CN116375575A - Palladium acetate and preparation method of compound thereof - Google Patents
Palladium acetate and preparation method of compound thereof Download PDFInfo
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- CN116375575A CN116375575A CN202310184229.4A CN202310184229A CN116375575A CN 116375575 A CN116375575 A CN 116375575A CN 202310184229 A CN202310184229 A CN 202310184229A CN 116375575 A CN116375575 A CN 116375575A
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- palladium
- palladium acetate
- mixed solution
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- colloid mixed
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- 238000002360 preparation method Methods 0.000 title claims abstract description 45
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 title claims abstract description 44
- 150000001875 compounds Chemical class 0.000 title abstract description 21
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 195
- -1 palladium acetate compound Chemical class 0.000 claims abstract description 114
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 96
- 239000000084 colloidal system Substances 0.000 claims abstract description 80
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 78
- 239000011259 mixed solution Substances 0.000 claims abstract description 77
- 229960000583 acetic acid Drugs 0.000 claims abstract description 38
- 239000012362 glacial acetic acid Substances 0.000 claims abstract description 37
- 238000003756 stirring Methods 0.000 claims abstract description 30
- 238000001914 filtration Methods 0.000 claims abstract description 24
- 238000010438 heat treatment Methods 0.000 claims abstract description 24
- 239000002270 dispersing agent Substances 0.000 claims abstract description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims abstract description 20
- 238000001035 drying Methods 0.000 claims abstract description 19
- 230000007935 neutral effect Effects 0.000 claims abstract description 17
- 238000005406 washing Methods 0.000 claims abstract description 17
- 238000002156 mixing Methods 0.000 claims abstract description 16
- UKLJMHXGZUJRTL-UHFFFAOYSA-L calcium;n-cyclohexylsulfamate Chemical compound [Ca+2].[O-]S(=O)(=O)NC1CCCCC1.[O-]S(=O)(=O)NC1CCCCC1 UKLJMHXGZUJRTL-UHFFFAOYSA-L 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 14
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 claims abstract description 13
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 claims abstract description 6
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims abstract description 3
- 239000012670 alkaline solution Substances 0.000 claims abstract description 3
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 claims abstract description 3
- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 claims abstract description 3
- 235000019982 sodium hexametaphosphate Nutrition 0.000 claims abstract description 3
- 229940048086 sodium pyrophosphate Drugs 0.000 claims abstract description 3
- HEBRGEBJCIKEKX-UHFFFAOYSA-M sodium;2-hexadecylbenzenesulfonate Chemical compound [Na+].CCCCCCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O HEBRGEBJCIKEKX-UHFFFAOYSA-M 0.000 claims abstract description 3
- 235000019818 tetrasodium diphosphate Nutrition 0.000 claims abstract description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 28
- 239000000243 solution Substances 0.000 claims description 21
- 239000003513 alkali Substances 0.000 claims description 16
- 150000002940 palladium Chemical class 0.000 claims description 16
- 238000007792 addition Methods 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 238000002390 rotary evaporation Methods 0.000 claims description 7
- 239000003638 chemical reducing agent Substances 0.000 claims description 6
- 239000013638 trimer Substances 0.000 claims description 4
- 229940043202 calcium cyclamate Drugs 0.000 claims 2
- 239000000625 cyclamic acid and its Na and Ca salt Substances 0.000 claims 2
- LFVPBERIVUNMGV-UHFFFAOYSA-N fasudil hydrochloride Chemical compound Cl.C=1C=CC2=CN=CC=C2C=1S(=O)(=O)N1CCCNCC1 LFVPBERIVUNMGV-UHFFFAOYSA-N 0.000 claims 2
- 238000003889 chemical engineering Methods 0.000 abstract description 2
- 239000012847 fine chemical Substances 0.000 abstract description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 37
- 239000000706 filtrate Substances 0.000 description 32
- DPZNOMCNRMUKPS-UHFFFAOYSA-N 1,3-Dimethoxybenzene Chemical compound COC1=CC=CC(OC)=C1 DPZNOMCNRMUKPS-UHFFFAOYSA-N 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 239000008367 deionised water Substances 0.000 description 16
- 229910021641 deionized water Inorganic materials 0.000 description 16
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 13
- 239000001632 sodium acetate Substances 0.000 description 13
- 235000017281 sodium acetate Nutrition 0.000 description 13
- 239000012065 filter cake Substances 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 7
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 6
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Substances ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 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 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 238000012512 characterization method Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229910001379 sodium hypophosphite Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical group [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 150000002941 palladium compounds Chemical class 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 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
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 238000007341 Heck reaction Methods 0.000 description 1
- 239000004280 Sodium formate Substances 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 238000005899 aromatization reaction Methods 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 238000005810 carbonylation reaction Methods 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000006880 cross-coupling reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
- 235000019254 sodium formate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
-
- 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
- Y02P20/584—Recycling of catalysts
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a preparation method of palladium acetate and a compound thereof, and relates to the technical field of fine chemical engineering; the preparation method comprises the following steps: -preparation of palladium colloid mixed liquor; preparation of palladium acetate: uniformly mixing the palladium colloid mixed solution with glacial acetic acid and acetate, heating to react, dropwise adding an alkaline solution to adjust the pH of the system to be neutral, continuously stirring for 20-40 min, filtering, washing and drying to obtain a palladium acetate compound; adding calcium cyclohexylsulfamate and a dispersing agent in the preparation of the palladium colloid mixed solution; the dispersant is at least one selected from sodium hexametaphosphate, sodium pyrophosphate, sodium dodecyl benzene sulfonate, sodium hexadecyl benzene sulfonate and sodium dodecyl sulfate. The method of the invention can improve the yield of palladium acetate and compounds thereof and simultaneously reduce the loss of palladium.
Description
Technical Field
The invention relates to the technical field of fine chemical engineering, in particular to a preparation method of palladium acetate and a compound thereof.
Background
Palladium acetate (Palladium acetate), also known as palladium acetate, is a yellow-brown or reddish-brown uniform powder in appearance, is stable in air, is soluble in toluene, acetic acid, chloroform, dichloromethane, acetone, acetonitrile and diethyl ether, is insoluble in water, is soluble in benzene in a trimer state, is soluble in glacial acetic acid in a single polymer, and is a palladium compound widely used. Besides being used as an important raw material of palladium plating bath liquid and gas sensitive materials and a raw material for synthesizing other palladium compounds, palladium acetate is mainly used as a catalyst which plays a key step in the synthesis of a medicine or a medicine intermediate and is mainly used for olefin aromatization reaction (Heck reaction), cross coupling reaction and Suzuki coupling reaction. And can be applied to alkene carbonylation reaction and reaction of synthesizing ketone by oxidizing alkene and 2-alcohol. The method has great application in the fields of cyclohexanone, adipic acid and caprolactam industry and also has application in the field of nonlinear optical material synthesis.
At present, a method for producing palladium acetate is also disclosed in the related patent literature. As CN 101914005A, a method for preparing a palladium acetate compound; the method is characterized in that the sponge palladium is dissolved and reduced into floating active sponge palladium black, the active sponge palladium black and glacial acetic acid completely react in a reflux way under the condition of no addition of any auxiliary agent, and the reddish brown palladium acetate crystal is prepared by concentrating, crystallizing and drying. CN 106831400A discloses a method for preparing palladium acetate, which comprises the following steps: 1. using metal palladium as a raw material, dissolving the metal palladium by using hydrochloric acid and hydrogen peroxide to obtain a solution, then regulating the pH of the solution by using an alkali solution to obtain a suspension, and continuously stirring for 1h to obtain a reaction solution; 2. and adding glacial acetic acid into the reaction liquid, heating and stirring for reaction, cooling and filtering after the reaction is finished, washing the solid obtained by filtering with water, and drying to obtain palladium acetate. CN 112500282A discloses a method for preparing palladium acetate, which comprises dissolving palladium powder with hydrogen peroxide and hydrochloric acid, then directly adding excessive glacial acetic acid to introduce acetate, adding acetate, adjusting pH to create reaction condition of acetate and palladium ion in mother liquor containing palladium, and finally separating and extracting small amount of palladium acetate dissolved in filtrate.
Disclosure of Invention
The present invention aims to provide a method capable of improving the yield of palladium acetate and its compounds while reducing the loss of palladium.
The technical scheme adopted by the invention for achieving the purpose is as follows:
a method for preparing a palladium acetate compound, comprising:
-preparation of palladium colloid mixed liquor;
preparation of palladium acetate: uniformly mixing the palladium colloid mixed solution with glacial acetic acid and acetate, heating to react, dropwise adding an alkaline solution to adjust the pH of the system to be neutral, continuously stirring for 20-40 min, filtering, washing and drying to obtain a palladium acetate compound;
in the preparation of the palladium colloid mixed solution, calcium cyclohexylsulfamate and a dispersing agent are added;
wherein the dispersing agent is at least one selected from sodium hexametaphosphate, sodium pyrophosphate, sodium dodecyl benzene sulfonate, sodium hexadecyl benzene sulfonate and sodium dodecyl sulfate.
According to the invention, the calcium cyclohexylsulfamate is added in the process of preparing the palladium colloid mixed solution, and interacts with the dispersing agent, so that palladium salt can be promoted to be better dispersed in the solution to form palladium colloid, and the yield of the palladium acetate compound is further improved.
According to one embodiment of the invention, the weight ratio of the calcium hexylsulfamate to the dispersing agent is 0.2-0.5:1.
According to another variant embodiment of the invention, the weight ratio of the calcium cyclohexylsulfamate to the dispersing agent is 0.3-0.5:1; particularly preferably 0.3:1, 0.4:1, 0.5:1. According to the invention, the palladium colloid mixed solution is prepared by utilizing the calcium cyclohexylsulfamate and the dispersing agent in a proper proportion, so that the yield of palladium acetate and compounds thereof is further improved.
According to one embodiment of the invention, the preparation of the palladium colloid mixture is as follows: adding palladium salt and hydrochloric acid solution into a container, adding calcium cyclohexylsulfamate and a dispersing agent, stirring for 5-15min, heating, then dripping a reducing agent, continuously stirring for 1.5-3h, adding alkali liquor to adjust the pH of the system to be neutral, performing rotary evaporation, and filtering to obtain palladium colloid mixed solution.
According to another variation of the invention, in the preparation of the palladium colloid mixed solution, the hydrochloric acid solution exists in an amount which is 3-5 times the weight of the palladium salt; the concentration of the hydrochloric acid solution is 5-10 mol/L.
According to one embodiment of the invention, in the preparation of the palladium colloid mixed solution, the addition amount of the dispersing agent is 0.025-0.045wt% of palladium salt; particularly preferably 0.025wt%, 0.035wt% and 0.045wt%.
According to another variation of the invention, in the preparation of the palladium colloid mixed solution, the addition amount of the reducing agent is 60-90wt% of palladium salt; specifically, 60wt%, 65wt%, 70wt%, 75wt%, 80wt%, 85wt%, and 90wt% are preferable.
According to another variant embodiment of the invention, glacial acetic acid is present in an amount of 1 to 2 times the weight of the palladium colloid mixture.
According to another variant embodiment of the invention, the acetate is present in an amount of 0.1 to 0.3 times the weight of the palladium colloid mixture.
According to one embodiment of the present invention, the palladium acetate compound includes at least one of palladium acetate, a palladium acetate dimer, and a palladium acetate trimer.
Compared with the prior art, the invention has the following beneficial effects:
(a) According to the invention, the calcium cyclohexylsulfamate is added in the process of preparing the palladium colloid mixed solution, and interacts with the dispersing agent, so that palladium salt can be promoted to be better dispersed in the solution to form palladium colloid, and the yield of the palladium acetate compound is further improved.
(b) According to the invention, the palladium colloid mixed solution is prepared by utilizing the calcium cyclohexylsulfamate and the dispersing agent in a proper proportion, so that the yield of palladium acetate and compounds thereof is further improved.
Accordingly, the present invention is a method that can increase palladium acetate and its compounds while reducing palladium loss.
Drawings
FIG. 1 is an infrared spectrum of 1, 3-dimethoxybenzene and an ester compound in example 8.
Detailed Description
The following detailed description of the invention is provided in connection with the accompanying drawings that are presented to illustrate the invention and not to limit the scope thereof. The examples provided below are intended as guidelines for further modifications by one of ordinary skill in the art and are not to be construed as limiting the invention in any way. The experimental methods in the embodiments of the invention are all conventional methods unless otherwise specified; the materials and reagents used, unless otherwise indicated, are commercially available.
According to another embodiment of the invention, a method for preparing a palladium colloid mixture comprises the following steps:
adding palladium salt and hydrochloric acid solution into a container, wherein the hydrochloric acid solution (the concentration is 5-10 mol/L) exists at 3-5 times of the weight of the palladium salt, then adding calcium cyclohexylsulfamate and a dispersing agent (the weight ratio of the calcium hexylsulfamate to the dispersing agent is 0.2-0.5:1), wherein the addition amount of the dispersing agent is 0.025-0.045 wt% of the palladium salt, stirring for 5-15min, heating to 35-55 ℃ for reacting for 2-3 h, then dropwise adding 60-90 wt% of a reducing agent of the palladium salt, continuously stirring for 1.5-3h, adding sodium hydroxide solution with the concentration of 1-2 mol/L to adjust the pH value of the system to 6.5-8.0, performing rotary evaporation at 60-70 ℃ to 1/4-1/5 of the original volume, filtering to remove precipitated crystals, and adding deionized water into filtrate to obtain palladium colloid mixed solution.
According to another variant embodiment of the invention, the reducing agent is selected from at least one of sodium hypophosphite, formic acid, sodium formate and formaldehyde.
According to another embodiment of the present invention, the palladium acetate compound is prepared by: uniformly mixing the palladium colloid mixed solution with glacial acetic acid and acetate, wherein the glacial acetic acid exists in an amount which is 1-2 times the weight of the palladium colloid mixed solution, the acetate exists in an amount which is 0.1-0.3 time the weight of the palladium colloid mixed solution, heating to 55-75 ℃ for 2-3 hours, adding alkali liquor to adjust the pH of the system to be neutral, continuously stirring for 20-40 min, filtering, washing and drying to obtain the palladium acetate compound.
The invention is further illustrated by the following examples, which should not be construed as limiting the invention.
Example 1:
a method for preparing a palladium acetate compound comprising:
-preparation of palladium colloid mixture: adding palladium chloride and hydrochloric acid solution with the concentration of 8mol/L into a container, wherein the hydrochloric acid solution exists at 3.5 times of the weight of palladium salt, then adding calcium cyclohexylsulfamate and sodium dodecylbenzenesulfonate (the weight ratio of the calcium hexylsulfamate to the sodium dodecylbenzenesulfonate is 0.2:1), wherein the addition amount of the sodium dodecylbenzenesulfonate is 0.045wt% of the palladium chloride, heating to 45 ℃ for reaction for 3 hours after stirring for 10 minutes, then dropwise adding 70wt% of sodium hypophosphite of the palladium chloride, continuously stirring for 2 hours, adding sodium hydroxide solution with the concentration of 1mol/L to adjust the pH of the system to 6.5, performing rotary evaporation at 65 ℃ to 1/4 of the original volume, filtering to remove precipitated crystals, and adding deionized water into filtrate to the original volume to obtain palladium colloid mixed solution;
preparation of palladium acetate compound: uniformly mixing the palladium colloid mixed solution, glacial acetic acid and sodium acetate, wherein the glacial acetic acid is 2 times of the weight of the palladium colloid mixed solution, the sodium acetate is 0.1 time of the weight of the palladium colloid mixed solution, heating to 60 ℃ for 2 hours, adding alkali liquor to adjust the pH of the system to be neutral, continuously stirring for 30 minutes, filtering, washing a filter cake with deionized water for 5 times, and drying at 55 ℃ for 12 hours to obtain the palladium acetate compound.
Example 2:
the palladium acetate compound was produced as follows from example 1:
-preparation of palladium colloid mixture: adding palladium chloride and hydrochloric acid solution with the concentration of 10mol/L into a container, wherein the hydrochloric acid solution exists 4.5 times of the weight of palladium salt, then adding calcium cyclohexylsulfamate and sodium dodecylbenzenesulfonate (the weight ratio of the calcium hexylsulfamate to the sodium dodecylbenzenesulfonate is 0.2:1), wherein the adding amount of the sodium dodecylbenzenesulfonate is 0.045wt% of the palladium chloride, heating to 55 ℃ for reaction for 3h after stirring for 10min, then dropwise adding 80wt% of sodium hypophosphite of the palladium chloride, continuously stirring for 2h, adding sodium hydroxide solution with the concentration of 1mol/L to adjust the pH of the system to 7.0, performing rotary evaporation at 65 ℃ to 1/4 of the original volume, filtering to remove precipitated crystals, and adding deionized water into filtrate to the original volume to obtain palladium colloid mixed solution.
The other steps were the same as in example 1.
Example 3:
the palladium acetate compound was produced as follows from example 1:
in the preparation process of the palladium colloid mixed solution, the weight ratio of the calcium hexyl sulfamate to the sodium dodecyl benzene sulfonate is 0.4:1.
The other steps were the same as in example 1.
Example 4:
the palladium acetate compound was produced as follows from example 1:
in the preparation process of the palladium colloid mixed solution, the weight ratio of the calcium hexyl sulfamate to the sodium dodecyl benzene sulfonate is 0.5:1.
The other steps were the same as in example 1.
Example 5:
the palladium acetate compound was produced as follows from example 1:
in the preparation process of the palladium colloid mixed solution, the weight ratio of the calcium hexyl sulfamate to the sodium dodecyl benzene sulfonate is 0.1:1.
The other steps were the same as in example 1.
Example 6:
the palladium acetate compound was produced as follows from example 1:
in the preparation process of the palladium colloid mixed solution, the weight ratio of the calcium hexyl sulfamate to the sodium dodecyl benzene sulfonate is 0.6:1.
The other steps were the same as in example 1.
Example 7:
the palladium acetate compound was produced as follows from example 1:
preparation of palladium acetate compound: uniformly mixing the palladium colloid mixed solution, glacial acetic acid and sodium acetate, wherein the glacial acetic acid exists in an amount which is 1.5 times the weight of the palladium colloid mixed solution, acetate exists in an amount which is 0.15 times the weight of the palladium colloid mixed solution, heating to 70 ℃ for 2 hours, adding alkali liquor to adjust the pH of the system to be neutral, continuously stirring for 30 minutes, filtering, washing a filter cake with deionized water, and drying at 55 ℃ for 12 hours to obtain the palladium acetate compound.
The other steps were the same as in example 1.
Example 8:
the palladium acetate compound is easy to dissolve in glacial acetic acid, so that the difficulty of separation is increased, and more residues possibly exist in the filtrate, so that the mixed solution of the ester compound and isopropanol can be added into the filtrate of the palladium acetate compound, the yield of the palladium acetate and the palladium acetate compound is further improved, and the loss of palladium is reduced; the weight ratio of the ester compound to the isopropanol is 0.5-1:1, the volume of the added mixed solution is 1/8~1/5 of the volume of the filtrate, the mixed solution is filtered, the precipitate obtained by the two times of filtering is washed by deionized water for 5 times, and the palladium acetate compound is obtained by drying. Wherein the structural formula of the ester compound is as follows:
the determination is carried out by using Bruker AVANCE III HD 400, and the solvent is deuterated chloroform; the test nuclear magnetic characterization data are as follows:
1 H NMR(400 MHz, CDCl 3 )：8.12（d，1H）、6.79（s，1H）、6.71（d，1H）、4.23（m，2H）、3.85（s，6H）、1.30（t，3H）。
in another embodiment of the present invention, the ester compound is prepared from 1, 3-dimethoxybenzene and oxalyl chloride monoethyl ester.
The invention also discloses a preparation method of the ester compound, which comprises the following steps: and (3) placing the 1, 3-dimethoxybenzene, oxalyl chloride monoethyl ester and the catalyst in a container, uniformly stirring, heating to 80-90 ℃ and refluxing for 5-8 hours, cooling to room temperature, adding reactants into ice water for hydrolysis, extracting with toluene, and removing the solvent by rotary evaporation to obtain the ester compound.
In another embodiment of the invention, the molar ratio of the 1, 3-dimethoxybenzene, oxalyl chloride monoethyl ester to the catalyst is 1:1-1.5:1-2.
The palladium acetate compound was produced as follows from example 1:
preparation of palladium acetate compound: uniformly mixing the palladium colloid mixed solution, glacial acetic acid and sodium acetate, wherein the glacial acetic acid exists in an amount which is 2 times the weight of the palladium colloid mixed solution, acetate exists in an amount which is 0.1 time the weight of the palladium colloid mixed solution, heating to 60 ℃ for 2 hours, adding alkali liquor to adjust the pH of the system to be neutral, continuously stirring for 30 minutes, filtering, adding an ester compound and isopropanol mixed solution with the volume of 1/6 of the filtrate into the filtrate, wherein the weight ratio of the ester compound to the isopropanol is 0.5:1, combining the filter cakes obtained by the two steps, washing with deionized water for 5 times, and drying at 55 ℃ for 12 hours to obtain the palladium acetate compound.
In this embodiment, the preparation method of the ester compound includes: placing 1, 3-dimethoxy benzene, oxalyl chloride monoethyl ester and a catalyst in a molar ratio of 1:1.5:1.5 into a flask, stirring uniformly, heating to 85 ℃ and refluxing for 6 hours, cooling to room temperature, adding reactants into ice water which is 8 times of the total weight of the reactants for hydrolysis, extracting with toluene, and removing the solvent by rotary evaporation to obtain the ester compound.
The other steps were the same as in example 1.
Example 9:
the palladium acetate compound was produced as follows from example 8:
preparation of palladium acetate compound: uniformly mixing the palladium colloid mixed solution, glacial acetic acid and sodium acetate, wherein the glacial acetic acid exists in an amount which is 2 times the weight of the palladium colloid mixed solution, acetate exists in an amount which is 0.1 time the weight of the palladium colloid mixed solution, heating to 60 ℃ for 2 hours, adding alkali liquor to adjust the pH of the system to be neutral, continuously stirring for 30 minutes, filtering, adding an ester compound and isopropanol mixed solution with the volume of 1/6 of the filtrate into the filtrate, wherein the weight ratio of the ester compound to the isopropanol is 0.8:1, combining the filter cakes of the two times, washing with deionized water for 5 times, and drying at 55 ℃ for 12 hours to obtain the palladium acetate compound.
The other steps were the same as in example 8.
Example 10:
the palladium acetate compound was produced as follows from example 8:
preparation of palladium acetate compound: uniformly mixing the palladium colloid mixed solution, glacial acetic acid and sodium acetate, wherein the glacial acetic acid exists in an amount which is 2 times the weight of the palladium colloid mixed solution, acetate exists in an amount which is 0.1 time the weight of the palladium colloid mixed solution, heating to 60 ℃ for 2 hours, adding alkali liquor to adjust the pH of the system to be neutral, continuously stirring for 30 minutes, filtering, adding an ester compound and isopropanol mixed solution with the volume of 1/6 of the filtrate into the filtrate, wherein the weight ratio of the ester compound to the isopropanol is 1:1, combining the filter cakes of the two times, washing with deionized water for 5 times, and drying at 55 ℃ for 12 hours to obtain the palladium acetate compound.
The other steps were the same as in example 8.
Example 11:
the palladium acetate compound was produced as follows from example 8:
preparation of palladium acetate compound: uniformly mixing the palladium colloid mixed solution, glacial acetic acid and sodium acetate, wherein the glacial acetic acid exists in an amount which is 2 times the weight of the palladium colloid mixed solution, acetate exists in an amount which is 0.1 time the weight of the palladium colloid mixed solution, heating to 60 ℃ for 2 hours, adding alkali liquor to adjust the pH of the system to be neutral, continuously stirring for 30 minutes, filtering, adding an ester compound and isopropanol mixed solution with the volume of 1/6 of the filtrate into the filtrate, wherein the weight ratio of the ester compound to the isopropanol is 0.4:1, combining the filter cakes of the two times, washing with deionized water for 5 times, and drying at 55 ℃ for 12 hours to obtain the palladium acetate compound.
The other steps were the same as in example 8.
Example 12:
the palladium acetate compound was produced as follows from example 8:
preparation of palladium acetate compound: uniformly mixing the palladium colloid mixed solution, glacial acetic acid and sodium acetate, wherein the glacial acetic acid exists in an amount which is 2 times the weight of the palladium colloid mixed solution, acetate exists in an amount which is 0.1 time the weight of the palladium colloid mixed solution, heating to 60 ℃ for 2 hours, adding alkali liquor to adjust the pH of the system to be neutral, continuously stirring for 30 minutes, filtering, adding an ester compound and isopropanol mixed solution with the volume of 1/6 of the filtrate into the filtrate, wherein the weight ratio of the ester compound to the isopropanol is 1.2:1, combining the filter cakes of the two times, washing with deionized water for 5 times, and drying at 55 ℃ for 12 hours to obtain the palladium acetate compound.
The other steps were the same as in example 8.
Example 13:
the palladium acetate compound was produced as follows from example 1:
in the preparation process of the palladium colloid mixed solution, no calcium hexyl sulfamate is added.
The other steps were the same as in example 1.
Example 14:
the palladium acetate compound was produced as follows from example 8:
preparation of palladium acetate compound: uniformly mixing the palladium colloid mixed solution, glacial acetic acid and sodium acetate, wherein the glacial acetic acid exists in an amount which is 2 times the weight of the palladium colloid mixed solution, acetate exists in an amount which is 0.1 time the weight of the palladium colloid mixed solution, heating to 60 ℃ for 2 hours, adding alkali liquor to adjust the pH of the system to be neutral, continuously stirring for 30 minutes, filtering, adding isopropanol with the volume of 1/6 of the filtrate into the filtrate, combining the filter cakes of the two times, washing with deionized water for 5 times, and drying at 55 ℃ for 12 hours to obtain the palladium acetate compound.
The other steps were the same as in example 8.
Example 15:
the palladium acetate compound was produced as follows from example 8:
preparation of palladium acetate compound: uniformly mixing the palladium colloid mixed solution, glacial acetic acid and sodium acetate, wherein the glacial acetic acid exists in an amount which is 2 times the weight of the palladium colloid mixed solution, acetate exists in an amount which is 0.1 time the weight of the palladium colloid mixed solution, heating to 60 ℃ for 2 hours, adding alkali liquor to adjust the pH of the system to be neutral, continuously stirring for 30 minutes, filtering, adding an ester compound with the volume of 1/6 of the filtrate into the filtrate and an absolute ethyl alcohol mixed solution, wherein the weight ratio of the ester compound to the absolute ethyl alcohol is 0.5:1, combining the filter cakes of the two times, washing with deionized water for 5 times, and drying at 55 ℃ for 12 hours to obtain the palladium acetate compound.
The other steps were the same as in example 8.
Example 16:
the palladium acetate compound was produced as follows from example 8:
preparation of palladium acetate compound: uniformly mixing the palladium colloid mixed solution, glacial acetic acid and sodium acetate, wherein the glacial acetic acid exists in an amount which is 2 times the weight of the palladium colloid mixed solution, acetate exists in an amount which is 0.1 time the weight of the palladium colloid mixed solution, heating to 60 ℃ for 2 hours, adding alkali liquor to adjust the pH of the system to be neutral, continuously stirring for 30 minutes, filtering, adding absolute ethyl alcohol with the volume of 1/6 of the filtrate into the filtrate, combining the filter cakes of the two steps, washing with deionized water for 5 times, and drying at 55 ℃ for 12 hours to obtain the palladium acetate compound.
The other steps were the same as in example 8.
Example 17:
the palladium acetate compound was produced as follows from example 13:
preparation of palladium acetate compound: uniformly mixing the palladium colloid mixed solution, glacial acetic acid and sodium acetate, wherein the glacial acetic acid exists in an amount which is 2 times the weight of the palladium colloid mixed solution, acetate exists in an amount which is 0.1 time the weight of the palladium colloid mixed solution, heating to 60 ℃ for 2 hours, adding alkali liquor to adjust the pH of the system to be neutral, continuously stirring for 30 minutes, filtering, adding isopropanol with the volume of 1/6 of the filtrate into the filtrate, combining the filter cakes of the two times, washing with deionized water for 5 times, and drying at 55 ℃ for 12 hours to obtain the palladium acetate compound.
The other steps were the same as in example 13.
Example 18:
the palladium acetate compound was produced as follows from example 13:
preparation of palladium acetate compound: uniformly mixing the palladium colloid mixed solution, glacial acetic acid and sodium acetate, wherein the glacial acetic acid exists in an amount which is 2 times the weight of the palladium colloid mixed solution, acetate exists in an amount which is 0.1 time the weight of the palladium colloid mixed solution, heating to 60 ℃ for 2 hours, adding alkali liquor to adjust the pH of the system to be neutral, continuously stirring for 30 minutes, filtering, adding absolute ethyl alcohol with the volume of 1/6 of the filtrate into the filtrate, combining the filter cakes of the two steps, washing with deionized water for 5 times, and drying at 55 ℃ for 12 hours to obtain the palladium acetate compound.
The other steps were the same as in example 13.
[ test example 1 ]
i.IR structural characterization
Infrared characterization is carried out on the prepared ester compound by adopting a Fourier transform infrared spectrometer, and the scanning range is 4000-500 cm -1 。
FIG. 1 is an infrared spectrum of 1, 3-dimethoxybenzene and an ester compound in example 8; curves a and b are respectively 1, 3-dimethoxy benzene and ester compounds; as can be seen from FIG. 1, 3-dimethoxybenzene at 3080cm -1 Characteristic suction occurring nearbyThe peak is the expansion and contraction vibration of hydrocarbon in the benzene ring; at 1500cm -1 The characteristic absorption peak appearing nearby is the stretching vibration of carbon-carbon double bond in benzene ring; the ester compound is 1725cm relative to 1, 3-dimethoxy benzene -1 The characteristic absorption peak appearing nearby is the stretching vibration of the ester group; therefore, the ester compound is prepared by 1, 3-dimethoxy benzene and oxalyl chloride monoethyl ester.
Palladium acetate and the yields of the compounds thereof
The palladium acetate compounds obtained in examples 1 to 19 were subjected to ICP elemental analysis and detection to determine the yields of palladium acetate and its compounds in the palladium acetate compounds; wherein the palladium acetate compound comprises a palladium acetate dimer and a palladium acetate trimer.
Table 1 yields of palladium acetate and its compounds in the examples
As can be seen from Table 1, the total yield of palladium acetate and its compounds in examples 1-4 is higher than 95%, and the total yields of palladium acetate and its compounds in examples 1,3 and 4 are higher than 97%, which are higher than those in examples 5, 6 and 13, respectively, which means that palladium acetate and its compounds with higher yields are obtained when calcium cyclohexylsulfamate is added during the preparation of the palladium colloid mixture and the weight ratio of calcium cyclohexylsulfamate to the dispersant is 0.2-0.5:1.
As can also be seen from Table 1, the overall yield of palladium acetate and its compounds in examples 8-10 is higher than 98%, the overall yield of palladium acetate and its compounds in examples 1-10, comparative examples 1 and 8-10 is higher than example 1 and higher than examples 11-12, the overall yield of palladium acetate and its compounds in examples 8 and 14-16, examples 13 and 17-18, and the overall yield of palladium acetate and its compounds in example 8 is higher than examples 14-16, and the overall yield of palladium acetate and its compounds in example 13 is higher than examples 17-18, indicating that the addition of ester compound and isopropyl alcohol to the filtrate during the preparation of palladium acetate compound, and the weight ratio of ester compound and isopropyl alcohol is 0.5-1:1, further improves the overall yield of palladium acetate and its compounds.
In addition, the residual palladium in the filtrate in examples 8-10 was less than 1.3%, the loss of palladium was less than 1%, and the residual palladium content and the loss of palladium in the filtrate in examples 8-10 were less than those in examples 8-10, indicating that the addition of the ester compound and isopropyl alcohol to the filtrate may be able to separate the palladium dissolved in glacial acetic acid better, thereby reducing the content of palladium dissolved in the filtrate and reducing the loss rate of palladium.
Conventional operations in the operation steps of the present invention are well known to those skilled in the art, and are not described herein.
While the foregoing embodiments have been described in detail in connection with the embodiments of the invention, it should be understood that the foregoing embodiments are merely illustrative of the invention and are not intended to limit the invention, and any modifications, additions, substitutions and the like made within the principles of the invention are intended to be included within the scope of the invention.
Claims (10)
1. A method for preparing a palladium acetate compound, comprising:
-preparation of palladium colloid mixed liquor;
preparation of palladium acetate compound: uniformly mixing the palladium colloid mixed solution with glacial acetic acid and acetate, heating for reaction, dropwise adding an alkaline solution to adjust the pH of the system to be neutral, continuously stirring for 20-40 min, filtering, washing and drying to obtain a palladium acetate compound;
in the preparation of the palladium colloid mixed solution, calcium cyclohexylsulfamate and a dispersing agent are added;
the dispersing agent is at least one selected from sodium hexametaphosphate, sodium pyrophosphate, sodium dodecyl benzene sulfonate, sodium hexadecyl benzene sulfonate and sodium dodecyl sulfate.
2. The method for producing a palladium acetate compound according to claim 1, wherein: the weight ratio of the calcium cyclamate to the dispersing agent is 0.2-0.5:1.
3. The method for producing a palladium acetate compound according to claim 2, characterized in that: the weight ratio of the calcium cyclamate to the dispersing agent is 0.3-0.5:1.
4. The method for producing a palladium acetate compound according to claim 1, wherein: the preparation method of the palladium colloid mixed solution comprises the following steps: adding palladium salt and hydrochloric acid solution into a container, adding calcium cyclohexylsulfamate and a dispersing agent, stirring for 5-15min, heating, then dripping a reducing agent, continuously stirring for 1.5-3h, adding alkali liquor to regulate the pH of the system, performing rotary evaporation, and filtering to obtain palladium colloid mixed solution.
5. The method for producing a palladium acetate compound according to claim 4, wherein: in the preparation of the palladium colloid mixed solution, the hydrochloric acid solution exists in an amount which is 3-5 times of the weight of the palladium salt; the concentration of the hydrochloric acid solution is 5-10 mol/L.
6. The method for producing a palladium acetate compound according to claim 4, wherein: in the preparation of the palladium colloid mixed solution, the addition amount of the dispersing agent is 0.025-0.045 wt% of palladium salt.
7. The method for producing a palladium acetate compound according to claim 4, wherein: in the preparation of the palladium colloid mixed solution, the addition amount of the reducing agent is 60-90 wt% of palladium salt.
8. The method for producing a palladium acetate compound according to claim 1, wherein: the glacial acetic acid is 1-2 times of the weight of the palladium colloid mixed solution.
9. The method for producing a palladium acetate compound according to claim 1, wherein: the acetate exists in an amount which is 0.1 to 0.3 time the weight of the palladium colloid mixed solution.
10. The method for producing a palladium acetate compound according to claim 1, wherein: the palladium acetate compound includes at least one of palladium acetate, a palladium acetate dimer, and a palladium acetate trimer.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5332646A (en) * | 1992-10-21 | 1994-07-26 | Minnesota Mining And Manufacturing Company | Method of making a colloidal palladium and/or platinum metal dispersion |
| JP2006342378A (en) * | 2005-06-07 | 2006-12-21 | Ne Chemcat Corp | METHOD FOR PRODUCING Pd COLLOIDAL SOLUTION |
| CN106220494A (en) * | 2016-08-10 | 2016-12-14 | 陕西瑞科新材料股份有限公司 | A kind of palladium trimer preparation method |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5332646A (en) * | 1992-10-21 | 1994-07-26 | Minnesota Mining And Manufacturing Company | Method of making a colloidal palladium and/or platinum metal dispersion |
| JP2006342378A (en) * | 2005-06-07 | 2006-12-21 | Ne Chemcat Corp | METHOD FOR PRODUCING Pd COLLOIDAL SOLUTION |
| CN106220494A (en) * | 2016-08-10 | 2016-12-14 | 陕西瑞科新材料股份有限公司 | A kind of palladium trimer preparation method |
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| CN117623908A (en) * | 2023-11-28 | 2024-03-01 | 云南弘盛铂业新材料科技有限公司 | Method for preparing palladium trifluoroacetate |
| CN117623908B (en) * | 2023-11-28 | 2024-08-02 | 云南弘盛铂业新材料科技有限公司 | Method for preparing palladium trifluoroacetate |
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