Carbonation Reaction of Epoxidized Linseed Oil: Comparative Performance of TBABr and TBAI as Catalysts

Table 1

Experimental conditions and results.

Experiment

Catalyst

Catalyst load (mol%)

Reaction temperature (°C)

Reaction time (h)

Epoxides^a

Halohydrins^a

Ketones^a

CC5^a

η%

Y%

S%

H%

K%

Yield %

CELO1

TBABr

2.5

110

48

0.0 ± 0.0

0.1 ± 0.1

0.1 ± 0.1

5.1 ± 0.1

100.0 ± 0.0

87.9 ± 2.4

87.9 ± 2.4

1.7 ± 2.4

1.7 ± 2.4

72.0 ± 0.6

CELO2

TBAI

2.5

110

48

0.2 ± 0.1

0.2 ± 0.1

1.4 ± 0.1

3.4 ± 0.1

96.6 ± 2.4

58.6 ± 2.4

60.7 ± 1.0

3.4 ± 2.4

24.1 ± 2.4

71.8 ± 0.7

CELO3

TBAI

5.0

110

24

0.2 ± 0.1

0.1 ± 0.1

1.7 ± 0.1

3.1 ± 0.0

96.6 ± 2.4

53.4 ± 0.0

55.4 ± 1.4

1.7 ± 2.4

29.3 ± 2.4

71.7 ± 1.0

CELO4

TBABr

5.0

110

24

0.0 ± 0.0

0.2 ± 0.1

0.1 ± 0.0

3.7 ± 0.1

100.0 ± 0.0

63.8 ± 2.4

63.8 ± 2.4

3.4 ± 2.4

1.7 ± 0.0

72.0 ± 1.7

CELO5

TBABr

2.5

140

24

2.9 ± 0.1

0.1 ± 0.1

0.2 ± 0.0

1.6 ± 0.1

50.0 ± 2.4

27.6 ± 2.4

55.2 ± 2.2

1.7 ± 2.4

3.4 ± 0.0

71.7 ± 0.3

CELO6

TBAI

2.5

140

24

2.5 ± 0.1

0.2 ± 0.1

0.7 ± 0.1

0.6 ± 0.1

56.9 ± 2.4

10.3 ± 2.4

18.2 ± 3.5

3.4 ± 2.4

12.1 ± 2.4

72.0 ± 1.4

CELO7

TBAI

5.0

140

48

0.3 ± 0.1

0.1 ± 0.1

2.1 ± 0.1

0.2 ± 0.0

94.8 ± 2.4

3.4 ± 0.0

3.6 ± 0.1

1.7 ± 2.4

36.2 ± 2.4

71.9 ± 2.1

CELO8

TBABr

5.0

140

48

0.1 ± 0.1

0.1 ± 0.1

1.9 ± 0.1

1.1 ± 0.1

98.3 ± 2.4

19.0 ± 2.4

19.3 ± 2.0

1.7 ± 2.4

32.8 ± 2.4

71.7 ± 0.7

^a: Number of indicated groups per molecule as obtained from ¹H-NMR results; CC5: 5-membered cyclic carbonates; η%: conversion percentage; Y%: carbonation percentage; S%: selectivity percentage, H%: halohydrination percentage; and K%: ketonation percentage.