CA1309403C - Process for the production of xylose - Google Patents
Process for the production of xyloseInfo
- Publication number
- CA1309403C CA1309403C CA000549665A CA549665A CA1309403C CA 1309403 C CA1309403 C CA 1309403C CA 000549665 A CA000549665 A CA 000549665A CA 549665 A CA549665 A CA 549665A CA 1309403 C CA1309403 C CA 1309403C
- Authority
- CA
- Canada
- Prior art keywords
- xylose
- syrup
- ethanol
- range
- containing medium
- 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.)
- Expired - Lifetime
Links
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 title claims abstract description 128
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 title claims abstract description 64
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 title claims abstract description 64
- 238000000034 method Methods 0.000 title claims abstract description 28
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 103
- 235000020357 syrup Nutrition 0.000 claims abstract description 37
- 239000006188 syrup Substances 0.000 claims abstract description 37
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 22
- 230000007062 hydrolysis Effects 0.000 claims abstract description 20
- 239000012978 lignocellulosic material Substances 0.000 claims abstract description 15
- 229920002488 Hemicellulose Polymers 0.000 claims abstract description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229920001221 xylan Polymers 0.000 claims abstract description 10
- 150000004823 xylans Chemical class 0.000 claims abstract description 10
- 238000011282 treatment Methods 0.000 claims abstract description 8
- 239000013078 crystal Substances 0.000 claims description 17
- 239000001913 cellulose Substances 0.000 claims description 10
- 229920002678 cellulose Polymers 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 229920005610 lignin Polymers 0.000 claims description 9
- 239000011260 aqueous acid Substances 0.000 claims description 4
- 239000011347 resin Substances 0.000 claims description 4
- 229920005989 resin Polymers 0.000 claims description 4
- 239000000356 contaminant Substances 0.000 claims description 3
- 230000003301 hydrolyzing effect Effects 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims 2
- 238000000909 electrodialysis Methods 0.000 claims 1
- 238000005342 ion exchange Methods 0.000 claims 1
- 238000000926 separation method Methods 0.000 abstract description 9
- 235000015097 nutrients Nutrition 0.000 abstract 1
- 235000000346 sugar Nutrition 0.000 description 20
- 239000002609 medium Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 239000003456 ion exchange resin Substances 0.000 description 7
- 229920003303 ion-exchange polymer Polymers 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 230000015556 catabolic process Effects 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229920001542 oligosaccharide Polymers 0.000 description 4
- 150000002482 oligosaccharides Chemical class 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000010902 straw Substances 0.000 description 4
- 150000008163 sugars Chemical class 0.000 description 4
- 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 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 241000209140 Triticum Species 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 239000001117 sulphuric acid Substances 0.000 description 3
- 235000011149 sulphuric acid Nutrition 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000011552 falling film Substances 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 239000011369 resultant mixture Substances 0.000 description 2
- 241000609240 Ambelania acida Species 0.000 description 1
- 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 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 239000010905 bagasse Substances 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000549 coloured material Substances 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- -1 formaldehyde guanidine-formaldehyde Chemical compound 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000002972 pentoses Chemical class 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 235000020374 simple syrup Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010907 stover Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- 125000000969 xylosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)CO1)* 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
- C07H3/02—Monosaccharides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Biochemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Saccharide Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Plant Substances (AREA)
- Dry Shavers And Clippers (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Ultra Sonic Daignosis Equipment (AREA)
- Steroid Compounds (AREA)
- Diaphragms For Electromechanical Transducers (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8625095 | 1986-10-20 | ||
| GB868625095A GB8625095D0 (en) | 1986-10-20 | 1986-10-20 | Xylose |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1309403C true CA1309403C (en) | 1992-10-27 |
Family
ID=10606025
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000549665A Expired - Lifetime CA1309403C (en) | 1986-10-20 | 1987-10-19 | Process for the production of xylose |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP0265111B1 (en, 2012) |
| AT (1) | ATE73858T1 (en, 2012) |
| BR (1) | BR8705576A (en, 2012) |
| CA (1) | CA1309403C (en, 2012) |
| DE (1) | DE3777530D1 (en, 2012) |
| DK (1) | DK167693B1 (en, 2012) |
| ES (1) | ES2033319T3 (en, 2012) |
| FI (1) | FI89380C (en, 2012) |
| GB (2) | GB8625095D0 (en, 2012) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2723858B1 (fr) * | 1994-08-30 | 1997-01-10 | Ard Sa | Procede de preparation d'agents tensioactifs a partir de sous-produits du ble et nouveaux xylosides d'alkyle |
| RU2109059C1 (ru) * | 1997-10-30 | 1998-04-20 | Блинков Сергей Дмитриевич | Способ переработки растительного сырья для получения пентозных гидролизатов, содержащих, преимущественно, ксилозу |
| BR9902607B1 (pt) | 1999-06-23 | 2010-08-24 | aparelho e processo de prÉ-hidràlise de biomassa. | |
| BR9902606B1 (pt) * | 1999-06-23 | 2011-04-19 | combustìvel de celulignina catalìtica. | |
| CN102605109A (zh) * | 2012-03-28 | 2012-07-25 | 广西大学 | 一种用甘蔗叶生产木糖的方法 |
| WO2016091588A1 (en) | 2014-12-09 | 2016-06-16 | Bioecon International Holding N.V. | Process for the isolation of monosaccharides |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1567350C3 (de) * | 1964-06-22 | 1974-04-11 | Scholler, Dr.Jur., Heinrich, 8000 Muenchen | Verfahren zur Verzuckerung von Holz |
| US3784408A (en) * | 1970-09-16 | 1974-01-08 | Hoffmann La Roche | Process for producing xylose |
| US3780017A (en) * | 1971-02-25 | 1973-12-18 | Masonite Corp | Production of crystalline xylose |
| NZ209527A (en) * | 1984-09-13 | 1988-10-28 | Jack Tama Haigh Just | Process for the continuous hydrolysis of cellulose-containing material |
-
1986
- 1986-10-20 GB GB868625095A patent/GB8625095D0/en active Pending
-
1987
- 1987-10-06 DE DE87308831T patent/DE3777530D1/de not_active Expired - Fee Related
- 1987-10-06 ES ES198787308831T patent/ES2033319T3/es not_active Expired - Lifetime
- 1987-10-06 EP EP87308831A patent/EP0265111B1/en not_active Expired - Lifetime
- 1987-10-06 GB GB878723401A patent/GB8723401D0/en active Pending
- 1987-10-06 AT AT87308831T patent/ATE73858T1/de not_active IP Right Cessation
- 1987-10-19 BR BR8705576A patent/BR8705576A/pt not_active Application Discontinuation
- 1987-10-19 CA CA000549665A patent/CA1309403C/en not_active Expired - Lifetime
- 1987-10-20 DK DK549587A patent/DK167693B1/da not_active IP Right Cessation
- 1987-10-20 FI FI874605A patent/FI89380C/fi not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FI874605A0 (fi) | 1987-10-20 |
| ATE73858T1 (de) | 1992-04-15 |
| BR8705576A (pt) | 1988-05-24 |
| DK167693B1 (da) | 1993-12-06 |
| EP0265111A2 (en) | 1988-04-27 |
| GB8723401D0 (en) | 1987-11-11 |
| EP0265111A3 (en) | 1989-01-18 |
| FI874605L (fi) | 1988-04-21 |
| FI89380C (fi) | 1993-09-27 |
| FI89380B (fi) | 1993-06-15 |
| DK549587D0 (da) | 1987-10-20 |
| DE3777530D1 (en, 2012) | 1992-04-23 |
| EP0265111B1 (en) | 1992-03-18 |
| GB8625095D0 (en) | 1986-11-26 |
| ES2033319T3 (es) | 1993-03-16 |
| DK549587A (da) | 1988-04-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |