Bisphenol Aのソースを表示

{{Short description|Chemicals used in plastics manufacturing}}
{{cs1 config|name-list-style=vanc|display-authors=3}}
{{Good article}}
{{Use dmy dates|date=December 2020}}
{{Chembox
|Watchedfields = changed
|verifiedrevid = 477162965
|Name = Bisphenol&nbsp;A
|ImageFile1_Ref = {{chemboximage|correct|??}}
|ImageFile1 = Bisphenol-A-Skeletal.svg
|ImageSize1 = 240px
|ImageFile2 = Bisphenol A.png
|ImageSize2 = 180px
|ImageName = Bisphenol A
|PIN = 4,4′-(Propane-2,2-diyl)diphenol
|OtherNames = {{unbulleted list|Bisphenol acetone|BPA|Diphenylolpropane|''p'',''p''-Isopropylidenebisphenol|2,2-Bis(4-hydroxyphenyl)propane|2,2-Di(4-phenylol)propane}}
|Section1={{Chembox Identifiers
|IUPHAR_ligand = 7865
|ChEBI_Ref = {{ebicite|correct|EBI}}
|ChEBI = 33216
|DrugBank_Ref = {{drugbankcite|correct|drugbank}}
|DrugBank = DB06973
|SMILES = Oc1ccc(cc1)C(c2ccc(O)cc2)(C)C
|UNII_Ref = {{fdacite|correct|FDA}}
|UNII = MLT3645I99
|KEGG_Ref = {{keggcite|correct|kegg}}
|KEGG = C13624
|InChI = 1/C15H16O2/c1-15(2,11-3-7-13(16)8-4-11)12-5-9-14(17)10-6-12/h3-10,16-17H,1-2H3
|InChIKey = IISBACLAFKSPIT-UHFFFAOYAI
|SMILES1 = CC(C)(c1ccc(cc1)O)c2ccc(cc2)O
|ChEMBL_Ref = {{ebicite|correct|EBI}}
|ChEMBL = 418971
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|StdInChI = 1S/C15H16O2/c1-15(2,11-3-7-13(16)8-4-11)12-5-9-14(17)10-6-12/h3-10,16-17H,1-2H3
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
|StdInChIKey = IISBACLAFKSPIT-UHFFFAOYSA-N
|CASNo = 80-05-7
|CASNo_Ref = {{cascite|correct|CAS}}
|PubChem = 6623
|EINECS = 201-245-8
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|ChemSpiderID = 6371
|RTECS = SL6300000
|UNNumber = 2430
}}
|Section2={{Chembox Properties
|C=15 | H=16 | O=2
|Appearance = White solid
|Odour = Phenolic, medical
|Density = 1.217 g/cm<sup>3</sup><ref>{{cite journal |last1=Lim |first1=Caitlin F. |last2=Tanski |first2=Joseph M. |title=Structural Analysis of Bisphenol-A and its Methylene, Sulfur, and Oxygen Bridged Bisphenol Analogs |journal=Journal of Chemical Crystallography |date=3 August 2007 |volume=37 |issue=9 |pages=587–595 |doi=10.1007/s10870-007-9207-8|bibcode=2007JCCry..37..587L |s2cid=97284173 }}</ref>
|Solubility = 0.3 g/L (25&nbsp;°C)<ref name=water-solubility>{{cite journal |last1=Shareef |first1=Ali |last2=Angove |first2=Michael J. |last3=Wells |first3=John D. |last4=Johnson |first4=Bruce B. |title=Aqueous Solubilities of Estrone, 17β-Estradiol, 17α-Ethynylestradiol, and Bisphenol A |journal=Journal of Chemical & Engineering Data |date=11 May 2006 |volume=51 |issue=3 |pages=879–881 |doi=10.1021/je050318c}}</ref>
|MeltingPtC = 155
|MeltingPt_ref =<ref name=mbt-mpt>{{cite journal |last1=Mitrofanova |first1=S. E. |last2=Bakirova |first2=I. N. |last3=Zenitova |first3=L. A. |last4=Galimzyanova |first4=A. R. |last5=Nefed'ev |first5=E. S. |title=Polyurethane varnish materials based on diphenylolpropane |journal=Russian Journal of Applied Chemistry |date=September 2009 |volume=82 |issue=9 |pages=1630–1635 |doi=10.1134/S1070427209090225|s2cid=98036316 }}</ref>
|BoilingPtC = 250-252
|BoilingPt_notes = at {{convert|13|Torr|atm}}
|BoilingPt_ref =<ref name=mbt-mpt />
|LogP = 3.41<ref>{{cite journal |last1=Robinson |first1=Brian J. |last2=Hui |first2=Joseph P.M. |last3=Soo |first3=Evelyn C. |last4=Hellou |first4=Jocelyne |title=Estrogenic Compounds in Seawater and Sediment from Halifax Harbour, Nova Scotia, Canada |journal=Environmental Toxicology and Chemistry |date=2009 |volume=28 |issue=1 |pages=18–25 |doi=10.1897/08-203.1|pmid=18702564 |bibcode=2009EnvTC..28...18R |s2cid=13528747 }}</ref>
|VaporPressure = {{nowrap|5×10<sup>−6</sup> Pa}} (25&nbsp;°C)<ref>{{cite web|url=http://www.speclab.com/compound/c80057.htm|website=speclab.com|title=Chemical Fact Sheet – Cas #80057 CASRN 80-05-7|date=1 April 2012|access-date=14 June 2012|archive-url=https://web.archive.org/web/20120212033315/http://www.speclab.com/compound/c80057.htm|archive-date=12 February 2012|url-status=dead}}</ref>
}}
|Section3={{Chembox Hazards
|Hazards_ref = <ref name="Sigma">{{Sigma-Aldrich|id=239658|name=Bisphenol A|access-date=22-05-2022}}</ref>
|NFPA-H = 2
|NFPA-F = 1
|NFPA-R = 0
|GHSPictograms = {{GHS05}}{{GHS07}}{{GHS08}}{{GHS09}}
|GHSSignalWord = Danger
|HPhrases = {{H-phrases|317|318|335|360|H411}}<ref name="Sigma" />
|PPhrases = {{P-phrases|201|202|261|273|302+352|304+340|305+351+338|308+313|333+313|363|403+233}}<ref name="Sigma" />
|FlashPtC = 227 
|FlashPt_ref =<ref name="Sigma"/>
|AutoignitionPtC = 510 
|AutoignitionPt_ref=<ref name="Sigma"/>
}}
}}
'''Bisphenol A''' ('''BPA''') is a [[chemical compound]] primarily used in the manufacturing of various [[plastic]]s. It is a colourless solid which is [[Solubility|soluble]] in most common organic [[solvent]]s, but has very poor solubility in water.<ref name=water-solubility/><ref name="Fiege" /> BPA is produced on an industrial scale by the [[condensation reaction]] of [[phenol]] and [[acetone]]. Global production in 2022 was estimated to be in the region of 10 million tonnes.<ref name=production />

BPA's largest single application is as a [[co-monomer]] in the production of [[polycarbonate]]s, which accounts for 65–70% of all BPA production.<ref name=EU2008 /><ref name="Tom2021"/> The manufacturing of [[epoxy resin]]s and [[vinyl ester resin]]s account for 25–30% of BPA use.<ref name=EU2008/><ref name="Tom2021" /> The remaining 5% is used as a major component of several [[high-performance plastics]], and as a minor additive in [[PVC]], [[polyurethane]], [[thermal paper]], and several other materials. It is not a [[plasticizer]],<ref>{{cite book |doi=10.1002/14356007.a20_439|chapter=Plasticizers|title=Ullmann's Encyclopedia of Industrial Chemistry|year=2000| vauthors = Cadogan DF, Howick CJ |isbn=3527306730}}</ref> although it is often wrongly labelled as such.

The health effects of BPA have been the subject of prolonged public and scientific debate.<ref name=WHO /><ref name=German2011 /><ref name=GLP /> BPA is a [[xenoestrogen]], exhibiting hormone-like properties that mimic the effects of [[estrogen]] in the body.<ref>{{cite journal| vauthors = Egan M |title=Sarah A. Vogel. Is It Safe? BPA and the Struggle to Define the Safety of Chemicals|location=Berkeley|publisher=University of California Press |date=2013 |journal=Isis |volume=105 |issue=1 |pages=254 |doi=10.1086/676809 |issn=0021-1753}}</ref> Although the effect is very weak,<ref name=Xenochemicals /> the pervasiveness of BPA-containing materials raises concerns, as exposure is effectively lifelong.  Many BPA-containing materials are non-obvious but commonly encountered,<ref name="Covaci">{{cite journal | vauthors = Geens T, Aerts D, Berthot C, Bourguignon JP, Goeyens L, Lecomte P, Maghuin-Rogister G, Pironnet AM, Pussemier L, Scippo ML, Van Loco J, Covaci A | title = A review of dietary and non-dietary exposure to bisphenol-A | journal = Food and Chemical Toxicology | volume = 50 | issue = 10 | pages = 3725–3740 | date = October 2012 | pmid = 22889897 | doi = 10.1016/j.fct.2012.07.059 | url = https://dipot.ulb.ac.be/dspace/bitstream/2013/195906/1/Elsevier_179533.pdf }}</ref> and include coatings for the inside of [[food can]]s,<ref>{{cite journal | vauthors = Noonan GO, Ackerman LK, Begley TH | title = Concentration of bisphenol A in highly consumed canned foods on the U.S. market | journal = Journal of Agricultural and Food Chemistry | volume = 59 | issue = 13 | pages = 7178–7185 | date = July 2011 | pmid = 21598963 | doi = 10.1021/jf201076f | bibcode = 2011JAFC...59.7178N }}</ref> clothing designs,<ref name="ir.rcees.ac.cn">{{cite journal | vauthors = Xue J, Liu W, Kannan K | title = Bisphenols, Benzophenones, and Bisphenol A Diglycidyl Ethers in Textiles and Infant Clothing | journal = Environmental Science & Technology | volume = 51 | issue = 9 | pages = 5279–5286 | date = May 2017 | pmid = 28368574 | doi = 10.1021/acs.est.7b00701 | bibcode = 2017EnST...51.5279X | url = http://ir.rcees.ac.cn/handle/311016/39260 | access-date = 12 April 2022 | archive-date = 29 December 2022 | archive-url = https://web.archive.org/web/20221229150022/https://ir.rcees.ac.cn/handle/311016/39260 | url-status = dead }}</ref> shop receipts,<ref name=paper1/> and dental fillings.<ref name="teeth">{{cite journal | vauthors = Ahovuo-Saloranta A, Forss H, Walsh T, Nordblad A, Mäkelä M, Worthington HV | title = Pit and fissure sealants for preventing dental decay in permanent teeth | journal = The Cochrane Database of Systematic Reviews | volume = 2017 | pages = CD001830 | date = July 2017 | issue = 7 | pmid = 28759120 | pmc = 6483295 | doi = 10.1002/14651858.CD001830.pub5 }}</ref> BPA has been investigated by public health agencies in many countries, as well as by the [[World Health Organization]].<ref name=WHO /> 

While normal exposure is below the level currently associated with risk, several jurisdictions have taken steps to reduce exposure on a precautionary basis, in particular by banning BPA from baby bottles. There is some evidence that BPA exposure in infants has decreased as a result of this.<ref name="auto"/> BPA-free plastics have also been introduced, which are manufactured using alternative bisphenols such as [[bisphenol S]] and [[bisphenol F]], but there is also controversy around whether these are actually safer.<ref>{{cite journal | vauthors = Thoene M, Dzika E, Gonkowski S, Wojtkiewicz J | title = Bisphenol S in Food Causes Hormonal and Obesogenic Effects Comparable to or Worse than Bisphenol A: A Literature Review | journal = Nutrients | volume = 12 | issue = 2 | pages = 532 | date = February 2020 | pmid = 32092919 | pmc = 7071457 | doi = 10.3390/nu12020532 | doi-access = free }}</ref><ref name=Other>{{cite journal |last1=Chen |first1=Da |last2=Kannan |first2=Kurunthachalam |last3=Tan |first3=Hongli |last4=Zheng |first4=Zhengui |last5=Feng |first5=Yong-Lai |last6=Wu |first6=Yan |last7=Widelka |first7=Margaret |title=Bisphenol Analogues Other Than BPA: Environmental Occurrence, Human Exposure, and Toxicity—A Review |journal=Environmental Science & Technology |date=7 June 2016 |volume=50 |issue=11 |pages=5438–5453 |doi=10.1021/acs.est.5b05387|pmid=27143250 |bibcode=2016EnST...50.5438C}}</ref><ref>{{cite journal |last1=Eladak |first1=Soria |last2=Grisin |first2=Tiphany |last3=Moison |first3=Delphine |last4=Guerquin |first4=Marie-Justine |last5=N'Tumba-Byn |first5=Thierry |last6=Pozzi-Gaudin |first6=Stéphanie |last7=Benachi |first7=Alexandra |last8=Livera |first8=Gabriel |last9=Rouiller-Fabre |first9=Virginie |last10=Habert |first10=René |date=2015 |title=A new chapter in the bisphenol A story: bisphenol S and bisphenol F are not safe alternatives to this compound |journal=Fertility and Sterility |language=en |volume=103 |issue=1 |pages=11–21 |doi=10.1016/j.fertnstert.2014.11.005|pmid=25475787 |doi-access=free }}</ref>