Process of manufacturing organosilicon products with improved quality using heterogeneous precious metal catalysts
View Patent ↗A process for manufacturing an organosilicon product having a stabilized low color and no formation of black particles during storage includes (a) reacting an unsaturated compound with a silicon compound having a reactive Si—H bond under hydrosilylation conditions in a reaction zone in the presence of a heterogeneous precious metal catalyst to provide an organosilicon product having a color of less than 40 pt/co; (b) separating the heterogeneous precious metal catalyst from the organosilicon product; and (c) recovering the heterogeneous precious metal catalyst.
1. A process for manufacturing an organosilicon product having as stabilized low color and no formation of black particles during storage, the process comprising the steps of
a) reacting an unsaturated compound with a silicon compound having a reactive Si—H bond under hydrosilylation conditions in a reaction zone in the presence of a heterogeneous precious metal catalyst to provide an organosilicon product having a color of less than 40 pt/co, wherein the unsaturated compound is 1-octene or Eugenol;
b) separating the heterogeneous precious metal catalyst from the organosilicon product; and
c) recovering the heterogeneous precious metal catalyst,
wherein the organosilicon product is a component in at least one of a personal care composition, an agricultural composition, a home care composition, a polyurethane foam composition, or a plastic additive composition.
2. The process of claim 1 wherein steps (b) and (c) are performed without the use of distillation or devolatilization.
3. The process of claim 1 wherein the color of the product is less than 30 pt/co.
4. The process of claim 1 wherein the color of the product is less than 20 pt/co.
5. The process of claim 1 wherein the color of the product is less than 10 pt/co.
6. The process of claim 1 wherein the silicon compound is a silane having the formula:
(R 1 ) u (R 2 O) v X w SiH 4−u−v−w
wherein
R 1 and R 2 can be the same or different alkyl groups having from 1 to 5 carbon atoms
X is a halogen element,
u=0 to 3,
v=0 to 3,
w=0 to 3, provided that u+v+w is at least 1 and at the most 3.
7. The process of claim 6 wherein the slime is triethoxysilane wherein R 2 is ethyl, u is 0, v is 3 and w is 0.
8. The process of claim 1 wherein the silicon compound is a siloxane having the formula:
(M) a (M′) b (D) c (D′) d (M) e (M′) f
wherein
M=(R 3 )(R 4 )(R 5 )SiO 1/2 ,
M′=(R 6 )(R 7 )HSiO 1/2 ,
D=(R 8 )(R 9 )SiO 2/2
D′=)(R 10 )HSiO 2/2
and
R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 can be the same or different alkyl or alkoxy groups having from 1 to 5 carbon atoms,
a=0 or 1
b=0 or 1, provided that a+b=1
c=0 to 100
d=0 to 100, provided that c+d is at least 1
e=0 or 1, and
f=0 or 1, provided that e+f=1.
9. The process of claim 8 wherein the silicon compound has the formula MD′M wherein R 3 , R 4 , R 5 and R 10 are each methyl, a is 1, c is 0, d is 1 and e is 1.
10. The process of claim 8 wherein the silicon compound has the formula M′D 45 M′ wherein R 6 , R 7 , R 8 and R 9 are each methyl, b is 1, c is 45, d is 0 and f is 1.
11. The process of claim 8 wherein the silicon compound has the formula M′D 15 M′ wherein R 6 , R 7 , R 8 and R 9 are each methyl, b is 1, c is 15, d is 0 and f is 1.
12. The process of claim 8 wherein the silicon compound has the formula MD 2 D′ 1 M wherein R 3 , R 4 , R 5 , R 8 , R 9 and R 10 are each methyl, a is 1, c is 2, d is 1 and e is 1.
13. The process of claim 8 wherein the silicon compound has a formula MD 13 D′ 5 M wherein R 3 , R 4 , R 5 , R 8 , R 9 and R 10 are each methyl, a is 1, c is 13, d is 5 and e is 1.
14. The process of claim 1 wherein the silicon compound is a silicon polymer.
15. The process of claim 1 wherein the unsaturated compound is 1-octene.
16. The process of claim 1 wherein said hydrosilylation is conducted in a fixed bed continuous process.
17. The process of claim 1 wherein the unsaturated compound is Eugenol.
18. The process of claim 1 wherein the precious metal catalyst comprises a noble metal selected from the group consisting of Pt, Pd, Rh, Ru, Ir and Os loaded on an organic polymeric support or an inorganic support selected from the group consisting of activated carbon, functionalized or non-functionalized silica, alumina, zeolite, nanoparticles etc.
19. The process of claim 18 wherein the precious metal catalyst comprises platinum supported on silica spheres having a particle diameter of about 1.0 mm, platinum supported on alumina powder, platinum supported on silica gel with particle size of 300-500 μm.
20. The process of claim 1 wherein said hydrosilylation is conducted in a batch process.
21. The process of claim 20 wherein the separation of the heterogeneous precious metal catalyst from the organosilicon product is performed by filtration or decantation after the hydrosilyltion reaction has been completed.
22. The process of claim 20 wherein the hydrosilylation reaction conditions include a temperature of from about 25 to 200° C., a pressure of up to about 500 psig, a batchtime of from about 5 minutes to one week, and a catalyst concentration in the batch content of from 1 to 5,000 ppm Pt.
23. The process of claim 1 wherein said hydrosilylation is conducted in a continuous fixed bed reactor.
24. The process of claim 23 wherein the organosil icon product out of fixed bed reactor is free of precious metal catalyst.
25. The process of claim 23 wherein the hydrosilylation reaction conditions include a reaction zone temperature of from at 25 to 200° C., a pressure of up to about 500 psig, a residence time of from about 1 minute to 24 hours.
26. The process of claim 1 wherein recovering of the precious metal is accomplished without distillation.
27. The process of claim 1 wherein the catalyst recovery is accomplished by incineration.
28. A personal care composition comprising the organosilicon product prepared in accordance with the process of claim 1 .
29. A plastic additive composition comprising the organosilicon product prepared in accordance with the process of claim 1 .
30. An agricultural composition comprising, the organosilicon product prepared in accordance with the process of claim 1 .
31. A home care composition comprising the organosilicon product prepared in accordance with the process of claim 1 .
32. A polyurethane foam comprising the organosilicon product prepared in accordance with the process of claim 1 .
33. An organosiloxane product prepared in accordance with the process of claim 1 .
34. An organosilane product prepared in accordance with the process of claim 1 .
35. A process for manufacturing an organosilicon product having a stabilized low color and no formation of black particles during storage, the process comprising the steps of:
a) combining an unsaturated compound and a silicon compound having a reactive Si—H bond a reactant mixing vessel to provide a feed stream;
b) reacting the unsaturated compound and silicon compound under hydrosilylation conditions in a reaction zone in the presence of a heterogeneous precious metal catalyst to provide an organosilicon product having a color of less than 40 pt/co, wherein said hydrosilylation is conducted in a fixed bed batch process with recirculation of at least some of the product back to the reactant mixing vessel;
c) separating the heterogeneous precious metal catalyst from the organosilicon product; and
d) recovering the heterogeneous precious metal catalyst,
wherein the organosilicon product is a component in at least one of a personal care composition, an agricultural composition, a home care composition, a polyurethane foam composition, or a plastic additive composition.
36. A process for manufacturing an organosilicon product having a stabilized low color and no formation of black particles daring storage, the process comprising the steps of
a) reacting an unsaturated compound with, a silicon compound having a reactive Si—H bond under hydrosilylation conditions in a reaction zone in the presence of a heterogeneous precious metal catalyst to provide an organosilicon product having a color of less than 40 pt/co, wherein the hydrosilylation reaction is conducted in a continuous fixed bed reactor in a single pass mode wherein the reaction temperature is from 132 degrees C. to 150 degrees C., the space time yield is from 11.47 to 16.45 g product/(hour g catalyst) and the unsaturated compound is reacted in a mote excess of from 5 mol % to 15 mol %;
b) separating the heterogeneous precious metal catalyst from the organosilicon product; and
c) recovering the heterogeneous precious metal catalyst,
wherein the organosilicon product is a component in at least of a personal care composition, an agricultural composition, a home care composition, a polyurethane foam composition, or a plastic additive composition.