CN117623908A - Method for preparing palladium trifluoroacetate - Google Patents
Method for preparing palladium trifluoroacetate Download PDFInfo
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- CN117623908A CN117623908A CN202311610416.0A CN202311610416A CN117623908A CN 117623908 A CN117623908 A CN 117623908A CN 202311610416 A CN202311610416 A CN 202311610416A CN 117623908 A CN117623908 A CN 117623908A
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- palladium
- trifluoroacetate
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- PBDBXAQKXCXZCJ-UHFFFAOYSA-L palladium(2+);2,2,2-trifluoroacetate Chemical compound [Pd+2].[O-]C(=O)C(F)(F)F.[O-]C(=O)C(F)(F)F PBDBXAQKXCXZCJ-UHFFFAOYSA-L 0.000 title claims abstract description 38
- 238000000034 method Methods 0.000 title claims abstract description 26
- 239000013078 crystal Substances 0.000 claims abstract description 36
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 31
- 238000003756 stirring Methods 0.000 claims abstract description 23
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 20
- 238000006243 chemical reaction Methods 0.000 claims abstract description 20
- 239000000706 filtrate Substances 0.000 claims abstract description 15
- 238000005406 washing Methods 0.000 claims abstract description 15
- 238000001035 drying Methods 0.000 claims abstract description 13
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229960000583 acetic acid Drugs 0.000 claims abstract description 10
- 239000012362 glacial acetic acid Substances 0.000 claims abstract description 10
- 229910017604 nitric acid Inorganic materials 0.000 claims abstract description 10
- 238000001291 vacuum drying Methods 0.000 claims abstract description 9
- 238000001816 cooling Methods 0.000 claims abstract description 8
- 238000001914 filtration Methods 0.000 claims abstract description 8
- 239000007789 gas Substances 0.000 claims abstract description 8
- 238000010438 heat treatment Methods 0.000 claims abstract description 8
- 239000005457 ice water Substances 0.000 claims abstract description 8
- 239000000203 mixture Substances 0.000 claims abstract description 8
- 239000012299 nitrogen atmosphere Substances 0.000 claims abstract description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims abstract description 7
- 239000000376 reactant Substances 0.000 claims abstract description 3
- 238000004821 distillation Methods 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- UYCAUPASBSROMS-AWQJXPNKSA-M sodium;2,2,2-trifluoroacetate Chemical compound [Na+].[O-][13C](=O)[13C](F)(F)F UYCAUPASBSROMS-AWQJXPNKSA-M 0.000 claims description 5
- CUNPJFGIODEJLQ-UHFFFAOYSA-M potassium;2,2,2-trifluoroacetate Chemical compound [K+].[O-]C(=O)C(F)(F)F CUNPJFGIODEJLQ-UHFFFAOYSA-M 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 abstract description 6
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 239000000047 product Substances 0.000 abstract description 4
- 229910000510 noble metal Inorganic materials 0.000 abstract description 3
- 229910052763 palladium Inorganic materials 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- -1 biaryl compounds Chemical class 0.000 description 3
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000010485 C−C bond formation reaction Methods 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000012824 chemical production Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000006880 cross-coupling reaction Methods 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000009509 drug development Methods 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to the technical field of noble metal catalysts, in particular to a method for preparing palladium trifluoroacetate, which comprises the following steps: s1, taking palladium powder with preset mass, placing the palladium powder into a multifunctional reaction kettle, adding concentrated nitric acid with preset volume under nitrogen atmosphere, and starting stirring; s2, after stirring is completed, setting the temperature to be 60-100 ℃, adding glacial acetic acid with a preset volume after heating, and preserving the temperature for 5-8 hours until no brown gas is generated in the reactant; s3, adding a preset amount of trifluoroacetate into the reaction kettle, and continuously preserving heat for 3-4 hours; s4, cooling to room temperature, filtering, and respectively collecting crystals and filtrate; s5, repeatedly washing the crystals with an ice-water mixture, and concentrating and crystallizing; and S6, placing all the crystals in a vacuum drying oven, and drying to constant weight to obtain the palladium trifluoroacetate. The invention has the advantages of simple production process, high product purity, low production cost and the like, can realize the industrial industrialization of the palladium trifluoroacetate, and greatly improves the economic profit of enterprises.
Description
Technical Field
The invention relates to the technical field of noble metal catalysts, in particular to a method for preparing palladium trifluoroacetate.
Background
Among the numerous transition metal catalysts, metallic palladium is one of the most widely used catalysts at present. Palladium-catalyzed C-C bond formation is an advantageous tool for constructing complex molecules, and especially after the 21 st century, palladium-catalyzed coupling reactions have established a mature, stable system, and have been under much more intense investigation. Compared with the traditional method, the palladium-catalyzed organic reaction has obvious advantages such as mild reaction conditions, simple reaction, high yield and good selectivity. Palladium-catalyzed aryl coupling reactions have been widely studied in both academia and industrial production fields, and provide powerful tools for synthesizing molecules with complex structures and biological activities, whereas biaryl compounds containing heteroaryl groups are common constituent units of natural drugs, so that they occupy very important positions in industries such as drug development, natural product preparation, fine product chemical production and the like.
Palladium trifluoroacetate, also known as palladium trifluoroacetate, is a noble metal palladium catalyst commonly used for mild decarboxylation reaction and direct cross-coupling reaction of unactivated aromatic hydrocarbon, and is also commonly used for catalyzing the oxidation reaction of olefin to generate alpha, beta-unsaturated aldehyde or ketene compound. The main method for preparing the palladium trifluoroacetate in the industry comprises the following steps: palladium acetate was evaporated in trifluoroacetic acid in a steam bath and reacted directly. The palladium acetate used by the method is a common palladium catalyst in the pharmaceutical industry, has high price and is not beneficial to industrialized production. The products prepared by the reaction of palladium hydroxide and trifluoroacetic acid, such as Trost, B.M. and the like, have lower activity, larger loss of palladium and need to be improved.
Disclosure of Invention
Features and advantages of the invention will be set forth in part in the description which follows, or may be obvious from the description, or may be learned by practice of the invention.
In order to overcome the problems in the prior art, the invention provides a method for preparing palladium trifluoroacetate with low palladium loss, and the palladium trifluoroacetate prepared by the method has high yield and good activity.
A method of preparing palladium trifluoroacetate comprising the steps of:
s1, taking palladium powder with preset mass, placing the palladium powder into a multifunctional reaction kettle, adding concentrated nitric acid with preset volume under nitrogen atmosphere, and starting stirring;
s2, after stirring is completed, setting the temperature to be 60-100 ℃, adding glacial acetic acid with a preset volume after heating, and preserving the temperature for 5-8 hours until no brown gas is generated in the reactant;
s3, adding a preset amount of trifluoroacetate solution into the reaction kettle, and continuously preserving heat for 3-4 hours;
s4, cooling to the room temperature of 20-25 ℃, filtering, and respectively collecting crystals and filtrate;
s5, repeatedly washing the crystal for 5-8 times by using an ice-water mixture, combining the washing liquid with the previous filtrate, and concentrating and crystallizing under the condition of reduced pressure distillation to obtain the crystal;
and S6, placing all the crystals in a vacuum drying oven, and drying to constant weight to obtain the palladium trifluoroacetate.
Preferably, the ratio of the mass of palladium powder to the volume of concentrated nitric acid is 1g:10ml.
Preferably, the ratio of the mass of the palladium powder to the volume of glacial acetic acid is 1g to 20-30 ml.
Preferably, the stirring speed is 100-200 r/min.
Preferably, the molar ratio of the palladium powder to the trifluoroacetate solution is 1:3-5, and the trifluoroacetate solution comprises one of sodium trifluoroacetate solution and potassium trifluoroacetate solution.
Preferably, the temperature of the vacuum drying oven is 60-80 ℃.
The invention has the beneficial effects that: the method for preparing the palladium trifluoroacetate provided by the invention can be used for preparing the palladium trifluoroacetate without using palladium acetate as a raw material, and directly adopting palladium powder with relatively lower cost, thereby greatly saving the cost of the raw material in the industrial production process; in addition, the preparation method has lower loss on palladium, and the prepared palladium trifluoroacetate has good activity, less impurities and higher yield. The invention has the advantages of simple production process, high product purity, low production cost and the like, can realize the industrial industrialization of the palladium trifluoroacetate, and greatly improves the economic profit of enterprises.
Drawings
The advantages and the manner of carrying out the invention will become more apparent from the following detailed description, taken in conjunction with the accompanying drawings, in which the content shown is meant to illustrate, but not to limit, the invention in any sense, and wherein:
FIG. 1 is a process flow diagram of a method for preparing palladium trifluoroacetate in accordance with one embodiment of the present invention;
FIG. 2 is a test report of palladium trifluoroacetate prepared by the method of example 1 of the present invention.
Detailed Description
Embodiments of the present invention are described in further detail below with reference to the accompanying drawings and examples. The following examples are illustrative of the invention but are not intended to limit the scope of the invention.
Example 1
As shown in fig. 1, the present invention provides a method for preparing palladium trifluoroacetate, comprising the steps of:
s1, placing 250g of commercial palladium powder into a multifunctional reaction kettle, adding 2.5L of concentrated nitric acid under nitrogen atmosphere, and starting stirring at the stirring speed of 100r/min;
s2, after stirring is completed, setting the temperature to 60 ℃, adding 5.0L of glacial acetic acid after heating is completed, and preserving the temperature for 5 hours until no brown gas is generated;
s3, adding 7.05 mol of sodium trifluoroacetate into the reaction kettle, and continuously preserving heat for 3 hours;
s4, cooling to room temperature of 20 ℃, filtering, and respectively collecting crystals and filtrate;
s5, repeatedly washing the crystal for 5 times by using an ice-water mixture, combining the washing liquid with the previous filtrate, and concentrating and crystallizing under the condition of reduced pressure distillation to obtain the crystal;
s5, placing the crystals in a vacuum drying oven, and drying the crystals to constant weight at the drying temperature of 60 ℃ to obtain 768.43g of palladium trifluoroacetate with the yield of 98.36%. The prepared palladium trifluoroacetate is detected by an ICP spectrometer, and the detection result is shown in figure 2, and shows that the palladium trifluoroacetate prepared by the method has higher purity, lower impurity content, complete reaction of metal palladium and better activity.
Example 2
The invention provides a method for preparing palladium trifluoroacetate, which comprises the following steps:
s1, placing 400g of commercial palladium powder into a multifunctional reaction kettle, adding 4.0L of concentrated nitric acid under a nitrogen atmosphere, and starting stirring at a stirring speed of 150r/min;
s2, after stirring is completed, setting the temperature to 80 ℃, adding 10.0L of glacial acetic acid after heating is completed, and preserving the temperature for 6 hours until no brown gas is generated;
s3, adding 15.03 mol of potassium trifluoroacetate into the reaction kettle, and continuously preserving heat for 3 hours;
s4, cooling to room temperature of 25 ℃, filtering, and respectively collecting crystals and filtrate;
s5, repeatedly washing the crystal for 8 times by using an ice-water mixture, combining the washing liquid with the previous filtrate, and concentrating and crystallizing under the condition of reduced pressure distillation to obtain the crystal;
s5, placing the crystals in a vacuum drying oven, and drying the crystals to constant weight at the drying temperature of 70 ℃ to obtain 1216.87g of palladium trifluoroacetate with the yield of 97.35%.
Example 3
The invention provides a method for preparing palladium trifluoroacetate, which comprises the following steps:
s1, placing 500g of commercial palladium powder into a multifunctional reaction kettle, adding 5L of concentrated nitric acid under a nitrogen atmosphere, and starting stirring at a stirring speed of 200r/min;
s2, after stirring is completed, setting the temperature to 70 ℃, adding 15L of glacial acetic acid after heating is completed, and preserving the temperature for 8 hours until no brown gas is generated;
s3, adding 23.49 mol of sodium trifluoroacetate into the reaction kettle, and continuously preserving the heat for 3.5 hours;
s4, cooling to the room temperature of 23 ℃, filtering, and respectively collecting crystals and filtrate;
s5, repeatedly washing the crystal for 6 times by using an ice-water mixture, combining the washing liquid with the previous filtrate, and concentrating and crystallizing under the condition of reduced pressure distillation to obtain the crystal;
s5, placing the crystals in a vacuum drying oven, and drying the crystals to constant weight at the drying temperature of 80 ℃ to obtain 1524.21g of palladium trifluoroacetate with the yield of 97.55%.
Example 4
The invention provides a method for preparing palladium trifluoroacetate, which comprises the following steps:
s1, placing 350g of commercial palladium powder into a multifunctional reaction kettle, adding 3.5L of concentrated nitric acid under a nitrogen atmosphere, and starting stirring at a stirring speed of 100r/min;
s2, after stirring is completed, setting the temperature to 60 ℃, adding 7.7L of glacial acetic acid after heating is completed, and preserving the temperature for 5 hours until no brown gas is generated;
s3, adding 14.8 mol of sodium trifluoroacetate into the reaction kettle, and continuously preserving heat for 3 hours;
s4, cooling to room temperature of 20 ℃, filtering, and respectively collecting crystals and filtrate;
s5, repeatedly washing the crystal for 5 times by using an ice-water mixture, combining the washing liquid with the previous filtrate, and concentrating and crystallizing under the condition of reduced pressure distillation to obtain the crystal;
s5, placing the crystals in a vacuum drying oven, and drying the crystals to constant weight at the drying temperature of 60 ℃ to obtain 1073.41g of palladium trifluoroacetate with the yield of 98.14%.
Example 5
The invention provides a method for preparing palladium trifluoroacetate, which comprises the following steps:
s1, placing 600g of commercial palladium powder into a multifunctional reaction kettle, adding 6L of concentrated nitric acid under a nitrogen atmosphere, and starting stirring at a stirring speed of 150r/min;
s2, after stirring is completed, setting the temperature to 80 ℃, adding 16.8L of glacial acetic acid after heating is completed, and preserving the temperature for 6 hours until no brown gas is generated;
s3, adding 19.73 mol of potassium trifluoroacetate into the reaction kettle, and continuously preserving heat for 3 hours;
s4, cooling to room temperature of 25 ℃, filtering, and respectively collecting crystals and filtrate;
s5, repeatedly washing the crystal for 8 times by using an ice-water mixture, combining the washing liquid with the previous filtrate, and concentrating and crystallizing under the condition of reduced pressure distillation to obtain the crystal;
s5, placing the crystals in a vacuum drying oven, and drying the crystals to constant weight at the drying temperature of 70 ℃ to obtain 1845.56g of palladium trifluoroacetate with the yield of 98.43%.
While the preferred embodiments of the present invention have been illustrated by reference to the accompanying drawings, those skilled in the art will appreciate that many modifications are possible in carrying out the invention without departing from the scope and spirit thereof. For example, features illustrated or described as part of one embodiment can be used on another embodiment to yield still a further embodiment. The foregoing description and drawings are merely illustrative of preferred embodiments of the present invention and are not intended to limit the scope of the claims, but rather to cover all modifications within the scope of the present invention.
Claims (6)
1. A method for preparing palladium trifluoroacetate comprising the steps of:
s1, taking palladium powder with preset mass, placing the palladium powder into a multifunctional reaction kettle, adding concentrated nitric acid with preset volume under nitrogen atmosphere, and starting stirring;
s2, after stirring is completed, setting the temperature to be 60-100 ℃, adding glacial acetic acid with a preset volume after heating, and preserving the temperature for 5-8 hours until no brown gas is generated in the reactant;
s3, adding a preset amount of trifluoroacetate solution into the reaction kettle, and continuously preserving heat for 3-4 hours;
s4, cooling to the room temperature of 20-25 ℃, filtering, and respectively collecting crystals and filtrate;
s5, repeatedly washing the crystal for 5-8 times by using an ice-water mixture, combining the washing liquid with the previous filtrate, and concentrating and crystallizing under the condition of reduced pressure distillation to obtain the crystal;
and S6, placing all the crystals in a vacuum drying oven, and drying to constant weight to obtain the palladium trifluoroacetate.
2. A method for preparing palladium trifluoroacetate according to claim 1 wherein the ratio of palladium powder mass to concentrated nitric acid volume is 1g:10ml.
3. The method for preparing palladium trifluoroacetate according to claim 1, wherein the ratio of the mass of palladium powder to the volume of glacial acetic acid is 1 g:20-30 ml.
4. The method for preparing palladium trifluoroacetate according to claim 1 wherein the stirring speed is 100-200 r/min.
5. The method for preparing palladium trifluoroacetate according to claim 1 wherein the molar ratio of palladium powder to trifluoroacetate solution is 1:3-5; the trifluoroacetate solution comprises one of a sodium trifluoroacetate solution and a potassium trifluoroacetate solution.
6. The method for preparing palladium trifluoroacetate according to claim 1, wherein the temperature of the vacuum oven is 60-80 ℃.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202311610416.0A CN117623908A (en) | 2023-11-28 | 2023-11-28 | Method for preparing palladium trifluoroacetate |
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| Application Number | Priority Date | Filing Date | Title |
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| CN202311610416.0A CN117623908A (en) | 2023-11-28 | 2023-11-28 | Method for preparing palladium trifluoroacetate |
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Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4465635A (en) * | 1982-11-22 | 1984-08-14 | Ashland Oil, Inc. | Manufacture of palladous carboxylates |
| US4760177A (en) * | 1985-10-18 | 1988-07-26 | Rhone Poulenc Specialties Chimiques | Process for preparing alkali metal salts of trifluoroacetic acid in the anhydrous and crystalline state |
| CN102320951A (en) * | 2011-06-13 | 2012-01-18 | 陕西瑞科新材料股份有限公司 | Method for preparing palladium acetate tripolymer |
| RU2529036C1 (en) * | 2013-05-24 | 2014-09-27 | Федеральное Государственное Бюджетное Учреждение Науки Институт Химии И Химической Технологии Сибирского Отделения Российской Академии Наук (Иххт Со Ран) | Method of producing palladium trifluoroacetate |
| RU2536684C1 (en) * | 2013-10-14 | 2014-12-27 | Федеральное Государственное Автономное Образовательное Учреждение Высшего Профессионального Образования "Сибирский Федеральный Университет" | Method of obtaining polymer palladium carboxylates |
| CN106748747A (en) * | 2016-11-18 | 2017-05-31 | 江西省汉氏贵金属有限公司 | The preparation method of palladium trifluoroacetate |
| US20180362436A1 (en) * | 2017-06-14 | 2018-12-20 | Chevron Phillips Chemical Company Lp | Continuous process for the conversion of olefins and carbon dioxide to acrylates via solution phase reactor |
| CN116375575A (en) * | 2023-03-01 | 2023-07-04 | 安徽泽升科技有限公司 | Palladium acetate and preparation method of compound thereof |
-
2023
- 2023-11-28 CN CN202311610416.0A patent/CN117623908A/en active Pending
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4465635A (en) * | 1982-11-22 | 1984-08-14 | Ashland Oil, Inc. | Manufacture of palladous carboxylates |
| US4760177A (en) * | 1985-10-18 | 1988-07-26 | Rhone Poulenc Specialties Chimiques | Process for preparing alkali metal salts of trifluoroacetic acid in the anhydrous and crystalline state |
| CN102320951A (en) * | 2011-06-13 | 2012-01-18 | 陕西瑞科新材料股份有限公司 | Method for preparing palladium acetate tripolymer |
| RU2529036C1 (en) * | 2013-05-24 | 2014-09-27 | Федеральное Государственное Бюджетное Учреждение Науки Институт Химии И Химической Технологии Сибирского Отделения Российской Академии Наук (Иххт Со Ран) | Method of producing palladium trifluoroacetate |
| RU2536684C1 (en) * | 2013-10-14 | 2014-12-27 | Федеральное Государственное Автономное Образовательное Учреждение Высшего Профессионального Образования "Сибирский Федеральный Университет" | Method of obtaining polymer palladium carboxylates |
| CN106748747A (en) * | 2016-11-18 | 2017-05-31 | 江西省汉氏贵金属有限公司 | The preparation method of palladium trifluoroacetate |
| US20180362436A1 (en) * | 2017-06-14 | 2018-12-20 | Chevron Phillips Chemical Company Lp | Continuous process for the conversion of olefins and carbon dioxide to acrylates via solution phase reactor |
| CN116375575A (en) * | 2023-03-01 | 2023-07-04 | 安徽泽升科技有限公司 | Palladium acetate and preparation method of compound thereof |
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| CB03 | Change of inventor or designer information | ||
| CB03 | Change of inventor or designer information |
Inventor after: Zhao Yanjie Inventor after: Zhao Jincheng Inventor after: Liu Luan Inventor after: Zhai Youwen Inventor after: Su Linhui Inventor after: Su Lin Inventor after: Zhou Lanfang Inventor after: Liu Shukun Inventor after: Duan Yonghua Inventor after: Fan Xingxiang Inventor after: Li Yang Inventor after: Li Hongmei Inventor before: Zhao Yanjie Inventor before: Li Hongmei Inventor before: Zhao Jincheng Inventor before: Liu Luan Inventor before: Zhai Youwen Inventor before: Su Linhui Inventor before: Su Lin Inventor before: Zhou Lanfang Inventor before: Liu Shukun Inventor before: Duan Yonghua Inventor before: Wang Kaijun Inventor before: Fan Xingxiang Inventor before: Li Yang |