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11.6 Alcohols

11.6.1 Ethanol: manufacture, combustion and uses

Fermentation

Definition

Fermentation

The conversion of aqueous glucose into ethanol and carbon dioxide by enzymes in yeast in the absence of oxygen.

  1. Ethanol, C2H5OH\text{C}_2\text{H}_5\text{OH}C2​H5​OH, is made on a large scale by two different methods: fermentation of glucose and catalytic addition of steam to ethene.

  2. Fermentation starts with aqueous glucose, which is glucose dissolved in water, usually obtained from sugar-rich crops such as sugar cane or sugar beet.

  3. Yeast is added to the glucose solution, because yeast cells contain enzymes that catalyse the breakdown of glucose.

  4. Three conditions are needed for fermentation.

    1. Yeast must be present to supply the enzymes.
    2. The temperature is kept between 25 ∘C25\ ^\circ\text{C}25 ∘C and 35 ∘C35\ ^\circ\text{C}35 ∘C.
    3. Oxygen is kept out, so the process is anaerobic.
  5. Below 25 ∘C25\ ^\circ\text{C}25 ∘C the enzymes work slowly, so fermentation takes much longer.

  6. Above about 35 ∘C35\ ^\circ\text{C}35 ∘C the enzymes start to become denatured, so the rate falls and fermentation stops.

  7. Oxygen must be excluded because, with air present, the yeast respires aerobically to make carbon dioxide and water instead of ethanol, and bacteria can oxidise the ethanol that has formed.

  8. The fermentation vessel is fitted with an airlock, which lets carbon dioxide escape but stops air getting in.

  9. Glucose is broken down into ethanol and carbon dioxide.

    glucose→ethanol+carbon dioxide \text{glucose} \rightarrow \text{ethanol} + \text{carbon dioxide} glucose→ethanol+carbon dioxide
  10. The balanced symbol equation shows that one glucose molecule gives two ethanol molecules and two carbon dioxide molecules.

    C6H12O6(aq)→2C2H5OH(aq)+2CO2(g) \text{C}_6\text{H}_{12}\text{O}_6\text{(aq)} \rightarrow 2\text{C}_2\text{H}_5\text{OH(aq)} + 2\text{CO}_2\text{(g)} C6​H12​O6​(aq)→2C2​H5​OH(aq)+2CO2​(g)
  11. Fermentation is slow and takes several days, with bubbles of carbon dioxide given off the whole time.

  12. Fermentation stops when the glucose is used up or when the ethanol concentration reaches about 15%15\%15%, because ethanol at this concentration kills the yeast.

  13. The product is a dilute aqueous solution of ethanol, so the yeast is removed by filtration and the ethanol is separated from the water by fractional distillation.

Example

Balancing the fermentation equation

  • Glucose, C6H12O6\text{C}_6\text{H}_{12}\text{O}_6C6​H12​O6​, is the only reactant, and the products are ethanol, C2H5OH\text{C}_2\text{H}_5\text{OH}C2​H5​OH, and carbon dioxide, CO2\text{CO}_2CO2​.
C6H12O6→C2H5OH+CO2 \text{C}_6\text{H}_{12}\text{O}_6 \rightarrow \text{C}_2\text{H}_5\text{OH} + \text{CO}_2 C6​H12​O6​→C2​H5​OH+CO2​
  • Glucose has 12 hydrogen atoms and each ethanol molecule has 6, so 2 ethanol molecules are needed.
  • Two ethanol molecules hold 4 carbon atoms, so the remaining 2 carbon atoms go into 2 carbon dioxide molecules.
C6H12O6→2C2H5OH+2CO2 \text{C}_6\text{H}_{12}\text{O}_6 \rightarrow 2\text{C}_2\text{H}_5\text{OH} + 2\text{CO}_2 C6​H12​O6​→2C2​H5​OH+2CO2​
  • Checking oxygen, the left side has 6 atoms and the right side has 2+4=62 + 4 = 62+4=6 atoms, so the equation is balanced.
Practical

Fermenting a glucose solution

  • Aim: to make ethanol by fermenting aqueous glucose with yeast and to identify the gas given off.
  • Apparatus: 250 cm3250\ \text{cm}^3250 cm3 conical flask, 10 g10\ \text{g}10 g of glucose, 100 cm3100\ \text{cm}^3100 cm3 measuring cylinder, warm water, 1 g1\ \text{g}1 g of dried yeast, bung fitted with a delivery tube, boiling tube of limewater, thermostatically controlled water bath set to 30 ∘C30\ ^\circ\text{C}30 ∘C, filter funnel and filter paper, and eye protection.
  • Method:
    • Dissolve 10 g10\ \text{g}10 g of glucose in 100 cm3100\ \text{cm}^3100 cm3 of warm water in the conical flask and swirl until no solid remains.
    • Stir in 1 g1\ \text{g}1 g of dried yeast.
    • Fit the bung and delivery tube so that the end of the tube dips into limewater, which lets gas out but keeps air away from the mixture.
    • Stand the flask in the water bath at 30 ∘C30\ ^\circ\text{C}30 ∘C and leave it for several days.
    • When bubbling stops, filter the mixture to remove the yeast and keep the filtrate for fractional distillation.
  • Results:
    • Within about half an hour, bubbles rise steadily through the mixture and a froth forms on the surface.
    • The limewater turns milky, showing that the gas is carbon dioxide.
    • The filtrate smells of alcohol, and bubbling slows and stops after a few days.
  • Conclusion: yeast ferments glucose into ethanol and carbon dioxide when it is kept warm and away from oxygen.
  • Safety: wear eye protection, keep the ethanol-containing filtrate away from naked flames because ethanol is flammable, and never taste the product.

Steam addition to ethene

Definition

Catalyst

A substance that increases the rate of a reaction and is chemically unchanged at the end of the reaction.

  1. The second method reacts ethene, C2H4\text{C}_2\text{H}_4C2​H4​, with steam, H2O\text{H}_2\text{O}H2​O, to make ethanol.

  2. The ethene comes from cracking large alkane molecules obtained from petroleum.

  3. Three conditions are used for this reaction.

    1. A temperature of about 300 ∘C300\ ^\circ\text{C}300 ∘C.
    2. A pressure of about 6000 kPa6000\ \text{kPa}6000 kPa, which is the same as 60 atm60\ \text{atm}60 atm.
    3. An acid catalyst, usually phosphoric acid.
  4. Steam adds across the C=C\text{C=C}C=C double bond, so ethene and steam join together to form ethanol as the only product.

    ethene+steam→ethanol \text{ethene} + \text{steam} \rightarrow \text{ethanol} ethene+steam→ethanol
  5. The balanced symbol equation is shown below.

    C2H4(g)+H2O(g)→C2H5OH(g) \text{C}_2\text{H}_4\text{(g)} + \text{H}_2\text{O(g)} \rightarrow \text{C}_2\text{H}_5\text{OH(g)} C2​H4​(g)+H2​O(g)→C2​H5​OH(g)
  6. The reaction is reversible, so only a small fraction of the ethene reacts each time the gases pass over the catalyst.

  7. The ethanol is condensed by cooling, and the unreacted ethene and steam are recycled back through the reactor.

  8. The process runs continuously, with fresh ethene and steam fed in while ethanol is removed.

Combustion of ethanol

  1. Ethanol is a flammable liquid that burns readily in air with a pale blue flame.

  2. Combustion is exothermic, so burning ethanol releases a large amount of thermal energy.

  3. In a plentiful supply of oxygen, ethanol undergoes complete combustion to form carbon dioxide and water only.

    ethanol+oxygen→carbon dioxide+water \text{ethanol} + \text{oxygen} \rightarrow \text{carbon dioxide} + \text{water} ethanol+oxygen→carbon dioxide+water
  4. Each ethanol molecule needs three oxygen molecules for complete combustion.

    C2H5OH(l)+3O2(g)→2CO2(g)+3H2O(l) \text{C}_2\text{H}_5\text{OH(l)} + 3\text{O}_2\text{(g)} \rightarrow 2\text{CO}_2\text{(g)} + 3\text{H}_2\text{O(l)} C2​H5​OH(l)+3O2​(g)→2CO2​(g)+3H2​O(l)
  5. Ethanol already contains an oxygen atom in its molecule, so it needs less oxygen from the air than a hydrocarbon with the same number of carbon atoms.

  6. Ethanol burns with a clean flame that produces very little soot.

  7. In a limited supply of oxygen, incomplete combustion can also produce toxic carbon monoxide.

Example

Balancing the combustion of ethanol

  • Start with the unbalanced equation for complete combustion.
C2H5OH+O2→CO2+H2O \text{C}_2\text{H}_5\text{OH} + \text{O}_2 \rightarrow \text{CO}_2 + \text{H}_2\text{O} C2​H5​OH+O2​→CO2​+H2​O
  • Ethanol has 2 carbon atoms, so 2 carbon dioxide molecules are formed.
  • Ethanol has 6 hydrogen atoms, so 3 water molecules are formed.
  • The products now contain (2×2)+3=7(2 \times 2) + 3 = 7(2×2)+3=7 oxygen atoms.
  • Ethanol supplies 1 of these oxygen atoms, so the other 6 come from 3 oxygen molecules.
C2H5OH+3O2→2CO2+3H2O \text{C}_2\text{H}_5\text{OH} + 3\text{O}_2 \rightarrow 2\text{CO}_2 + 3\text{H}_2\text{O} C2​H5​OH+3O2​→2CO2​+3H2​O

Uses of ethanol

  1. Ethanol as a solvent
    1. Ethanol dissolves many substances that are insoluble in water, such as oils, resins and many dyes.
    2. Ethanol also mixes with water, so it can carry both kinds of substance in one solution.
    3. Ethanol evaporates quickly at room temperature, so it leaves a surface dry soon after it is applied.
    4. These properties make ethanol a common solvent in perfumes, aftershaves, medicines, inks, varnishes and hand sanitisers.
  2. Ethanol as a fuel
    1. Ethanol burns easily and releases a large amount of thermal energy, so it is a useful fuel.
    2. Complete combustion gives only carbon dioxide and water, and the clean flame produces little soot.
    3. Ethanol is mixed with petrol to fuel cars, and it is used on its own in some vehicles, in spirit burners and in camping stoves.
Common Mistake
  • Do not give a fermentation temperature above 35 ∘C35\ ^\circ\text{C}35 ∘C, because the enzymes in the yeast are denatured at higher temperatures.
  • Do not leave carbon dioxide out of the products of fermentation, because two molecules form for every glucose molecule.
  • Do not mix up the raw materials, because fermentation uses glucose while the catalytic process uses ethene and steam.
  • Do not write "no air" for steam addition, because the absence of oxygen is a condition for fermentation only.
Exam technique

Stating conditions and equations

  • When asked for the conditions for fermentation, give all three: yeast, a temperature of 25–35 ∘C25\text{–}35\ ^\circ\text{C}25–35 ∘C, and absence of oxygen or anaerobic.
  • When asked for the conditions for steam addition, give 300 ∘C300\ ^\circ\text{C}300 ∘C, 6000 kPa6000\ \text{kPa}6000 kPa or 60 atm60\ \text{atm}60 atm, and an acid catalyst, always with units.
  • Write "aqueous glucose" rather than "sugar" when describing the starting material for fermentation.
  • Check that the combustion equation has 3 oxygen molecules, 2 carbon dioxide molecules and 3 water molecules before moving on.
  • For a use of ethanol, name the use and give its reason, such as "a fuel because it releases a lot of energy when it burns".
Self review
  • What three conditions are needed to make ethanol by fermentation?
  • Why does fermentation slow down and stop above about 35 ∘C35\ ^\circ\text{C}35 ∘C?
  • What temperature, pressure and catalyst are used to add steam to ethene?
  • Write the balanced equation for the complete combustion of ethanol.
  • Give two uses of ethanol.

11.6.2 Comparing methods of making ethanol

Fermentation

Definition

Renewable resource

A resource that can be replaced, for example by growing more crops, as quickly as it is used up.

Definition

Batch process

A manufacturing process in which a fixed amount of product is made at one time, after which the vessel is emptied before the next batch is started.

  1. Fermentation makes ethanol from aqueous glucose using yeast, at 25–35 ∘C25\text{–}35\ ^\circ\text{C}25–35 ∘C and in the absence of oxygen.
  2. Advantages of fermentation
    1. The glucose comes from crops such as sugar cane and sugar beet, which can be grown again every year, so the raw material is renewable.
    2. The low temperature and normal atmospheric pressure mean that little energy is needed to keep the reaction going.
    3. The equipment is simple and cheap, because the tanks do not have to withstand high temperatures or pressures.
    4. Fermentation does not depend on supplies of petroleum, so it suits countries that grow large amounts of sugar crops but have little crude oil.
  3. Disadvantages of fermentation
    1. Fermentation is slow, taking several days to make each batch of ethanol.
    2. It is a batch process, so the vessel has to be emptied, cleaned and refilled between batches, which wastes time.
    3. The product is a dilute solution, because the yeast dies when the ethanol concentration reaches about 15%15\%15%.
    4. The ethanol is impure, mixed with water, yeast and unused glucose, so it must be filtered and then purified by fractional distillation, which needs extra energy.
    5. Carbon dioxide forms alongside the ethanol, so not all of the atoms in the glucose end up in the useful product.
    6. Growing the crops needs large areas of land, which could otherwise be used to grow food.

Steam addition to ethene

Definition

Continuous process

A manufacturing process that runs without stopping, with reactants fed in and products removed all the time.

  1. Catalytic addition of steam to ethene makes ethanol at about 300 ∘C300\ ^\circ\text{C}300 ∘C and 6000 kPa6000\ \text{kPa}6000 kPa, using an acid catalyst.
  2. Advantages of steam addition
    1. The reaction is fast, so a large amount of ethanol is made in a short time.
    2. It is a continuous process, so ethanol is produced all the time without stopping to empty and refill the reactor.
    3. Ethanol is the only product, so all the atoms of the reactants end up in the ethanol and there is no waste product.
    4. The product is pure ethanol, so it does not need the long purification that fermentation needs.
    5. Unreacted ethene and steam are recycled, so a high overall yield is obtained.
  3. Disadvantages of steam addition
    1. The ethene is made by cracking fractions from petroleum, which is non-renewable and will eventually run out.
    2. The high temperature and high pressure need a lot of energy, which is often obtained by burning fossil fuels.
    3. The reactor and pipes must be strong enough to withstand 6000 kPa6000\ \text{kPa}6000 kPa, so the plant is expensive to build and maintain.
    4. The reaction is reversible, so only a small fraction of the ethene is converted on each pass and the gases must be separated and recycled.

Comparing the two methods

  1. Raw material
    1. Fermentation uses glucose from crops, which is renewable.
    2. Steam addition uses ethene from petroleum, which is non-renewable.
  2. Rate of production
    1. Fermentation is slow, while steam addition is fast.
  3. Type of process
    1. Fermentation is a batch process, while steam addition is a continuous process.
  4. Purity of the product
    1. Fermentation gives a dilute, impure solution that needs fractional distillation, while steam addition gives pure ethanol.
  5. Energy and conditions
    1. Fermentation uses a low temperature and atmospheric pressure, so its energy needs are low.
    2. Steam addition uses a high temperature and high pressure, so its energy needs are high.
  6. Equipment and cost
    1. Fermentation tanks are cheap, while a high-pressure steam addition plant is expensive.
  7. Products formed
    1. Fermentation also produces carbon dioxide, while steam addition produces ethanol only.
  8. The best method for a country depends on whether it has more farmland and sugar crops or more petroleum and money for an industrial plant.
Example

Choosing a method for two countries

  • Country A grows large amounts of sugar cane and has no petroleum reserves.
    • Fermentation suits Country A, because its raw material is cheap, local and renewable.
    • Low-cost tanks and low energy needs also keep the cost of setting up the process down.
  • Country B has large petroleum reserves, a cracking industry and high demand for pure ethanol.
    • Steam addition suits Country B, because ethene is readily available from cracking.
    • The fast, continuous process gives pure ethanol in large amounts, which repays the high cost of the plant.
Common Mistake
  • Do not write only "fermentation is cheaper", because the mark is for the reason, such as low energy use or simple equipment.
  • Do not describe ethene as renewable, because it is made from petroleum.
  • Do not claim that steam addition needs no energy input, because high temperature and pressure need large amounts of energy.
  • Do not forget that fermentation gives an impure product that has to be purified by fractional distillation.
Exam technique

Writing comparison answers

  • Write each point as a comparison, such as "fermentation is slower than steam addition", rather than describing only one method.
  • When you say a raw material is renewable or non-renewable, name it, such as "glucose from sugar cane" or "ethene from petroleum".
  • Use the key terms batch and continuous when comparing how the two processes run.
  • Link each advantage or disadvantage to its reason, such as "high pressure needs a lot of energy".
  • If a question asks for one advantage and one disadvantage of a method, give one of each and do not list extra points that might contradict them.
Self review
  • Why is the raw material for fermentation described as renewable?
  • Give two disadvantages of making ethanol by fermentation.
  • What is the difference between a batch process and a continuous process?
  • Give two advantages of making ethanol by the catalytic addition of steam to ethene.
  • Why does steam addition need a large amount of energy?

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Displayed formula of ethanol with the -OH functional group highlighted and arrows showing fermentation of glucose and hydration of ethene as two routes to ethanol

Alcohols are organic compounds that contain the -OH functional group. The main IGCSE example is ethanol, which can be written as C2H5OHC_2H_5OHC2​H5​OH or CH3CH2OHCH_3CH_2OHCH3​CH2​OH.

The ending "-ol" tells you the compound is an alcohol, and "eth-" shows there are two carbon atoms. The -OH in ethanol is covalently bonded in the molecule, so it is not the same as the hydroxide ion, OH−OH^{-}OH−.

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11.6 Alcohols Revision Guide

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Revision notes for CIE IGCSE Chemistry 11.6 Alcohols: explanations and worked examples on 11.6.1 Ethanol: manufacture, combustion and uses and 11.6.2 Comparing methods of making ethanol.

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