Epoxidized soybean oil: Difference between revisions

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'''Epoxidized soybean oil''', better known by its acronym, ESBO, is a [[plasticizer]] used in [[polyvinyl chloride]] (PVC) [[plastic]]s. It serves as a plasticizer and as a scavenger for [[hydrochloric acid]] liberated from PVC when the PVC undergoes heat treatment.<ref>{{cite journal | doi = 10.1007/s00217-005-1194-4 | title = Epoxidized soy bean oil (ESBO) migrating from the gaskets of lids into food packed in glass jars | year = 2005 | last1 = Fankhauser-Noti | first1 = Anja | last2 = Fiselier | first2 = Katell | last3 = Biedermann | first3 = Sandra | last4 = Biedermann | first4 = Maurus | last5 = Grob | first5 = Koni | last6 = Armellini | first6 = Franz | last7 = Rieger | first7 = Karl | last8 = Skjevrak | first8 = Ingun | journal = European Food Research and Technology | volume = 221 | issue = 3–4 | pages = 416–422}}</ref>

A few EU surveys have shown fairly high levels of ESBO in foods, in which about 4% were above the current specific migration limit (SML) for ESBO of 60&nbsp;mg/kg and about 15% of the samples were above 30&nbsp;mg ESBO/kg food. High migration levels might lead to an intake that exceeds the existing Tolerable Daily Intake of 1&nbsp;mg/kg body weight/day.

[[File:Epoxidized linolein.svg|thumb|right|Epoxidized [[linolein]], a major component of ESBO]]

ESBO is manufactured from soybean oil through the process of [[epoxidation]]. The reason why vegetable oils are widely used as plasticizers is because the high numbers of carbon-carbon double bonds present in vegetable oils make them a good target for manipulation into some other useful products like in this case - from soybean oil into epoxidized soybean oil.<ref>{{cite journal | doi = 10.1016/j.indcrop.2007.06.001 | title = Transesterification of epoxidized soybean oil to prepare epoxy methyl esters | year = 2008 | last1 = Holser | first1 = Ronald A. | journal = Industrial Crops and Products | volume = 27 | pages = 130–132}}</ref> The [[epoxide]] group is more reactive than double bond, thus providing a more energetically favorable site for reaction and making the oil a good hydrochloric acid scavenger and plasticizer. Usually a [[peroxide]] or a [[peracid]] is used to add an atom of oxygen and convert the -C=C- bond to an epoxide group.

Metal closures incorporate a ring-shaped gasket formed from a bead of liquid plastisol containing up to 40% ESBO which is moulded into the correct profile in the closure shell using a hot punch, then fused by passing through an oven at 200°C for 90 seconds. PVC starts to break down at this high temperature and releases hydrogen chloride. ESBO functions as a stabilizer to scavenge this hydrogen chloride to prevent the autocatalytic breakdown of the polymer. It also functions as a plasticizer.

==Food safety alert ==

A Swiss survey done in June 2005 had shown that migration of ESBO into foods could reach up to 1,170&nbsp;mg/kg.<ref>{{cite journal | doi = 10.1007/s00217-005-0223-7 | title = PVC plasticizers/additives migrating from the gaskets of metal closures into oily food: Swiss market survey June 2005 | year = 2006 | last1 = Fankhauser-Noti | first1 = Anja | last2 = Biedermann-Brem | first2 = Sandra | last3 = Grob | first3 = Koni | journal = European Food Research and Technology | volume = 223 | issue = 4 | pages = 447–453}}</ref>

Rapid Alert System in Food and Feed (RASFF) had also reported cases of food product rejection in EU for exceeding SML under EU Legislation (EC/2002/72).<ref name=rapidalert>[http://ec.europa.eu/food/food/rapidalert/reports/week40-2007_en.pdf EC.europa.eu RAPID ALERT SYSTEM FOR FOOD AND FEED]</ref>

==Legislation==

In Europe, plastics are regulated by the Commission Directive 2002/72/EC which consolidates Commission Directive 90/128/EEC and its seven amendments (Directives 92/39/EEC, 93/9/EEC, 95/3/EEC, 96/11/EEC, 1999/91/EC, 2001/62/EC and 2002/17/EC). These amendments mainly modified the lists of authorized substances such as monomers and additives.

Directive 2002/72/EC establishes a specific migration limit for ESBO of 60&nbsp;mg/kg.<ref name=rapidalert/> However in the case of infant formula and follow-on formula as defined by Directive 91/321/EEC<ref>[http://faolex.fao.org/docs/texts/eur18745.doc Commission Directive 91/321/EEC of 14 May 1991 on infant formulae and follow-on formulae], Faolex.fao.org</ref> or products containing processed cereal-based foods and baby foods for infants and young children as defined by Directive 96/5/EC,<ref>[http://www.idace.org/legislation/cereal%20based%20foods/Dir%2096-5%20WF.pdf COMMISSION DIRECTIVE 96/5/EC of 16 February 1996 on processed cereal-based foods and baby foods for infants and young children], Idace.org</ref> the SML is lowered to 30&nbsp;mg/kg. This is because babies have higher ratio of food consumption per body weight.

Food products that are stored in [[glass]] jars with [[metal]] lids need a [[gasket]] to make a good seal and the gasket is usually made from PVC. It forms an airtight seal preventing [[Microorganism|microbiological]] and other [[contamination]]. ESBO is one of the additives used in the PVC gasket. It serves as a plasticizer and a scavenger for hydrochloric acid released from PVC when the food product undergoes [[Sterilization (microbiology)|sterilization]].<ref>{{cite journal | doi = 10.1080/02652030701519088 | title = Migration of epoxidized soybean oil (ESBO) and phthalates from twist closures into food and enforcement of the overall migration limit | year = 2008 | last1 = Pedersen | first1 = G. A. | last2 = Jensen | first2 = L. K. | last3 = Fankhauser | first3 = A. | last4 = Biedermann | first4 = S. | last5 = Petersen | first5 = J. H. | last6 = Fabech | first6 = B. | journal = Food Additives & Contaminants: Part A | volume = 25 | issue = 4 | pages = 503–510}}</ref>

==Toxicity==

The tolerable daily intake (TDI) of ESBO defined by the Scientific Committee on Food (SCF) of the EU is 1&nbsp;mg/kg body weight. This value is based on a toxicological assessment performed by the British Industrial Biological Research Association (BIBRA) in the late 1997. Repearted oral administration had been shown to affect the liver, kidney, testis and uterus.<ref>[http://www.bibra-information.co.uk/profile-126.html Epoxidised soya bean oil], Bibra-information.co.uk</ref> According to the conventional European rules for food packaging materials, the TDI became a basis for the SML of 60&nbsp;mg/kg.