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Hoh2c CHO



HCOOH

CH2

CH2

CH3

CO2H

O

Condensation products

H O 2

O

CHO

OR

R

OMe

H

+

OR

R

O OMe

OH

OR

OMe

OR

R

OMe

OR

R

MeO

O

H+

-3H2O

H+

-3H2O

+

+ lignin fragments

Pentoses

Hexoses

+

+

47 72

71 73 74

Scheme 4.49 Degradation of pentoses and hexoses under

acidic conditions and condensation of degradation products

with lignin units.

R

OH

OH O

HO

HO

CH3

OH

OH

O

O

O

HO

HO

OH

OH

COOH

OH

OH

O

OH

R = H, OH, CH3,

CO2H, or COCH3

R = CH3 or CHO

48 49 50 51

52 53 54

Scheme 4.50 Aromatic compounds formed from dehydration

of sugars under acidic conditions [38,39].

420 4 Chemical Pulping Processes

Reaction of Hexenuronic Acid under Acidic Conditions

Hexenuronic acids are only formed under alkaline pulping conditions (cf. reaction

in kraft pulping). However, in two-stage sulfite processes with a first stage at a

higher pH, their reactions in the subsequent acidic stage must be considered.

According to Teleman et al. [40], hexenuronic acids are degraded under acidic conditions

to 5-formyl furancarbonic acid (61) according to Scheme 4.51.

O OXyl

OH

O

HO

OH

-XylOH

O

OH

O

O

OH

H

OH2

+

O

OH

O O

HO

O

O

O

HO OH

O

H

H

H

O

O

HO O

H

O

H

H

O

O

HO

O

O

HO O

H2-HCO O 2H

-H2O

-H2O

-H2O

55 56

60 59

+

+

Scheme 4.51 Formation of 5-formylfurancarboxylic acid from hexenuronic acid [40].





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