# US 2020/0399294 A1 · Process for the production of alkyltin halides

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- Number: US 2020/0399294 A1
- Document ID: US20200399294A1
- Status: Published application
- Kind: A1
- Application number: 17/012,090
- Filed: 2020-09-04
- Published: 2020-12-24
- Earliest claimed: 2018-03-06
- Assignees: Galata Chemicals, LLC
- Applicants: Galata Chemicals LLC
- Inventors: Peter FRENKEL; Joseph SALSBURY; Steven McKEOWN
- Web page: https://patentgrep.com/patent/US20200399294A1

## CPC

- C07F 7/2208: {Compounds having tin linked only to carbon, hydrogen and/or halogen}
- B01D 3/40: Extractive distillation
- C07F 7/2296: {Purification, stabilisation, isolation}
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- B01D: SEPARATION (separating solids from solids by wet methods B03B, B03D; by pneumatic jigs or tables B03B; by other dry methods B07; magnetic or electrostatic separation of solid materials from solid materials or fluids, separation by high-voltage electric fields B03C; centrifuges, vortex apparatus B04; presses per se for squeezing-out liquid from liquid-containing material B30B9/02; treatment of water C02F, e.g. softening by ion-exchange C02F1/42; {arrangements of air intake cleaners in gas turbine plants F02C7/05} ; arrangements or mounting of filters in air-conditioning, air-humidification or ventilation F24F13/28)

## Abstract

A process comprising: (a) contacting a feed stream comprising a di-alkyltin dihalide distillate with an alkylation agent, thereby forming an alkylated mixture comprising R4Sn and optionally R3SnX, R2SnX2, or mixtures thereof, where R is a linear, branched or cyclic C1-C20 alkyl, and X is a halide; (b) contacting the alkylated mixture with SnX4, thereby forming an alkyltin halide mixture comprising RSnX3, R2SnX2, and optionally impurities, R3SnX or mixtures thereof; (c) separating by distillation the alkyltin halide mixture to form a mono-alkyltin halide-rich distillate stream and a liquid di-alkyltin halide-rich bottoms stream comprising R2SnX2, RSnX3, and optionally impurities, R3SnX, or mixtures thereof; (d) separating by distillation the di-alkyltin halide-rich bottoms stream, thereby forming the liquid di-alkyltin dihalide distillate comprising R2SnX2, and optionally RSnX3, R3SnX or mixtures thereof, and an impurities-rich bottoms stream; and (e) recycling a part, xrecycle, of the liquid di-alkyltin dihalide distillate to step (a), where xrecycle ranges from greater than 0.0% to 100.0% of the distillate.

## Claims

### Claim 1

A process comprising:
(a) contacting a feed stream comprising a di-alkyltin dihalide distillate with an alkylation agent, thereby forming an alkylated mixture comprising R4Sn and optionally R3SnX, R2SnX2, or mixtures thereof, where R is a linear, branched or cyclic C1-C20 alkyl, and X is a halide;
(b) contacting the alkylated mixture with SnX4, thereby forming an alkyltin halide mixture comprising RSnX3, R2SnX2, and optionally impurities, R3SnX or mixtures thereof;
(c) separating by distillation the alkyltin halide mixture to form a mono-alkyltin halide-rich distillate stream and a liquid di-alkyltin halide-rich bottoms stream comprising R2SnX2, RSnX3, and optionally impurities, R3SnX, or mixtures thereof;
(d) separating by distillation the di-alkyltin halide-rich bottoms stream, thereby forming the liquid di-alkyltin dihalide distillate comprising R2SnX2, and optionally RSnX3, R3SnX or mixtures thereof, and an impurities-rich bottoms stream; and
(e) recycling a part, xrecycle, of the liquid di-alkyltin dihalide distillate to step (a), where xrecycle ranges from greater than 0.0% to 100.0% of the distillate.

### Claim 2 (depends on 1)

The process of claim 1 wherein the liquid di-alkyltin dihalide distillate comprises R2SnX2 and RSnX3.

### Claim 3 (depends on 1)

The process of claim 1 wherein the liquid di-alkyltin dihalide distillate comprises R2SnX2 and R3SnX.

### Claim 4 (depends on 3)

The process of claim 3 wherein the di-alkyltin dihalide distillate further comprises RSnX3.

### Claim 5 (depends on 1)

The process of claim 1 wherein the alkylation agent is selected from a C1-C20 tri-alkylaluminum compound, or a C1-C20 alkylmagnesium halide compound.

### Claim 6 (depends on 1)

The process of claim 1 wherein in step (b) the alkyltin halide mixture further comprises R3SnX.

### Claim 7 (depends on 6)

The process of claim 6 wherein in step (c) the di-alkyltin halide-rich bottoms stream further comprises R3SnX.

### Claim 8 (depends on 1)

The process of claim 1 wherein R is n-octyl.

### Claim 9 (depends on 1)

The process of claim 1 wherein the halide is chloride.

### Claim 10 (depends on 1)

The process of claim 1 wherein RSnX3 is mono-n-octyltin trichloride.

### Claim 11 (depends on 1)

The process of claim 1 wherein R2SnX2 is di-n-octyltin dichloride.

### Claim 12 (depends on 1)

The process of claim 1 wherein xrecycle is 10.0% to 90.0%.

### Claim 13 (depends on 12)

The process of claim 12 wherein xrecycle is 30.0% to 80.0%.

### Claim 14 (depends on 13)

The process of claim 13 wherein xrecycle is 50.0% to 70.0%.

### Claim 15 (depends on 1)

The process of claim 1 wherein the liquid di-alkyltin dihalide distillate of step (c) has a boiling point 150 to 250° C. at less than 10 mmHg.

### Claim 16 (depends on 1)

The process of claim 1 wherein the mono-alkyltin trichloride-rich distillate stream of step (c) comprises 90.0 to 100 wt % RSnX3, 0.0 to 10.0 wt % R2SnX2 and less than 1.0 wt % R3SnX.

### Claim 17 (depends on 1)

The process of claim 1 wherein the liquid di-alkyltin dihalide distillate of step (c) comprises 3.0 to 30.0 wt % RSnX3, 70.0 to 97.0 wt % R2SnX2, 0 to 5.0 wt % R3SnX and less than 5.0 wt % impurities.

### Claim 18 (depends on 1)

The process of claim 1 further comprising reacting the liquid di-alkyltin dihalide distillate with a mercaptoacetic acid ester selected from iso-octylmercaptoacetate, 2-ethylhexylmercaptoacetate, and n-octylmercaptoacetate, thereby forming a di-alkyltin bis(octyl mercaptoacetate)-containing stabilizer.

### Claim 19 (depends on 18)

The process of claim 18 wherein the mercaptoacetic acid ester is 2-ethylhexyl mercaptoacetate.

### Claim 20 (depends on 18)

The process of claim 18 where the stabilizer is an octyltin thioglycolate stabilizer.

### Claim 21 (depends on 20)

The process of claim 20 wherein the octyltin thioglycolate stabilizer has a Gardner color value of at most 3.

### Claim 22 (depends on 21)

The process of claim 21 wherein the Gardner color value is at most 2.

### Claim 23 (depends on 22)

The process of claim 22 wherein the Gardner color value is at most 1.

### Claim 24 (depends on 1)

The process of claim 1 wherein the impurities are residual raw materials and by-products from steps (a) to (e).

### Claim 25 (depends on 24)

The process of claim 24 wherein the impurities are ligand precursors, hydrolyzed ligand precursors, tin halides, solvents, alkenes, alkyl halides, neutralization salts or mixtures thereof.

### Claim 26 (depends on 1)

The process of claim 1 wherein the Gardner color value of the alkyltin halide mixture formed in step (a) ranges from 0 to 3.

### Claim 27 (depends on 1)

The process of claim 1 further comprising reacting the liquid di-alkyltin dihalide distillate with an organic acid selected from the group consisting 2-ethylhexanoic acid, neodecanoic acid, lauric acid, myristic acid, oleic acid, and stearic acid, thereby forming a di-alkyltin bis-carboxylate-containing stabilizer or a catalyst.

### Claim 28 (depends on 1)

The process of claim 1 further comprising reacting the liquid di-alkyltin dihalide distillate with water, thereby forming a di-alkyltin oxide-containing catalyst.

### Claim 29

A process comprising:
(a) contacting a feed stream comprising a liquid di-alkyltin dihalide distillate with a tri-alkyl aluminum compound, thereby forming an alkyltin halide mixture comprising RSnX3, R2SnX2, impurities, and optionally R3SnX;
(b) separating by distillation the alkyltin halide mixture to form a mono-alkyltin halide-rich distillate stream and a liquid di-alkyltin-rich bottoms stream comprising R2SnX2, impurities, and optionally RSnX3, R3SnX or mixtures thereof;
(c) separating by distillation the di-alkyltin halide-rich bottoms stream, thereby forming the liquid di-alkyltin dihalide distillate comprising R2SnX2, and optionally RSnX3, R3SnX or mixtures thereof; and an impurities-rich bottoms stream; and
(d) recycling a fraction, xrecycle, of the liquid di-alkyltin dihalide distillate to step (a), where xrecycle ranges from greater than 0.0% to 100.0% of the distillate product.