GB753218A - Process for the production of acetals - Google Patents
Process for the production of acetalsInfo
- Publication number
- GB753218A GB753218A GB23242/52A GB2324252A GB753218A GB 753218 A GB753218 A GB 753218A GB 23242/52 A GB23242/52 A GB 23242/52A GB 2324252 A GB2324252 A GB 2324252A GB 753218 A GB753218 A GB 753218A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alcohols
- mixture
- hexane
- water
- acid
- 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
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/48—Preparation of compounds having groups
- C07C41/50—Preparation of compounds having groups by reactions producing groups
- C07C41/56—Preparation of compounds having groups by reactions producing groups by condensation of aldehydes, paraformaldehyde, or ketones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/48—Preparation of compounds having groups
- C07C41/50—Preparation of compounds having groups by reactions producing groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/30—Compounds having groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/30—Compounds having groups
- C07C43/303—Compounds having groups having acetal carbon atoms bound to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/21—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C47/22—Acryaldehyde; Methacryaldehyde
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A substantially water-white acetal is obtained by the condensation of an aldehyde (other than acrolein) with an alcohol containing at least 3 carbon atoms in the molecule in the presence of an entraining agent which forms an azeotropic mixture with water and which is substantially inert towards the reactants and the condensation product and in the presence of a quantity of a non-volatile organic acid condensation catalyst constituting less than 0.1 per cent by weight of the reaction mixture. The preferred acids are aromatic sulphonic acids, particularly p-toluene sulphonic acid or benzene sulphonic acid and the acid is preferably used in an amount of 0.01 to 0.05 per cent by weight of the reaction mixture. Specified entraining agents are hydrocarbons or mixtures of hydrocarbons, e.g. a hexane fraction. Particularly suitable aldehydes and/or alcohols are those obtained by the oxo synthesis or from the products obtained by catalytic hydrogenation of carbon monoxide according to the Fischer-Tropsch process in the presence of iron catalysts. The yield of oxygen-containing compositions in the latter process may be increased by converting the olefines present into aldehydes by the addition of water gas and if desired, converting the aldehydes into alcohols by hydrogenation. The aldehyde and alcohol products may be used in admixture or separately. Also, the alcohols obtained by hydrogenation of carbon monoxide may be converted into aldehyde by using copper, zinc, or other dehydrogenation catalysts and these aldehydes may be used together with the alcohols from the same source or with alcohols from a different source. It is preferred to use an excess of 20-50 per cent of the alcohol over the stoichiometric amount required. The acetals formed may be converted into unsaturated ethers by heating them in the presence of small amounts of an acid and the unsaturated ethers may be converted to saturated ethers by hydrogenation. In examples: (1) n-butanol and butyraldehyde are mixed with n-hexane and p-toluene sulphonic acid added to the mixture which is then heated to boiling point in a still provided with a column. The effluent from the top of the column is condensed to give a mixture of water, n-hexane and small amounts of butyraldehyde. The reaction water is continuously separated from the condensate and removed from the process whilst the hexane which contains the butyraldehyde is returned to the still. The acetal formed is fractionally distilled to remove hexane and excess butanol; (2) a gaseous mixture of hydrogen and nitrogen is passed at 310 DEG C. over a catalyst prepared by precipitating an aqueous solution of iron, copper, and calcium nitrates with hot sodium carbonate solution until 70 per cent of the iron has been reduced to the elementary state. Water gas is then passed over the reduced catalyst at elevated temperature and pressure to yield a liquid product containing oxygencontaining compounds (mainly alcohols). The non-aqueous phase of the synthesis product is treated to saponify the esters present and the product extracted with aqueous methanol to yield aliphatic alcohols of four or more carbon atoms; C3-C4 alcohols are recovered from the aqueous phase by distillation in the form of an azeotropic alcohol-water mixture which is then mixed with butyraldehyde and hexane and the mixture reacted in the presence of p-toluene sulphonic acid to form acetals using a procedure similar to that used in (1). Comparative examples are given to show that when sulphonic acid is used and the catalyst in (1) instead of the organic acid the product has a dark colour and is obtained in reduced yield and that when hydrochloric acid is used as the catalyst it distils off and the reaction ceases. Specification 716,541 is referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE753218X | 1951-09-21 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB753218A true GB753218A (en) | 1956-07-18 |
Family
ID=6656480
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB23242/52A Expired GB753218A (en) | 1951-09-21 | 1952-09-16 | Process for the production of acetals |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB753218A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7700814B2 (en) | 2007-03-27 | 2010-04-20 | Exxonmobil Chemical Patents Inc. | Manufacture of alcohols |
-
1952
- 1952-09-16 GB GB23242/52A patent/GB753218A/en not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7700814B2 (en) | 2007-03-27 | 2010-04-20 | Exxonmobil Chemical Patents Inc. | Manufacture of alcohols |
US8288596B2 (en) | 2007-03-27 | 2012-10-16 | Exxonmobil Chemical Patents Inc. | Manufacture of purified alcohols |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
HU177078B (en) | Process for preparing pure methyl-tert.butyl-ether | |
US2042224A (en) | Process of converting a polyhydric alcohol to a carbonyl compound | |
US3173959A (en) | Process for the production of saturated fatty alcohols | |
Gall et al. | The distribution of alcohols in the products of the fischer‐tropsch synthesis | |
US4256913A (en) | Preparation of carboxylic acids using a BF3 catalyst complex | |
US1708460A (en) | Process of manufacturing esters and other valuable organic compounds | |
US2075100A (en) | Dehydrogenation of aliphatic ethers | |
US3518310A (en) | Preparation of beta-hydroxypropionaldehyde and beta-alkoxypropionaldehydes | |
US2390368A (en) | Production of para-divinylbenzene | |
GB1207089A (en) | Process for the manufacture of aliphatic acrylic acid esters | |
US3257459A (en) | Preparation of diethyl ketone in presence of alkaline medium | |
US2491915A (en) | Process for the preparation of acetals | |
US4960961A (en) | Process for the preparation of tert.-amyl alcohol (TAA) | |
DE2103686C3 (en) | Process for the preparation of α-hydroxy-γ-lactones | |
DVORNIKOFF et al. | Condensation of alcohols | |
GB753218A (en) | Process for the production of acetals | |
US3236869A (en) | Allenic acids | |
US2517916A (en) | Branched chain acyclic aldehydes and alcohols and their preparation | |
CA1048534A (en) | Process for preparing allylic esters of carboxylic acids and allylic alcohols | |
Kawamoto et al. | The catalytic reaction of alcohols with reduced copper | |
US2082105A (en) | Production of aliphatic amines | |
JPS6140658B2 (en) | ||
US4029710A (en) | 4-Alkoxy-N-butyraldehyde preparation | |
US2365703A (en) | Alkylated cyclobutane carboxylic acid products and process for producing them | |
EP0079432B1 (en) | Process for the production of methacrylic acid from isobutyraldehyde |