140
Chapter 6 · Sweet Chemistry - Mono- and Disaccharides
6
References
Monographs and Review Articles to Carbohydrates
Kovac P (ed) (2019) Carbohydrate chemistry: proven synthetic methods, vol 1. In: van der Marel G, Codee J
(eds) (2014), vol 2. CRC Press
Alén R (2018) Carbohydrate chemistry - fundamentals and
applications. World Scientific
Karakashev D, Zhang Y (eds) (2018) BioEnergy and BioChemicals production from biomass and residual
resources. MDPI
Rauter AP, Lindhorst TK, Queneau Y (eds) (2017) Carbohydrate chemistry, vol 42. Royal Society of Chemistry
Farrán A, Cai C, Sandoval M, Xu Y, Liu J, Hernáiz MJ, Linhardt RJ (2015) Green solvents in carbohydrate chemistry: from raw materials to fine chemicals. Chem Rev
115:6811–6853
Mahrwald R (2015) Modern organocatalyzed methods in
carbohydrate chemistry. Springer
Schwedt G (2014) Zuckersüße Chemie - Kohlenhydrate &
Co, 2. Aufl. Wiley-VCH, Weinheim
Wittcoff HA, Reuben BG, Plotkin JS (eds) (2013) Carbohydrates, Chap 16. In: Industrial organic chemicals.
Wiley
Gallezot P (2012) Conversion of biomass to selected
chemical products. Chem Soc Rev 41:1538–1558
Ulber R, Sell D, Hirth T (eds) (2011) Renewable raw materials - new feedstocks for the chemical industry.
Wiley-VCH, Weinheim
Ebermann R, Elmadfa I (2011) Lehrbuch Lebensmittelchemie und Ernährung, Kapitel 3 (Kohlenhydrate).
Springer, Wien, New York
Miljkovic M (2010) Carbohydrates: synthesis, mechanisms
and stereoelectronic effects. Springer, New York
Stick RV, Williams SJ (2009) Carbohydrates: the essential
molecules of life, 2nd ed. Elsevier
Habermehl G, Hammann PE, Krebs HC, Ternes W (2008)
Naturstoffchemie - Eine Einführung. Springer, Berlin
Sinnott ML (2008) Carbohydrate chemistry and biochemistry - structure and mechanism. RSC Publishing
Fraser-Reid B, Tatsuka K, Thiem J (eds) (2008) Glycoscience. Springer-Verlag, Heidelberg
Lindhorst TK (2007) Essentials of carbohydrate chemistry
and biochemistry. Wiley-VCH, Weinheim
Levy DE, Fügedi P (2005) The organic chemistry of sugars.
CRC Press
Lehmann J (2001) Kohlenhydrate - Chemie und Biologie.
Thieme, Stuttgart
Original Papers to Carbohydrates
Sheldon R (2014) Green and sustainable manufacture of
chemicals from biomass: state of the art. Green Chem
16:950–963
Bozell JJ, Petersen GR (2010) Technology development
for the production of biobased products from biorefinery carbohydrates - the US Department of Energy’s
“top 10” revisited. Green Chem 12:539–554
Lichtenthaler FW (2010) Carbohydrates as organic raw
materials. In: Ullmann’s encyclopedia of industrial
chemistry (electronic version). Wiley-VCH, Weinheim
and subsequent crystallization of the sugar
in the “cooking station”. Molasses is formed
as a coproduct.
5 Hydrolysis of sucrose leads to invert
sugar, a mixture of glucose and fructose
that is used as a sweetener in the food
industry.
5 Sucrose can also be converted into
sucrose esters and sucrose ether.
An interesting ether synthesis is the
palladium-catalyzed telomerization
of sucrose with 1,3-butadiene to
sucrose monotelomers, which can be
used as non-ionic surfactants after
hydrogenation. Compared to esters,
ether have the advantage that they are
much more stable under basic conditions.
5 Sucralose is obtained by chlorination
of sucrose, polyhydroxypolycarboxylic
acids by oxidation and isomaltulose by
isomerization.
? Ten Quickies
1. Name at least two monosaccharides and
their occurrence in nature!
2. Lactic acid, accessible by fermentation
of glucose, is an important platform
chemical. Which secondary products can
be produced from it?
3. Which products are produced during the
dehydration of hexoses or pentoses?
4. How can you synthesize monomers for
polycondensates from HMF?
5. What are sugar alcohols? Give examples
and some applications!
6. Describe the industrial process for the
production of alkyl polyglucosides. What
are these APGs used for? What are their
properties?
7. How can you produce anon-ionic
surfactant from glucose by amination?
8. What is lactose? Where does it occur?
How is it obtained?
9. Give as much detail as possible of the
most important process steps in the
extraction of sucrose from sugar beets!
Which by-products are formed? What are
these used for?
10. Name at least five products derived from
sucrose!
Chapter 6 · Sweet Chemistry - Mono- and Disaccharides
6
References
Monographs and Review Articles to Carbohydrates
Kovac P (ed) (2019) Carbohydrate chemistry: proven synthetic methods, vol 1. In: van der Marel G, Codee J
(eds) (2014), vol 2. CRC Press
Alén R (2018) Carbohydrate chemistry - fundamentals and
applications. World Scientific
Karakashev D, Zhang Y (eds) (2018) BioEnergy and BioChemicals production from biomass and residual
resources. MDPI
Rauter AP, Lindhorst TK, Queneau Y (eds) (2017) Carbohydrate chemistry, vol 42. Royal Society of Chemistry
Farrán A, Cai C, Sandoval M, Xu Y, Liu J, Hernáiz MJ, Linhardt RJ (2015) Green solvents in carbohydrate chemistry: from raw materials to fine chemicals. Chem Rev
115:6811–6853
Mahrwald R (2015) Modern organocatalyzed methods in
carbohydrate chemistry. Springer
Schwedt G (2014) Zuckersüße Chemie - Kohlenhydrate &
Co, 2. Aufl. Wiley-VCH, Weinheim
Wittcoff HA, Reuben BG, Plotkin JS (eds) (2013) Carbohydrates, Chap 16. In: Industrial organic chemicals.
Wiley
Gallezot P (2012) Conversion of biomass to selected
chemical products. Chem Soc Rev 41:1538–1558
Ulber R, Sell D, Hirth T (eds) (2011) Renewable raw materials - new feedstocks for the chemical industry.
Wiley-VCH, Weinheim
Ebermann R, Elmadfa I (2011) Lehrbuch Lebensmittelchemie und Ernährung, Kapitel 3 (Kohlenhydrate).
Springer, Wien, New York
Miljkovic M (2010) Carbohydrates: synthesis, mechanisms
and stereoelectronic effects. Springer, New York
Stick RV, Williams SJ (2009) Carbohydrates: the essential
molecules of life, 2nd ed. Elsevier
Habermehl G, Hammann PE, Krebs HC, Ternes W (2008)
Naturstoffchemie - Eine Einführung. Springer, Berlin
Sinnott ML (2008) Carbohydrate chemistry and biochemistry - structure and mechanism. RSC Publishing
Fraser-Reid B, Tatsuka K, Thiem J (eds) (2008) Glycoscience. Springer-Verlag, Heidelberg
Lindhorst TK (2007) Essentials of carbohydrate chemistry
and biochemistry. Wiley-VCH, Weinheim
Levy DE, Fügedi P (2005) The organic chemistry of sugars.
CRC Press
Lehmann J (2001) Kohlenhydrate - Chemie und Biologie.
Thieme, Stuttgart
Original Papers to Carbohydrates
Sheldon R (2014) Green and sustainable manufacture of
chemicals from biomass: state of the art. Green Chem
16:950–963
Bozell JJ, Petersen GR (2010) Technology development
for the production of biobased products from biorefinery carbohydrates - the US Department of Energy’s
“top 10” revisited. Green Chem 12:539–554
Lichtenthaler FW (2010) Carbohydrates as organic raw
materials. In: Ullmann’s encyclopedia of industrial
chemistry (electronic version). Wiley-VCH, Weinheim
and subsequent crystallization of the sugar
in the “cooking station”. Molasses is formed
as a coproduct.
5 Hydrolysis of sucrose leads to invert
sugar, a mixture of glucose and fructose
that is used as a sweetener in the food
industry.
5 Sucrose can also be converted into
sucrose esters and sucrose ether.
An interesting ether synthesis is the
palladium-catalyzed telomerization
of sucrose with 1,3-butadiene to
sucrose monotelomers, which can be
used as non-ionic surfactants after
hydrogenation. Compared to esters,
ether have the advantage that they are
much more stable under basic conditions.
5 Sucralose is obtained by chlorination
of sucrose, polyhydroxypolycarboxylic
acids by oxidation and isomaltulose by
isomerization.
? Ten Quickies
1. Name at least two monosaccharides and
their occurrence in nature!
2. Lactic acid, accessible by fermentation
of glucose, is an important platform
chemical. Which secondary products can
be produced from it?
3. Which products are produced during the
dehydration of hexoses or pentoses?
4. How can you synthesize monomers for
polycondensates from HMF?
5. What are sugar alcohols? Give examples
and some applications!
6. Describe the industrial process for the
production of alkyl polyglucosides. What
are these APGs used for? What are their
properties?
7. How can you produce anon-ionic
surfactant from glucose by amination?
8. What is lactose? Where does it occur?
How is it obtained?
9. Give as much detail as possible of the
most important process steps in the
extraction of sucrose from sugar beets!
Which by-products are formed? What are
these used for?
10. Name at least five products derived from
sucrose!