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US 2017/0362177 A1Published application
Methods of manufacturing certain substituted sulfilimines
AssigneeDow AgroSciences LLC
InventorsKurt D. Olson, Aaron A. Shinkle
Life of this patent
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Abstract
Provided are methods and/or systems to convert sulfide intermediates to sulfilimines using a series of continuous loop reactors instead of a batch reactor. The advantages of the methods and systems provided include improved total yield, improved heat management, improved phase mixing, and/or improved volume management.
Claims22
A method of preparing a sulfilimine of Formula (I),
- wherein X represents halogen, C1-C4 alkyl or C1-C4 haloalkyl;
- comprising,
- (a) mixing a solution cyanamide, a solution of hypochlorite, and a solvent in a first continuous loop reactor;
- (b) transferring the mixture of Step (a) into a second continuous loop reactor;
- (c) adding a sulfide of Formula (II) into the second continuous loop reactor which reacts with the mixture of Step (a) to form the sulfilimine,
- wherein X is as previously defined;
- and
- (d) decanting the aqueous phase giving an organic phase containing a sulfilimine of Formula (I).
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A system of preparing a sulfilimine of Formula (I),
- wherein X represents halogen, C1-C4 alkyl or C1-C4 haloalkyl;
- comprising,
- (a) mixing a solution of cyanamide, a solution of hypochlorite, and a solvent in a first continuous loop reactor;
- (b) transferring the mixture of Step (a) into a second continuous loop reactor;
- (c) adding a sulfide of Formula (II) into the second continuous loop reactor which reacts with the mixture of Step (a) to form the sulfilimine,
- wherein X is as previously defined;
- (d) decanting the aqueous phase giving an organic phase containing a sulfilimine of Formula (1), and
- (e) back-extracting the aqueous phase decanted in step (c) with additional solvent to recover additional sulfilimine of Formula (1) to combine with the organic phase of step (d)
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A method of reducing solid formation and/or gas release after a conversion reaction from a sulfide of Formula (II),
- wherein X represents halogen, C1-C4 alkyl or C1-C4 haloalkyl,
- into a sulfilimine of Formula (I),
- wherein X is as previously defined;
- comprising,
- quenching the conversion reaction by raising the temperature between 50° C. and 95° C. and/or feeding a solution of sulfur dioxide.
2 more elements
Dependencies are inferred from the claim text.