59
3
3.2 · Reactions at the Carboxy Group of Fatty Acids
3. In an oleochemical factory, stearic acid
on the one hand and stearyl alcohol
on the other hand are to be purified by
distillation. How to proceed?
4. Why did soap production in Europe
increase sharply in the second half of the
nineteenth century?
5. Why are 1,2-propanediol and isopropanol
by-products of direct hydrogenation of
fats? Why not 1,3-propanediol?
6. How can fat esters be industrially
hydrogenated to fatty alcohols? Describe
the arrangement of the catalyst in the
reactor!
7. How can fatty alcohols also be produced
by hydroformylation? What chain lengths
can be achieved? Give examples!
8. How can oleyl alcohol be produced from
methyl oleate?
9. Describe the four-step path from the
fat molecule to the fatty alcohol ether
sulfates!
10. Describe the two syntheses of
the important laundry softener
distearyldimethylammonium chloride,
starting with either stearic acid or stearyl
alcohol!
References
Monographs and Review Articles
Hayes D, Solaiman D, Ashby R (2019) Biobased surfactants, 2nd ed. Academic Press
Rabiu A, Elias S, Oyekola O (2018) Oleochemicals from
palm oil for the Petroleum Industry. IntechOpen
(2018)
Bornscheuer U (2018) Lipid modification by enzymes and
engineered microbes. Academic Press
Ahmad MU (2017) Fatty acids - chemistry, synthesis and
applications, 1st ed. Academic Press
Gupta M (2017) Practical guide to vegetable oil processing, 2nd ed. Academic Press
Spitz L (2016) Soap manufacturing technology, 2nd ed.
Academic Press (2016)
Farr WE, Proctor A (2016) Green vegetable oil processing,
1st rev. ed. AOCS Elsevier
List GR, King JW (eds) (2015) Hydrogenation of fats and
oils: theory and practice, 2nd ed. AOCS-Press
Hernandez EM, Kamal-Eldin A (2013) Processing and
nutrition of fats and oils. Wiley-Blackwell
Ahmad M, Khan MA, Zafar M, Sultana S (2012) Practical
handbook on biodiesel production and properties.
CRC Press
5 Fatty acid esters are produced by
esterification of the fatty acids with
alcohols or preferably by transesterification of the triglycerides with methanol
to fatty acid methyl esters and glycerol.
5 Saponification of fats with caustic soda
or potash lye to soaps and the coproduct
glycerol has been a known technology
for centuries. Today, this reaction is also
predominantly carried out continuously.
5 In the direct hydrogenation of
triglycerides with hydrogen to fatty
alcohols, glycerol, 1,2-propanediol and
isopropanol are the by-products. It has not
yet been carried out on an industrial scale.
5 The most important way to obtain
fatty alcohols is the hydrogenation of
fatty acids or fatty acid methyl esters,
respectively. Depending on the chain
length, liquid-to-solid products are
formed, which are further processed into
surfactants, fatty amines or lubricants, for
example. Natural fatty alcohols based on
renewable raw materials are competing
with synthetic fatty alcohols produced by
the Alfol process or by hydroformylation.
5 Important secondary reactions of fatty
alcohols are ethoxylation to fatty alcohol
ethoxylates (FAE), sulfation to fatty
alcohol sulfates (FAS), sulfation of FAE
to fatty alcohol ether sulfates (FAES),
Fischer reaction with glucose to alkyl
polyglucosides (APG) and condensation
to Guerbet alcohols.
5 Fatty amines can be produced in two
stages from fatty acids or fatty alcohols.
As the corresponding ammonium salts,
they are used as cationic surfactants,
emulsifiers, plasticizers or flotation aids.
5 Other important derivatives are fatty acid
chlorides and fatty acid anhydrides.
? Ten Quickies
1. Name three basic chemicals of
oleochemistry!
2. Compare the glycerol qualities produced
during fat hydrolysis and transesterification of fats!
3
3.2 · Reactions at the Carboxy Group of Fatty Acids
3. In an oleochemical factory, stearic acid
on the one hand and stearyl alcohol
on the other hand are to be purified by
distillation. How to proceed?
4. Why did soap production in Europe
increase sharply in the second half of the
nineteenth century?
5. Why are 1,2-propanediol and isopropanol
by-products of direct hydrogenation of
fats? Why not 1,3-propanediol?
6. How can fat esters be industrially
hydrogenated to fatty alcohols? Describe
the arrangement of the catalyst in the
reactor!
7. How can fatty alcohols also be produced
by hydroformylation? What chain lengths
can be achieved? Give examples!
8. How can oleyl alcohol be produced from
methyl oleate?
9. Describe the four-step path from the
fat molecule to the fatty alcohol ether
sulfates!
10. Describe the two syntheses of
the important laundry softener
distearyldimethylammonium chloride,
starting with either stearic acid or stearyl
alcohol!
References
Monographs and Review Articles
Hayes D, Solaiman D, Ashby R (2019) Biobased surfactants, 2nd ed. Academic Press
Rabiu A, Elias S, Oyekola O (2018) Oleochemicals from
palm oil for the Petroleum Industry. IntechOpen
(2018)
Bornscheuer U (2018) Lipid modification by enzymes and
engineered microbes. Academic Press
Ahmad MU (2017) Fatty acids - chemistry, synthesis and
applications, 1st ed. Academic Press
Gupta M (2017) Practical guide to vegetable oil processing, 2nd ed. Academic Press
Spitz L (2016) Soap manufacturing technology, 2nd ed.
Academic Press (2016)
Farr WE, Proctor A (2016) Green vegetable oil processing,
1st rev. ed. AOCS Elsevier
List GR, King JW (eds) (2015) Hydrogenation of fats and
oils: theory and practice, 2nd ed. AOCS-Press
Hernandez EM, Kamal-Eldin A (2013) Processing and
nutrition of fats and oils. Wiley-Blackwell
Ahmad M, Khan MA, Zafar M, Sultana S (2012) Practical
handbook on biodiesel production and properties.
CRC Press
5 Fatty acid esters are produced by
esterification of the fatty acids with
alcohols or preferably by transesterification of the triglycerides with methanol
to fatty acid methyl esters and glycerol.
5 Saponification of fats with caustic soda
or potash lye to soaps and the coproduct
glycerol has been a known technology
for centuries. Today, this reaction is also
predominantly carried out continuously.
5 In the direct hydrogenation of
triglycerides with hydrogen to fatty
alcohols, glycerol, 1,2-propanediol and
isopropanol are the by-products. It has not
yet been carried out on an industrial scale.
5 The most important way to obtain
fatty alcohols is the hydrogenation of
fatty acids or fatty acid methyl esters,
respectively. Depending on the chain
length, liquid-to-solid products are
formed, which are further processed into
surfactants, fatty amines or lubricants, for
example. Natural fatty alcohols based on
renewable raw materials are competing
with synthetic fatty alcohols produced by
the Alfol process or by hydroformylation.
5 Important secondary reactions of fatty
alcohols are ethoxylation to fatty alcohol
ethoxylates (FAE), sulfation to fatty
alcohol sulfates (FAS), sulfation of FAE
to fatty alcohol ether sulfates (FAES),
Fischer reaction with glucose to alkyl
polyglucosides (APG) and condensation
to Guerbet alcohols.
5 Fatty amines can be produced in two
stages from fatty acids or fatty alcohols.
As the corresponding ammonium salts,
they are used as cationic surfactants,
emulsifiers, plasticizers or flotation aids.
5 Other important derivatives are fatty acid
chlorides and fatty acid anhydrides.
? Ten Quickies
1. Name three basic chemicals of
oleochemistry!
2. Compare the glycerol qualities produced
during fat hydrolysis and transesterification of fats!