DE1176116B - Verfahren zur Herstellung von 1, 7-Alkandiolen und 1, 7-ªÏ-Arlalkandiolen - Google Patents
Verfahren zur Herstellung von 1, 7-Alkandiolen und 1, 7-ªÏ-ArlalkandiolenInfo
- Publication number
- DE1176116B DE1176116B DEC28285A DEC0028285A DE1176116B DE 1176116 B DE1176116 B DE 1176116B DE C28285 A DEC28285 A DE C28285A DE C0028285 A DEC0028285 A DE C0028285A DE 1176116 B DE1176116 B DE 1176116B
- Authority
- DE
- Germany
- Prior art keywords
- alkanediols
- preparation
- arylalkanediols
- hydrogenated
- tetrahydrofuryl
- 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 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 claims description 9
- 238000004821 distillation Methods 0.000 claims description 7
- 239000007868 Raney catalyst Substances 0.000 claims description 5
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 5
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 5
- 150000002576 ketones Chemical class 0.000 claims description 5
- 239000006227 byproduct Substances 0.000 claims 1
- -1 tetrahydrofuryl alcohols Chemical group 0.000 description 7
- 238000010626 work up procedure Methods 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000001667 (E)-4-furan-2-ylbut-3-en-2-one Substances 0.000 description 1
- BVAGSGSYUAOFPJ-CMDGGOBGSA-N (e)-3-(furan-2-yl)-1-phenylprop-2-en-1-one Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CO1 BVAGSGSYUAOFPJ-CMDGGOBGSA-N 0.000 description 1
- GBKGJMYPQZODMI-SNAWJCMRSA-N (e)-4-(furan-2-yl)but-3-en-2-one Chemical compound CC(=O)\C=C\C1=CC=CO1 GBKGJMYPQZODMI-SNAWJCMRSA-N 0.000 description 1
- XFOMSTHAPYAQGW-UHFFFAOYSA-N 1-(oxolan-2-yl)-5-phenylpentan-3-ol Chemical compound C=1C=CC=CC=1CCC(O)CCC1CCCO1 XFOMSTHAPYAQGW-UHFFFAOYSA-N 0.000 description 1
- JYAGAHANMSZLOE-UHFFFAOYSA-N 1-(oxolan-2-yl)pentan-3-ol Chemical compound CCC(O)CCC1CCCO1 JYAGAHANMSZLOE-UHFFFAOYSA-N 0.000 description 1
- MBRXAPJYCMFTJC-UHFFFAOYSA-N 2-(4-methylhexyl)oxolane Chemical compound CCC(C)CCCC1CCCO1 MBRXAPJYCMFTJC-UHFFFAOYSA-N 0.000 description 1
- KQWMZNNZYONYQW-UHFFFAOYSA-N 2-(4-methylpentyl)oxolane Chemical compound CC(C)CCCC1CCCO1 KQWMZNNZYONYQW-UHFFFAOYSA-N 0.000 description 1
- NXRHOUOTCHJHDB-UHFFFAOYSA-N 2-pentyloxolane Chemical compound CCCCCC1CCCO1 NXRHOUOTCHJHDB-UHFFFAOYSA-N 0.000 description 1
- WSZGTKJTERXZMR-UHFFFAOYSA-N 3-(oxolan-2-yl)-1-phenylpropan-1-ol Chemical compound C=1C=CC=CC=1C(O)CCC1CCCO1 WSZGTKJTERXZMR-UHFFFAOYSA-N 0.000 description 1
- UXMUSYTXSNVRMW-UHFFFAOYSA-N 7-phenylheptan-1-ol Chemical compound OCCCCCCCC1=CC=CC=C1 UXMUSYTXSNVRMW-UHFFFAOYSA-N 0.000 description 1
- LCEREYLDGGGBOK-UHFFFAOYSA-N 8-methylnonane-1,7-diol Chemical compound CC(C)C(O)CCCCCCO LCEREYLDGGGBOK-UHFFFAOYSA-N 0.000 description 1
- XPWRYVIMGIMASM-UHFFFAOYSA-N 9-methyldecane-1,7-diol Chemical compound CC(C)CC(O)CCCCCCO XPWRYVIMGIMASM-UHFFFAOYSA-N 0.000 description 1
- 229910000838 Al alloy Inorganic materials 0.000 description 1
- LAJLYEDJQFGPJZ-UHFFFAOYSA-N C1(=CC=CC=C1)C(CC1OCCC1)CCC Chemical compound C1(=CC=CC=C1)C(CC1OCCC1)CCC LAJLYEDJQFGPJZ-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- ORTYMGHCFWKXHO-UHFFFAOYSA-N diethadione Chemical compound CCC1(CC)COC(=O)NC1=O ORTYMGHCFWKXHO-UHFFFAOYSA-N 0.000 description 1
- 229960003675 diethadione Drugs 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- FVXBCDWMKCEPCL-UHFFFAOYSA-N nonane-1,1-diol Chemical compound CCCCCCCCC(O)O FVXBCDWMKCEPCL-UHFFFAOYSA-N 0.000 description 1
- QUADBKCRXGFGAX-UHFFFAOYSA-N octane-1,7-diol Chemical compound CC(O)CCCCCCO QUADBKCRXGFGAX-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 238000006068 polycondensation reaction 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
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/06—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon 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
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/12—Radicals substituted by oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE639175D BE639175A (en:Method) | 1962-10-27 | ||
| DEC28285A DE1176116B (de) | 1962-10-27 | 1962-10-27 | Verfahren zur Herstellung von 1, 7-Alkandiolen und 1, 7-ªÏ-Arlalkandiolen |
| GB3079763A GB977100A (en) | 1962-10-27 | 1963-08-02 | Improvements in or relating to alkyl and arylalkyl diols |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC28285A DE1176116B (de) | 1962-10-27 | 1962-10-27 | Verfahren zur Herstellung von 1, 7-Alkandiolen und 1, 7-ªÏ-Arlalkandiolen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1176116B true DE1176116B (de) | 1964-08-20 |
Family
ID=7018603
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC28285A Pending DE1176116B (de) | 1962-10-27 | 1962-10-27 | Verfahren zur Herstellung von 1, 7-Alkandiolen und 1, 7-ªÏ-Arlalkandiolen |
Country Status (2)
| Country | Link |
|---|---|
| BE (1) | BE639175A (en:Method) |
| DE (1) | DE1176116B (en:Method) |
-
0
- BE BE639175D patent/BE639175A/xx unknown
-
1962
- 1962-10-27 DE DEC28285A patent/DE1176116B/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| BE639175A (en:Method) |
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