Mannich base, production and use thereof

Patent metadata

Field	Value
Publication number	US-9587198-B2
Application number	US-201314397335-A
Country	US
Kind code	B2
Filing date	Apr 25, 2013
Priority date	Apr 26, 2012
Publication date	Mar 7, 2017
Grant date	Mar 7, 2017

Abstract

This invention relates to a Mannich base, production and use thereof in producing a detergent. The Mannich base is represented by the following formula (III), wherein A and R 2 are as defined in the specification. The Mannich base can be used to produce a detergent and a fuel oil composition exhibiting excellent deposit formation suppressing performance and excellent anticorrosion performance.

First claim

The invention claimed is:

1. A Mannich base, comprising the structure unit (I) and the structure unit (II):

wherein, multiple R 1 may be the same as or different from one another, each independently selected from the group consisting of hydrogen, a C 1-4 linear or branched alkyl and a single bond; multiple R′ may be the same as or different from one another, each independently selected from the group consisting of hydrogen and a C 1-6 linear or branched alkyl; R 2 represents a C 1-12 linear or branched alkyl; R 3 represents a C 1-6 linear or branched alkyl; R 4 represents a hydrocarbyl having a number-averaged molecular weight Mn of 300-3000; multiple y may be the same as or different from one another, each independently selected from an integer of from 2 to 5.

2. The Mannich base according to claim 1 , represented by the following formula (III):

wherein, multiple A may be the same as or different from one another, each independently selected from the group consisting of

and hydrogen, with the proviso that at least one A represents

multiple R′ may be the same as or different from one another, each independently selected from the group consisting of hydrogen and a C 1-6 linear or branched alkyl; multiple R a may be the same as or different from one another, each independently selected from the group consisting of hydrogen, a C 1-4 linear or branched alkyl and

with the proviso that at least one R a represents

multiple R b may be the same as or different from one another, each independently selected from the group consisting of hydrogen,

and a C 1-4 linear or branched alkyl, with the proviso that at least one R b represents

R 2 represents a C 1-12 linear or branched alkyl; R 3 represents a C 1-6 linear or branched alkyl; R 4 represents a hydrocarbyl having a number-averaged molecular weight Mn of 300-3000; multiple y may be the same as or different from one another, each independently selected from an integer of from 2 to 5; multiple c may be the same as or different from one another, each independently selected from an integer of from 0 to 10.

3. A process for producing a Mannich base comprising the step of reacting a phenolic compound of the formula (V), a phenolic compound of the formula (VI), a polyalkylenepolyamine of the formula (VII) and a C 1 -C 7 linear or branched saturated aliphatic aldehyde to conduct a Mannich reaction,

wherein, R 2 represents a C 1-12 linear or branched alkyl; R 3 represents a C 1-6 linear or branched alkyl; R 4 represents a hydrocarbyl having a number-averaged molecular weight Mn of 300-3000; multiple R b ′ may be the same as or different from one another, each independently selected from the group consisting of hydrogen and a C 1-4 linear or branched alkyl, with the proviso that at least two of R b ′ are hydrogen; y represents an integer of from 2 to 5; c′ represents an integer of from 1 to 11.

4. The process for producing a Mannich base according to claim 3 , which is conducted in line with any one of the following ways:
Way (1) comprising the following steps:
the first step: reacting the phenolic compound of the formula (VI), the polyalkylenepolyamine of the formula (VII) and the C 1 -C 7 linear or branched saturated aliphatic aldehyde at a reaction temperature of 50 to 200 degrees centigrade to conduct a Mannich reaction, to produce an intermediate; and
the second step: reacting the intermediate, the phenolic compound of the formula (V) and the C 1 -C 7 linear or branched saturated aliphatic aldehyde at a reaction temperature of 40 to 200 degrees centigrade to conduct a Mannich reaction, so as to produce the Mannich base,
or
Way (2) comprising the following steps:
the first step: reacting the phenolic compound of the formula (V), the polyalkylenepolyamine of the formula (VII) and the C 1 -C 7 linear or branched saturated aliphatic aldehyde at a reaction temperature of 40 to 200 degrees centigrade to conduct a Mannich reaction, to produce an intermediate; and
the second step: reacting the intermediate, the phenolic compound of the formula (VI) and the C 1 -C 7 linear or branched saturated aliphatic aldehyde at a reaction temperature of 50 to 200 degrees centigrade to conduct a Mannich reaction, so as to produce the Mannich base,
or
Way (3) comprising the step of reacting the phenolic compound of the formula (V), the phenolic compound of the formula (VI), the polyalkylenepolyamine of the formula (VII) and the C 1 -C 7 linear or branched saturated aliphatic aldehyde at a reaction temperature of 40 to 200 degrees centigrade to conduct a Mannich reaction to produce the Mannich base.

5. The process for producing a Mannich base according to claim 4 , wherein in the first step of Way (1), the ratio by molar between the phenolic compound of the formula (VI), the polyalkylenepolyamine of the formula (VII) and the C 1 -C 7 linear or branched saturated aliphatic aldehyde is 1:0.3-3:0.3-3.5; in the second step of Way (1), the ratio by molar between the intermediate, the phenolic compound of the formula (V) and the C 1 -C 7 linear or branched saturated aliphatic aldehyde is 1:0.2-1.5:0.2-2; in the first step of Way (2), the ratio by molar between the phenolic compound of the formula (V), the polyalkylenepolyamine of the formula (VII) and the C 1 -C 7 linear or branched saturated aliphatic aldehyde is 1:1.5-2.5:1.5-3; in the second step of Way (2), the ratio by molar between the intermediate, the phenolic compound of the formula (VI) and the C 1 -C 7 linear or branched saturated aliphatic aldehyde is 1:1.5-3:1.5-3; in Way (3), the ratio by molar between the phenolic compound of the formula (V), the phenolic compound of the formula (VI), the polyalkylenepolyamine of the formula (VII) and the C 1 -C 7 linear or branched saturated aliphatic aldehyde is 1:1-5:1-3:2-8.

6. The process for producing a Mannich base according to claim 3 , wherein the Mannich reaction is conducted in the presence of one or more diluent selected from the group consisting of polyolefins, mineral base oils and polyethers.

7. The process for producing a Mannich base according to claim 3 , wherein the phenolic compound of the formula (VI) is produced by in the presence of an alkylating catalyst, reacting a phenolic compound of the formula (IV) with a polyolefin having a number-averaged molecular weight Mn of 300-3000 to conduct an alkylation reaction,

wherein, R 3 is as defined in claim 3 .

8. A detergent comprising the Mannich base according to claim 1 or a Mannich base produced in line with the process according to claim 3 , and one or more diluent selected from the group consisting of polyolefins, mineral base oils and polyethers.

Assignees

• China Petroleum & Chem Corp
• Res Inst Petroleum Processing Sinopec

Inventors

• Xin Shihao
• Duan Qinghua
• Huang Zuoxin

Classifications

• C10L2250/04

  Additive or component is a polymer · CPC title

• C07C215/50 Primary

  with amino groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain · CPC title

• C10M159/16

  obtained by Mannich reactions · CPC title

• C11D3/3723

  Polyamines or polyalkyleneimines · CPC title

• C10M2217/043

  Mannich bases · CPC title