not will cause inconsistent degree, by reference to
It will be incorporated herein in place of all references referred to herein.
Claims (10)
1. a kind of catalyst prepared using jasmine flower extract, which is Pd nanocatalyst.
2. catalyst according to claim 1, wherein the crystallite dimension of the Pd nano-catalyst particles is 2nm-50nm.
3. catalyst according to claim 1 or 2, wherein described Pd nanometers is in monodisperse status.
4. catalyst according to any one of the preceding claims, wherein the Pd nano particle is in polycrystalline structure.
5. catalyst according to any one of the preceding claims, wherein the standard of the partial size of the Pd nano particle of the catalyst
Deviation is less than 5%.
6. catalyst according to any one of the preceding claims, wherein the precursor of Pd is Pd (acac)2。
7. a kind of method for preparing any one of claim 1-6 catalyst, this method include being made using jasmine flower extract
For stabilizer and reducing agent, Pd nano particle is prepared by the precursor of Pd.
8. method according to claim 7, wherein co-conducer is added in reduction process.
9. method according to claim 8, the co-conducer is borine-tri-n-butylamine complex compound.
10. surfactant is not added additionally in the preparation process of catalyst according to the method for any one of claim 7-9
And/or stabilizer.
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| CN105798324A (en) * | 2016-03-21 | 2016-07-27 | 中山大学 | Mimic enzyme based on self-assembly structure as well as preparation method and application thereof |
| CN106391000A (en) * | 2016-10-10 | 2017-02-15 | 中国科学院福建物质结构研究所 | Pd(111)/gamma-Al2O3 catalyst for CO dehydrogenation purification reaction and preparation method thereof |
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| CN105798324A (en) * | 2016-03-21 | 2016-07-27 | 中山大学 | Mimic enzyme based on self-assembly structure as well as preparation method and application thereof |
| CN106391000A (en) * | 2016-10-10 | 2017-02-15 | 中国科学院福建物质结构研究所 | Pd(111)/gamma-Al2O3 catalyst for CO dehydrogenation purification reaction and preparation method thereof |
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