108
Chapter 5 · The Coproduct of Oleochemistry - Glycerol
5
Ciriminna R, Della Pinna C, Rossi M, Pagliaro M (2014)
Understanding the glycerol market. Eur J Lipid Sci
Technol 116:1432–1439
Quispe CAG, Coronado CJR, Carvalho JA Jr (2013) Glycerol: production, consumption, prices, characterization and new trends in combustion. Renew Sustain
Energy Rev 27:475–493
De Santos Silva M, Cost Ferreira P (eds) (2012) Glycerol -
Production, structure and applications. Nova Science
Behr A, Pérez Gomes J (2010) The refinement of renewable resources: New important derivatives of fatty
acids and glycerol. Eur J Lipid Sci Technol 112:31–50
Behr A, Eilting J, Irawadi K, Leschinski J, Lindner F (2008)
Improved utilization of renewable resources: new
important derivatives of glycerol. Green Chem 10:13–30
Pagliaro M, Rossi M (2008) The future of glycerol. RSC
Publishing, Cambridge
Zhou C-H, Beltramini JN, Fan Y-X, Lu GQ (2008) Chemoselective catalytic conversion of glycerol as a biorenewable source to valuable commodity chemicals. Chem
Soc Rev 37:527–549
Original Papers
Nda-Umar UI, Ramli I, Taufiq-Yap YH, Muhamad EN (2019)
An overview of recent research in the conversion
of glycerol into biofuels, fuel additives and other
bio-based chemicals. Catalysts 9:15
Wang Y, Xiao Y, Xiao G (2019) Sustainable value-added C 3
chemicals from glycerol transformations. Chin J Chem
Eng. 7 https://doi.org/10.1016/j.cjche.2019.03.001
Bagnato G, Iulianelli A, Sanna A, Basile A (2017) Glycerol
production and transformation: a critical review with
particular emphasis on glycerol reforming reaction
for producing hydrogen in conventional and membrane reactors. Membranes 7:17
Diaz JA, Skrzynska E, Girardon J-S, Ftouni J, Capron M,
Dumeignil F, Fongarland P (2016) Kinetic modeling
of the quasi-homogeneous oxidation of glycerol over
unsupported gold particles in the liquid phase. Eur J
Lipid Sci Technol 118(1):72–79
Behr A, Kleyensteiber A, Domke L (2016) Herstellung von
Glycerin-tert-butylethern – Entwicklung vom Labor
bis zur Miniplant. Chem Ing Tech 88:1082–1094
Behr A, Irawadi KA (2015) Glycerin-oxidation mit magnetisch abtrennbaren Nanokatalysatoren. Chem Ing Tech
87:1726–1732
Tan HW, Abdul Aziz AR, Aroua MK (2013) Glycerol production and its applications as a raw material: a review.
Renew Sustain Energy Rev 27:118–127
Martin A, Armbruster U, Gandarias I, Arias PL (2013) Glycerol hydrogenolysis into propanediols using in situ
generated hydrogen - A critical review. Eur J Lipid Sci
Technol 115:9–27
Coronado CJR (2013) Glycerol: production, consumption,
prices, characterization and new trends in combustion. Renew Sustain Energy Rev 27:475–493
Martin A, Richter M (2011) Oligomerization of glycerol - A
critical review. Eur J Lipid Sci Technol 113:100–117
Neubert L, Paetzold E, Fischer C, Kempers P, Schörken U,
Schümann U, Sadlowski T, Beller M, Kragl U (2011)
Acetale als neuartige Kraftstoffadditive aus Glycerin
und Olefinen. Chem Ing Tech 83:322–330
product because it can be converted
relatively easily into numerous industrial
basic chemicals, e.g. methanol, alkenes,
alkanes, aromatics, aldehydes or alcohols.
In addition, the synthesis gas can be
converted into carbon dioxide and
hydrogen (water–gas shift reaction,
WGSR). This combination of reforming
and WGSR is an interesting source of
pure, oxygen-free hydrogen that can be
used, for example, in fuel cells.
? Ten Quickies
1. What is the approximate weight
percentage of glycerol in soy, sunflower
or new rapeseed oil?
2. Describe the miscibility of glycerol with
other solvents!
3. In which apparatus can you distill
glycerol?
4. What is “kosher” glycerol?
5. How is glyceryl trinitrate produced?
6. How is triacetin synthesized?
7. How is glycerol carbonate technically
produced? Which molecule is formed
during its cleavage?
8. How does the process for the synthesis of
glycerol tertiary butyl ether (GTBE) from
glycerol and isobutene ensures that only
the desired higher GTBE leave the plant?
9. Which substances do you use for the
one-pot synthesis of long-chain glycerol
acetals in a pressure reactor?
10. Why is an economical synthesis of
1,3-propanediol from glycerol of great
interest?
References
Monographs and Review Articles
Pagliaro M (2017) Glycerol - The renewable platform
chemical. Elsevier, Amsterdam
Mota C, Peres Pinto B, de Lima AL (2017) Glycerol - A versatile renewable feedstock for the chemical industry.
Springer
Ciriminna R, Pagliaro M (2016) Sustainable production of
glycerol. In: Encyclopedia of inorganic and bioinorganic chemistry. Wiley
Ye XP, Ren S (2014) Value-added chemicals from glycerol.
In: ACS Symposium series, vol 1178. American Chemical Society, pp 43–80 (Chap. 3)
Chapter 5 · The Coproduct of Oleochemistry - Glycerol
5
Ciriminna R, Della Pinna C, Rossi M, Pagliaro M (2014)
Understanding the glycerol market. Eur J Lipid Sci
Technol 116:1432–1439
Quispe CAG, Coronado CJR, Carvalho JA Jr (2013) Glycerol: production, consumption, prices, characterization and new trends in combustion. Renew Sustain
Energy Rev 27:475–493
De Santos Silva M, Cost Ferreira P (eds) (2012) Glycerol -
Production, structure and applications. Nova Science
Behr A, Pérez Gomes J (2010) The refinement of renewable resources: New important derivatives of fatty
acids and glycerol. Eur J Lipid Sci Technol 112:31–50
Behr A, Eilting J, Irawadi K, Leschinski J, Lindner F (2008)
Improved utilization of renewable resources: new
important derivatives of glycerol. Green Chem 10:13–30
Pagliaro M, Rossi M (2008) The future of glycerol. RSC
Publishing, Cambridge
Zhou C-H, Beltramini JN, Fan Y-X, Lu GQ (2008) Chemoselective catalytic conversion of glycerol as a biorenewable source to valuable commodity chemicals. Chem
Soc Rev 37:527–549
Original Papers
Nda-Umar UI, Ramli I, Taufiq-Yap YH, Muhamad EN (2019)
An overview of recent research in the conversion
of glycerol into biofuels, fuel additives and other
bio-based chemicals. Catalysts 9:15
Wang Y, Xiao Y, Xiao G (2019) Sustainable value-added C 3
chemicals from glycerol transformations. Chin J Chem
Eng. 7 https://doi.org/10.1016/j.cjche.2019.03.001
Bagnato G, Iulianelli A, Sanna A, Basile A (2017) Glycerol
production and transformation: a critical review with
particular emphasis on glycerol reforming reaction
for producing hydrogen in conventional and membrane reactors. Membranes 7:17
Diaz JA, Skrzynska E, Girardon J-S, Ftouni J, Capron M,
Dumeignil F, Fongarland P (2016) Kinetic modeling
of the quasi-homogeneous oxidation of glycerol over
unsupported gold particles in the liquid phase. Eur J
Lipid Sci Technol 118(1):72–79
Behr A, Kleyensteiber A, Domke L (2016) Herstellung von
Glycerin-tert-butylethern – Entwicklung vom Labor
bis zur Miniplant. Chem Ing Tech 88:1082–1094
Behr A, Irawadi KA (2015) Glycerin-oxidation mit magnetisch abtrennbaren Nanokatalysatoren. Chem Ing Tech
87:1726–1732
Tan HW, Abdul Aziz AR, Aroua MK (2013) Glycerol production and its applications as a raw material: a review.
Renew Sustain Energy Rev 27:118–127
Martin A, Armbruster U, Gandarias I, Arias PL (2013) Glycerol hydrogenolysis into propanediols using in situ
generated hydrogen - A critical review. Eur J Lipid Sci
Technol 115:9–27
Coronado CJR (2013) Glycerol: production, consumption,
prices, characterization and new trends in combustion. Renew Sustain Energy Rev 27:475–493
Martin A, Richter M (2011) Oligomerization of glycerol - A
critical review. Eur J Lipid Sci Technol 113:100–117
Neubert L, Paetzold E, Fischer C, Kempers P, Schörken U,
Schümann U, Sadlowski T, Beller M, Kragl U (2011)
Acetale als neuartige Kraftstoffadditive aus Glycerin
und Olefinen. Chem Ing Tech 83:322–330
product because it can be converted
relatively easily into numerous industrial
basic chemicals, e.g. methanol, alkenes,
alkanes, aromatics, aldehydes or alcohols.
In addition, the synthesis gas can be
converted into carbon dioxide and
hydrogen (water–gas shift reaction,
WGSR). This combination of reforming
and WGSR is an interesting source of
pure, oxygen-free hydrogen that can be
used, for example, in fuel cells.
? Ten Quickies
1. What is the approximate weight
percentage of glycerol in soy, sunflower
or new rapeseed oil?
2. Describe the miscibility of glycerol with
other solvents!
3. In which apparatus can you distill
glycerol?
4. What is “kosher” glycerol?
5. How is glyceryl trinitrate produced?
6. How is triacetin synthesized?
7. How is glycerol carbonate technically
produced? Which molecule is formed
during its cleavage?
8. How does the process for the synthesis of
glycerol tertiary butyl ether (GTBE) from
glycerol and isobutene ensures that only
the desired higher GTBE leave the plant?
9. Which substances do you use for the
one-pot synthesis of long-chain glycerol
acetals in a pressure reactor?
10. Why is an economical synthesis of
1,3-propanediol from glycerol of great
interest?
References
Monographs and Review Articles
Pagliaro M (2017) Glycerol - The renewable platform
chemical. Elsevier, Amsterdam
Mota C, Peres Pinto B, de Lima AL (2017) Glycerol - A versatile renewable feedstock for the chemical industry.
Springer
Ciriminna R, Pagliaro M (2016) Sustainable production of
glycerol. In: Encyclopedia of inorganic and bioinorganic chemistry. Wiley
Ye XP, Ren S (2014) Value-added chemicals from glycerol.
In: ACS Symposium series, vol 1178. American Chemical Society, pp 43–80 (Chap. 3)