Less waste, safer chemicals

Section 1 of 4

Every reaction turns starting materials into products. Green chemistry is the work of doing that with less waste, less energy and safer chemicals.

A factory pays for every atom it buys. Atoms that end up in the product are sold, and atoms that end up anywhere else become waste to be cleaned up and thrown away. In 1998 the chemists Paul Anastas and John Warner set out twelve principles of green chemistry. The first one is that the best waste to deal with is waste that is never made.

Atom economy

Atom economy measures how many of the starting atoms end up in the product you want. Work it out from the balanced equation: the mass of the wanted product, divided by the mass of everything that reacts, times 100.

An addition reaction puts everything together, so its atom economy is 100%. Ethene and water join into ethanol, the addition across a C=C you met earlier, and every atom of both ends up in the ethanol. Factories make ethanol this way at about 300 °C, with phosphoric acid as a catalyst.

Ethene, C₂H₄Two carbon atoms joined by a double bond, each also bonded to two hydrogen atoms.HHCCHH plus Water, H₂OOne oxygen atom joined by single bonds to two hydrogen atoms, in a bent shape.OHH
make
Ethanol, C₂H₅OHTwo carbon atoms in a chain; the second carbon is bonded to an oxygen atom that carries a hydrogen atom, an -OH group.HHHCCOHHH
Ethene and water make ethanol: C₂H₄ + H₂O → C₂H₅OH. The water adds across the double bond, so 28 g of ethene and 18 g of water make 46 g of ethanol.

Yeast makes ethanol too, by fermenting glucose: C₆H₁₂O₆ → 2 C₂H₅OH + 2 CO₂. Carbon dioxide is given off as a by-product, so only part of the glucose ends up as ethanol. Using masses from C = 12, H = 1 and O = 16, 180 g of glucose makes 92 g of ethanol and 88 g of carbon dioxide. The atom economy is 92 ÷ 180 × 100, about 51%.

Atom economy of two ways to make ethanol Two bars, each standing for all the atoms that go into a reaction. Top: ethene and water make ethanol, and the whole bar is ethanol, 46 grams from 46 grams: an atom economy of 100%. Bottom: glucose ferments into ethanol and carbon dioxide. Of 180 grams of glucose, 92 grams end up as ethanol and 88 grams as carbon dioxide, so the ethanol part of the bar is about half: an atom economy of 51%. ethene + water → ethanol 100% ethanol: all 46 g glucose → ethanol + carbon dioxide 51% ethanol 92 g carbon dioxide 88 g
Each bar is all the atoms that react. Adding water to ethene puts every atom into ethanol. Fermenting glucose puts about half of them into ethanol, and the rest leave as carbon dioxide.

Atom economy comes from the equation alone. The yield chemists measure when they make a molecule is a different measure: how much product a real batch gave, out of the most it could give. A reaction with a 100% yield still makes waste when its equation has a by-product, and a reaction with a 100% atom economy still makes waste when its yield is low.

Kilograms of waste made for each kilogram of product, about
IndustryWaste per kg
oil refiningless than 0.1 kg
bulk chemicalsunder 1 to 5 kg
fine chemicals5 to more than 50 kg
medicines25 to more than 100 kg

Quick check

Ethanoic acid (60 g) and ethanol (46 g) join into ethyl ethanoate (88 g) and water (18 g). What is the atom economy for making ethyl ethanoate?