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
Preferred IUPAC name
Bis(7-methyloctyl) cyclohexane-1,2-dicarboxylate
Other names
Cyclohexane-1,2-dicarboxylic acid diisononyl ester;
Hexamoll DINCH (tradename)
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.121.507 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 605-439-7
PubChem CID
UNII
  • 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 Yes check.svgY
    Key: HORIEOQXBKUKGQ-UHFFFAOYSA-N Yes check.svgY
  • O=C(OCCCCCCC(C)C)C1C(C(=O)OCCCCCCC(C)C)CCCC1
Properties
C26H48O4
Molar mass 424.666 g·mol−1
Appearancecolorless 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]
Boiling point 394 °C
Hazards
Safety data sheet (SDS) BASF Safety Data Sheet
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

1,2-Cyclohexane dicarboxylic acid diisononyl ester (DINCH) is a mixture of organic compounds with the formula C6H10(CO2C9H19)2. DINCH is colorless oil. It is used as a plasticizer for the manufacture of flexible plastic articles in sensitive application areas such as toys, medical devices, and food packaging. It is of interest as an alternative for phthalate plasticizers, which are implicated as endocrine disruptors. [2]

Contents

Production

DINCH can be produced by the catalytic hydrogenation of diisononyl phthalate. [3] [4] Alternatively it can be prepared by Diels-Alder reaction of a diisononyl maleate with 1,3-butadiene followed by hydrogenation. In the case of the catalytic hydrogenation the aromatic, planar part of the diisononyl phthalate is transformed to a cyclohexane ring. Commercial DINCH consists of 90% of the cis and 10% of the trans (chiral) isomers.

BASF sells DINCH under the tradename of Hexamoll DINCH. [5]

Use

In February 2009, Mattel and Learning Curve confirmed that they were substituting phthalates with Hexamoll DINCH and citrate-based plasticizers. [6]

Regulatory approval

Food contact

In the European Union, the European Food Safety Authority approved DINCH for a wide variety of food contact applications in October 2006. [7] In 2007 DINCH 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] The EU Directive 2002/72 has meanwhile been superseded by Regulation (EU) No 10/2011. [9] Hexamoll DINCH is listed in Annex I of Regulation (EU) No 10/2011 by as Food Conctact Material (FCM) 775 by its chemical name, i.e. as 1,2-cyclohexanedicarboxylic acid, diisononylester.

Toys

In the European Union 1,2-cyclohexane dicarboxylic acid diisononyl ester was not listed in directive 2005/84/EC. These restrictions for certain phthalates are now transferred into Annex XVII, 51 and 52 of Regulation (EC) No 1907/2006 which ban the use of certain phthalates in toys and childcare articles and thus DINCH can be used safely in toys and childcare articles. [10]

Possible health effects

A research group from Harvard and CDC found suggestive negative associations between urinary MHiNCH, the monoester of DINCH, a minor urinary metabolite. Their research at a fertility clinic showed that women who had been exposed to DINCH had lower, but statistically not significant estradiol hormone levels and fewer, though not statistically significant number of oocytes in their ovaries. However, urinary MHiNCH concentrations were unrelated to mature oocyte yield and endometrial wall thickness. [11] The results are inconclusive and therefore, the authors suggest that more epidemiological studies would be needed for clarification.

The Swedish IVL Environmental Research Institute and researches from the Department of Environmental Science and Analytical Chemistry of Stockholm University recommend that "children's exposure to DINCH should be investigated in more detail and exposure to the general population should be closely monitored" [12] as DINCH is used as an alternative plasticizer in e.g. children's toys.

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 publicly available information". [13] [14]

A French group from the University of Clermont-Ferrand noted that clinical data and data regarding the migration from Medical Devices would be rare. The Project was funded by the French Agency for the Safety of Health Products (ANSM). It remains unclear why this Research Group was not able to identify the published human biomonitoring data which give a perfect overview on population exposure of alternative plasticizers (e.g. DINCH/DINX) and their metabolites. [15]

A report by the Danish Ministry of the Environment states that the available data for DINCH do not indicate a need for further investigations. Further, the conclusion is that 3 of the evaluated plasticizers, namely the substances COMGHA, DEHT and DINCH may be seen as the most promising alternatives, as these substances have an extended data set (complying to Annex X data requirements, i.e. a two-generation reproduction study) without indicating specific concern for reproductive toxicity or endocrine activity. [16] Toxicogenomic screening showed that 648 genes were significantly changed after 48 hours exposure to DINCH suggesting that "DINCH is biologically active". [17]

A 2022 Canadian study indicated DEHP and DINCH have similar influence on rat mammary glands. [18]

Related Research Articles

<span class="mw-page-title-main">Polyvinyl chloride</span> Common synthetic polymer

Polyvinyl chloride (alternatively: poly(vinyl chloride), colloquial: vinyl or polyvinyl; abbreviated: PVC) is the world's third-most widely produced synthetic polymer of plastic (after polyethylene and polypropylene). About 40 million tons of PVC are produced each year.

<span class="mw-page-title-main">Phthalates</span> Any ester derived from phthalic acid

Phthalates ( ), or phthalate esters, are esters of phthalic acid. They are mainly used as plasticizers, i.e., substances added to plastics to increase their flexibility, transparency, durability, and longevity. They are used primarily to soften polyvinyl chloride (PVC). While phthalates are commonly used as plasticizers, not all plasticizers are phthalates. The two terms are specific, unique, and not used interchangeably.

<span class="mw-page-title-main">Phthalic anhydride</span> Chemical compound

Phthalic anhydride is the organic compound with the formula C6H4(CO)2O. It is the anhydride of phthalic acid. Phthalic anhydride is a principal commercial form of phthalic acid. It was the first anhydride of a dicarboxylic acid to be used commercially. This white solid is an important industrial chemical, especially for the large-scale production of plasticizers for plastics. In 2000, the worldwide production volume was estimated to be about 3 million tonnes per year.

<span class="mw-page-title-main">RoHS</span> European Union directive restricting ten hazardous materials

The Restriction of Hazardous Substances Directive 2002/95/EC, short for Directive on the restriction of the use of certain hazardous substances in electrical and electronic equipment, was adopted in February 2003 by the European Union.

<span class="mw-page-title-main">Plasticizer</span> Substance added to a material to make it softer and more flexible

A plasticizer is a substance that is added to a material to make it softer and more flexible, to increase its plasticity, to decrease its viscosity, and/or to decrease friction during its handling in manufacture.

<span class="mw-page-title-main">Polymer clay</span> PVC-based hardenable modeling clay

Polymer clay is a type of hardenable modeling clay based on the polymer polyvinyl chloride (PVC). It typically contains no clay minerals, but like mineral clay a liquid is added to dry particles until it achieves gel-like working properties. Similarly, the part is put into an oven to harden, hence its colloquial designation as clay. Polymer clay is generally used for making arts and craft items, and is also used in commercial applications to make decorative parts. Art made from polymer clay can now be found in major museums.

<span class="mw-page-title-main">Bis(2-ethylhexyl) phthalate</span> Organic compound used as a plasticizer to soften polymer matrix

Bis(2-ethylhexyl) phthalate (di-2-ethylhexyl phthalate, diethylhexyl phthalate, diisooctyl phthalate, DEHP; incorrectly — dioctyl phthalate, DIOP) is an organic compound with the formula C6H4(CO2C8H17)2. DEHP is the most common member of the class of phthalates, which are used as plasticizers. It is the diester of phthalic acid and the branched-chain 2-ethylhexanol. This colorless viscous liquid is soluble in oil, but not in water.

<span class="mw-page-title-main">Benzyl butyl phthalate</span> Chemical compound

Benzyl butyl phthalate (BBP) is an organic compound historically used a plasticizer, but which has now been largely phased out due to health concerns. It is a phthalate ester of containing benzyl alcohol, and n-butanol tail groups. Like most phthalates, BBP is non-volatile and remains liquid over a wide range of temperatures. It was mostly used as a plasticizer for PVC, but was also a common plasticizer for PVCA and PVB.

<span class="mw-page-title-main">2-Ethylhexanol</span> Chemical compound

2-Ethylhexanol is an organic compound with the chemical formula CH3CH2CH2CH2CH(CH2CH3)CH2OH. It is a branched, eight-carbon chiral alcohol. It is a colorless liquid that is poorly soluble in water but soluble in most organic solvents. It is produced on a large scale (>2,000,000,000 kg/y) for use in numerous applications such as solvents, flavors, and fragrances and especially as a precursor for production of other chemicals such as emollients and plasticizers. It is encountered in plants, fruits, and wines. The odor has been reported as "heavy, earthy, and slightly floral" for the R enantiomer and "a light, sweet floral fragrance" for the S enantiomer.

<span class="mw-page-title-main">Diisobutyl phthalate</span> Chemical compound

Diisobutyl phthalate (DIBP) is a phthalate ester having the structural formula C6H4(COOCH2CH 2)2. It is formed by the esterification of isobutanol and phthalic anhydride. This and other phthalates are used as plasticizers due to their flexibility and durability. They are found in many industrial and personal products, such as lacquers, nail polish and cosmetics. DIBP can be absorbed via oral ingestion and dermal exposure. When it comes to excretion, DIBP is first converted into the hydrolytic monoester monoisobutyl phthalate (MIBP). The primary excretory route is urine, with biliary excretion being noted in minor amounts. DIBP has lower density and freezing point than the related compound dibutyl phthalate (DBP).

<span class="mw-page-title-main">Dimethyl phthalate</span> Chemical compound

Dimethyl phthalate (DMP) is an organic compound and phthalate ester. it is a colourless and oily liquid that is soluble in organic solvents, but which is only poorly soluble in water.

<span class="mw-page-title-main">Dibutyl phthalate</span> Chemical compound

Dibutyl phthalate (DBP) is an organic compound which is commonly used as a plasticizer because of its low toxicity and wide liquid range. With the chemical formula C6H4(CO2C4H9)2, it is a colorless oil, although impurities often render commercial samples yellow.

Tygon® is a brand name for a family of flexible polymer tubing consisting of a variety of materials to be used "across a range of specialized fluid transfer requirements". The specific composition of each type is a trade secret. Some variants have multiple layers of different materials. Tygon is a registered trademark of Saint-Gobain Corporation. It is an invented word, owned and used by Saint-Gobain and originated in the late 1930s. Tygon products are produced in three countries, but sold throughout the world. Tygon tubing is used in many markets, including food and beverage, chemical processing, industrial, laboratory, medical, pharmaceutical, and semiconductor processing. There are many formulations of clear, flexible, Tygon tubing. The chemical resistance and physical properties vary among the different formulations, but the tubing generally is intended to be "so resistant to chemical attack that it will handle practically any chemical", whether liquid, gas, or slurry. While largely non-reactive, Tygon has been reported to liberate carbon monoxide and is listed among carbon monoxide-releasing molecules.

<span class="mw-page-title-main">Diisononyl phthalate</span> Chemical compound

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 products.

<span class="mw-page-title-main">Diisodecyl phthalate</span> Chemical compound

Diisodecyl phthalate (DIDP) is a commonly used plasticizer used in the production of plastic and plastic coating to increase flexibility. It is a mixture of compounds derived from the esterification of phthalic acid and isomeric decyl alcohols.

<span class="mw-page-title-main">Diethyl phthalate</span> Chemical compound

Diethyl phthalate (DEP) is a phthalate ester. It occurs as a colourless liquid without significant odour but has a bitter, disagreeable taste. It is more dense than water and insoluble in water; hence, it sinks in water.

Epoxidized soybean oil (ESBO) is a collection of organic compounds obtained from the epoxidation of soybean oil. It is used as a plasticizer and stabilizer in polyvinyl chloride (PVC) plastics. ESBO is a yellowish viscous liquid.

Bis(2-ethylhexyl) terephthalate commonly abbreviated DEHT (Dioctyl terephthalate or DOTP), is an organic compound with the formula C6H4(CO2C8H17)2. It is a non-phthalate plasticizer, being the diester of terephthalic acid and the branched-chain 2-ethylhexanol, which is often generically referred to as octyl. This colorless viscous liquid is used for softening PVC plastics and is known for chemical similarity to general purpose phthalates such as DEHP and DINP, but without any negative regulatory pressure. It possesses very good plasticizing properties and may be used as a direct replacement for DEHP and DINP in many applications.

<span class="mw-page-title-main">DPHP</span> Chemical compound

Di(2-propylheptyl) phthalate (also known as bis(2-propylheptyl) benzene-1,2-dicarboxylate, di(propylheptyl) orthophthalate, or DPHP) is an organic compound with the formula C28H46O4. It is a phthalate and is the diester of phthalic acid and the 10-carbon branched-chain alcohol 2-propylheptanol. This colorless, viscous liquid is used for softening PVC plastics and is a general purpose PVC plasticizer. It possesses very good plasticizing properties and may be used as a direct replacement for DEHP and DINP in many applications.

<span class="mw-page-title-main">Bis(2-ethylhexyl)tetrabromophthalate</span> Chemical compound

Bis(2-ethylhexyl)tetrabromophthalate (or TBPH), is a brominated phthalate derivative with the formula C24H34Br4O4 commonly used as a brominated flame retardant (BFR).

References

  1. 1 2 3 4 BASF Technical Leaflet Hexamoll DINCH
  2. ↑ Zamkowska D, Karwacka A, Jurewicz J, Radwan M (July 2018). "Environmental exposure to non-persistent endocrine disrupting chemicals and semen quality: An overview of the current epidemiological evidence" (PDF). International Journal of Occupational Medicine and Environmental Health. 31 (4): 377–414. doi: 10.13075/ijomeh.1896.01195 . PMID   30160090.
  3. ↑ Innovative plasticizer alternative to phthalates for non-PVC applications
  4. ↑ Patent WO 99/32427, "Verfahren zur Hydrierung von Benzolpolycarbonsäuren oder Derivaten davon unter Verwendung eines Makroporen aufweisenden Katalysators", July 1, 1999, BASF AG
  5. ↑ Flexible vinyls get new non-phthalate plasticizer. (Keeping Up With Additives). (September 1, 2002). Plastics Technology. Allbusiness.com. Accessed 2009-02-12.
  6. ↑ Sarah Varney (February 12, 2009). New Safety Law Doesn't Mean All's Well In Toyland. NPR. Accessed 2009-02-12.
  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 Archived 2018-06-03 at the Wayback Machine 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. ↑ 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
  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)
  11. ↑ 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. Bibcode:2016ER....151..595M. doi:10.1016/j.envres.2016.08.012. PMC   5071161 . PMID   27591839.
  12. ↑ 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. Bibcode:2016ScTEn.541..451B. doi:10.1016/j.scitotenv.2015.09.036. PMID   26410720.
  13. ↑ Lioy, Paul J; Hauser, Russ; Gennings, Chris; Koch, Holger M; Mirkes, Philip E; Schwetz, Bernard A; Kortenkamp, Andreas (2015). "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 . PMID   25944701.
  14. ↑ "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. Archived from the original (PDF) on 2016-10-09.
  15. ↑ 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. PMID   25127563.
  16. ↑ 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).
  17. ↑ 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. Bibcode:2015PLoSO..1038421N. doi: 10.1371/journal.pone.0138421 . ISSN   1932-6203. PMC   4596883 . PMID   26445464.
  18. ↑ Crobeddu, Bélinda; Jutras-Carignan, Antoine; Kolasa, Élise; Mounier, Catherine; Robaire, Bernard; Plante, Isabelle (2022-10-01). "Gestational and Lactational Exposure to the Emergent Alternative Plasticizer 1,2-Cyclohexane Dicarboxylic Acid Diisononyl Ester (DINCH) Impairs Lipid Metabolism to a Greater Extent Than the Commonly Used Di(2-Ethylhexyl) Phthalate (DEHP) in the Adult Rat Mammary Gland". Toxicological Sciences. 189 (2): 268–286. doi:10.1093/toxsci/kfac076. ISSN   1096-6080.
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