1,2-Cyclohexane dicarboxylic acid diisononyl ester

1,2-Cyclohexane dicarboxylic acid diisononyl ester
IUPAC name 1,2-cyclohexane dicarboxylic acid diisononyl ester
Other names Diisononyl cyclohexane-1,2-dicarboxylate Cyclohexane-1,2-dicarboxylic acid diisononyl ester Hexamoll DINCH (tradename)
Identifiers
CAS number	166412-78-8, 474919-59-0
ChemSpider	9699466 Y
InChI InChI=1S/C26H48O4/c1-21(2)15-9-5-7-13-19-29-25(27)23-17-11-12-18-24(23)26(28)30-20-14-8-6-10-16-22(3)4/h21-24H,5-20H2,1-4H3 Y Key: HORIEOQXBKUKGQ-UHFFFAOYSA-N Y
Properties
Molecular formula	C26H48O4
Molar mass	424.66 g mol−1
Appearance	colorless liquid[1]
Odor	almost odorless[1]
Density	0.944–0.954 g·cm-3 [1]
Melting point	Pour point: -54 °C [1]
Hazards
MSDS	BASF Safety Data Sheet
EU Index	431-890-2
EU classification	Not classified as a dangerous substance[2]
R-phrases	None[2]
S-phrases	None[2]
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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.^[3] According to BASF, Hexamoll DINCH is the "most widely used phthalate substitute in the world".^[4]

Production

The two commercial routes to manufacture 1,2-cyclohexane dicarboxylic acid diisononyl ester are the catalytic hydrogenation of diisononyl phthalate^[5][6] 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.

Regulatory approval

Food contact

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.^[7] 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".^[8]

Toys

A US federal law was passed in 2008 banning the use of some phthalates in children's toys.^[9] 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.^[4]

In the European Union 1,2-cyclohexane dicarboxylic acid diisononyl ester is not listed in directive 2005/84/EC which bans the use of certain phthalates in toys and childcare articles and thus can be used safely in toy and childcare articles.^[10]

References

1. ^ ^{a b c d} BASF Technical Leaflet Hexamoll DINCH
2. ^ ^{a b c} BASF Safety Data Sheet Hexamoll DINCH. Accessed 2010-06-14
3. ^ Flexible vinyls get new non-phthalate plasticizer. (Keeping Up With Additives). (September 1, 2002). Plastics Technology. Allbusiness.com. Accessed 2009-02-12.
4. ^ ^{a b} Sarah Varney (February 12, 2009). New Safety Law Doesn't Mean All's Well In Toyland. NPR. Accessed 2009-02-12.
5. ^ Innovative plasticizer alternative to phthalates for non-PVC applications
6. ^ Patent WO 99/32427, "Verfahren zur Hydrierung von Benzolpolycarbonsäuren oder Derivaten davon unter Verwendung eines Makroporen aufweisenden Katalysators", July 1, 1999, BASF AG
7. ^ EFSA: Opinion of the Scientific Panel on food additives, flavourings, processing aids and materials in contact with food (AFC) on a request related to a 12th list of substances for food contact materials, EFSA-Journal, 2006, 395–401, 1–21.
8. ^ Official Journal of the European Union: Corrigendum to Commission Directive 2007/19/EC of 30 March 2007 amending Directive 2002/72/EC relating to plastic materials and articles intended to come into contact with food and Council Directive 85/572/EEC laying down the list of simulants to be used for testing migration of constituents of plastic materials and articles intended to come into contact with foodstuffs, April 2, 2007.
9. ^ Brett Clanton (August 11, 2008). Federal ban on a chemical used in toys will affect Texas. Houston Chronicle. Accessed 2009-02-12.
10. ^ Official Journal of the European Union: Directive 2005/84/EC of the European Parliament and of the Council of 14 December 2005 amending for the 22nd time Council Directive 76/769/EEC on the approximation of the laws, regulations and administrative provisions of the Member States relating to restrictions on the marketing and use of certain dangerous substances and preparations (phthalates in toys and childcare articles)

External links

• Hexamoll