IPC분류정보
국가/구분 |
United States(US) Patent
등록
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국제특허분류(IPC7판) |
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출원번호 |
US-0932111
(2013-07-01)
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등록번호 |
US-8703986
(2014-04-22)
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발명자
/ 주소 |
- Lee, Yu-Chin
- Liao, Jen-Hai
- Lo, Sung-Chen
- Wu, Chu-Chun
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출원인 / 주소 |
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대리인 / 주소 |
Fishman & Associates, LLC.
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인용정보 |
피인용 횟수 :
0 인용 특허 :
2 |
초록
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Provided is a process for preparing 10-chloro-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO-C) compound, the process having steps of: reacting a liquid chlorinating agent and 9,10-dihydro-10-hydroxy-9-oxa 10-phosphaphenanthrene 10-oxide compound represented by formula (B) to form a mixtur
Provided is a process for preparing 10-chloro-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO-C) compound, the process having steps of: reacting a liquid chlorinating agent and 9,10-dihydro-10-hydroxy-9-oxa 10-phosphaphenanthrene 10-oxide compound represented by formula (B) to form a mixture, the mixture comprises DOPO-C compound represented by formula (A) and an unreacted liquid chlorinating agent, separating the DOPO-C compound and the unreacted liquid chlorinating agent from the mixture to obtain the DOPO-C compound; wherein X1, X2, and X3 are each independently selected from the group consisting of hydrogen atom, hydroxyl group, cyano group, sulfonic acid group, sulfonate ester group represented by —SO3R1, halogen atom, alkoxy group represented by —OR2, acyclic hydrocarbon group having 1 to 8 carbon atoms, cyclic alkyl group having 3 to 8 carbon atoms, aryl group, heteroaryl group, and arylalkyl group, wherein R1 and R2 are each an acyclic hydrocarbon group having 1 to 8 carbon atoms.
대표청구항
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1. A process for preparing 10-chloro-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO-C) compound, the process comprising steps of: reacting a liquid chlorinating agent and 9,10-dihydro-10-hydroxy-9-oxa 10-phosphaphenanthrene 10-oxide (DOPO-OH) compound represented by formula (B) to form a m
1. A process for preparing 10-chloro-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO-C) compound, the process comprising steps of: reacting a liquid chlorinating agent and 9,10-dihydro-10-hydroxy-9-oxa 10-phosphaphenanthrene 10-oxide (DOPO-OH) compound represented by formula (B) to form a mixture, wherein the mixture comprises DOPO-C compound represented by formula (A) and an unreacted liquid chlorinating agent, separating the DOPO-C compound represented by formula (A) and the unreacted liquid chlorinating agent from the mixture to obtain the DOPO-C compound represented by formula (A); wherein the variables X1, X2, and X3 are each independently selected from the group consisting of hydrogen atom, hydroxyl group, cyano group, sulfonic acid group, sulfonate ester group represented by —SO3R1, halogen atom, alkoxy group represented by —OR2, acyclic hydrocarbon group having 1 to 8 carbon atoms, cyclic alkyl group having 3 to 8 carbon atoms, aryl group, heteroaryl group, and arylalkyl group, wherein R1 and R2 are each independently an acyclic hydrocarbon group having 1 to 8 carbon atoms. 2. The process according to claim 1, wherein the liquid chlorinating agent is selected from the group consisting of thionyl chloride (SOCl2), phosphorus oxychloride (POCl3), phosphorus trichloride, (PCl3), oxalyl chloride ((COCl)2), and a combination thereof. 3. The process according to claim 1, after the step of separating the DOPO-C compound represented by formula (A) and the unreacted liquid chlorinating agent from the mixture to obtain the DOPO-C compound represented by formula (A), the process comprises a step of re-purifying the DOPO-C compound represented by formula (A). 4. The process according to claim 1, wherein the step of reacting a liquid chlorinating agent and DOPO-OH compound to form a mixture includes reacting the liquid chlorinating agent and the DOPO-OH compound to form the mixture at a temperature ranging from 50° C. to 130° C. 5. The process according to claim 1, wherein an equivalent of the liquid chlorinating agent is at least 1/Y when the equivalent of the DOPO-OH compound is 1, wherein Y represents an equivalent of chlorine of the liquid chlorinating agent that react with one equivalent of the DOPO-OH compound. 6. The process according to claim 5, wherein the equivalent of the liquid chlorinating agent ranges from 1/Y to 10 when the equivalent of the DOPO-OH compound is 1. 7. The process according to claim 1, before the step of reacting a liquid chlorinating agent and DOPO-OH compound to form a mixture, the process comprises the steps of: reacting water and 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO) compound to form an aqueous solution, wherein the DOPO compound is represented by formula (C); adding a metal-free oxidant into the aqueous solution to obtain a mixed solution, wherein the mixed solution comprises the DOPO-OH compound represented by formula (B); andseparating the DOPO-OH compound represented by formula (B) from the mixed solution, so as to obtain the DOPO-OH compound; wherein the variables X1, X2, and X3 are each independently selected from the group consisting of hydrogen atom, hydroxyl group, cyano group, sulfonic acid group, sulfonate ester group represented by —SO3R1, halogen atom, alkoxy group represented by —OR2, acyclic hydrocarbon group having 1 to 8 carbon atoms, cyclic alkyl group having 1 to 8 carbon atoms, aryl group, heteroaryl group, and arylalkyl group, wherein R1 and R2 are each independently an acyclic hydrocarbon group having 1 to 8 carbon atoms. 8. The process according to claim 7, before the step of reacting water and DOPO compound to form an aqueous solution, the process comprises steps of: providing the DOPO compound; and heating the DOPO compound to a temperature ranging from 100° C. to 180° C. to render the DOPO compound in liquid form. 9. The process according to claim 7, wherein the step of reacting water and DOPO compound to form an aqueous solution includes reacting water and the DOPO compound to form an aqueous solution at a temperature ranging from 90° C. to 110° C. 10. The process according to claim 7, wherein the step of adding a metal-free oxidant into the aqueous solution to obtain a mixed solution includes adding a metal-free oxidant into the aqueous solution to obtain a mixed solution at a temperature ranging from 90° C. to 110° C. 11. The process according to claim 7, wherein the liquid chlorinating agent is thionyl chloride. 12. The process according to claim 7, wherein the metal-free oxidant is selected from the group consisting of hydrogen peroxide, oxygen, ozone, halogen, hypochloric acid, chloric acid, perchloric acid, peracetic acid, and a combination thereof. 13. The process according to claim 12, wherein the metal-free oxidant is hydrogen peroxide. 14. The process according to claim 2, before the step of reacting a liquid chlorinating agent and DOPO-OH compound to form a mixture, the process comprises the steps of: reacting water and 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO) compound to form an aqueous solution, wherein the DOPO compound is represented by formula (C); adding a metal-free oxidant into the aqueous solution to obtain a mixed solution, wherein the metal-free oxidant is free from metal element and the mixed solution comprises the DOPO-OH compound represented by formula (B); andseparating the DOPO-OH compound represented by formula (B) from the mixed solution, so as to obtain the DOPO-OH compound; wherein the variables X1, X2, and X3 are each independently selected from the group consisting of hydrogen atom, hydroxyl group, cyano group, sulfonic acid group, sulfonate ester group represented by —SO3R1, halogen atom, alkoxy group represented by —OR2, acyclic hydrocarbon group having 1 to 8 carbon atoms, cyclic alkyl group having 3 to 8 carbon atoms, aryl group, heteroaryl group, and arylalkyl group, wherein R1 and R2 are each independently an acyclic hydrocarbon group having 1 to 8 carbon atoms. 15. The process according to claim 3, wherein before the step of reacting a liquid chlorinating agent and DOPO-OH compound to form a mixture, the process comprises the steps of: reacting water and 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO) compound to form an aqueous solution, wherein the DOPO compound is represented by formula (C); adding a metal-free oxidant into the aqueous solution, so as to obtain a mixed solution, wherein the metal-free oxidant is free from metal element and the mixed solution comprises the DOPO-OH compound represented by formula (B); andseparating the DOPO-OH compound represented by formula (B) from the mixed solution, so as to obtain the DOPO-OH compound; wherein the variables X1, X2, and X3 are each independently selected from the group consisting of hydrogen atom, hydroxyl group, cyano group, sulfonic acid group, sulfonate ester group represented by —SO3R1, halogen atom, alkoxy group represented by —OR2, acyclic hydrocarbon group having 1 to 8 carbon atoms, cyclic alkyl group having 3 to 8 carbon atoms, aryl group, heteroaryl group, and arylalkyl group, wherein R1 and R2 are each independently an acyclic hydrocarbon group having 1 to 8 carbon atoms. 16. The process according to claim 4, wherein before the step of reacting a liquid chlorinating agent and DOPO-OH compound to form a mixture, the process comprises the steps of: reacting water and 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO) compound to form an aqueous solution, wherein the DOPO compound is represented by formula (C); adding a metal-free oxidant into the aqueous solution, so as to obtain a mixed solution, wherein the metal-free oxidant is free from metal element and the mixed solution comprises the DOPO-OH compound represented by formula (B); andseparating the DOPO-OH compound represented by formula (B) from the mixed solution, so as to obtain the DOPO-OH compound; wherein the variables X1, X2, and X3 are each independently selected from the group consisting of hydrogen atom, hydroxyl group, cyano group, sulfonic acid group, sulfonate ester group represented by —SO3R1, halogen atom, alkoxy group represented by —OR2, acyclic hydrocarbon group having 1 to 8 carbon atoms, cyclic alkyl group having 3 to 8 carbon atoms, aryl group, heteroaryl group, and arylalkyl group, wherein R1 and R2 are each independently an acyclic hydrocarbon group having 1 to 8 carbon atoms. 17. The process according to claim 5, before the step of reacting a liquid chlorinating agent and DOPO-OH compound to form a mixture, the process comprises the steps of: reacting water and 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO) compound to form an aqueous solution, wherein the DOPO compound is represented by formula (C); adding a metal-free oxidant into the aqueous solution, so as to obtain a mixed solution, wherein the metal-free oxidant is free from metal element and the mixed solution comprises the DOPO-OH compound represented by formula (B); andseparating the DOPO-OH compound represented by formula (B) from the mixed solution, so as to obtain the DOPO-OH compound; wherein the variables X1, X2, and X3 are each independently selected from the group consisting of hydrogen atom, hydroxyl group, cyano group, sulfonic acid group, sulfonate ester group represented by —SO3R1, halogen atom, alkoxy group represented by —OR2, acyclic hydrocarbon group having 1 to 8 carbon atoms, cyclic alkyl group having 3 to 8 carbon atoms, aryl group, heteroaryl group, and arylalkyl group, wherein R1 and R2 are each independently an acyclic hydrocarbon group having 1 to 8 carbon atoms. 18. The process according to claim 6, before the step of reacting a liquid chlorinating agent and DOPO-OH compound to form a mixture, the process comprises the steps of: reacting water and 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO) compound to form an aqueous solution, wherein the DOPO compound is represented by formula (C); adding a metal-free oxidant into the aqueous solution, so as to obtain a mixed solution, wherein the metal-free oxidant is free from metal element and the mixed solution comprises the DOPO-OH compound represented by formula (B); andseparating the DOPO-OH compound represented by formula (B) from the mixed solution, so as to obtain the DOPO-OH compound; wherein the variables X1, X2, and X3 are each independently selected from the group consisting of hydrogen atom, hydroxyl group, cyano group, sulfonic acid group, sulfonate ester group represented by —SO3R1, halogen atom, alkoxy group represented by —OR2, acyclic hydrocarbon group having 1 to 8 carbon atoms, cyclic alkyl group having 3 to 8 carbon atoms, aryl group, heteroaryl group, and arylalkyl group, wherein R1 and R2 are each independently an acyclic hydrocarbon group having 1 to 8 carbon atoms. 19. The process according to claim 18, before the step of reacting water and DOPO compound to form an aqueous solution, the process comprises steps of: providing the DOPO compound; and heating the DOPO compound to a temperature ranging from 100° C. to 180° C. to render the DOPO compound in liquid form. 20. The process according to claim 18, wherein the step of reacting water and DOPO compound to form an aqueous solution includes reacting water and the DOPO compound to form an aqueous solution at a temperature ranging from 90° C. to 110° C.
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