Butadiene sulfone

Example 4.4 Butadiene sulfone (or 3-sulfolene) is an intermediate used for the production of solvents. It can be produced from butadiene and sulfur dioxide according to the reaction ... 

This is an exothermic, reversible, homogeneous reaction taking place in a single liquid phase. The liquid butadiene feed contains 0.5 percent normal butane as an impurity. The sulfur dioxide is essentially pure. The mole ratio of sulfur dioxide to butadiene must be kept above 1 to prevent unwanted polymerization reactions. A value of 1.2 is assumed. The temperature in the process must be kept above 65°C to prevent crystallization of the butadiene sulfone but below lOO C to prevent its decomposition. The product must contain less than 0.5 wt% butadiene and less thM 0.3 wt% sulfur dioxide. 

Figure 4.12 The reaction-separation system for the production of butadiene sulfone.

An important aspect of this procedure is the use of latent acid catalysts, such as phenyl hydrogen maleate, phenyl trifluoracetate, and butadiene sulfone. These catalysts reduce the peak exotherm from over 200°C to 130—160°C. The resin catalyst mixture has a working life of up to several days at RT. The elevated temperature of mol ding these latent catalysts generates the corresponding acids, namely, maleic, trifluoracetic, and phenolsulfonic, which cataly2e the resole reaction. Typically, a cycle time of 1—2 min is requited for a mold temperature of - 150° C. 

Butadiene sulfone (butadiene, SOci) CST L f-Butyl catechol 34 12 0.2 LHSV [1]5 192... 

Akbulut has also reported the effect of ultrasound upon the electronitiated homopolymerisation of butadiene sulfone (Fig. 6.21) in MeCN/Bu4NBF4 using platinum electrodes [84]. Interestingly ultrasound did not completely clear the electrode of a polymer film, although it did produce an improvement in the percentage conversion versus time characteristics of the polymerisation. 

Dihydrothiophene 1,1-dioxide (butadiene sulfone, or 3-sulfolene) was purchased from the Aldrich Chemical Company, Inc. 

Kharasch and Fried lander151 162 have studied the photoreaction of bromotrichloromethane with butadiene sulfone XXXVI162 and with 1-octene in the presence of sulfur dioxide.161... 

A plant is to manufacture butadiene sulfone at the rate of 1250 lb/hr from liquid sulfur dioxide and butadiene to be recovered from a crude C4 mixture as starting materials. Construct a flowsheet for the process according to the following description. 

To test the effect of a heteroatom, Starokon et al. [175] studied three five-membered heterocycles with a similar molecular structure, containing the oxygen (2,5-dihy-drofuran), nitrogen (3-pyrrole) and sulfur (butadiene sulfone). Only the oxygen-containing cycle was carboxidized selectively, while the others showed a strong tendency towards side reactions resulting in a set of unidentified products. 

A design has been completed for the production of butadiene sulfone from 1,3 butadiene and sulfur dioxide. Based on the following results from the completed design and the basic company requirements as listed, determine what the selling price of the butadiene sulfone product should be as dollars per pound based on ... 

The total capital investment for the complete plant is 300,000, and it produces 10 million pounds of butadiene sulfone per year. 

Sulfur-hydrogen scalar coupling has been observed for a solution of 2moldm 2,5-dihydrothiophene 1,1-dioxide (butadiene sulfone) 90, in acetone. A partially resolved triplet, of total width 18 Hz, collapses to a singlet, width 7 Hz, when proton decoupling is applied. The major coupling is attributed to a vicinal interaction between the sulfur and olefinic protons, by comparison of the carbon spectrum of diethyl ketone (the carbonyl carbon resonance exhibits a septet) and the sulfur spectrum of sulfolane (the sulfur peak shows no structure). This was confirmed by selectively decoupling at the two relevant proton frequencies in turn. 

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