Dibutyl phthalate

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 476992795

| ImageFile =Dibutyl_phthalate.svg

| ImageSize =

| ImageFile1 =Dibutyl_phthalate_3D_balls.png

| ImageSize1 =

| PIN = Dibutyl benzene-1,2-dicarboxylate

| OtherNames = 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

|Section1={{Chembox Identifiers

| IUPHAR_ligand = 6295

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 13837319

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 272485

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 2286E5R2KE

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 84-74-2

| EINECS = 201-557-4

| PubChem = 3026

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 34687

| Beilstein = 1914064

| Gmelin = 262569

| DrugBank = DB13716

| SMILES = CCCCOC(=O)c1ccccc1C(=O)OCCCC

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = DOIRQSBPFJWKBE-UHFFFAOYSA-N

| RTECS = TI0875000

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = C14214

}}

|Section2={{Chembox Properties

| C=16 | H=22 | O=4

| Appearance = Colorless liquid

| Odor = aromatic

| Density = 1.05 g/cm³ at 20 °C

| MeltingPtC = -35

| BoilingPtC = 340

| LogP = 4.72

| Solubility = 13 mg/L (25 °C)

| VaporPressure = 0.00007 mmHg (20 °C)

| MagSus = −175.1·10⁻⁶ cm³/mol

}}

|Section6={{Chembox Pharmacology

| ATCCode_prefix = P03

| ATCCode_suffix = BX03

}}

|Section7={{Chembox Hazards

| MainHazards = N), Harmful (Xi)

| NFPA-H = 2

| NFPA-F = 1

| NFPA-R = 0

| NFPA-S =

| GHSPictograms = {{GHS08}}{{GHS09}}

| GHSSignalWord = Danger

| HPhrases = {{H-phrases|360Df|400}}

| PPhrases = {{P-phrases|201|202|273|281|308+313|391|405|501}}

| FlashPtC = 157

| FlashPt_notes = (closed cup)

| AutoignitionPtC = 402

| AutoignitionPt_notes =

| ExploLimits = 0.5 - 3.5%

| PEL = TWA 5 mg/m³{{PGCH|0187}}

| IDLH = 4000 mg/m³

| REL = TWA 5 mg/m³

| LD50 = 5289 mg/kg (oral, mouse)
8000 mg/kg (oral, rat)
10,000 mg/kg (oral, guinea pig){{IDLH|84742|Dibutyl Phthalate}}

| LC50 = 4250 mg/m³ (rat)
25000 mg/m³ (mouse, 2 hr)

}}

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.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}}

Production and use

DBP is produced by the reaction of n-butanol with phthalic anhydride. 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 sewage and other corrosive materials.

Degradation

Hydrolysis of DBP leads to phthalic acid and 1-butanol.{{Cite book|title=Reviews of Environmental Contamination and Toxicology Volume 224|volume=224|last1=Huang|first1=Jingyu|last2=Nkrumah|first2=Philip N.|last3=Li|first3=Yi|last4=Appiah-Sefah|first4=Gloria|date=2013|publisher=Springer, New York, NY|isbn=9781461458814|series=Reviews of Environmental Contamination and Toxicology|pages=39–52|language=en|doi=10.1007/978-1-4614-5882-1_2|pmid = 23232918}} Monobutyl phthalate (MBP) is its major metabolite.{{cite journal | vauthors = Hu Y, Dong C, Chen M, Chen Y, Gu A, Xia Y, Sun H, Li Z, Wang Y | title = Effects of monobutyl phthalate on steroidogenesis through steroidogenic acute regulatory protein regulated by transcription factors in mouse Leydig tumor cells | journal = J Endocrinol Invest | volume = 38 | issue = 8 | pages = 875–84 | date = August 2015 | pmid = 25903692 | doi = 10.1007/s40618-015-0279-6 | s2cid = 21965989 }}

=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.{{Cite journal|last1=Abdel daiem|first1=Mahmoud M.|last2=Rivera-Utrilla|first2=José|last3=Ocampo-Pérez|first3=Raúl|last4=Méndez-Díaz|first4=José D.|last5=Sánchez-Polo|first5=Manuel|title=Environmental impact of phthalic acid esters and their removal from water and sediments by different technologies – A review|journal=Journal of Environmental Management|volume=109|pages=164–178|doi=10.1016/j.jenvman.2012.05.014|pmid=22796723|year=2012}}

The white rot fungus Polyporus brumalis degrades DBP.{{cite thesis|type=PhD|url=http://prr.hec.gov.pk/Thesis/3362H.pdf|first=Muhammad|last=Ishtiaq Ali|title=Microbial degradation of polyvinyl chloride plastics|publisher=Quaid-i-Azam University|year=2011|pages=48|access-date=23 December 2013|archive-date=24 December 2013|archive-url=https://web.archive.org/web/20131224083944/http://prr.hec.gov.pk/Thesis/3362H.pdf|url-status=dead}}

DBP is leached from landfills.{{Cite journal|last1=Kjeldsen|first1=Peter|last2=Barlaz|first2=Morton A.|last3=Rooker|first3=Alix P.|last4=Baun|first4=Anders|last5=Ledin|first5=Anna|last6=Christensen|first6=Thomas H.|date=2002-10-01|title=Present and Long-Term Composition of MSW Landfill Leachate: A Review|journal=Critical Reviews in Environmental Science and Technology|volume=32|issue=4|pages=297–336|doi=10.1080/10643380290813462|s2cid=53553742|issn=1064-3389|url=http://orbit.dtu.dk/en/publications/present-and-longterm-composition-of-msw-landfill-leachate-a-review(9b0b477d-c04a-46a6-98a4-54b71fe1f52f).html}}

=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.{{Cite journal|last1=Christensen|first1=Thomas H|last2=Kjeldsen|first2=Peter|last3=Bjerg|first3=Poul L|last4=Jensen|first4=Dorthe L|last5=Christensen|first5=Jette B|last6=Baun|first6=Anders|last7=Albrechtsen|first7=Hans-Jørgen|last8=Heron|first8=Gorm|title=Biogeochemistry of landfill leachate plumes|journal=Applied Geochemistry|volume=16|issue=7–8|pages=659–718|doi=10.1016/s0883-2927(00)00082-2|year=2001|bibcode=2001ApGC...16..659C}}{{Cite journal|last1=Bauer|first1=M.J.|last2=Herrmann|first2=R.|date=2016-07-02|title=Dissolved organic carbon as the main carrier of phthalic acid esters in municipal landfill leachates|journal=Waste Management & Research|language=en|volume=16|issue=5|pages=446–454|doi=10.1177/0734242x9801600507|s2cid=98236129}}

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).{{Cite journal|last=Donovan|first=Stephen F.|title=New method for estimating vapor pressure by the use of gas chromatography|journal=Journal of Chromatography A|volume=749|issue=1–2|pages=123–129|doi=10.1016/0021-9673(96)00418-9|year=1996}} The Henry's Law constant is 8.83 x 10⁻⁷ atm-m³/mol.

Legislation

DBP is regarded as an endocrine disruptor.{{cite journal | url = https://www.cdc.gov/exposurereport/ | title = National Report on Human Exposure to Environmental Chemicals | year = 2021 | publisher = Centers for Disease Control and Prevention, U.S. Department of Health and Human Services | doi = 10.15620/cdc:105345 | s2cid = 241013949 | access-date = 2009-03-14}}

=European Union=

The use of this substance in cosmetics, including nail polishes, is banned in the European Union under Directive 76/768/EEC 1976.[http://eur-lex.europa.eu/LexUriServ/LexUriServ.do?uri=CELEX:31976L0768:EN:HTML EU Council Directive 76/768/EEC of 27 July 1976 on the approximation of the laws of the Member States relating to cosmetic products]

The use of DBP has been restricted in the European Union for use in children's toys since 1999.[http://europa.eu/rapid/pressReleasesAction.do?reference=IP/99/829&format=HTML&aged=1&language=EN&guiLanguage=en Ban of phthalates in childcare articles and toys], press release IP/99/829, 10 November 1999

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){{Cite web |url=http://www.plasticisers.org/uploads/Risk%20assessments/DBP%20Risk%20Assessment%20Summary.pdf |title=European Union Risk Assessment Report |access-date=2 January 2017 |archive-url=https://web.archive.org/web/20160121015834/http://www.plasticisers.org/uploads/Risk%20assessments/DBP%20Risk%20Assessment%20Summary.pdf |archive-date=21 January 2016 |url-status=dead }} 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.{{cite web | title=Phthalates in school supplies| publisher=GreenFacts Website | access-date=2009-06-10 | url= http://copublications.greenfacts.org/en/phthalates-school-supplies/}}

Under European Union Directive 2011/65/EU [https://eur-lex.europa.eu/legal-content/EN/TXT/?uri=CELEX%3A32011L0065 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] revision 2015/863,[https://eur-lex.europa.eu/legal-content/EN/TXT/?uri=uriserv:OJ.L_.2015.137.01.0010.01.ENG 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] 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).{{Cite journal|last1=Gao|first1=Da-Wen|last2=Wen|first2=Zhi-Dan|title=Phthalate esters in the environment: A critical review of their occurrence, biodegradation, and removal during wastewater treatment processes|journal=Science of the Total Environment|volume=541|pages=986–1001|doi=10.1016/j.scitotenv.2015.09.148|pmid=26473701|year=2016|bibcode=2016ScTEn.541..986G}}

DBP was added to the California Proposition 65 (1986) list of suspected teratogens in November 2006. It is a suspected endocrine disruptor. 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.

References

External links

{{ICSC|0036|00}}
[https://web.archive.org/web/20070420101248/http://www.phthalates.org/pcp_info_sheet.asp Dibutyl Phthalate and Cosmetics]
[http://nj.gov/health/eoh/rtkweb/documents/fs/0773.pdf Hazardous substance fact sheet]
[https://web.archive.org/web/20070926230026/http://www.osha.gov/SLTC/healthguidelines/dibutylphthalate/recognition.html Occupational safety and health guideline for dibutyl phthalate]
[https://www.cdc.gov/niosh/npg/npgd0187.html CDC - NIOSH Pocket Guide to Chemical Hazards]

Category:Plasticizers

Category:Phthalate esters

Category:Endocrine disruptors

Category:Butyl esters