Antioxidant 1010

Antioxidant 1010 Property

Melting point:

115-118 °C (dec.)(lit.)

Boiling point:

779.1°C (rough estimate)

Density 

0.9594 (rough estimate)

refractive index 

1.6390 (estimate)

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly)

pka

11.71±0.40(Predicted)

form 

Solid

color 

White to Off-White

InChI

InChI=1S/C73H108O12/c1-65(2,3)49-33-45(34-50(61(49)78)66(4,5)6)25-29-57(74)82-41-73(42-83-58(75)30-26-46-35-51(67(7,8)9)62(79)52(36-46)68(10,11)12,43-84-59(76)31-27-47-37-53(69(13,14)15)63(80)54(38-47)70(16,17)18)44-85-60(77)32-28-48-39-55(71(19,20)21)64(81)56(40-48)72(22,23)24/h33-40,78-81H,25-32,41-44H2,1-24H3

InChIKey

BGYHLZZASRKEJE-UHFFFAOYSA-N

SMILES

C(COC(=O)CCC1C=C(C(C)(C)C)C(O)=C(C(C)(C)C)C=1)(COC(=O)CCC1C=C(C(C)(C)C)C(O)=C(C(C)(C)C)C=1)(COC(=O)CCC1C=C(C(C)(C)C)C(O)=C(C(C)(C)C)C=1)COC(=O)CCC1C=C(C(C)(C)C)C(O)=C(C(C)(C)C)C=1

LogP

18.832 (est)

CAS DataBase Reference

6683-19-8(CAS DataBase Reference)

EPA Substance Registry System

Pentaerithritol tetrakis[3,5-di-tert-butyl-4-hydroxyhydrocinnamate] (6683-19-8)

Safety

Safety Statements 

22-24/25

WGK Germany 

-

RTECS 

DA8340900

HS Code 

29182900

Toxicity

LD50 unreported in mammal (species unspecified): 10gm/kg

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

Antioxidant 1010 Chemical Properties,Usage,Production

Characterization

Antioxidant 1010– a sterically hindered phenolic antioxidant – is a highly effective, non discoloring stabilizer for organic substrates such as plastics, synthetic fibers, elastomers, adhesives, waxes, oils and fats. It protects these substrates against thermo-oxidative degradation.

Application

Antioxidant 1010 can be applied in polyolefins, such as polyethylene, polypropylene, polybutene and olefin copolymers such as ethylene-vinylacetate copolymers. Also, its use is recommended for the processing of polymers such as polyacetals, polyamides and polyurethanes, polyesters, PVC, styrene homo- and copolymers, ABS, elastomers such as butyl rubber (IIR), SBS, SEBS, EPM and EPDM as well as other synthetic rubbers, adhesives, natural and synthetic tackifier resins, and other organic substrates.

Features/benefits

Antioxidant 1010 has good compatibility, high resistance to extraction and low volatility. It is odorless and tasteless. The product can be used in combination with other additives such as costabilizers (e. g. thioethers, phosphites, phosphonites), light stabilizers and other functional stabilizers.
   

Physical Properties

Health & Safety

Antioxidant 1010 exhibits a very low order of oral toxicity and does not present any abnormal problems in its handling or general use.

Chemical Properties

White powder. Odorless. Soluble in benzene, acetone, chloroform, slightly soluble in ethanol, insoluble in water.

Uses

Pentaerythritol Tetrakis(3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate) is an antioxidant used in food packaging to prevent the spoilage and increase the shelf life of food products. It can be found mainly in food packages made of LDPE, HDPE, PP, PVC and PET.

General Description

Pentaerythritol tetrakis(3,5-di-tert-butyl-4-hydroxyhydrocinnamate) (PT) is a sterically hindered phenolic antioxidant and a heat stabilizer mainly used to enhance the oxidative resistance and protection against the toxicity of solvents. It has a glass transition temperature of 50℃ and can be annealed at room temperature.
PT can be used as an additive to protect biaxially-oriented propylene (BOPP) capacitor film from thermal oxidation on UV exposure. It can also be used as a standard material to study the gas-cluster ion sputtering (GCIS) using X-ray photoelectron microscopy (XPS) and Atomic force microscopy (AFM).

Health effects

No ADME data are available for this compound. The acute oral LD50 of pentaerythritol tetrakis(3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate) in rats and mice is >5000 mg/kg bw. No clinical signs were reported. For acute dermal toxicity the LD50 in rats is >3160 mg/kg bw. Slight erythema and desquamation were noted. The LC50 for inhalation toxicity in rats is >1951 mg/m3 . Ruffled fur and exophthalmus were reported until day 5 after exposure. No human data on acute toxicity are available. Based on tests with rabbits pentaerythritol tetrakis(3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate) is not considered to be a skin or eye irritant. No human data are available. No sensitization potential is found in the guinea-pig in a Maurer optimisation test.

Flammability and Explosibility

Not classified

Synthesis

Under mechanical stirring, 584 g of methyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, 68 g of pentaerythritol, 0.58 g of sodium montmorillonite, and 50 mL of methanol were added to a 1000 mL four-neck flask. A thermometer sleeve was installed and stirring was started. The reaction was heated to 130-140 °C via a heating jacket while nitrogen was charged and the pressure of the reaction system was controlled at 3-4 MPa. After the reaction lasted for 7 h, the reaction was cooled down to 25 °C, filtered and dried to obtain pentaerythritol tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate]. The results were analyzed by liquid chromatography as follows: the absorption peak with a retention time of 2.643 min corresponded to methyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate with 0.43%; the absorption peak with a retention time of 3.29 min corresponded to pentaerythritol tris[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate] with 0.69%; the absorption peak with a retention time of The absorption peak at 3.84 min corresponded to dealkylated pentaerythritol tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate] with 0.55%; the absorption peak with retention time of 4.747 min corresponded to pentaerythritol tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate] with 96.45%. The purity of pentaerythritol tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate] synthesized by this method meets the industrial standard of not less than 94%, and the yield of the product is 98%.

References

[1] Patent: CN106278894, 2017, A. Location in patent: Paragraph 0017; 0018; 0019
[2] Patent: CN106748790, 2017, A. Location in patent: Paragraph 0031; 0032; 0033; 0034; 0035; 0036; 0037-0050
[3] Russian Chemical Bulletin, 2012, vol. 61, # 9, p. 1689 - 1693
[4] Izv. Akad. Nauk, Ser. Khim., 2012, # 9, p. 1673 - 1677,5
[5] Patent: WO2005/42463, 2005, A1. Location in patent: Page/Page column 10