Does limonene react with calcium hydroxide or acetic acid?

Question

I can't find the results of too many experiments with Limonene. Which has many uses (e.g. making soap).

I'm curious of the results of combining Limonene and Calcium Hydroxide (Lime) in one experiment and another experiment combining Limonene and White Vinegar.

What is the result of these equations? Are the products potentially dangerous?

Could they result in combustion?

C₁₀H₁₆ + CH₃COOH → ?

C₁₀H₁₆ + CaH₂O₂ → ?

Answer 1

I can't find the results of too many experiments with Limonene.

Actually, there are quite a lot and the feature article Limonene: a versatile chemical of the bioeconomy, Chem. Commun., 2014, 50, 15288-15296 by Rosaria Ciriminna, Monica Lomeli-Rodriguez, Piera Demma Carà, Jose A. Lopez-Sanchez and Mario Pagliaro provides an interesting insight:

1. d-limonene (1) is available in large quantities as a side product in the production of orange juice

2. it is widely used as a bio-based solvent to replace petroleum-based solvents for various purposes, such as

   • general household cleaners
   • degreasing of metals
   • outdoor maintenance cleaners

3. it is used as an insecticide

In order to to prove comsumer-friendliness of d-limonene and its degradation products, a lot of studies on the reaction of d-limonene with oxygen, leading to endoperoxides, hydroperoxides, and the monoterpene ketone carvone (2), have been performed.

4. In the ongoing BioProMo project, the bacterial conversion of d-limonene to the carboxylic acid 3 is examined. The latter is a natural preservative.

I'm curious of the results of combining Limonene and Calcium Hydroxide (Lime) in one experiment and another experiment combining Limonene and White Vinegar.

To my information, these combinations aren't used in industrial or academic research, but in another context.

As outlined above, d-limonene is widely used as a natural replacement for other organic solvents, which aren't easily available outside science and/or industry. As a consequence, d-limonene as a solvent has also found its way into recipes for the clandestine extraction of controlled substances from plant material.

Some of these recipes seem to promote the combination of d-limonene, calcium hydroxide, and white vinegar (as a source of acetic acid) to extract N,N-dimethyltryptamine (DMT) as its acetate from the bark of Mimosa tenuiflora.

While this seems technically possible and reactions between d-limonene, the base, and the acetic acid are not to be expected, the posession of the extraction product is apparently illegal in a variety of countries.