[미국특허]
Synthesis of paracetamol (acetaminophen) from biomass-derived p-hydroxybenzamide
원문보기
IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
C07C-213/02
C07C-231/10
B23P-019/04
B60L-011/18
H01M-008/10
H01M-016/00
H01M-008/04858(2016.01)
B60K-003/02
B60K-015/03
G05D-023/19
출원번호
15914597
(2018-03-07)
등록번호
10286504
(2019-05-14)
발명자
/ 주소
Ralph, John
Karlen, Steven
Mobley, Justin
출원인 / 주소
Wisconsin Alumni Research Foundation
대리인 / 주소
Leone, Esq., Joseph T.
인용정보
피인용 횟수 :
0인용 특허 :
0
초록
Disclosed is a method to make N-acetyl-p-aminophenol. The method includes steps for converting biomass-derived p-hydroxybenzoates to p-hydroxybenzamide, then to p-aminophenol; and then N-acetylating the p-aminophenol.
대표청구항▼
1. A method to make N-acetyl-p-aminophenol, the method comprising: (a) converting p-hydroxybenzamide to p-aminophenol; and then(b) N-acetylating at least a portion of the p-aminophenol to yield N-acetyl-p-aminophenol. 2. The method of claim 1, wherein, step (a) comprises contacting the p-hydroxybenz
1. A method to make N-acetyl-p-aminophenol, the method comprising: (a) converting p-hydroxybenzamide to p-aminophenol; and then(b) N-acetylating at least a portion of the p-aminophenol to yield N-acetyl-p-aminophenol. 2. The method of claim 1, wherein, step (a) comprises contacting the p-hydroxybenzamide with a hypohalite salt to cause a Hofmann-style rearrangement reaction, thereby yielding p-aminophenol. 3. The method of claim 1, wherein step (b) comprises contacting the p-aminophenol with acetic anhydride and water for a time and at a temperature to yield N-acetyl-p-aminophenol. 4. The method of claim 1, wherein, step (a) comprises contacting the p-hydroxybenzamide with a hypohalite salt to cause a Hofmann-style rearrangement reaction, thereby yielding p-aminophenol; and step (b) comprises contacting the p-aminophenol with acetic anhydride and water for a time and at a temperature to yield N-acetyl-p-aminophenol. 5. The method of claim 4, wherein step (a) is conducted in an alkaline aqueous or non-aqueous solvent, at a pH from about 10 to about 14, a temperature from about 20° C. to about 100° C., and for a time of from about 30 minutes to about 24 h. 6. The method of claim 4, wherein step (b) is conducted at a temperature of from about 100° C. to about 150° C. 7. The method of claim 4, wherein step (a) is conducted in an alkaline aqueous or non-aqueous solvent, at a pH from about 10 to about 14, a temperature from about 20° C. to about 100° C., and for a time of from about 30 minutes to about 24 h; and step (b) is conducted at a temperature of from about 100° C. to about 150° C. 8. A method to make N-acetyl-p-aminophenol, the method comprising: (a) providing p-hydroxybenzamide derived from p-hydroxybenzoate esters derived from biomass;(b) converting at least a portion of the p-hydroxybenzamide to p-aminophenol; and then(c) N-acetylating at least a portion of the p-aminophenol to yield N-acetyl-p-aminophenol. 9. The method of claim 8, wherein, step (b) comprises contacting the p-hydroxybenzamide with a hypohalite salt to cause a Hofmann-style rearrangement reaction, thereby yielding p-aminophenol. 10. The method of claim 8, wherein step (c) comprises contacting the p-aminophenol with acetic anhydride and water for a time and at a temperature to yield N-acetyl-p-aminophenol. 11. The method of claim 8, wherein, step (b) comprises contacting the p-hydroxybenzamide with a hypohalite salt to cause a Hofmann-style rearrangement reaction, thereby yielding p-aminophenol; and step (c) comprises contacting the p-aminophenol with acetic anhydride and water for a time and at a temperature to yield N-acetyl-p-aminophenol. 12. The method of claim 11, wherein step (b) is conducted in an alkaline aqueous or non-aqueous solvent, at a pH from about 10 to about 14, a temperature from about 20° C. to about 100° C., and for a time of from about 30 minutes to about 24 h. 13. The method of claim 11, wherein step (c) is conducted at a temperature of from about 100° C. to about 150° C. 14. The method of claim 11, wherein step (b) is conducted in an alkaline aqueous or non-aqueous solvent, at a pH from about 10 to about 14, a temperature from about 20° C. to about 100° C., and for a time of from about 30 minutes to about 24 h; and step (c) is conducted at a temperature of from about 100° C. to about 150° C. 15. A method to make N-acetyl-p-aminophenol from lignin, the method comprising: (a) performing an ammonia fiber expansion process reaction or an extractive ammonia process reaction on lignin to yield p-hydroxybenzamide;(b) converting at least a portion of the p-hydroxybenzamide from step (a) to p-aminophenol; and then(c) N-acetylating at least a portion of the p-aminophenol from step (b) to yield N-acetyl-p-aminophenol. 16. The method of claim 15, wherein, step (b) comprises contacting the p-hydroxybenzamide with a hypohalite salt to cause a Hofmann-style rearrangement reaction, thereby yielding p-aminophenol. 17. The method of claim 15, wherein step (c) comprises contacting the p-aminophenol with acetic anhydride and water for a time and at a temperature to yield N-acetyl-p-aminophenol. 18. The method of claim 15, wherein, step (b) comprises contacting the p-hydroxybenzamide with a hypohalite salt to cause a Hofmann-style rearrangement reaction, thereby yielding p-aminophenol; and step (c) comprises contacting the p-aminophenol with acetic anhydride and water for a time and at a temperature to yield N-acetyl-p-aminophenol. 19. The method of claim 18, wherein step (b) is conducted in an alkaline aqueous or non-aqueous solvent, at a pH from about 10 to about 14, a temperature from about 20° C. to about 100° C., and for a time of from about 30 minutes to about 24 h. 20. The method of claim 18, wherein step (c) is conducted at a temperature of from about 100° C. to about 150° C. 21. The method of claim 18, wherein step (b) is conducted in an alkaline aqueous or non-aqueous solvent, at a pH from about 10 to about 14, a temperature from about 20° C. to about 100° C., and for a time of from about 30 minutes to about 24 h; and step (c) is conducted at a temperature of from about 100° C. to about 150° C.
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