N-Methyl Aniline & Anthraquino

Production Process:
i. N-Methylaniline and ii. 2-Aminoanthraquinone
Md. Lutfor Rahman UMP
Preparation of N-Methylaniline from Chlorobenzene

C6H5Cl + 2CH3NH2 ------- Cu2Cl2 ----- C6H5NHCH3 + CH3NH2.HCl The aminolysis of chlorobenzene with methylamine occurs under approximately the same conditions as ammonolysis to give Nmethylaniline. The optimum conditions to be (1) cuprous chloride as catalyst, conc. 0.4-0.6 mole per mole chlorobenzene;

(2) reaction temperature, 215 OC; (3) reaction pressure about 100 psi under conditions; (4) methylamine concentration, 60 per cent in aqeous phase; (5) mole ratio of methylamine to chlorobenzene, 5:1; and (6) reaction time, about 30 min.

Hughes and co-workers have proposed a conditions process (Fig. 1) and have suggested its use for the production of aniline as well as methylaniline. The salient features pertain to the continuous partial elimination of the sodium chloride stemming from the treatment of part of the aqueous portion of the reaction mass with alkali, for the recovery of methylamine without precipitation and filtration of the copper catalyst.

Operations: The charge to the reactor consists of 500 parts by weight of 60 per cent aqueous methylamine and 240 parts by weight of cuprous chloride. Chlorobenzene, 220 parts, is delivered to the reactor by a separate line and the mixture stirred for 30 min, the temperature being kept at 215 OC.

Operations:
The product goes through a condenser to a settler where the lower organic layer is drawn off and sent to a fractionating column.
Here, uncovered chlorobenzene (about 10 per cent) is separated and recycled.

The aqueous layer in the causticizer is treated with stoichometric quantities of sodium hydroxide to decompose the methylamine hydrochloride with the precipitation of salt. If vigorous agitation is employed in this step, the copper catalyst remains in solution and can readily be recycled. The salt is removed in a continuous filter.

To maintain the desired methylamine concentration, the filtrate is divided into two streams. One stream is sent to a methylamine stripper where the amine is removed overhead and blended with the untreated stream.

The catalyst solution remaining in the stripper is drawn off at the base, with just enough water to maintain desired concentrations, and delivered to the mixer. The recycled aqueous methylamine-catalyst mixture is fortified with fresh reactants before entering the reactor.

Vacuum distillation of the product gives two fractions: (1) comprising 92 per cent of the material boiling above chlorobenzene, which contains more than 96 per cent methylaniline, and 3 per cent phenolic impurity;

(2) comprising 8 per cent higher-boiling-point material, which is chiefly a compound of the diphenylamine type, possible N-methyldiphenylamine, CH3.N(C6H5)2. The presence of much tertiary amine suggests that methylaniline is more basic and hence more reactive than aniline under reaction conditions.
2-Aminoanthraquinone from 2-Chloroanthraquinone.

By the use of potassium chlorate and ammonium nitrate as oxidant, it is possible to obtain directly a 2-aminoanthraquinone of 97.598.5 per cent purity. A copper catalysts is not essential but is sometimes used to moderate the conditions of the reaction. The only treatment required is a through washing of the 2-aminoanthraquinone with hot dilute aqueous ammonia or dilute sodium hydroxide.

By employing 7.5 parts of 28 per cent ammonia liquor per part of 2-chloroanthraquinone (molar ratio 25:1) and heating at 200 OC, the reactions can be completed in 24 hours; at 210 OC, only 15 hours is required. It is advisable to fill the autoclave up to 75 per cent of its capacity with the aqueous ammonia in order to ensure against excessive freeboard.

At the completion of the reaction, the ammonia vapour is vented to the absorbers until the residual pressure is about 200 lb. The charge is then delivered to a steel vessel containing dilute sodium hydroxide, to decompose the combined ammonia.

When the hot reaction product is brought is obtained. When the product crystallizes out from its mother liquor in the autoclave, fine long, purplebrown needles are obtained.

The ammonia is removed by distillation with steam, most of the by-product hydroxyl compounds going into solution as the sodium salt during this operation.

The aminoanthraquinone is then filtered hot and washed with hot dilute alkaline solutions. Generally, no purification operation is required.
The results obtained by the procedure are set forth in Table 1.
foregoing

N-Methyl Aniline & Anthraquino

Uploaded by

Copyright:

Available Formats

N-Methyl Aniline & Anthraquino

Uploaded by

Document Information

Original Description:

Copyright

Available Formats

Share this document

Share or Embed Document

Sharing Options

Did you find this document useful?

Is this content inappropriate?

Copyright:

Available Formats

N-Methyl Aniline & Anthraquino

Uploaded by

Copyright:

Available Formats

Production Process:

i. N-Methylaniline and ii. 2-Aminoanthraquinone

Md. Lutfor Rahman UMP

Preparation of N-Methylaniline from Chlorobenzene

Preparation of N-Methylaniline from Chlorobenzene

Preparation of N-Methylaniline from Chlorobenzene

Preparation of N-Methylaniline from Chlorobenzene

Preparation of N-Methylaniline from Chlorobenzene

Preparation of N-Methylaniline from Chlorobenzene

Preparation of N-Methylaniline from Chlorobenzene

Preparation of N-Methylaniline from Chlorobenzene

Preparation of N-Methylaniline from Chlorobenzene

Preparation of N-Methylaniline from Chlorobenzene

2-Aminoanthraquinone from 2-Chloroanthraquinone.

2-Aminoanthraquinone from 2-Chloroanthraquinone.

2-Aminoanthraquinone from 2-Chloroanthraquinone.

2-Aminoanthraquinone from 2-Chloroanthraquinone.

2-Aminoanthraquinone from 2-Chloroanthraquinone.

2-Aminoanthraquinone from 2-Chloroanthraquinone.

The results obtained by the procedure are set forth in Table 1.

You might also like