Methanol and the Home-Brewer

In June 2013, a young man in Queensland died as a result of drinking homemade liquor. It is believed that the liquor contained a toxic level of methanol (also known as wood alcohol). Drinking 10 mL of pure methanol can cause permanent blindness, drinking 30 mL of methanol can kill you.

The first step in the production of homemade liquors, is the fermentation of sugar.
Methanol, CH₃OH,is formed during fermentation.
When fermenting 6 kg of sugar dissolved in water for the production of distilled spirits such as whiskey or vodka, the home-brewer (and home-distiller) will typically find that the concentration of methanol in their brew is about 3 parts per million.

Many fruits are used by the home-brewer as the source of sugar to be fermented. Each fruit will lend a distinctive flavour to the final product. But fruits that are high in pectin will produce greater concentrations of methanol. Apples, apricots, guavas, quinces, plums, gooseberries, and citrus fruits like oranges, all contain high levels of pectin, typically more than 1% by mass pectin. Grapes, cherries and strawberries contain low levels of pectin, less than 1% by mass pectin.

Pectin contains  galacturonic acid which has the structural formula shown below:

In pectin, about 80% of the carboxyl groups in galacturonic acid are esterified with methanol. The remaining non-esterified carboxyl groups exist as the acid, or as salts with sodium, potassium or calcium. When pectin is broken down by enzymes during the brewing process, the methyl esters react with water to produce methanol.

The second step in the production of homemade liquor is the distillation step.
This is the crucial step in removing as much of the toxic methanol as possible.
The boiling point of methanol is about 65^oC, but the boiling point of ethanol (the desired product) is about 78^oC. During the distillation process, the first fraction collected should contain the methanol. This fraction should be collected and discarded. The next fraction should contain the desired liquor. It is highly recommended that any distillate collected after about 96^oC also be discarded.


Reference:
http://www.couriermail.com.au/news/queensland/ballandean-man-bill-lynam-who-lost-his-son-joel-to-homemade-liquor-poisoning-is-thankful-that-other-son-joshua-survived/story-fnihsrf2-1226664893229

Further Reading
http://ausetute.com.au/members/alkanolp.html (members only tutorial on alkanols)
http://ausetute.com.au/members/carboxyl.html (members only tutorial on alkanoic acids) 
http://ausetute.com.au/partspm.html 
http://ausetute.com.au/density.html 

Suggested Study Questions:

1. Draw the structural formula for methanol.
2. Locate the functional group present in methanol on the structural formula above. Name the functional group. 
3. At 25^oC methanol has a density of  0.79 g mL^-3. Calculate the mass of methanol present in a lethal dose of pure methanol .
4.  Convert the concentration of methanol given for homemade whiskey into a concentration in g mL^-1.
5. Assume the young man who died drank homemade whiskey. What minimum volume of homemade whiskey did he drink?
6. For galacturonic acid given the:
   • molecular formula
   • molar mass
7.  On the structural formula for galacturonic acid identify and name the functional groups present.
8. Draw the structure for the sodium salt of galacturonic acid.
9. Draw the structure for galacturonic acid esterified with methanol.
10. Give the molecular formula and molar mass for the structure above.
11. Apples contain about 1% by mass pectin. 10 kg of apples are to be used in the production of a homemade liquor. What mass of pectin will be present?
12. Assume exactly 100% of the carboxyl groups in galacturonic acid are esterified with methanol. How many moles of the ester are present in 10 kg of apples?
13. Write an equation representing the reaction between this ester and water to form methanol  and galacturonic acid.
14. How many moles of methanol could be produced by the break down of pectin in 10 kg of apples?
15. Assuming the young man who died had drunk this apple concoction without distilling and removing the methanol, what minimum volume of fermented apple-drink would he have had to have drunk?
16. Why do you think most countries have outlawed home-distilling?

AUS-e-NEWS June 2013

Have you ever noticed that the price of E10 fuel, also known as gasohol, is less than the price of petrol (gasoline) ?

Just today, when I went to put fuel into my car, the price for standard unleaded petrol (ULP) was 130.6 cents per litre while the price of E10 fuel was 128.4 cents per litre.

Will using E10 instead of ULP save me money?

Read the June 2013 edition of AUS-e-NEWS to find out!

Haven't received your newsletter?

Email AUS-e-TUTE: 

New AUS-e-TUTE Resources

AUS-e-TUTE has just added new resources on the strength of conjugate acids and bases, as well as proton-transfer reactions.

The new resources will be found under the Acids and Bases Topic Heading.

http://www.ausetute.com.au

An Itchy Polypeptide

Scientists have a discovered that a small molecule, natriuretic polypeptide b (Nppb), is responsible for that itchy feeling in mice. When natriuretic polypeptide b is removed, and mice are exposed to itch-inducing substances, nothing happens! No itching! The nervous systems of mice and humans are similar, so the scientists believe that the same molecule is probably responsible for making you feel itchy.

Natriuretic polypeptide b  is a polypeptide made up of 32 amino acid residues as shown below:

 The amino acid residues in order of appearance are:

amino acid name	structure
serine
proline
lysine
methionine
valine
glutamine
glycine
cysteine
phenylalanine
arginine
aspartic acid
isoleucine
leucine
histidine

This research could be of enormous benefit to people who suffer from chronic itch conditions like eczema and psoriasis. Unfortunately, natriuretic polypeptide b is also used in other body processes in the heart and kidneys, so its removal in humans could cause major problems.

Reference:
S. K. Mishra, M. A. Hoon. The Cells and Circuitry for Itch Responses in Mice. Science, 2013; 340 (6135): 968 DOI: 10.1126/science.1233765

Further Reading:
Amino Acids 
Proteins 

Suggested Study Questions:

1.  What is meant by the term polypeptide?
2. Refer the structure of natriuretic polypeptide b. Draw up a table giving the name and the number of each amino acid present in each molecule of natriuretic polypeptide b.
3. What two functional groups are common to all amino acids?
4. On the structure of alanine shown below, label each of the functional groups:
   
   
5. What type of bond holds the amino acids together in the chain of natriuretic polypeptide b ?
6.  Using two molecules of serine, show how they are joined together to form a dipeptide.
7. What is the name given to the type of chemical reaction in which two serine molecules combine to form a dipeptide?
8. Name the type of bond shown between two cysteines on the structure of natriuretic polypeptide b shown above.
9. What is the primary structure of natriuretic polypeptide b ?
10. How would you describe the secondary structure of natriuretic polypeptide b ?   

Astatine's Ionization Energy

Astatine is the product of the radioactive decay of some heavier elements and is the rarest naturally occurring element on Earth, only a few grams of astatine is estimated be present in the whole of the Earth's crust at any one time. All of astatine's isotopes are short-lived, with astatine-210 having the longest half-life of all its isotopes, 8.1 hours. As a result, astatine was unknown until 1940, when scientists bombarded bismuth-209 with alpha particles and produced astatine.
Even today we don't know very much about astatine, but estimates about its properties have been made based on its position in the Periodic Table, right under iodine in Group 17 (halogens). The first ionization energy of astatine has been estimated to be between 849.11 and 926.29 kJ/mol (8.8 and 9.6 eV).

The ionization energy, the energy required to remove an electron from the valence shell of an atom, is one of the most important properties that influences the chemical behaviour of an element.

In May 2013 an international team of researchers announced that they had measured the first ionization energy of astatine using laser ionization spectroscopy and found it be be 9.31751 eV (899.02 kJ/mol)

Reference:
Rothe, S. et al. Measurement of the first ionization potential of astatine by laser ionization spectroscopy. Nat. Commun. 4:1835 doi: 10.1038/ncomms2819 (2013).

Further Reading:
http://www.ausetute.com.au/pertable.html

http://www.ausetute.com.au/trendgp7.html 
http://www.ausetute.com.au/trendie.html 
http://www.ausetute.com.au/isotopes.html
http://www.ausetute.com.au/nucledec.html
http://www.ausetute.com.au/halflife.html

Suggested Study Questions:

1. Use the Periodic Table to find the following:
   • astatine's chemical symbol
   • astatine's atomic number
2.  Use the Periodic Table to find the
   • The group astatine belongs to
   • the period astatine belongs to
3. How many valence electrons does an atom of astatine have? Explain your answer.
4. Describe the trend in melting points as you go down astatine's group in the periodic table, then estimate the melting point of astatine.
5. Describe what you think astatine would look like at room temperature and justify your answer on the basis of trends in the periodic table. 
6. How does astatine-207 differ from astatine-210? 
7. Astatine-211 and 2 neutrons are produced when bismuth-209 is bombarded with alpha particles.  Write a nuclear equation for this reaction.
8. Imagine working in a laboratory. You have been given 100 μg of astatine-210 at 9 am for your experiment. Assuming the half-life of astatine is 8 hours, how much astatine-210 would you have left when you leave the lab at 5 pm?
9. The half-life of astatine-219 is about 1 minute. If you had 100 μg of astatine-219 at 9 am, how much astatine-219 would you have 5 minutes later at 9:05 am ?
10. Use the information in the article above to estimate the conversion factor between electronvolts (eV) and kJ/mol. 
11. Why do we not have an accurate measure of how much astatine is found in the Earth's crust?
12. Suggest a way that scientists can estimate the amount of astatine in existence in the Earth's crust.  

AUS-e-TUTE Update

The following resources have been added to AUS-e-TUTE:

• Neutralisation Reactions (tutorial, game, test)
• Acidic, Basic, Neutral Solutions (tutorial, game, test)
• Properties of Alkanes (tutorial, game, test, exam)
• Properties of Alkanols (alcohols) (tutorial, game, test, exam)
• Properties of Alkanoic (carboxylic) acids (tutorial, game, test, exam)
• Properties of Amines (tutorial, game, test, exam)

Syllabus Study Guides have also been updated.

Ancient Elements

Only about a dozen elements were known to the people living in ancient civilizations.

• Copper beads dating from about 6000 B.C. have been found in Turkey.

• A lead statuette found in an Egyptian temple dates from around 3800 B.C. and golden artefacts have also been found in ancient Egyptian tombs.

• Silver was used by the ancient Greeks and Romans to prevent infection, and was used as an early form of currency.

• There is evidence of the systematic production of iron in Turkey around 2000 B.C. for use in tools and weapons.

• Carbon, in the form of diamonds, was also known in the Ancient world, but, carbon in the form of charcoal was far more important to these early people because it could be used in the production of copper, tin, and therefore bronze (an alloy of copper and tin).

• Sulfur was also known to the Ancient Egyptians and Greeks, who used it as a medicine.

• The ancient Chinese, Indians and Egyptians also knew about mercury, using it in ointments and cosmetics.

• Before 1000 B.C., Indians were extracting zinc from its ores. Ornaments containing 80% or more of zinc have been found.

• During the Bronze Age (an earlier period than the Iron Age), arsenic was included in bronze to make the alloy harder. Ancient people understood that they could produce arsenic by heating certain substances (which we would now call arsenic sulfides and oxides).

• Antimony was used in cosmetics in the Ancient world, notably by the Egyptians who used it around their eyes (known as kohl).

• Chromium has been found in ancient Chinese artifacts. The weapons the Chinese Terracotta Army carry are coated in chromium oxide and date from around the 3rd century B.C.

In fact, these were really the only elements known  until the 17th century A.D.
Today we know of over a 100 elements.
Chemistry has come a long way in the last few hundred years!

Further Reading:
History of the Elements
Metal Extraction Concepts
Periodic Table
Metals and Non-metals
Pure Substances and Mixtures

Suggested Study Questions:

1.  Find each of the elements mentioned above on the Periodic Table.
2. Draw up a table of the name and chemical symbol for each of the elements mentioned above.
3. Draw up a table classifying each of these elements as metals, non-metals or semi-metals (metalloids).
4. Name a mixture mentioned in the article above.
5. Name a compound mentioned in the article above.
6. There are only 3 metallic elements that are not a "silvery" colour. One of these is cesium (or caesium), but if the sample of cesium is very pure it loses its golden colour. Name the other two non-silvery metallic elements.
7. Explain why you often find weapons like swords made of iron, but you never find functional weapons made of gold.
8. Explain why you find ornamental weapons made out of gold, but rarely out of zinc.
9. Ancient people could have produced mercury by heating cinnabar (mercury(II) sulfide). The cinnabar decomposes, producing liquid mercury and sulfur. Write a word equation for the decomposition of cinnabar.