US2014213799A1PendingUtilityA1

Synthesis of reversibly protected silanes

43
Individually held — no corporate assignee on recordPriority: Nov 8, 2010Filed: Mar 31, 2014Published: Jul 31, 2014
Est. expiryNov 8, 2030(~4.3 yrs left)· nominal 20-yr term from priority
Inventors:Michael Deemer
C07F 7/188C07F 7/1804
43
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Claims

Abstract

The present invention discloses a method for synthesizing a reversibly protected organometallic compound or a reversibly protected silane. This method can be conducted by (1) reacting an organometallic compound with a hydroxyl group containing compound to produce a solution containing the reversibly protected organometallic compound and hydrogen chloride; (2) reacting the solution containing the reversibly protected organometallic compound and the hydrogen chloride with a trialkyl amine to precipitate the hydrogen chloride from the solution; and (3) recovering the reversibly protected organometallic compound from the solution of the reversibly protected organometallic compound.

Claims

exact text as granted — not AI-modified
What is claimed is: 
     
         1 . A method for synthesizing a reversibly protected organometallic compound or a reversibly protected silane which comprises (1) reacting an organometallic compound of the structural formula: A x -MX y  with a hydroxyl group containing compound having a formula selected from the group consisting of: 
       
         
           
           
               
               
           
         
       
       wherein M represents a member selected from the group consisting of silicon, germanium, tin, lead, titanium, hafnium, and zirconium; wherein A represents an unsaturated hydrocarbyl moiety containing at least one non-aromatic double bond; wherein X represents a halogen atom; wherein x and y represent integers from 1 to 3; wherein the sum of x and y is 4; wherein n represents an integer from 1 to about 20; wherein m represents an integer from 0 to 20; wherein Z represents a group —C(R)(R 1 )—; wherein R, R 1 , and R 2  can be the same or different and are selected from the group consisting of hydrogen atoms, alkyl groups containing from 1 to about 12 carbon atoms, aryl groups containing from about 6 to about 18 carbon atoms, alkaryl groups containing from 7 to about 18 carbon atoms, alkoxy groups containing from 1 to about 18 carbon atoms, hydroxy groups, and halide atoms; wherein R* is selected from the group consisting of hydrogen atoms, alkyl groups containing from 1 to about 12 carbon atoms, aryl groups containing from about 6 to about 18 carbon atoms, and alkaryl groups containing from 7 to about 18 carbon atoms; wherein R, R 1 , R 2 , and R* can be bonded together in any combination in cases where R, R 1 , R 2 , and R* are not hydrogen atoms, halide atoms, or hydroxy groups; wherein Y represents a moiety selected from the group consisting of —C(R)(R 1 )—, oxygen, sulfur, nitrogen, and phosphorus;
 wherein Z represents a moiety selected from the group consisting of —C(R)(R 1 ), oxygen, sulfur, nitrogen, and phosphorus; with the proviso that Y and Z can not both represent the moiety —C(R)(R 1 )—; wherein the organometallic compound is reacted with the hydroxyl group containing compound in an organic solvent at a temperature of less than about 100° C. to produce a solution containing the reversibly protected organometallic compound and hydrogen chloride; (2) reacting the solution containing the reversibly protected organometallic compound and the hydrogen chloride with a trialkyl amine to precipitate the hydrogen chloride from the solution to produce a solution of the reversibly protected organometallic compound, wherein step (2) can be carried out concurrently with step (1) or subsequently to step (1); and (3) recovering the reversibly protected organometallic compound from the solution of the reversibly protected organometallic compound. 
 
     
     
         2 . The method as specified in  claim 1  wherein M represents silicon. 
     
     
         3 . The method as specified in  claim 1  wherein the hydroxyl group containing compound is of the formula: 
       
         
           
           
               
               
           
         
       
       wherein R* is selected from the group consisting of hydrogen atoms and alkyl groups containing from 1 to about 12 carbon atoms. 
     
     
         4 . The method as specified in  claim 3  wherein Y represents an oxygen atom. 
     
     
         5 . The method as specified in  claim 4  wherein R and R 1  represent hydrogen atoms. 
     
     
         6 . The method as specified in  claim 5  wherein x represents 1 and wherein y represents 3. 
     
     
         7 . The method as specified in  claim 6  wherein X represents chlorine. 
     
     
         8 . The method as specified in  claim 7  wherein A represents a group of the formula: 
       
         
           
           
               
               
           
         
       
       wherein z represents an integer from 1 to 12. 
     
     
         9 . The method as specified in  claim 8  wherein z represents 3. 
     
     
         10 . The method as specified in  claim 1  wherein the trialkyl amine has alkyl groups that contain from 1 to 4 carbon atoms. 
     
     
         11 . The method as specified in  claim 1  wherein the trialkyl amine is triethyl amine. 
     
     
         12 . The method as specified in  claim 1  wherein the hydroxyl group containing compound is of the formula: 
       
         
           
           
               
               
           
         
       
       wherein R, R 1 , and R 2  can be the same or different and are selected from the group consisting of hydrogen atoms and alkyl groups containing from 1 to about 12 carbon atoms. 
     
     
         13 . The method as specified in  claim 1  wherein step (1) and step (2) are conducted simultaneously. 
     
     
         14 . The method as specified in  claim 1  wherein the hydroxyl group containing compound is of the formula: 
       
         
           
           
               
               
           
         
       
       wherein R, R 1 , and R 2  can be the same or different and are selected from the group consisting of hydrogen atoms and alkyl groups containing from 1 to about 12 carbon atoms. 
     
     
         15 . The method as specified in  claim 1  wherein the reaction of step (1) is conducted at a temperature which is within the range of about 0° C. to about 60° C. 
     
     
         16 . A method for synthesizing a reversibly protected organometallic compound or a reversibly protected silane which comprises (1) reacting an organometallic compound of the structural formula: A x -MX y  with a hydroxyl group containing compound having a formula selected from the group consisting of: 
       
         
           
           
               
               
           
         
       
       wherein M represents a member selected from the group consisting of silicon, germanium, tin, lead, titanium, hafnium, and zirconium; wherein A has a structural formula selected from the group consisting of: 
       
         
           
           
               
               
           
         
       
       wherein z represents an integer from 1 to 12.; wherein X represents a halogen atom; wherein x and y represent integers from 1 to 3; wherein the sum of x and y is 4; wherein n represents an integer from 1 to about 20; wherein m represents an integer from 0 to 20; wherein Z represents a group —C(R)(R 1 )—; wherein R, R 1 , and R 2  can be the same or different and are selected from the group consisting of hydrogen atoms, alkyl groups containing from 1 to about 12 carbon atoms, aryl groups containing from about 6 to about 18 carbon atoms, alkaryl groups containing from 7 to about 18 carbon atoms, alkoxy groups containing from 1 to about 18 carbon atoms, hydroxy groups, and halide atoms; wherein R* is selected from the group consisting of hydrogen atoms, alkyl groups containing from 1 to about 12 carbon atoms, aryl groups containing from about 6 to about 18 carbon atoms, and alkaryl groups containing from 7 to about 18 carbon atoms; wherein R, R 1 , R 2 , and R* can be bonded together in any combination in cases where R, R 1 , R 2 , and R* are not hydrogen atoms, halide atoms, or hydroxy groups; wherein Y represents a moiety selected from the group consisting of —C(R)(R 1 )—, oxygen, sulfur, nitrogen, and phosphorus; wherein Z represents a moiety selected from the group consisting of —C(R)(R 1 ), oxygen, sulfur, nitrogen, and phosphorus; with the proviso that Y and Z can not both represent the moiety —C(R)(R 1 )—; wherein the organometallic compound is reacted with the hydroxyl group containing compound in an organic solvent at a temperature of less than about 100° C. to produce a solution containing the reversibly protected organometallic compound and hydrogen chloride; (2) reacting the solution containing the reversibly protected organometallic compound and the hydrogen chloride with a trialkyl amine to precipitate the hydrogen chloride from the solution to produce a solution of the reversibly protected organometallic compound, wherein step (2) can be carried out concurrently with step (1) or subsequently to step (1); and (3) recovering the reversibly protected organometallic compound from the solution of the reversibly protected organometallic compound. 
     
     
         17 . The method as specified in  claim 16  wherein the hydroxyl group containing compound is of the formula: 
       
         
           
           
               
               
           
         
       
       wherein R* is selected from the group consisting of hydrogen atoms and alkyl groups containing from 1 to about 12 carbon atoms. 
     
     
         18 . The method as specified in  claim 16  wherein the hydroxyl group containing compound is of the formula: 
       
         
           
           
               
               
           
         
       
       wherein R, R 1 , and R 2  can be the same or different and are selected from the group consisting of hydrogen atoms and alkyl groups containing from 1 to about 12 carbon atoms. 
     
     
         19 . The method as specified in  claim 16  wherein the hydroxyl group containing compound is of the formula: 
       
         
           
           
               
               
           
         
       
       wherein R, R 1 , and R 2  can be the same or different and are selected from the group consisting of hydrogen atoms and alkyl groups containing from 1 to about 12 carbon atoms. 
     
     
         20 . A method for synthesizing a reversibly protected organometallic compound or a reversibly protected silane which comprises (1) reacting an organometallic compound of the structural formula: A x -MX y  with a hydroxyl group containing compound having a formula selected from the group consisting of: 
       
         
           
           
               
               
           
         
       
       wherein M represents a member selected from the group consisting of silicon, germanium, tin, lead, titanium, hafnium, and zirconium; wherein A is of the formula: —(CH 2 ) z —SiCl 3 , wherein z represents an integer from 1 to 12.; wherein X represents a halogen atom; wherein x and y represent integers from 1 to 3; wherein the sum of x and y is 4; wherein n represents an integer from 1 to about 20; wherein m represents an integer from 0 to 20; wherein Z represents a group —C(R)(R 1 )—; wherein R, R 1 , and R 2  can be the same or different and are selected from the group consisting of hydrogen atoms, alkyl groups containing from 1 to about 12 carbon atoms, aryl groups containing from about 6 to about 18 carbon atoms, alkaryl groups containing from 7 to about 18 carbon atoms, alkoxy groups containing from 1 to about 18 carbon atoms, hydroxy groups, and halide atoms; wherein R* is selected from the group consisting of hydrogen atoms, alkyl groups containing from 1 to about 12 carbon atoms, aryl groups containing from about 6 to about 18 carbon atoms, and alkaryl groups containing from 7 to about 18 carbon atoms; wherein R, R 1 , R 2 , and R* can be bonded together in any combination in cases where R, R 1 , R 2 , and R* are not hydrogen atoms, halide atoms, or hydroxy groups; wherein Y represents a moiety selected from the group consisting of —C(R)(R 1 )—, oxygen, sulfur, nitrogen, and phosphorus; wherein Z represents a moiety selected from the group consisting of —C(R)(R 1 ), oxygen, sulfur, nitrogen, and phosphorus; with the proviso that Y and Z can not both represent the moiety —C(R)(R 1 )—;
 wherein the organometallic compound is reacted with the hydroxyl group containing compound in an organic solvent at a temperature of less than about 100° C. to produce a solution containing the reversibly protected organometallic compound and hydrogen chloride; (2) reacting the solution containing the reversibly protected organometallic compound and the hydrogen chloride with a trialkyl amine to precipitate the hydrogen chloride from the solution to produce a solution of the reversibly protected organometallic compound, wherein step (2) can be carried out concurrently with step (1) or subsequently to step (1); and (3) recovering the reversibly protected organometallic compound from the solution of the reversibly protected organometallic compound.

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