105-74-8 Usage
Chemical Properties
Dilauroyl peroxide is a tasteless, coarse, white powder .
Dilauroyl peroxide is not a deflagration hazard. However,
it has been judged an intermediate fire hazard by Noller
et al. . When all the physical tests available for this
peroxide are evaluated collectively, it actually ranks as a
low physical hazard .
Uses
Different sources of media describe the Uses of 105-74-8 differently. You can refer to the following data:
1. Lauroyl peroxide acts as a bleaching agent, drying agent for fats, oils and waxes. Further, it serves as a polymerization initiator as well as vulcanizing agent. In addition to this, it plays an important role for high-pressure polyethylene and food used in bleaching agent.
2. Dilauroyl peroxide is produced by reaction of lauroyl chloride with sodium
peroxide. Its major use is as an initiator for vinyl chloride. It is
used as a polymerization agent in the plastics industry and as a
curing agent for rubber. It has also been used as a burnout agent
for acetate yarns. The pharmaceutical industry uses it in topical
creams in combination with antibiotics for acne treatment .
3. Lauroyl peroxide is used as an initiatorfor free-radical polymerization in makingpolyvinyl chloride. Lauroyl peroxide constitutesabout 4% of all organic peroxides consumptionin the United States.
Preparation
Dilauroyl peroxide is the symmetrical peroxide of lauric acid. It is produced by treating lauroyl chloride with hydrogen peroxide in the presence of base:2C11H23COCl + H2O2+ 2NaOH → (C11H23CO2)2 + 2HCl
General Description
Dilauroyl peroxide appears as a white solid with a faint soapy odor. Less dense than water and insoluble in water. Hence floats on water. Melting point 49 °C. Toxic by ingestion and inhalation. Strong skin irritant. Used as bleaching agent, drying agent for fats, oils and waxes, and as a polymerization catalyst.
Air & Water Reactions
Highly flammable. Insoluble in water.
Reactivity Profile
Dilauroyl peroxide is an oxidizing agent. Can ignite organic materials; hence a dangerous fire and explosion risk [Hawley]. Strongly reduced material such as sulfides, nitrides, and hydrides may react explosively. Vigorous reactions with other reducing agents. With charcoal sometimes ignites. [Bretherick, 5th ed., 1995, p. 1194].
Health Hazard
Different sources of media describe the Health Hazard of 105-74-8 differently. You can refer to the following data:
1. Contact with liquid irritates eyes and skin. Ingestion causes irritation of mouth and stomach.
2. Lauroyl peroxide is a mild eye irritant; theirritation from 500 mg/day in rabbits’ eyeswas mild. It is nontoxic. Prolonged exposureto laboratory animals caused tumors at thesite of application. However, the evidence ofcarcinogenicity in animals is inadequate todate.
Fire Hazard
Behavior in Fire: Can increase the severity of a fire. Becomes sensitive to shock when hot. Containers may explode in a fire. May ignite or explode spontaneously if mixed with flammable materials.
Flammability and Explosibility
Notclassified
Carcinogenicity
The International Agency for Research on Cancer has evaluated the carcinogenicity of
lauroyl peroxide. They classified it as a Group 3 material,
which means there is limited or inadequate evidence for
animals and inadequate or absent information for
humans . The carcinogenicity of this peroxide has primarily
been studied using skin applications. After a single
topical application of 10, 20, or 40 mg of lauroyl peroxide,
the epidermal thickness increased markedly. This hyperplasia
was characterized by a sustained production of dark basal
keratinocytes. This peroxide is inactive as a tumor
initiator or as a complete carcinogen. However, it is as
effective as benzoyl peroxide as a skin tumor promoter.
storage
Store in a well-ventilated, cool area, isolatedfrom other chemicals. It is shippedin fiber drums not exceeding 100 lb. Smallamounts may be shipped in 1-lb fiberboardboxes.
Purification Methods
Crystallise it from n-hexane or *benzene and store it below 0o. Potentially EXPLOSIVE. [cf Beilstein 2 IV 1102.]
Waste Disposal
Although lauroyl peroxide is relatively lesshazardous, it is recommended that to handlespills and disposal, the same safety measuresbe followed as those for other hazardousorganic peroxides.
Check Digit Verification of cas no
The CAS Registry Mumber 105-74-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 5 respectively; the second part has 2 digits, 7 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 105-74:
(5*1)+(4*0)+(3*5)+(2*7)+(1*4)=38
38 % 10 = 8
So 105-74-8 is a valid CAS Registry Number.
InChI:InChI=1/C24H46O4/c1-3-5-7-9-11-13-15-17-19-21-23(25)27-28-24(26)22-20-18-16-14-12-10-8-6-4-2/h3-22H2,1-2H3
105-74-8Relevant articles and documents
Alkyl monolayers on silicon prepared from 1-alkenes and hydrogen-terminated silicon
Linford, Matthew R.,Fenter, Paul,Eisenberger, Peter M.,Chidsey, Christopher E. D.
, p. 3145 - 3155 (1995)
High-quality alkyl monolayers on silicon have been prepared from 1-alkenes and hydrogen-terminated Si(111). The 1-alkenes form monolayers upon free-radical initiation with diacyl peroxides. Heat also initiates monolayer formation, although monolayers prepared from heated long-chain 1-alkenes are of lower quality than those prepared with free-radical initiation. Even when a high concentration of diacyl peroxide is used to initiate monolayer formation, the 1-alkene is the primary constituent of the monolayer. Alkynes also form monolayers on silicon when initiated by diacyl-peroxides. X-ray reflectivity shows that the monolayer thickness is of molecular dimensions and that the density is close to that of crystalline hydrocarbons (～90%). Infrared spectroscopy shows that the alkyl chains in the monolayers are densely packed. Infrared dichroism shows that the chains are tilted from the surface normal and twisted about their axes. The wetting properties of the monolayers show that they are methyl terminated. After many weeks of air exposure, the silicon substrate under the monolayers is not significantly oxidized. The monolayers are very stable to boiling chloroform, boiling water, boiling acidic and basic solutions, and fluoride and are at least as stable as similar chain-length monolayers prepared from trichlorosilanes on oxidized silicon. We propose that alkyl chains in the monolayers are bound to the silicon substrate through silicon-carbon bonds and compare a proposed mechanism of bond formation to analogous homogeneous reactions.
-
Beaudet
, p. 1804,1806 (1947)
-
Iron-Catalyzed Regioselective Decarboxylative Alkylation of Coumarins and Chromones with Alkyl Diacyl Peroxides
Jin, Can,Sun, Bin,Xu, Tengwei,Yan, Zhiyang,Zhang, Xun
supporting information, p. 1585 - 1591 (2019/08/07)
A facile iron-catalyzed decarboxylative radical coupling of alkyl diacyl peroxides with coumarins or chromones has been developed, affording a highly efficient approach to synthesize a variety of α-alkylated coumarins and β-alkylated chromones. The reaction proceeded smoothly without adding any ligand or additive and provided the corresponding products containing a wide scope of functional groups in moderate to excellent yields. This protocol was highlighted by its high regioselectivity, readily available starting materials, and operational simplicity.
Peroxide and lauroyl have intermediate in the synthesis of (by machine translation)
-
Paragraph 0013; 0016-0027, (2018/07/30)
The invention discloses peroxide and lauroyl have intermediate in the synthesis method, comprises the following steps: in the reaction container adding lauryl alkyl amide, 3 - methyl pentane solution, the stirring speed is 230 - 260 rpm, control temperature of the solution to 20 - 26 °C, adding aqueous solution, benzyl methyl ether solution, in the 20 - 40 min batch adding chromium acid zinc powder, to continue the reaction 80 - 120 min; then adding sodium sulfate solution, raising the temperature of the solution to 50 - 55 °C, joined four lead acetate, continue to reaction 2 - 3 h, reduce the temperature of the solution to 5 - 9 °C, adding potassium nitrate solution to wash the 20 - 40 min, adding chloropropanes solution to wash the 30 - 50 min, a solution of cyclohexanol in the recrystallization, the dehydrating agent and dehydration, to get finished peroxide and lauroyl. (by machine translation)
