Epoxidized soybean oil

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Epoxidized soybean oil
Names
Other names
ESBO; Epoxidized soya bean oil; ESO
Identifiers
8013-07-8 N
ChemSpider  YesY
Properties
Appearance Light yellow viscous liquid[1]
Density 0.994 g/cm3[1]
Melting point 0 °C (32 °F; 273 K)
Insoluble[1]
Hazards
R-phrases R36 R37 R38 R43
S-phrases S24 S26 S37
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 227 °C (441 °F; 500 K)
600
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 N verify (what isYesY/N?)
Infobox references

Epoxidized soybean oil (ESBO) is a plasticizer used in polyvinyl chloride (PVC) plastics. It serves as a plasticizer and as a scavenger for hydrochloric acid liberated from PVC when the PVC undergoes heat treatment.[2]

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 mg/kg and about 15% of the samples were above 30 mg ESBO/kg food. High migration levels might lead to an intake that exceeds the existing tolerable daily intake of 1 mg/kg body weight/day.

Manufacturing process[edit]

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.[3] 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[edit]

A Swiss survey done in June 2005 had shown that migration of ESBO into foods could reach up to 1,170 mg/kg.[4]

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).[5]

Legislation[edit]

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 mg/kg.[5] However in the case of infant formula and follow-on formula as defined by Directive 91/321/EEC[6] or products containing processed cereal-based foods and baby foods for infants and young children as defined by Directive 96/5/EC,[7] the SML is lowered to 30 mg/kg. This is because babies have higher ratio of food consumption per body weight.

Uses[edit]

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 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.[8]

Toxicity[edit]

The tolerable daily intake (TDI) of ESBO defined by the Scientific Committee on Food (SCF) of the EU is 1 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.[9] According to the conventional European rules for food packaging materials, the TDI became a basis for the SML of 60 mg/kg.

See also[edit]

References[edit]

  1. ^ a b c d MSDS for ESBO, Arkema Inc.
  2. ^ Fankhauser-Noti, Anja; Fiselier, Katell; Biedermann, Sandra; Biedermann, Maurus; Grob, Koni; Armellini, Franz; Rieger, Karl; Skjevrak, Ingun (2005). "Epoxidized soy bean oil (ESBO) migrating from the gaskets of lids into food packed in glass jars". European Food Research and Technology 221 (3–4): 416–422. doi:10.1007/s00217-005-1194-4. 
  3. ^ Holser, Ronald A. (2008). "Transesterification of epoxidized soybean oil to prepare epoxy methyl esters". Industrial Crops and Products 27: 130–132. doi:10.1016/j.indcrop.2007.06.001. 
  4. ^ Fankhauser-Noti, Anja; Biedermann-Brem, Sandra; Grob, Koni (2006). "PVC plasticizers/additives migrating from the gaskets of metal closures into oily food: Swiss market survey June 2005". European Food Research and Technology 223 (4): 447–453. doi:10.1007/s00217-005-0223-7. 
  5. ^ a b EC.europa.eu RAPID ALERT SYSTEM FOR FOOD AND FEED
  6. ^ Commission Directive 91/321/EEC of 14 May 1991 on infant formulae and follow-on formulae, Faolex.fao.org
  7. ^ COMMISSION DIRECTIVE 96/5/EC of 16 February 1996 on processed cereal-based foods and baby foods for infants and young children, Idace.org
  8. ^ Pedersen, G. A.; Jensen, L. K.; Fankhauser, A.; Biedermann, S.; Petersen, J. H.; Fabech, B. (2008). "Migration of epoxidized soybean oil (ESBO) and phthalates from twist closures into food and enforcement of the overall migration limit". Food Additives & Contaminants: Part A 25 (4): 503–510. doi:10.1080/02652030701519088. 
  9. ^ Epoxidised soya bean oil, Bibra-information.co.uk