Dibutyl phthalate

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Dibutyl phthalate
Dibutyl phthalate.svg
Dibutyl phthalate 3D balls.png
Names
Preferred IUPAC name
Dibutyl benzene-1,2-dicarboxylate
Other names
Dibutyl phthalate
Di-n-butyl phthalate
Butyl phthalate, dibasic (2:1)
n-Butyl phthalate
1,2-Benzenedicarboxylic acid dibutyl ester
o-Benzenedicarboxylic acid dibutyl ester
DBP
Palatinol C
Elaol
Dibutyl 1,2-benzene-dicarboxylate
Identifiers
3D model (JSmol)
1914064
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.001.410 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 201-557-4
262569
KEGG
PubChem CID
RTECS number
  • TI0875000
UNII
  • InChI=1S/C16H22O4/c1-3-5-11-19-15(17)13-9-7-8-10-14(13)16(18)20-12-6-4-2/h7-10H,3-6,11-12H2,1-2H3 Yes check.svgY
    Key: DOIRQSBPFJWKBE-UHFFFAOYSA-N X mark.svgN
  • CCCCOC(=O)c1ccccc1C(=O)OCCCC
Properties
C16H22O4
Molar mass 278.348 g·mol−1
AppearanceColorless liquid
Odor aromatic
Density 1.05 g/cm3 at 20 °C
Melting point −35 °C (−31 °F; 238 K)
Boiling point 340 °C (644 °F; 613 K)
13 mg/L (25 °C)
log P 4.72
Vapor pressure 0.00007 mmHg (20 °C) [1]
-175.1·10−6 cm3/mol
Pharmacology
P03BX03 ( WHO )
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
N), Harmful (Xi)
GHS labelling:
GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
Danger
H360Df, H400
P201, P202, P273, P281, P308+P313, P391, P405, P501
NFPA 704 (fire diamond)
NFPA 704.svgHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Flash point 157 °C (315 °F; 430 K) (closed cup)
402 °C (756 °F; 675 K)
Explosive limits 0.5 - 3.5%
Lethal dose or concentration (LD, LC):
5289 mg/kg (oral, mouse)
8000 mg/kg (oral, rat)
10,000 mg/kg (oral, guinea pig) [2]
4250 mg/m3 (rat)
25000 mg/m3 (mouse, 2 hr) [2]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 5 mg/m3 [1]
REL (Recommended)
TWA 5 mg/m3 [1]
IDLH (Immediate danger)
4000 mg/m3 [1]
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 ?)

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. [3]

Production and use

DBP is produced by the reaction of n-butanol with phthalic anhydride. [3] DBP is an important plasticizer that enhances the utility of some major engineering plastics, such as PVC. Such modified PVC is widely used in plumbing for carrying sewerage and other corrosive materials. [3]

Degradation

Hydrolysis of DBP leads to phthalic acid and 1-butanol. [4] Monobutyl phthalate (MBP) is its major metabolite. [5]

Biodegradation

Biodegradation by microorganisms represents one route for remediation of DBP. For example, Enterobacter species can biodegrade municipal solid waste—where the DBP concentration can be observed at 1500 ppm—with a half-life of 2–3 hours. In contrast, the same species can break down 100% of dimethyl phthalate after a span of six days. [6] The white rot fungus Polyporus brumalis degrades DBP. [7] DBP is leached from landfills. [8]

Physical properties relevant to biodegradation

As reflected by its octanol-water partition coefficient of around 4, it is lipophilic, which means that it is not readily mobilized (dissolved by) water. Nonetheless, dissolved organic compounds (DOC) increase its mobility in landfills. [9] [10]

DBP has a low vapor pressure of 2.67 x 10−3 Pa. Thus DBP does not evaporate readily (hence its utility as a plasticizer). [11] The Henry's Law constant is 8.83 x 10−7 atm-m3/mol. [4]

Legislation

DBP is regarded as an endocrine disruptor. [12]

European Union

The use of this substance in cosmetics, including nail polishes, is banned in the European Union under Directive 76/768/EEC 1976. [13]

The use of DBP has been restricted in the European Union for use in children's toys since 1999. [14]

An EU Risk Assessment has been conducted on DBP and the outcome has now been published in the EU Official Journal. To eliminate a potential risk to plants in the vicinity of processing sites and workers through inhalation, measures are to be taken within the framework of the IPPC Directive (96/61/EC) and the Occupational Exposure Directive (98/24/EC) [15] Also includes the 2004 addendum.

Based on urine samples from people of different ages, the European Commission Scientific Committee on Health and Environmental Risks (SCHER) concluded that total exposures to DBP should be further reduced. [16]

Under European Union Directive 2011/65/EU [17] revision 2015/863, [18] DBP is limited to max 1000 ppm concentration in any homogenous material.

United States

Dibutyl phthalate (DBP) is one of the six phthalic acid esters found on the Priority Pollutant List, which consists of pollutants regulated by the United States Environmental Protection Agency (U.S. EPA). [19]

DBP was added to the California Proposition 65 (1986) list of suspected teratogens in November 2006. It is a suspected endocrine disruptor. [12] It was used in many consumer products, e.g., nail polish, but such usages has declined since around 2006. It was banned in children's toys, in concentrations of 1000 ppm or greater, under section 108 of the Consumer Product Safety Improvement Act of 2008 (CPSIA).

Safety

Phthalates are noncorrosive with low acute toxicity. [3]

See also

Related Research Articles

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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). Note that while phthalates are usually plasticizers, not all plasticizers are phthalates. The two terms are specific and unique and cannot be 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">Cosmetology</span> Study and application of beauty treatment

Cosmetology is the study and application of beauty treatment. Branches of specialty include hairstyling, skin care, cosmetics, manicures/pedicures, non-permanent hair removal such as waxing and sugaring, and permanent hair removal processes such as electrology and intense pulsed light (IPL).

<span class="mw-page-title-main">Ethyl acetate</span> Organic compound (CH₃CO₂CH₂CH₃)

Ethyl acetate is the organic compound with the formula CH3CO2CH2CH3, simplified to C4H8O2. This colorless liquid has a characteristic sweet smell and is used in glues, nail polish removers, and in the decaffeination process of tea and coffee. Ethyl acetate is the ester of ethanol and acetic acid; it is manufactured on a large scale for use as a solvent.

<span class="mw-page-title-main">Ethylbenzene</span> Hydrocarbon compound; precursor to styrene and polystyrene

Ethylbenzene is an organic compound with the formula C6H5CH2CH3. It is a highly flammable, colorless liquid with an odor similar to that of gasoline. This monocyclic aromatic hydrocarbon is important in the petrochemical industry as a reaction intermediate in the production of styrene, the precursor to polystyrene, a common plastic material. In 2012, more than 99% of ethylbenzene produced was consumed in the production of styrene.

<span class="mw-page-title-main">2,4-Dinitrotoluene</span> Organic chemical compound

2,4-Dinitrotoluene (DNT) or dinitro is an organic compound with the formula C7H6N2O4. This pale yellow crystalline solid is well known as a precursor to trinitrotoluene (TNT) but is mainly produced as a precursor to toluene diisocyanate.

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

Isobutanol (IUPAC nomenclature: 2-methylpropan-1-ol) is an organic compound with the formula (CH3)2CHCH2OH (sometimes represented as i-BuOH). This colorless, flammable liquid with a characteristic smell is mainly used as a solvent either directly or as its esters. Its isomers are 1-butanol, 2-butanol, and tert-butanol, all of which are important industrially.

<span class="mw-page-title-main">Allyl alcohol</span> Organic compound (CH2=CHCH2OH)

Allyl alcohol is an organic compound with the structural formula CH2=CHCH2OH. Like many alcohols, it is a water-soluble, colourless liquid. It is more toxic than typical small alcohols. Allyl alcohol is used as a raw material for the production of glycerol, but is also used as a precursor to many specialized compounds such as flame-resistant materials, drying oils, and plasticizers. Allyl alcohol is the smallest representative of the allylic alcohols.

<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">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">Propylene glycol dinitrate</span> Chemical compound

Propylene glycol dinitrate (PGDN, 1,2-propylene glycol dinitrate, or 1,2-propanediol dinitrate) is an organic chemical, an ester of nitric acid and propylene glycol. It is structurally similar to nitroglycerin, except that it has one fewer nitrate group. It is a characteristically and unpleasantly smelling colorless liquid, which decomposes at 121 °C, below its boiling point. It is flammable and explosive. It is shock-sensitive and burns with a clean flame producing water vapor, carbon monoxide, and nitrogen gas.

<span class="mw-page-title-main">1-Butanol</span> Chemical compound

1-Butanol, also known as butan-1-ol or n-butanol, is a primary alcohol with the chemical formula C4H9OH and a linear structure. Isomers of 1-butanol are isobutanol, butan-2-ol and tert-butanol. The unmodified term butanol usually refers to the straight chain isomer.

<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">Glycidol</span> Chemical compound

Glycidol is an organic compound that contains both epoxide and alcohol functional groups. Being bifunctional, it has a variety of industrial uses. The compound is a slightly viscous liquid that is slightly unstable and is not often encountered in pure form.

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

Ethyl acrylate is an organic compound with the formula CH2CHCO2CH2CH3. It is the ethyl ester of acrylic acid. It is a colourless liquid with a characteristic acrid odor. It is mainly produced for paints, textiles, and non-woven fibers. It is also a reagent in the synthesis of various pharmaceutical intermediates.

<span class="mw-page-title-main">1,2-Cyclohexane dicarboxylic acid diisononyl ester</span> Chemical compound

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.

<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.

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

Monobutyl phthalate (MBP) is an organic compound with the condensed structural formula CH3(CH2)3OOCC6H4COOH. It is a white solid that features both an butyl ester group and a carboxylic acid group. It is the major metabolite of dibutyl phthalate. Like many phthalates, MBP has attracted attention as a potential endocrine disruptor.

References

  1. 1 2 3 4 NIOSH Pocket Guide to Chemical Hazards. "#0187". National Institute for Occupational Safety and Health (NIOSH).
  2. 1 2 "Dibutyl Phthalate". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  3. 1 2 3 4 Peter M. Lorz, Friedrich K. Towae, Walter Enke, Rudolf Jäckh, Naresh Bhargava, Wolfgang Hillesheim "Phthalic Acid and Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry, 2007, Wiley-VCH, Weinheim. doi : 10.1002/14356007.a20_181.pub2
  4. 1 2 Huang, Jingyu; Nkrumah, Philip N.; Li, Yi; Appiah-Sefah, Gloria (2013). Reviews of Environmental Contamination and Toxicology Volume 224. Reviews of Environmental Contamination and Toxicology. Vol. 224. Springer, New York, NY. pp. 39–52. doi:10.1007/978-1-4614-5882-1_2. ISBN   9781461458814. PMID   23232918.
  5. ↑ Hu Y, Dong C, Chen M, Chen Y, Gu A, Xia Y, Sun H, Li Z, Wang Y (August 2015). "Effects of monobutyl phthalate on steroidogenesis through steroidogenic acute regulatory protein regulated by transcription factors in mouse Leydig tumor cells". J Endocrinol Invest. 38 (8): 875–84. doi:10.1007/s40618-015-0279-6. PMID   25903692. S2CID   21965989.
  6. ↑ Abdel daiem, Mahmoud M.; Rivera-Utrilla, José; Ocampo-Pérez, Raúl; Méndez-Díaz, José D.; Sánchez-Polo, Manuel (2012). "Environmental impact of phthalic acid esters and their removal from water and sediments by different technologies – A review". Journal of Environmental Management. 109: 164–178. doi:10.1016/j.jenvman.2012.05.014. PMID   22796723.
  7. ↑ Ishtiaq Ali, Muhammad (2011). Microbial degradation of polyvinyl chloride plastics (PDF) (PhD). Quaid-i-Azam University. p. 48. Archived from the original (PDF) on 24 December 2013. Retrieved 23 December 2013.
  8. ↑ Kjeldsen, Peter; Barlaz, Morton A.; Rooker, Alix P.; Baun, Anders; Ledin, Anna; Christensen, Thomas H. (1 October 2002). "Present and Long-Term Composition of MSW Landfill Leachate: A Review". Critical Reviews in Environmental Science and Technology. 32 (4): 297–336. doi:10.1080/10643380290813462. ISSN   1064-3389. S2CID   53553742.
  9. ↑ Christensen, Thomas H; Kjeldsen, Peter; Bjerg, Poul L; Jensen, Dorthe L; Christensen, Jette B; Baun, Anders; Albrechtsen, Hans-Jørgen; Heron, Gorm (2001). "Biogeochemistry of landfill leachate plumes". Applied Geochemistry. 16 (7–8): 659–718. Bibcode:2001ApGC...16..659C. doi:10.1016/s0883-2927(00)00082-2.
  10. ↑ Bauer, M.J.; Herrmann, R. (2 July 2016). "Dissolved organic carbon as the main carrier of phthalic acid esters in municipal landfill leachates". Waste Management & Research. 16 (5): 446–454. doi:10.1177/0734242x9801600507. S2CID   98236129.
  11. ↑ Donovan, Stephen F. (1996). "New method for estimating vapor pressure by the use of gas chromatography". Journal of Chromatography A. 749 (1–2): 123–129. doi:10.1016/0021-9673(96)00418-9.
  12. 1 2 "National Report on Human Exposure to Environmental Chemicals". Centers for Disease Control and Prevention, U.S. Department of Health and Human Services. 2021. doi:10.15620/cdc:105345. S2CID   241013949 . Retrieved 14 March 2009.{{cite journal}}: Cite journal requires |journal= (help)
  13. ↑ EU Council Directive 76/768/EEC of 27 July 1976 on the approximation of the laws of the Member States relating to cosmetic products
  14. ↑ Ban of phthalates in childcare articles and toys, press release IP/99/829, 10 November 1999
  15. ↑ "European Union Risk Assessment Report" (PDF). Archived from the original (PDF) on 21 January 2016. Retrieved 2 January 2017.
  16. ↑ "Phthalates in school supplies". GreenFacts Website. Retrieved 10 June 2009.
  17. ↑ Directive 2011/65/EU of the European Parliament and of the Council of 8 June 2011 on the restriction of the use of certain hazardous substances in electrical and electronic equipment Text with EEA relevance
  18. ↑ Commission Delegated Directive (EU) 2015/863 of 31 March 2015 amending Annex II to Directive 2011/65/EU of the European Parliament and of the Council as regards the list of restricted substances
  19. ↑ Gao, Da-Wen; Wen, Zhi-Dan (2016). "Phthalate esters in the environment: A critical review of their occurrence, biodegradation, and removal during wastewater treatment processes". Science of the Total Environment. 541: 986–1001. Bibcode:2016ScTEn.541..986G. doi:10.1016/j.scitotenv.2015.09.148. PMID   26473701.
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