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A kind of thermosensitive ruthenium carbene complex and its preparation method and application

A carbene complex and temperature-sensitive technology, which is applied in the field of ruthenium carbene complex and its preparation, can solve the problems that the catalyst cannot be stored for a long time, affects the final performance of the material, and the temperature-controlled catalyst is slow, so as to catalyze the temperature-controlled polymerization of olefins , broad industrial application prospects, the effect of less catalyst consumption

Active Publication Date: 2021-11-12
SHANGHAI RES INST OF CHEM IND
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

It should be noted that while inhibiting the catalyst activity, the introduction of additives also affects the final performance of the material
The second way is to use a catalyst with low / medium activity. The main disadvantage of this method is that a large amount of catalyst is required, and the cost of polymeric materials is mainly controlled by the amount of catalyst used.
Van der Schaaf et al [J.Organomet.Chem.,2000,606:65-74] prepared a latent catalyst for initiating ring-opening heterotopic polymerization of olefins. Although the initiation temperature was adjusted by changing the substituent of the pyridine ring, the catalyst activity not tall
Then, Ung et al [Organometallics, 2004, 23:5399–5401] adjusted the activity of the catalyst through partial isomerization of the structure, but these catalysts could not be stored in the olefin monomer for a long time, and the polymerization process was completed within 25 minutes
Verpoort et al [J.Mol.Cat.A:Chem.,2006,260:221-226] studied the O,N-bidentate Schiff base combined ruthenium carbene catalyst, which can be stored in olefins for several months, But the activity is relatively poor
From the current point of view, the research progress on temperature-controlled catalysts is relatively slow, and the catalysts can only achieve partial functions. Most of the catalysts either have low activity, complex structures, or have certain corrosion

Method used

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  • A kind of thermosensitive ruthenium carbene complex and its preparation method and application
  • A kind of thermosensitive ruthenium carbene complex and its preparation method and application
  • A kind of thermosensitive ruthenium carbene complex and its preparation method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] This embodiment is a preparation method of a temperature-sensitive ruthenium carbene complex, and its synthetic route is as follows:

[0038]

[0039]The specific preparation process is:

[0040] (1) Get 20.0g Grubbs second-generation catalyst to a 250mL flask, add 100mL pyridine (used as solvent and reactant), stir at room temperature for 24h, then obtain 16.0g Grubbs third-generation catalyst through separation and purification, yield 93%; : The preparation process of Grubbs third-generation catalyst refers to [Organometallics, 2001, 20, 5314-5318] literature.

[0041] The prepared Grubbs third-generation catalyst was characterized by nuclear magnetic resonance, and the detection data were as follows:

[0042] 1 H NMR (CDCl 3 )19.67(s,1H,CH=Ph),8.84(s,2H,pyridine),8.39(s,2H,pyridine),8.07(d,2H,ortho CH),7.15(t,1H,para CH), 6.83-6.04 (m, 9H, pyridine, Mes-CH), 3.37 (d, 4H, CH 2 CH 2 ),2.79(s,6H,Mes-CH 3 ),2.45(s,6H,Mes-CH 3 ),2.04(s,6H,Mes-CH 3 ).

[0043]...

Embodiment 2

[0051] In this implementation, the Grubbs third-generation catalyst obtained in step (1) in Example 1 was used to further prepare a temperature-sensitive ruthenium carbene complex, catalyst Cat.-2; and the prepared catalyst was used to catalyze 2,5-dimethyl- Polymerization of 2,4-hexadiene.

[0052] (1) Mix 1.0g Grubbs third-generation catalyst with 4.86gN(C 8 h 17 ) 3 (10.0 equivalents) was added to 5 mL of ethyl acetate solvent, and magnetically stirred at 40° C. for 12 h; after the reaction was completed, 1.04 g of catalyst Cat.-2 was obtained by separation, purification, and drying, with a catalyst yield of 82%.

[0053] Carry out nuclear magnetic resonance characterization of the catalyst Cat.-2 prepared, and the detection data are as follows:

[0054] 1 H NMR (CDCl 3 ) δ (ppm) = 0.88 (t, 9H, CH 2 -CH 3 ),1.26(t,36H,-CH 2 -),2.12(s,12H,Mes-CH 3 ),2.26(s,6H,Mes-CH 3 ),2.34(t,6H,N-CH 2 ),4.04(s,4H,N-CH 2 -CH 2 -N), 6.63(s, 4H, Mes-CH), 7.23(t, 2H, Ar-H), 7.54(t...

Embodiment 3

[0060] In this implementation, the third-generation Grubbs catalyst obtained in step (1) of Example 1 was used to further prepare a temperature-sensitive ruthenium carbene complex, catalyst Cat.-3; and the prepared catalyst was used to catalyze the polymerization of dicyclopentadiene.

[0061] (1) 1.0gGrubbs third generation catalyst and 18.95g N(C 16 h 33 ) 3 (20.0 equivalents) was added to 20 mL of ether solvent, and magnetically stirred at 60°C for 48 hours; after the reaction was completed, 1.19 g of catalyst Cat.-3 was obtained by separation, purification, and drying, with a yield of 69%.

[0062] The prepared Cat.-3 catalyst was characterized by nuclear magnetic resonance, and the detection data were as follows:

[0063] 1 H NMR (CDCl 3 ) δ (ppm) = 0.88 (t, 9H, CH 2 -CH 3 ),1.27(t,84H,-CH 2 -),2.12(s,12H,Mes-CH 3 ),2.26(s,6H,Mes-CH 3 ),2.34(t,6H,N-CH 2 ),4.04(s,4H,N-CH 2 -CH 2 -N), 6.63(s, 4H, Mes-CH), 7.23(t, 2H, Ar-H), 7.54(t, 1H, ArH), 7.75(d, 2H, Ar-H), 1...

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Abstract

The invention relates to a temperature-sensitive ruthenium carbene complex and its preparation method and application. The preparation method is to take the Grubbs third-generation catalyst, and combine the Grubbs third-generation catalyst with NR 3 Adding it into a solvent for reaction; separating, purifying, and drying the reacted material to obtain the temperature-sensitive ruthenium carbene complex; the temperature-sensitive ruthenium carbene complex is a catalyst with temperature-sensitive properties, and is used to catalyze the metathesis of olefins Reaction, especially suitable for catalyzing olefin ring-opening heterosituation polymerization. Compared with the prior art, the preparation process of the catalyst of the present invention is simple, and the raw materials are easy to obtain. When used for ring-opening heterotopic polymerization of olefins, the dosage is small, the temperature is controllable, the temperature-controlled polymerization of olefins can be realized, and it has wide industrial applications Prospects etc.

Description

technical field [0001] The invention relates to a class of ruthenium carbene complexes and a preparation method and application thereof, belonging to the technical field of organometallic catalyst preparation, in particular to a temperature-sensitive ruthenium carbene complex and a preparation method and application thereof. Background technique [0002] In recent decades, the research on olefin metathesis reaction and its great value in the fields of medicine and materials have made it develop rapidly. Ring-opening metathesis polymerization (ROMP) reaction is an important reaction type in olefin metathesis reaction. The research in this field mainly focuses on the preparation of specific catalysts suitable for corresponding conditions, and the preparation of of functional materials. After years of development, catalysts suitable for ring-opening heterotopic polymerization have produced dispersions of different structure types, among which the most important and most widely...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/00B01J31/22C08G61/08
CPCB01J31/2278B01J2231/12B01J2231/543B01J2531/0233B01J2531/0238B01J2531/821C07F15/0046C08G61/08C08G2261/418
Inventor 杨维成刘建罗勇段高坤付宏伟乔新峰乔拟春李秀君
Owner SHANGHAI RES INST OF CHEM IND
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