Octyltriazone

Structural formula
Structural formula without stereochemistry
General
Surname	Octyltriazone
other names	Ethylhexyl triazone Tris (2-ethylhexyl) -4,4 ', 4' '- (1,3,5-triazine-2,4,6-triyltriimino) tribenzoate ETHYLHEXYL TRIAZONE ( INCI )
Molecular formula	C 48 H 66 N 6 O 6
Brief description	white crystals
External identifiers / databases
CAS number 88122-99-0 EC number 402-070-1 ECHA InfoCard 100.100.393 PubChem 159201 Wikidata Q2455834
properties
Molar mass	823.07 g mol −1
Physical state	firmly
Melting point	129 ° C
solubility	soluble in ethyl acetate and ethanol
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary no GHS pictograms H and P phrases H: 413 P: 273
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Octyltriazon is a mixture of eight isomeric chemical compounds derived from cyanurtriamide or melamine .

Presentation and extraction

The synthesis is possible by transesterification of 2-ethylhexyl p -aminobenzoate with cyanuric chloride . Since a racemic 2-ethylhexyl derivative is used as a starting point, this synthesis produces a mixture of isomers.

properties

Octyltriazon is a white crystalline substance that melts at 129 ° C with a heat of fusion of 23 kJ mol ⁻¹ . The compound is very soluble in ethyl acetate and ethyl acetate / ethanol mixtures.

Solubility of octyltriazone
temperature	in ° C	25th	30th	35	40	45
Ethyl acetate	in g · l −1	318.8	364.6	413.2	462.4	512.5
Ethyl acetate / ethanol (90/10 Ma%)	in g · l −1	389.0	430.0	479.9	525.1	567.3
Ethyl acetate / ethanol (80/20 Ma%)	in g · l −1	404.9	450.2	498.6	539.7	600.0
Ethyl acetate / ethanol (70/30 mass%)	in g · l −1	383.6	438.5	502.9	541.3	608.5

Due to the ethylhexyl group, octyltriazone is a mixture of stereoisomers, which consists of 1/8 ( R , R , R ) and ( S , S , S ) isomers and 3/8 ( R , R , S ) and ( R , S , S ) isomers. The absorption maximum of octyltriazone is 314 nanometers .

use

Octyltriazon is used in sun creams as a UV filter in the UVB range. According to EU Directive 76/786 EEC, a maximum concentration of 5 g per 100 g is permitted in formulations. It is marketed by BASF as Uvinul T 150 .

Individual evidence

1. ↑ Entry on ETHYLHEXYL TRIAZONE in the CosIng database of the EU Commission, accessed on December 28, 2019.
2. ↑ ^{a b c} F. Berte, M. Fabbi, L. Bemporad, F. Maestri: Crystalline form of a triazine derivative and its procedure for its production. 3V Sigma SpA 2014. Patent US2014 / 255324 A1.
3. ↑ ^{a b c} S. J. Rodriguez, DM Cristancho, PC Neita, EF Vargas, F. Martinez: Solution Thermodynamics of Ethylhexyl Triazone in Some Ethanol + Ethyl Acetate Mixtures. In: J. Sol. Chem. Volume 39, 2010, pp. 1122-1133, doi: 10.1007 / s10953-010-9575-0 .
4. ↑ Entry on tris (2-ethylhexyl) -4,4 ′, 4 ′ ′ - (1,3,5-triazine-2,4,6-triyltriimino) tribenzoate in the GESTIS substance database of the IFA , accessed on February 28 2017(JavaScript required) .
5. ↑ Entry on Tris (2-ethylhexyl) -4,4 ′, 4 ′ ′ - (1,3,5-triazine-2,4,6-triyltriimino) tribenzoate in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
6. ↑ Data sheet Octyl triazone at biosynth.com, accessed on October 14, 2015.
7. ↑ patent WO2012 / 127425 A1: Kroener, R., BASF SE 2012th
8. ↑ ^{a b} Patent US8765753B2 : Process for the preparation of s-triazine compounds. Registered on March 21, 2012 , published on July 1, 2014 , applicant: BASF, inventor: Rudi Kroner. ‌
9. ↑ UV Filter - Technical Information ( Memento of the original from September 29, 2015 in the Internet Archive ) Info: The archive link was inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this notice. , 2011. 
10. ↑ P. Wolf: UV filter, State of the Art. In: Dermatologist. Volume 60, 2009, pp. 285-293, doi: 10.1007 / s00105-008-1623-y .