CN114029092A - Synthesis method of metal catalyst - Google Patents
Synthesis method of metal catalyst Download PDFInfo
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- CN114029092A CN114029092A CN202111626739.XA CN202111626739A CN114029092A CN 114029092 A CN114029092 A CN 114029092A CN 202111626739 A CN202111626739 A CN 202111626739A CN 114029092 A CN114029092 A CN 114029092A
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- 239000003054 catalyst Substances 0.000 title claims abstract description 28
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 24
- 239000002184 metal Substances 0.000 title claims abstract description 24
- 238000001308 synthesis method Methods 0.000 title claims abstract description 14
- 239000003960 organic solvent Substances 0.000 claims abstract description 58
- 238000006243 chemical reaction Methods 0.000 claims abstract description 29
- 239000012046 mixed solvent Substances 0.000 claims abstract description 23
- 239000000706 filtrate Substances 0.000 claims abstract description 21
- 238000001914 filtration Methods 0.000 claims abstract description 17
- 238000010992 reflux Methods 0.000 claims abstract description 14
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 claims abstract description 12
- YILMOQBPBZHHFY-UHFFFAOYSA-L C(C)(C)[Ru](C1=CC=CC=C1)(Cl)Cl Chemical compound C(C)(C)[Ru](C1=CC=CC=C1)(Cl)Cl YILMOQBPBZHHFY-UHFFFAOYSA-L 0.000 claims abstract description 9
- 238000003756 stirring Methods 0.000 claims abstract description 9
- UCXDWSTYBSBFFB-UHFFFAOYSA-L 1-methyl-4-propan-2-ylbenzene;ruthenium(2+);dichloride Chemical compound Cl[Ru]Cl.CC(C)C1=CC=C(C)C=C1 UCXDWSTYBSBFFB-UHFFFAOYSA-L 0.000 claims abstract description 8
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical group C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000012065 filter cake Substances 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims abstract description 5
- 238000004321 preservation Methods 0.000 claims abstract description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 24
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
- 239000000047 product Substances 0.000 claims description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 238000001816 cooling Methods 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 238000005406 washing Methods 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 239000003208 petroleum Substances 0.000 claims description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- DHCWLIOIJZJFJE-UHFFFAOYSA-L dichlororuthenium Chemical compound Cl[Ru]Cl DHCWLIOIJZJFJE-UHFFFAOYSA-L 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 239000003446 ligand Substances 0.000 claims description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 4
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- 239000012295 chemical reaction liquid Substances 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 2
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 2
- 229940011051 isopropyl acetate Drugs 0.000 claims description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 230000002194 synthesizing effect Effects 0.000 claims 7
- 239000002904 solvent Substances 0.000 abstract description 11
- 238000009776 industrial production Methods 0.000 abstract description 2
- 239000007787 solid Substances 0.000 description 6
- 239000012141 concentrate Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000012467 final product Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- YAYGSLOSTXKUBW-UHFFFAOYSA-N ruthenium(2+) Chemical compound [Ru+2] YAYGSLOSTXKUBW-UHFFFAOYSA-N 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- -1 biology Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 201000005202 lung cancer Diseases 0.000 description 1
- 208000020816 lung neoplasm Diseases 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Images
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
- B01J31/2409—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/821—Ruthenium
Abstract
The invention relates to a synthesis method of a metal catalyst, wherein the catalyst is [ (S) -BINAPPUCl 2(p-cymene ]/[ (S) - (-) -2,2 '-bis (diphenylphosphino) -1, 1' -binaphthyl ] (p-cymene) ruthenium dichloride, isopropylphenyl ruthenium dichloride, (S) -BINAP and a first organic solvent, the mixture is heated to reflux and is subjected to heat preservation reaction, the reaction is cooled and filtered, the filter cake is washed by the first organic solvent, the filtrate is combined and is decompressed and concentrated, an isometric mixed solvent is added for reconcentration, the mixture is cooled to room temperature, the stirring and the filtration are carried out, the mixed solvent is washed and dried to obtain the catalyst, the mixed solvent is a second solvent and a third solvent, the synthesis method of the metal catalyst has the advantages of simple operation, low equipment requirement and mild reaction conditions, high yield and content, and is suitable for industrial production.
Description
Technical Field
The invention belongs to the technical field of metal organic catalysis, and particularly relates to a synthesis method of a metal catalyst.
Background
The transition metal ruthenium (II) complex and a ligand form a hexa-coordinated octahedral configuration complex, the complex is a triplet luminophor, has good optical performance, can excite and emit light with adjustable wavelength, has the advantages of long emission wavelength, long fluorescence life, large Stokes shift and the like, and therefore, the transition metal ruthenium (II) complex is closely concerned by people, and is rapidly developed in application research on materials, biology, medicines and the like.
Wherein, the synthesis of the fourth-generation lung cancer targeted drug eai045 bulk drug generally adopts a metal ruthenium catalyst: [ (S) -BINAP RuCl2 (p-cymene]/[ (S) - (-) -2,2 '-bis (diphenylphosphino) -1, 1' -binaphthyl]The existing synthesis method of (p-cymene) ruthenium dichloride generally comprises the steps of carrying out ligand exchange reaction on (S) -BINAP under the reflux state of an organic solvent to obtain a catalyst product, filtering, concentrating and crystallizing with n-heptane to obtain a product, wherein the purity of the product obtained by sequentially filtering, concentrating and crystallizing with n-heptane is not high, the crystallized crystal form is unstable, and the product stability is not good.
Disclosure of Invention
The invention aims to provide a synthesis method of a metal catalyst, which has the advantages of easily obtained reaction raw materials, simple operation of the reaction process, low requirement on reaction equipment, relatively mild reaction conditions, stable quality, high yield and high content of the catalyst product, and the content of the finally obtained metal catalyst is more than 99 percent.
The technical scheme adopted by the invention for solving the problems is as follows: a synthesis method of a metal catalyst, wherein the metal catalyst is [ (S) -BINAP RuCl2 (p-cymene]/[ (S) - (-) -2,2 '-bis (diphenylphosphino) -1, 1' -binaphthyl]The synthesis method of (p-cymene) ruthenium dichloride takes isopropylphenyl ruthenium dichloride as a starting material and is prepared by ligand exchange reaction, and comprises the following steps:
(1) under the condition of nitrogen, sequentially adding isopropylphenyl ruthenium dichloride, (S) -BINAP and a first organic solvent, heating to reflux, carrying out heat preservation and reflux reaction, and cooling reaction liquid after the reaction;
(2) filtering the reaction solution cooled in the step (1), washing a filter cake with a first organic solvent, and combining filtrates;
(3) concentrating the combined filtrates in the step (2) under reduced pressure to 1/5-1/2 volume of the total volume of the filtrates to obtain a first concentrated solution, adding a mixed solvent of a second organic solvent and a third organic solvent with the same volume, concentrating to 1/5-1/2 volume to obtain a second concentrated solution, adding a mixed solvent of the second organic solvent and the third organic solvent with the same volume, and continuously concentrating to 1/2-4/5 volume of the total volume of the filtrates to obtain a third concentrated solution;
(4) cooling the concentrated solution obtained in the step (3) to room temperature, stirring at room temperature, filtering, washing with a mixed solvent of a second organic solvent and a third organic solvent to obtain a light yellow to light brown crystalline solid, and vacuum-drying to obtain light yellow crystalline solid powder;
wherein the first organic solvent is one of methanol, ethanol, isopropanol, tetrahydrofuran and 2-methyltetrahydrofuran;
the second organic solvent is one of ethyl acetate, isopropyl ether, diethyl ether, isopropyl acetate, n-propyl acetate, butyl acetate and 1, 4-dioxane.
The third organic solvent is one of n-heptane, n-hexane, cyclohexane and petroleum ether.
The reaction formula of the synthesis method is shown as follows:
preferably, the volume ratio of the second organic solvent to the third organic solvent in the mixed solvent is 1: 1.
Preferably, the molar ratio of isopropylphenyl ruthenium dichloride and (S) -BINAP in step (1) is 1: 2 to 2.9.
Preferably, the heat-preservation reflux time in the step (1) is 2-5 hours.
Preferably, the reaction solution in step (1) is cooled to 20. + -. 5 ℃.
Preferably, the filtration in step (2) is diatomite-assisted filtration.
Preferably, the stirring time at room temperature in the step (4) is 5-10 hours.
Compared with the prior art, the invention has the advantages that:
(1) the synthesis method of the metal catalyst has the advantages of easily obtained reaction raw materials, simple operation of the reaction process, low requirement on reaction equipment, relatively mild reaction conditions, high yield and high content, and is suitable for industrial production, and the content of the finally obtained metal catalyst is more than 99%.
(2) Compared with the defect of low purity of a product obtained by filtering and concentrating the same solvent in the post-treatment in the prior art, the synthesis method of the invention cools and filters the reaction solution, washes a filter cake by using a first organic solvent, combines filtrates, reduces the pressure of the combined filtrates, adds a mixed solvent of a second organic solvent and a third organic solvent with the same volume, re-concentrates the mixed solvent, and adds a mixed solvent of the second organic solvent and the third organic solvent with the same volume of the organic solvents to continuously concentrate the mixed solvent; the first organic solvent is selected from a benign solvent with high solubility, the second organic solvent is a general benign solvent with medium solubility, the third organic solvent is selected from a poor solvent with low solubility, the product is dissolved and concentrated to a smaller volume by utilizing the benign solvent in the post-treatment, the general benign solvent is added to carry the benign solvent out of the system through distillation, the poor solvent is added to separate out the product, and the product and the impurities are separated out to the maximum extent by utilizing the difference of distribution coefficients of the product and the impurities in the mixture in the two solvents, so that the post-treatment yield is increased, and the product purity is improved.
Drawings
FIG. 1 shows [ (S) -BINAP RuCl ] of the present invention2 (p-cymene]/[ (S) - (-) -2,2 '-bis (diphenylphosphino) -1, 1' -binaphthyl]Process scheme for (p-cymene) ruthenium dichloride.
Detailed Description
The invention is described in further detail below with reference to the accompanying examples.
As shown in FIG. 1, a process flow diagram of [ (S) -BINAP RuCl2(p-cymene ]/[ (S) - (-) -2,2 '-bis (diphenylphosphino) -1, 1' -binaphthyl ] (p-cymene) ruthenium dichloride according to the present invention.
Example 1
Under room temperature and nitrogen, 12Kg of isopropylphenyl ruthenium dichloride, 26Kg of (S) -BINAP and 120Kg of tetrahydrofuran, a first organic solvent, are sequentially added into a reaction device which is provided with a thermometer, a reflux condenser and a stirrer, and the system is replaced by nitrogen for three times; stirring, heating to 64 ℃ for refluxing, carrying out heat preservation and reflux reaction for 5 hours, cooling the reaction to 23-25 ℃, filtering under the assistance of diatomite, washing a filter cake by using first organic solvent tetrahydrofuran, combining filtrate, concentrating the filtrate under reduced pressure to 1/2 volume of the total volume of the filtrate, adding equal volume of second organic solvent (ethyl acetate)/third organic solvent (petroleum ether) (1:1, v/v) mixed solvent to concentrate to 1/2 volume, adding equal volume of second organic solvent (ethyl acetate)/third organic solvent (petroleum ether) (1:1, v/v) mixed solvent, continuously concentrating to 4/5 volume of the total volume of the filtrate, cooling to room temperature, stirring for 8 hours at room temperature, filtering, adding second organic solvent (ethyl acetate)/third organic solvent (petroleum ether) (1:1, v/v) washing the mixed solvent to obtain a light yellow crystalline solid, and drying in vacuum to obtain light yellow crystalline solid powder.
The content of [ (S) - (-) -2,2 '-bis (diphenylphosphino) -1, 1' -binaphthyl ] (p-cymene) ruthenium dichloride in the final product is 99.2%, and the molar yield of the product is 90.65%.
Example 2
Adding 19Kg of isopropylphenyl ruthenium dichloride, 45Kg of (S) -BINAP and 190Kg of first organic solvent methanol into a reaction device provided with a thermometer, a reflux condenser and a stirrer in sequence at room temperature and under nitrogen, replacing the system with nitrogen for three times, starting stirring, heating to 65 ℃ for refluxing, preserving heat for refluxing reaction for 5 hours, cooling the reaction to 23-25 ℃, filtering under the assistance of kieselguhr, washing filter cakes with the first organic solvent, combining filtrate, concentrating the filtrate under reduced pressure to 1/2 volume of the total volume of the filtrate, adding a second organic solvent (ethyl acetate)/third organic solvent (n-heptane) (1:1, v/v) mixed solvent with the same volume to 1/2 volume, adding a second organic solvent (ethyl acetate)/third organic solvent (n-heptane) (1:1, v/v) mixed solvent, continuously concentrating to total volume of 4/5 of filtrate, cooling to room temperature, stirring for 10 hours at room temperature, filtering, washing with a mixed solvent of a second organic solvent (ethyl acetate)/a third organic solvent (n-heptane) (1:1, v/v) to obtain a light yellow crystalline solid, and drying in vacuum to obtain light yellow crystalline solid powder.
The content of [ (S) - (-) -2,2 '-bis (diphenylphosphino) -1, 1' -binaphthyl ] (p-cymene) ruthenium dichloride in the final product is 99.3%, and the molar yield of the product is 92.82%.
In addition to the above embodiments, the present invention also includes other embodiments, and any technical solutions formed by equivalent transformation or equivalent replacement should fall within the scope of the claims of the present invention.
Claims (8)
1. A synthesis method of a metal catalyst is characterized by comprising the following steps: the metal catalyst is [ (S) -BINAP RuCl2 (p-cymene]/[ (S) - (-) -2,2 '-bis (diphenylphosphino) -1, 1' -binaphthyl]The synthesis method of (p-cymene) ruthenium dichloride takes isopropylphenyl ruthenium dichloride as a starting material and prepares a catalyst product through ligand exchange reaction, and comprises the following steps:
(1) under the condition of nitrogen, sequentially adding isopropylphenyl ruthenium dichloride, (S) -BINAP and a first organic solvent, heating to reflux, carrying out heat preservation and reflux reaction, and cooling reaction liquid after the reaction;
(2) filtering the reaction solution cooled in the step (1), washing a filter cake with a first organic solvent, and combining filtrates;
(3) concentrating the combined filtrate obtained in the step (2) under reduced pressure to obtain a first concentrated solution, adding a mixed solvent of a second organic solvent and a third organic solvent with the same volume, concentrating again to obtain a second concentrated solution, adding a mixed solvent of the second organic solvent and the third organic solvent with the same volume, and continuously concentrating to obtain a third concentrated solution;
(4) cooling the third concentrated solution obtained in the step (3) to room temperature, stirring at room temperature, filtering, washing with a mixed solvent of a second organic solvent and a third organic solvent to obtain a crude metal catalyst product, and drying in vacuum to obtain a finished metal catalyst product;
wherein the first organic solvent is one of methanol, ethanol, isopropanol, tetrahydrofuran and 2-methyltetrahydrofuran;
the second organic solvent is one of ethyl acetate, isopropyl ether, diethyl ether, isopropyl acetate, n-propyl acetate, butyl acetate and 1, 4-dioxane;
the third organic solvent is one of n-heptane, n-hexane, cyclohexane and petroleum ether.
2. The method for synthesizing a metal catalyst according to claim 1, wherein: the volume ratio of the second organic solvent to the third organic solvent in the mixed solvent is 1: 1.
3. The method for synthesizing a metal catalyst according to claim 1, wherein: the molar ratio of the isopropylphenyl ruthenium dichloride and the (S) -BINAP in the step (1) is 1: 2 to 2.9.
4. The method for synthesizing a metal catalyst according to claim 1, wherein: and (2) keeping the temperature and refluxing for 2-5 hours.
5. The method for synthesizing a metal catalyst according to claim 1, wherein: and (2) cooling the reaction liquid to 20 +/-5 ℃ in the step (1).
6. The method for synthesizing a metal catalyst according to claim 1, wherein: in the step (2), the filtration is diatomite filtration-assisted filtration.
7. The method for synthesizing a metal catalyst according to claim 1, wherein: the step (3) is specifically as follows: and (3) combining the filtrates in the step (2), concentrating the filtrates under reduced pressure to 1/5-1/2 volume of the total volume of the filtrates to obtain a first concentrated solution, adding a mixed solvent of a second organic solvent and a third organic solvent with the same volume, concentrating the mixture to 1/5-1/2 volume to obtain a second concentrated solution, adding a mixed solvent of the second organic solvent and the third organic solvent with the same volume, and continuously concentrating the mixture to 1/2-4/5 volume of the total volume of the filtrates to obtain a third concentrated solution.
8. The method for synthesizing a metal catalyst according to claim 1, wherein: and (4) stirring at room temperature for 5-10 hours.
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| CN114437141A (en) * | 2022-02-15 | 2022-05-06 | 浙江微通催化新材料有限公司 | Preparation method of chiral diphenyl ethylene diamine ruthenium complex |
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| TILMANN J. GELDBACH等: "Chemistry of Ruthenium(II) Alkyl Binap Complexes: Novel Bonding, Cyclometalation, and P-C Bond Splitting", 《ORGANOMETALLICS》, vol. 22, pages 1443 - 1451 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114437141A (en) * | 2022-02-15 | 2022-05-06 | 浙江微通催化新材料有限公司 | Preparation method of chiral diphenyl ethylene diamine ruthenium complex |
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|---|---|
| CN114029092B (en) | 2024-03-05 |
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