RU2015139512A - Способ получения HMF из сахара с пониженным образованием побочных продуктов и композиции HMF с улучшенной стабильностью - Google Patents
Способ получения HMF из сахара с пониженным образованием побочных продуктов и композиции HMF с улучшенной стабильностью Download PDFInfo
- Publication number
- RU2015139512A RU2015139512A RU2015139512A RU2015139512A RU2015139512A RU 2015139512 A RU2015139512 A RU 2015139512A RU 2015139512 A RU2015139512 A RU 2015139512A RU 2015139512 A RU2015139512 A RU 2015139512A RU 2015139512 A RU2015139512 A RU 2015139512A
- Authority
- RU
- Russia
- Prior art keywords
- hydroxymethylfurfural
- hmf
- composition
- improved stability
- antioxidants
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims 3
- 230000015572 biosynthetic process Effects 0.000 title 1
- 239000006227 byproduct Substances 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- NOEGNKMFWQHSLB-UHFFFAOYSA-N 5-hydroxymethylfurfural Chemical compound OCC1=CC=C(C=O)O1 NOEGNKMFWQHSLB-UHFFFAOYSA-N 0.000 claims 8
- RJGBSYZFOCAGQY-UHFFFAOYSA-N hydroxymethylfurfural Natural products COC1=CC=C(C=O)O1 RJGBSYZFOCAGQY-UHFFFAOYSA-N 0.000 claims 7
- 238000000034 method Methods 0.000 claims 7
- 239000003963 antioxidant agent Substances 0.000 claims 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- 230000018044 dehydration Effects 0.000 claims 3
- 238000006297 dehydration reaction Methods 0.000 claims 3
- 239000001301 oxygen Substances 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 239000004255 Butylated hydroxyanisole Substances 0.000 claims 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 2
- 239000007864 aqueous solution Substances 0.000 claims 2
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 claims 2
- 229940043253 butylated hydroxyanisole Drugs 0.000 claims 2
- 235000019282 butylated hydroxyanisole Nutrition 0.000 claims 2
- 230000015556 catabolic process Effects 0.000 claims 2
- 238000006731 degradation reaction Methods 0.000 claims 2
- 150000002402 hexoses Chemical class 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000001569 carbon dioxide Substances 0.000 claims 1
- 229910002092 carbon dioxide Inorganic materials 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- -1 ester derivative of hydroxymethyl furfural Chemical class 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 239000011261 inert gas Substances 0.000 claims 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
- A61K31/341—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide not condensed with another ring, e.g. ranitidine, furosemide, bufetolol, muscarine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/08—Solutions
-
- 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
- C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
-
- 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
- C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
- C07D307/48—Furfural
-
- 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
- C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
- C07D307/48—Furfural
- C07D307/50—Preparation from natural products
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/06—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
- Furan Compounds (AREA)
- Cosmetics (AREA)
- Saccharide Compounds (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Claims (9)
1. Способ получения гидроксиметилфурфурола из водного раствора, содержащего одну или несколько гексоз, включающий дегидратацию водного раствора гексозы путем воздействия кислотой в среде с пониженным содержанием кислорода.
2. Способ по п. 1, где сложноэфирное или эфирное производное гидроксиметилфурфурола получают путем проведения дегидратации в присутствии спирта или карбоновой кислоты, соответственно.
3. Способ по любому из пп. 1 или 2, где из пространства над веществом в реакторе, в котором происходит дегидратация, кислород вытесняют путем пропускания другого, инертного газа.
4. Способ по п. 3, включающий пропускание азота или диоксида углерода через реактор.
5. Способ улучшения устойчивости гидроксиметилфурфурола или производного гидроксиметилфурфурола к деградации, включающий добавление одного или нескольких антиоксидантов.
6. Способ по п. 5, где в один или несколько антиоксидантов входит бутилированный гидроксианизол.
7. Композиция гидроксиметилфурфурола с улучшенной стабильностью, содержащая гидроксиметилфурфурол с одним или несколькими антиоксидантами.
8. Композиция по п. 7, содержащая гидроксиметилфурфурол и бутилированный гидроксианизол.
9. Способ улучшения устойчивости хранящегося гидроксиметилфурфурола к деградации до его применения, включающий хранение гидроксиметилфурфурола в среде с пониженным содержанием кислорода.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361782539P | 2013-03-14 | 2013-03-14 | |
| US61/782,539 | 2013-03-14 | ||
| PCT/US2014/018186 WO2014158554A1 (en) | 2013-03-14 | 2014-02-25 | Process for making hmf from sugars with reduced byproduct formation, and improved stability hmf compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2015139512A true RU2015139512A (ru) | 2017-04-19 |
| RU2659166C2 RU2659166C2 (ru) | 2018-06-28 |
Family
ID=51625021
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2015139512A RU2659166C2 (ru) | 2013-03-14 | 2014-02-25 | Способ получения HMF из сахаров с пониженным образованием побочных продуктов и композиции HMF с улучшенной стабильностью |
Country Status (11)
| Country | Link |
|---|---|
| US (3) | US9422257B2 (ru) |
| EP (1) | EP2968255B1 (ru) |
| JP (1) | JP6373350B2 (ru) |
| KR (1) | KR102001716B1 (ru) |
| CN (1) | CN105007913B (ru) |
| AU (1) | AU2014242130B2 (ru) |
| BR (1) | BR112015022816A2 (ru) |
| CA (3) | CA3079120C (ru) |
| MX (1) | MX354363B (ru) |
| RU (1) | RU2659166C2 (ru) |
| WO (1) | WO2014158554A1 (ru) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2755417T3 (es) * | 2017-05-08 | 2020-04-22 | Avalon Ind Ag | Procedimiento para estabilizar 5-hidroximetilfurfural (HMF) |
| DE102018208507A1 (de) | 2018-05-29 | 2019-12-05 | Südzucker AG | Anolytfraktion-katalysierte HMF-Herstellung |
| DE102018208510A1 (de) | 2018-05-29 | 2019-12-05 | Südzucker AG | Salz- und Säuregemisch-katalysierte HMF-Herstellung |
| CN112334453A (zh) * | 2018-06-18 | 2021-02-05 | 阿彻丹尼尔斯米德兰德公司 | 用于形成基于生物的聚合物的单体和其他反应物的颜色稳定 |
| CN116178314A (zh) * | 2021-11-29 | 2023-05-30 | 中国科学院宁波材料技术与工程研究所 | 一种提高5-羟甲基糠醛储运稳定性的方法 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2917520A (en) * | 1957-09-11 | 1959-12-15 | Arthur C Cope | Production and recovery of furans |
| EP0105672B1 (en) * | 1982-09-28 | 1986-04-09 | The Procter & Gamble Company | Synthesis of sulphonated organic compounds |
| CN1038422A (zh) * | 1988-06-10 | 1990-01-03 | 爱德华·A·德朗 | 使用解离的木质纤维材料进行模塑的方法及其产品 |
| JPH0399072A (ja) * | 1989-09-11 | 1991-04-24 | Kao Corp | ５―ヒドロキシメチル―２―フランカルボキシアルデヒドの製法 |
| EP2050742B1 (en) * | 2006-03-10 | 2010-07-07 | Furanix Technologies B.V | Use of an organic acid esters of 5-hydroxymethylfurfural |
| EP1834950A1 (en) * | 2006-03-10 | 2007-09-19 | Avantium International B.V. | Method for the synthesis of 5-alkoxymethylfurfural ethers and their use |
| AT503385B1 (de) * | 2006-03-20 | 2008-05-15 | C Y L Pharmazeutika Gmbh | Mittel zur behandlung von oxidativem stress |
| UA97690C2 (ru) * | 2007-09-07 | 2012-03-12 | Фураникс Технолоджиз Б.В. | Способ получения смеси простых 5-гидроксиметилфурфуралевых эфиров и содержащее их топливо или топливная композиция |
| WO2009030507A2 (en) * | 2007-09-07 | 2009-03-12 | Furanix Technologies B.V. | Hydroxymethylfurfural ethers from sugars and higher alcohols |
| MX2010006504A (es) * | 2007-12-12 | 2010-08-31 | Archer Daniels Midland Co | Conversion de carbohidratos a hidroxi-metilfurfural (hmf) y derivado. |
| EP2556061A1 (en) * | 2010-04-07 | 2013-02-13 | Novozymes A/S | A method of producing hydroxymethylfurfural |
| CN102453007A (zh) * | 2010-10-22 | 2012-05-16 | 王天任 | 一种制备5-羟甲基糠醛的方法 |
| JP5779888B2 (ja) * | 2011-01-19 | 2015-09-16 | 三菱化学株式会社 | ２−フルアルデヒド化合物の製造方法 |
| JP2012232961A (ja) * | 2011-05-09 | 2012-11-29 | Osaka Prefecture Univ | 温度応答性複合ポリマー |
| FR2975396B1 (fr) * | 2011-05-16 | 2013-12-27 | Centre Nat Rech Scient | Procede de preparation de 5-hydroxymethylfurfural |
| CN103183653A (zh) * | 2011-12-29 | 2013-07-03 | 广西科学院 | 一种制备5-羟甲基糠醛的绿色方法 |
-
2014
- 2014-02-25 US US14/771,842 patent/US9422257B2/en active Active
- 2014-02-25 CN CN201480009838.5A patent/CN105007913B/zh active Active
- 2014-02-25 MX MX2015011794A patent/MX354363B/es active IP Right Grant
- 2014-02-25 CA CA3079120A patent/CA3079120C/en active Active
- 2014-02-25 AU AU2014242130A patent/AU2014242130B2/en active Active
- 2014-02-25 KR KR1020157028531A patent/KR102001716B1/ko active IP Right Grant
- 2014-02-25 WO PCT/US2014/018186 patent/WO2014158554A1/en active Application Filing
- 2014-02-25 CA CA2902632A patent/CA2902632C/en active Active
- 2014-02-25 EP EP14773375.2A patent/EP2968255B1/en active Active
- 2014-02-25 BR BR112015022816A patent/BR112015022816A2/pt not_active Application Discontinuation
- 2014-02-25 CA CA3080500A patent/CA3080500C/en active Active
- 2014-02-25 RU RU2015139512A patent/RU2659166C2/ru active
- 2014-02-25 JP JP2016500372A patent/JP6373350B2/ja active Active
-
2016
- 2016-07-19 US US15/213,514 patent/US9604951B2/en active Active
-
2017
- 2017-02-09 US US15/428,288 patent/US9776980B1/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CA3079120C (en) | 2020-09-08 |
| CA3079120A1 (en) | 2014-10-02 |
| AU2014242130B2 (en) | 2017-07-27 |
| US20160009675A1 (en) | 2016-01-14 |
| WO2014158554A1 (en) | 2014-10-02 |
| KR102001716B1 (ko) | 2019-07-18 |
| EP2968255A1 (en) | 2016-01-20 |
| AU2014242130A1 (en) | 2015-08-27 |
| CA3080500C (en) | 2020-09-08 |
| MX354363B (es) | 2018-02-27 |
| JP2016517407A (ja) | 2016-06-16 |
| CA2902632C (en) | 2020-06-30 |
| MX2015011794A (es) | 2016-01-08 |
| CN105007913B (zh) | 2017-09-29 |
| BR112015022816A2 (pt) | 2017-07-18 |
| KR20150132299A (ko) | 2015-11-25 |
| US9422257B2 (en) | 2016-08-23 |
| CA2902632A1 (en) | 2014-10-02 |
| CN105007913A (zh) | 2015-10-28 |
| RU2659166C2 (ru) | 2018-06-28 |
| WO2014158554A8 (en) | 2015-10-15 |
| US9776980B1 (en) | 2017-10-03 |
| US20160332978A1 (en) | 2016-11-17 |
| EP2968255A4 (en) | 2016-07-27 |
| EP2968255B1 (en) | 2018-12-05 |
| CA3080500A1 (en) | 2014-10-02 |
| US9604951B2 (en) | 2017-03-28 |
| JP6373350B2 (ja) | 2018-08-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2015139512A (ru) | Способ получения HMF из сахара с пониженным образованием побочных продуктов и композиции HMF с улучшенной стабильностью | |
| MX338371B (es) | Metodo para la preparacion de acido 2,5-furandicarboxilico y para la preparacion del dialquilester de acido 2,5-furandicarboxilico. | |
| RU2015139511A (ru) | Способ получения 2,5-фурандикарбоновой кислоты | |
| WO2014199306A3 (de) | Verfahren zur herstellung von 5-hydroxymethylfurfural (hmf) | |
| MY159836A (en) | Method for the preparation of 2,5-furandicarboxylic acid and esters thereof | |
| WO2009030512A3 (en) | Hydroxymethylfurfural ethers and esters prepared in ionic liquids | |
| WO2010132740A3 (en) | Oxidation of furfural compounds | |
| MY184015A (en) | Utilizing a multiphase reactor for the conversion of biomass to produce substituted furans | |
| MX2015007903A (es) | Esterificacion del acido 2,5-furandicarboxilico. | |
| EA201491190A1 (ru) | Способ получения hmf и производных hmf из сахаров с восстановлением непревращенных сахаров, подходящих для прямой ферментации до этанола | |
| EA201491189A1 (ru) | Способ получения левулиновой кислоты | |
| SI3157910T1 (en) | SELECTIVE OXIDATION PROCEDURE 5-HYDROXYMETYLFURFURAL | |
| JP2014528927A5 (ru) | ||
| MX2017014760A (es) | Proceso de síntesis biomimética de compositos de polianilina y su uso en la fabricación de supercapacitores. | |
| JP2017525689A5 (ru) | ||
| WO2015083843A3 (en) | Dihomo-gamma-linolenic acid-containing microbial oil and dihomo-gamma-linolenic acid-containing microbial biomass | |
| RU2012151152A (ru) | Твердая композиция терефталевой кислоты | |
| RU2014137472A (ru) | Дегидратирование содержащего воду источника формальдегида и способ получения сложного эфира этилен-ненасыщенной карбоновой кислоты | |
| WO2011055051A3 (fr) | Glutaraldehyde bioressource et ses procedes de fabrication | |
| RU2015140786A (ru) | Способ получения состава с гербицидной активностью | |
| JP2015500313A5 (ru) | ||
| EP3725783A3 (en) | Process for the production of furfural using a water-immiscible organic solvent | |
| TH130019B (th) | วิธีการสำหรับการเตรียมของกรด 2,5-ฟูแรนไดคาร์บอกซิลิคและสำหรับการเตรียม ไดแอลคิลเอสเทอร์ของกรด 2,5-ฟูแรนไดคาร์บอกซิลิค | |
| EA201400480A1 (ru) | Очищающая композиция | |
| TH130019A (th) | วิธีการสำหรับการเตรียมของกรด2,5-ฟูแรนไดคาร์บอกซิลิคและสำหรับการเตรียมไดแอลคิล |