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. Frequent shaking is necessary, and the sublimed material must be pushed back occasionally into the reaction flask. Phthalimide can be prepared by heating phthalic anhydride with alcoholic ammonia giving 9597% yield. Phthalic anhydride an overview sciencedirect topics. Title the reaction between urea and phthalic anhydride under. Recent advances and future prospects of phthalimide derivatives. 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. When the amine is not readily accessible, the direct n alkylation of phthalimides with alcohols under mitsunobu conditions. Phthalic anhydride and ammonium hydroxide pthalic anhydride and urea.
Alternatively, it may be prepared by treating the anhydride with ammonium carbonate or urea. Synthesis of some nphthalimide derivatives and evaluation their. Phthalic anhydride is used to make polymeric resins called alkyd resins, which are used as coatings, especially for appliances and automobiles. 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. As indicated above, the phthalic acid or anhydride is contacted with urea in the presence of the aromatic medium at an elevated temperature. What is the mechanism of phthalimide synthesis from. The annual production of phthalic anhydride exceeded 1,000,000 metric tons in the late 20th century. A novel route to produce phthalic anhydride by oxidation. Naoh or hydrazine to form aliphatic primary amines.
Phthalic acid, also called 1, 2benzenedicarboxylic acid, colourless, crystalline organic compound ordinarily produced and sold in the form of its anhydride. Two methods for the preparation of phthalimide, hive. It is used as a precursor to other organic compounds as a masked source of ammonia. 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. This is known as the hofmann degradation or hofmann amine synthesis. Therefore, it is necessary for us to understand the current contamination status and to. Two methods for the preparation of phthalimide, hive novel. Synthesis of anthranilic acid from phthalic anhydride. Therefore, gabriel phthalimide synthesis is preferred for synthesising primary amines. 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. Retention of the optical configuration during the reaction is. Safety data sheet creation date 14jan2015 revision date 18jan2018 revision number 3 1.
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. Product is cleaved by reaction with base or hydrazine, which leads to a stable cyclic product. Preparation of anthranilic acid this compound, oaminobenzoic acid, or aniline2carboxylic acid, is usually prepared, per vogel, from phthalimide by treatment with hypobromite or hypochlorite. It has been found that temperatures within the range of to 230 c. Their use can be justified if they are obtained from other sources than from carboxylic acids, e. After alkylation, the phthalimid is not nucleophile and does not react anymore. Phthalimide is alkylated with alkyl or benzyl halide and then hydrolysed or hydrazinolysis to get pure primary amine.
The impurity was formed by the reaction of phthalimide with the iron lining in a flaw of the glass lining of the vessel. Phthalimide is the organic compound with the formula c6h4co2nh. This phthalic anhydride will be used in further synthesis to make phenolphthalein and phthalimide. Jan 26, 2015 the phthalic acid is then converted to phthalic anhydride by dehydration and sublimation. Phthalimide is a useful precursor to anthranilic acid and it can be. Synthetic of phthalimides via the reaction of phthalic anhydride with amines and evaluating of its biological.
Phthalic acid definition of phthalic acid by merriamwebster. Phthalic anhydride market size, share, trends, global. Amides get a molecular rearrangement hoffmann rearrangement with solutions of sodium or potassium. Pdf synthesis and characterization of some phthalic acid. Acid anhydrides as activated derivatives of carboxylic acids have found little attention for the preparation of acid halides.
Commercially, anthranilic acid is prepared using phthalimide or phthalic anyhdride. Phthalic acid definition is any of three isomeric acids c8h6o4 obtained by oxidation of various benzene derivatives. Synthesis of anthranilic acid and phthalic anhydride ligand. I made some phthalimide a couple years ago by three different methods. Up to the present the method has only failed with tryptophane. Alternatively phthalimide may be prepared by fusing the anhydride with ammonium carbonate.
Preparation of substituted phthalic anhydrides and. Phthalimide is used as a precursor to anthranilic acid, a precursor to azo dyes and saccharin. Abstract in this research six of nphthalimides of amino acids iiiaf have been synthesized, as a first step, through cyclocondensation of ophthalic acid with. Market overview, global phthalic anhydride market is projected to register a cagr of 4. Synthesis of the mathews reaction, a dry hydrolysis procedure of nitriles by phthalic acid or amides by phthalic anhydride to give. The preparation of 11 of these phthaloyl derivatives is described, some of which are new. Moderately toxic by inhalation or ingestion and a skin irritant.
How to make phthalic acid and phthalic anhydride youtube. Although this is rather low, it is not unexpected, as hofmann rearrangements tend to be low yielding, and chemplayers yield was only 44%. Ac1072500 casno 88993 synonyms 1,2benzenedicarboxylic acid recommended use laboratory chemicals. Although phthalic acid is of modest commercial importance, the closely related derivative phthalic anhydride is a commodity chemical produced on a large scale. Recent advances and future prospects of phthalimide. The most important synthesis of phthalimides is the dehydrative condensation of phthalic anhydride at high temperatures with primary amines, when the amine is available. In this method, phthalic acid is produced which can be again converted into phthalimide and used over and over again. 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. Title the reaction between urea and phthalic anhydride. This acid reacted with naocl gives anthranilic acid.
Phthalic acid is synthesized by the double benzylic oxidation of oxylene with potassium permanganate. Contamination and remediation of phthalic acid esters in. Gabriel phthalimide synthesis is method of preparation of aliphatic primary amine from phthalimide and alkyl halide. Some synthetic reactions for preparation of phthalimide. 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.
Preparation of isatoic anhydride from phthalimide article pdf available in organic preparations and procedures international 143. 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. Other articles where phthalic anhydride is discussed. Oct 31, 2017 i make phthalic anhydride from phthalic acid by heating. Phthalimide can be prepared by heating ammonium phthalate, 1 by heating acid ammonium phthalate, 2 and by passing dry ammonia over heated phthalic anhydride. It is a white, organic, crystalline compound and is formed through the oxidation of naphthalene or oxylene. Phthalic anhydride is the cyclic dicarboxylic anhydride that is the anhydride of phthalic acid. Synthetic of phthalimides via the reaction of phthalic. 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. An undergraduate organic laboratory sequence journal of chemical education. Go to the great big building supply house and pick up a couple of gallons of swimming pool chlorination liquid. The yield and selectivity of phthalic anhydride in the above catalysts are low because of having small surface areas.
Phthalic anhydride appears as a colorless to white lustrous solid in the form of needles with a mild distinctive odor. Potassium phthalimide is a nh 2synthon which allows the preparation of primary amines by reaction with alkyl halides. Asian journal of pharmaceutical analysis and medicinal chemistry. The nhydroxynaphthalene sulphonic acid phthalimide 8, thiophenephthalimide derivatives 15. Continuous preparation of phthalimide basf aktiengesellschaft. Take the phthalimide and stir it in 25% aqueous koh for 12 hours at 0c and then acidify with hcl to give phthalamidic acid. It is a sublimable white solid that is slightly soluble in water but more so upon addition of base. It is a cyclic dicarboxylic anhydride and a member of 2benzofurans. Pdf preparation of isatoic anhydride from phthalimide. The subsequent procedure is the same as when aqueous ammonia is used. Preparation of the new phthalimide derivatives was performed via.
Uses advised against food, drug, pesticide or biocidal product use. Phthalimide is an imido derivative of phthalic acid. Phthalimide reacts with koh to form potassium phthalimide,which further racts with alkyl halide to form alkyl halide to form nalkyl phthalimide. Yep, the same stuff as clorox bleach but twice as strong and several times less expensive. Phthalimide may be prepared by heating phthalic anhydride with aqueous ammonia.
What is the mechanism of phthalimide synthesis from phthalic. 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. A series of phthalimide ivi were prepared in satisfactory yields by. A simple preparation of phthaloyl amino acids via a mild. It is weakly acidic with ethanolic potassium hydroxide it forms potassium phthalimide. Synthesis is reported in nanjing gongye daxue xuebao,ziran kexueban, 306, 5153. Making phthalic anhydride from phthalic acid youtube.
It is an isomer of isophthalic acid and terephthalic acid. Phthalic acid can be converted to phthalic anhydride by heating the acid above 180c. Unlike most such conversions this happens with ease due to the formation of a 5membered ring. Phthalimide is a dicarboximide that is 2,3dihydro1hisoindole substituted by oxo groups at positions 1 and 3.
Anthranilic acid bookmark dont know if this has been posted here before, but its relevant to the use of the imide. Synthetic of phthalimides via the reaction of phthalic anhydride with. It can also be produced by ammoxidation of oxylene uses. A series of phthalimide ivi were prepared in satisfactory yields by reaction of phthalic anhydride. Now go to the chemicalsupply and get a pound or so of. Synthesis of anthranilic acid and phthalic anhydride. Preparation of phthalimide by ammoxidation of oxylene and characterization of vcrosio2 catalyst article in indian journal of chemistry section a 415. Mechanism of phthalic anhydride synthesis from pthalic. What is the mechanism of anthranilic acid synthesis from. Phthalimide is the organic compound with the formula c 6 h 4 co 2 nh. 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. In this method, phthalic acid is produced which can be again.
To this solution add 6 g phthalamide and 20 ml 10% koh solution, then heat the solution for 510 minutes till phthalamide dissolves. Or the imide can be reacted with basic naoh naocl in water at 80c and then acidified to give anthranilic acid. Phthalic acid is an aromatic dicarboxylic acid, with formula c 6 h 4 co 2 h 2. 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. Phthalimide is first treated with sodium hydroxide and then oxidised by using naocl or naobr. Phthalic acid esters have been used as plasticizers in numerous products and classified as endocrinedisrupting compounds. Preparation of phthalimide by ammoxidation of oxylene and. Phthalimide article about phthalimide by the free dictionary. Anthranilic acid and phthalic anhydrides have the ability make ligand complexes with the metal ions, which were found to be important for various applications.
1339 860 98 497 1218 278 1240 1023 718 1423 175 528 925 78 453 138 1160 248 1190 859 926 716 1046 34 903 1060 477 1064 540 914 5 1357