| Revision as of 12:14, 15 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 476647331 of page Dibutyl_phthalate for the Chem/Drugbox validation project (updated: 'KEGG'). |
Latest revision as of 13:32, 4 January 2024 edit Dkapetansky (talk | contribs)Extended confirmed users726 editsmNo edit summary |
| Line 1: |
Line 1: |
|
|
{{Use dmy dates|date=March 2020}} |
|
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
|
|
{{chembox |
|
{{chembox |
|
| Verifiedfields = changed |
|
| Verifiedfields = changed |
|
|
| Watchedfields = changed |
|
| verifiedrevid = 389085864 |
|
|
|
| verifiedrevid = 476992795 |
|
| ImageFile =Dibutyl_phthalate.svg |
|
| ImageFile =Dibutyl_phthalate.svg |
|
| ImageSize = 200px |
|
| ImageSize = |
|
| ImageFile1 = Dibutyl phthalate 3D balls.gif |
|
| ImageFile1 =Dibutyl_phthalate_3D_balls.png |
|
| ImageSize1 = 200px |
|
| ImageSize1 = |
|
| IUPACName = Dibutyl phthalate |
|
| PIN = Dibutyl benzene-1,2-dicarboxylate |
|
| OtherNames = Di-n-butyl phthalate, Butyl phthalate, n-Butyl phthalate, 1,2-Benzenedicarboxylic acid dibutyl ester, o-Benzenedicarboxylic acid dibutyl ester, DBP, Palatinol C, Elaol |
|
| OtherNames = Dibutyl phthalate<br />Di-''n''-butyl phthalate<br />Butyl phthalate, dibasic (2:1)<br />''n''-Butyl phthalate<br />1,2-Benzenedicarboxylic acid dibutyl ester<br />''o''-Benzenedicarboxylic acid dibutyl ester<br />DBP<br />Palatinol C<br />Elaol<br />Dibutyl 1,2-benzene-dicarboxylate |
|
| Section1 = {{Chembox Identifiers |
|
|Section1={{Chembox Identifiers |
|
|
| IUPHAR_ligand = 6295 |
|
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
|
|
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
| ChemSpiderID = 2918 |
|
|
|
| ChemSpiderID = 13837319 |
|
|
| ChEMBL_Ref = {{ebicite|correct|EBI}} |
|
|
| ChEMBL = 272485 |
|
| UNII_Ref = {{fdacite|correct|FDA}} |
|
| UNII_Ref = {{fdacite|correct|FDA}} |
|
| UNII = 2286E5R2KE |
|
| UNII = 2286E5R2KE |
|
| CASNo_Ref = {{cascite|correct|CAS}} |
|
| CASNo_Ref = {{cascite|correct|CAS}} |
|
| CASNo = 84-74-2 |
|
| CASNo = 84-74-2 |
|
| EINECS = 201-557-4 |
|
| EINECS = 201-557-4 |
|
| PubChem = 3026 |
|
| PubChem = 3026 |
|
|
| ChEBI_Ref = {{ebicite|correct|EBI}} |
|
| SMILES = |
|
|
| RTECS = TI0875000 |
|
| ChEBI = 34687 |
|
|
| Beilstein = 1914064 |
|
| KEGG_Ref = {{keggcite|changed|kegg}} |
|
|
|
| Gmelin = 262569 |
|
| KEGG = <!-- blanked - oldvalue: C14214 --> |
|
|
|
| DrugBank = DB13716 |
|
}} |
|
|
|
| SMILES = CCCCOC(=O)c1ccccc1C(=O)OCCCC |
|
| Section2 = {{Chembox Properties |
|
|
|
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
| C=16|H=22|O=4 |
|
|
|
| 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 |
|
| Appearance = Colorless oily liquid |
|
|
|
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
|
| Density = 1.05 g/cm<sup>3</sup> at 20 °C |
|
|
|
| StdInChIKey = DOIRQSBPFJWKBE-UHFFFAOYSA-N |
|
| MeltingPtC = -35 |
|
|
|
| RTECS = TI0875000 |
|
| BoilingPtC = 340 |
|
|
|
| KEGG_Ref = {{keggcite|correct|kegg}} |
|
| LogP = 4.72 |
|
|
|
| KEGG = C14214 |
|
| Solubility = 0.013 g/L |
|
|
}} |
|
}} |
|
| Section3 = {{Chembox Hazards |
|
|Section2={{Chembox Properties |
|
|
| C=16 | H=22 | O=4 |
|
| MainHazards = Dangerous for the environment ('''N'''), Harmful ('''Xi''') |
|
|
|
| Appearance = Colorless liquid |
|
| NFPA-H = 2 |
|
|
| NFPA-F = 1 |
|
| Odor = aromatic |
|
|
| Density = 1.05 g/cm<sup>3</sup> at 20 °C |
|
| NFPA-R = 0 |
|
|
| NFPA-O = |
|
| MeltingPtC = -35 |
|
|
| BoilingPtC = 340 |
|
| RPhrases = {{R50}} {{R61}} {{R62}} |
|
|
|
| LogP = 4.72 |
|
| SPhrases = {{S45}} {{S53}} {{S61}} |
|
|
|
| Solubility = 13 mg/L (25 °C) |
|
| FlashPt = 157 °C (closed cup) |
|
|
|
| VaporPressure = 0.00007 mmHg (20 °C)<ref name=PGCH/> |
|
| Autoignition = 402 °C |
|
|
|
| MagSus = -175.1·10<sup>−6</sup> cm<sup>3</sup>/mol |
|
| ExploLimits = 0.5 - 3.5% |
|
|
|
}} |
|
|
|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/m<sup>3</sup><ref name=PGCH>{{PGCH|0187}}</ref> |
|
|
| IDLH = 4000 mg/m<sup>3</sup><ref name=PGCH/> |
|
|
| REL = TWA 5 mg/m<sup>3</sup><ref name=PGCH/> |
|
|
| LD50 = 5289 mg/kg (oral, mouse)<br/>8000 mg/kg (oral, rat)<br/>10,000 mg/kg (oral, guinea pig)<ref name=IDLH>{{IDLH|84742|Dibutyl Phthalate}}</ref> |
|
|
| LC50 = 4250 mg/m<sup>3</sup> (rat)<br/>25000 mg/m<sup>3</sup> (mouse, 2 hr)<ref name=IDLH/> |
|
}} |
|
}} |
|
}} |
|
}} |
|
|
|
|
|
'''Dibutyl phthalate''' ('''DBP''') is an ] which is commonly used as a ] because of its low toxicity and wide liquid range. With the ] C<sub>6</sub>H<sub>4</sub>(CO<sub>2</sub>C<sub>4</sub>H<sub>9</sub>)<sub>2</sub>, it is a colorless oil, although impurities often render commercial samples yellow.<ref name=Ullmann>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}}</ref> |
|
|
|
|
|
==Production and use== |
|
|
DBP is produced by the reaction of ] with ].<ref name=Ullmann/> 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.<ref name=Ullmann/> |
|
|
|
|
|
==Degradation== |
|
|
Hydrolysis of DBP leads to phthalic acid and ].<ref name=":22">{{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}}</ref> ] (MBP) is its major metabolite.<ref name="pmid25903692">{{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 }}</ref> |
|
|
|
|
|
===Biodegradation=== |
|
|
] by microorganisms represents one route for remediation of DBP. For example, '']'' species can biodegrade municipal solid waste—where the DBP concentration can be observed at 1500 ppm—with a ] of 2–3 hours. In contrast, the same species can break down 100% of dimethyl phthalate after a span of six days.<ref>{{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}}</ref> |
|
|
The white rot fungus '']'' degrades DBP.<ref>{{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}}</ref> |
|
|
DBP is leached from landfills.<ref>{{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}}</ref> |
|
|
|
|
|
===Physical properties relevant to biodegradation=== |
|
|
As reflected by its ] 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 ]s.<ref>{{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}}</ref><ref>{{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}}</ref> |
|
|
|
|
|
DBP has a low ] of 2.67 x 10<sup>−3</sup> Pa. Thus DBP does not evaporate readily (hence its utility as a plasticizer).<ref name=":12">{{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}}</ref> The ] is 8.83 x 10<sup>−7</sup> atm-m<sup>3</sup>/mol.<ref name=":22" /> |
|
|
|
|
|
==Legislation== |
|
|
DBP is regarded as an ].<ref name="urlCDC - National Report on Human Exposure to Environmental Chemicals | CDC">{{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}}</ref> |
|
|
|
|
|
===European Union=== |
|
|
The use of this substance in cosmetics, including nail polishes, is banned in the ] under ] 76/768/EEC 1976.<ref></ref> |
|
|
|
|
|
The use of DBP has been restricted in the European Union for use in children's toys since 1999.<ref>, press release IP/99/829, 10 November 1999</ref> |
|
|
|
|
|
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)<ref>{{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 }}</ref> Also includes the 2004 addendum. |
|
|
|
|
|
Based on urine samples from people of different ages, the European Commission ] (SCHER) concluded that total exposures to DBP should be further reduced.<ref>{{cite web | title=Phthalates in school supplies| publisher=GreenFacts Website | access-date=2009-06-10 | url= http://copublications.greenfacts.org/en/phthalates-school-supplies/}}</ref> |
|
|
|
|
|
Under ] ] 2011/65/EU <ref></ref> revision 2015/863,<ref></ref> 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 ] (U.S. EPA).<ref name=":02">{{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}}</ref> |
|
|
|
|
|
DBP was added to the ] list of suspected ]s in November 2006. It is a suspected ].<ref name="urlCDC - National Report on Human Exposure to Environmental Chemicals | CDC"/> It was used in many consumer products, e.g., ], 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.<ref name=Ullmann/> |
|
|
|
|
|
==See also== |
|
|
* ] |
|
|
* ] |
|
|
* ] (DIBP) |
|
|
* ] |
|
|
|
|
|
==References== |
|
|
{{Reflist}} |
|
|
|
|
|
==External links== |
|
|
* {{ICSC|0036|00}} |
|
|
* |
|
|
* |
|
|
* |
|
|
* |
|
|
|
|
|
{{HealthIssuesOfPlastics}} |
|
|
{{Authority control}} |
|
|
|
|
|
{{DEFAULTSORT:Dibutyl Phthalate}} |
|
|
] |
|
|
] |
|
|
] |
|
|
] |