Naphthalate dicarboxylate

The ratio min represents the molar ratio of cl-HQ/BB (m) to added modifier, e.g. terephthalic acid (TA) and 2,6-naphthalic dicarboxylic acid (NDA), ( ). 

Polyethylene naphthalate is a condensation polymer of ethylene glycol and naphthalate dicarboxylate (NDC), with the structure ... 

PEN is the polycondensation prodnct of either dimethyl-2,6-naphthalenedicarhoxylate (2,6-NDC) or naphthalate dicarboxylic acid (2,6-NDA) with ethylene glycol. To date 2,6-NDC is the preferred feedstock in view of the fact that it can be produced more economically in high purity form relative to purified 2,6-NDA. 

Naphthalic acid (naphthalene-1,8-dicarboxylic acid) [518-05-8] M 216.9, m 270°, PKeu(I) 2.1, pKEst(2) 4.5. Crystd from EtOH or aq EtOH. 

The manufacture of polyethylene naphthalate) (PEN) is carried out using dimethyl 2,6-naphthalene dicarboxylate (NDC) and EG and is similar to the manufacture of PET from DMT. The IV after the melt is typically in the range of 0.5... 

The isomeric bibenzoic acids (BBs), would appear to share similar structural features with naphthalene dicarboxylic acid. Like the PET-naphthalate copolymers, PET-bibenzoates have been demonstrated to possess moduli and glass transitions temperatures which increase with increasing levels of rigid comonomer [37-39], Unlike the PET/PEN copolymers, when the symmetrical 4,4 - I f I f monomer is substituted into a PET backbone, virtually every composition of PET-BB is semicrystalline the 2,4- and 3,4- isomers of BB, when... 

Although the superior properties of PEN have been known for many years, the unavailability of the naphthalate monomer has delayed the development of commercial markets, until relatively recently (1995) when the Amoco Chemical Company offered high purity naphthalene-2,6-dimethyl dicarboxylate (NDC) in amounts of up to 60 million pounds per year. This diester is produced by a five-step synthetic route, starting from the readily available compounds, o-xylene and 1,4-butadiene [3], Prior to this, the NDC diester was obtained by extraction of 2,6-dimethylnaphthalene (DMN) from petroleum streams, where it was present in relatively low abundance. Oxidation of DMN to crude 2,6-naphthalene dixcarboxylic (NDA) is conducted by a similar process to that used for conversion of p-xylcnc to purified terephthalic acid (TA), crude NDA is esterified with methanol, and is then distilled to yield high purity NDC. Other companies (e.g. the Mitsubishi Gas Chemical Company) followed Amoco s introduction with lesser amounts of NDC. Teijin [4] has manufactured PEN for many years for its own captive uses in films. 

The modification of PET with naphthalene-2,6-dicarboxylic acid and other additional comonomers is a common measure in bottle manufacturing. Copolyesters based on this compound show excellent barrier properties. Such materials can be produced by addition of the desired amount of comonomer during polymer processing or by blending PET with poly(ethylene naphthalate) (PEN). Additionally, PEN can also be modified by other comonomers such as isophthalic acid (IPA) to improve the flow properties and reduce the melting point. The high price of naphthalene dicarboxylic acid is the reason for its limited application. The overall cost may be reduced by using TPA or IPA as comonomers. 

HEXAHYDRO - 4a,5 - DIMETHYL - 2(3H) - NAPHTHALE-NONE and 2-TRIMETHYLSILYLOXY-1,3-BUTADIENE AS A REACTIVE DIENE DIETHYL trans -4-TRIMETHYL-SILYLOXY-4-CYCLOHEXENE-1,2-DICARBOXYLATE. Sulfur substitution also continues to be of high interest, and three preparations on sulfide synthesis are included BENZYL SULFIDE DIALKYL AND ALKYL ARYL SULFIDES NEOPENTYL PHENYL SULFIDE and UNSYMMETRICAL DIALKYL DISULFIDES sec-BUTYL ISOPROPYL DISULFIDE. 

Other aromatic anhydrides also exhibit parallel behavior upon electrou impact and pyrolysis. The mass spectra of naphthalene-2,3-dicarboxylic anhydride and 1,8-naphthalic anhydride are qualitatively similar (Fields and Meyerson, 1967d) ... 

Polyethylene naphthalate (PEN) polyesters are made from 2,6-naphthalene dicarboxylic acid or 2,6-naphthalene dicarboxylic acid, dimethyl ester. They have higher temperature resistance than amorphous PET and are increasingly used in applications requiring heat sterilisation of the food/drink, although PEN at the moment is significantly more expensive. Table 10.5 lists commonly used substances in polyesters. 

Another important group of bis(naphthalic anhydrides) - the so called bis(ketonaphthalic anhydrides) - was formed by the Fri lel-Crafts reaction between aromatic dicarboxylic acids dichlorides and two-fold molar amounts of acenaphthene and subsequent oxidation of tte obtained bis-acenaphthyls to bis(ketonaphthalic anhydrides) [111-115] according to heme 24. 

On the basis of the chemistry of chloral derivatives, one could suppose that transition from diacenaphthyltrichloroethane to the desired bis(naphthalic anhydride) can be carried out through oxidation of l,l,l-trichloro-2,2-bis(acenaphth-4-yl), subsequent anhydridization of pery-dicarboxylic groups, and dehydrochlorination of 1,1,1-trichloroethane moieties ... 

Poly( 1,3-propylene 2,6-naphthalate) (3GN) is synthesized from dimethyl-2,6-naphthalene dicarboxylate and 1,3-propanediol. The ingredients are reacted under atmospheric pressure under nitrogen in the presence of Ty-zorTM titanium tetraisopropoxide catalyst. The vessel is heated to 240°C over a period of about 330 min. At 188°C, methanol started to evolve. 

L. Alexandrova, A. Cabrera, M. A. Hernandez, M. J. Cruz, M. J. M. Abadie, 0. Manero, and D. Likhatchev. Transesterification in poly(ethylene terephthalate) and poly(ethylene naphthalate 2,6-dicarboxylate) blends Model... 

J. Guastavino, D. Mary, E. Kranse, C. Laurent, and C. Mayoux. On the electrical properties of poly(ethylene naphthalate 2,6-dicarboxylate) biaxial-ly-oriented films. Polyrn. Int, 46(l) 72-76, May 1998. 

Naphthalates Physical properties and handling information for dimethyl 2,6-naphthalene dicarboxylate. Company Data Sheet N-2, BP Sales Administration and Customer Service, 150 West Warrenville Road, 605-CS 3, Naperville, Illinois 60563-8460, November 2004. 

Eastman also have extant intellectual property on a process specifically for the recovery of naphthalene dicarboxylic acid from poly(alkylene naphthalate)s [181],... 

PEN Poly(ethylene 2,6-naphthalene dicarboxylate), or polyethylene naphthalate... 

---