GB587092A - Dehydration of polyhydric alcohols - Google Patents
Dehydration of polyhydric alcoholsInfo
- Publication number
- GB587092A GB587092A GB163/45A GB16345A GB587092A GB 587092 A GB587092 A GB 587092A GB 163/45 A GB163/45 A GB 163/45A GB 16345 A GB16345 A GB 16345A GB 587092 A GB587092 A GB 587092A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ether
- water
- alcohol
- dehydration
- overhead
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/12—Alkadienes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C11/00—Aliphatic unsaturated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
- C07C29/82—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation by azeotropic distillation
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12C—BEER; PREPARATION OF BEER BY FERMENTATION; PREPARATION OF MALT FOR MAKING BEER; PREPARATION OF HOPS FOR MAKING BEER
- C12C11/00—Fermentation processes for beer
- C12C11/02—Pitching yeast
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/06—Halogens; Compounds thereof
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Mycology (AREA)
- Food Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Microbiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
In the dehydration of polyhydric alcohols of at least 4 carbon atoms and having non-vicinal carbinol groups, the products are fractionated to distil an overhead comprising poly-olefin, anunsaturated alcohol intermediate, an ether by-product, light ends, and water which is treated to separate the alcohol intermediate for recycling. Azeotropes rich in ether by-products may be formed and azeotropic agents may be added. When dehydrating diacetone glycol, an ether-rich ternary azeotrope is formed from the C6 unsaturated alcohol intermediate, the C8 cyclic ether, and water from the dehydration. Compositions are given of such azeotropes, and of unsaturated alcohol-water and methyl pentadiene-water azeotropes.ALSO:A polyhydric alcohol of at least 4 carbon atoms and having non-vicinal carbinol groups is dehydrated to a polyolefin by heating in the liquid phase in a catalytic dehydration zone directly communicating with a fractionating zone so as to distil an overhead comprising polyolefin, an unsaturated alcohol intermediate, an ether by-product, light ends, and water, this overhead being treated to separate the alcohol intermediate which is recycled to the dehydration zone. Water of dehydration or fresh water may be introduced into the top of the fractionating zone and the overhead treated in a second fractionating zone to remove as overhead the diene and light ends which are separated in a further fractionation. Bottoms from this second zone are treated to separate the alcohol intermediate for recycling. Azeotroping agents may be added or the water itself may form an ether-rich ternary azeotrope with the ether and the alcohol intermediate. The polyhydric alcohols used may be prepared by hydrogenating the condensation products of aldehydes or ketones prepared, for example, as described in Specification 502,450. Acetone may be condensed to diacetone alcohol, hydrogenated, and the glycol dehydrated to hexadiene with iodine or hydrogen chloride as catalyst by the process of Specification 572,602. Cyclic ethers are formed as by-products, that in the case of dehydration of diacetone glycol to 2-methyl pentadiene apparently having the formula <FORM:0587092/IV/1> The products distilling over from the dehydration kettle, provided with a fractionation column into which water is introduced, are fractionated in a second column where light ends and a methyl pentadiene-water azeotrope are taken off from a mixture of the ether, unsaturated alcohols and water. Hydrogen iodide from the iodine catalyst is stripped by adding alkali. The bottoms are then fractionated to remove water and a ternary azeotrope of ether, alcohol and water, rich in ether, leaving the unsaturated alcohol as bottoms which is recycled to the dehydration kettle. Alternatively, the crude distillate from the first column is separated into an upper organic layer, part of which is returned as reflux, and an aqueous layer. Part of the organic layer is then fractionated to remove light ends, and the bottoms are further fractionated to remove dienes and leave an alcohol-ether mixture which is then treated to remove the ether as by azeotroping, and recover the alcohol for recycling. The results obtained by the first method of working are compared with the normal process wherein both the alcohol and ether are refluxed back, diacetone glycol being dehydrated at about 120-145 DEG C, using 0.05 per cent of iodine catalyst.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US587092XA | 1944-01-03 | 1944-01-03 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB587092A true GB587092A (en) | 1947-04-14 |
Family
ID=22018428
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB163/45A Expired GB587092A (en) | 1944-01-03 | 1945-01-02 | Dehydration of polyhydric alcohols |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB587092A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2489302A1 (en) * | 1980-08-29 | 1982-03-05 | Anic Spa | PROCESS FOR THE PREPARATION OF 2,5-DIMETHYL-2,4-HEXADIENE |
-
1945
- 1945-01-02 GB GB163/45A patent/GB587092A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2489302A1 (en) * | 1980-08-29 | 1982-03-05 | Anic Spa | PROCESS FOR THE PREPARATION OF 2,5-DIMETHYL-2,4-HEXADIENE |
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