IP Library Patent Application 15310760
Patent Application
App. No. 15/310,760

CATALYSTS AND METHODS FOR MAKING CYCLIC CARBONATES

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Quick Facts
Patent No.
US None
App. No.
15/310,760
Abstract

Catalysts and methods for making cyclic carbonates are disclosed. The catalyst may include at least one polymer quaternary ammonium salt, at least one metal halide and silica gel. The method of making the cyclic carbonates may include forming a mixture that includes the catalyst and an epoxide, and contacting the mixture with carbon dioxide in a reactor under conditions to form the propylene carbonate.

Claims (104)

1 . A catalyst comprising:

at least one polymer quaternary ammonium salt;

at least one metal halide; and

silica gel.

2 . The catalyst of claim 1 , wherein:

the at least one polymer quaternary ammonium salt is polydimethyl diallyl ammonium bromide, polydimethyl diallyl ammonium chloride or combination thereof; or the at least one metal halide is ZnBr 2 , ZnCl 2 , FeCl 3 , AlCl 3 , NaCl, CaCl 2 , Zn(OAc) 2 , LiBr or a combination thereof.

3 . (canceled)

4 . (canceled)

5 . The catalyst of claim 1 , wherein:

a mass ratio of the metal halide to a total mass comprising the polymer quaternary ammonium salt, the metal halide, and the silica gel, is about 1:200 to about 1:100;

a molar ratio of the polymer quarternary ammonium salt to the metal halide is about 2:1; or

a mass ratio of the polymer quarternary ammonium salt to the silica gel is about 1:20 to about 1:5.

6 . (canceled)

7 . (canceled)

8 . A method of making a catalyst, the method comprising:

incubating a first mixture comprising at least one polymer quaternary ammonium salt, at least one metal halide and a solvent;

adding silica gel to the first mixture to form a second mixture;

incubating the second mixture; and

removing the solvent from the second mixture to obtain the catalyst.

9 . (canceled)

10 . The method of claim 8 , further comprising grinding the catalyst to obtain a powdered form of the catalyst.

11 . (canceled)

12 . (canceled)

13 . (canceled)

14 . The method of claim 8 , further comprising mixing an organic solvent with water to form the solvent before incubating the first mixture.

15 . (canceled)

16 . (canceled)

17 . (canceled)

18 . The method of claim 8 , wherein the at least one polymer quaternary ammonium salt is present in the first mixture at a concentration of at least about 0.01 g/ml or equal to or less than about 0.05 g/ml.

19 . (canceled)

20 . (canceled)

21 . The method of claim 8 , wherein the polymer quaternary ammonium salt is polydimethyl diallyl ammonium chloride, polydimethyl diallyl ammonium bromide, or a combination thereof.

22 . (canceled)

23 . The method of claim 8 , wherein the metal halide is present in the first mixture at a concentration of at least about 0.010 g/ml or less than or equal to about 0.025 g/ml.

24 . (canceled)

25 . (canceled)

26 . The method of claim 8 , wherein the metal halide is ZnBr 2 , ZnCl 2 , FeCl 3 , AlCl 3 , NaCl, CaCl 2 , Zn(OAc) 2 LiBr, or any combination thereof.

27 . (canceled)

28 . (canceled)

29 . (canceled)

30 . The method of claim 8 , wherein polymer quaternary ammonium salt and the metal halide are present in the first mixture at a molar ratio of at least about 1:4 or less than or equal to about 4:1.

31 . (canceled)

32 . (canceled)

33 . The method of claim 8 , wherein the silica gel is present in the second mixture at a concentration of at least about 0.05 g/ml or less than or equal to about 0.25 g/ml.

34 . (canceled)

35 . (canceled)

36 . (canceled)

37 . (canceled)

38 . (canceled)

39 . (canceled)

40 . (canceled)

41 . (canceled)

42 . The method of claim 8 , wherein removing the solvent from the second mixture comprises aspirating the second mixture.

43 . (canceled)

44 . (canceled)

45 . A method of making cyclic carbonate, the method comprising:

providing a catalyst, comprising:

at least one polymer quaternary ammonium salt;

at least one metal halide; and

silica gel;

forming a mixture comprising the catalyst and an epoxide; and

contacting the mixture with carbon dioxide in a reactor under conditions to form the cyclic carbonate.

46 . (canceled)

47 . The method of claim 45 , wherein the reactor has a non-stick lining on at least an inner surface of the reactor.

48 . (canceled)

49 . (canceled)

50 . The method of claim 45 , wherein reactor is a pressure reactor.

51 . (canceled)

52 . (canceled)

53 . (canceled)

54 . (canceled)

55 . The method of claim 45 , wherein the catalyst is present in the mixture at an amount of at least about 5% by weight or less than or equal to about 20% by weight.

56 . (canceled)

57 . The method of claim 45 , wherein the epoxide is present in the mixture at an amount of at least about 85% by weight or equal to or less than about 95% by weight.

58 . (canceled)

59 . (canceled)

60 . (canceled)

61 . The method of claim 45 , further comprising adding carbon dioxide into the reactor to displace air in the reactor before the contacting step.

62 . (canceled)

63 . (canceled)

64 . (canceled)

65 . The method of claim 45 , wherein the carbon dioxide in the contacting step is added by a carbon dioxide high pressure pump.

66 . The method of claim 45 , wherein the contacting step comprises heating to a temperature of at least about 70° C. or equal to or less than about 150° C.

67 . (canceled)

68 . (canceled)

69 . (canceled)

70 . (canceled)

71 . The method of claim 45 , further comprising removing unreacted carbon dioxide after the contacting step.

72 . (canceled)

73 . (canceled)

74 . (canceled)

75 . The method of claim 45 , further comprising separating the cyclic carbonate from the mixture after the contacting step.

76 . The method of claim 75 , wherein separating the cyclic carbonate from the mixture comprises adding an extraction solvent to dissolve the epoxide and thus separate the cyclic carbonate from the mixture.

77 . (canceled)

78 . The method of claim 76 , further comprising recovering the catalyst from the mixture.

79 . The method of claim 78 , wherein the recovering step comprises subjecting the mixture to at least one of ultrasonic cleaning and centrifuging to separate unreacted epoxide from the catalyst.

80 . The method of claim 78 , further comprising washing the catalyst with a washing solvent.

81 . (canceled)

82 . The method of claim 80 , further comprising drying the catalyst.

83 . (canceled)

84 . (canceled)

85 . (canceled)

86 . (canceled)

87 . (canceled)

Assignments (3)
RELEASE OF SECURITY INTEREST Recorded Jul 31, 2019
From: CRESTLINE DIRECT FINANCE, L.P.
To: EMPIRE TECHNOLOGY DEVELOPMENT LLC
Reel/Frame 049924/0794 →
SECURITY INTEREST Recorded Jan 29, 2019
From: EMPIRE TECHNOLOGY DEVELOPMENT LLC
To: CRESTLINE DIRECT FINANCE, L.P.
Reel/Frame 048373/0217 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 1, 2016
From: HOU, ZHENSHAN; SONG, BAONING
To: EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY
Reel/Frame 040488/0300 →