15909-83-8Relevant articles and documents
Kinetics of the Aqueous Periodate Oxidation of Aliphatic Disulfides and Thioethers
Evans, Brian J.,Takahashi Doi, Joyce,Musker, W. Kenneth
, p. 2580 - 2586 (1990)
Water-soluble aliphatic disulfides are oxidatively cleaved by borate-buffered periodate at 23 deg C.The reaction conditions were selected because they are used for the oxidation of methionine in protein modification, and we wanted to test the reactivity of the disulfide linkage in various bifunctional molecules under these conditions.A colorimetric method was developed which uses 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) to determine the concentrations of periodate.The γ-substituted amine-disulfide 1b consumes 4 equiv of periodate at a rate which is accelerated 100-fold over that of 4,4'-dithiodibutanol (1c) and forms the cyclic sulfinamide 3 an sulfonamide 4.To account for the stoichiometry and acceleration, we have proposed intermediates in which a nucleophilic sulfur atom attacks an oxygen atom of periodate to give an anhydride or complex rather than invoking direct oxygen atom transfer.The γ- and δ-hydroxy disulfides 1a and 1c consume 5 equiv of periodate and are oxidized to the sulfonic acids.The rate of DL-methionine (2a) oxidation in water is reported, along with the oxidations of dibutyl sulfide (2c) and of 1,5-dithiacyclooctane (2d) in 50percent aqueous ethanol.The oxidation of 2d is only 2.1 times faster than the oxidation of 2c, showing that the transannular sulfur atom in 2d does not participate in the oxidation.A comparison of the rate of periodate oxidation of disulfides, thioethers, and ethylene glycol under the same conditions shows that it is possible for these processes to be competitive.
1,3-propane sultone preparation method
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Paragraph 0033-0035; 0038-0040; 0043-0045; 0049, (2019/10/01)
The invention relates to a 1,3-propane sultone preparation method, which comprises: S1, completely mixing in a reaction container by using 3-chloropropanol and sodium sulfite as raw materials and using water as a solvent, controlling the temperature at 25-120 DEG C, carrying out a reaction for 4-48 h, carrying out pressure reducing dewatering concentration, adding concentrated hydrochloric acid tothe concentrated liquid, carrying out acidification, controlling the temperature at 0-80 DEG C, stirring for 1-24 h, filtering, and concentrating the filtrate to obtain 3-hydroxypropanesulfonic acid;S2, controlling the temperature of the concentrated liquid obtained in the step S1 at 40-110 DEG C, and carrying out pressure reducing concentrating to carry out dewatering ring closure on the 3-hydroxypropanesulfonic acid in the concentrated liquid to obtain a crude product containing 1,3-propane sultone; and S3, rectifying the crude product containing 1,3-propane sultone to obtain 1,3-propane sultone. According to the present invention, the method has characteristics of short process route, less three-waste and simple post-treatment, wherein the total yield can achieve more than 90%, and the purity of the product can achieve more than 99.9%.
Method for preparing 1,3-propane sultone
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Paragraph 0039; 0041, (2016/10/07)
The invention discloses a method for preparing 1,3-propane sultone. The method includes the steps that (1) 1,3-propanesulfonic acid is prepared: sodium sulfite, sodium bisulfite and allyl alcohol are added into a reactor under the room temperature condition, a pH value is regulated to be 5 to 5.5, infrared radiation induction is adopted, azo diisobutyl nitrile performs catalytic reaction for 2 to 3 hours, concentrated hydrochloric acid is added, the reaction is performed at the temperature of 85 to 90 DEG C for 2 to 3 hours, generated salt is removed through filtration, and n-butyl alcohol is added into filtrate to perform extraction separation so as to obtain the 3-hydroxy-1-propanesulfonic acid; (2) the 1,3-propane sultone is prepared: pyridinium p-toluenesulfonate and zeolites are added, dehydration reaction is performed at the temperature of 50-60 DEG C for 2-3 hours, distillation is performed to obtain 147-149 DEG C of fraction, and calcium oxide is added to perform heating reflux for 1-2 hours to obtain the 1,3-propane sultone. The product prepared by means of the method is high in yield and purity. In addition, the moisture content of the product is mostly above 0.1%, the amplification effect and other problems do not exist, and the method is suitable for industrial production.