GB424659A - Process for the treatment of unsaturated organic halogenated compounds - Google Patents
Process for the treatment of unsaturated organic halogenated compoundsInfo
- Publication number
- GB424659A GB424659A GB26220/33A GB2622033A GB424659A GB 424659 A GB424659 A GB 424659A GB 26220/33 A GB26220/33 A GB 26220/33A GB 2622033 A GB2622033 A GB 2622033A GB 424659 A GB424659 A GB 424659A
- Authority
- GB
- United Kingdom
- Prior art keywords
- chloro
- phenyl
- methylbutene
- under pressure
- chloride
- 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
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
- C07C209/08—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms with formation of amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Unsaturated organic compounds containing at least four carbon atoms and at least one halogen atom linked to a saturated carbon atom are treated under pressure with basic compounds. When a strong base such as an alkali or alkaline earth hydroxide is used, the main product is an unsaturated alcohol obtained by substitution of a hydroxy group for halogen. When a weak basic compound is used, such as basic lead acetate, bismuth subnitrate, bismuth subcarbonate, lead hydroxide, ferrous hydroxide or ferric hydroxide, or preferably an alkali or alkaline earth carbonate or bicarbonate, the main product is an aldehyde or ketone isomeric with the unsaturated alcohol referred to above. When ammonia or a primary or secondary amine is used, unsaturated amines are obtained. Suitable halogenated compounds are 3-chlorobutene-1, 3-chloromethylbutene-2, 1-chloro-3-methylbutene - 2, 3 - chloro - 2 - hydroxymethylpropene-1, 3-chloro-2-chloromethylpropene-1, isobutenyl chloride, 4-chloro-2-methylbutene-1, 3-chloro-2-methylbutene-1, 1-phenyl-2-chloromethyl-3-chloropropene-2, 1-phenyl-1-chloro-2-chloro-methylpropene-1, and 1-phenyl-1-chloro-2-methyl-3-chloropropene-2. When mixtures of such halogenated compounds with compounds containing halogen linked to an unsaturated carbon atom are treated, the compounds of the latter class are unaffected; similarly, when a compound containing one halogen atom linked to a saturated carbon atom and another halogen atom linked to an unsaturated carbon atom is treated, the first halogen atom only reacts. The reaction is preferably effected at 80--250 DEG C. and may be carried out in an autoclave or in baffled tubes through which the reagents are caused to flow. In the examples: (1) isobutenyl chloride, admixed or not with dimethylvinyl chloride, is heated under pressure with aqueous sodium hydroxide; isobutenol is formed, and dimethylvinyl chloride, if present initially, is recovered unchanged; if calcium carbonate is used in place of sodium hydroxide, isobutyraldehyde is obtained as the main product, with subordinate amounts of isobutenol, isobutyraldol, 2 : 2 : 4-trimethylpentadiol-1 : 3, isobutyl alcohol, and salts of isobutyric and hydroxyoctylic acids; (2), (3) and (4) isobutenol is obtained as in example 1, but under different reaction conditions; (5) a chlorinated amylene mixture consisting mainly of isopentenyl chlorides is heated with aqueous caustic soda under pressure; 2-methylbutene-1-ol-3 and 2-methylbutene-2-ol-4 are the main products; (6) a mixture of 1-phenyl-2-chloromethyl-3-chloropropene-2, 1 - phenyl - 1 - chloro - 2 - chloromethylpropene - 1, and 1 - phenyl - 1 - chloro - 2 - methyl - 3 - chloropropene - 2 is heated under pressure with aqueous caustic soda; the products are 1-phenyl-2-hydroxymethyl-3-chloropropene-2, 1-phenyl-1-chloro-2-hydroxymethylpropene-1, and 1-phenyl-1-hydroxy-2-methyl-3-chloropropene-2; (7) isobutenyl chloride is heated under pressure with an aqueous slurry of calcium carbonate; isobutyraldehyde and a subordinate amount of isobutenol are obtained; (8) isobutenyl chloride is heated under pressure with aqueous caustic soda; a mixture of isobutenol, isobutyl alcohol, isobutyraldehyde, isobutyric acid, and 2 : 2 : 4-trimethylpentadiol-1 : 3 is obtained; (9) isobutenyl chloride is heated under pressure with aqueous ammonia; a mixture of amines is obtained, from which mono-, di- and tri-isobutenylamines can be isolated; the compound (CH3)2CHN : C4H7 is also formed; (10) monochlorinated tertiary amylenes are heated under pressure with an aqueous sludge of marble; methylisopropyl ketone and isovaleraldehyde are the main products. The Specification states that the starting materials may contain alkoxy or amino groups. Specification 339,675, [Class 2 (iii)], is referred to. 3-Chlorobutene-1 is prepared from butene-1-o1-3 and anhydrous hydrogen chloride. 3-Chloromethylbutene - 2, 1-chloro - 3 - methylbutene-2, 4-chloro-2-methylbutene-1, and 3-chloro-2-methylbutene-1 are the chief components of the mixture obtained by chlorinating technical tertiary amylenes. 3-Chloro-2-chloromethylpropene-1 occurs in the higher chlorination products of isobutylene. 3-Chloro-2-hydroxymethylpropene-1 is obtainable by careful hydrolysis of 3-chloro-2-chloromethyl-propene-1. Phenylchloropropenes. The phenylchloropropenes used in example 6 are obtained by chlorinating a mixture of phenylisobutenes of the formul C6H5CH : C(CH3)2 and C6H5CH2C (CH3) : CH2 ; the phenylisobutene of the second formula is prepared by treating isobutenyl chloride with phenyl magnesium bromide, and decomposing the product with aqueous hydrochloric acid. The Specification as open to inspection under Sect. 91 is not restricted to the treatment of compounds containing at least four carbon atoms, and refers to the treatment of allyl halides, 2 : 3-dihalogenpropene-1, 2 : 3 : 3-trimethyl-3-halogenpropene-1, and 2-methyl-1 : 3-dihalogenbutene-1. This subject-matter does not appear in the Specification as accepted.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US424659XA | 1932-10-04 | 1932-10-04 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB424659A true GB424659A (en) | 1935-02-26 |
Family
ID=21922076
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB26220/33A Expired GB424659A (en) | 1932-10-04 | 1933-09-22 | Process for the treatment of unsaturated organic halogenated compounds |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB424659A (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2464244A (en) * | 1945-06-19 | 1949-03-15 | California Research Corp | Production of methyl vinyl ketone |
US2481157A (en) * | 1944-10-27 | 1949-09-06 | Universal Oil Prod Co | Treatment of halo-hydrocarbons |
US2658919A (en) * | 1948-10-16 | 1953-11-10 | Universal Oil Prod Co | Production of ketones |
US2667508A (en) * | 1951-12-28 | 1954-01-26 | Standard Oil Co | Prepartion of carboxylic acids from allylic compounds |
-
1933
- 1933-09-22 GB GB26220/33A patent/GB424659A/en not_active Expired
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2481157A (en) * | 1944-10-27 | 1949-09-06 | Universal Oil Prod Co | Treatment of halo-hydrocarbons |
US2464244A (en) * | 1945-06-19 | 1949-03-15 | California Research Corp | Production of methyl vinyl ketone |
US2658919A (en) * | 1948-10-16 | 1953-11-10 | Universal Oil Prod Co | Production of ketones |
US2667508A (en) * | 1951-12-28 | 1954-01-26 | Standard Oil Co | Prepartion of carboxylic acids from allylic compounds |
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