Diisobutyl phthalate

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Diisobutyl phthalate
Diisobutyl Phthalate.png
Diisobutyl phthalate 3D spacefill.png
Names
Preferred IUPAC name
Bis(2-methylpropyl) benzene-1,2-dicarboxylate
Other names
Diisobutyl phthalate
Diisobutyl ester of phthalic acid
1,2-benzenedicarboxylic acid bis(2-methylpropyl)ester
Di(isobutyl) 1,2-benzenedicarboxylate
DIBP
DiBP
Palatinol IC
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.001.412 Edit this at Wikidata
EC Number
  • 201-553-2
KEGG
RTECS number
  • TI1225000
UNII
  • InChI=1S/C16H22O4/c1-11(2)9-19-15(17)13-7-5-6-8-14(13)16(18)20-10-12(3)4/h5-8,11-12H,9-10H2,1-4H3 checkY
    Key: MGWAVDBGNNKXQV-UHFFFAOYSA-N checkY
  • InChI=1/C16H22O4/c1-11(2)9-19-15(17)13-7-5-6-8-14(13)16(18)20-10-12(3)4/h5-8,11-12H,9-10H2,1-4H3
    Key: MGWAVDBGNNKXQV-UHFFFAOYAA
  • O=C(OCC(C)C)c1ccccc1C(=O)OCC(C)C
Properties
C16H22O4
Molar mass 278.35 g/mol
Appearance Colorless viscous liquid
Density 1.038 g/cm3
Melting point −37 °C (−35 °F; 236 K)
Boiling point 320 °C (608 °F; 593 K)
1 mg/l at 20 °C
log P 4.11
Vapor pressure 0.01 Pa at 20 °C
Hazards
Main hazards Harmful (Xn), Dangerous for the environment (N)
R-phrases (outdated) R50/53-R62-R63
S-phrases (outdated) S36/37-S61
NFPA 704 (fire diamond)
2
1
0
Flash point 185 °C (365 °F; 458 K) c.c.
400 °C (752 °F; 673 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Diisobutyl phthalate (DIBP) is prepared by esterification process of isobutanol and phthalic anhydride. Its structural formula is C6H4(COOCH2CH(CH3)2)2.

DIBP is an odorless plasticizer and has excellent heat and light stability. It is the lowest cost plasticizer for cellulose nitrate. DIBP has lower density and freezing point than the related compound dibutyl phthalate (DBP). Otherwise, it has similar properties DBP and can often be used as a substitute for it. Its refractive index is 1.488–1.492 (at 20 °C, D).

Health issues[edit]

The concentration of a metabolite of DIBP, monoisobutyl phthalate (MIBP), has been steadily increasing in the urine of Americans over the period 1999–2008.[1] In 2021, DIBP, along with dextrorphan, was identified in >75% of sludge samples taken from 12 wastewater treatment plants in California. The same study associated this compound with estrogenic activity in vitro. [2]

Products in Taiwan made by Hebo Natural Products Limited (禾博天然產物有限公司) of China contained ginger contaminated with DIBP; 80,000 nutritional supplement capsules made with imported ginger powder were seized by the Public Health Department of Taiwan in June 2011.[3] In addition, soybean extract and olive leaf extract, both in powder form, were contaminated with DIBP and DBP.[4]

See also[edit]

References[edit]

  1. ^ Center for Disease Control Fourth National Report on Human Exposure to Environmental Chemicals, Updated Tables, February 2011 CDC Exposure Report.
  2. ^ Gabrielle P. Black (2021). "Using Estrogenic Activity and Nontargeted Chemical Analysis to Identify Contaminants in Sewage Sludge". Environmental Science & Technology. 55 (10): 6729–6739. Bibcode:2021EnST...55.6729B. doi:10.1021/acs.est.0c07846. PMC 8378343. PMID 33909413.
  3. ^ News, Taiwan (16 June 2011). "Taiwan News Online - Breaking News, Politics, Environment, Immigrants, Travel, and Health". Taiwan News.
  4. ^ http://www.chinapost.com.tw/taiwan/national/national-news/2011/06/15/306275/Plasticizer-found.htmChina Post Archived 2011-06-25 at the Wayback Machine

External links[edit]