Introduction to Biodiesel Chemistry
Terms and Background Information
Basic Organic Chemistry
Organic chemistry is the branch of chemistry that deals with organic compounds.
Organic compounds are compounds that (with a few exceptions such as carbon dioxide
gas) contain the element carbon.
The properties of organic compounds are dependent primarily on the physical structure of
the molecules and by the presence of functional groups, which categorize organic
compounds in different groupings, such as alcohols, acids, esters, aldehydes, or ketones,
just to name a few.
If a component of an organic compound is not important to the reaction being defined, it
is often represented on paper as R, which indicates “organic rest.”
What is Biodiesel?
Biodiesel is composed of mono alkyl esters of long chain fatty acids derived from
renewable lipid sources, such as vegetable oil or animal fats.
Esters are organic compounds composed of an alcohol and an organic acid.
Alcohols are organic compounds that contain a functional group OH (hydroxide).
Carboxylic acids are organic compounds that contain a functional group COOH
(carboxyl).
Long chain fatty acids are carboxylic acids that are composed of single chains of 12 to 24
carbons with a carboxyl group.
What is Vegetable Oil?
Vegetable oil is composed of triglycerides of long chain fatty acids attached to glycerol,
which is a type of alcohol. Each triglyceride contains one glycerol and three long chain
fatty acids.
The process used to make biodiesel is called transesterification because it is a process of
transforming one type of ester into another.
prepared by John Bush for Biodiesel Collective Conference 2008
contact:
[email protected] Examples of Organic Compounds
Alcohols – containing a hydroxyl group OH
Methanol Ethanol
CH3OH CH3CH2OH
Carboxylic Acids – containing a carboxyl group COOH
Formic (Methanoic) Acid Acetic (Ethanoic) Acid
CH2O2 CH3COOH
Esters – alcohols bonded to acids
Ethyl Acetate
C 4 H8 O2
prepared by John Bush for Biodiesel Collective Conference 2008
contact:
[email protected] Glycerol, Fatty Acids, Triglycerides, and Biodiesel
Glycerol (Glycerine)
Fatty Acids
Triglyceride – Fatty Acid Ester of Glycerol
Biodiesel – Fatty Acid Ester of a Simple Alcohol
prepared by John Bush for Biodiesel Collective Conference 2008
contact:
[email protected] Biodiesel Chemistry
Reactions Contributing to Methyl Ester Production
1. Transesterification of Fats (Triglycerides) to form Fatty Acid Methyl
Esters and Glycerol
1 Triglyceride + 3 Methanol ↔ 3 Methyl Ester + 1 Glycerol
• The fatty acid R groups remain unchanged
• This reaction is facilitated with a strong base catalyst
2. Reaction of Catalyst (NaOH) with Methanol
CH3OH + NaOH → CH3O-Na + H2O
• CH3O-Na exists as the anion CH3O- and the cation Na+
3. The reaction of Methoxide with Triglyceride
O O
|| ||
CH2-O-C-R CH2-O-C-R
| |
| O | O
| || | ||
CH-O-C-R + CH3O- → CH-O- + CH3O-C-R
| |
| O | O
| || | ||
CH2-O-C-R CH2-O-C-R
Triglyceride + Methoxide Triglyceride Anion + Methyl Ester
• The triglyceride anion then needs a proton to form a diglyceride. If
the proton comes from another methanol, a new methoxide ion is
formed, regenerating the catalyst.
prepared by John Bush for Biodiesel Collective Conference 2008
contact:
[email protected] Biodiesel Chemistry
Reactions Inhibiting Methyl Ester Production
1. Hydrolysis of Triglyceride to form Diglyceride and Free Fatty Acid
O O
|| ||
CH2-O-C-R CH2-O-C-R
| |
| O | O
| || | ||
CH-O-C-R + H2O → CH-OH + HO-C-R
| |
| O | O
| || | ||
CH2-O-C-R CH2-O-C-R
• This reaction is particularly prevalent in deep fryers, and is the
primary reason used cooking oil contains free fatty acids
• It can also happen during biodiesel processing. The presence of a
base catalyst facilitates this reaction in a similar way as it
facilitates transesterification, except the end result is soap.
2. Reaction of Alkali Catalyst with Free Fatty Acid to form Soap
NaOH + HOC(O)R → H2O + Na-OC(O)R
• Note that water is also a product
Summary:
Water can react in a similar way as methanol with triglycerides,
except it results in free fatty acid production. Free fatty acids form soaps
with alkali catalysts. Therefore, either the presence of water or free fatty
acids will limit the effectiveness of the catalyst and inhibit the completion of
the transesterification reaction that produces methyl ester.
prepared by John Bush for Biodiesel Collective Conference 2008
contact:
[email protected]
