GB481909A - Manufacture of aromatic compounds alkylated in the nucleus - Google Patents
Manufacture of aromatic compounds alkylated in the nucleusInfo
- Publication number
- GB481909A GB481909A GB2573836A GB2573836A GB481909A GB 481909 A GB481909 A GB 481909A GB 2573836 A GB2573836 A GB 2573836A GB 2573836 A GB2573836 A GB 2573836A GB 481909 A GB481909 A GB 481909A
- Authority
- GB
- United Kingdom
- Prior art keywords
- condensed
- boron fluoride
- acid
- tetradecylene
- olefine
- 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
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
- C07C39/06—Alkylated phenols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
Aromatic compounds are alkylated in the nucleus by reaction with olefine mixtures (or fractions thereof) obtained by polymerizing the olefines resulting from the dehydration of the higher alcohols, containing about 5-12 carbon atoms, obtained in the synthesis of methanol. The dehydration of these alcohols is effected in known manner, e.g. with phosphoric or sulphuric acid, phosphorus pentoxide, or phosphoric acid on a carrier; the polymerization of the olefines so obtained is also effected in known manner, e.g. by means of boron fluoride or its molecular compounds, phosphoric acid or an active earth. The condensation of the polymerized olefines or their fractions with the aromatic compounds is effected in the presence of a condensation catalyst, e.g. boron fluoride and its molecular compounds, aluminium chloride, sulphuric acid, phosphoric acid, perchloric acid, sulphoacetic acid, p-toluenesulphonic acid or an active earth. The aromatic compounds which may be treated include aromatic hydrocarbons, nuclearly hydroxylated aromatic compounds, and acids of the type AXRCOOH, where A is a mono- or poly-nuclear aromatic radicle, X is oxygen or sulphur, and R is an aliphatic hydrocarbon radicle, which may be interrupted by oxygen; specified acids of this type are phenoxyacetic, cresoxyacetic, xylenoxyacetic, naphthoxyacetic, phenylmercaptoacetic, and phenoxyethoxyacetic acids. In the examples: (1) phenol and a tetradecylene are condensed in the presence of boron fluoride to yield a tetradecylphenol; (2) phenol and an olefine polymer of average molecular weight 180 or (example 3) 185 or (example 4) 257 or (example 5) 245 are condensed in the presence of boron fluoride; (6) phenol and a tetradecylene are condensed in the presence of aluminium chloride; (7) o-cresol and a tetradecylene are condensed in the presence of boron fluoride; (8) b -naphthol and a tetradecylene are condensed in acetic acid solution in the presence of boron fluoride; the tetradecyl-b -naphthyl acetate obtained as a by-product is saponified with alcoholic caustic potash; (9) benzene is condensed with a tetradecylene in the presence of boron fluoride and phosphoric acid; (10) naphthalene is condensed with a crude dodecylene in the presence of boron fluoride and phosphoric acid; (11) salicylic acid and an olefine mixture of average molecular weight 185 are condensed in the presence of boron fluoride; (12) phenoxyacetic acid and a dodecylene are condensed in the presence of boron fluoride to yield a dodecylphenoxyacetic acid; (13) phenoxyacetic acid and a tetradecylene or (example 14) an olefine polymer of average molecular weight 185 are condensed in the presence of boron fluoride; (15) phenanthrene and a tetradecylene are condensed in the presence of boron fluoride and phosphoric acid; (16) a mixture of isomeric cresotinic acids and a dodecylene-tetradecylene mixture are condensed in the presence of boron fluoride; in each example, the olefine used is a polymer (generally a dimer or a trimer) of an olefine or olefine mixture obtained by dehydrating a higher alcohol or alcohol mixture (generally an isohexyl or isoheptyl alcohol or a mixture thereof) obtained in the synthesis of methanol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2573836A GB481909A (en) | 1936-09-22 | 1936-09-22 | Manufacture of aromatic compounds alkylated in the nucleus |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2573836A GB481909A (en) | 1936-09-22 | 1936-09-22 | Manufacture of aromatic compounds alkylated in the nucleus |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB481909A true GB481909A (en) | 1938-03-21 |
Family
ID=10232472
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2573836A Expired GB481909A (en) | 1936-09-22 | 1936-09-22 | Manufacture of aromatic compounds alkylated in the nucleus |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB481909A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4267394A (en) * | 1979-03-23 | 1981-05-12 | Phillips Petroleum Company | Phenol alkylation |
| US4385191A (en) * | 1979-12-19 | 1983-05-24 | Standard Oil Company (Indiana) | Recovery of BF3 -free alkylphenol product |
-
1936
- 1936-09-22 GB GB2573836A patent/GB481909A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4267394A (en) * | 1979-03-23 | 1981-05-12 | Phillips Petroleum Company | Phenol alkylation |
| US4385191A (en) * | 1979-12-19 | 1983-05-24 | Standard Oil Company (Indiana) | Recovery of BF3 -free alkylphenol product |
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