Topics for Today From Soap to Biodiesel!. Topics for Today Why biodiesel? How are soap and biodiesel different? No text readings

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!