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1,2-Cyclohexane dicarboxylic acid diisononyl ester

1,2-Cyclohexane dicarboxylic acid diisononyl ester
1,2-Cyclohexane dicarboxylic acid diisononyl ester.svg
Names
IUPAC name
Diisononyl cyclohexane-1,2-dicarboxylate
Other names
Cyclohexane-1,2-dicarboxylic acid diisononyl ester;
Hexamoll DINCH (tradename).
Identifiers
3D model (Jmol)
ChemSpider
ECHA InfoCard 100.121.507
Properties
C26H48O4
Molar mass 424.67 g·mol−1
Appearance colorless liquid
Odor almost odorless
Density 0.944–0.954 g·cm−3
Melting point Pour point: −54 °C (−65 °F; 219 K)
Hazards
Safety data sheet BASF Safety Data Sheet
Not classified as a dangerous substance
R-phrases None
S-phrases None
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YesYN ?)
Infobox references

1,2-Cyclohexane dicarboxylic acid diisononyl ester is a plasticizer for the manufacture of flexible plastic articles in sensitive application areas such as toys, medical devices and food packaging. From a chemical point of view it belongs to the group of aliphatic esters.

In 2002 BASF started selling 1,2-cyclohexane dicarboxylic acid diisononyl ester under the tradename of Hexamoll DINCH as an alternative for phthalate plasticizers.

The two commercial routes to manufacture 1,2-cyclohexane dicarboxylic acid diisononyl ester are the catalytic hydrogenation of diisononyl phthalate and the Diels-Alder reaction of a maleic acid ester with 1,3-butadiene followed by hydrogenation. In the case of the catalytic hydrogenation the aromatic part of the diisononyl phthalate is transformed to a cyclohexane ring by a formal addition of 6 hydrogen atoms while the alkyl and ester groups are not affected by the hydrogenation.

In the European Union the European Food Safety Authority has approved 1,2-cyclohexane dicarboxylic acid diisononyl ester for a wide variety of food contact applications in October 2006. In 2007 1,2-cyclohexane dicarboxylic acid diisononyl ester has been added to Annex III of the "Directive 2002/72/EC relating to plastic materials and articles intended to come into contact with food". The EU Directive 2002/72 has meanwhile been superseded by Regulation (EU) No. 10/2011. Hexamoll DINCH had been included by its chemical name in “Recommendations” I.

A US federal law was passed in 2008 banning the use of some phthalates in children's toys. When the law took effect in February 2009, Mattel and Learning Curve confirmed to NPR they were substituting phthalates with Hexamoll DINCH and citrate-based plasticizers.


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