US 2012/0071650 A1Published application

Method for producing aminoorganosilanes

AssigneeWacker Chemie AG

InventorMichael STEPP

Life of this patent

Estimating the term…

Loading patent…

Abstract

The invention relates to a method (a) for producing aminoorganyltriorganylsilanes of the general formula (1) R′3-nR1nSi—R2—NR3R4 (1), a method (b) for producing cyclic aminosilanes of the general formula (4), and a method (III) for producing silylorganoamines of the general formula (7) R013-tR11tSi—R12—NR13—R14—SiR023-sR15s (7), wherein amines are reacted with halogen organylsilanes, wherein R′, R1, R2, R3, R4, R, R5, R6, R01, R02, R11, R12, R13, R14, R15, n, and s have the meanings specified in claims 1 to 3, wherein after the reaction, the ammonium halides of the amines produced as by-products are released by adding a base (B) to the reaction mixture, the amines are removed from the reaction mixture by distillation, two liquid phases are formed by further adding base (B) to the reaction mixture, wherein the one phase contains at least 90 wt % of the hydrohalide of the base (B) and said phase is separated.

Claims24

Dependent claims

A method (I) for producing an aminoorganyltriorganylsilane of the general formula (1)

R′3-nR1nSi—R2—NR3R4 (1),
by reacting a cyclic or acyclic amine of the general formula (2),
H—NR3R4 (2)
with a (haloorganyl)silane of the general formula (3)
R′3-nR1nSi—R2—X (3),
in which
R′ is an acyloxy radical or an alkoxy radical having in each case 1-10 C atoms,
R1 is a hydrocarbon radical having 1-10 C atoms,
R2 is a divalent hydrocarbon radical having 1-10 C atoms,
R3, R4, independently of one another, are hydrogen or a hydrocarbon radical having 1-10 C atoms, it also being possible for R3, R4 to be linked to one another and for a resulting cycle also to contain further heteroatoms, NH groups or NR2a groups,
R2a is a divalent hydrocarbon radical having 1-10 C atoms,
n is a number equal to 0, 1, 2 or 3 and
X is chlorine, bromine or iodine,
the reacting comprising the successive steps:
a) reaction of 1.1 to 100 mol of the amine of the general formula (2) per mole of the (haloorganyl)silane of the general formula (3) in a reaction mixture at a temperature of from 0 to 250° C., an ammonium halide of the amine of the general formula (2) being formed as a byproduct in addition to the silane of the general formula (1),
b) addition of a base (B) to the reaction mixture, the base (B) containing at least 2 mol of basic functional groups per mole, double decomposition occurring in which the amine of the general formula (2) is liberated and base (B) is added in an amount such that at least 1.6 mol of the basic functional groups of the base (B) are present as hydrogen halide adduct,
c) distillation of the amine of the general formula (2) out of the reaction mixture,
d) addition of base (B) to the reaction mixture in an amount sufficient to form two liquid phases, one phase containing at least 90% by weight of a hydrohalide of the base (B) and
e) removal of the liquid phase which contains at least 90% by weight of the hydrohalide of the base (B).

16 more elements

A method (II) for producing a cyclic aminosilane of the general formula (4)

by reacting an amine of the general formula (5),
H2NR7 (5)
with a (haloorganyl)silane of the general formula (6)
(R2)Y1Si—R5—Y2 (6),
in which
R5 is a divalent hydrocarbon radical having 1-10 C atoms in which a hydrocarbon chain may be interrupted by carbonyl groups, carboxyl groups, oxygen atoms, NH or NR8 groups,
R6 is hydrogen or a hydrocarbon radical having 1-10 C atoms which may be substituted by halogen atoms, OH groups and —NH2—, —NHR8, NR82 groups,
R7 is hydrogen or a hydrocarbon radical having 1-10 C atoms which may be substituted by halogen atoms, OH groups and —NH2, —NHR8, NR82 groups,
R is a hydrocarbon radical, an alkoxy radical having in each case 1-10 C atoms,
R8 is a hydrocarbon radical having 1-10 C atoms, and Y1 and Y2 are chlorine, bromine or iodine,
the reacting comprising the successive steps:
a) reaction of 1.1 to 1000 mol of the amine of the general formula (5) per mole of the (haloorganyl)silane of the general formula (6) in a reaction mixture at a temperature of from 0 to 300° C., an ammonium halide of the amine of the general formula (5) being formed as a byproduct in addition to the silane of the general formula (4),
b) addition of a base (B) to the reaction mixture, the base (B) containing at least 2 mol of basic functional groups per mole, double decomposition occurring, in which the amine of the general formula (5) is liberated and base (B) is added in an amount such that at least 1.6 mol of the basic functional groups of the base (B) are present as hydrogen halide adduct,
c) distillation of the amine of the general formula (5) out of the reaction mixture,
d) addition of base (B) to the reaction mixture in an amount sufficient to form two liquid phases, one phase containing at least 90% by weight of a hydrohalide of the base (B), and
e) removal of the liquid phase which contains at least 90% by weight of the hydrohalide of the base (B).

13 more elements

A method (III) for producing a silylorganoamine of the general formula (7)

R013-tR11tSi—R12—NR13—R14—SiR023-sR15s (7)
by reacting an (aminoorganyl)silane of the general formula (8),
H—NR13—R14—SiR02d-sR15s (8)
with a (haloorganyl)silane of the general formula (9)
R013-tR11tSi—R12—Z (9)
in which
R01 and R02 are each an alkoxy radical having in each case 1-10 C atoms,
R11 and R15 are each a hydrocarbon radical having 1-10 C atoms,
R12 is a divalent hydrocarbon radical having 1-10 C atoms wherein a hydrocarbon chain may be interrupted by carbonyl groups, carboxyl groups, oxygen atoms or sulfur atoms,
R14 is a divalent hydrocarbon radical having 1-10 C atoms wherein the hydrocarbon chain may be interrupted by carbonyl groups, carboxyl groups, oxygen atoms, sulfur atoms, NH or NR18 groups, where R18 has the same meaning as R11, R15.
R13 is hydrogen, a hydrocarbon radical having 1-10 C atoms, or a radical of the general formula R033-oR16oSi—R17— where
R16 has the same meaning as R11 and R15,
R17 has the same meaning as R12 and R14, and
R03 has the same meaning as R01 and R02, and
s, t and o are each independently a number equal to 0, 1, 2 or 3, and
Z is chlorine, bromine or iodine,
the reacting comprising the successive steps:
a) reaction of 1.1 to 100 mol of the amine of the general formula (8) per mole of the (haloorganyl)silane of the general formula (9) in a reaction mixture at a temperature of from 0 to 250° C., an ammonium halide of the amine of the general formula (8) being formed as a byproduct in addition to the silylorganoamine of the general formula (7),
b) addition of a base (B) to the reaction mixture, the base (B) containing at least 2 mol of basic functional groups per mole, double decomposition occurring in which the amine of the general formula (8) is liberated and base (B) is added in an amount such that at least 1.6 mol of the basic functional groups of the base (B) are present as hydrogen halide adduct,
c) distillation of the amine of the general formula (8) out of the reaction mixture,
d) addition of base (B) to the reaction mixture in an amount sufficient to form two liquid phases, one phase containing at least 90% by weight of a hydrohalide of the base (B), and
e) removal of the liquid phase which contains at least 90% by weight of the hydrohalide of the base (B).

19 more elements

Dependencies are inferred from the claim text.

Facts

Application: 13/375,081Filed 1 Jun 2010
Priority: DE 10 2009 026 755.74 Jun 2009
Published: 22 Mar 2012
Term ends: Not estimatedThe source records don’t support an estimate.

Classification4 codes

C07F 7/1892
Preparation; Treatments not provided for in C07F7/20: by reactions not provided for in C07F7/1876 - C07F7/1888
Y02P 20/582
Improvements relating to the production of bulk chemicals: recycling of unreacted starting or intermediate materials
C07F
Acyclic, carbocyclic or heterocyclic compounds containing elements other than carbon, hydrogen, halogen
Y02P
Low-carbon manufacturing