FR2462433A1 - Perfectionnements apportes aux procedes et aux appareillages pour l'obtention de furfural a partir de matieres vegetales - Google Patents
Perfectionnements apportes aux procedes et aux appareillages pour l'obtention de furfural a partir de matieres vegetales Download PDFInfo
- Publication number
- FR2462433A1 FR2462433A1 FR7919935A FR7919935A FR2462433A1 FR 2462433 A1 FR2462433 A1 FR 2462433A1 FR 7919935 A FR7919935 A FR 7919935A FR 7919935 A FR7919935 A FR 7919935A FR 2462433 A1 FR2462433 A1 FR 2462433A1
- Authority
- FR
- France
- Prior art keywords
- acid
- furfural
- reactor
- hydrolysis
- dehydration
- 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.)
- Pending
Links
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 title claims abstract description 192
- 238000000034 method Methods 0.000 title claims abstract description 69
- 239000000463 material Substances 0.000 title claims abstract description 26
- 239000002253 acid Substances 0.000 claims abstract description 83
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 35
- 230000007062 hydrolysis Effects 0.000 claims abstract description 33
- 238000006297 dehydration reaction Methods 0.000 claims abstract description 29
- 230000018044 dehydration Effects 0.000 claims abstract description 26
- 238000004519 manufacturing process Methods 0.000 claims abstract description 16
- 150000002972 pentoses Chemical class 0.000 claims description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 35
- 235000013311 vegetables Nutrition 0.000 claims description 29
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 27
- 238000003860 storage Methods 0.000 claims description 14
- 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 claims description 11
- 239000008103 glucose Substances 0.000 claims description 11
- 238000000746 purification Methods 0.000 claims description 10
- 235000000346 sugar Nutrition 0.000 claims description 10
- 150000008163 sugars Chemical class 0.000 claims description 10
- 229920002678 cellulose Polymers 0.000 claims description 9
- 239000001913 cellulose Substances 0.000 claims description 9
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 9
- 239000011707 mineral Substances 0.000 claims description 9
- 230000015556 catabolic process Effects 0.000 claims description 8
- 238000006731 degradation reaction Methods 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 8
- 238000004064 recycling Methods 0.000 claims description 7
- 238000004821 distillation Methods 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- 239000012429 reaction media Substances 0.000 claims description 6
- 238000000926 separation method Methods 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 238000009826 distribution Methods 0.000 claims description 4
- 239000002994 raw material Substances 0.000 claims description 4
- 238000009834 vaporization Methods 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 230000003134 recirculating effect Effects 0.000 claims description 3
- 230000008016 vaporization Effects 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims 1
- 238000012856 packing Methods 0.000 claims 1
- 238000005292 vacuum distillation Methods 0.000 claims 1
- -1 FURFURAL PENTOSES Chemical class 0.000 abstract description 2
- 239000005418 vegetable material Substances 0.000 abstract description 2
- 241000196324 Embryophyta Species 0.000 description 22
- 239000000243 solution Substances 0.000 description 22
- 208000005156 Dehydration Diseases 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 15
- 230000008901 benefit Effects 0.000 description 9
- 238000005903 acid hydrolysis reaction Methods 0.000 description 6
- 238000011084 recovery Methods 0.000 description 6
- 238000009434 installation Methods 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 240000008042 Zea mays Species 0.000 description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 238000010533 azeotropic distillation Methods 0.000 description 3
- 235000005822 corn Nutrition 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000002035 prolonged effect Effects 0.000 description 3
- 239000002023 wood Substances 0.000 description 3
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- JCSJTDYCNQHPRJ-MMDFAQQLSA-N beta-D-Xylp-(1->4)-beta-D-Xylp-(1->4)-beta-D-Xylp Chemical compound O[C@@H]1[C@@H](O)[C@H](O)CO[C@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O)[C@H](O)OC2)O)OC1 JCSJTDYCNQHPRJ-MMDFAQQLSA-N 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 230000000295 complement effect Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000004880 explosion Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 241000209763 Avena sativa Species 0.000 description 1
- 235000007558 Avena sp Nutrition 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 108010082495 Dietary Plant Proteins Proteins 0.000 description 1
- 240000001624 Espostoa lanata Species 0.000 description 1
- 235000009161 Espostoa lanata Nutrition 0.000 description 1
- 240000007643 Phytolacca americana Species 0.000 description 1
- 235000009074 Phytolacca americana Nutrition 0.000 description 1
- 238000010793 Steam injection (oil industry) Methods 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 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
- 238000003889 chemical engineering Methods 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 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
- 244000045947 parasite Species 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000010908 plant waste Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003303 reheating Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000004758 synthetic textile Substances 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
- 238000009489 vacuum treatment Methods 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)
Priority Applications (10)
| 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 |
| HU811146A HU185421B (en) | 1979-08-03 | 1980-07-31 | Process and apparatus for producing furfurol from plant materials |
| US06/253,851 US4366322A (en) | 1979-08-03 | 1980-07-31 | Method for the production of furfural from vegetable matter |
| PCT/FR1980/000128 WO1981000407A1 (fr) | 1979-08-03 | 1980-07-31 | Perfectionnements apportes aux procedes et aux appareillages pour l'obtention de furfural a partir de matieres vegetales |
| DE8080901462T DE3068793D1 (en) | 1979-08-03 | 1980-07-31 | Improvements to processes and apparatuses for obtaining furfural from plant materials |
| JP50178580A JPS56501046A (enExample) | 1979-08-03 | 1980-07-31 | |
| BR8008782A BR8008782A (pt) | 1979-08-03 | 1980-07-31 | Aperfeicoamentos feitos nos processos e nas aparelhagens para a obtencao de perfural a partir de materias vegetais |
| IN1285/CAL/80A IN153609B (enExample) | 1979-08-03 | 1980-11-18 | |
| EP80901462A EP0033323B1 (fr) | 1979-08-03 | 1981-02-24 | Perfectionnements apportes aux procedes et aux appareillages pour l'obtention de furfural a partir de matieres vegetales |
| SU813273771A SU1176840A3 (ru) | 1979-08-03 | 1981-04-02 | Способ получени фурфурола |
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 |
|---|---|
| FR2462433A1 true FR2462433A1 (fr) | 1981-02-13 |
Family
ID=9228585
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7919935A Pending 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 |
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 |
| HU185421B (en) | 1985-02-28 |
| DE3068793D1 (en) | 1984-09-06 |
| EP0033323A1 (fr) | 1981-08-12 |
| JPS56501046A (enExample) | 1981-07-30 |
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