JP2017525689A - 水中でヒドロメチルフルフラールから2,5−フランジカルボン酸を生成するための触媒および方法 - Google Patents
水中でヒドロメチルフルフラールから2,5−フランジカルボン酸を生成するための触媒および方法 Download PDFInfo
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- JP2017525689A JP2017525689A JP2017505641A JP2017505641A JP2017525689A JP 2017525689 A JP2017525689 A JP 2017525689A JP 2017505641 A JP2017505641 A JP 2017505641A JP 2017505641 A JP2017505641 A JP 2017505641A JP 2017525689 A JP2017525689 A JP 2017525689A
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- Prior art keywords
- hmf
- catalyst
- acid
- product
- hydroxymethylfurfural
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- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 108010073771 Soybean Proteins Proteins 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- QYTDEUPAUMOIOP-UHFFFAOYSA-N TEMPO Chemical group CC1(C)CCCC(C)(C)N1[O] QYTDEUPAUMOIOP-UHFFFAOYSA-N 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
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- 241000588902 Zymomonas mobilis Species 0.000 description 1
- YCZZQSFWHFBKMU-UHFFFAOYSA-N [5-(hydroxymethyl)oxolan-2-yl]methanol Chemical compound OCC1CCC(CO)O1 YCZZQSFWHFBKMU-UHFFFAOYSA-N 0.000 description 1
- 241000435299 [Candida] bracarensis Species 0.000 description 1
- 241000985249 [Clostridium] indolis Species 0.000 description 1
- 241001147717 [Clostridium] sphenoides Species 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 1
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 1
- NYENCOMLZDQKNH-UHFFFAOYSA-K bis(trifluoromethylsulfonyloxy)bismuthanyl trifluoromethanesulfonate Chemical compound [Bi+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F NYENCOMLZDQKNH-UHFFFAOYSA-K 0.000 description 1
- ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- CETPSERCERDGAM-UHFFFAOYSA-N ceric oxide Chemical compound O=[Ce]=O CETPSERCERDGAM-UHFFFAOYSA-N 0.000 description 1
- 229910000422 cerium(IV) oxide Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- XBWRJSSJWDOUSJ-UHFFFAOYSA-L chromium(ii) chloride Chemical compound Cl[Cr]Cl XBWRJSSJWDOUSJ-UHFFFAOYSA-L 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
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- 238000010924 continuous production Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
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- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000003810 ethyl acetate extraction Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000002803 fossil fuel Substances 0.000 description 1
- 239000002816 fuel additive Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 229960001545 hydrotalcite Drugs 0.000 description 1
- 229910001701 hydrotalcite Inorganic materials 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000002029 lignocellulosic biomass Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- BAZQYVYVKYOAGO-UHFFFAOYSA-M loxoprofen sodium hydrate Chemical group O.O.[Na+].C1=CC(C(C([O-])=O)C)=CC=C1CC1C(=O)CCC1 BAZQYVYVKYOAGO-UHFFFAOYSA-M 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N methyl monoether Natural products COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000002910 solid waste Substances 0.000 description 1
- 229940001941 soy protein Drugs 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/46—Ruthenium, rhodium, osmium or iridium
- B01J23/462—Ruthenium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/42—Singly bound oxygen atoms
- C07D307/44—Furfuryl alcohol
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
としても知られる、2−ヒドロキシメチル−5−フルフラアルデヒドなどのその他の有用な材料に変換され得ることが、長い間認識されてきた。利用可能なバイオマス炭水化物は、極めて豊富にあるので、HMFをベースにした汎用化学製品および燃料製品の開発に、強力な再生可能資源ベースを提供する。
Claims (8)
- ヒドロキシメチルフルフラールを、2,5−フランジカルボン酸を含むフラン生成物に変換するための方法であって、
ある量のヒドロキシメチルフルフラールを水と、ヒドロキシメチルフルフラールを少なくとも5質量パーセント含有する水溶液を提供する工程と、
前記水溶液を、不均一系ルテニウム系触媒の存在下で、かつヒドロキシメチルフルフラールを2,5−フランジカルボン酸を含むフラン酸化生成物へと酸化するのに有効な条件であり、水以外の、ヒドロキシメチルフルフラールまたは2,5−フランジカルボン酸のためのいかなる溶媒も実質的に存在しない条件下で、酸素源と組み合わせる工程と
を含む、方法。 - 前記触媒が、その単独触媒活性成分としてルテニウムを使用する、請求項1に記載の方法。
- 前記触媒が担持されていない、請求項2に記載の方法。
- 前記触媒が、非担持酸化ルテニウム触媒である、請求項3に記載の方法。
- 前記2,5−フランジカルボン酸が、前記2,5−フランジカルボン酸の実質的に全てが溶液中に残存する温度で、前記不均一系触媒から分離される、請求項1に記載の方法。
- 前記方法を、第1の槽で実施し、次いで、2,5−フランジカルボン酸を、溶液中にある状態で、前記第1の槽から、前記第1の槽内の前記不均一系触媒の少なくともいくらかを伴って第2の槽に移し、前記第1の槽からの移された前記2,5−フランジカルボン酸および触媒を、前記第2の槽内で、前記第2の槽内において2,5−フランジカルボン酸に有効な溶媒であり、前記触媒を実質的に可溶化させない材料と組み合わせ、次いで、前記触媒を、2,5−フランジカルボン酸、水、および添加された溶媒から分離する、請求項1に記載の方法。
- 1種または複数種のヘキソース糖を含む水溶液から、2,5−フランジカルボン酸を作製するための方法であって、
前記水溶液を急速酸触媒脱水に供して、ヒドロキシメチルフルフラールを含む生成混合物を生成する工程であり、前記水溶液が、酸触媒の存在下で周囲温度から摂氏175度超に、15分未満で加熱される、工程と、
必要に応じて、高温の水を、前記急速酸触媒脱水からの前記生成混合物に添加して、水中にヒドロキシメチルフルフラールを5〜30質量パーセント含有する水性酸化供給材を実現する工程と、
前記水性酸化供給材を、不均一系ルテニウム系触媒の存在下で、かつヒドロキシメチルフルフラールを2,5−フランジカルボン酸を含むフラン酸化生成物へと酸化するのに有効な条件であり、水以外の、ヒドロキシメチルフルフラールまたは2,5−フランジカルボン酸のためのいかなる溶媒も実質的に存在しない条件下で、酸素源と組み合わせる工程と
を含む方法。 - 前記急速酸触媒脱水からの前記生成混合物が、いくらかの残存糖を含有し、残存糖が前記生成混合物から分離された後に、前記生成混合物中のヒドロキシメチルフルフラールを酸化させて、2,5−フランジカルボン酸を含むフラン酸化生成物を得る、請求項7に記載の方法。
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US201462038923P | 2014-08-19 | 2014-08-19 | |
US62/038,923 | 2014-08-19 | ||
PCT/US2015/043710 WO2016028488A1 (en) | 2014-08-19 | 2015-08-05 | Catalyst and process for producing 2,5-furandicarboxylic acid from hydromethylfurfural in water |
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JP2017525689A true JP2017525689A (ja) | 2017-09-07 |
JP2017525689A5 JP2017525689A5 (ja) | 2018-08-16 |
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EP (2) | EP3183241B1 (ja) |
JP (1) | JP6695322B2 (ja) |
KR (1) | KR102196777B1 (ja) |
CN (1) | CN106795130B (ja) |
AU (1) | AU2015303871B2 (ja) |
BR (1) | BR112017003159B1 (ja) |
CA (1) | CA2956953C (ja) |
ES (1) | ES2911178T3 (ja) |
HU (1) | HUE058236T2 (ja) |
MX (1) | MX2017002188A (ja) |
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JP2017190316A (ja) * | 2016-04-15 | 2017-10-19 | 三菱ケミカル株式会社 | 2,5−フランジカルボン酸の精製方法 |
CN106008416B (zh) * | 2016-07-04 | 2019-02-19 | 浙江大学 | 一种2,5-呋喃二甲醛的制备方法 |
CN106565647B (zh) * | 2016-10-29 | 2020-01-10 | 华东理工大学 | 一种催化氧化5-羟甲基糠醛制备2,5-呋喃二甲酸的方法 |
EP3498699A1 (en) | 2017-12-13 | 2019-06-19 | Basf Se | Chromatography method for the purification of furfural derivatives |
CN112830915B (zh) * | 2019-11-19 | 2021-11-23 | 中国科学院宁波材料技术与工程研究所 | 一种2,5-呋喃二甲酸的低温制备方法 |
IT201900025096A1 (it) | 2019-12-20 | 2021-06-20 | Novamont Spa | Processo per la sintesi di acido 2,5-furandicarbossilico |
CN113117706B (zh) * | 2019-12-31 | 2024-04-12 | 中国石油化工股份有限公司 | 一种金属改性的钌基催化剂及由其催化制备2,5-呋喃二羧酸的方法 |
CN113117705B (zh) * | 2019-12-31 | 2024-05-07 | 中国石油化工股份有限公司 | 一种改性钌基催化剂及由其催化制备2,5-呋喃二羧酸的方法 |
FR3109778A1 (fr) * | 2020-04-29 | 2021-11-05 | IFP Energies Nouvelles | Procede d’oxydation du 5-hydroxymethylfurfural |
CN116063258A (zh) * | 2021-10-29 | 2023-05-05 | 中国石油化工股份有限公司 | 一种连续生产5-羟甲基糠醛和2,5-呋喃二甲酸的方法 |
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US9957244B2 (en) | 2018-05-01 |
KR102196777B1 (ko) | 2020-12-30 |
EP3183241B1 (en) | 2022-03-16 |
JP6695322B2 (ja) | 2020-05-20 |
CN106795130B (zh) | 2021-01-22 |
AU2015303871A1 (en) | 2017-02-23 |
ES2911178T3 (es) | 2022-05-18 |
KR20170040807A (ko) | 2017-04-13 |
BR112017003159A2 (pt) | 2017-11-28 |
US20170217917A1 (en) | 2017-08-03 |
BR112017003159B1 (pt) | 2021-10-05 |
WO2016028488A1 (en) | 2016-02-25 |
CA2956953A1 (en) | 2016-02-25 |
EP4086243A1 (en) | 2022-11-09 |
CA2956953C (en) | 2021-06-29 |
MX2017002188A (es) | 2017-05-03 |
HUE058236T2 (hu) | 2022-07-28 |
EP3183241A1 (en) | 2017-06-28 |
AU2015303871B2 (en) | 2018-11-29 |
EP3183241A4 (en) | 2018-01-24 |
CN106795130A (zh) | 2017-05-31 |
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