Tert-Amyl Hydroperoxide

Tert-Amyl Hydroperoxide

Tert-Amyl hydroperoxide is a colorless or slightly yellow transparent liquid.Its CAS number is 3425-61-4.Tert-Amyl hydroperoxide is also known as TAHP.TAHP is a very important intermediate in organic synthesis.The decomposition products of TAHP are mainly Tert-Amyl alcohol and a small amount of acetone, which are non corrosive and do not require high equipment requirements. But most other initiators will form acidic byproducts. Its performance is superior to that of persulfate, CHP and BPO in many aspects.

Product Introduction
Nantong Kezhong Chemical Technology Co., Ltd.:Your Trustworthy Tert-Amyl Hydroperoxide Manufacturer!

Nantong Kezhong Chemical Technology Co., Ltd. is a professional supplier of organic peroxides, acyl chloride series and basic chemicals.The company has self import and export qualification, and is committed to providing competitive products and perfect solutions for users at home and abroad. The products sell well in Chinese Mainland, Chinese Taiwan, Europe, America, India and other countries and regions.

Leading Service
We are committed to constantly innovating our products to provide foreign customers with a large number of high-quality products to exceed customer satisfaction. We can also provide customized services according to customers' requirements such as size,color,appearance,etc.We can provide the most favorable price and high-quality products.

 

Quality Guaranteed
We have been continuously researching and innovating to meet the needs of different customers. At the same time, we always adhere to strict quality control to ensure that the quality of every product meets international standards.

 

Wide Sales Countries
We focus on sales in overseas markets. Our products are exported to Europe, America,Southeast Asia,the Middle East and other regions, and are well received by customers around the world.

 

Various Types of Products
Our products include Organic peroxides: Tert-butyl peroxybenzoate , dibenzoyl peroxide, di-tert-butyl peroxide, tert-butyl hydrogen peroxide, 2,5-dimethyl-2,5-bis (tert-butylperoxy) hexane, and bis (2,4-dichlorobenzoyl peroxide), totaling 5000 tons/year. Acyl chloride series and basic chemicals: acryloyl chloride, methacryloyl chloride, p-chlorobenzoyl chloride, benzophenone (refined grade), oxalyl chloride, benzoyl chloride, etc., totaling 15000 tons/year.

 

Our Related Products
 
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Methacryloyl Chloride | CAS 920-46-7

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Tert-butyl hydroperoxide is also known as TBHP.Its characteristics are good thermal stability, safe use, and easy to control. At temperatures below 50℃, its activity does not change significantly within three months, and there is no need for expensive frozen storage.

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LPO | CAS 105-74-8 | Dilauroyl Peroxide

 

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What is Tert-Amyl Hydroperoxide

 

 

Tert-Amyl hydroperoxide is a colorless or slightly yellow transparent liquid.Its CAS number is 3425-61-4.Tert-Amyl hydroperoxide is also known as TAHP.TAHP is a very important intermediate in organic synthesis.The decomposition products of TAHP are mainly Tert-Amyl alcohol and a small amount of acetone, which are non corrosive and do not require high equipment requirements. But most other initiators will form acidic byproducts. Its performance is superior to that of persulfate, CHP and BPO in many aspects.

 

What to Know About Tert-Amyl Hydroperoxide

Chemical Reactions Analysis
TAHP is a strong oxidizer and is often used as an oxidizing agent in organic synthesis reactions. It can be used to oxidize sulfides, alcohols, ketones, ethers, and other organic compounds.

 

Physical And Chemical Properties Analysis
TAHP is a colorless liquid with low volatility . It has a molecular weight of 104.15 g/mol . The density is 0.9±0.1 g/cm3 . The boiling point is 144.6±9.0 °C at 760 mmHg . The vapor pressure is 2.0±0.6 mmHg at 25°C . The flash point is 41.2±18.7 °C .

 

Origin and Significance
Tert-Amyl hydroperoxide is not naturally occurring and is synthesized for industrial applications. It is primarily used as a free radical initiator for the polymerization of various monomers, particularly (meth)acrylates and styrene, leading to the production of various plastics and polymers.

 

Molecular Structure Analysis
The molecular structure of tert-amyl hydroperoxide features a branched five-carbon chain with a tertiary alcohol group (–C(OH)(CH3)2) bonded to one of the carbons. Attached to the oxygen atom of the alcohol group is a peroxide (–O-O–) moiety, which is the key functional group responsible for its initiating properties []. This peroxide bond is weak and prone to homolytic cleavage, generating free radicals that can initiate polymerization reactions.

 

Mechanism of Action
Methacryloyl Chloride | CAS 920-46-7
Acryloyl Chloride | CAS 814-68-6
Oxalyl Chloride | CAS 79-37-8
Methacryloyl Chloride | CAS 920-46-7

Target of Action
Tert-Amyl hydroperoxide (TAHP) is primarily used as a polymerization initiator . Its primary targets are unsaturated compounds such as (meth)acrylates and styrene . The t-amyl radical, which is generated from TAHP, is very efficient, leading to improved monomer conversion .

 

Mode of Action
TAHP acts as an organic peroxide , which can easily form radicals by decaying of the O-O bond, induced by heat or by UV-radiation . This qualifies TAHP for a controllable trigger of the reaction and thus as an initiator for the free-radical polymerization . The t-amyl radical generated from TAHP interacts with its targets (unsaturated compounds) to initiate the polymerization process .

 

Biochemical Pathways
The primary biochemical pathway affected by TAHP is the free-radical polymerization of unsaturated compounds . The t-amyl radical generated from TAHP initiates the polymerization process, leading to the formation of polymers .

 

Result of Action
The primary result of TAHP's action is the polymerization of unsaturated compounds . This leads to the formation of polymers, which have a wide range of applications in various industries . The t-amyl radical generated from TAHP is very efficient, leading to improved monomer conversion and narrower polydispersity .

 

Action Environment
The action of TAHP can be influenced by environmental factors such as temperature and UV radiation . TAHP is sensitive to heat and can decompose to form radicals, which can initiate the polymerization process . Therefore, the reaction conditions (e.g., temperature, UV radiation) need to be carefully controlled to ensure the efficient and safe use of TAHP .

 

Safely Handling and Storage
 

Handling

Safe handling advice: Keep away from heat. Keep away from sparks, flames and other sources of ignition. Avoid contact with eyes, skin and clothing. Avoid breathing vapor or mist. Use with adequate ventilation. The need for grounding and bonding of containers in accordance with OSHA 29 CFR 1910.106 and NFPA 77 should be assessed for all product transfers. Follow all MSDS/label precautions even after the container is emptied because it may retain product residues. Wash thoroughly after handling. Do not swallow product. Use personal protective equipment. Protect from contamination. Dispense and transfer in an area separate from storage area. Never return unused material to storage receptacle. Wash contact areas after handling. Remove contaminated clothing and wash before reuse. The addition of accelerators may result in vigorous decomposition.

Advice on protection against fire and explosion: Containers exposed to temperatures exceeding the SADT may decompose violently.

Storage

Requirements for storage areas and containers: Heat or contamination may cause hazardous decomposition. Keep containers dry and tightly closed to avoid moisture absorption and contamination. Keep container away from flammable and explosive substances. Protect from heat and exposure to direct sunlight. Store in original container.

Transport and store container in upright position only. Residual vapors might explode on ignition; do not apply heat, cut, drill, grind or weld on or near this container. Further information: Store below 104°F (40°C). Peroxide residues must not be returned into the original container, danger of decomposition!

Advice on common storage

Do not store together with: Acids, alkalis, reducing agents, metallic salts.

Storage stability: < 40°C

 

Applications of Tert-Amyl Hydroperoxide

Tert-Amyl hydroperoxide is used in the estimation of thermal decomposition temperatures of organic peroxides, which is crucial for evaluating fire hazards. A quantitative structure-property relationship (QSPR) model utilizes molecular descriptors to predict these temperatures accurately . 

 

Polymerization Initiator for Coatings Resins
As a polymerization initiator, tert-Amyl hydroperoxide is highly effective in the synthesis of water-borne acrylics. It's used in the production of coatings resins due to its high active oxygen content and water solubility, which leads to improved monomer conversion and narrower polydispersity .

 

Oxidative Desulfurization
In the field of petrochemicals, tert-Amyl hydroperoxide serves as an oxidant for desulfurization processes. It's particularly used for the removal of dibenzothiophene from model oils, contributing to cleaner fuel production .

 

Production of Low-Density Polyethylene (LDPE)
The compound is utilized in the production of LDPE. Its radical formation capability makes it a suitable initiator for the controlled polymerization process required to produce this type of polyethylene .

 

Synthesis of Polyvinylchloride (PVC)
Tert-Amyl hydroperoxide: is also involved in the synthesis of PVC. The initiation process for the polymerization of the vinyl chloride monomer can be triggered by the radicals formed from this compound .

 

Manufacturing of Styrenics
The manufacturing of styrenic polymers, such as polystyrene (PS) and expandable polystyrene (EPS), uses tert-Amyl hydroperoxide as an initiator. This application leverages its ability to induce free-radical polymerization .

 

Acrylics Polymerization
For the polymerization of acrylic monomers, tert-Amyl hydroperoxide is a key initiator. It's used in the production of polymethyl methacrylate (PMMA) and other acrylic polymers, which are essential in various industrial applications .

 

Solution Copolymerization Initiator
Lastly, tert-Amyl hydroperoxide is used as an initiator for the solution copolymerization of styrene, acrylates, and methacrylates. This process is vital for creating a wide range of copolymers with diverse properties .

 

Inducing Oxidative Stress
Tert-Amyl hydroperoxide, like other organic peroxides, readily decomposes to form free radicals, particularly hydroxyl radicals (OH•). These highly reactive molecules can damage cellular components like proteins, lipids, and DNA, leading to a state of oxidative stress. Researchers utilize tert-amyl hydroperoxide to model oxidative stress conditions in various in vitro and in vivo models to study the cellular response to such stress and the potential protective mechanisms employed by the cells [].

 

Studying Antioxidant Defense Systems
Due to its ability to induce oxidative stress, tert-amyl hydroperoxide is used to investigate the activity and regulation of antioxidant defense systems in cells and organisms. By exposing cells or tissues to controlled doses of tert-amyl hydroperoxide, researchers can measure the activity of antioxidant enzymes like superoxide dismutase, catalase, and glutathione peroxidase, as well as assess the levels of non-enzymatic antioxidants like glutathione. This helps understand how cells and organisms cope with oxidative stress and potentially identify potential therapeutic targets for diseases associated with oxidative damage.

 

 
Products Description

 

Q: What is the primary application of tert-amyl hydroperoxide in the context of the provided research?

A: The research primarily focuses on tert-amyl hydroperoxide (TAHP) as an oxidant in the oxidative desulfurization (ODS) of fuels. It acts as an alternative to hydrogen peroxide in these reactions.

Q: How does TAHP compare to other oxidants in terms of its oxidative desulfurization activity?

A: Studies comparing TAHP to other alkyl hydroperoxides, like tert-butyl hydroperoxide (TBHP) and cyclohexanone peroxide (CYHPO), in the ODS of dibenzothiophene found the reactivity order to be CYHPO > TAHP > TBHP. This order is the reverse of their peroxy oxygen electronic density, suggesting that factors beyond electron density influence the reaction.

Q: What types of catalysts are employed in conjunction with TAHP for oxidative desulfurization?

A: Various catalysts have been explored for TAHP-mediated ODS, including molybdenum oxide supported on macroporous polyacrylic cationic exchange resin D113, as well as organic acid catalysts, heteropoly acid catalysts, ampiprotic catalysts, and molecular sieve catalysts.

Q: Beyond fuel desulfurization, what other reactions utilize TAHP?

A: TAHP is utilized in the epoxidation of olefins, such as butadiene. This reaction is typically catalyzed by molybdenum compounds like molybdenyl propylene glycolate. It's also used in the epoxidation of 3-methylbut-1-ene to its corresponding oxide and diol.

Q: How does the presence of an alcohol influence TAHP-mediated epoxidation reactions?

A: Alcohols exhibit a complex influence on TAHP epoxidation. While they can inhibit the epoxidation rate, they can also increase the proportion of the active catalyst in solution. This highlights the importance of considering catalyst state changes when modeling these processes.

Q: Can TAHP oxidize metal complexes?

A: Yes, research shows that TAHP can oxidize nickel(II) complexes, specifically NiL2+ (L = 1,4,8,11-tetraazacyclotetradecane), to their NiL3+ counterparts in acidic aqueous solutions.The reaction yield is influenced by factors like reactant concentrations and the presence of oxygen.

Q: Does the structure of the alkyl hydroperoxide affect its reactivity with metal complexes?

A: Yes, studies comparing TAHP with tert-butyl hydroperoxide (TBHP) in reactions with nickel(II) complexes and vanadium(IV) show distinct reactivity patterns. For example, bromide ions alter the stoichiometry and products of the TBHP reaction but not the TAHP reaction. These differences are attributed to the relative reactivities of the intermediate alkoxyl radicals generated from each hydroperoxide.

Q: Are there specific structural features in organic peroxides that influence their reactivity?

A: Yes, research indicates that the ease of oxygen-oxygen heterolysis in peroxides is influenced by the polarization of the O-O bond and the migratory aptitudes of α-substituents. Alkyl-oxygen heterolysis, on the other hand, is promoted by electron-releasing groups on the peroxide molecule.

Q: How is TAHP synthesized?

A: One method for TAHP production involves the liquid-phase oxidation of isopentane. Mathematical models have been developed to optimize this process and determine optimal conditions for TAHP synthesis.

Q: How is TAHP used in the synthesis of other compounds?

A: TAHP reacts with azoacids in the presence of carbonyldiimidazole (CDI) to produce asymmetrical azo-perester derivatives. These reactions highlight the versatility of TAHP as a reagent in organic synthesis.

Q: Are there any studies on the stability and formulation of TAHP?

A: While the provided abstracts don't delve into specific stability or formulation details for TAHP, they emphasize its use as a reagent in various chemical reactions. This suggests that maintaining its stability, likely at lower temperatures, is crucial for its successful application.

Q: Are there any known analytical techniques for quantifying or characterizing TAHP?

A: While specific analytical techniques aren't detailed in the abstracts, they highlight the importance of monitoring reaction progress and characterizing products. Common techniques for analyzing peroxides like TAHP could include titration, gas chromatography, and various spectroscopic methods.

Q: What are the environmental concerns regarding TAHP?

A: Although not directly addressed in the provided research, being an organic peroxide, TAHP likely requires careful handling and disposal due to its potential environmental impact. Further research might focus on mitigating any negative ecological effects associated with TAHP use.

Q: Are there any alternative compounds or strategies being explored to potentially replace TAHP in its applications?

A: The research highlights the exploration of other oxidants, like TBHP and CYHPO, as potential alternatives to TAHP in ODS reacti

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