DTBP (CAS 110-05-4): Properties & Synthesis Uses

Introduction to Di-tert-butyl peroxide (CAS 110-05-4)

Di-tert-butyl peroxide, often abbreviated as DTBP, is an organic chemical compound with the CAS number 110-05-4. It belongs to the organic peroxide family, characterized by an oxygen-oxygen single bond (-O-O-). Unlike compounds used directly as medicines, DTBP’s significance lies in its role as a crucial component in various industrial chemical processes.

It is primarily known as a radical initiator. This means that under certain conditions, particularly heat, it breaks down to form highly reactive molecules called free radicals. These radicals can then kick-start or participate in important chemical reactions, especially in the manufacturing of plastics and other materials. Understanding DTBP (CAS 110-05-4) is important for appreciating the chemistry behind many everyday products and industrial processes, including potentially those involved in the synthesis of intermediates for pharmaceuticals.

Chemical Properties of Di-tert-butyl peroxide

DTBP is a clear, colorless liquid at room temperature. Its chemical formula is C8​H18​O2​. Here are some key properties:

• Stability: Compared to some other organic peroxides, DTBP is relatively stable, largely due to the bulky tert-butyl groups attached to the peroxide linkage. However, it is still thermally sensitive. It undergoes decomposition (breaks down) at temperatures above 100∘C (212∘F), releasing free radicals.
• Solubility: It is generally insoluble in water but dissolves well in many common organic solvents like alcohols and hydrocarbons.
• Volatility: It is a highly volatile liquid.
• Reactivity: The defining feature is its ability to undergo homolysis (symmetrical breaking of the O-O bond) upon heating, generating two tert-butoxy radicals ((CH3​)3​CO⋅). These radicals can further break down, producing other reactive species like methyl radicals (CH3​⋅). This reactivity is harnessed in industrial applications but also contributes to its hazards.

Uses & Applications of DTBP (CAS 110-05-4)

The primary function of Di-tert-butyl peroxide stems from its ability to generate free radicals upon decomposition. Its main applications include:

• Polymerization Initiator: This is perhaps its most significant use. DTBP initiates the polymerization of various monomers (small molecules) to form polymers (long chains). Examples include:
  • Production of Low-Density Polyethylene (LDPE).
  • Polymerization of styrene, vinyl chloride, acrylates, and methacrylates to produce plastics and resins.
• Cross-Linking Agent: It is used to cross-link polymers like polyethylene and elastomers (synthetic rubbers). Cross-linking strengthens the material, improving properties like heat resistance and durability.
• Organic Synthesis Reagent: DTBP serves as a source of radicals in various organic chemical reactions. It can be used in:
  • Modifying polypropylene (viscosity breaking).
  • Certain oxidation reactions.
  • Reactions involving C-H bond activation, methylation, or alkylation, sometimes in combination with metal catalysts.
• Chemical Intermediate Synthesis: While not a drug itself, DTBP may be used as a reagent in specific steps during the multi-stage synthesis of fine chemicals or potentially pharmaceutical intermediates. Its role here is strictly as a chemical tool in the manufacturing process, not as a therapeutic agent.

Role in Chemical Synthesis

As a radical initiator, Di-tert-butyl peroxide (CAS 110-05-4) plays a vital role in enabling specific chemical transformations that might be difficult to achieve otherwise. The tert-butoxy and methyl radicals generated during its decomposition can initiate reaction chains or directly participate in bond-forming or bond-breaking steps.

In the context of complex molecule synthesis, such as for fine chemicals or potentially intermediates leading to active pharmaceutical ingredients (APIs), DTBP might be employed in specific reaction steps like functionalizing C-H bonds or initiating cyclizations. Its usefulness lies in its relatively predictable decomposition rate at specific temperatures, allowing chemists to control the initiation of radical processes. However, its use requires careful optimization and control due to the inherent reactivity and potential side reactions associated with free radicals.

Safety Profile: Hazards & Precautions for Di-tert-butyl peroxide

Handling Di-tert-butyl peroxide (CAS 110-05-4) requires strict adherence to safety protocols due to its significant hazards. It is not intended for consumer use and should only be handled by trained professionals in controlled industrial or laboratory settings.

Key Hazards:

• Flammability: DTBP is a highly flammable liquid and vapor (Flammable Liquid Category 2). It can be ignited by heat, sparks, or flames.
• Explosion Risk: As an organic peroxide (classified as Type E), it may explode or cause a fire if heated. It is sensitive to heat and contamination, which can trigger self-accelerating decomposition, potentially leading to explosion, especially in confinement. The NFPA 704 hazard rating indicates high instability (rating of 4).
• Oxidizing Properties: It is a strong oxidizing agent and can intensify fires involving combustible materials. Keep away from wood, paper, oil, etc.
• Health Hazards:
  • Contact or ingestion may cause severe injury or burns.
  • Inhalation of vapors or decomposition products (like irritating gases produced in a fire) can cause respiratory issues.
  • It is suspected of causing genetic defects (Germ cell mutagenicity Category 2). Always minimize exposure.
  • Some sources rate the health hazard as 3 (out of 4) on the NFPA diamond, indicating it can cause serious or permanent injury, likely related to its reactivity and decomposition hazards.

Safety Precautions:

• Handling: Use only in well-ventilated areas, away from heat, sparks, open flames, and incompatible materials (like reducing agents, acids, bases, metals). Use appropriate personal protective equipment (PPE), including gloves, safety goggles, and flame-resistant clothing. Ground containers during transfer.
• Storage: Store in a cool, well-ventilated place, away from heat sources and direct sunlight. Keep containers tightly closed. Store separately from combustible and incompatible materials. Follow specific storage temperature guidelines (often requires refrigeration or freezing).
• Spills: Eliminate ignition sources immediately. Keep combustibles away. Do NOT touch spilled material without appropriate PPE. Small spills may be absorbed with inert material, but large spills require specialized response. Keep spilled material wet with water spray if safe to do so.
• Fire: Use water spray or fog from a distance for large fires. Do not use straight streams. Cool containers exposed to fire. Fight fire remotely due to explosion risk.

Always consult the specific Safety Data Sheet (SDS) for Di-tert-butyl peroxide (CAS 110-05-4) before handling.

Manufacturing Process Overview

The industrial synthesis of Di-tert-butyl peroxide typically involves the reaction of tert-butyl hydroperoxide ($ (CH_{3}){3}COOH $)with\ast \ast isobutylene\ast \ast ($ (CH{3}){2}C=CH{2} $)inthepresenceofanacidcatalyst,oftensulfuricacid.Anotherrouteinvolvesthereactionoftert-butylalcohol($ (CH_{3})_{3}COH $) with hydrogen peroxide under specific conditions, often catalyzed. The process requires careful control of temperature and reactant concentrations to ensure safety and maximize yield, given the hazardous nature of peroxides. Purification steps are necessary to obtain DTBP of desired purity (e.g., >98% or >99% for specific applications).

FAQ Section

1. What is Di-tert-butyl peroxide primarily used for?

Di-tert-butyl peroxide (CAS 110-05-4) is mainly used as a radical initiator in the industrial production of polymers like LDPE, polystyrene, and acrylic resins. It’s also used for cross-linking polymers and as a reagent in organic synthesis.

2. Is Di-tert-butyl peroxide safe to handle?

No, Di-tert-butyl peroxide is hazardous. It is highly flammable, can cause fire or explosion upon heating, is a strong oxidizer, may cause severe burns, and is suspected of causing genetic defects. It requires strict safety protocols and should only be handled by trained personnel in appropriate facilities.

3. How stable is Di-tert-butyl peroxide (CAS 110-05-4)?

It is one of the more stable organic peroxides at room temperature but is sensitive to heat. Decomposition starts significantly above 100∘C (212∘F), releasing reactive free radicals. Contamination can lower its decomposition temperature, increasing risk.

4. Does Di-tert-butyl peroxide have any direct medical uses?

No, Di-tert-butyl peroxide is not used directly as a medicine or therapeutic agent due to its hazardous nature. Its connection to the pharmaceutical industry is indirect, potentially being used as a reagent in the chemical synthesis process to create intermediates needed for drug manufacturing.

5. How should DTBP be stored?

DTBP must be stored in a cool, well-ventilated area, away from heat, sunlight, and incompatible materials. Specific temperature-controlled storage (often refrigerated or frozen) is usually required, as detailed in the Safety Data Sheet (SDS).