Now go to the chemicalsupply and get a pound or so of. In this video, phthalimide is synthesized from phthalic anhydride and urea. Synthetic of phthalimides via the reaction of phthalic anhydride with. Synthesis of some nphthalimide derivatives and evaluation their. Ac1072500 casno 88993 synonyms 1,2benzenedicarboxylic acid recommended use laboratory chemicals. Phthalic anhydride market size, share, trends, global. Title the reaction between urea and phthalic anhydride under. Phthalimide is first treated with sodium hydroxide and then oxidised by using naocl or naobr. Phthalimide article about phthalimide by the free dictionary. Phthalimide may be prepared by heating phthalic anhydride with aqueous ammonia. Synthesis of anthranilic acid and phthalic anhydride ligand.
It is weakly acidic with ethanolic potassium hydroxide it forms potassium phthalimide. A series of phthalimide ivi were prepared in satisfactory yields by reaction of phthalic anhydride. Phthalimide can be prepared by heating ammonium phthalate, 1 by heating acid ammonium phthalate, 2 and by passing dry ammonia over heated phthalic anhydride. Take the phthalimide and stir it in 25% aqueous koh for 12 hours at 0c and then acidify with hcl to give phthalamidic acid.
Phthalimide is used as a precursor to anthranilic acid, a precursor to azo dyes and saccharin. Or the imide can be reacted with basic naoh naocl in water at 80c and then acidified to give anthranilic acid. Anthranilic acid bookmark dont know if this has been posted here before, but its relevant to the use of the imide. Although phthalic acid is of modest commercial importance, the closely related derivative phthalic anhydride is a commodity chemical produced on a large scale. Us2919282a us351521a us35152153a us2919282a us 2919282 a us2919282 a us 2919282a us 351521 a us351521 a us 351521a us 35152153 a us35152153 a us 35152153a us 2919282 a us2919282 a us 2919282a authority us united states prior art keywords phthalimide mixture phthalide process zinc prior art date 19530427 legal status the legal status is an assumption and is not a legal conclusion. Jun 10, 2003 a process for the preparation of a halogen substitutednalkylphthalimide of the formula comprising heating a halogen substitutednalkyltetrahydrophthalimide of the formula wherein y is a halogen and x is a straight chain or branched alkyl moiety of from 1 to about 18 carbons in the gaseous phase to a temperature less than about 290 c. 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. What is the mechanism of anthranilic acid synthesis from. Phthalic acid is an aromatic dicarboxylic acid, with formula c 6 h 4 co 2 h 2.
Although this is rather low, it is not unexpected, as hofmann rearrangements tend to be low yielding, and chemplayers yield was only 44%. Yep, the same stuff as clorox bleach but twice as strong and several times less expensive. Another method for the preparation of primary amines involves the alkylation of potassium phthalimide according to procedures of gabriel to give nalkylphthalimides, which, on hydrolysis, afford the primary amine and phthalic acid. Market overview, global phthalic anhydride market is projected to register a cagr of 4. Abstract in this research six of nphthalimides of amino acids iiiaf have been synthesized, as a first step, through cyclocondensation of ophthalic acid with. Anthranilic acid and phthalic anhydrides have the ability make ligand complexes with the metal ions, which were found to be important for various applications. Continuous preparation of phthalimide basf aktiengesellschaft. Phthalimide is the organic compound with the formula c6h4co2nh. Unlike most such conversions this happens with ease due to the formation of a 5membered ring. Making phthalic anhydride from phthalic acid youtube. Synthesis of anthranilic acid and phthalic anhydride. The most important synthesis of phthalimides is the dehydrative condensation of phthalic anhydride at high temperatures with primary amines, when the amine is available. Phthalic acid, also called 1, 2benzenedicarboxylic acid, colourless, crystalline organic compound ordinarily produced and sold in the form of its anhydride. Jan 26, 2015 the phthalic acid is then converted to phthalic anhydride by dehydration and sublimation.
Preparation of phthalimide by ammoxidation of oxylene and characterization of vcrosio2 catalyst article in indian journal of chemistry section a 415. The nhydroxynaphthalene sulphonic acid phthalimide 8, thiophenephthalimide derivatives 15. It is an isomer of isophthalic acid and terephthalic acid. It is a white, organic, crystalline compound and is formed through the oxidation of naphthalene or oxylene. Phthalic anhydride and ammonium hydroxide pthalic anhydride and urea. Oct 31, 2017 i make phthalic anhydride from phthalic acid by heating. As indicated above, the phthalic acid or anhydride is contacted with urea in the presence of the aromatic medium at an elevated temperature. Pdf preparation of isatoic anhydride from phthalimide. Preparation of isatoic anhydride from phthalimide article pdf available in organic preparations and procedures international 143. I make phthalic anhydride from phthalic acid by heating. It is a cyclic dicarboxylic anhydride and a member of 2benzofurans. Therefore, gabriel phthalimide synthesis is preferred for synthesising primary amines. Alternatively, it may be prepared by treating the anhydride with ammonium carbonate or urea. It has been found that temperatures within the range of to 230 c.
The annual production of phthalic anhydride exceeded 1,000,000 metric tons in the late 20th century. Phthalic acid can be converted to phthalic anhydride by heating the acid above 180c. What is the mechanism of phthalimide synthesis from phthalic. Synthesis is reported in nanjing gongye daxue xuebao,ziran kexueban, 306, 5153. Phthalic anhydride an overview sciencedirect topics. Product is cleaved by reaction with base or hydrazine, which leads to a stable cyclic product. This is known as the hofmann degradation or hofmann amine synthesis. Phthalic acid definition is any of three isomeric acids c8h6o4 obtained by oxidation of various benzene derivatives. How to make phthalic acid and phthalic anhydride youtube. Moderately toxic by inhalation or ingestion and a skin irritant. Synthetic of phthalimides via the reaction of phthalic. Naoh or hydrazine to form aliphatic primary amines.
Contamination and remediation of phthalic acid esters in. A simple preparation of phthaloyl amino acids via a mild. Uses advised against food, drug, pesticide or biocidal product use. Other articles where phthalic anhydride is discussed. After alkylation, the phthalimid is not nucleophile and does not react anymore. Two methods for the preparation of phthalimide, hive. Preparation of phthalimide by ammoxidation of oxylene and. Phthalic acid esters have been used as plasticizers in numerous products and classified as endocrinedisrupting compounds. 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 method, phthalic acid is produced which can be again converted into phthalimide and used over and over again. Synthesis of anthranilic acid and phthalic anhydride ligand and. As china is one of the largest consumers of phthalic acid esters, some human activities may lead to the accumulation of phthalic acid esters in soil and result in contamination. Preparation of substituted phthalic anhydrides and.
An undergraduate organic laboratory sequence journal of chemical education. Phthalimide is a dicarboximide that is 2,3dihydro1hisoindole substituted by oxo groups at positions 1 and 3. Go to the great big building supply house and pick up a couple of gallons of swimming pool chlorination liquid. Pdf synthesis and characterization of some phthalic acid. Preparation of anthranilic acid this compound, oaminobenzoic acid, or aniline2carboxylic acid, is usually prepared, per vogel, from phthalimide by treatment with hypobromite or hypochlorite. Some synthetic reactions for preparation of phthalimide. Their use can be justified if they are obtained from other sources than from carboxylic acids, e. This acid reacted with naocl gives anthranilic acid. Synthetic of phthalimides via the reaction of phthalic anhydride with amines and evaluating of its biological and anti corrosion activity khuluod fahed hamak chemistry department, college of science damascus university, damascus, syria corres. Retention of the optical configuration during the reaction is. Mechanism of phthalic anhydride synthesis from pthalic. Amides get a molecular rearrangement hoffmann rearrangement with solutions of sodium or potassium. Phthalic acid is synthesized by the double benzylic oxidation of oxylene with potassium permanganate.
Phthalimide is alkylated with alkyl or benzyl halide and then hydrolysed or hydrazinolysis to get pure primary amine. Preparation of the new phthalimide derivatives was performed via. To this solution add 6 g phthalamide and 20 ml 10% koh solution, then heat the solution for 510 minutes till phthalamide dissolves. The preparation of 11 of these phthaloyl derivatives is described, some of which are new. It is used as a precursor to other organic compounds as a masked source of ammonia. In the present study, the attempts were carried to form complexes of anthranilic acid and phthalic anhydride ligand with lead acetate pbch3coo2, cobalt chloride cocl2. Acid anhydrides as activated derivatives of carboxylic acids have found little attention for the preparation of acid halides.
Two methods for the preparation of phthalimide, hive novel. Exhibiting the properties of a weak acid, phthalimide interacts with alkaline solutions, for example, to form metallic derivatives, such as c 8 h 4 o 2 nk, which are used for the synthesis of primary amines. Phthalic anhydride is the cyclic dicarboxylic anhydride that is the anhydride of phthalic acid. Synthetic of phthalimides via the reaction of phthalic anhydride with amines and evaluating of its biological. Recent advances and future prospects of phthalimide derivatives. Frequent shaking is necessary, and the sublimed material must be pushed back occasionally into the reaction flask. Phthalimide is a useful precursor to anthranilic acid and it can be. Title the reaction between urea and phthalic anhydride. Phthalic acid definition of phthalic acid by merriamwebster. Up to the present the method has only failed with tryptophane.
In this process, phthalimide is reacted with alcoholic koh to get potassium phthalimide which reacts with an alkyl halide to form nalkyl phthalimide which on basis hydrolysis gives primary amine and phthalic acid. Phthalimide is an imido derivative of phthalic acid. Phthalic anhydride appears as a colorless to white lustrous solid in the form of needles with a mild distinctive odor. What is the mechanism of phthalimide synthesis from. Phthalimide can be prepared by heating phthalic anhydride with alcoholic ammonia giving 9597% yield. Alternatively phthalimide may be prepared by fusing the anhydride with ammonium carbonate. Phthalimide is the organic compound with the formula c 6 h 4 co 2 nh. Gabriel phthalimide synthesis is method of preparation of aliphatic primary amine from phthalimide and alkyl halide. A series of phthalimide ivi were prepared in satisfactory yields by.
I made some phthalimide a couple years ago by three different methods. In the present study, the attempts were carried to form complexes of anthranilic acid and phthalic anhydride ligand with lead acetate pbch 3 coo 2, cobalt chloride cocl 2. Recent advances and future prospects of phthalimide. When the amine is not readily accessible, the direct n alkylation of phthalimides with alcohols under mitsunobu conditions. Finally, base catalyzed hydrolysis of the phthalimide moiety and the esters, followed by acidification and thermal decarboxylation, produces an amino acid and phthalic acid not shown. Therefore, it is necessary for us to understand the current contamination status and to. The subsequent procedure is the same as when aqueous ammonia is used. This phthalic anhydride will be used in further synthesis to make phenolphthalein and phthalimide. Asian journal of pharmaceutical analysis and medicinal chemistry. Synthesis of the mathews reaction, a dry hydrolysis procedure of nitriles by phthalic acid or amides by phthalic anhydride to give. Safety data sheet creation date 14jan2015 revision date 18jan2018 revision number 3 1. Synthesis of anthranilic acid from phthalic anhydride. The yield and selectivity of phthalic anhydride in the above catalysts are low because of having small surface areas. Phthalic anhydride is used to make polymeric resins called alkyd resins, which are used as coatings, especially for appliances and automobiles.
In this method, phthalic acid is produced which can be again. Phthalic acid is one of three isomers of benzenedicarboxylic acid, the others being isophthalic. The present invention relates to and has for its objects the provision for particular new methods of reacting phthalic acid monoamide, optionally in admixture with phthalimide, i. It can also be produced by ammoxidation of oxylene uses. Commercially, anthranilic acid is prepared using phthalimide or phthalic anyhdride. It is a sublimable white solid that is slightly soluble in water but more so upon addition of base. Phthalimides are converted to primary amines in an efficient, twostage, oneflask operation using nabh 4 2propanol, then acetic acid. A novel route to produce phthalic anhydride by oxidation. Phthalimide reacts with koh to form potassium phthalimide,which further racts with alkyl halide to form alkyl halide to form nalkyl phthalimide. Potassium phthalimide is a nh 2synthon which allows the preparation of primary amines by reaction with alkyl halides. Us3819648a us19844271a us3819648a us 3819648 a us3819648 a us 3819648a us 19844271 a us19844271 a us 19844271a us 3819648 a us3819648 a us 3819648a authority us united states prior art keywords phthalimide reaction urea aromatic phthalic acid prior art date 19711112 legal status the legal status is an assumption and is not a legal conclusion.