DE1248669B - Verfahren zur Herstellung von 2 3-Dihydrofuranen - Google Patents
Verfahren zur Herstellung von 2 3-DihydrofuranenInfo
- Publication number
- DE1248669B DE1248669B DENDAT1248669D DE1248669DA DE1248669B DE 1248669 B DE1248669 B DE 1248669B DE NDAT1248669 D DENDAT1248669 D DE NDAT1248669D DE 1248669D A DE1248669D A DE 1248669DA DE 1248669 B DE1248669 B DE 1248669B
- Authority
- DE
- Germany
- Prior art keywords
- parts
- dihydrofuran
- dihydrofurans
- catalyst
- preparation
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 10
- ARGCQEVBJHPOGB-UHFFFAOYSA-N 2,5-dihydrofuran Chemical class C1OCC=C1 ARGCQEVBJHPOGB-UHFFFAOYSA-N 0.000 claims description 32
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical class C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 claims description 20
- 239000003054 catalyst Substances 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 238000006317 isomerization reaction Methods 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000007795 chemical reaction product Substances 0.000 description 9
- 239000007858 starting material Substances 0.000 description 8
- 229910052763 palladium Inorganic materials 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000010425 asbestos Substances 0.000 description 4
- 229910052895 riebeckite Inorganic materials 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000004508 fractional distillation Methods 0.000 description 3
- WTDHULULXKLSOZ-UHFFFAOYSA-N hydroxylamine hydrochloride Substances Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- -1 alkene diols Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- OLLPKIZMRLZULO-UHFFFAOYSA-N 2,2,5-trimethyl-3h-furan Chemical compound CC1=CCC(C)(C)O1 OLLPKIZMRLZULO-UHFFFAOYSA-N 0.000 description 1
- CMZLHZPVLJXGLB-UHFFFAOYSA-N 2,5,5-trimethyl-2h-furan Chemical compound CC1OC(C)(C)C=C1 CMZLHZPVLJXGLB-UHFFFAOYSA-N 0.000 description 1
- UZYVJMDRMHWAPX-UHFFFAOYSA-N 2,5-dimethyl-2,5-dihydrofuran Chemical compound CC1OC(C)C=C1 UZYVJMDRMHWAPX-UHFFFAOYSA-N 0.000 description 1
- BGCWDXXJMUHZHE-UHFFFAOYSA-N 5-methyl-2,3-dihydrofuran Chemical compound CC1=CCCO1 BGCWDXXJMUHZHE-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000589614 Pseudomonas stutzeri Species 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 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
- 239000000969 carrier Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 239000007792 gaseous phase Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- WCYJQVALWQMJGE-UHFFFAOYSA-M hydroxylammonium chloride Chemical compound [Cl-].O[NH3+] WCYJQVALWQMJGE-UHFFFAOYSA-M 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- STZCRXQWRGQSJD-GEEYTBSJSA-M methyl orange Chemical compound [Na+].C1=CC(N(C)C)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 STZCRXQWRGQSJD-GEEYTBSJSA-M 0.000 description 1
- 229940012189 methyl orange Drugs 0.000 description 1
- AYOOGWWGECJQPI-NSHDSACASA-N n-[(1s)-1-(5-fluoropyrimidin-2-yl)ethyl]-3-(3-propan-2-yloxy-1h-pyrazol-5-yl)imidazo[4,5-b]pyridin-5-amine Chemical compound N1C(OC(C)C)=CC(N2C3=NC(N[C@@H](C)C=4N=CC(F)=CN=4)=CC=C3N=C2)=N1 AYOOGWWGECJQPI-NSHDSACASA-N 0.000 description 1
- 229910052756 noble gas Inorganic materials 0.000 description 1
- 150000002835 noble gases Chemical class 0.000 description 1
- XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000008096 xylene 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
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/28—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB0080007 | 1965-01-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1248669B true DE1248669B (de) | 1968-03-14 |
Family
ID=6980543
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT1248669D Pending DE1248669B (de) | 1965-01-07 | Verfahren zur Herstellung von 2 3-Dihydrofuranen |
Country Status (2)
| Country | Link |
|---|---|
| BE (1) | BE674652A (cs) |
| DE (1) | DE1248669B (cs) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4206126A (en) | 1978-01-30 | 1980-06-03 | Basf Aktiengesellschaft | Preparation of cyclic α,β-unsaturated ethers |
| FR2603036A1 (fr) * | 1986-08-22 | 1988-02-26 | Rhone Poulenc Agrochimie | Derives de 2,3-dihydrofuranne, leur procede de preparation, leur utilisation comme intermediaire pour la preparation de tetrahydrofuranne |
| WO1992020667A1 (en) * | 1991-05-20 | 1992-11-26 | Eastman Kodak Company | Process for the production of mixtures of 2-hydroxytetrahydrofuran and 4-hydroxybutanal |
| US5536851A (en) * | 1995-01-31 | 1996-07-16 | Eastman Chemical Company | Preparation of 2,3-dihydrofurans |
| WO1996023781A1 (en) * | 1995-01-31 | 1996-08-08 | Eastman Chemical Company | Preparation of 2,3-dihydrofurans |
| US5670672A (en) * | 1995-01-31 | 1997-09-23 | Eastman Chemical Company | Process for the preparation of 2,3-dihydrofurans |
| US5681969A (en) * | 1996-05-03 | 1997-10-28 | Eastman Chemical Company | Continuous process for the conversion of 2,5-dihydrofuran to 2,3-dihydrofuran |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4325753A1 (de) * | 1993-07-31 | 1995-02-02 | Basf Ag | Verfahren zur Herstellung von 1,4-Butandiol |
| CN114349616B (zh) * | 2022-01-10 | 2023-12-26 | 上海巽田科技股份有限公司 | 制备环丙烷甲醛的方法 |
-
0
- DE DENDAT1248669D patent/DE1248669B/de active Pending
-
1965
- 1965-12-31 BE BE674652D patent/BE674652A/fr unknown
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4206126A (en) | 1978-01-30 | 1980-06-03 | Basf Aktiengesellschaft | Preparation of cyclic α,β-unsaturated ethers |
| FR2603036A1 (fr) * | 1986-08-22 | 1988-02-26 | Rhone Poulenc Agrochimie | Derives de 2,3-dihydrofuranne, leur procede de preparation, leur utilisation comme intermediaire pour la preparation de tetrahydrofuranne |
| EP0258160A3 (fr) * | 1986-08-22 | 1988-06-01 | Rhone-Poulenc Agrochimie | Dérivés de 2,3 dihydrofuranne leur procédé de préparation, leur utilisation comme intermédiaire pour la préparation de tétrahydrofuranne |
| WO1992020667A1 (en) * | 1991-05-20 | 1992-11-26 | Eastman Kodak Company | Process for the production of mixtures of 2-hydroxytetrahydrofuran and 4-hydroxybutanal |
| US5254701A (en) * | 1991-05-20 | 1993-10-19 | Eastman Kodak Company | Process for the production of mixtures of 2-hydroxytetrahydrofuran and 4-hydroxybutanal |
| US5536851A (en) * | 1995-01-31 | 1996-07-16 | Eastman Chemical Company | Preparation of 2,3-dihydrofurans |
| WO1996023781A1 (en) * | 1995-01-31 | 1996-08-08 | Eastman Chemical Company | Preparation of 2,3-dihydrofurans |
| US5670672A (en) * | 1995-01-31 | 1997-09-23 | Eastman Chemical Company | Process for the preparation of 2,3-dihydrofurans |
| US5681969A (en) * | 1996-05-03 | 1997-10-28 | Eastman Chemical Company | Continuous process for the conversion of 2,5-dihydrofuran to 2,3-dihydrofuran |
Also Published As
| Publication number | Publication date |
|---|---|
| BE674652A (cs) | 1966-06-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1115238B (de) | Verfahren zur partiellen Hydrierung von Acetylenverbindungen | |
| DE2413178B2 (de) | Verfahren zur Herstellung von 12-Aminododecansäureestern | |
| DE3728222A1 (de) | Verfahren zur herstellung von ethercarbonsaeuren | |
| DE2431242C3 (de) | 2,7,10,15,18,23-Hexamethyltetracosan und Verfahren zu seiner Herstellung | |
| DE1248669B (de) | Verfahren zur Herstellung von 2 3-Dihydrofuranen | |
| DE69009682T2 (de) | Verfahren zur Herstellung von Cyclohexanolderivaten. | |
| DE701825C (de) | Verfahren zur Herstellung von Pyrrolen und hydrierten Pyrrolen | |
| DE2551055A1 (de) | Verfahren zur herstellung von 1,3- oder 1,4-bis-(aminomethyl)-cyclohexan | |
| EP0066212B1 (de) | Verfahren zur katalytischen Hydrierung von Di-(4-aminophenyl)methan | |
| DE1237567B (de) | Verfahren zur Herstellung von delta 5-6-Methylsteroiden | |
| EP1004564B1 (de) | Verfahren zur Herstellung von Hydroxyethylcyclohexanen und Hydroxyethylpiperidinen | |
| DE2609835C3 (de) | Verfahren zur Herstellung von 3-Hydroxybuttersäure-N-arylamiden | |
| DE1174786B (de) | Verfahren zur Herstellung von Azacycloalken-(2, 3)-2-chlor-1-carbonsaeurechloriden | |
| DE2746751A1 (de) | Verfahren zur hydrierung von bis-(2-cyanaethoxy)-verbindungen | |
| AT246721B (de) | Verfahren zur Herstellung des neuen cis,cis-Cyclodecadiens-(1,6) | |
| DE878349C (de) | Verfahren zur Herstellung von hydroaromatischen Carbonsaeuren | |
| DE858094C (de) | Verfahren zur Herstellung von Butandiol-(1, 4) und seinen in 1- oder 1, 4-Stellung durch Kohlenwasserstoffreste oder heterocyclische Reste substituierten Abkoemmlingen | |
| DE1000369B (de) | Verfahren zur Herstellung von Glutarsaeure- und ª‰-Methylglutarsaeuredinitril | |
| AT236929B (de) | Verfahren zur Herstellung von α-Äthylenalkoholen | |
| DE2139084B2 (de) | Verfahren zur Herstellung von 4,4-Diphenyl-piperidinen | |
| EP0051260A1 (de) | Methyl-4-oxatricyclo(5.2.1.02,6)-dec-8-en-3-on (I) und Methyl-4-oxatricyclo(5.2.1.02,6)-decan-3-on (II), deren Herstellung und deren Verwendung als Riechstoffe | |
| DE2153792A1 (de) | Verfahren zur Herstellung von N-Isopropylanilin | |
| DE2028179A1 (de) | Verfahren zur Herstellung von 4-Alkoxy-piperidinen | |
| DE1058062B (de) | Verfahren zur Herstellung von aliphatischen ªÏ, ªÏ'-Diaminen | |
| DE2206805A1 (de) | Verfahren zur kontinuierlichen herstellung von beta-phenyl-aethylalkohol |