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
3D model (JSmol)
Abbreviations DINP
ChEBI
ChemSpider
ECHA InfoCard 100.044.602
UNII
  • 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 checkY
    Key: HBGGXOJOCNVPFY-UHFFFAOYSA-N checkY
  • 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
  • O=C(OCCCCCCC(C)C)c1ccccc1C(=O)OCCCCCCC(C)C
Properties
C26H42O4
Molar mass 418.618 g·mol−1
Appearance Oily viscous liquid
Density 0.98 g/cm3
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
<0.01 g/mL at 20 °C
Viscosity 64 to 265 mPa·s
Hazards
Flash point 221 °C (430 °F; 494 K) (c.c.)
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

Health Issues

The European Union has set a maximum specific migration limit (SML) 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

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. S2CID 44120848.
  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. "Evaluation of new scientific evidence concerning DINP and DIDP". European Chemicals Agency. Archived from the original on 2022-09-01. Retrieved 2020-01-26.
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