JP2012523442A5 - - Google Patents
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- Publication number
- JP2012523442A5 JP2012523442A5 JP2012505116A JP2012505116A JP2012523442A5 JP 2012523442 A5 JP2012523442 A5 JP 2012523442A5 JP 2012505116 A JP2012505116 A JP 2012505116A JP 2012505116 A JP2012505116 A JP 2012505116A JP 2012523442 A5 JP2012523442 A5 JP 2012523442A5
- Authority
- JP
- Japan
- Prior art keywords
- pla
- lactic acid
- solvent
- lactate
- process according
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000000034 method Methods 0.000 claims description 37
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 21
- 238000006460 hydrolysis reaction Methods 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 13
- 230000007062 hydrolysis Effects 0.000 claims description 11
- 235000014655 lactic acid Nutrition 0.000 claims description 10
- 239000004310 lactic acid Substances 0.000 claims description 8
- 229920000642 polymer Polymers 0.000 claims description 7
- 229920002959 polymer blend Polymers 0.000 claims description 7
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 4
- 238000004064 recycling Methods 0.000 claims description 4
- 239000000178 monomer Substances 0.000 claims description 3
- 238000000605 extraction Methods 0.000 claims description 2
- -1 lactate ester Chemical class 0.000 claims 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 6
- 230000003197 catalytic effect Effects 0.000 claims 6
- 239000003054 catalyst Substances 0.000 claims 5
- 150000003903 lactic acid esters Chemical class 0.000 claims 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims 4
- 238000004090 dissolution Methods 0.000 claims 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims 2
- 230000002378 acidificating effect Effects 0.000 claims 2
- 238000009835 boiling Methods 0.000 claims 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 241000287462 Phalacrocorax carbo Species 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 238000000066 reactive distillation Methods 0.000 claims 1
- 238000000746 purification Methods 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE2009/0232 | 2009-04-14 | ||
| BE2009/0232A BE1018716A3 (fr) | 2009-04-14 | 2009-04-14 | Recyclage chimique du pla par hydrolyse. |
| PCT/EP2010/054274 WO2010118954A1 (fr) | 2009-04-14 | 2010-03-31 | Recyclage chimique du pla par hydrolyse |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012523442A JP2012523442A (ja) | 2012-10-04 |
| JP2012523442A5 true JP2012523442A5 (https=) | 2014-02-13 |
| JP5770162B2 JP5770162B2 (ja) | 2015-08-26 |
Family
ID=41010584
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012505116A Active JP5770162B2 (ja) | 2009-04-14 | 2010-03-31 | 加水分解によるｐｌａのケミカルリサイクル |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8431683B2 (https=) |
| EP (1) | EP2419395B8 (https=) |
| JP (1) | JP5770162B2 (https=) |
| KR (1) | KR101706798B1 (https=) |
| CN (1) | CN102348673B (https=) |
| AU (1) | AU2010237248A1 (https=) |
| BE (1) | BE1018716A3 (https=) |
| BR (1) | BRPI1013327B1 (https=) |
| MX (1) | MX2011010716A (https=) |
| WO (1) | WO2010118954A1 (https=) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE1019608A3 (fr) * | 2009-04-14 | 2012-09-04 | Galactic Sa | Recyclage chimique du pla par alcoolyse. |
| BE1018850A3 (fr) * | 2009-08-06 | 2011-10-04 | Galactic Sa | Purification d'un flux de polymere conventionnel contamine par du pla. |
| BE1018882A3 (fr) * | 2009-09-10 | 2011-10-04 | Galactic Sa | Procede de recyclage stereospecifique d'un melange de polymeres a base de pla. |
| ES2981179T3 (es) | 2011-08-19 | 2024-10-07 | Uhde Inventa Fischer Gmbh | Procedimiento y dispositivo para la recuperación de lactida de polilactida o glicolida de poliglicolida |
| EP2725019B1 (de) | 2012-10-26 | 2015-04-08 | Uhde Inventa-Fischer GmbH | Verfahren zur Herstellung cyclischer Diester, insbesondere Dilactid |
| CN102976922B (zh) * | 2012-10-30 | 2015-07-15 | 青岛科技大学 | 一种废聚乳酸材料水解回收乳酸钙的新方法 |
| WO2014086840A1 (de) | 2012-12-04 | 2014-06-12 | Uhde Inventa-Fischer Gmbh | Verfahren zur selektiven chemischen extraktion von milchsäure aus polymerblends |
| DE102013210110A1 (de) | 2013-05-29 | 2014-12-04 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Verfahren zur Anreicherung von Polylactid aus Polylactid-haltigem Abfall, angereichertes Polylactid-Recyclat und Verwendung hiervon |
| US9181412B2 (en) * | 2014-01-20 | 2015-11-10 | Bioplast, Llc | Composition for the degradation of plastic |
| WO2015112098A1 (en) | 2014-01-23 | 2015-07-30 | Ptt Public Company Limited | Process for manufacturing lactide from plastics having polylactic acid |
| PL229904B1 (pl) | 2015-01-08 | 2018-09-28 | Wroclawskie Centrum Badan Eit Spolka Z Ograniczona Odpowiedzialnoscia | Sposób otrzymywania estrów kwasu mlekowego i mleczanomlekowego w reakcji alkoholizy poliestru alifatycznego |
| KR101981391B1 (ko) * | 2017-03-15 | 2019-05-23 | 씨제이제일제당 (주) | 알킬 락테이트의 제조 방법 |
| US10259768B2 (en) * | 2017-05-24 | 2019-04-16 | Board Of Trustees Of Michigan State University | Method of recycling a polyester |
| WO2019219210A1 (de) | 2018-05-18 | 2019-11-21 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Verfahren zur herstellung eines intramolekularen diesters einer hydroxycarbonsäure sowie verfahren zur herstellung einer polyhydroxycarbonsäure |
| CN109761798B (zh) * | 2018-12-24 | 2021-12-17 | 深圳光华伟业股份有限公司 | 乳酸盐的制备方法 |
| BE1027631B1 (fr) | 2020-01-21 | 2021-04-30 | Noosa | Procede de recyclage de textiles contenant de l'acide polylactique |
| MX2022010137A (es) * | 2020-02-19 | 2022-11-10 | Triplew Ltd | Metodos y sistemas para la produccion de acido lactico y el reciclaje del acido polilactico. |
| DE102020205094A1 (de) * | 2020-04-22 | 2021-10-28 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung eingetragener Verein | Additivzusammensetzung sowie deren Verwendung, Kondensationspolymerzusammensetzung, Formmasse und hieraus hergestellte Formmassen und Formteile und deren Verwendung |
| CN112062667A (zh) * | 2020-08-24 | 2020-12-11 | 青岛科技大学 | 一种6-羟基己酸的制备方法 |
| TWI755879B (zh) * | 2020-09-30 | 2022-02-21 | 行政院原子能委員會核能研究所 | 新穎的回收生質塑膠再聚方法 |
| BE1028899B1 (nl) | 2020-12-15 | 2022-07-19 | Despriet Gebroeders Nv | Systeem voor de recyclage van polymelkzuur in afvalstromen om lactide te verkrijgen |
| BE1028893B1 (nl) | 2020-12-15 | 2022-07-19 | Despriet Gebroeders Nv | Recyclageproces voor polymelkzuur in afvalstromen om lactide te verkrijgen |
| BE1029038B1 (fr) | 2021-01-21 | 2022-08-22 | Noosa | Procede de preparation d'acide polylactique au depart d'acide lactique provenant du recyclage de rouleaux supports de bobines de fil ou film et rouleaux supports destines a cet effet |
| BE1029323B1 (fr) | 2021-04-20 | 2022-11-21 | Noosa | Système d'identification de fibres textiles d'acide polylactique |
| NL2028900B1 (en) | 2021-08-02 | 2023-02-17 | Arapaha B V | A method of closed loop recycling of polylactic acid |
| CN115991645B (zh) * | 2021-10-19 | 2025-11-25 | 中国石油化工股份有限公司 | 一种精制环状酯废液的回收处理方法、回收处理系统以及应用 |
| WO2023126480A1 (fr) * | 2021-12-29 | 2023-07-06 | Noosa | Procede pour isoler les fibres a base de d'acide polylactique hors d'un melange de fibres textiles et recuperation de ces dernieres ne contenant plus d'acide polylactique |
| BE1030134B1 (fr) * | 2021-12-29 | 2023-07-31 | Noosa | Procede pour isoler les fibres a base d'acide polylactique hors d'un melange de fibres textiles et recuperation de ces dernieres ne contenant plus d'acide polylactique |
| BE1030133B1 (fr) * | 2021-12-29 | 2023-07-31 | Noosa | Procede pour ameliorer le rendement du recyclage chimique de fibres d’acide polylactique et a conserver leurs proprietes physiques |
| CN114409529A (zh) * | 2022-01-30 | 2022-04-29 | 安徽丰原发酵技术工程研究有限公司 | 一种从乳酸聚合物中回收乳酸的方法 |
| CN114736117A (zh) * | 2022-04-01 | 2022-07-12 | 温州邦鹿化工有限公司 | 一种聚乳酸pla残液高压水解回收工艺 |
| GB2632622A (en) * | 2023-04-25 | 2025-02-19 | Rusty Design Ltd | Biodegradable composite article and method of recycling |
| TW202544153A (zh) * | 2024-02-15 | 2025-11-16 | 荷蘭商道達爾能源科碧恩私人有限公司 | 用於再循環pla之方法 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU8283391A (en) * | 1990-07-13 | 1992-02-04 | E.I. Du Pont De Nemours And Company | High yield recycle process for lactide |
| US5229528A (en) * | 1991-11-22 | 1993-07-20 | E. I. Du Pont De Nemours And Company | Rapid depolymerization of polyhydroxy acids |
| US5264614A (en) | 1991-11-22 | 1993-11-23 | E. I. Du Pont De Nemours And Company | Recovery of polyhydroxy acids |
| US5264617A (en) | 1991-11-22 | 1993-11-23 | E. I. Du Pont De Nemours And Company | Preparation of alkyl esters by depolymerization |
| EP0628533A1 (en) * | 1993-06-07 | 1994-12-14 | E.I. Du Pont De Nemours And Company | Recovery of hydroxy acids from trash |
| JP2003300926A (ja) * | 2002-04-08 | 2003-10-21 | Nippon Shokubai Co Ltd | α−ヒドロキシカルボン酸又はα−オキソカルボン酸の製造方法 |
| CN100475808C (zh) * | 2004-04-30 | 2009-04-08 | 国立大学法人九州工业大学 | 从聚乳酸或其衍生物回收交酯的方法 |
| JP2005330211A (ja) * | 2004-05-19 | 2005-12-02 | Toyohashi Univ Of Technology | 生分解性ポリエステルのモノマー化方法、及び生分解性ポリエステルの処理装置 |
| CN1284779C (zh) * | 2004-07-13 | 2006-11-15 | 武汉大学 | 一种连续制造丙交酯的方法 |
| JP4486561B2 (ja) * | 2005-07-26 | 2010-06-23 | 帝人ファイバー株式会社 | ポリ乳酸ステレオコンプレックスポリマーから異素材を除去する方法 |
| JP2007224113A (ja) * | 2006-02-22 | 2007-09-06 | Teijin Fibers Ltd | 生分解性ポリエステル回収物からの有効成分回収方法 |
| JP4747366B2 (ja) * | 2006-04-06 | 2011-08-17 | 系介 赤松 | プラスチック廃棄物の分別回収方法 |
| JP2008050351A (ja) * | 2006-07-27 | 2008-03-06 | Victor Co Of Japan Ltd | 乳酸の回収方法 |
| US20110160480A1 (en) | 2008-07-30 | 2011-06-30 | Galactic Sa | Continuous Process for Obtaining a Lactic Ester |
| BE1017951A3 (fr) | 2008-07-30 | 2010-01-12 | Galactic Sa | Procede continu d'obtention d'un ester lactique. |
-
2009
- 2009-04-14 BE BE2009/0232A patent/BE1018716A3/fr not_active IP Right Cessation
-
2010
- 2010-03-31 BR BRPI1013327-5A patent/BRPI1013327B1/pt active IP Right Grant
- 2010-03-31 AU AU2010237248A patent/AU2010237248A1/en not_active Abandoned
- 2010-03-31 CN CN201080011067.5A patent/CN102348673B/zh active Active
- 2010-03-31 US US13/263,198 patent/US8431683B2/en active Active
- 2010-03-31 EP EP20100713610 patent/EP2419395B8/fr active Active
- 2010-03-31 WO PCT/EP2010/054274 patent/WO2010118954A1/fr not_active Ceased
- 2010-03-31 MX MX2011010716A patent/MX2011010716A/es not_active Application Discontinuation
- 2010-03-31 JP JP2012505116A patent/JP5770162B2/ja active Active
- 2010-03-31 KR KR1020117026698A patent/KR101706798B1/ko active Active
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