the chemistry and technology of furfural and its many by-products

Karl J. Zeitsch (Eds.)044450351X, 9780444503510, 9780080528991

This book is a “world first”, since the furfural industry has been traditionally secretive to the point of appearing shrouded in clouds of mystery. Even renowned encyclopedic works have published but scant and often erroneous information on the subject.Striking a healthy balance between theory and practice, the book leads the reader from reaction mechanisms and kinetics to the technology of making furfural by various old and new processes, using conventional raw materials or sulfite waste liquor. Detailed discussions of means of increasing the yield are of great chemical and technological interest as well as of immense economic importance.From furfural proper, the treatise shifts to the fascinating field of wanted and unwanted by-products ranging from largely unutilized carboxylic acids to troublesome impurities such as 5-methyl furfural and 2-furyl methyl ketone, and then to extremely valuable serendipitous flavor compounds such as diacetyl and 2,3-pentanedione. A wide variety of derivatives are discussed; considerable space is devoted to polytetrahydrofuran, an important building block of stretchable synthetic fibers, while furan resins from both furfural and furfuryl alcohol are given the attention commensurate with their industrial importance.Notable supplementary chapters cover the in-line measurement of furfural, the treatment of furfural waste water, and various aspects of corrosion. A chapter on the applications of furfural elaborates not only traditional uses in extracting petroleum and vegetable oils but also the sensational discovery that furfural is a highly effective “indirect nematocide”. Without becoming toxic, it changes the microflora ofthe soil by stimulating bacteria antagonistic to nematodes, thereby reducing the nematode population to zero, at an unprecedented low price. It is believed that this application will be the principal outlet for furfural in the future.A comprehensive list of physical properties, some never published before, make the book an indispensable companion for producers, users and researchers alike.

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Table of contents :
Content:
1. Introduction
Pages 1-2

2. The reactions leading to furfural Original Research Article
Pages 3-7

3. Acid catalysis Original Research Article
Pages 8-13

4. The kinetics of pentose formation from pentosan Original Research Article
Page 14

5. The kinetics of xylose disappearance Original Research Article
Pages 15-18

6. Furfural loss reactions Original Research Article
Pages 19-22

7. The “Paradox” of furfural yields Original Research Article
Pages 23-27

8. The discoloration of furfural Original Research Article
Pages 28-33

9. Raw materials Original Research Article
Pages 34-35

10. Furfural processes Original Research Article
Pages 36-74

11. Distillation of furfural Original Research Article
Pages 75-85

12. In-Line measurement of furfural Original Research Article
Pages 86-91

13. Treatment of furfural waste water Original Research Article
Pages 92-97

14. Applications of furfural Original Research Article
Pages 98-103

15. Carboxylic acids Original Research Article
Pages 104-119

16. Diacetyl and 2,3-pentanedione Original Research Article
Pages 120-149

17. Furfuryl alcohol Original Research Article
Pages 150-155

18. Furan Original Research Article
Pages 156-158

19. Furoic acid Original Research Article
Pages 159-163

20. Difurfural (5,5′-diformyl-2,2′-difuran) Original Research Article
Pages 164-169

21. 2-hydroxyfuranone-(5) Original Research Article
Pages 170-171

22. Acetoin Original Research Article
Pages 172-180

23. Pyrazines Original Research Article
Pages 181-183

24. Tetrahydrofuran Original Research Article
Pages 184-185

25. Polytetrahydrofuran Original Research Article
Pages 186-204

26. Xylose Original Research Article
Pages 205-209

27. Furan dialdehyde Original Research Article
Pages 210-213

28. Furan resins Original Research Article
Pages 214-222

29. Tetrahydrofurfuryl alcohol Original Research Article
Page 223

30. Dihydropyran Original Research Article
Page 224

31. Maleic acid Original Research Article
Pages 225-228

32. Methylfuran Original Research Article
Pages 229-230

33. Pyrolysis of furfural Original Research Article
Pages 231-232

A. Properties of furfural
Pages 234-239

B. Properties of furfuryl alcohol
Page 240

C. Properties of furan
Page 241

D. Properties of tetrahydrofuran
Page 242

E. Properties of diacetyl
Page 243

F. Properties of 2,3-pentanedione
Page 244

G. Properties of acetoin
Page 245

H. Properties of acetic acid
Page 246

I. Properties of formic acid
Page 247

J. Properties of difurfural (5,5′-diformyl-2,2′-difuran)
Page 248

K. Properties of xylose
Page 249

L. Properties of tetrahydrofurfuryl alcohol
Page 250

M. Properties of dihydropyran
Page 251

N. Properties of furoic acid
Page 252

O. Properties of methylfuran
Page 253

P. Properties of 5-methyl furfural
Page 254

Q. Properties of 2-furyl methyl ketone
Page 255

R. Properties of furan dialdehyde
Page 256

S. Explosion limits in air at 760 mm Hg and 20°C
Page 257

T. Spectroscopic polarity
Pages 258-261

U. Pentosan determination
Pages 262-264

V. Methyl pentosan determination
Pages 265-266

a. The entropy effect in furfural loss reactions
Pages 267-270

b. The “temperature compensation” of acidity
Pages 271-272

c. The corrosion debacle in extracting furfural with chloroform
Pages 273-276

d. Corrosion in the extractive distillation of diacetyl
Pages 277-280

e. Corrosion in the extraction of acetic acid and formic acid
Pages 281-282

f. Neutralization of raw furfural
Pages 283-287

g. Distillation measures against the acidity of raw furfural
Pages 288-295

h. Flashing of residues
Pages 296-299

i. Operational details of the QUAKER OATS batch process
Pages 300-302

j. Operational details of the ROSENLEW process
Pages 303-304

k. Operational details of a ROSENLEW distillation
Pages 305-306

l. Acidity conversion chart
Pages 307-308

m. Extraction of vegetable oils with furfural
Pages 309-313

n. Furoyl chloride
Pages 314-316

o. Furfural as a solvent
Pages 317-318

p. The resinification loss in furfural reactors
Pages 319-322

q. The condensation loss in furfural reactors
Pages 323-326

r. Odd applications
Pages 327-333

Epilogue
Page 334

Subject index
Pages 335-358