Floralozone

Floralozone is a reaction mass of 3-(o-ethylphenyl)-2,2-dimethylpropionaldehyde and 3-(p-ethylphenyl)-2,2-dimethylpropionaldehyde. Its molecular formula is C₁₃H₁₈O and its molecular weight is 190.28. The two components share the formula and differ in where the ethyl group sits on the benzene ring, at position 2 in one and position 4 in the other. Indexes of chemical names list the mixture as benzenepropanal, 2(or 4)-ethyl-α,α-dimethyl-. Cosmetic ingredient databases give its function as perfuming.

Chemistry

The 4-ethylphenyl component is 3-(4-ethylphenyl)-2,2-dimethylpropanal, CAS 67634-15-5, and the 2-ethylphenyl component is 3-(2-ethylphenyl)-2,2-dimethylpropanal, CAS 67634-14-4. It is soluble in alcohol and insoluble in water. Its shelf life is 24 months or longer if it is stored in a cool, dry place in tightly sealed containers, protected from heat and light. Its export tariff code is 2906.19.0000. The para isomer has the European inventory number 266-819-2 and is PubChem compound 105513. The ortho isomer has the number 266-818-7 and is PubChem compound 105512. Estimated XlogP3 values are 3.30 for the para isomer and 3.50 for the ortho isomer. A predicted density of 0.942 g/cm³ is given for the ortho isomer, and the solubility in water is estimated at 21.05 mg/L at 25 °C. The para isomer has a Kovats retention index of 1456.8. The proton NMR spectrum of the 4-ethyl compound prepared in the patent example shows one proton at 9.62 ppm, four aromatic protons near 7.15 ppm, a two-proton multiplet at 2.8 ppm, a two-proton quartet at 2.6 ppm and a nine-proton multiplet near 1.2 ppm.

Manufacture

A patented process for aromatic aldehydes, with Floralozone among its examples, first treats an aromatic hydrocarbon with paraformaldehyde and hydrogen bromide and then reacts the product with an aldehyde under a phase-transfer catalyst. The catalyst can be a tetraalkylammonium halide such as tetrabutylammonium iodide, and the reaction temperature is preferably 60 to 90 °C, more preferably 70 to 80 °C. In the Floralozone example, the first step used 50 grams (0.47 mol) of ethylbenzene and 15.56 grams of paraformaldehyde in 100 mL of acetic acid, with 138.6 grams of a 33% solution of hydrogen bromide in acetic acid added dropwise over 30 minutes. In the second step, 10 grams (50.2 mmol) of compound 2 and 5.03 grams (69.8 mmol) of isopropanal were added to 2.63 grams of sodium hydroxide and 0.27 grams of PTC 2 in water, toluene and THF. The reaction was followed by gas chromatography, and the organic phase was dehydrated with anhydrous sodium sulfate. The phase-transfer catalyst was used at 0.02 equivalent.

Safety

Its European hazard classification is irritant (Xi), irritating to skin and eyes. The hazard statements H317, H315 and H410 are listed for the material with CAS 67634-14-4. No listed EU fragrance allergens are declared for it. The material with CAS 67634-14-4 carries the GHS07 and GHS09 pictograms and the signal word Warning. Supplier labels state that it causes skin irritation, may cause an allergic skin reaction and is very toxic to aquatic life with long lasting effects. Both isomers are on the Canadian Domestic Substances List, and the material with CAS 67634-14-4 is TSCA listed. Its German water hazard class (WGK) is 2. It is a raw material for formulation work and must not be applied to the skin undiluted.

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