Conditions | Yield |
---|---|
With sodium bromate; 4 In water at 60℃; for 15h; | 100% |
With sodium hypochlorite; nickel dichloride In dichloromethane; water at 0 - 20℃; for 4h; | 90% |
With oxygen; sodium methylate; silver trifluoromethanesulfonate In tetrahydrofuran; methanol at 37℃; under 760.051 Torr; for 6h; Sealed tube; | 88% |
Conditions | Yield |
---|---|
With sodium nitrite In trifluoroacetic acid | 100% |
With oxygen; trifluoroacetic acid; sodium nitrite at 0 - 20℃; for 5.25h; Product distribution / selectivity; | 100% |
With dihydrogen peroxide; ortho-tungstic acid In water at 90℃; for 20h; Product distribution / selectivity; | 99% |
Conditions | Yield |
---|---|
With oxygen; sodium nitrite In trifluoroacetic acid at 0 - 20℃; for 5h; | 100% |
With oxygen; potassium nitrate; trifluoroacetic acid at 0 - 20℃; for 5.25h; Product distribution / selectivity; | 100% |
With potassium nitrite; oxygen; trifluoroacetic acid at 0 - 20℃; for 5.25h; Product distribution / selectivity; | 100% |
Conditions | Yield |
---|---|
With dihydrogen peroxide; Na12[WZn3(H2O)2(ZnW9O34)2] at 75℃; for 7h; | 100% |
With C24H33IrN4O3; water; sodium hydroxide for 18h; Reflux; | 97% |
With Gluconobacter oxydans DSM 50049 In aq. phosphate buffer at 30℃; pH=4.3-7; Microbiological reaction; | 95.5% |
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; indium(III) chloride In water at 90℃; | 100% |
With hydrogenchloride; sodium tungstate; phosphoric acid; dihydrogen peroxide at 90℃; for 5h; | 94% |
With sodium tungstate (VI) dihydrate; dihydrogen peroxide at 87℃; for 16h; | 79% |
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; indium(III) chloride In water at 90℃; | 100% |
With dodecyltrimethylammonium phosphotungstate; water; dihydrogen peroxide In toluene at 80℃; for 12h; Reagent/catalyst; chemoselective reaction; | 94% |
With dihydrogen peroxide; [WO(O2)2*1,10-phenanthroline] at 90℃; for 12h; | 85.9% |
Conditions | Yield |
---|---|
With hydrogen iodide; acetic acid In water at 160℃; under 37503.8 Torr; for 4.16667h; Temperature; Solvent; Reagent/catalyst; Inert atmosphere; | 100% |
With hydrogen iodide; hydrogen; 5percent Pd/Silica In acetic acid at 160℃; under 37478.5 Torr; for 3h; Product distribution / selectivity; Inert atmosphere; | 99% |
With hydrogen iodide; hydrogen In water; propionic acid at 160℃; under 25858.1 Torr; for 2h; Kinetics; Reagent/catalyst; Pressure; Concentration; Temperature; Solvent; Autoclave; | 89% |
6-hydroxyimino-6-nitrohexanoic acid
Adipic acid
Conditions | Yield |
---|---|
With nitric acid; copper(II) ion; vanadium(5+) at 73℃; | 99.9% |
Conditions | Yield |
---|---|
With nitric acid; trifluoroacetic acid; N-hydroxy-5-carboxy-phthalimide at 23℃; for 18h; Reagent/catalyst; | 99% |
With 2-pyrazylcarboxylic acid; FeCl2(κ3-HC(C3H3N2)3); ozone at 20℃; for 6h; Catalytic behavior; Time; Reagent/catalyst; Schlenk technique; Green chemistry; | 96% |
In acetic acid at 115℃; under 22502.3 Torr; for 5h; Reagent/catalyst; Pressure; | 95% |
Conditions | Yield |
---|---|
With oxygen; acetic acid In water at 60℃; under 750.075 Torr; for 0.5h; | 99% |
With oxygen; H6[PMo9V3O40]*11H2O In methanol at 60℃; under 750.06 Torr; for 24h; Product distribution; Further Variations:; Catalysts; Temperatures; | 90% |
With sodium hypochlorite for 0.5h; Irradiation; | 87% |
A
Adipic acid
B
tetraphenylantimony(V) chloride
Conditions | Yield |
---|---|
With aq. HCl | A n/a B 99% |
Conditions | Yield |
---|---|
With ozone In tetrachloromethane at 20℃; for 0.3h; UV-irradiation; | 99% |
Conditions | Yield |
---|---|
With (tetra-n-butyl-ammonium)3(tetra(oxodiperoxotungstato)phosphate); dihydrogen peroxide In water at 92℃; for 2.5h; | 98% |
With dihydrogen peroxide In water; acetonitrile at 90℃; for 8h; Temperature; Green chemistry; | 97% |
With phosphoric acid; sulfuric acid; water; dihydrogen peroxide; ortho-tungstic acid In water at 73℃; for 2h; | 97.4% |
Conditions | Yield |
---|---|
With ethanol; palladium on activated charcoal; sodium hydroxide; silicon at 20℃; for 72h; Schlenk technique; | 96% |
With hydrogen In water at 80℃; under 22502.3 - 75007.5 Torr; for 12h; Autoclave; | 95% |
With hydrogen; palladium on activated charcoal for 3h; Ambient temperature; | |
With hydrogen; Ru10Pt2 In ethanol at 79.85℃; under 22501.8 Torr; for 5h; | |
With 2% Rh/C; hydrogen In water at 80℃; under 37503.8 Torr; pH=3; Reagent/catalyst; Pressure; Autoclave; |
2,3,10,11,17,18,19,20-Octaoxa-tricyclo[10.4.2.24,9]icosane
Adipic acid
Conditions | Yield |
---|---|
With hydrogen; Lindlar's catalyst In 1,4-dioxane Product distribution; other reagent - triphenylphosphine; | 96% |
Conditions | Yield |
---|---|
With nitric acid; sodium nitrite In water at 70℃; for 1h; Temperature; Time; Concentration; | 95% |
With H1Mn0.25Co0.75(3+)*Mo12O40P(3-); dihydrogen peroxide at 90℃; for 20h; | 75% |
With ammonium vanadate; copper (II)-salt; water; nitric acid |
Conditions | Yield |
---|---|
With amberlyst 15 In methanol; water at 80℃; for 2h; Solvent; High pressure; Green chemistry; | 95% |
With Dowex-50 In water for 12h; Heating; | 78% |
With trimethylsilyl bromide; iodine(I) bromide at 100℃; for 17h; | 68% |
6-nitrohexanoic acid
Adipic acid
Conditions | Yield |
---|---|
With acetic acid; sodium nitrite In dimethyl sulfoxide at 35℃; | 95% |
Conditions | Yield |
---|---|
With manganese dioxide; dihydrogen peroxide In 1,4-dioxane; acetic acid | 95% |
With manganese dioxide; dihydrogen peroxide In 1,4-dioxane | 51% |
cis,cis-Muconic acid
A
γ-(carboxymethyl)-γ-butyrolactone
B
Adipic acid
Conditions | Yield |
---|---|
With hydrogen In water at 80℃; under 22502.3 - 75007.5 Torr; for 12h; Autoclave; | A 5% B 95% |
2-bromocyclohexylamine
Adipic acid
Conditions | Yield |
---|---|
Stage #1: 2-bromocyclohexylamine With potassium sulfate at 40℃; for 3.16667h; Stage #2: With chromium(0) hexacarbonyl at 40℃; for 2h; Stage #3: With methyl heptanoate at 52℃; for 2.16667h; | 95% |
adipic acid di(3-pentyl) ester
Adipic acid
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol; water for 12h; Reflux; | 94% |
Adipic acid
Conditions | Yield |
---|---|
With nitric acid; toluene-4-sulfonic acid at 60℃; for 0.166667h; Temperature; Reagent/catalyst; Time; | 94% |
Conditions | Yield |
---|---|
With HeMaRaphos; water; toluene-4-sulfonic acid; palladium dichloride In tetrahydrofuran at 125℃; under 30003 Torr; for 24h; Autoclave; Green chemistry; regioselective reaction; | 93% |
Conditions | Yield |
---|---|
With hydrogenchloride; sodium tungstate; phosphoric acid; dihydrogen peroxide at 90℃; for 5h; | 92% |
Stage #1: cis-1,2-cyclohexane With 2,3,4,5,6-pentamethyliodobenzene; oxygen; isobutyraldehyde In 1,2-dichloro-ethane under 760.051 Torr; for 36h; Stage #2: With sodium chlorite; 2-methyl-but-2-ene In aq. phosphate buffer; 1,2-dichloro-ethane; tert-butyl alcohol at 25℃; for 14h; | 80% |
With potassium carbonate for 2.7h; Ambient temperature; electrolysis: nickel(III) oxide hydroxide electrode, 0.3 A; | 74% |
Conditions | Yield |
---|---|
With platinum on carbon; hydrogen In water at 24℃; under 5250.53 Torr; for 8h; | 92% |
With platinum on carbon; hydrogen In water at 24℃; under 5171.62 Torr; for 8h; Autoclave; Inert atmosphere; | 92% |
With hydrogen; palladium | |
With hydrogen; palladium | |
With 1% Pd on activated carbon; hydrogen In ethanol at 24℃; under 18001.8 Torr; Catalytic behavior; Reagent/catalyst; Flow reactor; |
Conditions | Yield |
---|---|
With phosphoric acid; sulfuric acid; water; dihydrogen peroxide; ortho-tungstic acid at 73℃; for 2h; | A 90.2% B 54% |
With dihydrogen peroxide; ortho-tungstic acid In tert-butyl alcohol for 24h; Heating; | A 81% B 9% |
With 1-butyl-3-methylimidazolium phosphotungstate; dihydrogen peroxide; acetophenone at 60℃; for 72h; Reagent/catalyst; | A 61% B 12 %Chromat. |
Conditions | Yield |
---|---|
With hydrogen In water at 140℃; under 62819.5 Torr; for 4h; Inert atmosphere; Sealed tube; Autoclave; | 90% |
With sulfuric acid; water at 70℃; Electrochemical reaction; Nickel cathode/platinum anode; | 68% |
Conditions | Yield |
---|---|
With sulfuric acid at 90℃; for 1h; | 89% |
Conditions | Yield |
---|---|
With boron trifluoride at 65℃; for 0.333333h; | 100% |
at 130℃; for 4h; Temperature; | 99.81% |
With aluminum(III) sulphate octadecahydrate at 110℃; for 0.166667h; Sealed tube; Microwave irradiation; | 97.7% |
Conditions | Yield |
---|---|
With hydrogen In water at 160℃; under 22502.3 Torr; for 18h; Molecular sieve; chemoselective reaction; | 100% |
With hydrogen In water at 130℃; under 37503.8 Torr; for 18h; Pressure; Reagent/catalyst; Autoclave; | 89% |
With hydrogen In water at 120℃; under 35409.9 Torr; for 2.5h; Reagent/catalyst; Pressure; Temperature; | 88% |
Conditions | Yield |
---|---|
With PPE for 15h; Ambient temperature; | 100% |
(i) 2-fluoro-1-methyl-pyridinium toluene-4-sulfonate, Et3N, (ii) /BRN= 506523/, Et3N; Multistep reaction; |
Adipic acid
2-(vinyloxy)ethyl isothiocyanate
Conditions | Yield |
---|---|
trifluoroacetic acid at 70 - 75℃; for 1h; | 100% |
Conditions | Yield |
---|---|
With chloro-trimethyl-silane at 0 - 20℃; for 12h; Inert atmosphere; | 100% |
With sulfuric acid at 65℃; for 12h; Inert atmosphere; | 90% |
Stage #1: Adipic acid With trichloroisocyanuric acid; triphenylphosphine In dichloromethane at 0℃; for 0.75h; Stage #2: allyl alcohol With triethylamine In dichloromethane at 20℃; for 1h; | 65% |
Conditions | Yield |
---|---|
Stage #1: metformin hydrochloride With sodium hydroxide In water; acetonitrile at 20℃; Stage #2: Adipic acid In water; acetonitrile at 20℃; Product distribution / selectivity; | 100% |
Stage #1: metformin hydrochloride With sodium hydroxide In tetrahydrofuran; water at 20℃; Stage #2: Adipic acid In tetrahydrofuran; water at 20℃; Product distribution / selectivity; | 97.7% |
Stage #1: metformin hydrochloride With sodium hydroxide In water; acetone at 20℃; Stage #2: Adipic acid In water; acetone at 20℃; Product distribution / selectivity; | 92.3% |
Adipic acid
cobalt(II) acetate
(R,R)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine
Conditions | Yield |
---|---|
Stage #1: cobalt(II) acetate; (R,R)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine In ethanol for 5h; Heating / reflux; Stage #2: Adipic acid With oxygen In dichloromethane; acetone at 20℃; for 3h; | 100% |
Conditions | Yield |
---|---|
In acetone at 80 - 150℃; for 0.666667h; | 100% |
Conditions | Yield |
---|---|
In acetone at 80 - 150℃; for 0.666667h; | 100% |
Conditions | Yield |
---|---|
In tetrahydrofuran for 0.5h; | 100% |
In tetrahydrofuran Product distribution / selectivity; | |
Stage #1: Adipic acid; meloxicam for 0.25h; Milling; Stage #2: In acetone Solvent; |
Adipic acid
(3R,5R)-3-[1-methyl-1-(2-trifluoromethyl-pyrimidin-4-yl)-ethylamino]-5-(3-trifluoromethoxy-phenyl)-1-(4-trifluoromethyl-phenyl)-pyrrolidin-2-one
Conditions | Yield |
---|---|
In methanol; ethyl acetate at 20℃; Product distribution / selectivity; | 100% |
Adipic acid
thiosemicarbazide
5,5′-(butane-1,4-diyl)bis(1,3,4-thiadiazol-2-amine)
Conditions | Yield |
---|---|
Stage #1: thiosemicarbazide With 1-ethyl-3-methylimidazolium hydrogensulfate at 50℃; for 0.25h; Stage #2: Adipic acid With sulfuric acid at 100℃; | 100% |
With phosphorus pentachloride at 20℃; for 0.333333h; Time; Milling; | 95% |
With trichlorophosphate for 5h; Reflux; | 76.9% |
Adipic acid
2-chloroallyl alcohol
adipic acid bis-(2-chloro-allyl ester)
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In benzene for 16h; Dean-Stark; Reflux; Inert atmosphere; | 99% |
With benzenesulfonic acid; benzene at 83 - 96℃; |
Adipic acid
1,2-diamino-benzene
2,2'-(1,4-butanediyl)bis(1H-benzimidazole)
Conditions | Yield |
---|---|
With tetrafluoroboric acid In water at 150℃; for 2h; | 99% |
With hydrogenchloride In water for 12h; Reflux; | 41% |
Adipic acid
adipic acid anhydride
Conditions | Yield |
---|---|
With N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride; triethylamine In dichloromethane at 20℃; for 1h; | 99% |
With 1-ethyl-piperidine; p-toluenesulfonyl chloride In methanol | |
In acetic anhydride |
Conditions | Yield |
---|---|
With thexylbromoborane dimethyl sulfide complex In carbon disulfide; dichloromethane at -20 - 20℃; for 1h; | 99% |
With 9-borabicyclo[3.3.1]nonane dimer; tert.-butyl lithium 1.) THF, room temp.; 2.) THF, pentane, -20 deg C, 10 min and room temp., 3 h; Yield given. Multistep reaction; |
Adipic acid
1,1'-bis(4-pyridinyl)ferrocene
Conditions | Yield |
---|---|
In methanol 1:1 mixt. ground for 5 min, dissolved in methanol; crystd.; | 99% |
Adipic acid
AZD4316
Conditions | Yield |
---|---|
In acetonitrile Conversion of starting material; | 99% |
The Adipic acid is an organic compound with the formula C6H10O4. The IUPAC name of this chemical is hexanedioic acid. With the CAS registry number 124-04-9, it is also named as Adipinsaure. The product's categories are Industrial/Fine Chemicals; alpha,omega-Alkanedicarboxylic Acids; alpha,omega-Bifunctional Alkanes; Monofunctional & alpha,omega-Bifunctional Alkanes. Besides, it is a white crystalline powder, which should be stored in a closed and dry place at temperature of 4 °C.
Physical properties about Adipic acid are: (1)ACD/BCF (pH 5.5): 1; (2)ACD/BCF (pH 7.4): 1; (3)ACD/KOC (pH 5.5): 1; (4)ACD/KOC (pH 7.4): 1; (5)#H bond acceptors: 4; (6)#H bond donors: 2; (7)#Freely Rotating Bonds: 5; (8)Polar Surface Area: 74.6 Å2; (9)Index of Refraction: 1.476; (10)Molar Refractivity: 32.975 cm3; (11)Molar Volume: 116.827 cm3; (12)Polarizability: 13.072×10-24cm3; (13)Surface Tension: 52.486 dyne/cm; (14)Density: 1.251 g/cm3; (15)Flash Point: 172.745 °C; (16)Enthalpy of Vaporization: 63.952 kJ/mol; (17)Boiling Point: 338.539 °C at 760 mmHg.
Preparation: currently adipic acid is produced from a mixture of cyclohexanol and cyclohexanone called "KA oil", the abbreviation of "ketone-alcohol oil." The KA oil is oxidized with nitric acid to give adipic acid, via a multistep pathway. Early in the reaction the cyclohexanol is converted to the ketone, releasing nitrous acid:
HOC6H11 + HNO3 → OC6H10 + HNO2 + H2O
Among its many reactions, the cyclohexanone is nitrosated, setting the stage for the scission of the C-C bond:
HNO2 + HNO3 → NO+NO3- + H2O
OC6H10 + NO+ → OC6H9-2-NO + H+
Side products of the method include glutaric and succinic acids.
Uses of Adipic acid: the majority of adipic acid is used as monomer for the production of nylon by a polycondensation reaction with hexamethylene diamine forming 6,6-nylon. Other major applications also involve polymers: it is a monomer for production of Polyurethane and its esters are plasticizers, especially in PVC. In medicine, adipic acid has been incorporated into controlled-release formulation matrix tablets to obtain pH-independent release for both weakly basic and weakly acidic drugs. It has also been incorporated into the polymeric coating of hydrophilic monolithic systems to modulate the intragel pH, resulting in zero-order release of a hydrophilic drug. The disintegration at intestinal pH of the enteric polymer shellac has been reported to improve when adipic acid was used as a pore-forming agent without affecting release in the acidic media. Other controlled-release formulations have included adipic acid with the intention of obtaining a late-burst release profile. Small but significant amounts of adipic acid are used as a food ingredient as a flavorant and gelling aid. It is used in some calcium carbonate antacids to make them tart.
When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1)SMILES: C(CCC(=O)O)CC(=O)O
(2)InChI: InChI=1/C6H10O4/c7-5(8)3-1-2-4-6(9)10/h1-4H2,(H,7,8)(H,9,10)
(3)InChIKey: WNLRTRBMVRJNCN-UHFFFAOYAY
(4)Std. InChI: InChI=1S/C6H10O4/c7-5(8)3-1-2-4-6(9)10/h1-4H2,(H,7,8)(H,9,10)
(5)Std. InChIKey: WNLRTRBMVRJNCN-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intravenous | 680mg/kg (680mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BLOOD: HEMORRHAGE | Journal of Agricultural and Food Chemistry. Vol. 5, Pg. 759, 1957. |
mouse | LD50 | oral | 1900mg/kg (1900mg/kg) | GASTROINTESTINAL: OTHER CHANGES | Journal of Agricultural and Food Chemistry. Vol. 5, Pg. 759, 1957. |
rabbit | LD50 | oral | > 11gm/kg (11000mg/kg) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 48(9), Pg. 72, 1983. | |
rat | LD50 | intraperitoneal | 275mg/kg (275mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) GASTROINTESTINAL: OTHER CHANGES BLOOD: HEMORRHAGE | Journal of Agricultural and Food Chemistry. Vol. 5, Pg. 759, 1957. |
rat | LD50 | oral | > 11gm/kg (11000mg/kg) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 48(9), Pg. 72, 1983. |
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