DE2163515B2 - Verfahren zur Herstellung von 2-Alkoxy-3,4-dihydro-2H-pyranen - Google Patents
Verfahren zur Herstellung von 2-Alkoxy-3,4-dihydro-2H-pyranenInfo
- Publication number
- DE2163515B2 DE2163515B2 DE19712163515 DE2163515A DE2163515B2 DE 2163515 B2 DE2163515 B2 DE 2163515B2 DE 19712163515 DE19712163515 DE 19712163515 DE 2163515 A DE2163515 A DE 2163515A DE 2163515 B2 DE2163515 B2 DE 2163515B2
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- vinyl ether
- dihydro
- alkoxy
- zinc
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims 10
- 238000002360 preparation method Methods 0.000 title claims 5
- 238000006243 chemical reaction Methods 0.000 claims description 29
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims description 16
- 239000003054 catalyst Substances 0.000 claims description 8
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 claims description 8
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 4
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 claims description 4
- 238000006116 polymerization reaction Methods 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 3
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 claims description 3
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 claims description 3
- 239000003112 inhibitor Substances 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims 7
- 150000001299 aldehydes Chemical class 0.000 claims 7
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 239000007858 starting material Substances 0.000 claims 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 2
- 238000010438 heat treatment Methods 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 239000007791 liquid phase Substances 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 238000007086 side reaction Methods 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 239000011701 zinc Substances 0.000 claims 2
- 229910052725 zinc Inorganic materials 0.000 claims 2
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 claims 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims 2
- -1 zinc halide Chemical class 0.000 claims 2
- UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 claims 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- 150000001728 carbonyl compounds Chemical class 0.000 claims 1
- 238000010924 continuous production Methods 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 239000011261 inert gas Substances 0.000 claims 1
- 239000002994 raw material Substances 0.000 claims 1
- 229940102001 zinc bromide Drugs 0.000 claims 1
- 235000005074 zinc chloride Nutrition 0.000 claims 1
- 239000011592 zinc chloride Substances 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 description 6
- XCYWUZHUTJDTGS-UHFFFAOYSA-N 2-methoxy-3,4-dihydro-2h-pyran Chemical compound COC1CCC=CO1 XCYWUZHUTJDTGS-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- ZGTXCSJAGJKXKG-UHFFFAOYSA-N 2-butoxy-3,4-dihydro-2h-pyran Chemical compound CCCCOC1CCC=CO1 ZGTXCSJAGJKXKG-UHFFFAOYSA-N 0.000 description 1
- VZJFPIXCMVSTID-UHFFFAOYSA-N 2-ethoxy-3,4-dihydro-2h-pyran Chemical compound CCOC1CCC=CO1 VZJFPIXCMVSTID-UHFFFAOYSA-N 0.000 description 1
- FYICJILYYFSSLQ-UHFFFAOYSA-N 2-ethoxy-4-methyl-3,4-dihydro-2h-pyran Chemical compound CCOC1CC(C)C=CO1 FYICJILYYFSSLQ-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/16—Heterocyclic compounds containing six-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
- C07D309/20—Heterocyclic compounds containing six-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 hydrogen atoms and substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D309/22—Radicals substituted by oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712163515 DE2163515B2 (de) | 1971-12-21 | 1971-12-21 | Verfahren zur Herstellung von 2-Alkoxy-3,4-dihydro-2H-pyranen |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712163515 DE2163515B2 (de) | 1971-12-21 | 1971-12-21 | Verfahren zur Herstellung von 2-Alkoxy-3,4-dihydro-2H-pyranen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2163515A1 DE2163515A1 (de) | 1973-07-05 |
| DE2163515B2 true DE2163515B2 (de) | 1975-01-16 |
| DE2163515C3 DE2163515C3 (enExample) | 1975-08-21 |
Family
ID=5828706
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712163515 Granted DE2163515B2 (de) | 1971-12-21 | 1971-12-21 | Verfahren zur Herstellung von 2-Alkoxy-3,4-dihydro-2H-pyranen |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE2163515B2 (enExample) |
-
1971
- 1971-12-21 DE DE19712163515 patent/DE2163515B2/de active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE2163515C3 (enExample) | 1975-08-21 |
| DE2163515A1 (de) | 1973-07-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHJ | Ceased/non-payment of the annual fee |