CA1085864A - Process for the preparation of furfural - Google Patents
Process for the preparation of furfuralInfo
- Publication number
- CA1085864A CA1085864A CA275,171A CA275171A CA1085864A CA 1085864 A CA1085864 A CA 1085864A CA 275171 A CA275171 A CA 275171A CA 1085864 A CA1085864 A CA 1085864A
- Authority
- CA
- Canada
- Prior art keywords
- lactose
- acid
- process according
- furfural
- 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.)
- Expired
Links
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 title claims abstract description 52
- 238000000034 method Methods 0.000 title claims abstract description 46
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 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 abstract description 33
- 239000008101 lactose Substances 0.000 claims abstract description 33
- 239000000463 material Substances 0.000 claims abstract description 22
- 238000001256 steam distillation Methods 0.000 claims abstract description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 38
- 239000002994 raw material Substances 0.000 claims description 19
- 239000002023 wood Substances 0.000 claims description 17
- 235000018185 Betula X alpestris Nutrition 0.000 claims description 15
- 235000018212 Betula X uliginosa Nutrition 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 15
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical group OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 13
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 11
- 239000005862 Whey Substances 0.000 claims description 9
- 102000007544 Whey Proteins Human genes 0.000 claims description 9
- 108010046377 Whey Proteins Proteins 0.000 claims description 9
- 102000014171 Milk Proteins Human genes 0.000 claims description 6
- 108010011756 Milk Proteins Proteins 0.000 claims description 6
- 235000021239 milk protein Nutrition 0.000 claims description 6
- 150000004965 peroxy acids Chemical class 0.000 claims description 6
- 239000012141 concentrate Substances 0.000 claims description 5
- 230000001590 oxidative effect Effects 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 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
- 239000007800 oxidant agent Substances 0.000 claims 9
- 150000001720 carbohydrates Chemical class 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 description 12
- 229960000583 acetic acid Drugs 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000010924 continuous production Methods 0.000 description 3
- 230000002349 favourable effect Effects 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
- 240000008042 Zea mays Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 235000014633 carbohydrates Nutrition 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 238000004821 distillation Methods 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
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 150000002972 pentoses Chemical class 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- 241000609240 Ambelania acida Species 0.000 description 1
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- 244000075850 Avena orientalis Species 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 241000905957 Channa melasoma Species 0.000 description 1
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 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
- 230000015572 biosynthetic process Effects 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
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012362 glacial acetic acid 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
- 239000000413 hydrolysate Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 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
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 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
- 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
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 229940116269 uric acid Drugs 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US672,296 | 1976-03-31 | ||
| US05/672,296 US4076733A (en) | 1976-03-31 | 1976-03-31 | Process for the preparation of furfural |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1085864A true CA1085864A (en) | 1980-09-16 |
Family
ID=24697963
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA275,171A Expired CA1085864A (en) | 1976-03-31 | 1977-03-30 | Process for the preparation of 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 |
| DE2712901A1 (de) | 1977-10-13 |
| 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 |
|---|---|---|---|
| MKEX | Expiry |