1,2-Cyclohexane dicarboxylic acid diisononyl ester

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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 (JSmol)
ChemSpider
ECHA InfoCard 100.121.507
Properties
C26H48O4
Molar mass 424.67 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 (−65 °F; 219 K)[1]
Hazards
Safety data sheet BASF Safety Data Sheet
Not classified as a dangerous substance[2]
R-phrases (outdated) None[2]
S-phrases (outdated) None[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (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.[3]

Production[edit]

The two commercial routes to manufacture 1,2-cyclohexane dicarboxylic acid diisononyl ester are the catalytic hydrogenation of diisononyl phthalate[4][5] 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[edit]

Food contact[edit]

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;[6] 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plastic materials and articles intended to come into contact with food".[7] The EU Directive 2002/72 has meanwhile been superseded by Regulation (EU) No. 10/2011.[8] Hexamoll DINCH had been included by its chemical name in “Recommendations” I.

Toys[edit]

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.[10]

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.[11]

Possible Health Effects[edit]

A research group from Harvard and CDC stated that "the potential health effects from DINCH exposure remain largely unknown", their research at a fertility clinic showed that women who had been exposed to DINCH had lower estradiol hormone levels and fewer oocytes in their ovaries.[12]

According to the Swedish Environmental Research Institute "children's exposure to DINCH should be investigated in more detail and exposure to the general population should be closely monitored."[13]

The Chronic Hazard Advisory Panel of the U.S. Consumer Product Safety Commission "strongly encourages the appropriate U.S. agencies to obtain the necessary toxicological and exposure data to assess any potential risk from DINX" because of "lack of publically [sic] available information".[14][15]

According to a panel appointed by the French Agency for the Safety of Health Products (ANSM), there is very little clinical assessment data regarding the toxicity, migration from Medical Devices and population exposure of alternative plasticizers (e.g. DINCH/DINX) and their metabolites.[16]

A report by the Danish Ministry of the Environment states that DINCH/DINX may be a possible endocrine disruptor but further research is needed to evaluate the risk.[17]

Toxicogenomic screening showed that 648 genes were significantly changed after 48 hours exposure to DINCH suggesting that "DINCH is biologically active".[18]

References[edit]

  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. ^ Innovative plasticizer alternative to phthalates for non-PVC applications
  5. ^ Patent WO 99/32427, "Verfahren zur Hydrierung von Benzolpolycarbonsäuren oder Derivaten davon unter Verwendung eines Makroporen aufweisenden Katalysators", July 1, 1999, BASF AG
  6. ^ 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.
  7. ^ 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.
  8. ^ COMMISSION REGULATION (EU) No 10/2011 of 14 January 2011 on plastic materials and articles intended to come into contact with food Accessed 2013-08-05
  9. ^ Brett Clanton (August 11, 2008). Federal ban on a chemical used in toys will affect Texas. Houston Chronicle. Accessed 2009-02-12.
  10. ^ Sarah Varney (February 12, 2009). New Safety Law Doesn't Mean All's Well In Toyland. NPR. Accessed 2009-02-12.
  11. ^ 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)
  12. ^ Mínguez-Alarcón, Lidia; Souter, Irene; Chiu, Yu-Han; Williams, Paige L.; Ford, Jennifer B.; Ye, Xiaoyun; Calafat, Antonia M.; Hauser, Russ (2016-11-01). "Urinary concentrations of cyclohexane-1,2-dicarboxylic acid monohydroxy isononyl ester, a metabolite of the non-phthalate plasticizer di(isononyl)cyclohexane-1,2-dicarboxylate (DINCH), and markers of ovarian response among women attending a fertility center". Environmental Research. 151: 595–600. doi:10.1016/j.envres.2016.08.012. 
  13. ^ Bui, Thuy T.; Giovanoulis, Georgios; Cousins, Anna Palm; Magnér, Jörgen; Cousins, Ian T.; de Wit, Cynthia A. (2016-01-15). "Human exposure, hazard and risk of alternative plasticizers to phthalate esters". Science of The Total Environment. 541: 451–467. doi:10.1016/j.scitotenv.2015.09.036. 
  14. ^ Lioy, Paul J; Hauser, Russ; Gennings, Chris; Koch, Holger M; Mirkes, Philip E; Schwetz, Bernard A; Kortenkamp, Andreas. "Assessment of phthalates/phthalate alternatives in children’s toys and childcare articles: Review of the report including conclusions and recommendation of the Chronic Hazard Advisory Panel of the Consumer Product Safety Commission". Journal of Exposure Science and Environmental Epidemiology. 25 (4): 343–353. doi:10.1038/jes.2015.33. 
  15. ^ "Report to the U.S. Consumer Product Safety Commission by the CHRONIC HAZARD ADVISORY PANEL ON PHTHALATES AND PHTHALATE ALTERNATIVES" (PDF). United States Consumer Product Safety Commission. 2014. 
  16. ^ Bernard, L.; Décaudin, B.; Lecoeur, M.; Richard, D.; Bourdeaux, D.; Cueff, R.; Sautou, V. (2014-11-01). "Analytical methods for the determination of DEHP plasticizer alternatives present in medical devices: A review". Talanta. 129: 39–54. doi:10.1016/j.talanta.2014.04.069. 
  17. ^ B. S. Nielsen; D. Nørgaard Andersen; E. Giovalle; M. Bjergstrøm; P.B. Larsen (2014). "Alternatives to classified phthalates in medical devices, Danish Environmental Protection Agency, Environmental Project No. 1557, 2014, Copenhagen." (PDF). 
  18. ^ Nardelli, Thomas C.; Erythropel, Hanno C.; Robaire, Bernard (2015-10-07). "Toxicogenomic Screening of Replacements for Di(2-Ethylhexyl) Phthalate (DEHP) Using the Immortalized TM4 Sertoli Cell Line". PLOS ONE. 10 (10): e0138421. ISSN 1932-6203. PMC 4596883Freely accessible. PMID 26445464. doi:10.1371/journal.pone.0138421. 

External links[edit]