3405-32-1

Usage

Uses

Used in Chemical Synthesis:
1,2,3,4-Tetrachlorobutane is utilized as a reagent in chemical synthesis processes for its ability to facilitate specific chemical reactions, contributing to the production of various industrial chemicals.
Used in Solvent Applications:
As a solvent, 1,2,3,4-tetrachlorobutane is employed in certain industrial applications where its solubility properties are advantageous for dissolving other substances, particularly in processes that require a non-polar or slightly polar solvent.
Used in Industrial Processes:
1,2,3,4-Tetrachlorobutane is used in specific industrial processes where its chemical properties are necessary for the manufacturing of certain products, although its use is being scrutinized and reduced due to safety and environmental concerns.

InChI:InChI=1/C4H6Cl4/c5-1-3(7)4(8)2-6/h3-4H,1-2H2

Synthetic route

1,4-dichloro-2-butene (764-41-0) → 1,2,3,4-tetrachlorobutane (3405-32-1)

Conditions	Yield
With chloroform; chlorine meso-1,2,3,4-tetrachloro-butane;
With chloroform; chlorine racem.-1,2,3,4-tetrachloro-butane;
With chlorine Product distribution / selectivity;

meso-erythritol (909878-64-4) → 1,2,3,4-tetrachlorobutane (3405-32-1)

Conditions	Yield
With phosphorus pentachloride

2,3-dimethylbutene (590-19-2) → 1,2,3,4-tetrachlorobutane (3405-32-1)

Conditions	Yield
With sulfur dichloride; Petroleum ether unter Kuehlung; racem.-1,2,3,4-tetrachloro-butane;

3,4-dichlorobut-1-ene (310447-99-5, 310448-01-2) → 1,2,3,4-tetrachlorobutane (3405-32-1)

Conditions	Yield
With chloroform; chlorine racem.-1,2,3,4-tetrachloro-butane;
With chloroform; chlorine meso-1,2,3,4-tetrachloro-butane;
With chlorine at 40℃;

1,2,3,4-tetrafluoro-1,1,2,3,4,4-hexachlorobutane (375-43-9) → 1,2,3,4-tetrachlorobutane (3405-32-1) + 1,1,2,3,4-pentafluoropentachlorobutane (355-19-1)

Conditions	Yield
With antimony dichloride trifluoride at 250℃;

buta-1,3-diene (106-99-0) → 1,2,3,4-tetrachlorobutane (3405-32-1)

Conditions	Yield
With tetrachloromethane; chlorine
With chlorine in verschiedenen Loesungsmitteln unter Kuehlung mit Eis-Kochsalz-Gemisch; meso-1,2,3,4-tetrachloro-butane;
With chlorine in verschiedenen Loesungsmitteln unter Kuehlung mit Eis-Kochsalz-Gemisch; racem.-1,2,3,4-tetrachloro-butane;

acetylene (74-86-2) → 1,2,3,4-tetrachlorobutane (3405-32-1)

Conditions	Yield
With hydrogenchloride unter der Einw. dunkler elektrischer Entladungen;

1,2-dichloro-ethane (107-06-2) → 1,2,3,4-tetrachlorobutane (3405-32-1) + chloroethylene (75-01-4) + 1,1,2-trichloroethane (79-00-5) + acetylene (74-86-2)

Conditions	Yield
at 303.9℃; under 150 Torr; Quantum yield; Product distribution; Mechanism; Irradiation; different temperatures, variation of pressure;

tetrachloromethane (56-23-5) + chlorine (7782-50-5) + buta-1,3-diene (106-99-0) → 1,2,3,4-tetrachlorobutane (3405-32-1)

antimonypentachloride (7647-18-9) + chlorine (7782-50-5) + buta-1,3-diene (106-99-0) → 1,2,3,4-tetrachlorobutane (3405-32-1)

Conditions	Yield
at 30 - 100℃;

chlorine (7782-50-5) + iron(III) chloride (7705-08-0) + buta-1,3-diene (106-99-0) → 1,2,3,4-tetrachlorobutane (3405-32-1)

Conditions	Yield
at 30 - 100℃;

chlorine (7782-50-5) + buta-1,3-diene (106-99-0) → 1,4-dichloro-2-butene (764-41-0) + 1,2,3,4-tetrachlorobutane (3405-32-1) + 3,4-dichlorobut-1-ene (310447-99-5, 310448-01-2)

Conditions	Yield
in verschiedenen Loesungsmitteln bei Kuehlung mit Kaeltemischung;
in verschiedenen Loesungsmitteln bei Kuehlung mit Kaeltemischung;

1,2,3,4-butanetetrol (2319-57-5, 2418-52-2, 6968-16-7, 7493-90-5, 7541-59-5) + phosphorus pentachloride (10026-13-8, 874483-75-7) → 1,2,3,4-tetrachlorobutane (3405-32-1)

trans-1,4-dichlorobut-2-ene (110-57-6) + chloroform (67-66-3) + chlorine (7782-50-5) → 1,2,3,4-tetrachlorobutane (3405-32-1)

buta-1,3-diene (106-99-0) → 1,4-dichloro-2-butene (764-41-0) + 1,2,3,4-tetrachlorobutane (3405-32-1) + 3,4-dichlorobut-1-ene (310447-99-5, 310448-01-2)

Conditions	Yield
With chlorine In tetrachloromethane at 50℃; Product distribution / selectivity;

1,2,3,4-tetrachlorobutane (3405-32-1) → perfluoro-1,2,3,4-tetrachlorobutane (375-45-1)

Conditions	Yield
With hydrogen fluoride In tetrachloromethane under 3750.38 - 7500.75 Torr; Product distribution / selectivity; Autoclave;	82.1%
With hydrogen fluoride; fluorine at 35 - 40℃; under 1500.15 - 7500.75 Torr; for 45h; Product distribution / selectivity; Inert atmosphere;	80%
With fluorine at 40℃; under 3750.38 Torr; Product distribution / selectivity;	74.2%

1,2,3,4-tetrachlorobutane (3405-32-1) → cis-1,2,4-trichloro-2-butene (64490-87-5)

Conditions	Yield
With potassium hydroxide In methanol; water for 1h; Heating;	3%

1,2,3,4-tetrachlorobutane (3405-32-1) → 3-chloro-2-fluorobuta-1,3-diene (381-68-0)

Conditions	Yield
With hydrogen fluoride Behandeln des Reaktionsprodukts mit wss.Alkali;

ethanol (64-17-5) + 1,2,3,4-tetrachlorobutane (3405-32-1) + zinc → buta-1,3-diene (106-99-0)

Conditions	Yield
racem.-1,2,3,4-tetrachloro-butane;
meso-1,2,3,4-tetrachloro-butane;

1,2,3,4-tetrachlorobutane (3405-32-1) → 2,3-dichlorobuta-1,3-diene (1653-19-6) + dichlorobutadiene

Conditions	Yield
at 10 - 15℃;
at 10 - 15℃;

1,2,3,4-tetrachlorobutane (3405-32-1) + methanolic KOH → 2,3-dichlorobuta-1,3-diene (1653-19-6) + isomer(ic) dichlorobutadiene

Conditions	Yield
at 10 - 18℃; racem.-1,2,3,4-tetrachloro-butane;
at 10 - 18℃; meso-1,2,3,4-tetrachloro-butane;
at 10 - 18℃; meso-1,2,3,4-tetrachloro-butane;
at 10 - 18℃; racem.-1,2,3,4-tetrachloro-butane;

1,2,3,4-tetrachlorobutane (3405-32-1) → 2,3-dichlorobuta-1,3-diene (1653-19-6)

Conditions	Yield
With sodium hydroxide In methanol for 21h; Product distribution / selectivity; Inert atmosphere;

Upstream product

• 764-41-0 1,4-dichloro-2-butene 
• 74-86-2 acetylene 
• 107-06-2 1,2-dichloro-ethane 
• 7782-50-5 chlorine 
• 106-99-0 buta-1,3-diene 
• 821-10-3 1,4-Dichloro-2-butyne 
• 67-56-1 methanol 
• 110-22-5 diacetyl peroxide 
• 110-57-6 trans-1,4-dichlorobut-2-ene 
• 67-66-3 chloroform 
• 2319-57-5 1,2,3,4-butanetetrol 
• 10026-13-8 phosphorus pentachloride 
• 7705-08-0 iron(III) chloride 
• 7647-18-9 antimonypentachloride 

Downstream Products

• 106-99-0 buta-1,3-diene 
• 1653-19-6 2,3-dichlorobuta-1,3-diene 
• 375-45-1 perfluoro-1,2,3,4-tetrachlorobutane 

Relevant academic research and scientific papers

PROCESS FOR PRODUCING 1,2,3,4-TETRACHLOROBUTANE

There is provided a method of producing 1,2,3,4-tetrachlorobutane capable of stably and economically producing 1,2,3,4-tetrachlorobutane. A reactant solution (1) containing 3,4-dichloro-1-butene is charged in a reaction vessel (11) having an inner surface, to be brought into contact with the reactant solution (1), made of a metal and a chlorine gas is introduced into the reactant solution (1) to perform a reaction between 3,4-dichloro-1-butene and the chlorine gas to produce 1,2,3,4-tetrachlorobutane. The reaction is performed while carrying out an operation of taking out at least a portion of the reactant solution (1) from the reaction vessel (11), filtering the reactant solution (1) thus taken out to remove a solid matter, and returning the filtered reactant solution (1) into the reaction vessel (11).

Production method and production system of 1,2,3,4-tetrachlorobutane

The invention relates to a production method and production system of 1,2,3,4-tetrachlorobutane. The production method comprises the following two steps: (1) introducing chlorine and gas 1,3-butadieneinto a solvent A in the presence of a catalyst, and obtaining a mixture A containing 1,2,3,4-tetrachlorobutane; and (2) mixing the mixture A obtained in step (1) and a solvent B, performing crystallization, and obtaining 1,2,3,4-tetrachlorobutane with high purity. The production method is high in reaction yield, moderate in conditions, simple in reaction, low in energy consumption, low in equipment requirement and high in yield. The production method is more suitable for industrialized production. The temperature of cold water can be adjusted at any time by virtue of a cold source preparationapparatus according to the requirement of a reactor, and the needed temperature in the reactor can be ensured.

PRODUCTION PROCESS AND PURIFICATION PROCESS FOR 1,2,3,4-TETRACHLOROHEXAFLUOROBUTANE

It is an object of the present invention to provide a process for producing 1,2,3,4-tetrachlorohexafluorobutane industrially inexpensively and efficiently by utilizing expensive fluorine gas efficiently and to provide a process which is capable of stably producing 1,2,3,4-tetrachlorohexafluorobutane and in which, by carrying out fluorination reaction at a low temperature, side reactions such as formation of a low-boiling substance due to cleavage of C—C bonds and formation of an excess fluoride are difficult to occur. The process for producing 1,2,3,4-tetrachlorohexafluorobutane of the present invention is characterized in that it includes feeding fluorine gas to 1,2,3,4-tetrachlorobutane using plural reactors in the presence of a solvent and in the absence of a catalyst to allow the 1,2,3,4-tetrachlorobutane and the fluorine gas to react with each other, wherein a part or all of unreacted fluorine gas discharged from one reactor is introduced into a reactor different from said one reactor.

PROCESS FOR PRODUCING 1,2,3,4-TETRACHLOROHEXAFLUOROBUTANE

The present invention provides a process for producing 1,2,3,4-tetrachlorohexafluorobutane having a high purity at a low cost industrially and efficiently. The process for producing 1,2,3,4-tetrachlorohexafluorobutane according to the present invention comprises a step of allowing 1,2,3,4-tetrachlorobutane to react with a fluorine gas to prepare a reaction product containing 1,2,3,4-tetrachlorohexafluorobutane and hydrogen-containing compounds as an impurity, and a step of introducing the reaction product into single or plural distillation columns and distilling to separate the hydrogen-containing compounds from the reaction product and thereby preparing purified 1,2,3,4-tetrachlorohexafluorobutane wherein the at least one of distillation columns has a theoretical plate number of 15 or more.

AN IMPROVED PROCESS FOR THE PREPARATION OF 2,3,-DICHLORO 1,3,BUTADIENE FROM 1,3 BUTADIENE

The present invention relates to an improved process for the production of 2,3-Dichloro 1,3-Butadiene which comprises Chlorinating Butadiene, in liquid phase, in the presence of chlorinated solvents and phase transfer catalyst, Distilling the solvent, Distilling the formed 3,4-dichlorobutene-1, 1,4-dichlorobutene-2; and 1,2,3,4-Tetrachlorbutane; under reduced pressure,chlorinating the separated 3,4-dichlorobutene-1 and 1,4-dichlorobutene-2 to give 1,2,3,4-Tetrachlorobutane.,double Dehydrochlorinating the 1,2,3,4-Tetrachlorobutane using methanol,alkali and inhibitors under atmosphere of 1% oxides of nitrogen in nitrogen atmosphere the total period of Dehydrochlorinating being in the range of 15-33 hours to give 2,3-Dichloro 1,3-Butadiene and separating methanol to get 2,3-Dichloro 1,3-Butadiene

PRODUCTION PROCESS FOR 1,2,3,4-TETRACHLOROHEXAFLUOROBUTANE AND REFINING PROCESS

The production process for 1,2,3,4-tetrachlorohexafluorobutane of the present invention is characterized in that 1,2,3,4-tetrachlorobutane is reacted with fluorine in the presence of a solvent containing hydrogen fluoride. The 1,2,3,4-tetrachlorobutane may be obtained by chlorination of 3,4-dichlorobutene-1. Further, the present invention provides as well a process of refining 1,2,3,4-tetrachlorohexafluorobutane obtained in the manner described above. According to the present invention, 1,2,3,4-tetrachlorohexafluorobutane which is useful, for example, as a synthetic raw material for hexafluoro-1,3-butadiene used as an etching gas for semiconductors can industrially efficiently be produced by using 1,2,3,4-tetrachlorobutane which is a by-product of chloroprene and which has so far been disposed.

PROCESS FOR PRODUCING 1,2,3,4-TETRACHLOROHEXAFLUOROBUTANE

Disclosed is a process for producing 1,2,3,4-tetrachlorohexafluorobutane safely in a high yield in the industrial viewpoint and at low cost in the economical viewpoint. Specifically disclosed is a process for producing 1,2,3,4-tetrachlorohexafluorobutane which process comprises: (1) a step of chlorinating 1,3-butadiene, thereby preparing a mixture containing 1,2,3,4-tetrachlorobutane, and (2) a step of allowing the 1,2,3,4-tetrachlorobutane prepared in the step (1) to react with a fluorine gas in the presence of a diluting gas in a gas phase, thereby preparing a mixture containing 1,2,3,4-tetrachlorohexafluorobutane.

KrF Laser-induced Thermal Decomposition of 1,2-Dichloroethane

The thermal decomposition of 1,2-dichloroethane to give vinyl chloride and hydrogen chloride has been reinvestigated at 703 K and the major features of this free-radical chain reaction found previously have been confirmed.A direct comparison of the pulsed KrF laser-induced process (248 nm) in the same static reactor at this temperature showed that a substantial increase in rate occurs even at low pulse-repetition rates (2 Hz).In an extended study of the laser-induced reaction at temperature where thermal reaction is negligible (476-577 K), quantum yields of vinyl chloride formation have been measured to be between 3000 and 13 000.Quantum yields decreased slighthly with increasing pressure and showed an inverse square-root dependence on initial chlorine atom concentration.The major by-products were identified as ethene, ethyne, 1,2,3,4-tetrachlorobutane and 1,1,2-trichloroethane.At 577 K and 150 Torr, the quantum yield of ethene production is close to unity, indicating that under these conditions reaction (2) is essentially complete. C2H4Cl2 + hν (248 nm) --> CH2ClCH2* + Cl (1) CH2ClCH2* --> C2H4 + Cl (2) Computer modelling of a complete reaction mechanism involving the propagation steps (3) and (4) Cl + C2H4Cl2 --> C2H3Cl2 + HCl (3) C2H3Cl2 --> C2H3Cl + Cl (4) was used to predict quantum yields of both vinyl chloride and the minor products.

Three-Component Reactions. IX. Methoxychlorination of Butadiene. 1. Composition of Reaction Mixtures Obtained Using Either an Excess of Butadiene or an Excess of Chlorine

Methoxychlorination of butadiene with 2 mol chlorine gives saturated secondary addition products 5-15, which were found identical with methoxychlorination products of unsaturated primary addition products 1-4 (investigated by capillar GLC). 1,2 and 3 add chlorine and methanol with high regioselectivity (80-90percent); meso and erythro isomer predominate in MARKOVNIKOV products from 1 and 2 (87percent diastereoselectivity). 5-7 and 11-15 were separated by preparative GLC for structural analysis.