DE2712901A1 - Verfahren zur herstellung von furfural - Google Patents
Verfahren zur herstellung von furfuralInfo
- Publication number
- DE2712901A1 DE2712901A1 DE19772712901 DE2712901A DE2712901A1 DE 2712901 A1 DE2712901 A1 DE 2712901A1 DE 19772712901 DE19772712901 DE 19772712901 DE 2712901 A DE2712901 A DE 2712901A DE 2712901 A1 DE2712901 A1 DE 2712901A1
- Authority
- DE
- Germany
- Prior art keywords
- furfural
- lactose
- containing material
- steam distillation
- oxidizing agent
- 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.)
- Withdrawn
Links
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 title claims description 114
- 238000004519 manufacturing process Methods 0.000 title claims description 19
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims description 35
- 239000008101 lactose Substances 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 26
- 239000002994 raw material Substances 0.000 claims description 20
- 239000000463 material Substances 0.000 claims description 18
- 239000002023 wood Substances 0.000 claims description 16
- 235000018185 Betula X alpestris Nutrition 0.000 claims description 14
- 235000018212 Betula X uliginosa Nutrition 0.000 claims description 14
- 238000001256 steam distillation Methods 0.000 claims description 11
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 8
- 239000007800 oxidant agent Substances 0.000 claims description 6
- 150000004965 peroxy acids Chemical class 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 5
- 150000001720 carbohydrates Chemical class 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910017604 nitric acid Inorganic materials 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 229960000583 acetic acid Drugs 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000005862 Whey Substances 0.000 description 6
- 102000007544 Whey Proteins Human genes 0.000 description 6
- 108010046377 Whey Proteins Proteins 0.000 description 6
- 230000002349 favourable effect Effects 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 238000010924 continuous production Methods 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 235000014633 carbohydrates Nutrition 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 210000005069 ears Anatomy 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 150000002972 pentoses Chemical class 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- QIVUCLWGARAQIO-OLIXTKCUSA-N (3s)-n-[(3s,5s,6r)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1h-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide Chemical compound C1([C@H]2[C@H](N(C(=O)[C@@H](NC(=O)C=3C=C4C[C@]5(CC4=NC=3)C3=CC=CN=C3NC5=O)C2)CC(F)(F)F)C)=C(F)C=CC(F)=C1F QIVUCLWGARAQIO-OLIXTKCUSA-N 0.000 description 1
- GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 description 1
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
- 241000609240 Ambelania acida Species 0.000 description 1
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 244000075850 Avena orientalis Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 102000014171 Milk Proteins Human genes 0.000 description 1
- 108010011756 Milk Proteins Proteins 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000010905 bagasse Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 235000013351 cheese Nutrition 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- 150000002402 hexoses Chemical class 0.000 description 1
- 239000010903 husk Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- 239000012528 membrane Substances 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
- 235000021239 milk protein Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Saccharide Compounds (AREA)
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/672,296 US4076733A (en) | 1976-03-31 | 1976-03-31 | Process for the preparation of furfural |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2712901A1 true DE2712901A1 (de) | 1977-10-13 |
Family
ID=24697963
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772712901 Withdrawn DE2712901A1 (de) | 1976-03-31 | 1977-03-24 | Verfahren zur herstellung von furfural |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4076733A (show.php) |
| JP (1) | JPS52118460A (show.php) |
| AT (1) | AT357514B (show.php) |
| CA (1) | CA1085864A (show.php) |
| DE (1) | DE2712901A1 (show.php) |
| DK (1) | DK143077A (show.php) |
| FI (1) | FI771009A7 (show.php) |
| FR (1) | FR2346343A1 (show.php) |
| GB (1) | GB1566044A (show.php) |
| NL (1) | NL7703390A (show.php) |
| SE (1) | SE7703630L (show.php) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4154744A (en) * | 1976-10-12 | 1979-05-15 | Sumitomo Chemical Company, Limited | Process for producing a furan derivative |
| DE10045465A1 (de) * | 2000-09-14 | 2002-03-28 | Karl Zeitsch | Verfahren zur atmosphärischen Herstellung von Furfural mit Hilfe eines gasförmigen Katalysators |
| JP2015180615A (ja) * | 2014-03-07 | 2015-10-15 | 花王株式会社 | フルフラールの製造方法 |
| 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 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2520255A (en) * | 1945-11-17 | 1950-08-29 | Earl A Peterman | Glucuronic acid synthesis |
| CH405352A (de) * | 1958-12-17 | 1966-01-15 | Carlsson Skogh Carl Gunnar | Verfahren zur kontinuierlichen Gewinnung von Furfural aus festen Pentosan- und Pentose-haltigen Rohmaterialien nebst Anordnung zur Ausführung des Verfahrens |
-
1976
- 1976-03-31 US US05/672,296 patent/US4076733A/en not_active Expired - Lifetime
-
1977
- 1977-03-24 DE DE19772712901 patent/DE2712901A1/de not_active Withdrawn
- 1977-03-29 GB GB13059/77A patent/GB1566044A/en not_active Expired
- 1977-03-29 NL NL7703390A patent/NL7703390A/xx not_active Application Discontinuation
- 1977-03-29 SE SE7703630A patent/SE7703630L/xx unknown
- 1977-03-30 CA CA275,171A patent/CA1085864A/en not_active Expired
- 1977-03-31 DK DK143077A patent/DK143077A/da not_active IP Right Cessation
- 1977-03-31 JP JP3551877A patent/JPS52118460A/ja active Pending
- 1977-03-31 FI FI771009A patent/FI771009A7/fi not_active Application Discontinuation
- 1977-03-31 FR FR7709732A patent/FR2346343A1/fr not_active Withdrawn
- 1977-03-31 AT AT223077A patent/AT357514B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| SE7703630L (sv) | 1977-10-01 |
| FI771009A7 (show.php) | 1977-10-01 |
| ATA223077A (de) | 1979-12-15 |
| CA1085864A (en) | 1980-09-16 |
| US4076733A (en) | 1978-02-28 |
| DK143077A (da) | 1977-10-01 |
| JPS52118460A (en) | 1977-10-04 |
| GB1566044A (en) | 1980-04-30 |
| NL7703390A (nl) | 1977-10-04 |
| AT357514B (de) | 1980-07-10 |
| FR2346343A1 (fr) | 1977-10-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |