Epoxidized soybean oil

Epoxidized soybean oil (ESBO) is a collection of organic compounds obtained from the epoxidation of soybean oil. It is used as a plasticizer and stabilizer in polyvinyl chloride (PVC) plastics. ESBO is a yellowish viscous liquid.[2]

Epoxidized soybean oil
Names
Other names
ESBO; Epoxidized soya bean oil; ESO
Identifiers
ChemSpider
  • none
ECHA InfoCard 100.029.444
Properties
Appearance Light yellow viscous liquid[1]
Density 0.994 g/cm3[1]
Melting point 0 °C (32 °F; 273 K)[1]
Insoluble[1]
Hazards
R-phrases (outdated) R36 R37 R38 R43
S-phrases (outdated) S24 S26 S37
NFPA 704 (fire diamond)
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilHealth code 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
Flash point 227 °C (441 °F; 500 K)
600 °C (1,112 °F; 873 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Manufacturing process
Epoxidized linolein, a major component of ESBO.

ESBO is manufactured from soybean oil through the process of epoxidation. Polyunsaturated vegetable oils are widely used as precursors to epoxidized oil products because they have high numbers of carbon-carbon double bonds available for epoxidation.[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.[2]

Uses

Food products that are stored in glass jars are usually sealed with gaskets made from PVC. ESBO is one of the additives in the PVC gasket. It serves as a plasticizer and a scavenger for hydrochloric acid released when the PVC degrades thermally, e.g. when the gasket is applied to the lid and food product undergoes sterilization.[4] ESBO is also used in PVC cling films for wrapping foods and toys.

Safety

Food

A Swiss survey in June 2005 showed that (among many other plasticizers exceeding the legal limits) migration of ESBO into foods reached up to 1,170 mg/kg.[5] 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).[6] Enforcement authorities took measures to force producers respecting the legal limits.

Legislation

In Europe, plastics in food contact are regulated by Regulation (EU) 10/2011. It establishes a specific migration limit (SML) for ESBO of 60 mg/kg. However, in the case of PVC gaskets used to seal glass jars containing infant formulae and follow-on formulae as defined by Directive 2006/141/EC or processed cereal-based foods and baby foods for infants and young children as defined by Directive 2006/125/EC, the SML is lowered to 30 mg/kg. This is because babies have higher food consumption per body weight.

Toxicity

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. Repeated oral administration had been shown to affect the liver, kidney, testis and uterus of rats.[7] According to the conventional European rules for food packaging materials, the TDI became a basis for the SML of 60 mg/kg.

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See also

References
  1. MSDS for ESBO, Arkema Inc.
  2. Guenter Sienel; Robert Rieth; Kenneth T. Rowbottom. "Epoxides". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a09_531.
  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. 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. PMID 18348048.
  5. 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.
  6. EC.europa.eu RAPID ALERT SYSTEM FOR FOOD AND FEED
  7. Epoxidised soya bean oil, Bibra-information.co.uk
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