Acetone

Raw materials

1. Benzene

2. Propylene

Process
Cumene porcess

1. Benzene and propylene are compressed together to a pressure of 30 atm at 250 °C in presence of a catalytic Lewis acid (phosphoric acid). Cumene is formed in the gas-phase Friedel-Crafts alkylation of benzene by propylene.

2. Cumene is oxidized in air which removes the tertiary benzylic hydrogen from cumene and hence forms a cumene radical.

3. This cumene radical then bonds with an oxygen molecule to give cumene hydroperoxide radical, which in turn forms cumene hydroperoxide by abstracting benzylic hydrogen from another cumene molecule. This latter cumene converts into cumene radical and feeds back into subsequent chain formations of cumene hydroperoxides. A pressure of 5 atm is used to ensure that the unstable peroxide is kept in liquid state.

4. Cumene hydroperoxide is then hydrolysed in an acidic medium (the Hock rearrangement) to give phenol and acetone acetone. In the first step, the terminal hydroperoxy oxygen atom is protonated. This is followed by a step in which the phenyl group migrates from the benzyl carbon to the adjacent oxygen and a water molecule is lost, producing a resonance stabilized tertiary carbocation. The concerted mechanism of this step is similar to the mechanisms of the Bayer-villiger oxidation and also the oxidation step of hydroboration-oxidation. In 2009, a acidified bentonite clay was proven to be a more economical catalyst than sulfuric acid as the acid medium.

As shown below, the resulting carbocation is then attacked by water, a proton is then transferred from the hydroxy oxygen to the ether oxygen, and finally the ion falls apart into phenol and acetone.

5. The products are extracted by distillation.

Product

Acetone

Used as

Nail polish remover, paint remover

Production facility

Whyalla, SA

Export

Sofia, Bulgaria

Acetic acid

Raw materials

1. Methanol

2. Carbon moxide

Process

Methanol carbonylation 

(Most acetic acid is produced by methanol carbonylation.)

Methanol and carbon monoxide are reacted to produce acetic acid according to the chemical equation:

CH₃OH + CO → CH₃COOH

The process involves iodomethane as an intermediate, and occurs in three steps. A catalyst, usually a metal complex, is needed for the carbonylation (step 2).

1. CH₃OH + HI → CH₃I + H₂O
2. CH₃I + CO → CH₃COI
3. CH₃COI + H₂O → CH₃COOH + HI

Product

Acetic acid

Used in

Vinyl acetate monomer (can be polymerized to polyvinyl acetate or to other polymers, which are applied in paint and adhesives), ester production (for inks, paints, and coatings), vinegar

Production facility

Bundaberg, QLD

Export

Ouagadougou, Burkina Faso

Hydrochloric acid

Raw materials

1. Hydrogen chloride

2. Water

Process

Hydrochloric acid is prepared by dissolving hydrogen chloride in water.

Product

Hydrochloric acid

Used for

Pickling of steel, production of organic and inorganic compounds, pH control, neutralization, regeneration of ion exchangers, leather processing, purification of common salt, household cleaning

Production facility

Victor Harbor, SA

Export

Bandar Seri Begawan, Brunei

Ammonia

Raw materials

1.Nitrogen

2. Hydrogen

Process

Harber Process

Nitrogen from the air is combined with hydrogen derived mainly from natural gas (methane) with the presence of iron catalyst to produce ammonia. The reaction is reversible and the production of ammonia is exothermic.

N₂ (g) + 3 H₂ (g) ⇌ 2 NH₃ (g)   (ΔH = −92.22 kJ·mol⁻¹)

Product

Ammonia

Used in

Fertilizer, precursor to nitrogenous compounds (virtually all synthetic nitrogen compounds are derived from ammonia), cleaners (clean glass, porcelain and stainless steel; cleaning ovens; soaking items to loosen baked-on grime), fermentation (as a source of nitrogen for microorganisms and to adjust pH during fermentation), plastics, fibers, explosives, intermediates for dyes and pharmaceuticals.

Production facility

Burrup Peninsula, WA

Export

Brasilia, Brazil

Nitric acid

Raw materials

1. Ammonia

2. Oxygen

Process

Ostwald Process

Ammonia is converted to nitric acid in two stages.

1. Ammonia is oxidized by heating with oxygen in the presence of a catalyst such as platinum with 10% rhodium to form nitric oxide and water with typical conditions of (which contribute to an overall yield of about 96%) pressure between 4-10 atm and temperature of 900 °C. This step is strongly exothermic, making it a useful heat source once initiated:

4 NH₃ (g) + 5 O₂ (g) → 4 NO (g) + 6 H₂O (g) (ΔH = −905.2 kJ)

2. Stage two (combining two reaction steps) is carried out in the presence of water in an absorption apparatus. Initially nitric oxide is oxidized again to yield nitrogen dioxide:

2 NO (g) + O₂ (g) → 2 NO₂ (g) (ΔH = −114 kJ/mol)

This gas is then readily absorbed by the water, yielding the desired product (nitric acid, albeit in a dilute form), while reducing a portion of it back to nitric oxide:

3 NO₂ (g) + H₂O (l) → 2 HNO₃ (aq) + NO (g) (ΔH = −117 kJ/mol)

The NO is recycled, and the acid is concentrated to the required strength by distillation.

Product

Nitric acid

Used for

Rocket fuel, chemical reagent, woodworking (artificially age pine and maple)

Production facility

Port Lincoln, SA

Export

Gaborone, Botswana

Nitrogen dioxide

Raw material

1. Nitric acid

Process

Nitrogen dioxide, NO₂ is prepared in a two step procedure by thermal decomposition of dinitrogen pentoxide, which is obtained by dehydration of nitric acid:

2 HNO₃ → N₂O₅ + H₂O

2 N₂O₅ → 4 NO₂ + O₂

Product

Nitrogen dioxide

Used as

Catalyst in certain oxidation reactions, inhibitor to prevent polymerization of acrylates during distillation, nitrating agent for organic compounds, oxidizing agent, rocket fuel, flour bleaching agent, increasing the wet strength of paper

Production facility

Port Pirie, SA

Export

Sarajevo, Bosnia and Herzegovina

Sulfuric acid

Raw materials

1. Sulfur

2. Oxygen

3. Water

Process

a. Contact Process (DCDA)

1. Sulfur burned to produce sulfur dioxide.

S (s) + O₂ (g) → SO₂ (g)

2. The sulfur dioxide is oxidized to sulfur trioxide using oxygen in the presence of vanadium(V)oxide catalyst.

2 SO₂ (g) + O₂ (g) → 2 SO₃ (g) (in presence of V₂O₅)

3. Sulfur trioxide is absorbed into 97–98% H₂SO₄ to form oleum (H₂S₂O₇), also known as fuming sulfuric acid. The oleum is then diluted with water to form concentrated sulfuric acid.

H₂SO₄ (l) + SO₃ → H₂S₂O₇ (l)

H₂S₂O₇ (l) + H₂O (l) → 2 H₂SO₄ (l)

(Note that directly dissolving SO₃ in water, SO₃ (g) + H₂O (l) → H₂SO₄ (l), is not practical due to the highly exothermic nature of the reaction between sulfur trioxide and water. The reaction forms a corrosive aerosol that is very difficult to separate, instead of a liquid.)

b. Wet sulfuric acid process (WSA)

1. Sulfur burned to produce sulfur dioxide.

S(s) + O₂(g) → SO₂(g)

or, alternatively, hydrogen sulfide (H₂S) gas is incinerated to SO₂ gas.

2 H₂S + 3 O₂ → 2 H₂O + 2 SO₂ (−518 kJ/mol)

2. The sulfur dioxide is oxidized to sulfur trioxide using oxygen with vanadium(V)oxide catalyst.

2 SO₂ + O₂ → 2 SO₃ (−99 kJ/mol) (reaction is reversible)

3. The sulfur trioxide is hydrated into sulfuric acid H₂SO₄.

SO₃ + H₂O → H₂SO₄(g) (−101 kJ/mol)

4. The sulfuric acid is condensed to liquid 97–98% H₂SO₄.

H₂SO₄(g) → H₂SO₄(l) (−69 kJ/mol)

Product

Sulfuric acid

Used in

Lead-acid batteries (for cars and other vehicles), ore processing, fertilizer manufacturing, oil refining, wastewater processing, chemical synthesis

Production facility

Port Augusta, SA

Export

Sucre, Bolivia