Table 2 Control experiments for the ROCOP of SO and PAa

From: Acid-base pair-mediated copolymerization of acid-sensitive epoxides and cyclic anhydride for synthesizing recyclable thermoplastics

Entry

Acid/base

Acid:base:PA:SO

T (°C)

t (h)

Conv. (%)b

Mn, SEC (kDa)f

Ðe

Aldehyde (%)f

Ketone (%)f

Ester (%)b

1

–

0:0:0:400

80

24

–c

–

–

n.d.

n.d.

–

2

–

0:0:200:400

80

24

54d

3.5

1.30

4.7

n.d.

70

3

Phthalic acid

2:0:200:400

80

24

88d

2.7

1.27

7.1

n.d.

75

4

Phthalic acid

2:0:0:400

80

24

4c

–

–

0.2

n.d.

–

5

Monomethyl phthalate

2:0:0:400

80

24

2c

–

–

0.2

n.d.

–

6

tBu-P1'

0:2:200:400

80

24

71d

13.0

1.66

0.3

n.d.

>99

7

tBu-P1'

0:2:0:400

80

24

–c

–

–

n.d.

n.d.

–

8

Phthalic acid/tBu-P1'

2:4:0:400

80

24

<1c

–

–

n.d.

n.d.

–

9

TEB

2:0:0:400

80

24

<1c

–

–

0.1

n.d.

–

10

TEB/tBu-P1'

2:2:0:400

80

24

<1c

–

–

n.d.

n.d.

–

11

TEB

2:0:200:400

80

24

21d

2.6

1.18

1.8

n.d.

50

12

tBu-P2

0:2:0:400

80

24

96c

8.5

1.32

n.d.

<0.1

–

13

tBu-P2

0:2:0:400

100

24

>99c

5.4

1.35

n.d.

0.2

–

  1. aThe polymerizations were performed in neat epoxide.
  2. bConv. (%) is the conversion, and ester (%) is the percentage of ester linkage in the polymer, which were both determined from the 1H NMR spectra of sampled mixtures in CDCl3.
  3. cConv. (%) is the conversion of SO.
  4. dConv. (%) is the conversion of PA.
  5. eDetermined by size exclusion chromatography (SEC) in dichloromethane against PS standards.
  6. fAldehyde (%) is the yield of phenylacetaldehyde for SO, and ketone (%) is the yield of acetophenone for SO, which were both determined from the 1H NMR spectra of sampled mixtures in CDCl3.
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