Methods to produce organotin compositions with convenient ligand providing reactants

Patent metadata

Field	Value
Publication number	US-12595272-B2
Application number	US-202117410316-A
Country	US
Kind code	B2
Filing date	Aug 24, 2021
Priority date	Aug 25, 2020
Publication date	Apr 7, 2026
Grant date	Apr 7, 2026

Abstract

Synthesis reactions are described to efficiently and specifically form compounds of the structure RSnL 3 , where R is an organic ligand to the tin, and L is hydrolysable ligand or a hydrolysis product thereof. The synthesis is effective for a broad range of R ligands. The synthesis is based on the use of alkali metal ions and optionally alkaline earth (pseudo-alkaline earth) metal ions. Compounds are formed of the structures represented by the formulas RSn(C≡CSiR′ 3 ) 3 , R′R″ACSnL 3 , where A is a halogen atom (F, Cl, Br or I) or an aromatic ring with at least one halogen substituent, R′R″ (R″O) CSnL 3 or R′R″ (N≡C) CSnZ 3 .

First claim

What is claimed is:

1 . A method for forming an alkali metal tin composition, the method comprising:
reacting (A) ML, wherein M is Li, Na, K, Cs or a combination thereof and L is a dialkylamide represented by the formula —NR′ 2 or an acetylide represented by the formula —C≡CR S , wherein R 5 is SiR″ 3 or R′, the three R″ are independently H or R′, and the R′ are independently a hydrocarbyl group with from 1 to 31 carbon atoms and optional unsaturated carbon-carbon bonds, optional aromatic groups and optional hetero atoms, (B) tin (II) halide, represented by the formula SnX 2 , wherein X is F, Cl, Br, I or a mixture thereof, in an organic solvent to form an alkali metal tin composition, wherein the alkali metal tin composition comprises a SnL 3 moiety, which is Sn(NR′ 2 ) 3 or Sn(C≡CR S ) 3 , present with associated metal cations comprising M, and (C) M′″X 2 , wherein M′″ is beryllium, magnesium, calcium, strontium, barium, zinc, cadmium, mercury or a combination thereof and X═F, Cl, Br, I or a mixture thereof, to form an alkali metal alkaline earth metal/pseudo-alkaline earth metal tin composition.

2 . The method of claim 1 wherein M″′X 2 is ZnCl 2 .

3 . The method of claim 1 wherein the reaction of ML and SnX 2 further comprises reacting with M′OR 0 , where M′ is Na, K, Cs or a combination thereof and R 0 is a hydrocarbyl group with from 1 to 31 carbon atoms and optional unsaturated carbon-carbon bonds, optional aromatic groups and optional hetero atoms, and wherein the associated metal cations further comprise M′.

4 . The method of claim 1 wherein M is Li and/or L is an acetylide.

5 . The method of claim 3 wherein M is Li and M′ is K.

6 . The method of claim 1 wherein reacting ML and tin (II) halide in an organic solvent is initiated at a temperature of no more than about 0° C. and the reaction is continued for a time of at least about two minutes.

7 . The method of claim 1 wherein R′ is methyl(CH 3 —), ethyl(CH 3 CH 2 —), isopropyl(CH 3 CH 3 HC—), t-butyl((CH 3 ) 3 C—), t-amyl(CH 3 CH 2 (CH 3 ) 2 C—), sec-butyl(CH 3 (CH 3 CH 2 )CH—), neopentyl(CH 3 ) 3 CCH 2 —), cyclohexyl, cyclopentyl, cyclobutyl, or cyclopropyl.

8 . The method of claim 1 wherein the molar ratio of ML to tin (II) halide is approximately 3:1 and M″′ to Sn is approximately 1:1.

9 . An alkali metal alkaline earth metal/pseudo-alkaline earth metal tin composition formed according to the method of claim 1 .

10 . A method for forming an alkali metal tin composition, the method comprising:
reacting ML, wherein M is Li, Na, K, Cs or a combination thereof and L is an acetylide represented by the formula-C≡CR S , wherein R S is SiR″ 3 or R′, the three R″ are independently H or R′, and the R′ are independently a hydrocarbyl group with from 1 to 31 carbon atoms and optional unsaturated carbon-carbon bonds, optional aromatic groups and optional hetero atoms, and tin (II) halide, represented by the formula SnX 2 , wherein X is F, Cl, Br, I or a mixture thereof, in an organic solvent to form an alkali metal tin composition, wherein the alkali metal tin composition comprises a SnL 3 moiety, which is Sn(C≡CR S ) 3 , present with associated metal cations comprising M.

11 . The method of claim 10 wherein the reaction of ML and SnX 2 further comprises reacting with M′OR 0 , where M′ is Na, K, Cs or a combination thereof and R 0 is a hydrocarbyl group with from 1 to 31 carbon atoms and optional unsaturated carbon-carbon bonds, optional aromatic groups and optional hetero atoms, and wherein the associated metal cations further comprise M′.

12 . The method of claim 10 wherein M is Li.

13 . The method of claim 10 wherein the reaction is initiated at a temperature of no more than about 0° C. and the reaction is continued for a time of at least about two minutes.

14 . The method of claim 10 wherein R′ is methyl(CH 3 —), ethyl(CH 3 CH 2 —), isopropyl(CH 3 CH 3 HC—), t-butyl((CH 3 ) 3 C—), t-amyl(CH 3 CH 2 (CH 3 ) 2 C—), sec-butyl(CH 3 (CH 3 CH 2 )CH—), neopentyl(CH 3 ) 3 CCH 2 —), cyclohexyl, cyclopentyl, cyclobutyl, or cyclopropyl.

15 . The method of claim 10 wherein the molar ratio of ML to tin (II) halide is approximately 3:1.

16 . An alkali metal tin composition formed according to the method of claim 10 .

17 . The method of claim 1 wherein M is Li.

Assignees

• Inpria Corp

Inventors

• Edson Joseph B
• Cardineau Brian J
• Earley William
• Huihui-Gist Kierra
• Lamkin Thomas J
• Jilek Robert E

Classifications

• C07F7/2224 Primary

  Compounds having one or more tin-oxygen linkages · CPC title

• C07F7/2208

  Compounds having tin linked only to carbon, hydrogen and/or halogen · CPC title

• C07F7/2284 Primary

  Compounds with one or more Sn-N linkages · CPC title