WO2020165882A3 - 고순도 2-피론-4,6-디카르복실산 제조방법 및 그를 위한 중간체 제조방법 - Google Patents

고순도 2-피론-4,6-디카르복실산 제조방법 및 그를 위한 중간체 제조방법 Download PDF

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WO2020165882A3
WO2020165882A3 PCT/IB2020/051457 IB2020051457W WO2020165882A3 WO 2020165882 A3 WO2020165882 A3 WO 2020165882A3 IB 2020051457 W IB2020051457 W IB 2020051457W WO 2020165882 A3 WO2020165882 A3 WO 2020165882A3
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tpa
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WO2020165882A2 (ko
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차현길
주정찬
김희택
김경안
박제영
강명종
황성연
오동엽
이민우
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한국화학연구원
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Priority claimed from KR1020190109179A external-priority patent/KR102267703B1/ko
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Priority to EP20756552.4A priority Critical patent/EP3909947A4/en
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Abstract

본 발명은 고순도 2-피론-4,6-디카르복실산 제조방법 및 그를 위한 중간체 제조방법으로; 1) PET로부터 TPA를 제조하는 단계; 2) TPA를 재조합 균주와 반응시켜 PDC를 생성하는 단계; 및 3) 제조된 PDC를 고순도로 정제하는 단계를 포함한다. 본 발명에 의한 바이오 매스 유래 SiO2 촉매, 그 제조방법, 및 이를 이용한 PET의 TPA 분해방법을 이용하면, 종래의 중성 조건하에서 PET 가수분해 속도 보다 빠른 시간에 고순도 테레프탈 산(TPA)의 제조가 가능하며, 제조된 테레프탈 산은 다시 폴리에스테르 섬유의 원료 등으로 유용하게 사용할 수 있다. 본 발명은 TphB 효소, TphAabc 효소, LigAB 효소 및 LigC 효소를 코딩하는 뉴클레오티드 서열이 도입된, 2-피론-4,6-디카복실산(PDC) 생산용 재조합 균주 및 상기 PDC 생산용 재조합 균주와 기질을 반응시키는 단계를 포함하는 PDC의 생산방법에 관한 것이다. 본 발명은 공업적으로 제조되거나 상업적으로 입수가능한 조질(crude) 2-피론-4,6-디카르복실산 또는 이의 소듐염에서, NMR 및/또는 TLC 분석법으로 확인되지만 제거 및 정제가 곤란한 불순물을, 아세톤을 첨가하여 석출시켜 제거하고, 결과된 용액을 유기용매로 추출 및 농축하고, 결과된 농축물을 컬럼 크로마토그래피에서 에틸아세테이트와 헥산의 혼합용매로 용리함으로써, 2-피론-4,6-디카르복실산을 고순도로 정제하는 방법을 제공한다.
PCT/IB2020/051457 2019-02-12 2020-02-21 고순도 2-피론-4,6-디카르복실산 제조방법 및 그를 위한 중간체 제조방법 WO2020165882A2 (ko)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP20756552.4A EP3909947A4 (en) 2019-02-12 2020-02-21 METHOD FOR PRODUCING HIGH PURITY 2-PYRONE-4,6-DICARBOXYLIC ACID AND METHOD FOR PRODUCING AN INTERMEDIATE THEREOF

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
KR10-2019-0016016 2019-02-12
KR1020190016016A KR102278269B1 (ko) 2019-02-12 2019-02-12 PET의 TPA 분해용 바이오 매스 유래 SiO₂ 촉매, 그 제조방법, 및 이를 이용한 PET의 TPA 분해방법
KR10-2019-0074404 2019-06-21
KR1020190074404A KR20200145980A (ko) 2019-06-21 2019-06-21 2-파이론-4,6-디카복실산 생산용 재조합 균주 및 이를 이용한 2-파이론-4,6-디카복실산 생산 방법
KR10-2019-0109179 2019-09-03
KR1020190109179A KR102267703B1 (ko) 2019-09-03 2019-09-03 2-피론-4,6-디카르복실산의 정제 방법

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WO2020165882A3 true WO2020165882A3 (ko) 2021-05-06
WO2020165882A4 WO2020165882A4 (ko) 2021-06-24

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005278549A (ja) * 2004-03-30 2005-10-13 Yoshihiro Katayama 2−ピロン−4,6−ジカルボン酸を発酵生産するための遺伝子、前記遺伝子を含むプラスミド、前記プラスミドを含む形質転換体及び2−ピロン−4,6−ジカルボン酸の製造方法
KR101157373B1 (ko) * 2011-05-12 2012-06-21 충남대학교산학협력단 왕겨 유래 고순도 다공성 실리카 및 실리콘 합성 방법
US9394549B2 (en) * 2012-01-27 2016-07-19 Genaris, Inc. Method for producing useful chemical substance from terephthalic acid potassium salt
KR20180019699A (ko) * 2015-06-19 2018-02-26 차이나 페트로리움 앤드 케미컬 코포레이션 방향족 탄화수소, 파라크실렌 및 테레프탈산의 제조 방법

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4882063B2 (ja) * 2005-10-12 2012-02-22 国立大学法人東京農工大学 テレフタル酸の代謝に関与する新規遺伝子
JP2007211188A (ja) * 2006-02-10 2007-08-23 Univ Of Tokushima ポリエステルの分解方法および芳香族ジカルボン酸の回収方法
ITUB20150924A1 (it) * 2015-05-29 2016-11-29 N A M Nano Analysis & Mat S R L Processo sol-gel per la produzione di aerogeli di silice

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005278549A (ja) * 2004-03-30 2005-10-13 Yoshihiro Katayama 2−ピロン−4,6−ジカルボン酸を発酵生産するための遺伝子、前記遺伝子を含むプラスミド、前記プラスミドを含む形質転換体及び2−ピロン−4,6−ジカルボン酸の製造方法
KR101157373B1 (ko) * 2011-05-12 2012-06-21 충남대학교산학협력단 왕겨 유래 고순도 다공성 실리카 및 실리콘 합성 방법
US9394549B2 (en) * 2012-01-27 2016-07-19 Genaris, Inc. Method for producing useful chemical substance from terephthalic acid potassium salt
KR20180019699A (ko) * 2015-06-19 2018-02-26 차이나 페트로리움 앤드 케미컬 코포레이션 방향족 탄화수소, 파라크실렌 및 테레프탈산의 제조 방법

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
MICHINOBU TSUYOSHI, HISHIDA MASAKIYO, SATO MASAE, KATAYAMA YOSHIHIRO, MASAI EIJI, NAKAMURA MASAYA, OTSUKA YUICHIRO, OHARA SEIJI, S: "Polyexters of 2-Pryone-4,6-Dicarboxylic Acid (PDC) Obtai ned from a Metabolic Intermediate of Lignin.", POLYMER JOURNAL, vol. 40, no. 1, pages 68 - 75, XP009527770, DOI: 10.1295/polymj.PJ2007158 *

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