GB432885A - Manufacture of acenaphthene derivatives - Google Patents
Manufacture of acenaphthene derivativesInfo
- Publication number
- GB432885A GB432885A GB46134A GB46134A GB432885A GB 432885 A GB432885 A GB 432885A GB 46134 A GB46134 A GB 46134A GB 46134 A GB46134 A GB 46134A GB 432885 A GB432885 A GB 432885A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acenaphthene
- chloride
- carboxylic
- ethylanilide
- heated
- 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
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/06—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/54—Preparation of carboxylic acid anhydrides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Acenaphthene derivatives are manufactured by condensing acenaphthene or acenaphthene-5-carboxylic alkylanilide with an alkylphenyl-carbamyl chloride (which may carry a methyl or chloro substituent in the phenyl nucleus) in the presence of an aluminium halide condensing agent, and if desired hydrolysing the resulting acenaphthene-5-carboxylic or-5 : 6-dicarboxylic alkylanilide to yield acenaphthene-5-carboxylic or 5 : 6-dicarboxylic acid or their anhydrides. Suitable hydrolysing agents are sulphuric acid containing water, and alcoholic potassium hydroxide. By heating acenaphthene with ethyl- or methyl-phenyl-carbamyl chloride and aluminium chloride in the absence of a solvent there is directly produced acenaphthene - 5 : 6 - dicarboxylic anhydride. Acenaphthene-5-carboxylic and 5 : 6-dicarboxylic acids are dyestuff intermediates, e.g. they may be oxidized to naphthalene-tri- and tetra-carboxylic acids. In examples: (1) acenaphthene and phenylethylcarbamyl chloride are heated in light petroleum with aluminium chloride to produce acenaphthene-5-carboxylic ethylanilide; (2) the product of (1) is hydrolysed by alcoholic caustic potash to yield acenaphthene-5- carboxylic acid; (3) acenaphthene-5-carboxylic ethylanilide is heated with ethylphenylcarbamyl chloride in chlorobenzene in the presence of anhydrous aluminium chloride, producing acenaphthene-5 : 6-bis-carboxylic ethylanilide; (4) the product of (3) is hydrolysed by 60 per cent sulphuric acid to yield acenaphthene-5 : 6-dicarboxylic acid; (5) acenaphthene and ethyl-phenylcarbamyl chloride are heated in chlorobenzene with anhydrous aluminium chloride to produce the bis-carboxylic ethylanilide; (6) the product of (5) is hydrolysed as in (4); (7) acenaphthene and phenylethylcarbamyl chloride are heated with anhydrous aluminium chloride and the product is boiled up with dilute hydrochloric acid, yielding acenaphthene-5 : 6-dicarboxylic anhydride; (8) phenylmethylcarbamyl chloride is employed in place of the ethyl compound in (7); (9) acenaphthene is heated with phenylethylcarbamyl chloride and anhydrous aluminium chloride to produce acenaphthene-5-carboxylic ethylanilide; (10) o-tolylethylcarbamyl chloride is used instead of the phenyl compound in (1), yielding acenaphthene - 5 - carboxylic ethyl - o - toluidide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB46134A GB432885A (en) | 1934-01-05 | 1934-01-05 | Manufacture of acenaphthene derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB46134A GB432885A (en) | 1934-01-05 | 1934-01-05 | Manufacture of acenaphthene derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB432885A true GB432885A (en) | 1935-08-06 |
Family
ID=9704751
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB46134A Expired GB432885A (en) | 1934-01-05 | 1934-01-05 | Manufacture of acenaphthene derivatives |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB432885A (en) |
-
1934
- 1934-01-05 GB GB46134A patent/GB432885A/en not_active Expired
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