# US 4,400,527 A · Producing oximinosilanes, oximinogermanes and oximinostannanes

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- Number: US 4,400,527 A
- Document ID: US4400527A
- Status: Granted
- Kind: A
- Application number: 06/331,694
- Filed: 1981-12-17
- Granted: 1983-08-23
- Earliest claimed: 1981-12-17
- Assignees: Allied Corporation
- Inventors: Chempolil T. Mathew; Harry E. Ulmer
- Web page: https://patentgrep.com/patent/US4400527A

## CPC

- C07F 7/30: Germanium compounds
- C07F 7/0892: {Compounds with a Si-O-N linkage}
- C07F 7/2224: {Compounds having one or more tin-oxygen linkages}
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)

## Abstract

A Group IVa metal halide such as methyl trichlorosilane is reacted with an oxime compound such as methyl ethyl ketone oxime in the absence of a base to form in high yields a product oximinosilane, oximinogermane or oximinostannane (e.g. methyl tris(methyl ethyl ketoximo)silane) and a by-product oxime hydrohalide. The oxime above that found in the product may be recovered by neutralization of the by-product oxime hydrohalide.

## Claims

### Claim 1

A process for the production of Group IVa metal oximates which comprises:
reacting in the liquid phase a Group IVa metal halide of the formula P.sub.4-n MX.sub.n with an oxime compound of the formula R'R"C.dbd.NOH, at a mole ratio of oxime compound to Group IVa metal halide of at least 2n:1;
separating the product of the formula
(R'R"C.dbd.NO).sub.n MR.sub.4-n
from the by-product oxime hydrohalide of the formula R'R"C.dbd.NOH.HX by separating a liquid organic phase consisting essentially of the product from a phase consisting essentially of oxime hydrohalide;
reacting the liquid organic phase consisting essentially of the product with dry base to convert oxime hydrohalide impurity to oxime compound and solid salt;
removing the solid salt from the remaining liquid;
distilling the remaining liquid to remove any unreacted oxime compound and any oxime compound formed upon reaction with dry base; and
recovering the product as the bottom after distillation;
wherein R is alkyl of 1-6 carbons, alkenyl of 2-6 carbons, aryl, aralkyl, cycloalkyl or halogen-substituted forms thereof; M is Si, Ge or Sn; X is Cl, Br or I; n is 1 to 4; and R' and R" are each independently H, alkyl of 1-6 carbons, aryl, cycloalkyl, aralkyl or any of them substituted by halogen, or R' and R" are together (CH.sub.2).sub.m wherein m is 3 to 7, or alkyl or halosubstituted forms thereof.

### Claim 2 (depends on 1)

The process of claim 1 wherein M is Si.

### Claim 3 (depends on 2)

The process of claim 2 wherein X is Cl.

### Claim 4 (depends on 3)

The process of claim 3 wherein n is 3.

### Claim 5 (depends on 1, 2, 3, 4)

The process of claim 1 or 2 or 3 or 4 wherein R is alkyl of 1-6 carbons.

### Claim 6 (depends on 5)

The process of claim 5 wherein R is methyl.

### Claim 7 (depends on 1, 2, 3, 4)

The process of claim 1 or 2 or 3 or 4 wherein R is vinyl.

### Claim 8 (depends on 1)

The process of claim 1 wherein R' is methyl and R" is ethyl.

### Claim 9 (depends on 1)

The process of claim 1 wherein R' and R" are each methyl.

### Claim 10 (depends on 1)

The process of claim 1 wherein R' and R" are together (CH.sub.2).sub.5.

### Claim 11 (depends on 1, 2, 3, 4)

The process of claim 1 or 2 or 3 or 4 wherein said mole ratio of oxime compound to Group IVa metal halide is between about 2n:1 and about 2.2n:1.

### Claim 12 (depends on 1)

The process of claim 1 wherein said dry base is ammonia and said solid salt is a solid ammonium salt.

### Claim 13 (depends on 1)

The process of claim 1 wherein the phase consisting essentially of oxime hydrohalide is then reacted with ammonia to form solid ammonium halide and oxime compound.

### Claim 14 (depends on 1)

The process of claim 1 wherein the phase consisting essentially of oxime hydrohalide is then reacted with aqueous base to form a two-phase system of a first phase consisting essentially of oxime compound and a second phase consisting essentially of water and the halide salt of said base.

### Claim 15 (depends on 14)

The process of claim 14 wherein the first phase consisting essentially of oxime compound is separated from the second phase consisting essentially of water and the halide salt of said base; and the first phase is dried to a water level less than 1,000 ppm and recycled to said reacting step.

### Claim 16 (depends on 1)

The process of claim 1 wherein a volatile, inert organic solvent is present in the reaction mixture, is present in the liquid organic phase and in the remaining liquid and is removed with the oxime compound by distilling.