CN102794199A - Preparation method of phosphine ligand palladium catalyst - Google Patents
Preparation method of phosphine ligand palladium catalyst Download PDFInfo
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- CN102794199A CN102794199A CN2012102794213A CN201210279421A CN102794199A CN 102794199 A CN102794199 A CN 102794199A CN 2012102794213 A CN2012102794213 A CN 2012102794213A CN 201210279421 A CN201210279421 A CN 201210279421A CN 102794199 A CN102794199 A CN 102794199A
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Abstract
The invention discloses a preparation method of a phosphine ligand palladium catalyst, comprising the following steps: (a) adding palladium chloride in hydrochloric acid, heating up to 40-80 DEG C to dissolve, and adding ethanol to dilute, wherein the amount of hydrochloric acid is 0.2-1.0 times of weight of palladium chloride, and the amount of ethanol is 10-50 times of weight of palladium chloride; (b) adding a phosphine ligand in chloroform, heating up to 40-80 DEG C to dissolve, wherein the amount of the phosphine ligand is 1-1.5 times of molar mass of palladium chloride, and the amount of chloroform is 10-20 times of molar weight of palladium chloride; and (c) adding the solution obtained in the step (a) dropwisely in the solution obtained in the step (b), then preserving the heat at 45-80 DEG C for 0.5-3h, then cooling, filtering, washing , and conducting vacuum drying to obtain the palladium coupling catalyst. According to the invention, the reaction becomes easy, the reaction time is shortened, the yield is raised, and the advantages of simple steps, high efficiency, and low product cost, etc. are achieved.
Description
Technical field
The invention belongs to the preparation method of the synthetic field of organic chemical industry, medication chemistry and liquid crystal material, be specifically related to a kind of preparation method of phosphine part palladium catalyst with the palladium coupling catalyst.
Background technology
The alkyl biphosphine ligand is widely used in the synthetic field of organic chemical industry, medication chemistry and liquid crystal material as catalyst.At present, its main synthetic method is palladium bichloride and acetonitrile (benzonitrile) complex compound and phosphine ligand exchange method.Acetonitrile that the method is used and benzonitrile all are great toxicity chemicals, and this method reaction time is long, and efficient is low.
Summary of the invention
The object of the invention is exactly to provide a kind of consuming time shorter for the defective that overcomes above-mentioned prior art existence, and is simple to operate, the preparation method of lower-cost phosphine part palladium catalyst.
The technical scheme that the present invention takes: a kind of preparation method of phosphine part palladium catalyst comprises the steps:
(a) join palladium bichloride in the hydrochloric acid, be heated to 40-80 ℃ of dissolving, the hydrochloric acid consumption is 0.2-1.0 a times of palladium bichloride weight, adds the ethanol dilution, and amount of ethanol is 10-50 a times of palladium bichloride weight;
(b) the phosphine part with 2-2.5 times of palladium bichloride molal weight joins in the chloroform, is heated to 40-80 ℃ of dissolving, and the chloroform consumption is 10-20 a times of palladium bichloride molal weight;
(c) drips of solution that step (a) is obtained is added in the solution that step (b) obtains, and dropwises the back at 45-80 ℃ of insulation 0.5-3h, and cooling is then filtered, washing, and vacuum drying obtains the palladium coupling catalyst.
Concentration of hydrochloric acid is 12N in the said step (a); The purity of ethanol is 50%-100%.
Phosphine part general formula is Ph in the said step (b)
2P (CH
2)
nPPh
2(n is a positive integer).
The vacuum drying temperature is 40-60 ℃ in the said step (c), vacuum 0.04-0.06MPa, and be 6-8h drying time.
The present invention adds the ethanol dilution through commercially available palladium bichloride is dissolved in hydrochloric acid, joins then in the chloroform of phosphine part, and insulation, cooling is filtered, washing, drying obtains phosphine part palladium catalyst.Advantages such as compared with prior art, the invention enables reaction to carry out more easily, and shortened the reaction time, improved yield, it is simple to have step, and efficient is high, and product cost is low.
The specific embodiment
Below in conjunction with specific embodiment the present invention is elaborated.
Embodiment 1:
(a) 177 gram palladium bichlorides are joined in the 100mL hydrochloric acid, be heated to 50 ℃ of dissolvings, add the dilution of 5L ethanol then; Said concentration of hydrochloric acid is 12N, and the purity of said ethanol is 95%;
(b) with 420 grams 1, two (diphenylphosphine) ethane of 2-join in the 2L chloroform (chloroform), are heated to 50 ℃ of dissolvings;
(c) drips of solution that step (a) is obtained is added in the solution that step (b) obtains, and dropwises the back at 50 ℃ of insulation 2.5h, filters after being cooled to room temperature then, obtains yellowish toner art; Wash respectively 2 times with toluene and ether, vacuum drying removes to desolvate and is product again, and yield is about 95%.50 ℃ of vacuum drying temperature, vacuum 0.05MPa, be 7h drying time.
Embodiment 2:
(a) 177 gram palladium bichlorides are joined in the 160mL hydrochloric acid, be heated to 60 ℃ of dissolvings, add the dilution of 7L ethanol then; Said concentration of hydrochloric acid is 12N, and the purity of said ethanol is 85%;
(b) with 434 grams 1, two (diphenylphosphine) propane of 2-join in the 2.5L chloroform (chloroform), are heated to 65 ℃ of dissolvings;
(c) drips of solution that step (a) is obtained is added in the solution that step (b) obtains, and dropwises the back at 60 ℃ of insulation 1h, filters after being cooled to room temperature then, obtains pale yellow powder; Wash respectively 2 times with toluene and ether, vacuum drying removes to desolvate and is product again, and yield is about 93%.55 ℃ of vacuum drying temperature, vacuum 0.06MPa, be 6h drying time.
Embodiment 3:
(a) 177 gram palladium bichlorides are joined in the 130mL hydrochloric acid, be heated to 75 ℃ of dissolvings, add the dilution of 8L ethanol then; Said concentration of hydrochloric acid is 12N, and the purity of said ethanol is 65%;
(b) with 430 grams 1, two (diphenylphosphine) butane of 2-join in the 3L chloroform (chloroform), are heated to 75 ℃ of dissolvings;
(c) drips of solution that step (a) is obtained is added in the solution that step (b) obtains, and dropwises the back at 75 ℃ of insulation 0.5h, filters after being cooled to room temperature then, obtains pale yellow powder; Wash respectively 2 times with toluene and ether, vacuum drying removes to desolvate and is product again, and yield is about 94.2%.60 ℃ of vacuum drying temperature, vacuum 0.05MPa, be 6.5h drying time.
Claims (4)
1. the preparation method of a phosphine part palladium catalyst is characterized in that said method comprises the steps:
(a) join palladium bichloride in the hydrochloric acid, be heated to 40-80 ℃ of dissolving, the hydrochloric acid consumption is 0.2-1.0 a times of palladium bichloride weight, adds the ethanol dilution, and amount of ethanol is 10-50 a times of palladium bichloride weight;
(b) the phosphine part with 2-2.5 times of palladium bichloride molal weight joins in the chloroform, is heated to 40-80 ℃ of dissolving, and the chloroform consumption is 10-20 a times of palladium bichloride molal weight;
(c) drips of solution that step (a) is obtained is added in the solution that step (b) obtains, and dropwises the back at 45-80 ℃ of insulation 0.5-3h, and cooling is then filtered, washing, and vacuum drying obtains the palladium coupling catalyst.
2. according to the described method of claim 1, it is characterized in that: concentration of hydrochloric acid is 12N in the said step (a); The purity of ethanol is 50%-100%.
3. according to the described method of claim 1, it is characterized in that: phosphine part general formula is Ph in the said step (b)
2P (CH
2)
nPPh
2(n is a positive integer).
4. according to the described method of claim 1, it is characterized in that: the vacuum drying temperature is 40-60 ℃ in the said step (c), vacuum 0.04-0.06MPa, and be 6-8h drying time.
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| CN2012102794213A CN102794199A (en) | 2012-08-08 | 2012-08-08 | Preparation method of phosphine ligand palladium catalyst |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108997419A (en) * | 2018-08-29 | 2018-12-14 | 锁浩 | A method of palladium (0) or platinum (0) complex chemical compound are prepared using triphenylphosphine |
| CN110330528A (en) * | 2019-07-08 | 2019-10-15 | 西安凯立新材料股份有限公司 | A kind of preparation method of bis- (triphenylphosphine) palladium bromides |
| CN111039989A (en) * | 2019-12-16 | 2020-04-21 | 西安凯立新材料股份有限公司 | Preparation method of bis (diphenylphosphino) -palladium dichloride chiral catalyst |
Citations (1)
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|---|---|---|---|---|
| WO2007029031A1 (en) * | 2005-09-05 | 2007-03-15 | Johnson Matthey Plc | Metal compound and preparation method therefor |
-
2012
- 2012-08-08 CN CN2012102794213A patent/CN102794199A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007029031A1 (en) * | 2005-09-05 | 2007-03-15 | Johnson Matthey Plc | Metal compound and preparation method therefor |
Non-Patent Citations (4)
| Title |
|---|
| 《Dalton Trans.》 20030925 Paul-Gerhard Lassahn et al Dihalogeno(diphosphane) metal(II) complexes (metal=Co, Ni, Pd) as pre-catalysts for the vinyl/addition polymerization of norbornene-elucidation of the activation process with B(C6F5)3/AlEt3 or Ag[closo-1-CB11H12] and evidence for the in situ formation... 第4437-4450页 1-4 , * |
| PAUL-GERHARD LASSAHN ET AL: "Dihalogeno(diphosphane) metal(II) complexes (metal=Co, Ni, Pd) as pre-catalysts for the vinyl/addition polymerization of norbornene–elucidation of the activation process with B(C6F5)3/AlEt3 or Ag[closo-1-CB11H12] and evidence for the in situ formation...", 《DALTON TRANS.》 * |
| 郭利兵等: "1，2-双（二苯基膦）乙烷氯化钯配合物的合成与表征", 《河南科学》 * |
| 韦凤萍等: "Pd(OAc)2与有机双膦在氯代烷中的反应机理(II)研究", 《波谱学杂志》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108997419A (en) * | 2018-08-29 | 2018-12-14 | 锁浩 | A method of palladium (0) or platinum (0) complex chemical compound are prepared using triphenylphosphine |
| CN110330528A (en) * | 2019-07-08 | 2019-10-15 | 西安凯立新材料股份有限公司 | A kind of preparation method of bis- (triphenylphosphine) palladium bromides |
| CN111039989A (en) * | 2019-12-16 | 2020-04-21 | 西安凯立新材料股份有限公司 | Preparation method of bis (diphenylphosphino) -palladium dichloride chiral catalyst |
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Application publication date: 20121128 |