HU185421B - Process and apparatus for producing furfurol from plant materials - Google Patents
Process and apparatus for producing furfurol from plant materials Download PDFInfo
- Publication number
- HU185421B HU185421B HU811146A HU114681A HU185421B HU 185421 B HU185421 B HU 185421B HU 811146 A HU811146 A HU 811146A HU 114681 A HU114681 A HU 114681A HU 185421 B HU185421 B HU 185421B
- Authority
- HU
- Hungary
- Prior art keywords
- reactor
- furfural
- acid
- steam
- hydrolysis
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 77
- 239000000463 material Substances 0.000 title claims abstract description 67
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 title description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 claims abstract description 241
- 239000002253 acid Substances 0.000 claims abstract description 93
- 150000002972 pentoses Chemical class 0.000 claims abstract description 64
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 52
- 230000007062 hydrolysis Effects 0.000 claims abstract description 51
- 238000004519 manufacturing process Methods 0.000 claims abstract description 14
- 230000018044 dehydration Effects 0.000 claims abstract description 13
- 238000006297 dehydration reaction Methods 0.000 claims abstract description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 70
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 41
- 238000004821 distillation Methods 0.000 claims description 18
- 238000003860 storage Methods 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 235000000346 sugar Nutrition 0.000 claims description 14
- 150000008163 sugars Chemical class 0.000 claims description 14
- 230000002378 acidificating effect Effects 0.000 claims description 10
- 229920002678 cellulose Polymers 0.000 claims description 10
- 239000001913 cellulose Substances 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 238000000354 decomposition reaction Methods 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- 238000009826 distribution Methods 0.000 claims description 4
- 230000005484 gravity Effects 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 238000000746 purification Methods 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 238000004064 recycling Methods 0.000 claims description 3
- 238000013022 venting Methods 0.000 claims description 2
- 238000001704 evaporation Methods 0.000 claims 1
- 239000007790 solid phase Substances 0.000 claims 1
- 238000005292 vacuum distillation Methods 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 65
- 208000005156 Dehydration Diseases 0.000 description 11
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 11
- 239000008103 glucose Substances 0.000 description 11
- 239000012071 phase Substances 0.000 description 7
- 240000008042 Zea mays Species 0.000 description 6
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 6
- 238000005755 formation reaction Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 5
- 238000005903 acid hydrolysis reaction Methods 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 235000005822 corn Nutrition 0.000 description 5
- 238000007086 side reaction Methods 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 238000010533 azeotropic distillation Methods 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 244000075850 Avena orientalis Species 0.000 description 3
- 235000007319 Avena orientalis Nutrition 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002518 antifoaming agent Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000010908 decantation Methods 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 2
- 244000299507 Gossypium hirsutum Species 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- 235000007558 Avena sp Nutrition 0.000 description 1
- 108010082495 Dietary Plant Proteins Proteins 0.000 description 1
- 241000287509 Piciformes Species 0.000 description 1
- 241000270295 Serpentes Species 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 239000002154 agricultural waste Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 238000010936 aqueous wash Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000004758 synthetic textile Substances 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 238000010407 vacuum cleaning Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000002699 waste material 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
- C07D307/38—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
- C13—SUGAR INDUSTRY
- C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
- C13K13/00—Sugars not otherwise provided for in this class
- C13K13/002—Xylose
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Furan Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7919935A FR2462433A1 (fr) | 1979-08-03 | 1979-08-03 | Perfectionnements apportes aux procedes et aux appareillages pour l'obtention de furfural a partir de matieres vegetales |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU185421B true HU185421B (en) | 1985-02-28 |
Family
ID=9228585
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU811146A HU185421B (en) | 1979-08-03 | 1980-07-31 | Process and apparatus for producing furfurol from plant materials |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4366322A (enExample) |
| EP (1) | EP0033323B1 (enExample) |
| JP (1) | JPS56501046A (enExample) |
| BR (1) | BR8008782A (enExample) |
| DE (1) | DE3068793D1 (enExample) |
| FR (1) | FR2462433A1 (enExample) |
| HU (1) | HU185421B (enExample) |
| IN (1) | IN153609B (enExample) |
| SU (1) | SU1176840A3 (enExample) |
| WO (1) | WO1981000407A1 (enExample) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2600063A1 (fr) * | 1986-06-11 | 1987-12-18 | Technip Cie | Procede et installation de traitement des matieres vegetales pour produire notamment du furfural |
| AT387408B (de) * | 1987-05-12 | 1989-01-25 | Voest Alpine Ind Anlagen | Kombiniertes verfahren zur thermischen und chemischen behandlung von lignocellulosehaltiger biomasse und zur gewinnung von furfural |
| AT387247B (de) * | 1987-05-12 | 1988-12-27 | Voest Alpine Ind Anlagen | Kombiniertes verfahren zur thermischen und chemischen behandlung von lignocellulosehaltiger biomasse und zur gewinnung von furfural |
| US5559031A (en) * | 1987-08-12 | 1996-09-24 | Technipetrol S.P.A. | Apparatus for the continuous production of ethanol from cereals |
| DE19905655A1 (de) * | 1999-02-11 | 2000-08-17 | Karl Zeitsch | Verfahren zur Herstellung von Furfural durch verzögerte Entspannung |
| GB0601828D0 (en) * | 2006-01-31 | 2006-03-08 | Tapper Company The Ltd S | A Method Of Heat Generation |
| CN1872726A (zh) * | 2006-06-07 | 2006-12-06 | 济南圣泉集团股份有限公司 | 一种糠醛生产废水的处理方法 |
| UA98002C2 (uk) * | 2007-09-07 | 2012-04-10 | Фураникс Технолоджиз Б.В. | Спосіб одержання суміші похідних фурфуралю і 5-алкоксиметилфурфуралю та паливо, що містить таку суміш |
| CN101130532B (zh) * | 2007-09-24 | 2010-11-24 | 济南圣泉集团股份有限公司 | 利用农林废弃物生产糠醛的系统及方法 |
| US8119823B2 (en) * | 2008-07-16 | 2012-02-21 | Renmatix, Inc. | Solvo-thermal hydrolysis of xylose |
| US8282738B2 (en) * | 2008-07-16 | 2012-10-09 | Renmatix, Inc. | Solvo-thermal fractionation of biomass |
| US8546560B2 (en) | 2008-07-16 | 2013-10-01 | Renmatix, Inc. | Solvo-thermal hydrolysis of cellulose |
| BRPI0915930A2 (pt) | 2008-07-16 | 2015-11-03 | Sriya Innovations Inc | método para produção de pelo menos um de glicose e furfural, processo para produção de um produto como xilose e celulose a partir de uma biomassa, processo para hidrolisar celulose e composição compreendendo um produto de hidrólise de celulose |
| FR2936803B1 (fr) | 2008-10-06 | 2012-09-28 | Arkema France | Copolymere a blocs issu de matieres renouvelables et procede de fabrication d'un tel copolymere a blocs. |
| CN105525043B (zh) | 2010-01-19 | 2021-03-19 | 瑞恩麦特克斯股份有限公司 | 使用超临界流体从生物质产生可发酵的糖和木质素 |
| WO2012038968A1 (en) | 2010-09-03 | 2012-03-29 | Ganapati Dadasaheb Yadav | Process for production of furfural from xylose using a heterogeneous mesoporous silica catalyst comprising rare earth metals |
| NL2005588C2 (en) | 2010-10-27 | 2012-05-01 | Univ Delft Tech | Process for the production of furfural from pentoses. |
| WO2012088208A2 (en) * | 2010-12-21 | 2012-06-28 | E. I. Du Pont De Nemours And Company | Methods for furfural production from branched non-fermentable sugars in stillage or syrup |
| US8801859B2 (en) | 2011-05-04 | 2014-08-12 | Renmatix, Inc. | Self-cleaning apparatus and method for thick slurry pressure control |
| MY171010A (en) | 2011-05-04 | 2019-09-23 | Renmatix Inc | Lignin production from lignocellulosic biomass |
| CA2837782A1 (en) * | 2011-06-22 | 2012-12-27 | Basf Se | Method for dehydrating a carbohydrate-comprising composition |
| EP2797906A4 (en) | 2011-12-28 | 2015-06-03 | Du Pont | PROCESS FOR THE PREPARATION OF FURFURAL |
| WO2013102027A1 (en) | 2011-12-28 | 2013-07-04 | E. I. Du Pont De Nemours And Company | Process for the production of furfural |
| WO2013102007A1 (en) * | 2011-12-28 | 2013-07-04 | E. I. Du Pont De Nemours And Company | Process for the production of furfural |
| BR112014016001B8 (pt) | 2011-12-28 | 2019-06-25 | Du Pont | processos |
| US9181210B2 (en) | 2011-12-28 | 2015-11-10 | E I Du Pont De Nemours And Company | Processes for making furfurals |
| US8759498B2 (en) | 2011-12-30 | 2014-06-24 | Renmatix, Inc. | Compositions comprising lignin |
| FR3006687B1 (fr) * | 2013-06-05 | 2015-07-17 | Agro Ind Rech S Et Dev Ard | Procede de production de furfural a partir de biomasse lignocellulosique |
| NL2012819B1 (en) | 2014-05-15 | 2016-03-02 | Univ Delft Tech | Method and Apparatus for Furfural Production. |
| EP4357404A3 (en) | 2014-09-26 | 2024-11-27 | Renmatix Inc. | Cellulose-containing compositions and methods of making same |
| CN108929291A (zh) * | 2017-05-23 | 2018-12-04 | 宁津春蕾生物科技有限公司 | 糠醛的生产工艺 |
| RU2723875C1 (ru) * | 2019-10-22 | 2020-06-17 | Виктор Владимирович Васильев | Способ получения фурфурольной смолы на основе гемицеллюлоз растительного сырья для склеивания древесных материалов |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1735084A (en) * | 1922-09-07 | 1929-11-12 | Quaker Oats Co | Process of manufacturing furfural |
| BE379408A (enExample) * | 1930-04-28 | |||
| DE719704C (de) * | 1936-06-20 | 1942-04-15 | Henkel & Cie Gmbh | Verfahren zur Herstellung von Furfuerol |
| DE740602C (de) * | 1941-02-25 | 1943-11-01 | Chem Fab Loewenberg Dr Warth & | Verfahren zur Herstellung von Furfurol aus Pentosen |
| BE505571A (enExample) * | 1950-09-01 | |||
| GB922685A (en) * | 1960-06-17 | 1963-04-03 | Ledoga Spa | Improvements in or relating to the extraction of xylose from vegetable material |
| US4001283A (en) * | 1974-09-23 | 1977-01-04 | Wells Jr Preston A | Method for the manufacture of furfural using hydrogen chloride |
-
1979
- 1979-08-03 FR FR7919935A patent/FR2462433A1/fr active Pending
-
1980
- 1980-07-31 DE DE8080901462T patent/DE3068793D1/de not_active Expired
- 1980-07-31 WO PCT/FR1980/000128 patent/WO1981000407A1/fr not_active Ceased
- 1980-07-31 US US06/253,851 patent/US4366322A/en not_active Expired - Fee Related
- 1980-07-31 HU HU811146A patent/HU185421B/hu unknown
- 1980-07-31 JP JP50178580A patent/JPS56501046A/ja active Pending
- 1980-07-31 BR BR8008782A patent/BR8008782A/pt unknown
- 1980-11-18 IN IN1285/CAL/80A patent/IN153609B/en unknown
-
1981
- 1981-02-24 EP EP80901462A patent/EP0033323B1/fr not_active Expired
- 1981-04-02 SU SU813273771A patent/SU1176840A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| WO1981000407A1 (fr) | 1981-02-19 |
| US4366322A (en) | 1982-12-28 |
| SU1176840A3 (ru) | 1985-08-30 |
| EP0033323B1 (fr) | 1984-08-01 |
| BR8008782A (pt) | 1981-05-26 |
| IN153609B (enExample) | 1984-07-28 |
| DE3068793D1 (en) | 1984-09-06 |
| FR2462433A1 (fr) | 1981-02-13 |
| EP0033323A1 (fr) | 1981-08-12 |
| JPS56501046A (enExample) | 1981-07-30 |
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