1,3, 5-Dioxazine Derivatives, Method of Preparation and Application Thereof as Sulfide Scavenger

Abstract

The present disclosure relates to 1,3,5-dioxazine derivatives of formula (I) capable of reducing or eliminating hydrogen sulfide and other objectionable sulfides from oil field produced hydrocarbon fluids such as petroleum, fuel oil, gasoline, diesel, liquid propane, liquid butane, an aquaculture and production/processing of syngas/natural gas. The present disclosure further provides a method for preparing 1, 3, 5-dioxazine derivatives of formula I, and a method for scavenging sulfur-based species including, but not limited to hydrogen sulfide or alkyl/aryl mercaptans from a medium.

I claim: 
     
         1 . A compound of formula (I): 
       
         
           
           
               
               
           
         
         wherein: 
         “n” is a numeral selected from 0 to 10; 
         R 1  is substituted or unsubstituted amine group; or a substituted or unsubstituted, linear or branched, cyclic or acyclic C 2  to C 20  alkyl, C 2 -C 28  thioether, C 2 -C 28  alkanol, C 2 -C 28  phosphorous containing alkyl or C 2 -C 28  ether group; or a substituted or unsubstituted aromatic or heteroaromatic group; and 
         R 2  is H, —OH, —SH, —NH 2 , linear or branched C 1 -C 15  alkyl group, aromatic, heteroaromatic, bridged ring, cycloalkyl, heteroalkyl, alkyl aromatic or a 1,3,5-dioxazine group. 
       
     
     
         2 . The compound as claimed in  claim 1 , wherein said compound is selected from a group comprising: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         wherein, x, y and z independently represent a numeral ranging from 0 to 10. 
       
     
     
         3 . A method for preparing the compound of formula I as claimed in  claim 1 , wherein the method comprises reacting at least one amine compound with any or a combination of aqueous formaldehyde and paraformaldehyde under conditions effective to obtain the compound of formula I. 
     
     
         4 . The method according to  claim 3 , wherein the at least amine compound is selected from any or a combination of 1, 2-diaminoethane, 1,3-Diaminopropane, 1,4-Diaminobutane, 1, 4-Phenylenedimethanamine, N, N-Bis(2-aminoethyl)-1, 2-ethanediamine, Diethylenetriamine, triethylenetetramine, polyalkylamines and derivatives thereof. 
     
     
         5 . The method according to  claim 3 , wherein the any or a combination of aqueous formaldehyde and paraformaldehyde has a concentration ranging from 5 to 50%. 
     
     
         6 . The method according to  claim 3 , wherein a molar ratio of the at least one amine compound to the any or a combination of aqueous formaldehyde and paraformaldehyde for one —NH 2  group ranges from about 1:1 to about 1:20. 
     
     
         7 . A method for reducing hydrogen sulfide or alkyl/aryl mercaptan in a medium, the method comprising contacting the hydrocarbon fluid with an effective amount of a compound of formula (I) according to  claim 1 . 
     
     
         8 . The method as claimed in  claim 7 , wherein said medium is any of an oil field produced hydrocarbon fluid, a natural gas and an aquaculture. 
     
     
         9 . The method as claimed in  claim 7 , wherein said step of contacting the hydrocarbon fluid with the effective amount of the compound of formula (I) is carried out at a temperature ranging from about 0° C. to about 90° C. 
     
     
         10 . The method as claimed in  claim 7 , wherein said step of contacting the hydrocarbon fluid with the effective amount of the compound of formula (I) is carried out for a length of time ranging from about 5 seconds to about 240 minutes.