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