Ethylene Glycol for Antifreeze and Loved Ones

A word inboldindicates that further information can be found in the Glossary. Only the first time the word appears in a chapter will it be so indicated.

Ethylene glycol may be poisonous but it is not a chemical we need worry about, even though we can easily purchase it to use as antifreeze. Indeed, most vehicles contain this chemical and it also has industrial applications. Most of the ethylene glycol that is produced industrially is used to make fibres and plastics. However, it is not entirely without risks, and this sweet-tasting liquid results in many accidental poisonings worldwide every year, especially those involving children who are attracted by its sweet taste. In the USA, there are about 6000 such cases reported annually, of which 20 are fatal. Some desperate individuals resort to drinking this chemical to commit suicide – but it's a slow death. To prevent ethylene glycol from being consumed by children, the bittering agent Bitrex is sometimes added, and in certain states of the USA this is mandatory, such as Oregon where it was introduced as a safety measure in 1991. Sixteen other states also have this requirement.

Sometimes ethylene glycol is used fraudulently. In the 1980s, unscrupulous Austrian vintners added ethylene glycol to cheap wines so they could pass them off as high quality and so charge a higher price. So why were their customers not affected by this chemical? Admittedly the amounts in wine were small, but in any case, the alcohol in the wine was acting as an antidote, something which would-be poisoners may not be aware of, as we shall discover.

Ethylene glycol is not as deadly as some of the other molecules in this book, but it can be used to murder someone if it is done carefully, and would-be murderers can discover its potential as a poison by searching the internet. There are several notable examples of its misuse, although often the intended victim has survived and lived to see their persecutor imprisoned. Sometimes, even seemingly respectable people such as doctors have resorted to using it.

1.1 ETHYLENE GLYCOL

This chemical finds its way directly into our lives in addition to being used as antifreeze. It is to be found in products such as shoe polish, tiling grout, gloss paints, and Tip-Ex correction fluid. It prevents, or stops, these products from drying out too quickly. However, the biggest use of this chemical is in our cars in engine coolants and windscreen washes (Figure 1.1). A typical wash will be 25% antifreeze with 75% water, or even a 50 : 50 mixture for extremely cold conditions when the temperature might fall to as low as -25 °C. Ethylene glycol is also extensively used in cold climates to remove the ice that can accumulate on aircraft wings. However, this has caused local environmental issues because it gets washed on to land or into rivers.

Industrially, ethylene glycol is produced on a massive scale (18 million tonnes a year), most going to make polyethylene terephthalate, aka PET, which is used as a fibre for clothing and as a clear plastic for bottles. PET was discovered in Manchester, England, in 1941 by two chemists Rex Whinfield and James Dickson. They heated ethylene glycol with dimethyl terephthalate at 200 °C and noticed that a sticky material was produced which could be easily drawn into fibres, and that these were strong and unaffected by boiling water. When blended with cotton they produced a fabric which was comfortable to wear, did not crease, and was easy to launder. Polyester and polyester cotton now account for more than 50% of the clothes we buy.

In the 1960s, a new use for PET was found in the form of transparent plastic bottles. They save energy, because they require only 45% of that needed to make a glass bottle and they weigh much less. They save on transport, because a delivery truck can carry 60% more of such containers. And, unlike glass, they do not break into sharp fragments. While most such bottles are sold as non-returnable, it is possible to make them strong enough to be reused. Alternatively, PET bottles can be recycled into different products by being melted down and turned into plastic that is suitable for other types of packaging, or into polyester fibre and turned into such products as carpets, duvets, anoraks, bristles for paint brushes, and felt for tennis balls.

1.2 THE TOXIC NATURE OF ETHYLENE GLYCOL

The body has no use for ethylene glycol and so it changes it chemically as a way of disposing of it, and to do this it attacks it with the enzyme called alcohol dehydrogenase. This first metabolises it to glycolaldehyde, then to glycolic acid, glyoxylic acid, and finally to oxalic acid. These are what make ethylene glycol so dangerous because these acids are rather nasty chemicals which the body must dispose of, but this takes time. The most toxic of these by-products is oxalic acid, and this is the poison discussed in the next chapter.

What constitutes a deadly dose of ethylene glycol for an adult? If this is consumed as a 50 : 50 liquid with water then around 200 mL might well prove fatal. Symptoms of poisoning will begin within an hour or so and will result in vomiting, while the person affected may behave as if they are drunk. Later, more serious changes are occurring in the body as the toxins are produced which affect the heart and the breathing. Then, after a day or two, the kidneys begin to fail and the person may by then be in a coma or have suffered a seizure.

There are antidotes to ethylene glycol and these are alcohol itself (ethanol) or fomepizole, which is rather expensive although it works better. These block the enzymes that are responsible for converting ethylene glycol to the more dangerous toxins. Alcohol as an antidote can be taken in the form of neat gin, vodka or whisky. What the alcohol does is take priority with the enzyme thereby giving the body more time to dispose of the ethylene glycol.

The toxicity of ethylene glycol was unsuspected in the 1930s and this was to have unfortunate consequences in the USA.

The first antibiotic drug, sulfanilamide, was discovered in 1932 by a German chemist, Gerhard Domagk, who worked for IG Farben on new dyes. When he tested sulfanilamide on mice, some of which were infected with deadly streptococci bacteria, they recovered. So he tried it on his sick daughter when she had an infection and she got better almost immediately. This was the first antibiotic, and it was marketed as Prontosil. It was soon being used around the world and Domagk was awarded the Nobel Prize for physiology and medicine in 1939 for his work.

Then, in 1937, an American company, S. E. Massengill, began to produce their version of the new drug, and their chief chemist, Harold Watkins, thought the best way to dispense this medication was as a liquid, which he named Elixir of Sulfanilamide. The solvent he chose was ethylene glycol, and he did this because he found that sulfanilamide was not soluble enough in water to make a useful medicine. However, it was soluble in ethylene glycol and that's how it was dispensed, and to make it more palatable it was flavoured with raspberry extract.

Soon doctors in the USA were prescribing the elixir, but it was not long before they began to report to the American Medical Association that some patients, mostly children, who were given it died unexpectedly. There was a product re-call but not before 107 had died, and then it fell to a Dr Frances Kelsey to research the problem. She discovered that it was not the drug which was causing these deaths but the ethylene glycol. The end result was a change in the law regarding testing, and to this day, the US Food and Drug Administration (FDA) has to approve all such products before they can be prescribed. The man responsible for the deadly medicine was Harold Watkins, and he was arrested but committed suicide before he could be brought to trial.

Still the use of ethylene glycol in medicines continues. In 2009 in Nigeria, a teething mixture for babies called My Pikin Teething Mixture caused the deaths of more than 80 babies because it used ethylene glycol as a solvent for paracetamol. Children who were given it suffered vomiting, diarrhoea, and convulsions before dying. This outbreak was a repeat of a similar incident in 1990 when 116 people died as a result of a cough syrup made with ethylene glycol.

1.3 MURDER, WALTHAM, MASSACHUSETTS, 2004

Sports drinks are designed to replace the glucose and minerals that your body needs when you engage in strenuous exercise and sweat a lot. In the USA, the popular drink for this is Gatorade, a bottle of which contains 56 grams of carbohydrate, 4.5 grams of sodium, and 120 milligrams of potassium. One sport-loving woman regularly drank Gatorade and it was to this that her husband added another ingredient: ethylene glycol. It was the life insurance on his wife Julie that motivated 31-year-old James Keown to murder her with antifreeze in 2004.

Julie was 31 years old and they lived near Kansas City, Missouri, where Julie's parents were soybean farmers. She worked as a nurse and James worked for the Learning Exchange as a web-designer. Then, in 2003, he asked if he could enrol on a master's degree course at the Harvard Business School. His employers were happy for him to do this and he persuaded them that he could continue working for them from his new home on the east coast. They agreed, and the Keowns moved in January 2004 to Waltham, a town of 60 000 inhabitants located about 11 miles from Boston. But things were not as they appeared.

James also continued to broadcast a regular slot on a Missouri radio station but his days as a radio commentator were numbered. He was cheating his employer and was misusing a website design that they had asked him to develop for the Learning Exchange. When they tried to get in contact with him via the Harvard Business School, they discovered he was not registered with them. What, in fact, James had done was register for a course about the internet at the Harvard Extension School but he failed his exams. His deception had been uncovered and so the Learning Exchange sacked him.

Soon James was borrowing heavily to keep up the pretence of being employed and eventually was $34 000 in debt, and then his beloved Jaguar car was repossessed. However, he knew he would soon be exposed as bankrupt so he decided to murder Julie for her life insurance, and he planned to do this by putting ethylene glycol in her Gatorade.

Julie was first hospitalised in August 2004 after her speech became slurred and she stumbled when she walked. The doctors who treated her diagnosed a kidney disease and she recovered and was allowed home. Then James gave her a bigger dose of ethylene glycol on 4 September. She was admitted to hospital again and was clearly struggling with a mysterious illness which caused vomiting and slurred speech and which seemed to be related to her kidneys malfunctioning. Meanwhile, James played the part of a devoted and caring husband, always pressing her to drink her Gatorade to replace her minerals. The hospital doctors eventually discovered that she had been poisoned by ethylene glycol, but despite their efforts to save her, Julie died on 8 September. Before any action could be taken against him, James returned to the Midwest and went to live in Jefferson City, Missouri, a small town of 45 000 inhabitants and considered to be one of the prettiest towns in the USA.

When Julie's parents learned of the cause of her illness, they confronted James and he said that he thought she had found a soft-drink bottle in which someone had been storing antifreeze, and that she had drunk it. It confirmed their suspicions that James had poisoned her and they went to the police. Unaware of this, James continued to believe that his plan had worked and he told a friend how he intended spending the money he would get from Julie's life insurance of $250 000. He said he planned to buy a new BMW car and even thought of building a new house. However, his days of freedom were numbered, and he was arrested in 2005 and charged with the murder of his wife. Nor did it help his case when police examined his computer and discovered that he had searched the internet using the phrase 'ethylene glycol death human' a few days before Julie was first admitted to hospital.

James was eventually found guilty by a jury and sentenced to life imprisonment without parole.

1.4 ATTEMPTED MURDER, STOKE-ON-TRENT, 2005

One advantage of ethylene glycol as a murder weapon is that it tastes rather nice, with a sweetish flavour, and it isn't difficult to disguise it by putting it in other drinks. However, a would-be murderer was unaware that the alcohol in a drink could neutralise the effect of the poison. Nevertheless, she left her husband blind and deaf, although the deafness has been partly corrected by new technology.

When 28-year-old Kate Knight decided to kill her 38-year-old husband Lee in 2005 she added ethylene glycol to red wine. They had married when she was only 19 years old and she now wished to be rid of him. She saw poisoning her husband as a way out of an intolerable situation caused by her reckless spending and lack of income. Because she knew nothing about ethylene glycol's toxicity, she added only small amounts to begin with and, while this made Lee ill, he soon recovered. She realised she would have to use a bigger dose.

Meanwhile, she would lavish loving care on her husband and show concern for his welfare. He even believed his wife had a job working at a call centre, but she was living on credit and eventually owed £17 000, having taken out a loan of £10 000 in October 2003 and a further one of £7000 in March 2004. Her financial worries would be solved if Lee died because he had life insurance of £130 000 paid for by his employer JCB, manufacturer of construction equipment. He worked at their Uttoxeter plant, about 15 miles from where they lived in Stoke-on-Trent.

Kate played the role of a caring wife very successfully; greeting him warmly when he came home from work and making sure he had red wine for his evening meal. On their wedding anniversary in April 2005, Kate gave Lee a particularly large dose of ethylene glycol to accompany an Indian takeaway which she had ordered, knowing that he was particularly fond of such dishes. Lee became so ill after this particular meal that he rang for an ambulance and was taken to hospital in Stoke-on-Trent where he started to recover.

This was something of a setback for Kate's plan, but she was not yet done with poisoning Lee. When she visited him in hospital the next day, she took him a litre bottle of flavoured water that she had also poisoned and which she insisted he should drink. Lee now became delirious and the doctors put him on dialysis in order to keep him alive. Eventually, he suffered a massive haemorrhage during which he lost six pints of blood. He lay in a coma for two months before he finally regained consciousness, and yet the true cause of his condition was still not recognised. Kate now said she was unable to visit him because she had to look after their son Jack. During this time, their car and other items were repossessed because of unpaid debts. Her attempt to murder Lee had failed, although her husband had been on the point of dying and was now blind and deaf.

So what gave Kate away? In fact, she had told a neighbour friend that she was going to poison Lee because she was no longer in love with him. The neighbour simply thought of these remarks as mere fantasy, but she told a cousin of Lee's what Kate had said, and the cousin told Lee's parents and they told the doctors at the hospital. At last they knew what they were dealing with and informed the police, who went round to Kate's home. There they discovered an almost empty bottle of antifreeze, a computer which had been used to search for poisons, and correspondence showing the mortgage had increased by £30 000 while Lee had been in hospital.

The jury at Stafford Crown Court took eight hours to convict Kate of attempted murder following a three-week trial in January 2008. She was sentenced to 30 years in jail and told that she would have to serve at least 15 years before being eligible for parole.

1.5 ATTEMPTED MURDER, HOUSTON, TEXAS, 2013

On 29 September 2014, Ana Gonzalez-Angulo was found guilty of poisoning her onetime lover George Blumenschein because he refused to give up his long-time partner and move in with her. Both Ana and George were doctors researching cancer at the MD Anderson Cancer Center, which is part of the University of Texas in Houston, USA. This is one of the world's leading institutes for this kind of research.