CN114315912A - Preparation method of cis-dichlorobis (diethyl sulfide) platinum (II) - Google Patents
Preparation method of cis-dichlorobis (diethyl sulfide) platinum (II) Download PDFInfo
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- CN114315912A CN114315912A CN202111620757.7A CN202111620757A CN114315912A CN 114315912 A CN114315912 A CN 114315912A CN 202111620757 A CN202111620757 A CN 202111620757A CN 114315912 A CN114315912 A CN 114315912A
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- platinum
- dichlorobis
- diethyl sulfide
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- potassium
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- DCIVLRIRJUWCIS-UHFFFAOYSA-L ethylsulfanylethane;platinum(2+);dichloride Chemical compound [Cl-].[Cl-].[Pt+2].CCSCC.CCSCC DCIVLRIRJUWCIS-UHFFFAOYSA-L 0.000 title claims abstract description 39
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 239000000243 solution Substances 0.000 claims abstract description 47
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims abstract description 40
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 40
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims abstract description 35
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 35
- 239000011591 potassium Substances 0.000 claims abstract description 35
- LJSQFQKUNVCTIA-UHFFFAOYSA-N diethyl sulfide Chemical compound CCSCC LJSQFQKUNVCTIA-UHFFFAOYSA-N 0.000 claims abstract description 20
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 20
- 235000011164 potassium chloride Nutrition 0.000 claims abstract description 20
- 239000001103 potassium chloride Substances 0.000 claims abstract description 20
- 239000002253 acid Substances 0.000 claims abstract description 19
- 239000002904 solvent Substances 0.000 claims abstract description 15
- 239000000725 suspension Substances 0.000 claims abstract description 14
- 239000012074 organic phase Substances 0.000 claims abstract description 12
- 239000007864 aqueous solution Substances 0.000 claims abstract description 9
- 239000003638 chemical reducing agent Substances 0.000 claims abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910002651 NO3 Inorganic materials 0.000 claims abstract description 7
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims abstract description 7
- QZPSXPBJTPJTSZ-UHFFFAOYSA-N aqua regia Chemical compound Cl.O[N+]([O-])=O QZPSXPBJTPJTSZ-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000012043 crude product Substances 0.000 claims abstract description 7
- 238000007865 diluting Methods 0.000 claims abstract description 7
- 238000000605 extraction Methods 0.000 claims abstract description 7
- 238000001035 drying Methods 0.000 claims abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 9
- 239000002244 precipitate Substances 0.000 claims description 9
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 7
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 6
- BIVUUOPIAYRCAP-UHFFFAOYSA-N aminoazanium;chloride Chemical compound Cl.NN BIVUUOPIAYRCAP-UHFFFAOYSA-N 0.000 claims description 5
- 238000004821 distillation Methods 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- 235000006408 oxalic acid Nutrition 0.000 claims description 2
- 238000001291 vacuum drying Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 6
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000002994 raw material Substances 0.000 abstract description 6
- 238000009776 industrial production Methods 0.000 abstract description 3
- 239000000047 product Substances 0.000 abstract description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229960001701 chloroform Drugs 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000002815 homogeneous catalyst Substances 0.000 description 2
- 238000006459 hydrosilylation reaction Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- LIAWOTKNAVAKCX-UHFFFAOYSA-N hydrazine;dihydrochloride Chemical compound Cl.Cl.NN LIAWOTKNAVAKCX-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
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- Manufacture And Refinement Of Metals (AREA)
Abstract
The invention relates to a preparation method of cis-dichlorobis (diethyl sulfide) platinum (II), which comprises the following steps: (1) dissolving the platinum sheet with aqua regia, concentrating to remove nitrate, and diluting with water to obtain chloroplatinic acid solution; (2) dropwise adding the obtained chloroplatinic acid solution into a potassium chloride solution to prepare a potassium chloroplatinate suspension; (3) dropwise adding an aqueous solution of a reducing agent into the potassium chloroplatinate suspension to obtain a potassium chloroplatinate solution; (4) adding diethyl sulfide into the potassium chloroplatinite solution to obtain a cis-dichlorobis (diethyl sulfide) platinum (II) crude product; (5) adding a solvent for extraction, standing and separating to obtain an organic phase, removing the solvent in the organic phase, and drying in vacuum to obtain cis-dichlorobis (diethyl sulfide) platinum (II). According to the invention, the platinum sheet is used as a raw material, so that the raw material cost and the time cost are greatly reduced, the industrial production is facilitated, the obtained product has high purity and high yield, and the technical problem of high cost of the existing preparation method is effectively solved.
Description
Technical Field
The invention relates to the technical field of platinum homogeneous catalysts, in particular to a preparation method of cis-dichlorobis (diethyl sulfide) platinum (II).
Background
Hydrosilylation reactions are important reactions to produce a variety of organosilicon compounds, with the most common catalyst in such reactions being a platinum homogeneous catalyst. The earliest homogeneous platinum catalyst used in this type of reaction was chloroplatinic acid, and cis-dichlorobis (diethylsulfide) platinum (II) was subsequently reported to be more efficient at catalyzing some hydrosilation reactions.
In the prior art, the preparation method of cis-dichlorobis (diethyl sulfide) platinum (II) takes potassium tetrachloroplatinate as a raw material, adds diethyl sulfide after adding water to dissolve the potassium tetrachloroplatinate, and forms yellow precipitate; stirring until the yellow precipitate (trans-isomer) is completely dissolved to obtain a clear yellow solution; the resulting clear yellow solution was reduced to dryness by applying vacuum at 25 ℃ to produce a yellow-white precipitate; extracting the mixture of isomers from the residue by treatment with a small amount of hot benzene; the hot solution was filtered on a hot funnel to remove KCl; after filtration, the benzene solution was evaporated to half volume and cooled in an ice bath, followed by formation of fine yellow crystals of the cis-isomer; the crystals were isolated by suction filtration and washed with hexane to remove any trans isomer, thus obtaining cis-dichlorobis (diethylsulfide) platinum (II). The preparation method takes expensive potassium tetrachloroplatinate as a raw material, has high cost and is not beneficial to industrial production.
Therefore, the prior art has a larger improvement space.
Disclosure of Invention
The invention aims to make up the defects of the prior art and provides a preparation method of cis-dichlorobis (diethyl sulfide) platinum (II).
In order to achieve the purpose, the invention is realized by the following technical scheme:
a preparation method of cis-dichlorobis (diethyl sulfide) platinum (II) comprises the following steps:
(1) dissolving the platinum sheet with aqua regia, concentrating to remove nitrate, and diluting with water to obtain chloroplatinic acid solution;
(2) dropwise adding the obtained chloroplatinic acid solution into a potassium chloride solution, and reacting at 50-70 ℃ until precipitates are not separated out any more to obtain a potassium chloroplatinate suspension;
(3) dropwise adding an aqueous solution of a reducing agent into the potassium chloroplatinate suspension, and reacting at 70-90 ℃ to obtain a potassium chloroplatinate solution;
(4) adding diethyl sulfide into the potassium chloroplatinite solution, and reacting at 70-90 ℃ to obtain a cis-dichloro bis (diethyl sulfide) platinum (II) crude product;
(5) and (3) cooling to room temperature, adding a solvent for extraction, standing and separating to obtain an organic phase, removing the solvent in the organic phase, and then drying in vacuum to obtain cis-dichlorobis (diethyl sulfide) platinum (II).
According to the scheme, the mass content of platinum in the chloroplatinic acid solution in the step (1) is 15-25%.
According to the scheme, the mass concentration of the potassium chloride in the step (2) is 10-20%, and the mass ratio of the potassium chloride to the platinum in the chloroplatinic acid solution is (1.1-1.2): 1.
according to the scheme, the reducing agent in the step (3) is one of oxalic acid, hydrazine hydrochloride, hydrazine monohydrochloride and hydroxylamine hydrochloride.
According to the scheme, the mass concentration of the reducing agent aqueous solution in the step (3) is 10-25%, the mass ratio of the potassium chloroplatinate to the reducing agent is 1:0.2-0.3, and the reaction time is 2-3 hours.
According to the scheme, the molar ratio of the diethyl sulfide to the potassium chloroplatinite in the step (4) is 1.01-1.1:1, and the reaction time is 2-3 hours.
According to the scheme, the solvent in the step (5) is one of dichloromethane, trichloromethane and n-hexane.
According to the above scheme, the solvent in the organic phase is removed by distillation in step (5), and the temperature of distillation and vacuum drying is 50-75 ℃.
The invention has the beneficial effects that:
according to the invention, the platinum sheet is used as a raw material and reacts in the same system all the time, so that the raw material cost and the time cost are greatly reduced, the industrial production is facilitated, inorganic impurities generated in the reaction process are extracted by a solvent and remain in a water phase, the obtained product has high purity and high yield, and the technical problem of high cost of the existing preparation method is effectively solved.
Detailed Description
In order to better understand the present invention, the following examples are further provided to illustrate the content of the present invention, but the present invention is not limited to the following examples.
Example 1
A preparation method of cis-dichlorobis (diethyl sulfide) platinum (II) comprises the following steps:
(1) dissolving 17g of platinum in aqua regia, concentrating, removing nitrate, and diluting with water to obtain a chloroplatinic acid solution with the mass content of platinum being 20%;
(2) dropwise adding the obtained chloroplatinic acid solution into a potassium chloride solution with the mass concentration of 15%, and reacting at 70 ℃ until precipitates are not separated out any more to obtain a potassium chloroplatinate suspension; wherein the potassium chloride solution contains 18.7g of potassium chloride;
(3) dripping 12.5g of hydroxylamine hydrochloride aqueous solution with the mass concentration of 15% into the potassium chloroplatinate suspension, and reacting for 2h at 70 ℃ to obtain a potassium chloroplatinite solution;
(4) adding 11.5g of diethyl sulfide into the potassium chloroplatinite solution, and reacting for 2 hours at 70 ℃ to obtain a cis-dichloro bis (diethyl sulfide) platinum (II) crude product;
(5) after cooling to room temperature, 60mL of methylene chloride was added for extraction, and the mixture was allowed to stand for liquid separation to obtain an organic phase, which was distilled at 50 ℃ to remove the solvent and then dried under vacuum at 50 ℃ to obtain 37.03g of cis-dichlorobis (diethyl sulfide) platinum (II).
The cis-dichlorobis (diethyl sulfide) platinum (II) obtained in the example was determined to have a purity of 98.5% and a yield of 95.2%.
Example 2
A preparation method of cis-dichlorobis (diethyl sulfide) platinum (II) comprises the following steps:
(1) dissolving 17g of platinum in aqua regia, concentrating, removing nitrate, and diluting with water to obtain a chloroplatinic acid solution with the mass content of platinum being 15%;
(2) dropwise adding the obtained chloroplatinic acid solution into a potassium chloride solution with the mass concentration of 20%, and reacting at 60 ℃ for 2.5 hours until precipitates are not separated out any more to obtain a potassium chloroplatinate suspension; wherein the potassium chloride solution contains 13.5g of potassium chloride;
(3) dropwise adding 14.2g of hydrazine hydrochloride aqueous solution with the mass concentration of 17% into the potassium chloroplatinate suspension, and reacting for 2h at 70 ℃ to obtain a potassium chloroplatinite solution;
(4) adding 11.5g of diethyl sulfide into the potassium chloroplatinite solution, and reacting for 2 hours at 70 ℃ to obtain a cis-dichloro bis (diethyl sulfide) platinum (II) crude product;
(5) after cooling to room temperature, 60mL of n-hexane was added for extraction, and the mixture was allowed to stand and separate to obtain an organic phase, which was distilled at 75 ℃ to remove the solvent and then dried under vacuum at 75 ℃ to obtain 36.83g of cis-dichlorobis (diethylsulfide) platinum (II).
The cis-dichlorobis (diethyl sulfide) platinum (II) obtained in this example was found to have a purity of 97.8% and a yield of 94.7%.
Example 3
A preparation method of cis-dichlorobis (diethyl sulfide) platinum (II) comprises the following steps:
(1) dissolving 35g of platinum in aqua regia, concentrating, removing nitrate, and diluting with water to obtain a chloroplatinic acid solution with the mass content of platinum being 15%;
(2) dropwise adding the obtained chloroplatinic acid solution into a potassium chloride solution with the mass concentration of 20%, and reacting at 65 ℃ for 2.5 hours until precipitates are not separated out any more to obtain a potassium chloroplatinate suspension; wherein the potassium chloride solution contains 36.3g of potassium chloride;
(3) dripping 12.5g of hydroxylamine hydrochloride aqueous solution with the mass concentration of 15% into the potassium chloroplatinate suspension, and reacting for 2h at 85 ℃ to obtain a potassium chloroplatinite solution;
(4) adding 11.5g of diethyl sulfide into the potassium chloroplatinite solution, and reacting for 2 hours at 80 ℃ to obtain a cis-dichloro bis (diethyl sulfide) platinum (II) crude product;
(5) after cooling to room temperature, 60mL of chloroform was added for extraction, and the mixture was allowed to stand for liquid separation to obtain an organic phase, which was distilled at 65 ℃ to remove the solvent and then dried under vacuum at 60 ℃ to obtain 73.36g of cis-dichlorobis (diethylsulfide) platinum (II).
The cis-dichlorobis (diethyl sulfide) platinum (II) obtained in the example was determined to have a purity of 98.3% and a yield of 94.6%.
Example 4
A preparation method of cis-dichlorobis (diethyl sulfide) platinum (II) comprises the following steps:
(1) dissolving 35g of platinum in aqua regia, concentrating, removing nitrate, and diluting with water to obtain a chloroplatinic acid solution with the mass content of platinum being 25%;
(2) dropwise adding the obtained chloroplatinic acid solution into a potassium chloride solution with the mass concentration of 15%, and reacting for 3 hours at 75 ℃ until precipitates are not separated out any more, so as to obtain a potassium chloroplatinate suspension; wherein the potassium chloride solution contains 38.3g of potassium chloride;
(3) dropwise adding 28g of 15% hydrazine dihydrochloride aqueous solution into the potassium chloroplatinate suspension, and reacting for 3h at 75 ℃ to obtain a potassium chloroplatinite solution;
(4) adding 13.5g of diethyl sulfide into the potassium chloroplatinite solution, and reacting for 2h at 75 ℃ to obtain a cis-dichloro bis (diethyl sulfide) platinum (II) crude product;
(5) after cooling to room temperature, 60mL of chloroform was added for extraction, and the mixture was allowed to stand for liquid separation to obtain an organic phase, which was distilled at 65 ℃ to remove the solvent and then dried under vacuum at 70 ℃ to obtain 74.06g of cis-dichlorobis (diethylsulfide) platinum (II).
The cis-dichlorobis (diethyl sulfide) platinum (II) obtained in the example was determined to have a purity of 98.1% and a yield of 95.3%.
The above description is only a preferred embodiment of the present invention, and all equivalent changes or modifications of the structure, characteristics and principles described in the present invention are included in the scope of the present invention.
Claims (8)
1. A preparation method of cis-dichlorobis (diethyl sulfide) platinum (II) is characterized by comprising the following steps:
(1) dissolving the platinum sheet with aqua regia, concentrating to remove nitrate, and diluting with water to obtain chloroplatinic acid solution;
(2) dropwise adding the obtained chloroplatinic acid solution into a potassium chloride solution, and reacting at 50-70 ℃ until precipitates are not separated out any more to obtain a potassium chloroplatinate suspension;
(3) dropwise adding an aqueous solution of a reducing agent into the potassium chloroplatinate suspension, and reacting at 70-90 ℃ to obtain a potassium chloroplatinate solution;
(4) adding diethyl sulfide into the potassium chloroplatinite solution, and reacting at 70-90 ℃ to obtain a cis-dichloro bis (diethyl sulfide) platinum (II) crude product;
(5) and (3) cooling to room temperature, adding a solvent for extraction, standing and separating to obtain an organic phase, removing the solvent in the organic phase, and then drying in vacuum to obtain cis-dichlorobis (diethyl sulfide) platinum (II).
2. The method for preparing cis-dichlorobis (diethyl sulfide) platinum (II) according to claim 1, wherein the mass content of platinum in the chloroplatinic acid solution in the step (1) is 15 to 25%.
3. The method for preparing cis-dichlorobis (diethyl sulfide) platinum (ii) according to claim 1, wherein the mass concentration of potassium chloride in the step (2) is 10% to 20%, and the ratio of the mass of potassium chloride to the mass of platinum in the chloroplatinic acid solution is (1.1 to 1.2): 1.
4. the method for preparing cis-dichlorobis (diethyl sulfide) platinum (II) as claimed in claim 1, wherein the reducing agent in step (3) is one of oxalic acid, hydrazine hydrochloride, hydrazine monohydrochloride and hydroxylamine hydrochloride.
5. The method for preparing cis-dichlorobis (diethyl sulfide) platinum (II) according to claim 1, wherein the mass concentration of the aqueous solution of the reducing agent in the step (3) is 10-25%, the mass ratio of potassium chloroplatinate to the reducing agent is 1:0.2-0.3, and the reaction time is 2-3 hours.
6. The method for preparing cis-dichlorobis (diethyl sulfide) platinum (II) according to claim 1, wherein the molar ratio of diethyl sulfide to potassium chloroplatinite in step (4) is 1.01-1.1:1, and the reaction time is 2-3 hours.
7. The method for preparing cis-dichlorobis (diethyl sulfide) platinum (II) according to claim 1, wherein the solvent in step (5) is one of dichloromethane, chloroform and n-hexane.
8. The process for preparing cis-dichlorobis (diethylsulfide) platinum (II) as claimed in claim 1, wherein the solvent in the organic phase is removed by distillation in step (5), and the temperature for distillation and vacuum drying is 50-75 ℃.
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| CN202111620757.7A CN114315912A (en) | 2021-12-28 | 2021-12-28 | Preparation method of cis-dichlorobis (diethyl sulfide) platinum (II) |
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03131529A (en) * | 1989-10-13 | 1991-06-05 | Tanaka Kikinzoku Kogyo Kk | Production of potassium tetrachloroplatinate |
| CN101279772A (en) * | 2008-05-15 | 2008-10-08 | 金川集团有限公司 | Preparation of potassium platinochloride |
| CN102390874A (en) * | 2011-08-01 | 2012-03-28 | 山东铂源化学有限公司 | Preparation method of potassium chloroplatinite |
| CN103253718A (en) * | 2013-05-24 | 2013-08-21 | 陕西煤业化工技术开发中心有限责任公司 | Preparation method of potassium chloroplatinite |
| CN109761290A (en) * | 2019-03-15 | 2019-05-17 | 西安凯立新材料股份有限公司 | A kind of preparation method of potassium chloroplatinite |
-
2021
- 2021-12-28 CN CN202111620757.7A patent/CN114315912A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03131529A (en) * | 1989-10-13 | 1991-06-05 | Tanaka Kikinzoku Kogyo Kk | Production of potassium tetrachloroplatinate |
| CN101279772A (en) * | 2008-05-15 | 2008-10-08 | 金川集团有限公司 | Preparation of potassium platinochloride |
| CN102390874A (en) * | 2011-08-01 | 2012-03-28 | 山东铂源化学有限公司 | Preparation method of potassium chloroplatinite |
| CN103253718A (en) * | 2013-05-24 | 2013-08-21 | 陕西煤业化工技术开发中心有限责任公司 | Preparation method of potassium chloroplatinite |
| CN109761290A (en) * | 2019-03-15 | 2019-05-17 | 西安凯立新材料股份有限公司 | A kind of preparation method of potassium chloroplatinite |
Non-Patent Citations (1)
| Title |
|---|
| 王建青等: "顺式-和反式-二氯二(乙硫醚)合铂(Ⅱ)的合成和结构表征", 《贵金属》 * |
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Application publication date: 20220412 |