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100-21-0 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

Different sources of media describe the Chemical Properties of 100-21-0 differently. You can refer to the following data:
1. 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.
2. TPA is a white crystalline solid.
3. 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

Different sources of media describe the Uses of 100-21-0 differently. You can refer to the following data:
1. Terephthalic acid (TPA) is a high-tonnage chemical, widely used in the production of synthetic materials, notably polyester fibers (poly-(ethylene terephthalate)).
2. Terephthalic acid is a benzenepolycarboxylic acid with potential anti-hemorrhagic properties.
3. 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

Different sources of media describe the Production Methods of 100-21-0 differently. You can refer to the following data:
1. 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.
2. 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.

Check Digit Verification of cas no

The CAS Registry Mumber 100-21-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 0 respectively; the second part has 2 digits, 2 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 100-21:
(5*1)+(4*0)+(3*0)+(2*2)+(1*1)=10
10 % 10 = 0
So 100-21-0 is a valid CAS Registry Number.
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

100-21-0 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (A12527)  Terephthalic acid, 98+%   

  • 100-21-0

  • 250g

  • 201.0CNY

  • Detail
  • Alfa Aesar

  • (A12527)  Terephthalic acid, 98+%   

  • 100-21-0

  • 500g

  • 227.0CNY

  • Detail
  • Alfa Aesar

  • (A12527)  Terephthalic acid, 98+%   

  • 100-21-0

  • 10000g

  • 3646.0CNY

  • Detail
  • Sigma-Aldrich

  • (40818)  Terephthalicacid  analytical standard

  • 100-21-0

  • 40818-100MG

  • 458.64CNY

  • Detail
  • Aldrich

  • (185361)  Terephthalicacid  98%

  • 100-21-0

  • 185361-5G

  • 273.78CNY

  • Detail
  • Aldrich

  • (185361)  Terephthalicacid  98%

  • 100-21-0

  • 185361-100G

  • 329.94CNY

  • Detail
  • Aldrich

  • (185361)  Terephthalicacid  98%

  • 100-21-0

  • 185361-500G

  • 366.21CNY

  • Detail
  • Vetec

  • (V900524)  Terephthalicacid  Vetec reagent grade, 98%

  • 100-21-0

  • V900524-500G

  • 159.12CNY

  • Detail

100-21-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name terephthalic acid

1.2 Other means of identification

Product number -
Other names TEREPHTHALIC ACID FOR SYNTHESIS

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:100-21-0 SDS

100-21-0Synthetic route

para-xylene
106-42-3

para-xylene

terephthalic acid
100-21-0

terephthalic acid

Conditions
ConditionsYield
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

p-Toluic acid

terephthalic acid
100-21-0

terephthalic acid

Conditions
ConditionsYield
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

para-xylene

A

terephthalic acid
100-21-0

terephthalic acid

B

4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

Conditions
ConditionsYield
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

para-xylene

A

terephthalic acid
100-21-0

terephthalic acid

B

4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

C

4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

D

p-Toluic acid
99-94-5

p-Toluic acid

Conditions
ConditionsYield
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

terephthalaldehyde,

terephthalic acid
100-21-0

terephthalic acid

Conditions
ConditionsYield
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

4-Carboxybenzaldehyde

terephthalic acid
100-21-0

terephthalic acid

Conditions
ConditionsYield
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

carbon monoxide

para-chlorobenzoic acid
74-11-3

para-chlorobenzoic acid

terephthalic acid
100-21-0

terephthalic acid

Conditions
ConditionsYield
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

4-methyl-benzaldehyde

terephthalic acid
100-21-0

terephthalic acid

Conditions
ConditionsYield
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

carbon monoxide

1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

terephthalic acid
100-21-0

terephthalic acid

Conditions
ConditionsYield
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

p-xylylene glycol

terephthalic acid
100-21-0

terephthalic acid

Conditions
ConditionsYield
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

Ethyl 4-bromobenzoate

carbon monoxide
201230-82-2

carbon monoxide

terephthalic acid
100-21-0

terephthalic acid

Conditions
ConditionsYield
With tetrabutylammomium bromide; dicobalt octacarbonyl In sodium hydroxide; benzene at 65℃; for 1.5h; Irradiation;97%
4-styrylbenzaldehyde
32555-96-7

4-styrylbenzaldehyde

terephthalic acid
100-21-0

terephthalic acid

Conditions
ConditionsYield
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

3-hydroxymethyl-benzoic acid

terephthalic acid
100-21-0

terephthalic acid

Conditions
ConditionsYield
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

diethyl terephthalate

terephthalic acid
100-21-0

terephthalic acid

Conditions
ConditionsYield
With PPA at 154℃; for 4.2h;96%
With potassium carbonate
para-xylene
106-42-3

para-xylene

A

terephthalic acid
100-21-0

terephthalic acid

B

p-Toluic acid
99-94-5

p-Toluic acid

Conditions
ConditionsYield
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

polyethylene terephthalate

terephthalic acid
100-21-0

terephthalic acid

Conditions
ConditionsYield
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

polyethylene terephthalate

A

terephthalic acid
100-21-0

terephthalic acid

B

ethylene glycol
107-21-1

ethylene glycol

Conditions
ConditionsYield
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

5-(1-methyl-3,4,5,6,7,7-hexachloro-norborn-4-ene-1)-isophthalic acid dichloride

terephthaloyl chloride
100-20-9

terephthaloyl chloride

terephthalic acid
100-21-0

terephthalic acid

Conditions
ConditionsYield
In 1,2-dimethoxyethane; ethylene glycol96%
4-Methylbenzyl alcohol
589-18-4

4-Methylbenzyl alcohol

terephthalic acid
100-21-0

terephthalic acid

Conditions
ConditionsYield
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

acetic acid

p-Toluic acid
99-94-5

p-Toluic acid

A

terephthalic acid
100-21-0

terephthalic acid

B

3-hydroxymethyl-benzoic acid
3006-96-0

3-hydroxymethyl-benzoic acid

C

p-acetoxymethyl benzoic acid
15561-46-3

p-acetoxymethyl benzoic acid

D

4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

Conditions
ConditionsYield
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

carbon dioxide

1.4-dibromobenzene
106-37-6

1.4-dibromobenzene

terephthalic acid
100-21-0

terephthalic acid

Conditions
ConditionsYield
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

1,4-C6H4(COFp)2

A

dicarbonylcyclopentadienyliodoiron(II)
12078-28-3, 38979-86-1

dicarbonylcyclopentadienyliodoiron(II)

B

terephthalic acid
100-21-0

terephthalic acid

Conditions
ConditionsYield
With iodine In tetrahydrofuran (N2), reaction for 20 min; IR, NMR;A 77%
B 94%
1,4-C6H4(COFp)2
119923-98-7

1,4-C6H4(COFp)2

A

dicarbonylcyclopentadienylbromoiron(II)

dicarbonylcyclopentadienylbromoiron(II)

B

terephthalic acid
100-21-0

terephthalic acid

Conditions
ConditionsYield
With bromine In tetrahydrofuran (N2), reaction for 20 min; IR, NMR;A 85%
B 94%
carbon monoxide
201230-82-2

carbon monoxide

para-diiodobenzene
624-38-4

para-diiodobenzene

terephthalic acid
100-21-0

terephthalic acid

Conditions
ConditionsYield
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

(3-amino-4-ethylphenyl)methanol

terephthalic acid
100-21-0

terephthalic acid

Conditions
ConditionsYield
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

para-xylene

A

terephthalic acid
100-21-0

terephthalic acid

B

anthraquinone-2,6-dicarboxylic acid
42946-19-0

anthraquinone-2,6-dicarboxylic acid

Conditions
ConditionsYield
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

1,3,5-triazin-2,4,6[1H,3H,5H]-trion-1N,3N,5N-tri-O-yl acetate

cobalt (II) acetate·4 H2O

cobalt (II) acetate·4 H2O

manganese (II) acetate·4 H2O

manganese (II) acetate·4 H2O

terephthalic acid
100-21-0

terephthalic acid

Conditions
ConditionsYield
With nitrogen; acetic acid In titanium; para-xylene92%
para-methylacetophenone
122-00-9

para-methylacetophenone

terephthalic acid
100-21-0

terephthalic acid

Conditions
ConditionsYield
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

4-ethenylbenzoic acid

terephthalic acid
100-21-0

terephthalic acid

Conditions
ConditionsYield
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

methanol

terephthalic acid
100-21-0

terephthalic acid

1,4-benzenedicarboxylic acid dimethyl ester
120-61-6

1,4-benzenedicarboxylic acid dimethyl ester

Conditions
ConditionsYield
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

terephthalic acid

terephthaloyl chloride
100-20-9

terephthaloyl chloride

Conditions
ConditionsYield
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

1-adamantyl bromomethyl ketone

terephthalic acid
100-21-0

terephthalic acid

Terephthalic acid bis-(2-adamantan-1-yl-2-oxo-ethyl) ester
123426-29-9

Terephthalic acid bis-(2-adamantan-1-yl-2-oxo-ethyl) ester

Conditions
ConditionsYield
With triethylamine In acetone for 6h; Heating;100%
terephthalic acid
100-21-0

terephthalic acid

1-dodecylbromide
143-15-7

1-dodecylbromide

bis-dodecyl benzene-1,4-dicarboxylate
18749-84-3

bis-dodecyl benzene-1,4-dicarboxylate

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In benzene for 18h; Esterification; Heating;100%
phosgene
75-44-5

phosgene

terephthalic acid
100-21-0

terephthalic acid

1,4-benzenedicarboxylic acid dimethyl ester
120-61-6

1,4-benzenedicarboxylic acid dimethyl ester

Conditions
ConditionsYield
With pyridine In dichloromethane100%
[(η(5)-C5H5)2Co][OH]

[(η(5)-C5H5)2Co][OH]

terephthalic acid
100-21-0

terephthalic acid

2((C5H5)2Co)(1+)*(C6H4(COO)2)(2-)*6H2O = [(C5H5)2Co]2[(C6H4(COO)2)]*6H2O

2((C5H5)2Co)(1+)*(C6H4(COO)2)(2-)*6H2O = [(C5H5)2Co]2[(C6H4(COO)2)]*6H2O

Conditions
ConditionsYield
In water mixing; filtn., solvent evpn.;100%
bis(benzene)chromium hydroxide

bis(benzene)chromium hydroxide

terephthalic acid
100-21-0

terephthalic acid

2((C6H6)2Cr)(1+)*(C6H4(COO)2)(2-)*6H2O = [(C6H6)2Cr]2[(C6H4(COO)2)]*6H2O

2((C6H6)2Cr)(1+)*(C6H4(COO)2)(2-)*6H2O = [(C6H6)2Cr]2[(C6H4(COO)2)]*6H2O

Conditions
ConditionsYield
In water mixing; filtn., solvent evpn.;100%
terephthalic acid
100-21-0

terephthalic acid

3-(4-piperidinyl)-1H-indole
17403-09-7

3-(4-piperidinyl)-1H-indole

1,4-phenylenebis((4-(1H-indol-3-yl)piperidin-1-yl)methanone)

1,4-phenylenebis((4-(1H-indol-3-yl)piperidin-1-yl)methanone)

Conditions
ConditionsYield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;100%
terephthalic acid
100-21-0

terephthalic acid

barium terephthalate
46190-30-1

barium terephthalate

Conditions
ConditionsYield
With barium(II) chloride dihydrate; potassium hydroxide In water100%
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

terephthalic acid

1,5-diamino-3-azapentane
111-40-0

1,5-diamino-3-azapentane

C16H24N6

C16H24N6

Conditions
ConditionsYield
at 170 - 270℃;100%
terephthalic acid
100-21-0

terephthalic acid

(3S,4S)-N3,N4-dihexylpyrrolidine-3,4-dicarboxamide hydrochloride

(3S,4S)-N3,N4-dihexylpyrrolidine-3,4-dicarboxamide hydrochloride

(3S,3’S,4S,4’S)-1,1’-terephthaloylbis(N3,N4-dihexylpyrrolidine-3,4-dicarboxamide)

(3S,3’S,4S,4’S)-1,1’-terephthaloylbis(N3,N4-dihexylpyrrolidine-3,4-dicarboxamide)

Conditions
ConditionsYield
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

terephthalic acid

3CO3(2-)*2Eu(3+)*4H2O

3CO3(2-)*2Eu(3+)*4H2O

3CO3(2-)*2Gd(3+)*4H2O

3CO3(2-)*2Gd(3+)*4H2O

(Eu0.5Gd0.5)2(benzene-1,4-dicarboxylate)3(H2O)4

(Eu0.5Gd0.5)2(benzene-1,4-dicarboxylate)3(H2O)4

Conditions
ConditionsYield
In neat (no solvent, solid phase) for 2h; Milling; Inert atmosphere;100%
2Sm(3+)*3CO3(2-)*4H2O=Sm2(CO3)3*4H2O

2Sm(3+)*3CO3(2-)*4H2O=Sm2(CO3)3*4H2O

terephthalic acid
100-21-0

terephthalic acid

3CO3(2-)*2Gd(3+)*4H2O

3CO3(2-)*2Gd(3+)*4H2O

(Sm0.5Gd0.5)2(benzene-1,4-dicarboxylate)3(H2O)4

(Sm0.5Gd0.5)2(benzene-1,4-dicarboxylate)3(H2O)4

Conditions
ConditionsYield
In neat (no solvent, solid phase) for 2h; Milling; Inert atmosphere;100%
2Tb(3+)*3CO3(2-)*6H2O=Tb2(CO3)3*6H2O

2Tb(3+)*3CO3(2-)*6H2O=Tb2(CO3)3*6H2O

terephthalic acid
100-21-0

terephthalic acid

3CO3(2-)*2Gd(3+)*4H2O

3CO3(2-)*2Gd(3+)*4H2O

(Tb0.5Gd0.5)2(benzene-1,4-dicarboxylate)3(H2O)4

(Tb0.5Gd0.5)2(benzene-1,4-dicarboxylate)3(H2O)4

Conditions
ConditionsYield
In neat (no solvent, solid phase) for 2h; Milling; Inert atmosphere;100%
[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

zinc(II) nitrate hexahydrate

zinc(II) nitrate hexahydrate

terephthalic acid
100-21-0

terephthalic acid

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

{[Zn(1,4-benzenedicarboxylato)(2,2'-bipyridine)]·N,N-dimethylformamide}n

{[Zn(1,4-benzenedicarboxylato)(2,2'-bipyridine)]·N,N-dimethylformamide}n

Conditions
ConditionsYield
at 80℃; for 96 - 168h;100%
terephthalic acid
100-21-0

terephthalic acid

cyclohexane-1,4-dicarboxylic acid
619-81-8, 619-82-9, 1076-97-7

cyclohexane-1,4-dicarboxylic acid

Conditions
ConditionsYield
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

propan-1-ol

terephthalic acid
100-21-0

terephthalic acid

di-n-butyl terephthalate
1962-75-0

di-n-butyl terephthalate

Conditions
ConditionsYield
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

2-Ethylhexyl alcohol

terephthalic acid
100-21-0

terephthalic acid

di(2-ethylhexyl)terephthalate
6422-86-2

di(2-ethylhexyl)terephthalate

Conditions
ConditionsYield
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

propan-1-ol

terephthalic acid
100-21-0

terephthalic acid

terephthalic acid dipropyl ester
1962-74-9

terephthalic acid dipropyl ester

Conditions
ConditionsYield
With thionyl chloride Heating;99%
With sulfuric acid
With sulfuric acid Reflux;
terephthalic acid
100-21-0

terephthalic acid

N-[1-(4-Amino-phenyl)-1-phenyl-meth-(E)-ylidene]-benzene-1,4-diamine

N-[1-(4-Amino-phenyl)-1-phenyl-meth-(E)-ylidene]-benzene-1,4-diamine

Polymer; Monomer(s): OPA, terephthalic acid;

Polymer; Monomer(s): OPA, terephthalic acid;

Conditions
ConditionsYield
With pyridine; 1-methyl-pyrrolidin-2-one; lithium chloride; triphenyl phosphite at 80℃;99%
terephthalic acid
100-21-0

terephthalic acid

4,4'‑diamino‑4''‑methoxytriphenylamine
134248-82-1

4,4'‑diamino‑4''‑methoxytriphenylamine

polymer, inherent viscosity 0.79 dl/g, softening temp. 248 deg C; monomer(s): 4,4'-diamino-4''-methoxytriphenylamine; terephthalic acid

polymer, inherent viscosity 0.79 dl/g, softening temp. 248 deg C; monomer(s): 4,4'-diamino-4''-methoxytriphenylamine; terephthalic acid

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

vanadocene

terephthalic acid
100-21-0

terephthalic acid

V(3+)*C5H5(1-)*2OOCC6H4COOH(1-)=(C5H5)V(OCOC6H4COOH)2

V(3+)*C5H5(1-)*2OOCC6H4COOH(1-)=(C5H5)V(OCOC6H4COOH)2

Conditions
ConditionsYield
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

1,4-diaza-bicyclo[2.2.2]octane

ammonium sulfate

ammonium sulfate

terephthalic acid
100-21-0

terephthalic acid

zinc(II) oxide

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

[(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
ConditionsYield
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

1,4-diaza-bicyclo[2.2.2]octane

terephthalic acid
100-21-0

terephthalic acid

sodium sulfate
7757-82-6

sodium sulfate

zinc(II) oxide

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

[(zinc)2(terephthalate)2(1,4-diazabicyclo[2.2.2]octane)]*(x)Na2SO4 [Zn2(C6H4(COO)2)2(N2(C2H4)3)]*99Na2SO4, hexagonal

Conditions
ConditionsYield
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

1,4-diaza-bicyclo[2.2.2]octane

potassium sulfate

potassium sulfate

terephthalic acid
100-21-0

terephthalic acid

zinc(II) oxide

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

[(zinc)2(terephthalate)2(1,4-diazabicyclo[2.2.2]octane)]*(x)K2SO4 [Zn2(C6H4(COO)2)2(N2(C2H4)3)]*99K2SO4, hexagonal

Conditions
ConditionsYield
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

terephthalic acid

isopropyl bromide
75-26-3

isopropyl bromide

terephthalic acid diisopropyl ester
6422-84-0

terephthalic acid diisopropyl ester

Conditions
ConditionsYield
With triethylamine at 60℃; for 2h; Inert atmosphere; Ionic liquid;99%
terephthalic acid
100-21-0

terephthalic acid

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

zinc(II) oxide

zinc(II) oxide

[Zn(1,4-benzenedicarboxylate)(H2O)]*DMF
213275-65-1

[Zn(1,4-benzenedicarboxylate)(H2O)]*DMF

Conditions
ConditionsYield
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;

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100-21-0Relevant articles and documents

Highly efficient conversion of aldehydes to carboxylic acid in the presence of platinum porphyrin sensitizers, air and sunlight

Hajimohammadi, Mahdi,Mofakham, Hamid,Safari, Nasser,Manesh, Anahita Mortazavi

, p. 93 - 100 (2012)

A variety of aromatic and aliphatic aldehydes were oxidized to the corresponding carboxylic acids in the presence of platinum porphyrin, sunlight and air in acetonitrile solvent under mild conditions. Nitrobenzaldehydes were found to be very efficient 1O2 scavengers that quench the formation of acids from any aldehyde in the presence of free-base porphyrin sensitizers. However, nitrobenzaldehydes were converted to the corresponding acids in the presence of platinum porphyrins. The platinum porphyrins are very good and efficient catalysts for a wide range of applications in the aerobic conversion of aldehydes to acids.

-

Toland et al.

, p. 5423,5426 (1958)

-

-

Strickland,Bell

, p. 7,9 (1961)

-

Novel oxidation of toluenes catalyzed by reusable vanadyl(IV) sulfate under mild conditions with molecular oxygen

Nakai, Takeo,Iwai, Toshiyuki,Mihara, Masatoshi,Ito, Takatoshi,Mizuno, Takumi

, p. 2225 - 2227 (2010)

Efficient oxidation system using reusable vanadyl(IV) sulfate catalyst was established. Toluenes were easily oxidized under molecular oxygen (0.1 MPa) at 100 °C catalyzed by vanadyl(IV) sulfate to afford the corresponding benzoic acids in excellent yields. The recovered catalyst could be reused without loss of activity.

-

Hay,Blanchard

, p. 1306,1314 (1965)

-

-

Emerson et al.

, p. 1839,1844 (1951)

-

Selectively Upgrading Lignin Derivatives to Carboxylates through Electrochemical Oxidative C(OH)?C Bond Cleavage by a Mn-Doped Cobalt Oxyhydroxide Catalyst

Zhou, Hua,Li, Zhenhua,Xu, Si-Min,Lu, Lilin,Xu, Ming,Ji, Kaiyue,Ge, Ruixiang,Yan, Yifan,Ma, Lina,Kong, Xianggui,Zheng, Lirong,Duan, Haohong

, p. 8976 - 8982 (2021)

Oxidative cleavage of C(OH)?C bonds to afford carboxylates is of significant importance for the petrochemical industry and biomass valorization. Here we report an efficient electrochemical strategy for the selective upgrading of lignin derivatives to carboxylates by a manganese-doped cobalt oxyhydroxide (MnCoOOH) catalyst. A wide range of lignin-derived substrates with C(OH)-C or C(O)-C units undergo efficient cleavage to corresponding carboxylates in excellent yields (80–99 %) and operational stability (200 h). Detailed investigations reveal a tandem oxidation mechanism that base from the electrolyte converts secondary alcohols and their derived ketones to reactive nucleophiles, which are oxidized by electrophilic oxygen species on MnCoOOH from water. As proof of concept, this approach was applied to upgrade lignin derivatives with C(OH)-C or C(O)-C motifs, achieving convergent transformation of lignin-derived mixtures to benzoate and KA oil to adipate with 91.5 % and 64.2 % yields, respectively.

-

Carnelley

, (1877)

-

Dehydro-aromatization of cyclohexene-carboxylic acids by sulfuric acid: Critical route for bio-based terephthalic acid synthesis

Wang, Fei,Tong, Zhaohui

, p. 6314 - 6317 (2014)

A novel dehydro-aromatization reaction under mild reaction conditions was successfully developed using sulfuric acid as a cost-effective and efficient oxidant. This reaction simplified the synthesis of terephthalic acid (TA, an important aromatic monomer precursor) from biomass-derived isoprene and acrylic acid.

9,10-Dihydroanthracene auto-photooxidation efficiently triggered photo-catalytic oxidation of organic compounds by molecular oxygen under visible light

Chen, Mengke,Deng, Youer,Fu, Zaihui,Hu, Wenwei,Jiang, Dabo,Liu, Yachun,Mao, Feng,Su, Anqun,Yang, Bo,Zhang, Chao

, (2020)

The development of mild and efficient process for the selective oxidation of organic compounds by molecular oxygen (O2) can be one of the key technologies for synthesizing oxygenates. This paper discloses an efficient and mild synthesis protocol for the O2-involved ethylbenzene (EB) photooxidation triggered by 910-dihydroanthracene (DHA) auto- photooxidation in acetone under visible light illumination, which can achieve 87.7 percent EB conversion and 99.5 percent acetylacetone (ACP) selectivity under ambient conditions. Also, 62.9 percent EB conversion and 96.3 percent ACP selectivity is obtained in air atmosphere. Furthermore, this protocol has a good adaptability for the photooxidation of other organic substrates such as tetrahydronaphthalene, diphenylmethane, toluene, cyclohexane, cyclohexene, alcohol, methylfuran and thioether to their corresponding oxygenates. A series of control and quenching tests, combined with EPR spectra, suggest that the photo-excited DHA can transfer its photo-electron to O2 to yield a superoxide radical anion (O2??), then DHA is preferentially oxidized to anthraquinone (AQ) by the active O2?? owing to its high reactivity. Finally, the in situ generated AQ as an active photo-catalyst can achieve the photooxidation of EB and other organic compounds by O2. The present photo-autoxidation protocol gives a good example for the O2-based selective oxidation of inert hydrocarbons under mild conditions.

Selective aerobic oxidation of para-xylene in sub- and supercritical water. Part 3: Effects of geometry and mixing in laboratory scale continuous reactors

Pérez, Eduardo,Thomas, Morgan L.,Housley, Duncan,Hamley, Paul A.,Fraga-Dubreuil, Joan,Li, Jun,Lester, Edward,Poliakoff, Martyn

, p. 11289 - 11294 (2016)

In this paper we report a strong dependence of the observed performance of the catalyst on the geometry and the configuration of laboratory scale reactors in the continuous aerobic oxidation of p-xylene in supercritical water. Small differences, such as t

New crystalline modification of terephthalic acid

Sledz, M.,Janczak, J.,Kubiak, R.

, p. 77 - 82 (2001)

The new crystalline modification of terephthalic acid can be obtained either from the commercially available triclinic modification by heating at 250 deg C or directly by a thermal hydrolysis of p-dicyanobenzene. It crystallises in a monoclinic system, space group C2/m with a = 8.940(2), b = 10.442(2), c = 3.790(1) Angstroem, V = 353.7(2) Angstroem3, β = 91.21(3) deg and Z = 2. Both carboxyl groups of terephthalic acid are coplanar with the phenyl ring. The molecules in the crystal are linked through the hydrogen bonds in the carboxyl groups into infinite chains. The orientational disorder is observed in the carboxyl groups. The structure of the monoclinic form is compared with the structure of both the triclinic modification.

Production of Terephthalic Acid from Corn Stover Lignin

Song, Song,Zhang, Jiaguang,G?zayd?n, G?kalp,Yan, Ning

, p. 4934 - 4937 (2019)

Funneling and functionalization of a mixture of lignin-derived monomers into a single high-value chemical is fascinating. Reported herein is a three-step strategy for the production of terephthalic acid (TPA) from lignin-derived monomer mixtures, in which redundant, non-uniform substitutes such as methoxy groups are removed and the desired carboxy groups are introduced. This strategy begins with the hydro-treatment of corn-stover-derived lignin oil over a supported molybdenum catalyst to selectively remove methoxy groups. The generated 4-alkylphenols are converted into 4-alkylbenzoic acids by carbonylation with carbon monoxide. The Co-Mn-Br catalyst then oxidizes various alkyl chains into carboxy groups, transforming the 4-alkylbenzoic acid mixture into a single product: TPA. For this route, the overall yields of TPA based on lignin content of corn stover could reach 15.5 wt %, and importantly, TPA with greater than 99 % purity was obtained simply by first decanting the reaction mixture and then washing the solid product with water.

Introducing nanocrystalline CeO2 as heterogeneous environmental friendly catalyst for the aerobic oxidation of para-xylene to terephthalic acid in water

Deori, Kalyanjyoti,Gupta, Dinesh,Saha, Basudeb,Awasthi, Satish K.,Deka, Sasanka

, p. 7091 - 7099 (2013)

CeO2 nanoparticles exposed in (100) and (111) surfaces have been synthesized and explored as a heterogeneous catalyst for the first time in the oxidation of para-xylene to terephthalic acid. The synthesis and catalysis reaction was environmenta

Ruzicka,Stoll

, p. 271 (1924)

-

Sensemann,Stubbs

, p. 1129 (1931)

-

Carboxylation of Benzoic Acid Using Cyclodextrin as Catalyst

Hirai, Hidefumi,Mihori, Hisashi

, p. 1523 - 1526 (1992)

Benzoic acid is found to undergo carboxylation by warming with carbon tetrachloride in aqueous alkali in the presence of copper powder with β-cyclodextrin as catalyst.The reaction under mild conditions gives terephthalic acid in good yield with high selec

Solvent free oxidation of primary alcohols and diols using thymine iron(iii) catalyst

Al-Hunaiti, Afnan,Niemi, Teemu,Sibaouih, Ahlam,Pihko, Petri,Leskelae, Markku,Repo, Timo

, p. 9250 - 9252 (2010)

In this study, we developed an efficient and selective iron-based catalyst system for the synthesis of ketones from secondary alcohols and carboxylic acids from primary alcohol. In situ generated iron catalyst of thymine-1-acetate (THA) and FeCl3 under solvent-free condition exhibits high activity. As an example, 1-octanol and 2-octanol were oxidized to 1-octanoic acid and 2-octanone with 89% and 98% yields respectively.

Catalytic oxidation of alkyl aromatics using a novel silica supported Schiff base complex

Chisem, Ian C.,Rafelt, John,Shieh, M. Tantoh,Chisem, Janet,Clark, James H.,Jachuck, Roshan,Macquarrie, Duncan,Ramshaw, Colin,Scott, Keith

, p. 1949 - 1950 (1998)

A new heterogeneous catalyst based on a chemically modified mesoporous silica gel and possessing immobilised chromium ions has been prepared and successfully applied to the aerial oxidation of alkyl aromatics at atmospheric pressure and in the absence of solvent.

One-step synthesis of terephthalic acid from benzene in water using cyclodextrin as catalyst

Shiraishi, Yukihide,Tashiro, Shigetoshi,Toshima, Naoki

, p. 828 - 829 (2000)

The one-pot synthesis of terephthalic acid from benzene has been achieved by treatment with tetrachloromethane, copper powder, and an aqueous sodium hydroxide solution using cyclodextrin as a catalyst at 30 °C under nitrogen in 46 mol% yield with 100% selectivity.

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Fichter,Meyer

, p. 285 (1925)

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Holtz

, p. 1166 (1971)

Furan Carboxylic Acids Production with High Productivity by Cofactor-engineered Whole-cell Biocatalysts

Zhang, Xue-Ying,Wang, Xin,Li, Nan-Wei,Guo, Ze-Wang,Zong, Min-Hua,Li, Ning

, p. 3257 - 3264 (2020)

Furan carboxylic acids are useful chemicals in various industries. In this work, biocatalytic production of furan carboxylic acids was reported with high productivities by cofactor-engineered Escherichia coli cells. NADH oxidase (NOX) was introduced into E. coli harboring aldehyde dehydrogenases (ALDHs) to promote intracellular NAD+ regeneration, thus significantly enhancing ALDH-catalyzed oxidation. These engineered biocatalysts were capable of efficient aerobic oxidation of a variety of aromatic aldehydes. More importantly, they exhibited high substrate tolerance toward toxic furans. E. coli co-expressing vanillin dehydrogenase and NOX (E. coli_CtVDH1_NOX) enabled efficient oxidation of 250 mM of 5-hydroxymethylfurfural (HMF) to 5-hydroxymethyl-2-furancarboxylic acid (HMFCA), providing a productivity of 3.7 g/L h. With E. coli_CtVDH2_NOX as catalyst, up to 240 mM of furfural and 5-methoxymethylfurfural (MMF) could be smoothly oxidized. 2-Furoic acid (FCA, 227 mM) and 5-methoxymethyl-2-furancarboxylic acid (MMFCA, 287 mM) were produced in fed-batch synthesis, providing the productivities of 2.0 and 5.6 g/L h, respectively.

Ogata et al.

, p. 6005 (1957)

Selective oxidation of para-xylene to terephthalic acid by μ3-oxo-bridged Co/Mn cluster complexes encapsulated in zeolite-Y

Ratnasamy,Chavan,Srinivas

, p. 409 - 419 (2001)

Novel, solid catalysts of μ3-oxo-bridged Co/Mn cluster complexes were prepared and their catalytic properties (in the "neat" state and when encapsulated in zeolite Y) in the selective oxidation of paraxylene to terephthalic acid with oxygen wer

Stepwise benzylic oxygenation via uranyl-photocatalysis

Hu, Deqing,Jiang, Xuefeng

supporting information, p. 124 - 129 (2022/01/19)

Stepwise oxygenation at the benzylic position (1°, 2°, 3°) of aromatic molecules was comprehensively established under ambient conditions via uranyl photocatalysis to produce carboxylic acids, ketones, and alcohols, respectively. The accuracy of the stepwise oxygenation was ensured by the tunability of catalytic activity in uranyl photocatalysis, which was adjusted by solvents and additives demonstrated through Stern–Volmer analysis. Hydrogen atom transfer between the benzylic position and the uranyl catalyst facilitated oxygenation, further confirmed by kinetic studies. Considerably improved efficiency of flow operation demonstrated the potential for industrial synthetic application.

Photoinduced FeCl3-Catalyzed Alkyl Aromatics Oxidation toward Degradation of Polystyrene at Room Temperature?

Zhang, Guoxiang,Zhang, Zongnan,Zeng, Rong

supporting information, p. 3225 - 3230 (2021/09/28)

While polystyrene is widely used in daily life as a synthetic plastic, the subsequently selective degradation is still very challenging and highly required. Herein, we disclose a highly practical and selective reaction for the catalytically efficient oxidation of alkyl aromatics (including 1°, 2°, and 3° alkyl aromatics) to carboxylic acids. While dioxygen was used as the sole terminal oxidant, this protocol was catalyzed by the inexpensive and readily available ferric compound (FeCl3) with irradiation of visible light (blue LEDs) under only 1 atmosphere of O2 at room temperature. This system could further facilitate the selective degradation of polystyrene to benzoic acid, providing an important and practical tool to generate high-value chemical from abundant polystyrene wastes.

Practical scale up synthesis of carboxylic acids and their bioisosteres 5-substituted-1H-tetrazoles catalyzed by a graphene oxide-based solid acid carbocatalyst

Mittal, Rupali,Kumar, Amit,Awasthi, Satish Kumar

, p. 11166 - 11176 (2021/03/31)

Herein, catalytic application of a metal-free sulfonic acid functionalized reduced graphene oxide (SA-rGO) material is reported for the synthesis of both carboxylic acids and their bioisosteres, 5-substituted-1H-tetrazoles. SA-rGO as a catalytic material incorporates the intriguing properties of graphene oxide material with additional benefits of highly acidic sites due to sulfonic acid groups. The oxidation of aldehydes to carboxylic acids could be efficiently achieved using H2O2as a green oxidant with high TOF values (9.06-9.89 h?1). The 5-substituted-1H-tetrazoles could also be effectively synthesized with high TOF values (12.08-16.96 h?1). The synthesis of 5-substituted-1H-tetrazoles was corroborated by single crystal X-ray analysis and computational calculations of the proposed reaction mechanism which correlated well with experimental findings. Both of the reactions could be performed efficiently at gram scale (10 g) using the SA-rGO catalyst. SA-rGO displays eminent reusability up to eight runs without significant decrease in its productivity. Thus, these features make SA-rGO riveting from an industrial perspective.

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