1,2-Cyclohexanedicarboxylic acid diisononyl ester

Structural formula
	Simplified structural formula without representation of the isomers, see composition
General
Surname	1,2-Cyclohexanedicarboxylic acid diisononyl ester
other names	Diisononylcyclohexane-1,2-dicarboxylate; Diisononyl cyclohexane-1,2-dicarboxylate;
Molecular formula	C 26 H 48 O 4
Brief description	colorless clear liquid with a barely perceptible odor
External identifiers / databases
EC number	605-439-7
ECHA InfoCard	100.121.507
PubChem	11524680
ChemSpider	9699466
Wikidata	Q161456
properties
Molar mass	424.7 g mol −1
Physical state	liquid
density	0.944-0.954 g cm -3
Melting point	−54 ° C ( pour point )
Vapor pressure	1.3 · 10 −4 Pa (50 ° C)
solubility	almost insoluble in water
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

1,2-cyclohexane dicarboxylic acid diisononyl ester , abbreviated DINCH (according to the English designation D i i as n onyl 1,2- c yclo h exanedicarboxylic acid ), chemically belongs to the group of aliphatic esters .

The mixture of different isomers that is produced during production is used as a plasticizer for the production of plastic items for sensitive areas of application such as children's toys , medical products or for the production of plastics for packaging food.

The best-known trade name for the plasticizer is Hexamoll DINCH . It was developed by BASF as an alternative to the harmful plasticizer DEHP (diethylhexyl phthalate), the production of which the Group discontinued in Europe at the end of 2005.

Manufacturing

The commercial synthesis of diisononyl 1,2-cyclohexanedicarboxylate is carried out either by catalytic hydrogenation from diisononyl phthalate . In catalytic hydrogenation, the aromatic part of the molecule is converted into a cyclohexane ring by the formal addition of 6 hydrogen atoms . The alkyl and ester groups are not affected.

composition

During the production of diisononyl 1,2-cyclohexanedicarboxylate, a complex mixture of different isomeric compounds is formed. In the 1,2-cyclohexanedicarboxylic acid substructure, the two carboxylic acid groups can be linked in a cis or trans position on the cyclohexane ring.

The alcohol radicals R ¹ and R ² are not necessarily identical. The composition of the C ₉ H ₁₉ isomers is about 10% n -nonyl, 35-40% methyloctyl, 40-45% dimethylheptyl and 5-10% methylethylhexyl alcohol.

The asymmetrically branched alcohols also have stereocenters, so there are stereoisomers .

In addition, traces of 1,2-benzenedicarboxylic acid dinonyl ester (linear or branched), dinonyl ether , nonanol (linear or branched), cyclohexanecarboxylic acid onyl ester (linear or branched) and 2-methylcyclohexanecarboxylic acid onyl ester (linear or branched) may be contained as impurities .

use

1,2-Cyclohexanedicarboxylic acid diisononyl ester is suitable as a plasticizer in children's toys made of PVC and for the manufacture of products in medical technology . It is regulated in the context of global migration of 60 mg per kilogram of food and is therefore suitable for a large number of products that come into contact with food such as packaging films, hoses or seals.

Human exposure

No metabolites of 1,2-cyclohexanedicarboxylic acid diisononyl ester were found in urine samples from 1999 and 2003 . From 2006 to 2012, the proportion with positive results rose from 7% to 98%.

Legal status

The European Food Safety Authority ( EFSA ) received a positive decision from the beginning of October 2006 . In 2007, diisononyl 1,2-cyclohexanedicarboxylate was included in Annex III of the "Directive 2002/72 / EC on plastic materials and articles intended to come into contact with food". This directive was replaced on May 1st, 2011 by the European regulation 10/2011. Diisononyl 1,2-cyclohexanedicarboxylate is listed there in Appendix I.

Individual evidence

↑ ^a ^b ^c ^d ^e BASF: Technical Data Sheet Hexamoll ^® DINCH , (PDF; 57.4 kB; German, as of September 2013), accessed on May 6, 2014.

↑ ^a ^b No harmonized classification is yet available for this substance . A labeling of 1,2-cyclohexanedicarboxylic acid, diisononyl ester, reaction products of hydrogenation of di-isononylphthalates (n-butenes based) in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), retrieved on 7 January 2016.

↑ Patent WO 99/32427, Process for the hydrogenation of benzene polycarboxylic acids or derivatives thereof using a catalyst having macropores, July 1, 1999, BASF AG

↑ ^a ^b SCENIHR Opinion on The safety of medical devices containing DEHP- plasticized PVC or other plasticizers on neonates and other groups possibly at risk (2015 update) , as of February 2016.

^ André Schütze, Rainer Otter, Hendrik Modick, Angelika Langsch, Thomas Brüning, Holger M. Koch: Additional oxidized and alkyl chain breakdown metabolites of the plasticizer DINCH in urine after oral dosage to human volunteers . In: Archives of Toxicology . March 15, 2016, p. 1-10 , doi : 10.1007 / s00204-016-1688-9 .

^ André Schütze, Marike Kolossa-Gehring, Petra Apel, Thomas Brüning, Holger M. Koch: Entering markets and bodies: Increasing levels of the novel plasticizer Hexamoll ^® DINCH ^® in 24 h urine samples from the German Environmental Specimen Bank . Int J Hyg Environ Health . 2014. 217 (2-3), pp. 421-426; PMID 24029725 ; doi : 10.1016 / j.ijheh.2013.08.004 .

↑ EFSA: Opinion of the Scientific Panel on food additives, flavors, 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.

↑ Directive 2007/19 / EC of the Commission of April 2nd, 2007 amending Directive 2002/72 / EC on plastic materials and articles intended to come into contact with food and Directive 85/572 / EEC of the Council on the list of simulants for the migration tests of materials and articles made of plastic which are intended to come into contact with food . In: Official Journal of the European Union . April 12, 2007.

↑ Regulation (EU) No. 10/2011 of the Commission of January 14, 2011 on plastic materials and objects intended to come into contact with food , accessed on July 30, 2013 In: Official Journal of the European Union .

[BASF-1] BASF: Technical Data Sheet Hexamoll ^® DINCH , (PDF; 57.4 kB; German, as of September 2013), accessed on May 6, 2014.

[CL_EG-Nr._431-890-2-2] Template: CL Inventory / not harmonized No harmonized classification is yet available for this substance . A labeling of 1,2-cyclohexanedicarboxylic acid, diisononyl ester, reaction products of hydrogenation of di-isononylphthalates (n-butenes based) in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), retrieved on 7 January 2016.

[3] Patent WO 99/32427, Process for the hydrogenation of benzene polycarboxylic acids or derivatives thereof using a catalyst having macropores, July 1, 1999, BASF AG

[SCENIHR-4] SCENIHR Opinion on The safety of medical devices containing DEHP- plasticized PVC or other plasticizers on neonates and other groups possibly at risk (2015 update) , as of February 2016.

[5] André Schütze, Rainer Otter, Hendrik Modick, Angelika Langsch, Thomas Brüning, Holger M. Koch: Additional oxidized and alkyl chain breakdown metabolites of the plasticizer DINCH in urine after oral dosage to human volunteers . In: Archives of Toxicology . March 15, 2016, p. 1-10 , doi : 10.1007 / s00204-016-1688-9 .

[6] André Schütze, Marike Kolossa-Gehring, Petra Apel, Thomas Brüning, Holger M. Koch: Entering markets and bodies: Increasing levels of the novel plasticizer Hexamoll ^® DINCH ^® in 24 h urine samples from the German Environmental Specimen Bank . Int J Hyg Environ Health . 2014. 217 (2-3), pp. 421-426; PMID 24029725 ; doi : 10.1016 / j.ijheh.2013.08.004 .

[7] EFSA: Opinion of the Scientific Panel on food additives, flavors, 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] Directive 2007/19 / EC of the Commission of April 2nd, 2007 amending Directive 2002/72 / EC on plastic materials and articles intended to come into contact with food and Directive 85/572 / EEC of the Council on the list of simulants for the migration tests of materials and articles made of plastic which are intended to come into contact with food . In: Official Journal of the European Union . April 12, 2007.