86
Chapter 4 · There is More to Oleochemistry - Reactions at the Fatty Acid Alkyl Chain
4
9. How can polyunsaturated fatty acids
(PUFA) be converted into conjuenic
acids?
10. Name some typical catalysts for the
hydrogenation of C=C double bonds of
oleochemicals!
References
Monographs and Review Articles
Vorholt AJ, Behr A (2017) Oleochemistry. In: Cornils B,
Herrmann WA, Beller M, Paciello R (eds) Applied
homogeneous catalysis with organometallic compounds (Chap. 34). Wiley-VCH, Weinheim
Behr A, Vorholt AJ (2017) Homogeneous Catalysis with
Renewables. Springer International Publications
Parambath A (ed) (2017) Cashew nut shell liquid. Springer
International Publications
Enferadi Kerenkan A, Béland F, Do T-O (2016) Chemically
catalyzed oxidative cleavage of unsaturated fatty
acids and their derivatives into valuable products
for industrial applications: a review and perspective.
Catal Sci Technol 6:971–987
Seidensticker T, Vorholt AJ, Behr A (2016) The mission of
addition and fission - catalytic functionalization of
oleochemicals. Eur J Lipid Sci Technol 118:3–25
Behr A, Vorholt AJ, Ostrowski KA, Seidensticker T (2014)
Towards resource efficient chemistry: tandem reactions with renewables. Green Chem 16:982–1006
Honary L, Richter E (2011) Biobased Lubricants and
Greases, Wiley-VCH, Weinheim
Behr A, Westfechtel A, Perez Gomes J (2008) Catalytic processes for the technical use of natural fats and oils.
Chem Eng Technol 31:700–714
Behr A (2008) Angewandte homogene Katalyse.
Wiley, Weinheim, Kap. 44: Homogene Katalyse mit
nachwachsenden Rohstoffen
Corma A, Iborra S, Velty A (2007) Chemical routes for the
transformation of biomass into chemicals. Chem Rev
107:2411–2502
Meier MAR, Metzger JO, Schubert US (2007) Plant oil
renewable resources as green alternatives in polymer
science. Chem Soc Rev 36:1788–1802
Centi G, van Santen RA (eds) (2007) Catalysis for renewables: from feedstock to energy production.
Wiley-VCH, Weinheim
van Bekkum H, Gallezot P (eds) Catalytic conversion of
renewables. Special issue of “Topics in Catalysis”
27(1–4)
Biermann U, Friedt W, Lang S, Lühs W, Machmüller G,
Metzger JO, Rüsch gen. Klaas M, Schäfer HJ, Schneider MP (2000) Neue Synthesen mit Ölen und Fetten
als nachwachsende Rohstoffe für die chemische
Industrie. Angew Chem 112:2292–2310
5 The production of oleochemical
polymers is currently an important
research goal. Approaches to this are,
for example, follow-up reactions of
the 10-undecenoic acid accessible
from ricinoleic acid or the isomerizing
alkoxycarbonylation of methyl oleate
with subsequent condensation to
polyesters.
5 Selective hardening of polyunsaturated
oleochemicals can be carried out with
palladium nanocatalysts, which can be
easily produced and recycled.
5 Numerous further additions to the
C=C double bond are possible, e.g.
platinum-catalyzed hydrosilylation,
which can be used to produce special
hydrophobic silicones.
? Ten Quickies
1. How many steps are required to synthesize
an α-ester sulfonate (AES) from a (saturated)
triglyceride? Can you compare the
synthesis of the competitor product, linear
alkylbenzene sulfonates (LABS)?
2. Name (up to seven) methods for
synthesizing oleochemical di- or
polyols suitable for the production of
polyurethanes!
3. Compare the ozonolyses of oleic acid and
erucic acid with each other!
4. In the hydroformylation of unsaturated
oleochemicals, internal or terminal
formyl groups can be obtained. How, in
principle, can this be controlled?
5. How can alkyl-branched fatty acids be
obtained? We got to know three methods
in 7 Chaps. 3 and this chapter.
6. Carry out (on paper) the ethenolysis of
petroselinic acid C18:1 (Δ6/c.)! Which two
products are formed?
7. Which four products can be produced by
cross-metathesis of methyl oleate with
allyl chloride?
8. Briefly describe the current ruthenium
metathesis catalysts!
Chapter 4 · There is More to Oleochemistry - Reactions at the Fatty Acid Alkyl Chain
4
9. How can polyunsaturated fatty acids
(PUFA) be converted into conjuenic
acids?
10. Name some typical catalysts for the
hydrogenation of C=C double bonds of
oleochemicals!
References
Monographs and Review Articles
Vorholt AJ, Behr A (2017) Oleochemistry. In: Cornils B,
Herrmann WA, Beller M, Paciello R (eds) Applied
homogeneous catalysis with organometallic compounds (Chap. 34). Wiley-VCH, Weinheim
Behr A, Vorholt AJ (2017) Homogeneous Catalysis with
Renewables. Springer International Publications
Parambath A (ed) (2017) Cashew nut shell liquid. Springer
International Publications
Enferadi Kerenkan A, Béland F, Do T-O (2016) Chemically
catalyzed oxidative cleavage of unsaturated fatty
acids and their derivatives into valuable products
for industrial applications: a review and perspective.
Catal Sci Technol 6:971–987
Seidensticker T, Vorholt AJ, Behr A (2016) The mission of
addition and fission - catalytic functionalization of
oleochemicals. Eur J Lipid Sci Technol 118:3–25
Behr A, Vorholt AJ, Ostrowski KA, Seidensticker T (2014)
Towards resource efficient chemistry: tandem reactions with renewables. Green Chem 16:982–1006
Honary L, Richter E (2011) Biobased Lubricants and
Greases, Wiley-VCH, Weinheim
Behr A, Westfechtel A, Perez Gomes J (2008) Catalytic processes for the technical use of natural fats and oils.
Chem Eng Technol 31:700–714
Behr A (2008) Angewandte homogene Katalyse.
Wiley, Weinheim, Kap. 44: Homogene Katalyse mit
nachwachsenden Rohstoffen
Corma A, Iborra S, Velty A (2007) Chemical routes for the
transformation of biomass into chemicals. Chem Rev
107:2411–2502
Meier MAR, Metzger JO, Schubert US (2007) Plant oil
renewable resources as green alternatives in polymer
science. Chem Soc Rev 36:1788–1802
Centi G, van Santen RA (eds) (2007) Catalysis for renewables: from feedstock to energy production.
Wiley-VCH, Weinheim
van Bekkum H, Gallezot P (eds) Catalytic conversion of
renewables. Special issue of “Topics in Catalysis”
27(1–4)
Biermann U, Friedt W, Lang S, Lühs W, Machmüller G,
Metzger JO, Rüsch gen. Klaas M, Schäfer HJ, Schneider MP (2000) Neue Synthesen mit Ölen und Fetten
als nachwachsende Rohstoffe für die chemische
Industrie. Angew Chem 112:2292–2310
5 The production of oleochemical
polymers is currently an important
research goal. Approaches to this are,
for example, follow-up reactions of
the 10-undecenoic acid accessible
from ricinoleic acid or the isomerizing
alkoxycarbonylation of methyl oleate
with subsequent condensation to
polyesters.
5 Selective hardening of polyunsaturated
oleochemicals can be carried out with
palladium nanocatalysts, which can be
easily produced and recycled.
5 Numerous further additions to the
C=C double bond are possible, e.g.
platinum-catalyzed hydrosilylation,
which can be used to produce special
hydrophobic silicones.
? Ten Quickies
1. How many steps are required to synthesize
an α-ester sulfonate (AES) from a (saturated)
triglyceride? Can you compare the
synthesis of the competitor product, linear
alkylbenzene sulfonates (LABS)?
2. Name (up to seven) methods for
synthesizing oleochemical di- or
polyols suitable for the production of
polyurethanes!
3. Compare the ozonolyses of oleic acid and
erucic acid with each other!
4. In the hydroformylation of unsaturated
oleochemicals, internal or terminal
formyl groups can be obtained. How, in
principle, can this be controlled?
5. How can alkyl-branched fatty acids be
obtained? We got to know three methods
in 7 Chaps. 3 and this chapter.
6. Carry out (on paper) the ethenolysis of
petroselinic acid C18:1 (Δ6/c.)! Which two
products are formed?
7. Which four products can be produced by
cross-metathesis of methyl oleate with
allyl chloride?
8. Briefly describe the current ruthenium
metathesis catalysts!