Topics for Today From Soap to Biodiesel!. Topics for Today Why biodiesel? How are soap and...
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Transcript of Topics for Today From Soap to Biodiesel!. Topics for Today Why biodiesel? How are soap and...
Topics for TodayTopics for Today
From Soap to Biodiesel!From Soap to Biodiesel!
Topics for TodayTopics for Today
Why biodiesel?Why biodiesel? How are soap and biodiesel different?How are soap and biodiesel different?
No text readings
Topics for FridayTopics for Friday
EXAM 4!!!!
For MondayFor Monday
Connecting the amino acids…Connecting the amino acids…
TopicsTopics
Amines (review)Amines (review) Amides (review)Amides (review) Nylons (review)Nylons (review) Amino AcidsAmino Acids ProteinsProteins
Readings for MondayReadings for Monday
11.6 Proteins: First among equals11.6 Proteins: First among equals 11.7 Good nutrition and alternative 11.7 Good nutrition and alternative
diets: Getting enough protein diets: Getting enough protein
Topics for TodayTopics for Today
From Soap to Biodiesel!!From Soap to Biodiesel!!
Review - SoapReview - Soap
Generic term for the Generic term for the soluble salt of a fatty acidsoluble salt of a fatty acid
SopanificationSopanification
The process of making soapThe process of making soap– 1) Hydrolysis of the fat (water is used)1) Hydrolysis of the fat (water is used)– 2) Neutralizing the fatty acid (water is 2) Neutralizing the fatty acid (water is
produced)produced)
When soaps DON’T work…When soaps DON’T work…
What is hard water?
Water with lots of Ca2+
and Mg2+ ions
Soluble in water
“Separates” into ions
Soap in soft waterSoap in soft water
Soap in soft waterSoap in soft water
C
O -
O
Na+
CO-
O
CO
-
O
CO-
O
Na+
Na+
Na+
Soap interacts with the MgSoap interacts with the Mg2+2+ and and CaCa2+2+ ions. ions.
Soap in hard waterSoap in hard water
NOT soluble!!!!
Soap in hard waterSoap in hard water
Mg2+
CO-
O
CO-
O
Mg2+
CO-
O
CO-
O
Na+
Na+Na+
Na+
Soaps form complexes
with Mg2+ and Ca2+!!
So what?
Soap in hard waterSoap in hard water
Mg2+
CO-
O
CO-
O
Mg2+
CO-
O
CO-
O
Na+
Na+Na+
Na+
Insoluble in water (soap scum)!!!
Soap (soluble)Soap (soluble)
SCUM (insoluble)SCUM (insoluble)
Falls out of the waterFalls out of the water
C
O-
O
Na+
C
O-
O
Na+
+ Ca2+
(or Mg2+)
C
O-
O
Mg2+ (or Ca2+)
C
O-
O
+ 2Na+
SCUM
How do you prevent soap
scum?
1) Use soft water
2) Use detergents
Why detergents?
DetergentsDetergents
Same as soaps, but a different polar Same as soaps, but a different polar end.end.
Usually a sulfate or a phosphate!!
Non-polar hydrocarbon chain
Polar ionic group, soluble in water
SoapSoapsodium stearate sodium stearate
H3C (CH2)16 C
O
ONa +
H3C (CH2)16 C
O
ONa +
Non-polar hydrocarbon chain
Polar ionic group, soluble in water
DetergentDetergentSodium Lauryl SulfonateSodium Lauryl Sulfonate
10 S
O─
Why don’t detergents
make scum?
H3C (CH2)16 C
O
ONa +
H3C (CH2)16 C
O
ONa +
10 S
O
10 S
O
Mg2+
─
─
Soluble!
Soap on the WebSoap on the Web
Cator.hsc.edu/~kmd/caveman/Cator.hsc.edu/~kmd/caveman/projects/soapprojects/soap
History of soap makingHistory of soap making
www.alcasoft.com/soapfact/history.hwww.alcasoft.com/soapfact/history.htmltml
Topics for TodayTopics for Today
From Soap to Biodiesel!!From Soap to Biodiesel!!Review
M. King Hubbert
1903 - 1989
"Our ignorance is not so vast as our failure to use what we know."
August, 2005: Chevron August, 2005: Chevron Full Page Magazine Adds Full Page Magazine Adds
willyoujoinus.com
It took us 125 years to use
the first trillion barrels of oil.
We’ll use the next trillion in 30.
So why should you care?
ReviewReview
Where does gasoline come
from?
Liquified Petroleum Gas (LPG)
Gasoline
Kerosene and Diesel Fuel
Heating Oil and Diesel Fuel
Lubricating Oil
Solids (Paraffin, Asphalt, etc)
Gasoline?
Gasoline
Liquified Petroleum Gas (LPG)
Gasoline
Kerosene and Diesel Fuel
Heating Oil and Diesel Fuel
Lubricating Oil
Solids (Paraffin, Asphalt, etc)
Diesel?
Diesel Fuel
Rudolf DieselRudolf Diesel
Invented the diesel engine
in 1892
- Rudolph Diesel
“The use of plant oil as fuel may seem insignificant today. But such products can in time become just as important as today’s kerosene and coal-tar-products”
- Rudolph Diesel
“The use of plant oil as fuel may seem insignificant today. But such products can in time become just as important as today’s kerosene and coal-tar-products”
Biodiesel!
How do we use plant oil as a
fuel?
What is biodiesel?
Chemically speaking…Chemically speaking…
The (methyl) ester of a The (methyl) ester of a fatty acid!fatty acid!
How is it different from a
soap??
Review - SoapReview - Soap
The soluble salt of a fatty The soluble salt of a fatty acid!acid!
CO
O- Na+Soap – Salt of a fatty acid
CO
OCH3Biodiesel – Methyl Ester of a fatty acid
Where can we get the plant oils
from?
Biodiesel FeedstocksBiodiesel Feedstocks
Canola
Soybeans
SunflowerLinseed
SafflowerCorn oil
Rapeseed
Which is best?
Plants utilize photosynthesis to convert solar
energy into chemical energy. Different plants
produce usable oil at different rates. For
Example:•Soybean: 40 to 50 US gal/acre (35 to 45,000 L/km²)
•Rapeseed: 110 to 145 US gal/acre (100 to 130,000 L/km²)
•Mustard: 140 US gal/acre (130,000 L/km²)
•Jatropha: 175 US gal/acre (160,000 L/km²)
•Palm oil: 650 US gal/acre (580,000 L/km²)
•Algae: 10,000 to 20,000 US gal/acre (9,000,000 to
18,000,000 L/km²)
http://www.biodiesel.org/resources/reportsdatabase/default.asp
Q? How much energy goes into growing and harvesting these feedstocks?Q? What are the fertilizer requirements for each of these feedstocks?
Making biodiesel – green refineries of the future?
100 g soybean oil 100.4 g biodiesel + 10.9 g methanol + 10.4 g glycerol
Soybeans
More than 50% of the fatty acids are linoleic acid!
A polyunsaturate
d fatty acid
C18H32O2
How does this
compare with diesel
fuel?
Diesel Fuel
Biodiesel products are similar to Biodiesel products are similar to conventional petrodieselconventional petrodiesel
Cetane (C16H34)
Methyl Linolenate(C19H32O2)
A fatty acid methyl ester (FAME)
BIODIESEL COMPONENT
An unbranched alkane (paraffin)
PETERODIESEL COMPONENT
NEW!! Biodiesel RoadmapNEW!! Biodiesel Roadmap
Ester Alcohol+ Ester Alcohol+NEW NEW
Reactive
Species
Heat
Biodiesel RoadmapBiodiesel Roadmap
Oil Methanol+ Biodiesel!
Glycerol+
Reactive
Species
Fat
What do we start with?
Heat
- +
Sodium methoxide salt
H2OCH3OH NaOH CH3O-Na+ H2O+ +
Sodium Hydroxide
Methanol Water
Step 1
Create the “reactive species”
Don’t need to
memorize this!
Biodiesel RoadmapBiodiesel Roadmap
Oil Methanol+ Biodiesel!
Glycerol+
Reactive
Species
Fat Heat
C OH
C O
OCH
H
H
H
CO
CO
CO
+ CH3O-Na+
heat
Step 2! Making Biodiesel
Oil
Fat
Reactive
Species
C OH
C O
OCH
H
H
H
CO
CO
CO
+ 2CH3O-Na+
heat
Step 2! Making Biodiesel
Oil
Fat
Reactive
Species
C OH
C O
OCH
H
H
H
CO
CO
CO
+ 3CH3O-Na+
heat
Step 2! Making Biodiesel
Oil
Fat
Reactive
Species
Step 2!
CH
C
O-Na+CH
H
H
H
OC+ CH3O
Making Biodiesel
O-Na+
O-Na+
3
CH
C
O-Na+CH
H
H
H
Step 3!Regenerate the
reactive species!!
+ CH3OHheatheat
Methanol
O-Na+
O-Na+
3
CH
C
OHCH
H
H
H
+ CH3O-Na+
Step 3!
Reactive
Species
OH
OH
3
Glycerol!
Once for each fatty acid
chain!
Overall Reaction?
Triglyceride
Alcohol
HEATC OH
C O
OCH
H
H
H
CO
CO
CO
CH3OH+
CH O
CH2 O
OCH2
H
H
H
+ C
OCH3
O3
OH-
Glycerol
TransesterificationTransesterification
Forming one ester from another Forming one ester from another ester!!!ester!!!
Why is there no water in
this reaction?
SopanificationSopanification
HEAT / H2OC OH
C O
OCH
H
H
H
CO
CO
CO
3NaOH+
CH O
CH2 O
OCH2
H
H
H
+ C
O-
O
CH3 (CH2)163
Na+
We get soap!!!
Review… Review…
OHH
.. ..
Water
OCH3H
.. ..
Methanol
versus
Benefits of biodiesel?
Reduced criteria air pollutants!
Criteria PollutantsCriteria Pollutants
Defined by the EPADefined by the EPA– COCO
– SOSO22
– NONOxx
– PM2.5 and PM10PM2.5 and PM10
– OO33 (ozone) (ozone)
– leadlead
12%
20%
2%
12%
Extremely low sulfur content!
Compatible with current diesel
engines!
Where is biodiesel being
used?
Environmental group works to run cars on Culver’s old frying oil
One of the first uses of transesterified vegetable oil (biodiesel) was powering heavy duty vehicles in South Africa before World War II. The name "biodiesel" has been given to transesterified vegetable oil to describe its use as a diesel fuel. It was patented in the US in the 1940s by Colgate (and other) scientists. The 1940s researchers were looking for a method to produce glycerin more readily, in order to produce explosives for World War II. Many of the methods used today by producers and home brewers have their origin in the original 1940s research.
One of the first uses of transesterified vegetable oil (biodiesel) was powering heavy duty vehicles in South Africa before World War II. The name "biodiesel" has been given to transesterified vegetable oil to describe its use as a diesel fuel. It was patented in the US in the 1940s by Colgate (and other) scientists. The 1940s researchers were looking for a method to produce glycerin more readily, in order to produce explosives for World War II. Many of the methods used today by producers and home brewers have their origin in the original 1940s research.
Glycerol!
Where is biodiesel
produced?
Much of the commercially sold biodiesel, including most of Red Carpet's, is domestically made from soy beans and shipped from the Midwest
http://www.biodiesel.org/
Can I find a pumping station
near me?
Depends where you
live!