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Anton S Yegorov Maxin.Pmd BIOSCIENCES BIOTECHNOLOGY RESEARCH ASIA, December 2014. Vol. 11(3), 1765-1779 International and Russian Methods of Synthesis and Use of Pyromellitic acid Dianhydride and Tendencies of Their Development (Review) Anton S. Yegorov*, Vitaly S. Ivanov and Alyona I. Wozniak Federal State Unitary Enterprise «State Scientific Research Institute of Chemical Reagents and High Purity Chemical Substances» (FSUE «IREA») 3,Bogorodsky Val, Moscow, 107076, Russia. doi: http://dx.doi.org/10.13005/bbra/1583 (Received: 30 October 2014; accepted: 05 December 2014) Annotation: Pyromellitic Dianhydride (PMDA) is a raw material for heat resistant polyimide resins, films and coatings.Methods of pyromellitic acid dianhydride synthesis, its properties, use in the industry are in detail considered and structured for the first time herein as well as a possible tendency of these method development is estimated. Key words: Pyromellitic acid, Pyromelliticacid dianhydride, Tetraalkylbenzene, Durene, isodurene, xylene, cumene, pseudocumene, tetramethylbenzol. The fast development of aircraft industry, A huge range of polyimides, based on a rocket building, astronautics, nuclear power, great number of tetracarboxylicacid dianhydrides electronics industry, radio engineering and other is synthesized and characterized by the present technics fields demands polymeric materials of time, but polyimides of dianhydrides of high durability, thermal stability, resistance to pyromellitic(1), diphenyloxidetetracarboxylic(2), nuclear and radiation, elasticity and durability. benzophenonetetracarboxylic(3), perylene- 3,4,9,10 Intensive researches in this field resulted in a – tetracarboxylic (4) acids (Scheme 1) are used in synthesis of a new class of cyclopolymers– practice more often. This paper contains polyimides1, with the above physical and international and national methods of pyromellitic mechanical properties. acid dianhydride synthesis most used in practice 1. The main raw materials for high quality Pyromelliticdianhydride (PMDA) 1 is polymeric materials are dianhydrides of various colourless crystals with fusion temperature of aromatic, heteroaromatic and aliphatic acids, and 287ºC, boiling temperature of 397ºC; dissolved in also diamines with a similar structure2. acetone and dimethyl form amide; under moisture it turns into monoanhydride, and pyromellitic acid (PMA). Pure pyromellitic dianhydride1 is non- degradable at heating to 583-603 K 3. DuPont (USA) approved its semi- * To whom all correspondence should be addressed. industrial production for the first time in 1960. Later E-mail: [email protected] Hexagon (USA) approved the production of this 1766 YEGOROV et al., Biosci., Biotech. Res. Asia, Vol. 11(3), 1765-1779 (2014) Scheme 1. Dianhydrides of pyromellitic(1), diphenyloxidetetracarboxylic(2), benzophenonetetracarboxylic(3), perylene- 3,4,9,10 – tetracarboxylic(4) acids product under the similar technology. In 1964 these second stage, oxidation is completed with two companies received 181 tons of dianhydride1. nitric acid7, 8, 9. Later other largest companies were involved to c) Liquid-phasep rocesses of oxidation of 1 the technology development and production . 3,3',4,4'- tetraalkylbenzene O2 - gas (air) in Now PMDA synthesis is based on 3 main the acetic acid with catalysts - heavy metal methods: salts of variable valency and a) Vapor phase processes of oxidation of halogencompounds at 120-220°C. Catalysts 3,3',4,4'– tetraalkylbenzenes (mainly durene) Co - Mn; Co - Mn - Zr, HBr promoters, at 390-450°C using vanadium - titanic and tetrabromethane, mixture of HBr - HCl10, 11 other catalysts4, 5, 6. are used more often. b) Two-phase processes of oxidation of 3,3',4,4' The most common industrial method of - tetraalkylbenzene (mainly durene). At the pyromellitic dianhydride synthesis is the process first stage, oxidation is fulfilled with O2 - based on catalytic oxidation of durene(5) with air gas (air) in aliphatic carboxylic acid (Scheme 2): (CH3COOH) with cobalt catalyst, at the Scheme 2. Catalytic oxidation of durene(5) The process is usually spent at the present time. Vanadium pentoxide is used as temperature of 410ºC - 450ºC, durene concentration an active base in all cases. Usually an active base in mixture with air 0,1-0,2 % (v), volume speed of with vanadium pentoxide contains lowest durene supply - an air mix 6000-15000 hour-1. vanadium oxides. Oxides of tungsten, phosphorus, Catalysts of vapor phase oxidation of tin, titan, silver, molybdenum, copper, yttrium, durene of numerous types, consisting of an active niobium, and etc are used as co-catalysts. Poor- base, a co-catalyst and a carrier are developed by porous aluminium oxide, silicon carbide, titanium YEGOROV et al., Biosci., Biotech. Res. Asia, Vol. 11(3), 1765-1779 (2014) 1767 oxide, aluminium silicates, and et care used as reduced basically onlyby increasing the industrial carriers. This technology is constantly improved plant capacity. that decreases the productprice. Basing on the literature10, 11, liquid-phase Products of the reaction of vapor phase methods of PMDA synthesis testify that mostly oxidation of durene 5 include other than they are similar and different only by the catalyst pyromellitic dianhydride 1 compounds of partial compound at the oxidation phase (Co - Br; Co - durene oxidation and its deeper oxidation. Mn - Br; Co - Mn - Zr– Brandetc) and reaction Benzenecarboxylicacids, their anhydrides, methods maintaining acatalyst activity by adding derivatives of benzaldehyde, phthalide, phtalan, a proton acid(HBr)oran acid reagent(CCl3OOH) duroquinone are found among products of stronger than acids of tetraalkylbenzene oxidation incomplete oxidation with preserved carbon products. skeleton. Maleic, dimethylmaleic, citraconic and In general, a liquid-phase of PMDA phthalic anhydride, trimellitic acid, acetic acid, synthesis is promising as this technology can be formaldehyde, carbon oxides are found among the used by a single scheme for the synthesis of other deeper oxidation products. dianhydridesof aromatic acids. Basing onthe technology specifics and The two-stage PMDA synthesis by essence for PMDA synthesis by pseudocumene tetraalkylbenzene oxidation at the first phase of condensation with formaldehyde,product O2–with gas (air), at the second phase – with nitric condensation hydrocracking, followed by durene acid7, 8, 9 (Scheme 3) had been widely used before, release and durenevapor-phase oxidation to but in recent years because of competing vapor pyromellitic dianhydride1,the conclusion can be phase and liquid phase processes, its use made that currently the process almost reached decreased, however not stopped yet. perfection and the further product cost can be O OH + O HO 2 HO + O O 5 HNO3 O O HO OH HO OH O O 6 Scheme 3.The two-stage PMDA synthesis Their use was decreased because of c) Formation of explosive compounds; certain disadvantages: d) Equipment destruction caused by a) Formation of large amount of intermediate corrosion; difficult-to-separate products; e) A complex process scheme associated with b) Formation of large amount (10%) of nitro the need of regeneration of two corrosive compounds, leading to a product active reagents (CH3COOH and HNO3). coloration; However, an oxidation with a nitric acid 1768 YEGOROV et al., Biosci., Biotech. Res. Asia, Vol. 11(3), 1765-1779 (2014) quite successively competes with a vapor unacceptable due to the consumption of equimolar phaseoxidation because of higher yield of the amount of the latter (CH3COOH is formed). Some desired product. methods of thermal anhydridization were tested: Pyromellitic acid 6 can be anhydridized sublimation, heating under nitrogen and with high- by chemical dehydrating agents (usually, boiling solvents. An hydridization is more rational aceticanhydride) and thermally (Scheme 4). An in high-boiling solvents, improving heat hydridization with an acetic anhydrideis technically dissipation condition. Scheme 4. Anhydridization of pyromellitic acid 6 Anhydridization begins at about 180- isomerization); 190°C, violently proceeds at220-240°C and finishes 2) High-boiling methylation (300-350°C) of p- within 20-30min.Water vapor are removed inthe xylene or pseudocumene by methanol on form of pseudoazeotrope with diphenylseparated aluminosilicate catalysts; from water after condensation and recycled into 3) Catalytic alkylation of p-xylene or the process. PMDA is to be washed with pseudocumene by ethylene orpropylene; boilingdioxane (~4 weight parts per1 weight part 4) Pseudocumene condensation with of PMDA) and dried at 100-120°C and a residual formaldehyde and di-pseudocumene- pressure of 200-300 mm Hg for 10-15hours. PMDA methane formation and the further outputis 92-93% of theoretical.The obtained hydrocracking in to pseudocumene and dianhydrideis melted at 286-287°C,its acid number- durene; 1026 (calculated 1027), the content of nitro 5) Chloromethylation of p-xylene or compounds is in significant (traces)12. pseudocumene. Raw materials for the pyromelliticdianhydride The above methodsare complex and synthesis expensive. Especially it concerns to atechnology Now a days 3,3',4,4'-tetra-alkylbenzoles of the pure durene preparation from aromatic are used as raw materials to get PMDA, (mainly, concentrates of the petroleum refining with a high durene) released from petroleum refining products content of difficult-to-separate alkylaromatic or synthesized from hydrocarbonaceous raw hydrocarbons (prehnitene, isodurene, materials by the following methods: isomersdiethyl -anddietylmethyl benzole et al).
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