GB920834A - Process of purifying ª ,ª -unsaturated aliphatic aldehydes resulting from aldol condensation - Google Patents

Process of purifying ª ,ª -unsaturated aliphatic aldehydes resulting from aldol condensation

Info

Publication number
GB920834A
GB920834A GB17664/59A GB1766459A GB920834A GB 920834 A GB920834 A GB 920834A GB 17664/59 A GB17664/59 A GB 17664/59A GB 1766459 A GB1766459 A GB 1766459A GB 920834 A GB920834 A GB 920834A
Authority
GB
United Kingdom
Prior art keywords
line
column
aldol condensation
methylhexen
organic layer
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
Application number
GB17664/59A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Eastman Kodak Co
Original Assignee
Eastman Kodak Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co
Publication of GB920834A publication Critical patent/GB920834A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/78—Separation; Purification; Stabilisation; Use of additives
    • C07C45/85—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to a chemical modification
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
    • C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/78—Separation; Purification; Stabilisation; Use of additives
    • C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
    • C07C45/82—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
    • C07C45/83—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation by extractive distillation

Abstract

<PICT:0920834/III/1> Alpha, beta-unsaturated aliphatic aldehydes having from 4 to 12 carbon atoms per molecule and produced by the aldol condensation of aliphatic aldehydes having from 2 to 6 carbon atoms per molecule, followed by dehydration of the resulting diols, are purified by separating the organic layer from the aldol condensation and steam distilling it from an aqueous caustic alkali solution of from 0,1 to 10% by weight concentration. The steam distillation decomposes impurities which, in the absence of alkali, would distil over in the same temperature range as the aldehydes (enals) and thus contaminate any saturated alcohols (anols) prepared therefrom by hydrogenation. Such alcohols are desired free from colour for the preparation of esters suitable for use in the plastics industry. Enals exemplified are crotonaldehyde; 2,4-dimethylbuten-2-al; 2-ethylhexen-2-al; 2-methylpenten-2-al; 2-ethylisohexen-2-al; 2-propylhepten-2-al; 2-propyl-4-methylhexen-2-al; 2-isopropyl-5-methylhexen-2-al; 2,4-dimethylpenten-2-al; 2-ethyl-4-methylhexen-2-al; and 4-butylocten-2-al. As shown, the organic layer of the products resulting from aldol condensation and dehydration are fed by line 1 into a steam distillation column 2 operated at a base temperature of 90 DEG -100 DEG C. while a solution of caustic soda or caustic potash of preferably 1% to 3% by weight concentration is fed into the column near its top by line 7. The distillate from column 2 passes to a decanter 5 by way of a condenser 4, and the desired organic layer is withdrawn from the decanter 5 by line 6, the aqueous layer returning to the column 2 via line 7. The caustic alkali solution withdrawn at the base of column 2 passes via line 8 to a heat-exchanger 9 and is returned to column 2 partly via the line 10 and partly via the pump 12 and line 13.ALSO:Alpha, beta-unsaturated aliphatic aldehydes having from 4 to 12 carbon atoms per molecule and produced by the aldol condensation of aliphatic aldehydes having from 2 to 6 carbon atoms per molecule, followed by dehydration of the resulting diols, are purified by separating the organic layer from the aldol condensation and steam distilling it from an aqueous caustic alkali solution of from 0.1 to 10% by weight concentration. The steam distillation decomposes impurities which, in the absence of alkali, would distil over in the same temperature range as the aldehydes (enals) and thus contaminate any saturated alcohols (anols) prepared therefrom by hydrogenation. Such alcohols are desired free from colour for the preparation of esters suitable for use in the plastics industry. Enals exemplified are crotonaldehyde; 2,4 - dimethylbuten - 2 - al; 2-ethylhexen-2-al; 2-methylpenten-2-al; 2-ethylisohexen-2-al; 2-propylhepten-2-al; 2-propyl-4-methylhexen-2-al; 2-isopropyl-5-methylhexen-2-al; 2,4-dimethylpenten-2-al; 2-ethyl-4-methylhexen-2-al; and 4-butylocten-2-al. As shown, the organic layer of the products resulting from aldol condensation and dehydration are fed by line 1 into a steam distillation column 2 operated at a base temperature of 90-100 DEG C. while a solution of caustic soda or caustic potash of preferably 1% to 3% by weight concentration is fed into the column near its top by line 7. The distillate from column 2 passes via a condenser 4 to a decanter 5, whence the desired products are withdrawn via line 6, the aqueous layer returning to column 2 via line 7. The caustic alkali solution withdrawn at the base of column 2 passes via line 8 to a heatexchanger 9 and is returned to column 2 partly via the line 10 and partly by the pump 12 and line 13.
GB17664/59A 1958-05-27 1959-05-25 Process of purifying ª ,ª -unsaturated aliphatic aldehydes resulting from aldol condensation Expired GB920834A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US738049A US3013082A (en) 1958-05-27 1958-05-27 Process of purifying alpha, beta-unsaturated aliphatic aldehydes resulting from aldol condensation

Publications (1)

Publication Number Publication Date
GB920834A true GB920834A (en) 1963-03-13

Family

ID=24966359

Family Applications (1)

Application Number Title Priority Date Filing Date
GB17664/59A Expired GB920834A (en) 1958-05-27 1959-05-25 Process of purifying ª ,ª -unsaturated aliphatic aldehydes resulting from aldol condensation

Country Status (2)

Country Link
US (1) US3013082A (en)
GB (1) GB920834A (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3359324A (en) * 1961-02-01 1967-12-19 Union Carbide Corp Method of preparing 2, 3-dimethyl-4-pentenal
US3247260A (en) * 1961-04-26 1966-04-19 Exxon Research Engineering Co Recovery of products from aldehyde synthesis bottoms
US3432557A (en) * 1966-03-23 1969-03-11 Celanese Corp Aldoling process
GB9615050D0 (en) * 1996-07-17 1996-09-04 Exxon Chemical Patents Inc Recycle and recovery of useful products from heavy aldol by-products

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2096637A (en) * 1926-07-14 1937-10-19 Guinot Henri Martin Emmanuel Process for the manufacture of unsaturated aliphatic aldehydes
US1738659A (en) * 1927-06-29 1929-12-10 Rubber Service Lab Co Aldehyde manufacture
US2852563A (en) * 1955-10-17 1958-09-16 Eastman Kodak Co Condensation of isoaldehydes with lower aliphatic aldehydes

Also Published As

Publication number Publication date
US3013082A (en) 1961-12-12

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