100-21-0

Basic information

• Product Name: Terephthalic acid
• Synonyms: Terephthalic acid 98%;Terephthalic a;Terephthalicacid (7CI,8CI);Terephthalic acid Vetec(TM) reagent grade, 98%;1,4-dicarboxybenzene;1,4-phthalicacid;Acide terephtalique;acideterephtalique
• CAS NO: 100-21-0
• Molecular Formula: C₈H₆O₄
• Molecular Weight: 166.13
• EINECS: 202-830-0
• Product Categories: Pyridines
• Mol File: 100-21-0.mol
• Article Data: 717

Chemical Properties

• Melting Point: 300 °C
• Boiling Point: 214.32°C (rough estimate)
• Flash Point: 260°C
• Appearance: White/Crystalline Powder
• Density: 1,51 g/cm3
• Vapor Pressure: <0.01 mm Hg ( 20 °C)
• Refractive Index: 1.5100 (estimate)
• Storage Temp.: 0-6°C
• Solubility: 15mg/l (experimental)
• PKA: 3.51(at 25℃)
• Water Solubility: slightly soluble in water (0,017 g/L at 25°C)
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
• Merck: 14,9162
• BRN: 1909333
• CAS DataBase Reference: Terephthalic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Terephthalic acid(100-21-0)
• EPA Substance Registry System: Terephthalic acid(100-21-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: WZ0875000
• TSCA: Yes
• Hazardous Substances Data: 100-21-0(Hazardous Substances Data)

Usage

Description

Terephthalic acid is the organic compound with formula C6H4(COOH)2. This colourless solid is a commodity chemical, used principally as a precursor to the polyester PET, used to make clothing and plastic bottles. Several million tones are produced annually. It is one of three isomeric phthalic acids.

Chemical Properties

Terephthalic acid is poorly soluble in water and alcohols, consequently up until around 1970 most crude terephthalic acid was converted to the dimethyl ester for purification. It sublimates when heated.

Chemical Properties

TPA is a white crystalline solid.

Chemical Properties

white powder

History

Terephthalic acid came to prominence through the work of Winfield and Dickson in Britain around 1940. Earlier work by Carothers and coworkers in the United States established the feasibility of producing high molecular weight linear polyesters by reacting diacids with diols, but they used aliphatic diacids and diols. These made polyesters which were unsuitable to be spun into fibers. Winfield and Dickson found that symmetrical aromatic diacids yield high-melting, crystalline, and fiberforming materials; poly(ethylene terephthalate) (PET) has since become the largest volume synthetic fiber.

Uses

Terephthalic acid (TPA) is a high-tonnage chemical, widely used in the production of synthetic materials, notably polyester fibers (poly-(ethylene terephthalate)).

Uses

Terephthalic acid is a benzenepolycarboxylic acid with potential anti-hemorrhagic properties.

Uses

1,4-benzenedicarboxylic acid is mainly used for the production of poly (ethylene terephthalate). Also production of plasticizer dioctyl phthalate (DOTP) and polyester plasticized agents. 1,4-benzenedicarboxylic acid and polyhydric alcohols have a condensation reaction withd iethylene glycol, triethylene glycol, glycerol, propylene glycol, butylene glycol, etc. preparation of the polyester plasticizer.

Definition

ChEBI: A benzenedicarboxylic acid carrying carboxy groups at positions 1 and 4. One of three possible isomers of benzenedicarboxylic acid, the others being phthalic and isophthalic acids.

Application

Virtually the entire world's supply of terephthalic acid and dimethyl terephthalate are consumed as precursors to polyethylene terephthalate (PET). World production in 1970 was around 1.75 million tones. By 2006, global purified terephthalic acid (PTA) demand had exceeded 30 million tonnes. There is a smaller, but nevertheless significant, demand for terephthalic acid in the production of poly butylene terephthalate and several other engineering polymers.

Production Methods

Terephthalic acid is produced by oxidation of p-xylene by oxygen in air: This reaction proceeds through a p-toluic acid intermediate which is then oxidized to terephthalic acid. In p-toluic acid, deactivation of the methyl by the electron withdrawing carboxylic acid group makes the methyl one tenth as reactive as xylene itself, making the second oxidation significantly more difficult . The commercial process utilizes acetic acid as solvent and a catalyst composed of cobalt and manganese salts, with a bromide promoter.

Production Methods

Benzoic acid, phthalic acid and other benzene-carboxylic acids in the form of alkali-metal salts, comprise the chargestock. In a first step, the alkali-metal salts (usually potassium) are converted to terephthalates when heated to a temperature exceeding 350 °C (662 °F). The dried potassium salts (of benzoic acid or o- or isophthalic acid) are heated in anhydrous form to approximately 420 °C (788 °F) in an inert atmosphere (CO2) and in the presence of a catalyst (usually cadmium benzoate, phthalate, oxide, or carbonate). The corresponding zinc compounds also have been used as catalysts. In a following step, the reaction products are dissolved in H2O and the terephthalic acid precipitated out with dilute H2SO4. The yield of terephthalic acid ranges from 95 to 98%.

Preparation

The major commercial route to terephthalic acid which is suitable for the direct preparation of poly(ethylene terephthalate) is from p-xylene: p-Xylene is obtained largely from petroleum sources, being a product of the fractionation of reformed naphthas. The oxidation is carried out in the liquid phase. Typically, air is passed into a solution of p-xylene in acetic acid at about 200℃ and 2 MPa (20 atmospheres) in the presence of a catalyst system containing cobalt and manganese salts and a source of bromide ions. The terephthalic acid produced contains only small amounts of impurities (mainly p-carboxybenzaldehyde), which are readily removed. The acid is dissolved in water at about 2500 e and 5 MPa (50 atmospheres) and treated with hydrogen (which converts the aldehyde to p-toluic acid). The solution is then cooled to 100℃ and pure terephthalic acid crystallizes.

Synthesis Reference(s)

Chemistry Letters, 15, p. 299, 1986Journal of the American Chemical Society, 82, p. 2876, 1960 DOI: 10.1021/ja01496a051The Journal of Organic Chemistry, 44, p. 4727, 1979 DOI: 10.1021/jo00393a063

General Description

White powder.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Terephthalic acid is a carboxylic acid. Terephthalic acid donates hydrogen ions if a base is present to accept them. This "neutralization" generates substantial amounts of heat and produces water plus a salt. Insoluble in water but even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in Terephthalic acid to corrode or dissolve iron, steel, and aluminum parts and containers. May react with cyanide salts to generate gaseous hydrogen cyanide. Will react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by reaction with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. React with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. May initiate polymerization reactions; may catalyze (increase the rate of) chemical reactions.

Fire Hazard

Flash point data for Terephthalic acid are not available. Terephthalic acid is probably combustible.

Flammability and Explosibility

Nonflammable

Safety Profile

Moderately toxic by intravenous and intraperitoneal routes. Mildly toxic by ingestion. An eye irritant, Can explode during preparation. When heated to decomposition it emits acrid smoke and irritating fumes.

Potential Exposure

TPA is used primarily in the production of polyethylene terephthalate polymer for the fabrication of polyester fibers and films. A high-volume production chemical in the United States.

Purification Methods

Purify the acid via the sodium salt which, after crystallisation from water, is re-converted to the acid by acidification with mineral acid. Filter off the solid, wash it with H2O and dry it in a vacuum. The S-benzylisothiuronium salt has m 204o (from aqueous EtOH). [Beilstein 9 IV 3301.]

Incompatibilities

Combustible; dust may form an explosive mixture with air. Compounds of the carboxyl group react with all bases, both inorganic and organic (i.e., amines) releasing substantial heat, water and a salt that may be harmful. Incompatible with arsenic compounds (releases hydrogen cyanide gas), diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides (releasing heat, toxic and possibly flammable gases), thiosulfates and dithionites (releasing hydrogen sulfate and oxides of sulfur). Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides.

Waste Disposal

Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed.

InChI:InChI=1/C8H6O4/c1-9-5-13-18(24,15(9)22)7-11(8-21)6-12-14-17(3,4)20(14,26)16(23)10(2)19(12,13)25/h5-6,10,12-14,16,21,23-26H,7-8H2,1-4H3/t10-,12+,13-,14-,16-,18-,19-,20-/m1/s1

Synthetic route

para-xylene (106-42-3) → terephthalic acid (100-21-0)

Conditions	Yield
With ammonium acetate; water; hydrogen bromide; oxygen; manganese(II) acetate; cobalt(II) diacetate tetrahydrate; 1-n-butyl-3-methylimidazolim bromide; acetic acid at 200℃; under 30753.1 Torr; for 10h; Time; Temperature; Reagent/catalyst; Concentration; Inert atmosphere;	99.9%
With oxovanadium(IV) sulfate; hydrogen bromide; oxygen; acetic acid In water at 100℃; under 750.075 Torr; for 20h;	98%
With oxygen; acetic acid; hydrogen bromide; cobalt(II) acetate; manganese(II) acetate In water at 200℃; under 22502.3 Torr; for 0.05h; Product distribution / selectivity; Inert atmosphere;	98.3%

p-Toluic acid (99-94-5) → terephthalic acid (100-21-0)

Conditions	Yield
With ammonium acetate; water; hydrogen bromide; oxygen; manganese(II) acetate; cobalt(II) diacetate tetrahydrate; 1-n-butyl-3-methylimidazolim bromide; acetic acid; 3-butyl-1-methylimidazolium acetate at 215℃; under 30753.1 Torr; for 3h; Inert atmosphere;	99.1%
With ammonium acetate; water; hydrogen bromide; oxygen; manganese(II) acetate; cobalt(II) diacetate tetrahydrate; 1-n-butyl-3-methylimidazolim bromide; acetic acid; 3-butyl-1-methylimidazolium acetate at 215℃; under 30753.1 Torr; for 3h; Inert atmosphere;	99.1%
With oxovanadium(IV) sulfate; hydrogen bromide; oxygen; acetic acid In water at 100℃; under 750.075 Torr; for 20h;	97%

para-xylene (106-42-3) → terephthalic acid (100-21-0) + 4-Carboxybenzaldehyde (619-66-9)

Conditions	Yield
With air; hydrogen bromide; acetic acid; cobalt(II) acetate; manganese(II) acetate at 180℃; under 25745 Torr; for 0.166667h;	A 98.3% B 1.4%
With 9,10-Dibromoanthracene; acetic acid; cobalt(II) acetate; cerium(III) acetate at 165℃; under 25745 Torr; for 0.166667h;	A 98.2% B 1.1%
With 9,10-Dibromoanthracene; acetic acid; cobalt(II) acetate; manganese(II) acetate at 170℃; under 25745 Torr; for 0.166667h;	A 97.5% B 1.9%

para-xylene (106-42-3) → terephthalic acid (100-21-0) + 4-methyl-benzaldehyde (104-87-0) + 4-Carboxybenzaldehyde (619-66-9) + p-Toluic acid (99-94-5)

Conditions	Yield
With hydrogen bromide; oxygen; acetic acid; cobalt(II) acetate; manganese(II) acetate In water at 190℃; under 16501.7 Torr; for 1h; Product distribution / selectivity;	A 98.1% B 0.2% C 0.4% D 0.4%
With oxygen; acetic acid; palladium diacetate; antimony(III) acetate In water at 182 - 195℃; under 16501.7 - 20929.4 Torr; for 1 - 1.5h; Product distribution / selectivity;	A 50.3% B 7.2% C 6.4% D 6.2%
With hydrogen bromide; oxygen; acetic acid; zirconium oxyacetate; cobalt(II) acetate In water at 190℃; under 16501.7 Torr; for 1h; Product distribution / selectivity;	A 4.9% B 3% C 1.9% D 36.9%

terephthalaldehyde, (623-27-8) → terephthalic acid (100-21-0)

Conditions	Yield
With NADH oxidase and vanillin dehydrogenase 2 co-expressed in Escherichia coli cells In aq. phosphate buffer at 30℃; for 12h; pH=7; Microbiological reaction;	98%
With tris[2-(4,6-difluorophenyl)pyridinato-C2,N]-iridium(III); oxygen In acetonitrile at 20℃; for 24h; Irradiation; Sealed tube; Green chemistry; chemoselective reaction;	95%
With sodium perborate In acetic acid at 45 - 50℃;	93%

4-Carboxybenzaldehyde (619-66-9) → terephthalic acid (100-21-0)

Conditions	Yield
With water; ozone In acetonitrile for 5h; Irradiation;	98%
With NADH oxidase and vanillin dehydrogenase 2 co-expressed in Escherichia coli cells In aq. phosphate buffer at 30℃; for 3h; pH=7; Microbiological reaction;	98%
With C4H11FeMo6NO24(3-)*3C16H36N(1+); water; oxygen; sodium carbonate at 50℃; under 760.051 Torr; for 8h; Green chemistry;	97%

carbon monoxide (201230-82-2) + para-chlorobenzoic acid (74-11-3) → terephthalic acid (100-21-0)

Conditions	Yield
With tetrabutylammomium bromide; dicobalt octacarbonyl In sodium hydroxide at 65℃; for 8h;	98%
With sodium hydroxide; dicobalt octacarbonyl In water at 65℃; under 1471.02 Torr; for 6h; Product distribution; Irradiation;	93.4 % Chromat.

4-methyl-benzaldehyde (104-87-0) → terephthalic acid (100-21-0)

Conditions	Yield
With oxygen; 1-hydroxy-pyrrolidine-2,5-dione; cobalt(II) acetate In acetic acid at 60℃; under 12049.9 Torr; for 1h; Product distribution / selectivity;	98%

carbon monoxide (201230-82-2) + 1.4-dibromobenzene (106-37-6) → terephthalic acid (100-21-0)

Conditions	Yield
With sodium hydroxide; cobalt(II) acetate In ethanol at 30℃; under 1520 Torr; for 4h; Irradiation;	97.1%
With sodium hydroxide; dicobalt octacarbonyl In ethanol; water at 65℃; under 1471.02 Torr; for 4h; Product distribution; Irradiation;	82.5 % Chromat.

p-xylylene glycol (589-29-7) → terephthalic acid (100-21-0)

Conditions	Yield
With diethylene glycol dimethyl ether at 70℃; for 0.583333h; Sonication;	97%
With C24H33IrN4O3; water; sodium hydroxide for 18h; Reflux;	96%
With sodium hypochlorite; water at 25℃; for 0.5h;	94%

Ethyl 4-bromobenzoate (5798-75-4) + carbon monoxide (201230-82-2) → terephthalic acid (100-21-0)

Conditions	Yield
With tetrabutylammomium bromide; dicobalt octacarbonyl In sodium hydroxide; benzene at 65℃; for 1.5h; Irradiation;	97%

4-styrylbenzaldehyde (32555-96-7) → terephthalic acid (100-21-0)

Conditions	Yield
Stage #1: 4-styrylbenzaldehyde With tert.-butylhydroperoxide; iron(III) chloride hexahydrate; sodium hydroxide In water at 80℃; for 10h; Stage #2: With hydrogenchloride In water at 20℃;	97%

3-hydroxymethyl-benzoic acid (3006-96-0) → terephthalic acid (100-21-0)

Conditions	Yield
With C24H33IrN4O3; water; sodium hydroxide for 18h; Reflux;	97%
Multi-step reaction with 2 steps 1: recombinant 5-hydroxymethylfurfural oxidase / aq. phosphate buffer / 4 h / 25 °C / pH 8 / Enzymatic reaction 2: recombinant 5-hydroxymethylfurfural oxidase / aq. phosphate buffer / 1 h / 25 °C / pH 8 / Enzymatic reaction View Scheme
Multi-step reaction with 2 steps 1: recombinant 5-hydroxymethylfurfural oxidase / aq. phosphate buffer / 4 h / 25 °C / pH 8 / Enzymatic reaction 2: recombinant 5-hydroxymethylfurfural oxidase / aq. phosphate buffer / 1 h / 25 °C / pH 8 / Enzymatic reaction View Scheme

diethyl terephthalate (636-09-9) → terephthalic acid (100-21-0)

Conditions	Yield
With PPA at 154℃; for 4.2h;	96%
With potassium carbonate

para-xylene (106-42-3) → terephthalic acid (100-21-0) + p-Toluic acid (99-94-5)

Conditions	Yield
With N-hydroxyphthalimide; oxygen; nitric acid at 110℃; under 760.051 Torr; for 6h; Ionic liquid;	A 96% B 3%
Stage #1: para-xylene With N-hydroxyphthalimide; cobalt(II) phthalocyanine; μ-oxo[manganese(III) tetraphenylporphine]2; oxygen at 120℃; under 3750.38 Torr; Stage #2: With N-hydroxyphthalimide; cobalt(II) phthalocyanine; μ-oxo[manganese(III) tetraphenylporphine]2; oxygen; acetic acid at 232℃; under 16501.7 Torr; for 1.5h; Temperature; Pressure; Reagent/catalyst;	A 90% B 9.7%
With chromium(VI) oxide; periodic acid In acetonitrile at 20℃; for 1h;	A 6% B 86%

polyethylene terephthalate → terephthalic acid (100-21-0)

Conditions	Yield
Stage #1: polyethylene terephthalate With sodium hydroxide In octanol at 183℃; for 0.25h; Heating / reflux; Stage #2: With hydrogenchloride In water Product distribution / selectivity;	96%
Stage #1: polyethylene terephthalate With sodium hydroxide In butan-1-ol at 108℃; for 0.25h; Stage #2: With sulfuric acid pH=2; Product distribution / selectivity;	96%
Stage #1: polyethylene terephthalate With sodium hydroxide In pentan-1-ol at 124℃; for 0.166667h; Stage #2: With sulfuric acid pH=2; Product distribution / selectivity;	96%

polyethylene terephthalate → terephthalic acid (100-21-0) + ethylene glycol (107-21-1)

Conditions	Yield
Stage #1: polyethylene terephthalate With sodium hydroxide In propan-1-ol at 89℃; for 0.25h; Stage #2: With hydrogenchloride In propan-1-ol; water Product distribution / selectivity;	A 96% B n/a

5-(1-methyl-3,4,5,6,7,7-hexachloro-norborn-4-ene-1)-isophthalic acid dichloride + terephthaloyl chloride (100-20-9) → terephthalic acid (100-21-0)

Conditions	Yield
In 1,2-dimethoxyethane; ethylene glycol	96%

4-Methylbenzyl alcohol (589-18-4) → terephthalic acid (100-21-0)

Conditions	Yield
With carbon dioxide; oxygen; 1-hydroxy-pyrrolidine-2,5-dione; cobalt(II) acetate In acetic acid at 22℃; under 44734.5 Torr; for 24h; Product distribution / selectivity;	96%

acetic acid (64-19-7) + p-Toluic acid (99-94-5) → terephthalic acid (100-21-0) + 3-hydroxymethyl-benzoic acid (3006-96-0) + p-acetoxymethyl benzoic acid (15561-46-3) + 4-Carboxybenzaldehyde (619-66-9)

Conditions	Yield
With N-hydroxyphthalimide; air; cobalt(II) acetate; manganese(II) acetate at 150℃; under 22800 Torr; for 3h;	A 95% B n/a C n/a D n/a

carbon dioxide (124-38-9) + 1.4-dibromobenzene (106-37-6) → terephthalic acid (100-21-0)

Conditions	Yield
With C26H30B10Cl2P2Pd In toluene at 60℃; under 760.051 Torr; for 8h;	95%
Stage #1: carbon dioxide With o-phenylenebis(diphenylphosphine); copper(II) acetate monohydrate In 1,4-dioxane at 65℃; for 0.333333h; Schlenk technique; Stage #2: 1.4-dibromobenzene With palladium diacetate; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane; toluene at 100℃; for 8h; Schlenk technique; Sealed tube;	93%
Stage #1: carbon dioxide With o-phenylenebis(diphenylphosphine); copper(II) acetate monohydrate In 1,4-dioxane at 65℃; for 0.416667h; Schlenk technique; Stage #2: 1.4-dibromobenzene With palladium diacetate; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane; toluene at 100℃; for 20h; Schlenk technique;	93%

1,4-C6H4(COFp)2 (119923-98-7) → dicarbonylcyclopentadienyliodoiron(II) (12078-28-3, 38979-86-1) + terephthalic acid (100-21-0)

Conditions	Yield
With iodine In tetrahydrofuran (N2), reaction for 20 min; IR, NMR;	A 77% B 94%

1,4-C6H4(COFp)2 (119923-98-7) → dicarbonylcyclopentadienylbromoiron(II) + terephthalic acid (100-21-0)

Conditions	Yield
With bromine In tetrahydrofuran (N2), reaction for 20 min; IR, NMR;	A 85% B 94%

carbon monoxide (201230-82-2) + para-diiodobenzene (624-38-4) → terephthalic acid (100-21-0)

Conditions	Yield
With potassium hydroxide; amphiphilic resin-supported phosphine-palladium; water at 25℃; under 760 Torr; for 12h; hydroxycarbonylation;	93%

(3-amino-4-ethylphenyl)methanol (5129-22-6) → terephthalic acid (100-21-0)

Conditions	Yield
Stage #1: (3-amino-4-ethylphenyl)methanol With 2,5-dimethyl-2,5-hexanediol at 67℃; for 2.83333h; Stage #2: With bis(cyclopentadienyl)diphenyltitanium(IV) at 86℃; for 1.5h; Temperature;	93%

para-xylene (106-42-3) → terephthalic acid (100-21-0) + anthraquinone-2,6-dicarboxylic acid (42946-19-0)

Conditions	Yield
With oxygen; manganese(II) acetate; cobalt(II) bromide In water; acetic acid at 175 - 220℃; under 11400.8 Torr; for 1h; Product distribution / selectivity;	A 92.4% B n/a

1,3,5-triazin-2,4,6[1H,3H,5H]-trion-1N,3N,5N-tri-O-yl acetate (558480-54-9) + cobalt (II) acetate·4 H2O + manganese (II) acetate·4 H2O → terephthalic acid (100-21-0)

Conditions	Yield
With nitrogen; acetic acid In titanium; para-xylene	92%

para-methylacetophenone (122-00-9) → terephthalic acid (100-21-0)

Conditions	Yield
With oxygen; manganese (II) acetate tetrahydrate; cobalt(II) diacetate tetrahydrate; 1N,3N,5N-trihydroxy-1,3,5-triazin-2,4,6[1H,3H,5H]-trione In acetic acid at 120℃; under 760.051 Torr; for 15h;	91%
With nitric acid nachfolgend Oxydation mit Permanganat in verduennter Natronlauge;
With sodium hydroxide; chlorine; 1,2,3-trichlorobenzene at 150 - 200℃; anschliessendes Erhitzen mit wss. Natriumhypochlorit-Loesung;

4-ethenylbenzoic acid (1075-49-6) → terephthalic acid (100-21-0)

Conditions	Yield
With Oxone; 2-iodo-3,4,5,6-tetramethylbenzoic acid In water; acetonitrile for 22h;	91%
With Oxone In water; acetonitrile for 19h; Reflux;	77%

methanol (67-56-1) + terephthalic acid (100-21-0) → 1,4-benzenedicarboxylic acid dimethyl ester (120-61-6)

Conditions	Yield
Stage #1: methanol; terephthalic acid for 0.5h; Reflux; Inert atmosphere; Stage #2: With thionyl chloride for 10h; Reflux; Inert atmosphere;	100%
With thionyl chloride Heating;	99%
Stage #1: methanol; terephthalic acid for 0.5h; Reflux; Stage #2: With thionyl chloride for 12h; Reflux;	99%

terephthalic acid (100-21-0) → terephthaloyl chloride (100-20-9)

Conditions	Yield
With thionyl chloride for 2h; Reflux;	100%
With aluminum (III) chloride; Methyltrichlorosilane In tetrachloromethane at 70℃; for 13h; Temperature; Reagent/catalyst;	99.13%
With thionyl chloride for 5h; Reflux;	98%

1-adamantyl bromomethyl ketone (5122-82-7) + terephthalic acid (100-21-0) → Terephthalic acid bis-(2-adamantan-1-yl-2-oxo-ethyl) ester (123426-29-9)

Conditions	Yield
With triethylamine In acetone for 6h; Heating;	100%

terephthalic acid (100-21-0) + 1-dodecylbromide (143-15-7) → bis-dodecyl benzene-1,4-dicarboxylate (18749-84-3)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In benzene for 18h; Esterification; Heating;	100%

phosgene (75-44-5) + terephthalic acid (100-21-0) → 1,4-benzenedicarboxylic acid dimethyl ester (120-61-6)

Conditions	Yield
With pyridine In dichloromethane	100%

[(η(5)-C5H5)2Co][OH] + terephthalic acid (100-21-0) → 2((C5H5)2Co)(1+)*(C6H4(COO)2)(2-)*6H2O = [(C5H5)2Co]2[(C6H4(COO)2)]*6H2O

Conditions	Yield
In water mixing; filtn., solvent evpn.;	100%

bis(benzene)chromium hydroxide + terephthalic acid (100-21-0) → 2((C6H6)2Cr)(1+)*(C6H4(COO)2)(2-)*6H2O = [(C6H6)2Cr]2[(C6H4(COO)2)]*6H2O

Conditions	Yield
In water mixing; filtn., solvent evpn.;	100%

terephthalic acid (100-21-0) + 3-(4-piperidinyl)-1H-indole (17403-09-7) → 1,4-phenylenebis((4-(1H-indol-3-yl)piperidin-1-yl)methanone)

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;	100%

terephthalic acid (100-21-0) → barium terephthalate (46190-30-1)

Conditions	Yield
With barium(II) chloride dihydrate; potassium hydroxide In water	100%
Stage #1: terephthalic acid With barium(II) nitrate In methanol for 1h; Stage #2: With pyridine for 3h; Reagent/catalyst; Solvent;

terephthalic acid (100-21-0) + 1,5-diamino-3-azapentane (111-40-0) → C16H24N6

Conditions	Yield
at 170 - 270℃;	100%

terephthalic acid (100-21-0) + (3S,4S)-N3,N4-dihexylpyrrolidine-3,4-dicarboxamide hydrochloride → (3S,3’S,4S,4’S)-1,1’-terephthaloylbis(N3,N4-dihexylpyrrolidine-3,4-dicarboxamide)

Conditions	Yield
With 2,6-dimethylpyridine; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 0 - 25℃; for 4.5h;	100%
Stage #1: terephthalic acid; (3S,4S)-N3,N4-dihexylpyrrolidine-3,4-dicarboxamide hydrochloride With 2,6-dimethylpyridine; 1-hydroxy-7-aza-benzotriazole In dichloromethane; N,N-dimethyl-formamide at 0℃; for 0.0833333h; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 4.5h;	84%

terephthalic acid (100-21-0) + 3CO3(2-)*2Eu(3+)*4H2O + 3CO3(2-)*2Gd(3+)*4H2O → (Eu0.5Gd0.5)2(benzene-1,4-dicarboxylate)3(H2O)4

Conditions	Yield
In neat (no solvent, solid phase) for 2h; Milling; Inert atmosphere;	100%

2Sm(3+)*3CO3(2-)*4H2O=Sm2(CO3)3*4H2O + terephthalic acid (100-21-0) + 3CO3(2-)*2Gd(3+)*4H2O → (Sm0.5Gd0.5)2(benzene-1,4-dicarboxylate)3(H2O)4

Conditions	Yield
In neat (no solvent, solid phase) for 2h; Milling; Inert atmosphere;	100%

2Tb(3+)*3CO3(2-)*6H2O=Tb2(CO3)3*6H2O + terephthalic acid (100-21-0) + 3CO3(2-)*2Gd(3+)*4H2O → (Tb0.5Gd0.5)2(benzene-1,4-dicarboxylate)3(H2O)4

Conditions	Yield
In neat (no solvent, solid phase) for 2h; Milling; Inert atmosphere;	100%

[2,2]bipyridinyl (366-18-7) + zinc(II) nitrate hexahydrate + terephthalic acid (100-21-0) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → {[Zn(1,4-benzenedicarboxylato)(2,2'-bipyridine)]·N,N-dimethylformamide}n

Conditions	Yield
at 80℃; for 96 - 168h;	100%

terephthalic acid (100-21-0) → cyclohexane-1,4-dicarboxylic acid (619-81-8, 619-82-9, 1076-97-7)

Conditions	Yield
With ammonium hydroxide; 1% Pd/C; hydrogen at 90℃; Reagent/catalyst; Temperature;	99.9%
With hydrogen In water at 200℃; under 30003 Torr; for 3h; Reagent/catalyst;	98.7%
With hydrogen In water at 140℃; under 51716.2 Torr; for 6h; Solvent; Temperature; Autoclave;	69.8%

propan-1-ol (71-23-8) + terephthalic acid (100-21-0) → di-n-butyl terephthalate (1962-75-0)

Conditions	Yield
Stage #1: propan-1-ol; terephthalic acid With titanium(IV) isopropylate at 180℃; under 4560.31 Torr; for 3h; Inert atmosphere; Stage #2: propan-1-ol With toluene-4-sulfonic acid at 200℃; under 4560.31 Torr; for 6h; Reagent/catalyst; Inert atmosphere;	99.6%

2-Ethylhexyl alcohol (104-76-7) + terephthalic acid (100-21-0) → di(2-ethylhexyl)terephthalate (6422-86-2)

Conditions	Yield
With phenol and titanium tetraisopropoxide resin at 200℃; for 4h; Reagent/catalyst; Dean-Stark; Inert atmosphere;	99.5%
With titanium(IV) isopropylate at 170 - 200℃; Inert atmosphere; Large scale;	99%
With titanium(IV) isopropylate at 170 - 220℃; under 760.051 Torr; for 4.5h; Inert atmosphere; Large scale;	99%

propan-1-ol (71-23-8) + terephthalic acid (100-21-0) → terephthalic acid dipropyl ester (1962-74-9)

Conditions	Yield
With thionyl chloride Heating;	99%
With sulfuric acid
With sulfuric acid Reflux;

terephthalic acid (100-21-0) + N-[1-(4-Amino-phenyl)-1-phenyl-meth-(E)-ylidene]-benzene-1,4-diamine → Polymer; Monomer(s): OPA, terephthalic acid;

Conditions	Yield
With pyridine; 1-methyl-pyrrolidin-2-one; lithium chloride; triphenyl phosphite at 80℃;	99%

terephthalic acid (100-21-0) + 4,4'‑diamino‑4''‑methoxytriphenylamine (134248-82-1) → polymer, inherent viscosity 0.79 dl/g, softening temp. 248 deg C; monomer(s): 4,4'-diamino-4''-methoxytriphenylamine; terephthalic acid

Conditions	Yield
With pyridine; triphenyl phosphite; calcium chloride In 1-methyl-pyrrolidin-2-one at 105℃; for 3h;	99%

vanadocene + terephthalic acid (100-21-0) → V(3+)*C5H5(1-)*2OOCC6H4COOH(1-)=(C5H5)V(OCOC6H4COOH)2

Conditions	Yield
In toluene byproducts: cyclopentadiene; Ar atmosphere; 20 h at 120°C; ppt. was filtered off, washed with toluene and ether, and dried; elem. anal.;	99%

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + ammonium sulfate + terephthalic acid (100-21-0) + zinc(II) oxide → [(zinc)2(terephthalate)2(1,4-diazabicyclo[2.2.2]octane)]*(x)(NH4)2SO4 [Zn2(C6H4(COO)2)2(N2(C2H4)3)]*99(NH4)2SO4, hexagonal

Conditions	Yield
With DMF In solid mixt. of ZnO, C6H4(COOH)2, N2(C2H4)3 (in stoich. ratio 1:1:0.5), (NH4)2SO4 (12% weight fraction of solid reagents) and DMF ground at room temp. for 30 min; detd. by XRD;	99%

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + terephthalic acid (100-21-0) + sodium sulfate (7757-82-6) + zinc(II) oxide → [(zinc)2(terephthalate)2(1,4-diazabicyclo[2.2.2]octane)]*(x)Na2SO4 [Zn2(C6H4(COO)2)2(N2(C2H4)3)]*99Na2SO4, hexagonal

Conditions	Yield
With DMF In solid mixt. of ZnO, C6H4(COOH)2, N2(C2H4)3 (in stoich. ratio 1:1:0.5), Na2SO4 (12% weight fraction of solid reagents) and DMF ground at room temp. for30 min; detd. by XRD;	99%

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + potassium sulfate + terephthalic acid (100-21-0) + zinc(II) oxide → [(zinc)2(terephthalate)2(1,4-diazabicyclo[2.2.2]octane)]*(x)K2SO4 [Zn2(C6H4(COO)2)2(N2(C2H4)3)]*99K2SO4, hexagonal

Conditions	Yield
With DMF In solid mixt. of ZnO, C6H4(COOH)2, N2(C2H4)3 (in stoich. ratio 1:1:0.5), K2SO4 (12% weight fraction of solid reagents) and DMF ground at room temp. for 30 min; detd. by XRD;	99%

terephthalic acid (100-21-0) + isopropyl bromide (75-26-3) → terephthalic acid diisopropyl ester (6422-84-0)

Conditions	Yield
With triethylamine at 60℃; for 2h; Inert atmosphere; Ionic liquid;	99%

terephthalic acid (100-21-0) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) + zinc(II) oxide → [Zn(1,4-benzenedicarboxylate)(H2O)]*DMF (213275-65-1)

Conditions	Yield
With H2O In neat (no solvent) grinding C6H4(COOH)2 with ZnO and DMF (with H2O content of 10 % v/v) for30 min; detd. by XRD;	99%
In neat (no solvent) grinding C6H4(COOH)2 with ZnO and DMF for 20 min; H. Li et al., J. Am. Chem. Soc. 1998, 120, 8571; detd. by XRD;

Upstream product

• 19513-05-4 Manganese triacetate dihydrate 
• 106-42-3 1,4-Dimethylbenzene 
• 619-66-9 4-Formylbenzoic acid 
• 638-38-0 MANGANESE(II) ACETATE 
• 71-48-7 Cobalt acetate 

Downstream Products

• 109-16-0 Triethylene glycol dimethacrylate 
• 25038-59-9 POLY(ETHYLENE TEREPHTHALATE) 
• 6422-86-2 Dioctyl terephthalate 
• 26062-94-2 POLY(1,4-BUTYLENE TEREPHTHALATE) 
• 100-20-9 Terephthaloyl chloride 
• 16043-40-6 Pigment Red 122 
• 521-31-3 3-Aminophthalhydrazide 
• 120-61-6 DIMETHYL TEREPHTHALATE 

Recommend Products

• 959-26-2  Bis(2-Hydroxyethyl)terephthalat 
• 75-21-8  oxirane 
• 1962-74-9  terephthalic acid dipropyl ester 
• 71-23-8  propan-1-ol 
• 586-76-5  4-Bromobenzoic acid 
• 109-72-8  n-butyllithium 
• 106-37-6  1.4-dibromobenzene 
• 619-58-9  4-iodobenzoic acid 
• 151-50-8  potassium cyanide 
• 14815-86-2  4-trichloromethylbenzoyl chloride 
• 636-78-2  4-sulphobenzoic acid 
• 141-53-7  sodium formate 
• 619-65-8  4-cyanobenzoic Acid 
• 104-85-8  para-methylbenzonitrile 

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