87-68-3

Usage

Uses

Used in Chemical Production:
Perchlorobutadiene is used as an intermediate in the production of various chemicals, including pesticides, rubber antioxidants, and pharmaceuticals. Its versatility as a chemical intermediate makes it valuable in the synthesis of a wide range of products.
Used in Pesticide Industry:
In the pesticide industry, Perchlorobutadiene is used as a key component in the synthesis of certain pesticides. Its chemical properties allow for the creation of effective pest control agents.
Used in Rubber Industry:
Perchlorobutadiene is utilized as a rubber antioxidant, helping to improve the durability and performance of rubber products by preventing degradation caused by exposure to heat, light, and oxygen.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, Perchlorobutadiene serves as an intermediate in the synthesis of specific pharmaceutical compounds, contributing to the development of new medications.
However, due to its potential for harm, the use and production of Perchlorobutadiene are heavily regulated in many countries. Ongoing efforts are made to minimize exposure and evaluate its health and environmental impacts, ensuring that its applications are balanced with the need to protect human health and the environment.

InChI:InChI=1/C4Cl6/c5-1(3(7)8)2(6)4(9)10

Upstream product

• 106-98-9 1-butylene 
• 127-18-4 1,1,2,2-tetrachloroethylene 
• 111-71-7 heptanal 
• 20338-26-5 1,1,2,2,3,3,4,4-octachlorobutane 
• 32694-76-1 1,1,1,2,3,3,4,4-octachlorobutane 
• 1888-73-9 1,1,2,3,4,5,5,5-octachloro-penta-1,3-diene 
• 590-19-2 2,3-dimethylbutene 
• 6820-74-2 decachlorobutane 
• 920-80-9 1,1,1,2,3,4-hexachloro-but-2-ene 
• 638-45-9 1-Iodohexane 
• 10075-38-4 1,3-Dichloro-2-butene 
• 74-86-2 acetylene 
• 106-97-8 n-butane 
• 56-23-5 tetrachloromethane 

Downstream Products

• 6012-97-1 2,3,4,5-tetrachlorothiophene 
• 303-04-8 2,3-dichloro-1,1,1,4,4,4-hexafluoro-2-butene 
• 1441-56-1 butadiene-d6 
• 67-72-1 hexachloroethane 
• 335-44-4 heptafluoro-2,3,3-trichlorobutane 
• 375-43-9 1,2,3,4-tetrafluoro-1,1,2,3,4,4-hexachlorobutane 
• 6820-74-2 decachlorobutane 
• 14621-81-9 Pentachlorbutadienyl-phenyl-sulfid 
• 13178-31-9 2,3,4,4-Tetrachlor-3-butensaeure-morpholid 
• 20932-80-3 1,1,1,4,4,4-hexakis(trimethylsilyl)butin-2 
• 77301-72-5 1,1,2,3,4-Pentachlor-4-(cyclohexylthio)-1,3-butadien 
• 77301-73-6 1,2,3,4-Tetrachlor-1,4-bis(cyclohexylthio)-1,3-butadien 
• 77958-42-0 2,6-dimethyl-6-(trichlorobut-3-en-1-ynyl)-2-cyclohexen-1-one 
• 72475-34-4 1,1,2,4,4-pentakis-(4-chloro-phenylsulfanyl)-buta-1,3-diene 

Relevant academic research and scientific papers

Synthesis of Decorated Carbon Structures with Encapsulated Components by Low-Voltage Electric Discharge Treatment

Abstract: Polycondensation of complexes of chloromethanes with triphenylphosphine by the action of low-voltage electric discharges in the liquid phase gives nanosized solid products. The elemental composition involving the generation of element distribution maps (scanning electron microscopy–energy dispersive X?ray spectroscopy mapping) and the component composition (by direct evolved gas analysis–mass spectrometry) of the solid products have been studied. The elemental and component compositions of the result-ing structures vary widely depending on the chlorine content in the substrate and on the amount of triphenylphosphine taken. Thermal desorption analysis revealed abnormal behavior of HCl and benzene present in the solid products. In thermal desorption spectra, these components appear at an uncharacteristically high temperature. The observed anomaly in the behavior of HCl is due to HCl binding into a complex of the solid anion HCI-2 with triphenyl(chloromethyl)phosphonium chloride, which requires a relatively high temperature (up to 800 K) to decompose. The abnormal behavior of benzene is associated with its encapsulated state in nanostructures. The appearance of benzene begins at 650 K and continues up to temperatures above 1300?K.

Preparation method of hexachloro-1,3-butadiene

The invention provides a preparation method of hexachloro-1,3-butadiene. The preparation method has the characteristics as follows: trichlorethylene and tetrachlorethylene are used as raw materials, anhydrous metal chloride is used as a catalyst, the metal chloride can be one or more of ferric chloride, aluminum chloride and zinc chloride, a reactant is one or two of trichlorethylene and tetrachlorethylene, the molar ratio of the trichloroethylene to the tetrachlorethylene is 0:100 to 100:0, and the mass fraction of the catalyst is 1-20%. Under the condition that the reaction temperature is 50-250 DEGC, the conversion rate of the reactant is 20-80%, and the selectivity of the hexachloro-1,3-butadiene is 20-60%. The preparation method is simple in process, simple and convenient in operation, low in energy consumption and high in atom utilization rate.

Addition of tetrachloromethane to oct-1-ene initiated by amino alcohols

The kinetics and mechanism of an addition of CCl4 to oct-1-ene initiated by amines, aromatic alcohols, and amino alcohols (structural analogs of ephedrin) were studied. The radical mechanism of the reaction was established by ESR using the technique of spin traps. Aromatic amino alcohols as initiators are more active than amines and aromatic alcohols of similar structure. They are more selective compared to the amines and aromatic alcohols and react with CCl4 already at room temperature to form predominantly benzaldehyde. The scheme of initiation by aromatic amino alcohols of the addition of CCl 4 to olefins was proposed on the basis of the experimental data.

Specificity and non-specificity in the sensitized CO2-laser-induced reaction of tetrachloroethene

Previous workers have investigated the reaction of tetrachloroethene using thermal initiation and CO2-laser initiation via sensitizing species. In both instances, the principal product was found to be hexachlorobenzene. One group reported evidence of laser specificity in this reaction, in that BCl3 acted as a sensitizer to produce hexachlorobenzene as the principal product, but SF6 and BBr3 did not. We have found that specificity is highly dependent on reaction conditions. We reproduced the previous results using similar experimental conditions, but under different conditions, we found that the specificity is lost, with all three sensitizers which we used (BCl3, SF6, and SiF4) sensitizing the reaction to produce mainly hexachlorobenzene. There were some differences among the sensitizers, as, for example, the fact that SF6 produced the most nearly pure hexachlorobenzene product.

Organochlorine formation in magnesium electrowinning cells

The formation of organochlorines during the electrolytic production of magnesium was investigated using a laboratory-scale electrolytic cell having a graphite anode, a liquid aluminium alloy cathode, and a molten chloride electrolyte. The cell was operated at current densities ranging from 3000 to 10,000 A m-2 and at temperatures ranging from 660°C to 750°C. Organochlorines were adsorbed from the cell off-gases onto silica gel, extracted with hexane, and determined by gas chromatography. All compounds identified were fully chlorinated aliphatic and aromatic compounds, the major components being hexachlorobutadiene, hexachlorobenzene, hexachloroethylene, and octachlorostyrene. The total amount of organochlorines per tonne of magnesium produced decreased with electrolysis time and with current density and increased with operating temperature; it was also dependent on the type of graphite employed. The output of organochlorines Varied from 5 to 20 g t-1 of magnesium.

Copper-catalyzed chlorination and condensation of acetylene and dichloroacetylene

The chlorination and condensation of acetylene at low temperatures is demonstrated using copper chlorides as chlorinated agents coated to model borosilicate surfaces. Experiments with and without both a chlorine source and borosilicate surfaces indicate the absence of gas-phase and gas-surface reactions. Chlorination and condensation occur only in the presence of the copper catalyst. C2 through C8 organic products were observed in the effluent; PCDD/F were only observed from extraction of the borosilicate surfaces. A global reaction model is proposed that is consistent with the observed product distributions. Similar experiments with dichloroacetylene indicate greater reactivity in the absence of the copper catalyst. Reaction is observed in the gas-phase and in the presence of borosilicate surfaces at low temperatures. The formation of hexachlorobenzene is only observed in the presence of a copper catalyst. PCDD/F were only observed from extraction of the borosilicate surfaces. A global reaction model is proposed for the formation of hexachlorobenzene from dichloroacetylene. (C) 2000 Elsevier Science Ltd.

Role of copper species in chlorination and condensation reactions of acetylene

We examined the thermally induced acetylene chlorination and condensation reactions on different types of copper salt impregnated surfaces. The System for Thermal Diagnostic Studies provided a powerful tool to study these reactions under defined reaction conditions, which were related to typical conditions in postcombustion incineration processes. Experiments were conducted with acetylene or acetylene/HCl mixtures in a quarts reactor filled with a borosilicate foam of known pore size at temperatures between 150 and 500 °C. Borosilicate was also used as the catalytic support for gas-solid reactions of acetylene and acetylene/HCl mixtures with CuCl2 and CuO. Reaction products were trapped in-line and analyzed by GC/MS. It was shown that borosilicate is not able to catalyze acetylene condensation reactions. CuCl2-impregnated borosilicate was a highly effective catalyst for acetylene chlorination/condensation reactions at temperatures above 150 °C. The same behavior was found for CuO- impregnated borosilicate in the presence of HCl. However, temperatures above 300 °C were required for this catalytic system. Mainly perchlorinated C-2 to C-8 hydrocarbons were trapped as reaction products in the gas phase. Maximum yields for acetylene chlorination/condensation reactions in each related catalytic system were found at temperatures between 300 and 400 °C. Results of the surface-catalyzed acetylene chlorination and condensation reactions were summarized in a global mechanism. A ligand transfer oxidative chlorination of acetylene with CuCl2 was proposed to be the initiation of acetylene with CuCl2 was proposed to be the initiating step. Chlorinated acetylene then condenses to higher molecular weight compounds, catalyzed by CuCl in metallacyclization reactions. We examined the thermally induced acetylene chlorination and condensation reactions on different types of copper salt impregnated surfaces. The System for Thermal Diagnostic Studies provided a powerful tool to study these reactions under defined reaction conditions, which were related to typical conditions in postcombustion incineration processes. Experiments were conducted with acetylene or acetylene/HCl mixtures in a quartz reactor filled with a borosilicate foam of known pore size at temperatures between 150 and 500 °C. Borosilicate was also used as the catalytic support for gas-solid reactions of acetylene and acetylene/HCl mixtures with CuCl2 and CuO. Reaction products were trapped in-line and analyzed by GC/MS. It was shown that borosilicate is not able to catalyze acetylene condensation reactions. CuCl2-impregnated borosilicate was a highly effective catalyst for acetylene chlorination/condensation reactions at temperatures above 150 °C. The same behavior was found for CuO-impregnated borosilicate in the presence of HCl. However, temperatures above 300 °C were required for this catalytic system. Mainly perchlorinated C-2 to C-8 hydrocarbons were trapped as reaction products in the gas phase. Maximum yields for acetylene chlorination/condensation reactions in each related catalytic system were found at temperatures between 300 and 400 °C. Results of the surface-catalyzed acetylene chlorination and condensation reactions were summarized in a global mechanism. A ligand transfer oxidative chlorination of acetylene with CuCl2 was proposed to be the initiating step. Chlorinated acetylene then condenses to higher molecular weight compounds, catalyzed by CuCl in metallacyclization reactions.

Reaction of 1-bromo-1,2,4,4-tetrachloro-1,3-butadiene with chlorosulfonic acid

1-Bromo-1,2,4,4-tetrachloro-1,3-butadiene reacts with chlorosulfonic acid to give 1,3-dibromo1,2,4,4-tetrachloro-1,3-butadiene, bromochloromaleic acid, and hexachlorobutadiene. 1,3-Dibromo-1,2,4,4-tetrachloro-1,3-butadiene was also obtained by bromination of 1-bromo-1,2,4,4-tetrachloro-l,3-butadiene and subsequent dehydrobromination; 1,2,4-tribromo-1,3,4-trichloro-1,3-butadiene was also formed as by-product.

NOVEL PRODUCTS IN THE CO2-LASER INDUCED REACTION OF TRICHLOROETHYLENE

Previous report on the thermal or CO2-laser induced decomposition of trichloroethylene have identified only one condensable product, hexachlorobenzene (in addition to HCl and mono- and dichloroacetylene).We have found that trichloroethylene vapor exposed to cw irradiation on the P(24) line of the (001-100) band of the CO2 laser at incident power levels from 8-17 W procedures numerous products, of which the 13 major ones have been identified using IR, GC/MS, GC/FTIR, and NMR methods.All of these products have 4, 6, or 8 carbons, are highly unsaturated, and are completely chlorinated or contain a single hydrogen.C4HCl5 and C6Cl6 isomers (three of each) account for ca. 55percent to 85percent of total products (based on peak area in the total ion chromatograms in GC/MS runs), depending on reaction conditions.In addition to characterizing the products, we discuss the dependence of the product distribution on laser power, irradiation time, and cell geometry, and we outline a possible mechanism.

Preparation of polyfluorobutenes

1,1,1,2,4,4,4-Heptafluoro-2-butene and 2-chloro-1,1,1,4,4,4,-hexafluoro-2-butene are prepared simultaneously by reacting hexachlorobutadiene with hydrogen fluoride with the addition of catalytic amounts of titanium halide, antimony trihalide and/or antoimony pentahalide.