616-21-7

Usage

Uses

Used in Chemical Synthesis:
1,2-Dichlorobutane is used as a reactant in the alkylation of benzene, which is a crucial process in the production of various chemicals and materials. The alkylation is facilitated by using catalysts such as aluminium chloride or liquid hydrogen fluoride, leading to the formation of valuable compounds for further industrial use.
Used in Temperature-Composition Phase Diagrams:
1,2-Dichlorobutane is utilized in the evaluation of temperature-composition phase diagrams of binary mixtures. These mixtures consist of a haloalkane dissolved in either 1-ethyl-3-methylimidazolium ethylsulfate or 1-ethyl-3-methylimidazolium ethylsulfonate. The study of these phase diagrams is essential for understanding the behavior of these mixtures under different conditions, which can be beneficial for optimizing processes in various industries.

InChI:InChI=1/C4H8Cl2/c1-2-4(6)3-5/h4H,2-3H2,1H3

Upstream product

• 106-98-9 1-butylene 
• 78-86-4 s-butyl chloride 
• 109-69-3 n-Butyl chloride 
• 78-00-2 tetraethyllead(IV) 
• 1071-08-5 1,1,1,3,4-pentachlorobutane 
• 75-21-8 oxirane 
• 5197-62-6 2-[2-(chloroethoxy)ethoxy]ethanol 
• 628-89-7 2-(2-Chloroethoxy)ethanol 
• 107-07-3 2-chloro-ethanol 
• 7732-18-5 water 
• 7782-50-5 chlorine 
• 60-29-7 diethyl ether 
• 13898-47-0 hypochloric acid 
• 7791-25-5 sulfuryl dichloride 

Downstream Products

• 107-00-6 but-1-yne 
• 1190-22-3 1,3-dichlorobutane 
• 16128-68-0 butane-1,2-dithiol 
• 18338-40-4 1,2,3-trichloro-butane 
• 106-99-0 buta-1,3-diene 
• 110-16-7 maleic acid 
• 584-03-2 1,2-dihydroxybutane 
• 41135-45-9 1,2,2-Trichlor-butan 
• 66675-32-9 1,1,2-trichloro-butane 
• 1790-22-3 1,2,4-trichlorobutane 
• 10489-28-8 2,2-dimethyl-indan-1-one 
• 719-79-9 1,1-diphenylbutane 
• 1520-44-1 1,3-diphenylbutane 
• 5223-61-0 2,2-diphenyl-butane 

Relevant academic research and scientific papers

Process for the preparation of monocarboxylic anhydrides

The process for the preparation of monocarboxylic anhydrides of the general formula (RCO) 2 O is carried out by reacting a carboxylic ester or a dialkyl ether of the general formula RCOOR or ROR, in which R in each case denotes the same alkyl radical having 1 to 4 carbon atoms, with carbon monoxide in the gas phase in the presence of a supported catalyst. The reaction takes place by means of bromine or iodine or compounds thereof as reaction promoter. The support material in the catalyst supports a noble metal chelate compound which is formed by a noble metal compound from group VIII of the periodic table and a chelating agent containing organonitrogen, organophosphorus, organoarsenic, organosulfur or mercapto groups and substituted in its basic structure with alkyl, aryl or aralkyl groups. The reaction is carried out at temperatures from 130° to 400° C. and pressures from 1 to 150 bar.

Versatility of Zeolites as Catalysts for Ring or Side-Chain Aromatic Chlorinations by Sulfuryl Chloride

Zeolites catalyze chlorination of aromatics by sulfuryl chloride SO2Cl2.It is possible by an appropriate choice of the catalyst to effect at will, with very high selectivity, either the ring or the side-chain chlorination.Zeolite ZF520 is the choice catalyst for the former, because of its high Broensted acidity.Zeolite NaX (13X) is a fine catalyst for the latter, free-radical chlorination; the reaction is best effected in the presence of a light source; the catalyst can be reused many times with no loss in activity.Both reaction modes, the ionic (ring chlorination)and the radical (side-chain substitution), are likely to occur outside of the channel network in the microporous solid.The effects of various experimental factors - such as the nature of the solvent, the reaction time and temperature, the Broensted acidity of the solid support, the presence of radical inhibitors, and the quantity of catalysts - were investigated.The procedures resulting from this study are very easy to implement in practice and are quite effective.

MECHANISMS OF FREE-RADICAL REACTIONS. XXIV. QUANTITATIVE DESCRIPTION OF THE POLAR EFFECTS OF SUBSTITUENTS ON THE KINETICS OF THE FREE-RADICAL CHLORINATION OF ALIPHATIC COMPOUNDS BY N-CHLOROPIPERIDINE

The free-radical chlorination of 1-substituted alkanes with electron-withdrawing substituents by N-chloropiperidine in trifluoroacetic acid was studied by the method of competing reactions, and the relative rate constants were obtained for all positions of the substrates.The data on the position selectivity can be described satisfactorily by means of an electrostatic model of the polar effect of the substituent, calculated according to the Kirkwood-Westheimer equation.The obtained characteristics of the electrostatic effect can be successfully applied to calculation of the substrate selectivity and the intermolecular relative rate constants for all the positions, beginning with the third.The Taft equation is unsuitable for description of the effect of substituents on the reaction rate.

Three Component Reactions. XVII. Terminal Reactive Oligooxyethylene Structures from Alkenes, Chlorine and O-Nucleophiles and Their Transformation into Oxathiaalkanes

The reaction of alkenes, chlorine and oxirane, dioxane, ethyleneglycole, oligoethyleneglycoles, the monoethers of oligoethyleneglycoles, ethylene chlorohydrine or α-hydro-ω-chloro-oligooxyethylenes leads to compounds 6-9, which contain mono or oligoether functions and one or two reactive terminal chlorine atoms.Oxathiaalkanes (10 and 12) were obtained in the reaction of such compounds with sodium mercaptides.

THE LONG-RANGE ACTION OF THE POLAR EFFECT OF SUBSTITUENTS ON THE ABSTRACTION OF HYDROGEN IN FREE-RADICAL CHLORINATION PROCESSES

The free-radical chlorination of 1-chloroalkanes between C3 and C6 at 263 deg K was studied under conditions with wide variation in the concentrations of the substrates in benzene.By analysis of the products from chlorination of the pure substrates it was shown that the deactivating effect of the polar substituent does not extend beyond the third carbon atom and is mainly determined by the inductive effect.In the transition to an aromatic solvent the deactivating effect on the substituent extends to the fourth carbon atom.The results are substantiated in terms of a contribution from dipole-dipole interaction between the substituent and the polar form of the transition state to the polar effect of the substituents.

Bromochlorination of Alkenes with Dichlorobromate (1-) ion. IV. Regiochemistry of Bromochlorinations of Alkenes with Molecular Bromine Chloride and Dichlorobromate (1-) Ion

The regioselectivity of the addition of molecular bromine chloride to alkenes is dependent on both the steric and electronic effects of the alkyl substituent.In contrast, the regioselectivity of the addition of dichlorobromate (1-) ion to alkenes is controlled mainly by the steric effect of the substituent.

MECHANISMS OF FREE-RADICAL REACTIONS. XIX. SELECTIVITY OF THE FREE-RADICAL CHLORINATION OF 1-CHLOROALKANES BY N-CHLOROPIPERIDINE

The free-radical chlorination of 1-chloroalkanes ClH2l+1Cl (l = 4-7) by N-chloropiperidine was studied by the method of competing reactions, and the relative constants for all the positions of the investigated substrates were determined.The chlorination is a highly electrophilic process, and the effect of the substituents is transmitted through at least six C-C bonds.The results can be described satisfactorily by means of an electrostatic model of the polar effect of the substituents according to the Kirkwood-Westheimer equation.At the same time an attempt to describe the obtained data by means of the Taft equation led to unsatisfactory results.

Process for dechlorinating organic compounds

Olefinic compounds are made from their vicinally chlorinated organic precursors by dechlorination with metallic magnesium in the presence of a mercury-based promoter, which may be a water-soluble mercury salt or metallic mercury, and of a catalytic amount of iodine. This process is particularly suitable for dechlorinating 4,5-dichloro-dioxolanes to the corresponding dioxoles. 4,5-Difluoro-2,2 bis(trifluoromethyl)-1,3-dioxole, which can be made by this process in a reproducible manner from 4,5-dichloro-4,5-difluoro-2,2-bis(trifluoromethyl)-1,3-dioxolane, is a useful monomer for making amorphous homopolymers and copolymers with tetrafluoroethylene, which are well suited for wire coating, finishes, and transparent glazing for corrosive service.

Three Component Reactions. XVI. Halogenation of Alk-1-enes in the Presence of Ethylene Oxide and Propylene Oxide

The products of the chlorination of alk-1-enes in the presence of ethylene oxide and propylene oxide were investigated in relation to products of the chlorination in the presence of corresponding chloroalcohols 4 and 5.Isomers dominating in the Markovnikov orientation were found in all cases.Two of the three pairs of diastereomeric bischloropropylethers expected for the chlorination of propene in the presence of propylene oxide were identified by capillar GLC and 13C n.m.r. spectroscopy.

Silylaminyl Radicals. Part 2. Free Radical Chain Halogenation of Hydrocarbons using N-Halogenobis(trialkylsilyl)amines

The liquid-phase halogenation of a number of hydrocarbons and of 1-chlorobutane by N-halogenobis(trialkylsilyl)amines has been studied using product analysis techniques.The reactions take place by free radical chain mechanisms which involve the propagation steps generalised in equations (A) and (B) (X=Br or Cl).At 353 K, the molar reactivities of toluene (benzylic C-H) and cyclohexane towards (R3Si)2N+RH(R3Si)2NH+R (A) R+(R3Si)2NXRX+(R3Si)2N (B) (Me3Si)2N are approximately equal and toluene is 5.2 times more reactive than perdeuteriotoluene.The relative rates of hydrogen abstraction by (Me3Si)2N and (ButMe2Si)2N from the primary, secondary, and tertiary C-H groups in 2-methylbutane show that the silylaminyl radicals are not only highly reactive but also sterically demanding.Thus, at 333 K the average primary C-H reactivity is 0.6 times that of the tertiary C-H towards attack by (Me3Si)2N, but 4.2 times that of the tertiary C-H towards attack by the more bulky (ButMe2Si)2N.Silylaminyl radicals are much more reactive in hydrogen abstraction than are analogous dialkylaminyl radicals and this difference is interpreted in terms of thermodynamic and polar effects which arise because of the ?-donor-?-acceptor nature of the trialkylsilyl substituent.