Synthesis and application of alcohol amine with expended main carbon chain

Patent metadata

Field	Value
Publication number	US-11548848-B2
Application number	US-202117401599-A
Country	US
Kind code	B2
Filing date	Aug 13, 2021
Priority date	Jan 28, 2021
Publication date	Jan 10, 2023
Grant date	Jan 10, 2023

Abstract

Synthesis and application of an alcohol amine with an extended main carbon chain are provided, belonging to the field of chemical building materials. Under the action of a catalyst, tertiary amine is subjected to a two-step substitution reaction, a hydrolytic reaction and a reducing reaction to obtain a novel alcohol amine (NAA). The novel alcohol amine as provided may have a better grinding aid effect than triethanolamine while is added into cement as a cement grinding aid, and thus has a wide application prospect.

First claim

What is claimed is:

1. A method for synthesizing a novel alcohol amine (NAA) with an extended main carbon chain, comprising the following steps:
adding a tertiary amine (R—OH) and a catalyst of concentrated sulfuric acid into a reaction vessel to mix uniformly, then adding hydrobromic acid and heating to 80° C.-110° C. for reacting, cooling and distilling to obtain bromoethanolamine after the reacting for 30-60 minutes, wherein a molar ratio of hydrobromic acid to tertiary amine is 1:1;
adding a cyanating agent and the catalyst into the distilled solution, and reacting for 50-80 minutes at a temperature of 110° C.-240° C. to obtain cyanoethanolamine;
after obtaining the cyanoethanolamine, adding an 70%-80% sulfuric acid aqueous solution, heating and hydrolyzing to obtain carboxylolamine; and
adding a reducing agent and refluxing, reducing the carboxylolamine to obtain an alcohol amine with an extended main carbon chain;
the reaction scheme for synthesizing the novel alcohol amine (NAA) with an extended main carbon chain is as follows:

in the reaction scheme, the compound 1 is the tertiary amine (R—OH), the compound 2 is the bromoethanolamine, the compound 3 is the cyanoethanolamine, the compound 4 is the carboxylolamine and the NAA is the novel alcohol amine (NAA) with an extended main carbon chain.

2. The method for synthesizing a novel alcohol amine (NAA) with an extended main carbon chain according to claim 1 , wherein a hydroxyl group in the tertiary amine is substituted with a bromine atom and a cyanide ion in two steps, and then hydrolyzed to generate carboxylic acid, and finally an alcohol amine compound with the extended main carbon chain is obtained through a lithium aluminum tetrahydrogen reduction reaction, that is, the —OH in an original structure reacts to be —CH 2 —OH.

3. The method for synthesizing a novel alcohol amine (NAA) with an extended main carbon chain according to claim 1 , wherein the tertiary amine is one or more selected from the group consisting of triethanolamine, diethanol monoisopropanolamine, ethanol diisopropanolamine and triisopropanolamine.

4. The method for synthesizing a novel alcohol amine (NAA) with an extended main carbon chain according to claim 1 , wherein the cyanating agent is one or two selected from the group consisting of potassium cyanide, sodium cyanide, zinc cyanide and potassium ferrocyanide.

5. The method for synthesizing a novel alcohol amine (NAA) with an extended main carbon chain according to claim 1 , wherein the catalyst is one of N-methylpyrrolidone and dimethylformamide.

6. The method for synthesizing a novel alcohol amine (NAA) with an extended main carbon chain according to claim 1 , wherein a temperature of bromine atom substitution reaction ranges from 85° C. to 105° C.

7. The method for synthesizing a novel alcohol amine (NAA) with an extended main carbon chain according to claim 1 , wherein a temperature of cyanide ion substitution reaction ranges from 150° C. to 200° C., and a time of the cyanide ion substitution reaction lasts for 60-80 minutes.

8. The method for synthesizing a novel alcohol amine (NAA) with an extended main carbon chain according to claim 1 , wherein the reducing agent is lithium tetrahydroaluminum.

Assignees

• Univ Beijing Technology

Inventors

• Wang Jianfeng
• Song Yan
• Lan Mingzhang
• Cui Suping
• Wang Yan
• Chang Lei
• Wang Yali
• Ma Xiaoyu

Classifications

• C07C213/08 Primary

  by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups · CPC title

• C04B24/122

  Hydroxy amines · CPC title

• C07C213/10

  Separation; Purification; Stabilisation; Use of additives · CPC title

• B01J27/02

  Sulfur, selenium or tellurium; Compounds thereof · CPC title

• C07C213/00 Primary

  Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton · CPC title