Diisononyl phthalate

Diisononyl phthalate (DINP) is a phthalate used as a plasticizer. DINP is typically a mixture of chemical compounds consisting of various isononyl esters of phthalic acid, and is commonly used in a large variety of plastic items.

Diisononyl phthalate[1]

Names
Preferred IUPAC name Bis(7-methyloctyl) benzene-1,2-dicarboxylate
Other names Bis(7-methyloctyl) phthalate
Identifiers
CAS Number	28553-12-0 68515-48-0
3D model (JSmol)	Interactive image
Abbreviations	DINP
ChEBI	CHEBI:35459
ChemSpider	513622
ECHA InfoCard	100.044.602
PubChem CID	590836
UNII	4010KIX4CK
CompTox Dashboard (EPA)	DTXSID60860420 DTXSID4022521, DTXSID60860420
InChI InChI=1S/C26H42O4/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/h11-12,17-18,21-22H,5-10,13-16,19-20H2,1-4H3 Key: HBGGXOJOCNVPFY-UHFFFAOYSA-N InChI=1/C26H42O4/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/h11-12,17-18,21-22H,5-10,13-16,19-20H2,1-4H3 Key: HBGGXOJOCNVPFY-UHFFFAOYAX
SMILES O=C(OCCCCCCC(C)C)c1ccccc1C(=O)OCCCCCCC(C)C
Properties
Chemical formula	C26H42O4
Molar mass	418.618 g·mol^−1
Appearance	Oily viscous liquid
Density	0.98 g/cm^3
Melting point	−43 °C (−45 °F; 230 K)
Boiling point	244 to 252 °C (471 to 486 °F; 517 to 525 K) at 0.7 kPa
Solubility in water	<0.01 g/mL at 20 °C
Viscosity	64 to 265 mPa·s
Hazards
Flash point	221 °C (430 °F; 494 K) (c.c.)
Autoignition temperature	380 °C (716 °F; 653 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

The European Union has set a maximum specific migration limit from food contact materials of 9 mg/kg food for the sum of diisononyl phthalates and diisodecyl phthalates.[2]

DINP is listed as a substance "known to the State of California to cause cancer" under Proposition 65 legislation.[3]

Studies find that exposure to environmentally relevant concentrations of DINP in zebrafish disrupt the endocannabinoid system (ECS) and affect reproduction in a gender specific manner,[4] and have other adverse effects on aquatic organisms, as DINP upregulates orexigenic signals and causes hepatosteatosis together with deregulation of the peripheral ECS and lipid metabolism.[5]

ECHA's Risk Assessment Committee (RAC) has concluded, on March 7 2018, that Di-isononyl phthalate (DINP) does not warrant classification for reprotoxic effects under the EU's Classification, Labelling and Packaging (CLP) regulation [6]

See also

• Diisoheptyl phthalate
• Plastic pollution

References

1. Diisononyl phthalate at Inchem.org
2. "EU legislative list for food contact materials".
3. "State of California, Chemicals known to the state to cause cancer or reproductive toxicity, January 3, 2014" (PDF). Archived from the original (PDF) on 2014-01-10.
4. Forner-Piquer, Isabel; Santangeli, Stefania; Maradonna, Francesca; Rabbito, Alessandro; Piscitelli, Fabiana; Habibi, Hamid R.; Di Marzo, Vincenzo; Carnevali, Oliana (2018-10-01). "Disruption of the gonadal endocannabinoid system in zebrafish exposed to diisononyl phthalate". Environmental Pollution. 241: 1–8. doi:10.1016/j.envpol.2018.05.007. ISSN 0269-7491. PMID 29793103.
5. Forner-Piquer, Isabel; Maradonna, Francesca; Gioacchini, Giorgia; Santangeli, Stefania; Allarà, Marco; Piscitelli, Fabiana; Habibi, Hamid R; Di Marzo, Vincenzo; Carnevali, Oliana (2017-08-14). "Dose-Specific Effects of Di-Isononyl Phthalate on the Endocannabinoid System and on Liver of Female Zebrafish". Endocrinology. 158 (10): 3462–3476. doi:10.1210/en.2017-00458. ISSN 0013-7227. PMID 28938452.
6. https://echa.europa.eu/documents/10162/31b4067e-de40-4044-93e8-9c9ff1960715