Energy efficient manufacturing process for preparing N,O-triglycidyl aminophenols
원문보기
IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
C07D-301/24
C07D-303/36
출원번호
US-0310033
(2014-05-15)
등록번호
US-10023548
(2018-07-17)
국제출원번호
PCT/TH2014/000024
(2014-05-15)
국제공개번호
WO2015/174936
(2015-11-19)
발명자
/ 주소
Dubey Pradip, Kumar
Khullar, Alok
Nayawat, Thipa
Visatsingh, Kamonsun
Samuthsen, Patcharin
Samant, Prashant
출원인 / 주소
Aditya Birla Chemicals (Thailand) Ltd.
대리인 / 주소
Kim Winston LLP
인용정보
피인용 횟수 :
0인용 특허 :
3
초록▼
The invention relates to an improved process for making monomeric triglycidyl compounds, wherein the triglycidyl compounds include N, O-triglycidyl compounds containing at least one primary aromatic amine and one phenolic functional group attached to the same or a different aromatic ring. The method
The invention relates to an improved process for making monomeric triglycidyl compounds, wherein the triglycidyl compounds include N, O-triglycidyl compounds containing at least one primary aromatic amine and one phenolic functional group attached to the same or a different aromatic ring. The methods of the present invention result in the production of N, O-triglycidyl compounds, such as those of formula I and II. The improved process is energy efficient, environment friendly, and results in increased yields of product. The methods of the present invention can be performed in the absence of protic organic co-solvents during the reaction of an epihalohydrin with an aminophenol, such as compounds of formula II and IV, which provides an intermediate halohydrin compound. The methods of the present invention may also be performed in the absence of a phase transfer catalyst.
대표청구항▼
1. A method for producing a triglycidyl aminophenol from at least one aminophenol and at least one epihalohydrin, comprising the steps of: (i) reacting at least one aminophenol with at least one epihalohydrin in the presence of a polar solvent present in an amount in the range of from 20% to 70% by
1. A method for producing a triglycidyl aminophenol from at least one aminophenol and at least one epihalohydrin, comprising the steps of: (i) reacting at least one aminophenol with at least one epihalohydrin in the presence of a polar solvent present in an amount in the range of from 20% to 70% by weight based on the weight of the at least one aminophenol and in the absence of an organic solvent to produce a halohydrin compound in a reaction mixture;(ii) reacting the halohydrin compound in the reaction mixture with at least one alkali metal hydroxide in the absence of a co-catalyst to form the triglycidyl aminophenol;(iii) removing unreacted epihalohydrin from the reaction mixture;(iv) adding an organic solvent and an aqueous solvent to the reaction mixture to form an organic layer and an aqueous layer;(v) isolating the organic layer;(vi) washing the organic layer with water;(vii) isolating the organic layer by removing the water by phase separation; and(viii) recovering the organic solvent from the organic layer to provide the triglycidyl aminophenol:wherein the triglycidyl aminophenol is at least one compound formula I and formula II: wherein:R and R′ are each independently selected from the group consisting of hydrogen, C1-C6 alkyl, phenyl, cyclohexyl and cyclopentyl; andR1, R2, R3, and R4 are each independently selected from the group consisting of hydrogen, halogen, and C1-C6 alkyl;mixtures thereof and salts thereof:wherein the aminophenol is at least one compound of formula III and formula IV: wherein:R and R′ are each independently selected from the group consisting of hydrogen, C1-C6 alkyl, phenyl, cyclohexyl and cyclopentyl; andR1, R2, R3, and R4 are each independently selected from the group consisting of hydrogen, halogen, and C1-C6 alkyl;mixtures thereof and salts thereof, and wherein the polar solvent is water. 2. The method of claim 1, wherein the epihalohydrin is at least one compound of formula V: wherein: R′ is hydrogen; andX is selected from the group consisting of chlorine and bromine; and mixtures thereof. 3. The method of claim 1, wherein step (iii) further comprises removing the polar solvent. 4. The method of claim 1, wherein the organic solvent of step (iv) is isolated and recycled without any additional purification. 5. The method of claim 1, wherein in step (iii), the epihalohydrin is free of hydrolyzed byproducts. 6. The method of claim 1, wherein in step (iii), the epihalohydrin is removed from the reaction mixture by distillation. 7. The method of claim 1, wherein in step (viii), the organic solvent is recovered from the organic layer by distillation. 8. The method of claim 1, wherein in step (vi), the organic layer is washed once with water. 9. The method of claim 1, wherein in step (vi), the amount of water used for washing the organic layer is between about 0.5 mol to about 5 mol per mole of the at least one aminophenol. 10. The method of claim 1, wherein the organic solvent is selected from the group consisting of an aromatic hydrocarbon and a cyclic fatty hydrocarbon. 11. The method of claim 1, wherein the organic solvent is toluene or m-xylene. 12. The method of claim 1, wherein steps (i)-(viii) are carried out in a batch process. 13. The method of claim 12, wherein at least a portion of the organic solvent recovered in step (viii) is used in step (iv) of a subsequent batch process. 14. The method of claim 12, wherein at least a portion of the epichlorohydrin removed in step (iii) is used in step (i) of a subsequent batch process. 15. The method of claim 1, wherein the amount of at least one epihalohydrin is about 3 to about 5 moles per active hydrogen of the at least one aminophenol. 16. The method of claim 1, wherein, in step (iii), the unreacted epihalohydrin is removed under reduced pressure. 17. The method of claim 16, wherein the epihalohydrin is removed at a temperature below 90° C. 18. The method of claim 1, wherein the chemical oxygen demand (COD) of the polar solvent is less than about 10,000 ppm. 19. The method of claim 1, wherein the triglycidyl aminophenol is produced in a yield greater than about 98%. 20. The method of claim 1, wherein the triglycidyl aminophenol has a hydrolysable halogen content less than about 400 ppm.
연구과제 타임라인
LOADING...
LOADING...
LOADING...
LOADING...
LOADING...
이 특허에 인용된 특허 (3)
Dobinson, Bryan; Thoseby, Michael R., Preparation of N-glycidyl compounds.
※ AI-Helper는 부적절한 답변을 할 수 있습니다.