KR-102841320-B9 - METHOD FOR PREPARING AMINOALKOXYSILANE COMPOUNDS

Abstract

One embodiment of the present specification provides a method for preparing an aminoalkoxysilane compound, comprising: (a) preparing a mixture comprising a chloroalkylalkoxysilane, an amine compound, and a metal halide; and (b) reacting the mixture.

Inventors

• 조대준
• 권민성
• 이대형
• 성기현
• 윤형호

Assignees

• 금호석유화학 주식회사

Dates

Publication Date

20260513

Application Date

20220906

Claims (12)

1. (a) a step of preparing a mixture comprising a compound represented by the following chemical formula 1, an amine compound represented by the following chemical formula 2, a metal halide represented by the following chemical formula 3, and a base; and (b) a step of reacting the above mixture; comprising a method for preparing an aminoalkoxysilane compound: [Chemical Formula 1] Cl-(R 1 )-Si(R 2 ) m (OR 3 ) 3-m In the above chemical formula 1, R1 is a C1 – C4 alkylene group, R2 is a C1 – C2 alkyl group, R3 is a C1 – C4 alkyl group, and m is 0, 1, or 2; [Chemical Formula 2] NH(R 4 ) p [(R 5 )-Si(R 6 ) n (OR 7 ) 3-n ] 2-p In the above chemical formula 2, R4 is hydrogen, a C1 – C16 alkyl group or a C1 – C12 heteroalkyl group, R5 is a C1 – C4 alkylene group, R6 is a C1 – C2 alkyl group, R7 is a C1 – C4 alkyl group, n is 0, 1, or 2, and p is 0, 1, or 2; [Chemical Formula 3] MX In the above chemical formula 3, M is an alkali metal and X is a halogen element.
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6. In paragraph 1, A method for preparing an aminoalkoxysilane compound, wherein the content of the compound represented by Chemical Formula 1 included in the above mixture is 1.1 to 10 moles per mole of the amine compound.
7. In paragraph 1, A method for preparing an aminoalkoxysilane compound, wherein the content of the metal halide included in the mixture is 0.01 to 5 moles per mole of the amine compound.
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9. In paragraph 1, A method for preparing an aminoalkoxysilane compound, wherein the base is one selected from the group consisting of triethylamine (TEA), N,N-diisopropylethylamine (DIEA), 1,1,3,3-tetramethylguanidine (TMG), and combinations of two or more of these.
10. In paragraph 1, A method for preparing an aminoalkoxysilane compound, wherein step (b) above is performed at 60 to 200°C.
11. In paragraph 1, A method for preparing an aminoalkoxysilane compound, wherein step (b) above is performed for 1 to 50 hours.
12. In paragraph 1, A method for preparing an aminoalkoxysilane compound, wherein step (b) above is performed under a pressure of 0.1 to 10 bar.

Description

Method for Preparing Aminoalkoxysilane Compounds This specification relates to a method for manufacturing aminoalkoxysilane compounds. Aminoalkoxysilanes are representative compounds used as terminal modifiers in the manufacture of rubber compositions for tire treads. Aminoalkoxysilane compounds are bonded to the ends of conjugated diene polymers to improve compatibility with fillers, and ultimately play a role in improving the wetting resistance and rolling resistance of the tire. Conventionally, aminoalkoxysilane compounds have been prepared using rare metals such as palladium, rhodium, and platinum as catalysts. However, the reductive amination reaction using palladium has a low yield and poses a fire hazard. The reductive elimination reaction using rhodium catalyst has the disadvantages of a low yield and high catalyst costs. Additionally, while the hydrosilylation reaction using platinum as a catalyst has been reported to allow for catalyst reuse, it has a low yield. Furthermore, during the hydrosilylation reaction of the allyl position, alpha and beta position selection results in the formation of a mixture as the final product, which requires an additional process for purification. There is an SN2 reaction between an amine and a halogen that does not use a catalyst, but this method has also been reported to have a low yield of less than 2%, and since it uses liquid ammonia, a high-pressure reaction is essential. Another method for synthesizing aminoalkoxysilanes is the reaction of a primary amine with a chloroalkylalkoxysilane, which is known to have a high yield of 90%, but has the problem of requiring a considerably long reaction time of 4 days. Therefore, there is an increasing demand for a process for producing aminoalkoxysilane compounds that exhibits high selectivity and yield, while having a short reaction time and improved safety. Hereinafter, one aspect of the present specification will be described with reference to the attached drawings. However, the details described in the present specification may be implemented in various different forms and are therefore not limited to the embodiments described herein. Furthermore, in order to clearly explain one aspect of the present specification in the drawings, parts unrelated to the explanation have been omitted, and similar parts throughout the specification have been given similar reference numerals. Throughout the specification, when it is stated that a part is "connected" to another part, this includes not only cases where they are "directly connected," but also cases where they are "indirectly connected" with other members interposed between them. Furthermore, when it is stated that a part "includes" a certain component, this means that, unless specifically stated otherwise, it does not exclude other components but rather allows for the inclusion of additional components. When a range of numerical values is described in this specification, unless a specific range is otherwise described, the value has the precision of significant figures provided according to the standard rules in chemistry for significant figures. For example, 10 includes a range of 5.0 to 14.9, and the number 10.0 includes a range of 9.50 to 10.49. As used in this specification, the term "alkyl group" means a linear or branched hydrocarbon group “C n H 2n+1 -”. Examples include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl. As used in this specification, the term "heteroalkyl group" means an alkyl group in which one or more carbon atoms are substituted with heteroatoms. As used in this specification, the term “heteroatom” refers to all atoms excluding carbon and hydrogen, such as, but not limited to, oxygen, nitrogen, sulfur, phosphorus, and halogen atoms. As used in this specification, the term "alkylene group" means a linear or branched hydrocarbon group "-C n H 2n -" having two valencies. Examples include, but are not limited to, methylene groups (-CH 2 -), ethylene groups (-CH 2 -CH 2 -). As used in this specification, the term “C x ~C y ” means having x to y carbon atoms. For example, “alkyl group of C x ~C y ” means an alkyl group having x to y carbon atoms. Hereinafter, one embodiment of the present specification will be described in detail. Method for preparing aminoalkoxysilane compounds A method for preparing an aminoalkoxysilane compound according to one aspect of the present specification comprises: (a) preparing a mixture comprising a chloroalkylalkoxysilane, an amine compound, and a metal halide; and (b) reacting the mixture. Step (a) above is a step of mixing starting materials for synthesizing an aminoalkoxysilane compound, and by using a metal halide as an additive along with a chloroalkylalkoxysilane and an amine compound, the reaction time can be shortened while high selectivity and yield can be obtained. The above chloroalkylalkoxysilane may be a compound represented by the following chemical formula 1. [Chemical Formula 1] Cl-(R 1 )-S