GB813490A - Production of tertiary acetylenic alcohols - Google Patents
Production of tertiary acetylenic alcoholsInfo
- Publication number
- GB813490A GB813490A GB29781/56A GB2978156A GB813490A GB 813490 A GB813490 A GB 813490A GB 29781/56 A GB29781/56 A GB 29781/56A GB 2978156 A GB2978156 A GB 2978156A GB 813490 A GB813490 A GB 813490A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkali metal
- ketone
- methyl
- alcohol
- methyl ethyl
- 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
- 150000001298 alcohols Chemical class 0.000 title abstract 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 abstract 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 6
- 229910052783 alkali metal Inorganic materials 0.000 abstract 6
- 150000001340 alkali metals Chemical class 0.000 abstract 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 5
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-Butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 abstract 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 3
- 150000002576 ketones Chemical class 0.000 abstract 3
- QXLPXWSKPNOQLE-UHFFFAOYSA-N Methylpentynol Chemical compound CCC(C)(O)C#C QXLPXWSKPNOQLE-UHFFFAOYSA-N 0.000 abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 abstract 2
- 230000003472 neutralizing Effects 0.000 abstract 2
- XQEGRAWSNOXZAZ-UHFFFAOYSA-N potassium;1-butoxyethanolate Chemical group [K+].CCCCOC(C)[O-] XQEGRAWSNOXZAZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- UHEPJGULSIKKTP-UHFFFAOYSA-N sulcatone Chemical compound CC(C)=CCCC(C)=O UHEPJGULSIKKTP-UHFFFAOYSA-N 0.000 abstract 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 2
- HXVNBWAKAOHACI-UHFFFAOYSA-N 2,4-Dimethyl-3-pentanone Chemical compound CC(C)C(=O)C(C)C HXVNBWAKAOHACI-UHFFFAOYSA-N 0.000 abstract 1
- CATSNJVOTSVZJV-UHFFFAOYSA-N 2-Heptanone Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 abstract 1
- XNLICIUVMPYHGG-UHFFFAOYSA-N 2-Pentanone Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 abstract 1
- CEBKHWWANWSNTI-UHFFFAOYSA-N 2-methylbut-3-yn-2-ol Chemical compound CC(C)(O)C#C CEBKHWWANWSNTI-UHFFFAOYSA-N 0.000 abstract 1
- SDJUYPUXVFDUFF-UHFFFAOYSA-N 2-propan-2-ylcyclohexan-1-one Chemical compound CC(C)C1CCCCC1=O SDJUYPUXVFDUFF-UHFFFAOYSA-N 0.000 abstract 1
- YEYKMVJDLWJFOA-UHFFFAOYSA-N 2-propoxyethanol Chemical compound CCCOCCO YEYKMVJDLWJFOA-UHFFFAOYSA-N 0.000 abstract 1
- FDPIMTJIUBPUKL-UHFFFAOYSA-N 3-Pentanone Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 abstract 1
- DWAXZMBLTVUSMW-UHFFFAOYSA-N C(CC)OC([O-])C.[K+] Chemical compound C(CC)OC([O-])C.[K+] DWAXZMBLTVUSMW-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 abstract 1
- 150000008041 alkali metal carbonates Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 125000004432 carbon atoms Chemical group C* 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 230000000875 corresponding Effects 0.000 abstract 1
- 239000012043 crude product Substances 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- QRXGHDRJHVYWDC-UHFFFAOYSA-N sodium;1-butoxyethanolate Chemical compound [Na+].CCCCOC(C)[O-] QRXGHDRJHVYWDC-UHFFFAOYSA-N 0.000 abstract 1
- 238000000638 solvent extraction Methods 0.000 abstract 1
- 238000005406 washing Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/05—Preparation of ethers by addition of compounds to unsaturated compounds
- C07C41/06—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
- C07C1/24—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by elimination of water
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/15—Unsaturated ethers containing only non-aromatic carbon-to-carbon double bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Tertiary acetylenic alcohols are produced by reacting acetylene with a ketone under substantially anhydrous conditions and in the presence of an alkali metal alkoxyethoxide of formula ROCH2CH2OM in solution in an alkoxyethanol of formula ROCH2CH2OH, where R in each case represents an alkyl group of one to six carbon atoms, to form the alkali metal derivative of a tertiary acetylenic alcohol, and recovering the alcohol from its alkali metal derivative. Preferably the alkali metal alkoxyethoxide is in solution in the corresponding alkoxyethanol, in which case the solution may be prepared by adding aqueous alkali metal hydroxide to an excess of alkoxyethanol at a subatmospheric pressure, maintaining the mixture at boiling point, and removing water by distillation with a hydrocarbon entraining agent, such as benzene or toluene. A preferred condensing agent is potassium n-butoxyethoxide in n-butoxyethanol. Suitable ketones for carrying out the process are acetone, methyl ethyl ketone, methyl propyl ketone, diethyl ketone, methyl amyl ketone, di-isopropyl ketone, cyclohexanone, and methylheptenone. The molar ratio of ketone to alkoxyethoxide is suitably from 0.30: 1 to 0.95: 1, preferably about 0.75: 1. The condensation may be carried out at below 60 DEG C., preferably 0-30 DEG C. The pressure may be atmospheric or superatmospheric. The tertiary acetylenic alcohol may be liberated from its alkali metal derivative by (i) adding water, extracting with a solvent at a comparatively low temperature, and recovering the free alcohol from the solvent; (ii) hydrolysis, treating with CO2, removing alkali metal carbonate, and solvent extraction; (iii) adding water, removing or neutralizing alkali metal hydroxide, and distilling; (iv) washing the crude product with water, converting the alkali metal derivative to free alcohol, neutralizing alkali metal hydroxide and distilling; (v) (where acetone or methyl ethyl ketone is used) distilling the crude reaction product, after adding water, at not above 60 DEG C. under reduced pressure, e.g. 100-150 mm., to obtain the free alcohol. In Examples (1) and (2) acetone is reacted with acetylene to produce 2-methyl-but-3-yn-2-ol; (3), (4), (5) and (8) methyl ethyl ketone produces 3-methyl-pent-1-yn-3-ol; (6) and (7) 6-methylhept-5-ene-2-one produces dehydrolinalol (all using potassium n-butoxyethoxide in n-butoxyethanol); and methyl ethyl ketone produces 3-methyl-pent-1-yn-3-ol, using (a) potassium n-propoxyethoxide in n-propoxyethanol; and (10) sodium n-butoxyethoxide in n-butoxyethanol.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB813490A true GB813490A (en) | 1959-05-21 |
Family
ID=1741774
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB29781/56A Expired GB813490A (en) | 1956-09-29 | Production of tertiary acetylenic alcohols |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB813490A (en) |
-
1956
- 1956-09-29 GB GB29781/56A patent/GB813490A/en not_active Expired
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