CA1065331A - Method and apparatus for the separation and recovery of furfural and organic volatile acids, such as acetic acid and formic acid, from the process of preparation of furfural - Google Patents
Method and apparatus for the separation and recovery of furfural and organic volatile acids, such as acetic acid and formic acid, from the process of preparation of furfuralInfo
- Publication number
- CA1065331A CA1065331A CA268,788A CA268788A CA1065331A CA 1065331 A CA1065331 A CA 1065331A CA 268788 A CA268788 A CA 268788A CA 1065331 A CA1065331 A CA 1065331A
- Authority
- CA
- Canada
- Prior art keywords
- furfural
- organic acids
- volatile organic
- methanol
- vapor mixture
- 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 158
- 238000000034 method Methods 0.000 title claims abstract description 26
- 238000000926 separation method Methods 0.000 title claims abstract description 16
- 238000011084 recovery Methods 0.000 title claims abstract description 4
- 239000002253 acid Substances 0.000 title abstract description 7
- 238000002360 preparation method Methods 0.000 title abstract description 5
- 150000007513 acids Chemical class 0.000 title abstract description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title description 33
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 title description 14
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 title description 7
- 235000019253 formic acid Nutrition 0.000 title description 7
- 150000007524 organic acids Chemical class 0.000 claims abstract description 29
- 235000005985 organic acids Nutrition 0.000 claims abstract description 26
- 239000000203 mixture Substances 0.000 claims abstract description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 22
- 238000010521 absorption reaction Methods 0.000 claims abstract description 15
- 238000005292 vacuum distillation Methods 0.000 claims abstract description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 51
- 239000000243 solution Substances 0.000 claims description 32
- 238000004821 distillation Methods 0.000 claims description 14
- 238000010992 reflux Methods 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims 3
- 238000005903 acid hydrolysis reaction Methods 0.000 claims 1
- 238000010533 azeotropic distillation Methods 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 15
- 239000000543 intermediate Substances 0.000 description 10
- 238000009835 boiling Methods 0.000 description 5
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000002250 absorbent Substances 0.000 description 2
- 230000002745 absorbent Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 235000018185 Betula X alpestris Nutrition 0.000 description 1
- 235000018212 Betula X uliginosa Nutrition 0.000 description 1
- 238000006066 Comins reaction Methods 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- DERZBLKQOCDDDZ-JLHYYAGUSA-N cinnarizine Chemical compound C1CN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)CCN1C\C=C\C1=CC=CC=C1 DERZBLKQOCDDDZ-JLHYYAGUSA-N 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000003810 ethyl acetate extraction Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000002351 wastewater 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/48—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI760026A FI54923C (fi) | 1976-01-07 | 1976-01-07 | Foerfarande foer separering och tillvaratagande av furfural och organiska flyktiga syror saosom aettiksyra och myrsyra vid furfuralframstaellningsfoerfarandet |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1065331A true CA1065331A (en) | 1979-10-30 |
Family
ID=8509674
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA268,788A Expired CA1065331A (en) | 1976-01-07 | 1976-12-29 | Method and apparatus for the separation and recovery of furfural and organic volatile acids, such as acetic acid and formic acid, from the process of preparation of furfural |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4088660A (en, 2012) |
| AR (1) | AR212708A1 (en, 2012) |
| CA (1) | CA1065331A (en, 2012) |
| DE (1) | DE2700212A1 (en, 2012) |
| FI (1) | FI54923C (en, 2012) |
| FR (1) | FR2337723A1 (en, 2012) |
| HU (1) | HU178709B (en, 2012) |
| IN (1) | IN144970B (en, 2012) |
| PL (1) | PL103109B1 (en, 2012) |
| PT (1) | PT66016B (en, 2012) |
| SE (1) | SE429341B (en, 2012) |
| ZA (1) | ZA767446B (en, 2012) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT365080B (de) * | 1980-03-14 | 1981-12-10 | Kanzler Walter | Verfahren zur extraktion von essigsaeure, ameisen- saeure, gegebenenfalls furfurol |
| US5264623A (en) * | 1993-01-04 | 1993-11-23 | Energy Mines & Resources Canada | Method of producing calcium salts from biomass |
| FI117633B (fi) * | 2000-12-29 | 2006-12-29 | Chempolis Oy | Kemikaalien talteenotto ja valmistus massan valmistuksen yhteydessä |
| FI119557B (fi) * | 2002-03-01 | 2008-12-31 | Chempolis Oy | Reaktiivinen erotus |
| CA2772112A1 (en) | 2009-08-27 | 2011-03-03 | Iogen Energy Corporation | Recovery of volatile carboxylic acids by a stripper- extractor system |
| US8987509B2 (en) * | 2009-08-27 | 2015-03-24 | Iogen Energy Corporation | Recovery of volatile carboxylic acids by extractive evaporation |
| SG187716A1 (en) * | 2010-08-04 | 2013-03-28 | Terrabon Mix Alco Llc | Process and system for separating heavy and light components contained in a vapor mixture |
| CN102351816A (zh) * | 2011-08-11 | 2012-02-15 | 任丘市恒达农产品科技开发有限公司 | 糠醛生产中低沸物的回收利用系统 |
| US9181209B2 (en) | 2011-12-28 | 2015-11-10 | E I Du Pont De Nemours And Company | Process for the production of furfural |
| US9181211B2 (en) | 2011-12-28 | 2015-11-10 | E I Du Pont De Nemours And Company | Process for the production of furfural |
| US20130168227A1 (en) * | 2011-12-28 | 2013-07-04 | E I Du Pont De Nemours And Company | Process for the production of furfural |
| US9181210B2 (en) | 2011-12-28 | 2015-11-10 | E I Du Pont De Nemours And Company | Processes for making furfurals |
| FI129405B (en) | 2016-12-30 | 2022-01-31 | Upm Kymmene Corp | A method and an apparatus for separating furfural |
| CN114471102A (zh) * | 2022-01-27 | 2022-05-13 | 宏业生物科技股份有限公司 | 一种降低糠醛渣VOCs排放的方法 |
| FI20235786A1 (en) * | 2023-07-03 | 2025-01-04 | Chempolis Oy | Apparatus and method for heteroazeotropic extractive distillation |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2818413A (en) * | 1946-01-19 | 1957-12-31 | Oronzio De Nora Impianti | Continuous process for the production of furfural and acetic acid from vegetative material |
| US2689250A (en) * | 1951-04-26 | 1954-09-14 | Oronzio De Nora Impianti | Production of furfural and acetic acid from pentosan containing material |
-
1976
- 1976-01-07 FI FI760026A patent/FI54923C/fi not_active IP Right Cessation
- 1976-12-14 ZA ZA767446A patent/ZA767446B/xx unknown
- 1976-12-17 US US05/751,589 patent/US4088660A/en not_active Expired - Lifetime
- 1976-12-20 IN IN2235/CAL/76A patent/IN144970B/en unknown
- 1976-12-27 PT PT66016A patent/PT66016B/pt unknown
- 1976-12-27 HU HU76RO906A patent/HU178709B/hu unknown
- 1976-12-28 AR AR266017A patent/AR212708A1/es active
- 1976-12-29 CA CA268,788A patent/CA1065331A/en not_active Expired
- 1976-12-30 PL PL1976194853A patent/PL103109B1/pl unknown
- 1976-12-30 FR FR7639670A patent/FR2337723A1/fr active Granted
- 1976-12-30 SE SE7614762A patent/SE429341B/xx unknown
-
1977
- 1977-01-05 DE DE19772700212 patent/DE2700212A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| PT66016B (en) | 1978-06-16 |
| FI54923B (fi) | 1978-12-29 |
| SE429341B (sv) | 1983-08-29 |
| SE7614762L (sv) | 1977-07-08 |
| PL103109B1 (pl) | 1979-05-31 |
| US4088660A (en) | 1978-05-09 |
| AR212708A1 (es) | 1978-09-15 |
| DE2700212A1 (de) | 1977-07-14 |
| HU178709B (en) | 1982-06-28 |
| FI760026A7 (en, 2012) | 1977-07-08 |
| PT66016A (en) | 1977-01-01 |
| FR2337723A1 (fr) | 1977-08-05 |
| IN144970B (en, 2012) | 1978-08-05 |
| FR2337723B3 (en, 2012) | 1979-09-07 |
| FI54923C (fi) | 1979-04-10 |
| ZA767446B (en) | 1977-11-30 |
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