Alternatively, it may be prepared by treating the anhydride with ammonium carbonate or urea. Process for the production of copper phthalocyanine toyo. Phthalimide can be prepared by heating phthalic anhydride with aqueous ammonia giving 9597% yield. In a process for the preparation of phthalimide by reaction of phthalic acid or anhydride with urea, the improvement comprising contacting the phthalic acid or anhydride with urea in the presence of a liquid aromatic reaction medium in which the urea is substantially insoluble and in which the phthalic acid is slightly soluble. This observation helps you think about urea being nucleophilic at nitrogen, just like ebola are nucleophilic a carbon. Phthalic acid and derivatives lorz major reference. Title the reaction between urea and phthalic anhydride. Phthalic anhydride appears as a colorless to white lustrous solid in the form of needles with a mild distinctive odor. Preparation of phthalimide by ammoxidation of oxylene and. I made some phthalimide a couple years ago by three different methods.
Phthalic acid is one of three isomers of benzenedicarboxylic acid, the others. Using the urea natom as a nucleophile, you can attack one of the very electrophilic carbonyl of the anhrdride. The reaction mixture was cooled to room temperature and diluted with toluene 80 ml. What is the mechanism of phthalimide synthesis from phthalic. Phthalimide can be prepared by heating ammonium phthalate, by heating acid ammonium phthalate, and by passing dry ammonia over heated phthalic anhydride. How do you convert phthalic anhydride reacting with urea. Solventfree synthesis of phthalimide under microwave. Synthesis of the mathews reaction, a dry hydrolysis procedure of nitriles by phthalic acid or amides by phthalic anhydride to give.
It can also be produced by ammoxidation of o xylene. Treatment of phthalic anhydrides 1 with urea in the presence of catalytic. Phthalimide can be prepared by heating phthalic anhydride with alcoholic ammonia giving 9597% yield. Phthalimide is a dicarboximide that is 2,3dihydro1hisoindole substituted by oxo groups at positions 1 and 3. Phthalic anhydride is the cyclic dicarboxylic anhydride that is the anhydride of phthalic acid. Phthalic anhydride wikimili, the free encyclopedia. Potassium phthalimide is commercially available and is the potassium salt of phthalimide. Recent advances and future prospects of phthalimide. Preparation of anthranilic acid this compound, oaminobenzoic acid, or aniline2carboxylic acid, is usually prepared, per vogel, from phthalimide by treatment with hypobromite or hypochlorite. After 1520 minutes the mixture turns into a foam then the reaction is complete. Combine fine powders of 70 g of phthalic anhydride with 23 g of urea, pour the mixture 1 l rbf, heat the mixture strongly. The phthalimide obtainable by the process of the invention is a valuable starting material for the preparation of dyes, pesticides. Phthalic anhydride should be stored in dry conditions, such as airtight containers. When the amine is not readily accessible, the direct n alkylation of phthalimides with alcohols under mitsunobu conditions and of potassium phthalimide.
The classical experimental procedures i include a the reaction of phthalic anhydride with conc. Phthalic anhydride is a principal commercial form of phthalic acid. Phthalic anhydride and ammonium hydroxide pthalic anhydride and urea. Synthesis of phthalimide using urea and phthalic anhydride. Cool down the mixture until it is warm and add 300 ml of hot water. It is an isomer of isophthalic acid and terephthalic acid. Frequent shaking is necessary, and the sublimed material must be pushed back. Preparative method of novel phthalocyanines from 3 nitro.
The impurity was formed by the reaction of phthalimide with the iron lining in a flaw of the glass lining of the vessel. In this video, phthalimide is synthesized from phthalic anhydride and urea. Two methods for the preparation of phthalimide, hive. Phthalimide is first treated with sodium hydroxide and then oxidised by using naocl or naobr. Mechanism of phthalimide synthesis from phthalic anhydride and urea. Phthalimide is a useful precursor to anthranilic acid and it can be used to convert alkyl halides into amines. Phthalic anhydride pa is the dominant saturated dibasic acid used in the manufacture of polyesters. What is the mechanism of phthalimide synthesis from. A process for the continuous preparation of phthalimide by reacting phthalic anhydride with ammonia in about the stoichiometric ratio, in a mixing apparatus and subsequently in a reaction tube at a particular flow velocity and a particular temperature.
Two methods for the preparation of phthalimide, hive novel. The most important synthesis of phthalimides is the dehydrative condensation of phthalic anhydride at high temperatures with primary amines, when the amine is available. The phthalimide 95 g, 96% is practically pure and melts at 233234c. Phthalimide is a useful precursor to anthranilic acid and it can be. A new method for preparing 15nlabeled phthalimide from the reaction between phthalic anhydride and 15nurea 99. This colourless solid is an important industrial chemical, especially for the largescale production of plasticizers for plastics. Reaction conditions were the mole ratio of phthalic anhydride to 15n urea 99. First the urea reacts with the phthalic anhydride to form phthalimide, co2, and ammonia.
Synthetic of phthalimides via the reaction of phthalic. Although phthalic acid is of modest commercial importance, the closely related derivative phthalic anhydride is a commodity chemical produced on a large scale. The dihydropyrimidinone derivatives containing phthalimide moiety 110 were obtained by reacting enaminone, 242 e 3dimethylamino prop2enoyl phenyl1hisoindole1,32hdione iv, with urea and different substituted benzaldehydes in the. Synthesis of anthranilic acid from phthalic anhydride. Phthalic anhydride 242, prepared by the oxidation of oxylene, is of major importance to the chemical industry with 1992 production over 400 000 tonnes.
It may be recrystallised from etoh, but the solubility is only slight about 5%. Moderately toxic by inhalation or ingestion and a skin irritant. Phthalic acid is an aromatic dicarboxylic acid, with formula c 6 h 4 co 2 h 2. A new method for preparing 15nlabeled phthalimide from the reaction between phthalic anhydride and 15n urea 99. Mechanism of the reaction between phthalic anhydride and. After a bunch of arrowpushing and proton transfers, you get to phthalimide. Commercially, anthranilic acid is prepared using phthalimide or phthalic anyhdride.
Mechanism of the reaction between phthalic anhydride and an aminodiol. After a bunch of arrowpushing and proton transfers, you get to phthalimide with a c onh2 attached to the nitrogen. Title the reaction between urea and phthalic anhydride under. A process for the production of copper phthalocyanine or its derivative from phthalic anhydride or a phthalic anhydride derivative, ammonia, copper or a copper compound, and urea, the process comprising the steps of a reacting the phthalic anhydride or the phthalic anhydride derivative with ammonia to form phthalimide. It was the first anhydride of a dicarboxylic acid to be used commercially.
A new synthesis of intermediates in the preparation of antisterility factors. Mix phthalic anhyde 10 g and urea 2 g in a 250 ml rbf. It is a cyclic dicarboxylic anhydride and a member of 2benzofurans. Metals solution of lead acetate pbch 3 coo 2, cobalt chloride cocl 2. Heat the flask on an oil bathsand bathheating mantle at 5c till the contents melts, froth up and become solid. What is the mechanism of anthranilic acid synthesis from. Procedure about 20 grams of sodium hydroxide from drain cleaner is added to 100 ml of ice water in a 500 ml widemouthed. I didnt have much time to do chemistry on spring break, unfortunately, but i did get to make some anthranilic acid based on chemplayers video. Phthalimide will be later used for making nbromophthalimide, which is used as an alternative for nbromosuccinimidenbs the mechanism. Phthalimide can be prepared by heating alcoholic ammonia with phthalic anhydride, which yields 9597 per cent. Phthalic anhydride is the organic compound with the formula c6h4co2o. Avoid breathing dust and vapours of phthalic anhydride.
Synthesis of anthranilic acid and phthalic anhydride. Phthalimide can be prepared by heating phthalic anhydride with. Phthalimide w as simpl y and ef fecti vely synthesiz ed fr om urea and phthalic anhydride by solventfree reaction using microwave irradiation. It can also be produced by ammoxidation of oxylene. Apart from its availability and low cost, it is easy to handle, quite stable up to the temperature at which polyester resins are generally prepared, stable under uv radiation, reduces the reaction time and. This is known as the hofmann degradation or hofmann amine synthesis. Phthalimide is used as a precursor to anthranilic acid, a precursor to azo dyes and. Alternatively, it can be prepared by taking ammonium carbonate or urea to treat the anhydride. Can be neutralized with an aqueous alkaline solution to disodium phthalate. The thermal stability of the phthalimide showed that the decomposition temperature.