DE2534159A1 - Veresterung von furfurylalkohol und seinen derivaten - Google Patents
Veresterung von furfurylalkohol und seinen derivatenInfo
- Publication number
- DE2534159A1 DE2534159A1 DE19752534159 DE2534159A DE2534159A1 DE 2534159 A1 DE2534159 A1 DE 2534159A1 DE 19752534159 DE19752534159 DE 19752534159 DE 2534159 A DE2534159 A DE 2534159A DE 2534159 A1 DE2534159 A1 DE 2534159A1
- Authority
- DE
- Germany
- Prior art keywords
- mol
- furfuryl
- anhydride
- furfuryl alcohol
- esterification
- 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- Withdrawn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
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 title claims description 60
- 238000005886 esterification reaction Methods 0.000 title claims description 11
- 230000032050 esterification Effects 0.000 title claims description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical group CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- CKOYRRWBOKMNRG-UHFFFAOYSA-N Furfuryl acetate Chemical compound CC(=O)OCC1=CC=CO1 CKOYRRWBOKMNRG-UHFFFAOYSA-N 0.000 claims description 15
- 238000005406 washing Methods 0.000 claims description 10
- -1 aliphatic Acid anhydride Chemical class 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 150000003512 tertiary amines Chemical class 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 4
- FUKOTTQGWQVMQB-UHFFFAOYSA-N (2-bromoacetyl) 2-bromoacetate Chemical compound BrCC(=O)OC(=O)CBr FUKOTTQGWQVMQB-UHFFFAOYSA-N 0.000 claims description 2
- PNVPNXKRAUBJGW-UHFFFAOYSA-N (2-chloroacetyl) 2-chloroacetate Chemical compound ClCC(=O)OC(=O)CCl PNVPNXKRAUBJGW-UHFFFAOYSA-N 0.000 claims description 2
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Chemical group 0.000 claims 3
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- HSRJKNPTNIJEKV-UHFFFAOYSA-N Guaifenesin Chemical compound COC1=CC=CC=C1OCC(O)CO HSRJKNPTNIJEKV-UHFFFAOYSA-N 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 10
- 150000001412 amines Chemical class 0.000 description 7
- 150000008065 acid anhydrides Chemical class 0.000 description 6
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- NDSTUUPEXNCUNW-UHFFFAOYSA-N (5-nitrofuran-2-yl)methanol Chemical compound OCC1=CC=C([N+]([O-])=O)O1 NDSTUUPEXNCUNW-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- VOZFDEJGHQWZHU-UHFFFAOYSA-N (5-methylfuran-2-yl)methanol Chemical compound CC1=CC=C(CO)O1 VOZFDEJGHQWZHU-UHFFFAOYSA-N 0.000 description 1
- PCMLAOQXILPCIL-UHFFFAOYSA-N (5-nitrofuran-2-yl)methyl acetate Chemical compound CC(=O)OCC1=CC=C([N+]([O-])=O)O1 PCMLAOQXILPCIL-UHFFFAOYSA-N 0.000 description 1
- OXHNLMTVIGZXSG-UHFFFAOYSA-N 1-Methylpyrrole Chemical compound CN1C=CC=C1 OXHNLMTVIGZXSG-UHFFFAOYSA-N 0.000 description 1
- LGBXNZSSTFWRFS-UHFFFAOYSA-N 2-Furanylmethyl propanoate Chemical compound CCC(=O)OCC1=CC=CO1 LGBXNZSSTFWRFS-UHFFFAOYSA-N 0.000 description 1
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 238000004380 ashing Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical compound [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 0.000 description 1
- 229940089960 chloroacetate Drugs 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- DIAIBWNEUYXDNL-UHFFFAOYSA-N n,n-dihexylhexan-1-amine Chemical compound CCCCCCN(CCCCCC)CCCCCC DIAIBWNEUYXDNL-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000005303 weighing 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
- C07D307/42—Singly bound oxygen atoms
-
- 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
- C07D307/56—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/70—Nitro radicals
- C07D307/71—Nitro radicals attached in position 5
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0069—Heterocyclic compounds
- C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
- C11B9/0076—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing less than six atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI2424/74A FI53971C (fi) | 1974-08-15 | 1974-08-15 | Foerfarande foer framstaellning av estrar av furfuryalkohol eller dess derivat med laegre alifatiska karbonsyror |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2534159A1 true DE2534159A1 (de) | 1976-02-26 |
Family
ID=8507082
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752534159 Withdrawn DE2534159A1 (de) | 1974-08-15 | 1975-07-31 | Veresterung von furfurylalkohol und seinen derivaten |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4008256A (en, 2012) |
| JP (1) | JPS5143753A (en, 2012) |
| DE (1) | DE2534159A1 (en, 2012) |
| FI (1) | FI53971C (en, 2012) |
| FR (1) | FR2281931A1 (en, 2012) |
| SE (1) | SE418180B (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7355066B1 (en) | 2006-12-04 | 2008-04-08 | Millenium Specialty Chemicals, Inc. | Process for making terpene esters |
| CN102050805B (zh) * | 2010-11-18 | 2012-12-26 | 浙江大学 | 应用介孔酸性材料合成乙酸糠酯的方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE501283A (en, 2012) * | 1950-02-16 | |||
| NL188882B (nl) * | 1953-07-03 | Lansing Sound | Membraanophangconstructie. | |
| US2944059A (en) * | 1956-05-24 | 1960-07-05 | Elming Niels | Synthesis of pyridinols and intermediate |
| GB1168797A (en) * | 1965-12-09 | 1969-10-29 | Nat Res Dev | Cyclopropane Carboxylic Acid Derivatives and their use as Insecticides |
| US3843690A (en) * | 1966-06-28 | 1974-10-22 | Dainippon Jochugiku Kk | Certain substituted furfurylesters of chrysanthemumic acid |
| GB1117625A (en) * | 1966-08-24 | 1968-06-19 | Rexall Drug Chemical | Substituted phthalans |
| US3573328A (en) * | 1967-06-07 | 1971-03-30 | Yoshitomi Pharmaceutical | 5-(2-methoxyethyl) furfuryl chrysanthemate |
| US3669989A (en) * | 1968-06-13 | 1972-06-13 | Sumitomo Chemical Co | Cyclopropanecarboxylic acid esters |
| US3629269A (en) * | 1968-09-26 | 1971-12-21 | Ortho Pharma Corp | Derivatives of the 2-(lower alkyl)-3-(lower alkyl)-4-phenyl-3- or 4-cyclohexenecarboxylic acids |
| US3600407A (en) * | 1969-04-04 | 1971-08-17 | Velsicol Chemical Corp | Furfuryl-2-methoxy-3,6-dichlorobenzoate |
-
1974
- 1974-08-15 FI FI2424/74A patent/FI53971C/fi active
-
1975
- 1975-07-31 DE DE19752534159 patent/DE2534159A1/de not_active Withdrawn
- 1975-08-07 US US05/602,550 patent/US4008256A/en not_active Expired - Lifetime
- 1975-08-13 SE SE7509075A patent/SE418180B/xx unknown
- 1975-08-14 FR FR7525317A patent/FR2281931A1/fr active Granted
- 1975-08-15 JP JP50098653A patent/JPS5143753A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FI53971B (fi) | 1978-05-31 |
| JPS5143753A (en) | 1976-04-14 |
| FR2281931A1 (fr) | 1976-03-12 |
| FR2281931B3 (en, 2012) | 1978-04-07 |
| FI242474A7 (en, 2012) | 1976-02-16 |
| SE7509075L (sv) | 1976-02-16 |
| US4008256A (en) | 1977-02-15 |
| SE418180B (sv) | 1981-05-11 |
| FI53971C (fi) | 1978-09-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8141 | Disposal/no request for examination |