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Perkadox, chemical name bis (4-tert butylcyclohexyl) peroxydicarbonate(BCHPC), appears as a white to grayish white powder with molecular formula C22H38O6 and CAS 15520-11-3. This powder has a high degree of fineness, is easy to disperse and mix, and provides convenience for its application in industrial production. It is an important organic peroxide with a wide range of applications. It has important applications in polymer industry, adhesive and coating industry, rubber industry, textile industry, and pharmaceutical industry. With the progress of technology and the development of industry, the application fields of bis (4-tert butylcyclohexyl) peroxydicarbonate will continue to expand and deepen.
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Chemical Formula |
C22H38O6 |
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Exact Mass |
398 |
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Molecular Weight |
399 |
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m/z |
398 (100.0%), 399 (23.8%), 400 (2.7%), 400 (1.2%) |
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Elemental Analysis |
C, 66.30; H, 9.61; O, 24.09 |
Perkadox (CAS number 15520-11-3) is an organic peroxide compound with high initiation activity and thermal stability due to its unique molecular structure (containing two peroxide bonds and a tert butyl cyclohexyl substituent). This substance is widely used in industrial production, especially in the fields of polymerization reaction initiation, material cross-linking, and specific chemical synthesis. The following provides a detailed analysis from four dimensions: core usage, technical principles, application scenarios, and security standards.
The core function is to act as an initiator for free radical polymerization reactions, and its mechanism of action is to generate free radicals through decomposition, initiating the chain polymerization of monomer molecules. This substance exhibits excellent performance in the following polymerization systems:
1. Polymerization and copolymerization of vinyl chloride
Application scenario: Vinyl chloride (VC) is a monomer of polyvinyl chloride (PVC), and its polymerization reaction requires strict control of initiator activity to obtain a product with uniform molecular weight distribution. By generating free radicals through decomposition, it is possible to efficiently initiate homopolymerization of vinyl chloride or copolymerization with vinyl acetate (VAc) and vinyl chloride (VDC) to prepare copolymers with specific properties.
Technical advantages: This initiator can decompose under low temperature conditions (such as 40-60 ℃), avoiding side reactions caused by high temperature (such as chain transfer and degradation). At the same time, its decomposition products (such as tert butyl cyclohexanol) do not significantly interfere with the polymerization system, which helps to improve product purity.
Typical case: In the production of vinyl chloride vinyl acetate copolymer (VC VAc), adding 0.1% -0.5% of this substance can significantly improve the heat resistance and flexibility of the copolymer, making it suitable for manufacturing weather resistant pipes and films.
2. Acrylic ester polymerization
Application scenario: The polymerization of acrylic monomers (such as methyl methacrylate MMA, butyl acrylate BA) requires initiators to provide highly active free radicals to control the polymerization rate and molecular weight. Because its decomposition temperature is moderate (about 50-70 ℃), it is often used to prepare acrylate copolymers (such as acrylate lotion and pressure sensitive adhesive).
Technical advantage: This initiator can be compounded with other peroxides (such as benzoyl peroxide BPO) to achieve "cold and hot segmented control" of polymerization reaction by adjusting the decomposition rate, optimizing product performance.
For example, in the polymerization of acrylate lotion, the composite initiator can improve the stability of lotion and reduce the formation of gel.
Typical case: When preparing high solid content acrylic pressure-sensitive adhesive, adding 0.3% bis (4-tert-butylcyclohexyl) peroxydicarbonate can complete the polymerization reaction at 60 ℃, increase the adhesive strength of the product by 20%, and significantly improve the aging resistance.
3. Ethylene polymerization and modification
Application scenario: The polymerization of ethylene (C ₂ H ₄) requires high pressure conditions (100-300 MPa) and efficient initiators to prepare low-density polyethylene (LDPE).
Due to its thermal stability, it can decompose stably in high-pressure reactors and provide continuous free radical flow.
Technical advantages: The decomposition products of the initiator (such as cyclohexane derivatives) have no toxic side effects on the ethylene polymerization system, and their decomposition rate can be precisely controlled by adjusting the pressure (such as from 150 MPa to 250 MPa), thereby optimizing the melt index (MI) and density of the product.
Typical case: Adding 0.05% of LDPE with a melt index of 2.0 g/10min can shorten the polymerization reaction time by 15% and increase the transparency of the product by 10%.
Extended use: Material cross-linking and modification
In addition to triggering polymerization reactions, it can also serve as a crosslinking agent, forming chemical bonds between polymer molecular chains through free radical mechanisms to enhance material properties.
1. Unsaturated polyester crosslinking
Application scenario: Unsaturated polyester (UPR) is a thermosetting resin that requires crosslinking agents (such as peroxides) to copolymerize with monomers such as styrene to form a three-dimensional network structure. Due to its decomposition temperature (about 70-90 ℃) matching the UPR curing process, it is commonly used in the manufacturing of fiberglass products, artificial stone, etc.
Technical advantage: The free radicals generated by the decomposition of this crosslinking agent can simultaneously attack the double bonds of polyester and styrene monomer, achieving "synergistic crosslinking" and improving curing efficiency. For example, in UPR glass fiber composite materials, adding 1.5% of this substance can shorten the curing time from 30 minutes to 20 minutes and increase the bending strength by 15%.
2. Rubber vulcanization promotion
Application scenario: The vulcanization of natural rubber (NR) or synthetic rubber (such as SBR, BR) requires peroxide crosslinking agents to form a crosslinking network.
Due to its decomposition products having no odor, it is commonly used in the manufacturing of food grade rubber products (such as sealing rings and conveyor belts).
Technical advantage: This crosslinking agent decomposes at 120-140 ℃, avoiding the carcinogenic nitrosamines produced by traditional sulfur vulcanization systems and meeting environmental requirements. For example, in SBR rubber vulcanization, adding 2.0% of this product can increase the tensile strength of the vulcanized rubber by 20% and significantly improve its aging resistance.
The peroxide bond (- O-O -) has strong oxidizing properties and can be used as an oxidant to participate in specific organic synthesis reactions.
1. Preparation of ketones by oxidation of alcohols
Reaction mechanism: This substance can oxidize primary alcohols (R-CH ₂ OH) to aldehydes (R-CHO), and further oxidize them to ketones (R-CO-R '). For example, in the reaction of cyclohexanol oxidation to produce cyclohexanone, as an oxidant, efficient conversion is achieved under acidic conditions (such as sulfuric acid catalysis).
Technical advantages: Compared with traditional oxidants such as chromate and potassium permanganate, the oxidation products of this substance are easy to separate (only requiring water washing), and there is no heavy metal pollution, which meets the requirements of green chemistry. For example, in the oxidation reaction of 100 grams of cyclohexanol, adding 1.2 times the equivalent of this substance can achieve a cyclohexanone yield of 95% and a purity of ≥ 99%.
2. Oxidation of sulfides to prepare sulfoxides/sulfones
Reaction mechanism: This substance can oxidize sulfide (R-S-R ') to sulfoxide (R-S (=O) - R') or sulfone (R-S (=O) ₂ - R ').
For example, in the reaction of dimethyl sulfide (DMS) oxidation to prepare dimethyl sulfoxide (DMSO), bis (4-tert-butylcyclohexyl) peroxydicarbonate is used as an oxidant, and quantitative conversion can be achieved at room temperature.
Technical advantages: The reaction conditions are mild (no need for high temperature or high pressure), and the amount of oxidant used is small (1.0-1.1 times equivalent), making it suitable for large-scale production. For example, in a 1-ton DMS oxidation unit, adding 1.05 tons of bis (4-tert-butylcyclohexyl) peroxydicarbonate can achieve a DMSO yield of 98%, and the product purity meets pharmaceutical grade standards (≥ 99.5%).
Perkadox , or BCHPC for short, is a peroxide that is commonly used as a free radical initiator, especially in polymerization reactions. Below are the detailed steps and chemical equations for the synthesis of BCHPC:
C8H17OH + SOCl2 → C8H17Cl + SO2 + HCl
Materials:
- 4-tert-butylcyclohexanol
- Sulfonyl chloride
- Aluminum chloride
Steps:
01
Dissolve 4-tert-butylcyclohexanol in sulfonyl chloride in a dry solvent.
02
Add aluminum chloride and stir the mixture.
03
Heat the mixture until the reaction is complete.
C8H17Cl + H2O2 → C8H17OOH + HCl
Materials:
01
- Chlorinated 4-tert-butylcyclohexanol
02
- Hydrogen peroxide
Advantages of Chain Sprockets
01
Dissolve chlorinated 4-tert-butylcyclohexanol in a suitable solvent.
02
Add hydrogen peroxide gradually.
03
After the reaction is completed, remove hydrogen peroxide by appropriate means.
C8H17OOH + CO2 → C8H17OC(O)OOC(O)C8H17 + H2O
Materials:
01
- Oxidized 4-tert-butylcyclohexyl chloride
02
- Carbon dioxide
Steps:
01
Dissolve oxidized 4-tert-butylcyclohexyl chloride in a suitable solvent.
02
Carry out carbonation reaction by passing carbon dioxide gas.
03
After the reaction is completed, extract and purify BCHPC by appropriate means.
Steps:
01
Dissolve the synthesized BCHPC in a suitable solvent.
02
Perform crystallization purification by appropriate means, such as slow cooling or solvent evaporation.
03
Collect and dry the BCHPC crystals.
In addition to the synthesis methods mentioned above, there are also some other possible synthesis methods, but their feasibility, efficiency, and yield may differ in practice. Here are some possible methods:
1. Oxidation of 4-tert butylcyclohexanol:
Oxidants can be used to oxidize 4-tert butylcyclohexanol to the corresponding peroxide. Common oxidants include hydrogen peroxide, benzoyl peroxide, thiol peroxide chloride, etc.
2. Chlorination of 4-tert butylcyclohexyl alcohol:
In the synthesis step of 4-tert butylcyclohexanol, different chlorinating agents or conditions can be attempted to achieve chlorination reaction.
3. Direct carbonation of 4-tert butylcyclohexanol:
It can be considered to directly react 4-tert butylcyclohexanol with carbonate compounds (such as dimethyl carbonate) to generate BCHPC. This method may require the use of catalysts or special reaction conditions.
4. Other Perkadox synthesis routes:
In addition to oxidizing 4-tert butylcyclohexanol, other compounds can also be used as starting materials to synthesize BCHPC through appropriate reactions. This may involve multi-step synthesis routes and require careful design and optimization of reaction conditions.
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