Terephthaloyl chloride

Base Information

• Chemical Name: Terephthaloyl chloride
• CAS No.: 100-20-9
• Deprecated CAS: 106158-15-0,108454-76-8,188665-55-6,1640987-72-9,1927884-58-9,108454-76-8,188665-55-6
• Molecular Formula: C8H4Cl2O2
• Molecular Weight: 203.025
• Hs Code.: DERIVATION
• European Community (EC) Number: 202-829-5
• ICSC Number: 0331
• NSC Number: 41885
• UNII: G247CO9608
• DSSTox Substance ID: DTXSID7026653
• Nikkaji Number: J4.979D
• Wikipedia: Terephthaloyl_chloride
• Wikidata: Q7702072
• ChEMBL ID: CHEMBL1893301
• Mol file: 100-20-9.mol

Synonyms:Terephthaloylchloride (8CI);1,4-Benzenedicarbonyl chloride;1,4-Bis(chlorocarbonyl)benzene;1,4-Di(chlorocarbonyl)benzene;Benzene 1,4-dicarboxylic acid dichloride;NSC41885;Terephthalic acid chloride;Terephthalic acid dichloride;Terephthalicdichloride;Terephthaloyl dichloride;p-Phenylenedicarbonyl dichloride;p-Phthaloyl chloride;p-Phthaloyl dichloride;

Chemical Property of Terephthaloyl chloride

Chemical Property:

• Appearance/Colour: white crystalline flakes
• Vapor Pressure: 0.02 mm Hg ( 25 °C)
• Melting Point: 79-81 °C(lit.)
• Refractive Index: 1.571
• Boiling Point: 266 °C at 760 mmHg
• Flash Point: 143.1 °C
• PSA: 34.14000
• Density: 1.427 g/cm³
• LogP: 2.44460
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: ethanol: 5%, clear
• Water Solubility.: REACTS
• XLogP3: 4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 201.9588348
• Heavy Atom Count: 12
• Complexity: 173

Purity/Quality:

99%min ^*data from raw suppliers

Terephthaloyl Chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C,T
• Hazard Codes: C,T
• Statements: 34-23-35
• Safety Statements: 26-27-36/37/39-45-38-28B

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Toxic Gases & Vapors -> Acid Halides
• Canonical SMILES: C1=CC(=CC=C1C(=O)Cl)C(=O)Cl
• Inhalation Risk: A harmful concentration of airborne particles can be reached quickly when dispersed.
• Effects of Short Term Exposure: The substance is corrosive to the eyes, skin and respiratory tract. Corrosive on ingestion. Exposure could cause asphyxiation due to swelling in the throat. Inhalation may cause lung oedema.
• Uses: Terephthaloyl chloride and Isophthaloyl dichloride have many similar uses as monomers for the synthesis of specialty fibers and as raw materials for polymers such as polyamides and polyesters. Dyemanufacture; synthetic fibers, resins, films; UV absorption; pharmaceuticals; rubber chemicals; cross-linking agent for polyurethanes and polysulfides. Terephthaloyl chloride acts as a monomer with p-phenylenediamine used in the preparation of polymer viz. poly paraphenylene terephthalamide. It is an active component in performance polymers and aramid fibers, which gives flame resistance, chemical resistance, temperature stability, light weight, and very high strength. It is also used as an effective water scavenger, utilized to stabilize isocyanates and urethane prepolymers. Further, it is used in the preparation of liquid crystalline thermosets by thermal cyclotrimerization of dicyanate compounds of ring substituted bis(4-hydroxyphenyl) terepthalates. In addition to this, it is involved in the condensation reaction with difunctional alfa, μ-diaminopolystyrene to get chain-extended polystyrene containing amide bonds along the polymer backbone.

Technology Process of Terephthaloyl chloride

There total 34 articles about Terephthaloyl chloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.2%

phosgene (75-44-5) + terephthalic acid (100-21-0) + N,N-dimethyl-aniline (121-69-7,77733-26-7) → 1,4-benzenedicarboxylic acid dimethyl ester (120-61-6) + terephthaloyl chloride (100-20-9)

Guidance literature:

In dichloromethane;

Reference yield:

1,4-bis(trichloromethyl)benzene (68-36-0) → terephthaloyl chloride (100-20-9)

Guidance literature:

With titanium(IV) oxide;

Reference yield:

4-trichloromethylbenzoyl chloride (14815-86-2) → terephthaloyl chloride (100-20-9)

Guidance literature:

With water; iron(III) chloride; at 120 - 130 ℃;

upstream raw materials:

maleic anhydride

1,4-bis(trichloromethyl)benzene

(E)-3-Ureido-but-2-enoic acid ethyl ester

1,4-benzenedicarboxylic acid dimethyl ester

Downstream raw materials:

N,N'-terephthaloylbis(6-hexanelactam)

7,7'-dioxo-7,7'-p-phenylene-di-heptanoic acid

4-[4-(3-chloro-4-methyl-phenyl)-piperazine-1-carbonyl]-benzoic acid

bis(prop-2-ynyl)benzene-1,4-dicarboxylate

Refernces

• 1、 Cao, Jinlian,Yan, Xiaosheng,He, Wenbin,Li, Xiaorui,Li, Zhao,Mo, Yirong,Liu, Maili,Jiang, Yun-Bao. "C-I···π Halogen Bonding Driven Supramolecular Helix of Bilateral N-Amidothioureas Bearing β-Turns". . p. 6605 - 6610. Retrieved 2017.
• 2、 Muthusamy, Athianna,Balaji, Krishnasamy,Murugavel, Salem Chandrasekaran. "Synthesis, thermal, and photocrosslinking studies of thermotropic liquid crystalline poly(benzylidene-ether)esters containing α,β-unsaturated ketone moiety in the main chain". . p. 1707 - 1715. Retrieved 2013.
• 3、 Arenas, J. F.,Marcos, J. I.,Ramirez, F. J.. "Infrared and Raman spectra of terephthalonitrile and terephthalonitrile-15N2. Force field for out-of-plane vibrations". . p. 1045 - 1052. Retrieved 1988.
• 4、 Kim, Keun-Sik,Kim, Jong-Ho,Seo, Gon. "Phosphazenium chloride catalysts immobilized on SBA-15 mesoporous material and silica gel: New exceptionally active catalysts for the chlorination of organic acids". . p. 372 - 373. Retrieved 2003.
• 5、 Alpers, Torben,Muesmann, Thomas W. T.,Temme, Oliver,Christoffers, Jens. "Aromatic Esters, Carbinols, and Derivatives Thereof with Perfluorohexyl Residues as Alternatives to Perfluoroalkanecarboxylic and -sulfonic Acids". . p. 609 - 617. Retrieved 2017.
• 6、 Palma, Aniello,Serginson, James M.,Barrett, Anthony G.M.. "Synthesis of poly β ketoesters via double acylketene trapping". . p. 674 - 676. Retrieved 2015.
• 7、 Xu, Xiuhui,Webster, Richard D.. "Primary coloured electrochromism of aromatic oxygen and sulfur diesters". . p. 18100 - 18107. Retrieved 2014.
• 8、 Hou, Wen,Lin, Hui,Wang, Zhen-Ya,Banwell, Martin G.,Zeng, Ting,Sun, Ping-Hua,Lin, Jing,Chen, Wei-Min. "Novel bivalent securinine mimetics as topoisomerase I inhibitors". . p. 320 - 328. Retrieved 2017.
• 9、 Yu, Zhiqun,Yao, Hongmiao,Xu, Qilin,Liu, Jiming,Le, Xingmao,Ren, Minna. "Br?nsted acid-catalyzed chlorination of aromatic carboxylic acids". supporting information. p. 685 - 689. Retrieved 2021/04/09.
• 10、 -. "BENZENE 1,4-BIS(BISPHOSPHONIC ACID)-BASED METAL COMPLEXES, METHOD OF SYNTHESIS AND APPLICATIONS THEREOF". Paragraph 0103; 0104. . Retrieved 2021/10/15.