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Tylenol, now from palm trees instead of petroleum

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Tylenol, now from palm trees instead of petroleum

The ubiquitous medicine’s active ingredient is made today from crude oil-derived chemicals, but a greener route to relieving aches and pain is possible
April 11, 2024

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Tylenol is an environmental headache. Acetaminophen—the active ingredient in the ubiquitous pain-relieving medicine—is typically made from chemicals derived from crude oil.

But researchers now report a way to make the pharmaceutical compound from the wood of palm and poplar trees. The study, published in the journal ChemSusChem, presents a way to make the commonly used pain medicine more environmentally friendly. It is also possible to modify the process to produce an array of chemical building blocks for plastics, pigments, and pharmaceuticals, the researchers say.

Acetaminophen, also called paracetamol, is one of the most produced pharmaceutical compounds in the world. People around the world consume over 16,000 metric tons of it every year. The industrial production of paracetamol involves turning benzene compounds into phenols, which can then by turned into paracetamol. Benzene, the starting material, comes from petroleum.

Last year, a team from the University of Bath in the UK made paracetamol and ibuprofen from a type of turpentine compound found in pine tree wood. The compound could be obtained from the waste product of the paper and forestry industries.

The new approach is based on work by Steven Karlen and John Ralph of UW–Madison. In 2019, the researchers led a team on a patent for a method to make paracetamol from lignin, the strong polymer that makes plant cell walls rigid.

 

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Turns out, the lignin in poplar and palm trees contains a compound called pHB that has a similar ring-shaped molecular structure made of six carbon atoms as petroleum-derived benzene. But that initial process did not convert enough of the pHB into paracetamol.

Now, the team has come up with a three-stage process that first converts pHB into another chemical that they can then turn into paracetamol. The method uses green solvents and is primarily water-based. It converts 90 percent of the raw material into paracetamol, and Karlen said in a press release that it should be possible increase the yield to 99 percent.

Increasing the yield of these bio-based methods will be crucial to bring down the cost to compete with the petroleum-derived acetaminophen found at drug stores for cheap.

Source: Steven D Karlen et al. Production of biomass‐derived p‐hydroxybenzamide: Synthesis of p‐aminophenol and paracetamol, ChemSusChem, 2024.

Image: ©Anthropocene Magazine

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