619-82-9

Usage

Chemical Properties

white to light yellow crystal powder

Uses

It is a pharmaceutical intermediate.

InChI:InChI=1/C8H12O4/c9-7(10)5-1-2-6(4-3-5)8(11)12/h5-6H,1-4H2,(H,9,10)(H,11,12)/t5-,6-

Synthetic route

C14H24O6 → 1,4-cyclohexanedicarboxylic acid (619-82-9)

Conditions	Yield
With trifluoroacetic acid In tetrahydrofuran at 50℃; for 4h;	99%

C16H28O8 → 1,4-cyclohexanedicarboxylic acid (619-82-9)

Conditions	Yield
With trifluoroacetic acid In tetrahydrofuran at 50℃; for 3.5h;	99%

terephthalic acid (100-21-0) → 1,4-cyclohexanedicarboxylic acid (619-82-9)

Conditions	Yield
With 5%-palladium/activated carbon; hydrogen In water at 150℃; under 30003 Torr; for 5.5h;	92%

1,4-benzenedicarboxylic acid dimethyl ester (120-61-6) → 1,4-cyclohexanedicarboxylic acid (619-82-9) + cis-cyclohexane-1,4-dicarboxylic acid (619-81-8)

Conditions	Yield
With hydrogenchloride; methanol Hydrogenation.weiteres Reagens: Platin; Behandlung des Reaktionsprodukts mit warmer wss. Natronlauge oder warmer wss. Salzsaeure;
With hydrogenchloride; acetic acid Hydrogenation.weiteres Reagens: Platin; Behandlung des Reaktionsprodukts mit warmer wss. Natronlauge oder warmer wss. Salzsaeure;

terephthalic acid (100-21-0) → 1,4-cyclohexanedicarboxylic acid (619-82-9) + cis-cyclohexane-1,4-dicarboxylic acid (619-81-8)

Conditions	Yield
With palladium on activated charcoal; water at 180 - 200℃; under 128714 - 257428 Torr; Hydrogenation;
With hydrogen; acetic acid; platinum
With water; pyrographite; ruthenium at 140℃; under 257428 Torr; Hydrogenation;
With 5%-palladium/activated carbon; hydrogen In water at 150℃; under 37503.8 Torr; Reagent/catalyst; Pressure; Time; Autoclave; Overall yield = 99.5 %;	A n/a B n/a
With water; hydrogen at 80℃; under 37503.8 Torr; for 2h; Reagent/catalyst; Autoclave;	A n/a B n/a

cis-cyclohexane-1,4-dicarboxylic acid (619-81-8) → 1,4-cyclohexanedicarboxylic acid (619-82-9)

Conditions	Yield
With hydrogenchloride at 180℃;

dimethyl 1,4-cyclohexanedicarboxylate → 1,4-cyclohexanedicarboxylic acid (619-82-9) + trans-4-(methoxycarbonyl)cyclohexanecarboxylic acid (15177-67-0)

Conditions	Yield
With methanol; potassium hydroxide

cyclohex-1-ene-1,4-dicarboxylic acid (2205-27-8) → 1,4-cyclohexanedicarboxylic acid (619-82-9)

Conditions	Yield
With hydrogen iodide

cyclohexane-1,1,4-tricarboxylic acid (1459-30-9) → 1,4-cyclohexanedicarboxylic acid (619-82-9)

Conditions	Yield
at 200 - 220℃;

trans-Cyclohex-2-ene-1,4-dicarboxylic acid (3919-11-7, 3919-12-8, 19618-93-0, 131721-06-7, 131721-07-8) → 1,4-cyclohexanedicarboxylic acid (619-82-9)

Conditions	Yield
With acetic acid; platinum Hydrogenation;

1,1,4,4-Cyclohexanetetracarboxylic acid (153032-61-2) → 1,4-cyclohexanedicarboxylic acid (619-82-9) + cis-cyclohexane-1,4-dicarboxylic acid (619-81-8)

Conditions	Yield
at 250℃;

oxalyl dichloride (79-37-8) + cyclohexanylcarbonyl chloride (2719-27-9) → 1,4-cyclohexanedicarboxylic acid (619-82-9)

Conditions	Yield
With Perbenzoic acid anschliessendes Hydrolysieren;

trans-dimethyl cyclohex-2-ene-1,4-dicarboxylate (71195-27-2, 71195-28-3) → 1,4-cyclohexanedicarboxylic acid (619-82-9)

Conditions	Yield
(i) (hydrogenation), (ii) (hydrolysis); Multistep reaction;

hydrogenchloride (7647-01-0) + cis-cyclohexane-1,4-dicarboxylic acid (619-81-8) → 1,4-cyclohexanedicarboxylic acid (619-82-9)

Conditions	Yield
at 180℃;

2-bromo-trans-hexahydroterephthalic acid → 1,4-cyclohexanedicarboxylic acid (619-82-9)

Conditions	Yield
With acetic acid; zinc

cis-cyclohexane-1,4-dicarbonitrile (6550-96-5) + aqueous KOH-solution → 1,4-cyclohexanedicarboxylic acid (619-82-9)

(+-)-cyclohexene-(1)-dicarboxylic acid-(1.4)-dimethyl ester → 1,4-cyclohexanedicarboxylic acid (619-82-9) + cis-cyclohexane-1,4-dicarboxylic acid (619-81-8)

Conditions	Yield
With acetic acid; platinum Hydrogenation.Behandlung des Reaktionsprodukts mit warmer methanol. Natronlauge;
With acetic acid; platinum Hydrogenation.Behandlung des Reaktionsprodukts mit warmer wss. Salzsaeure;

1.4-dibromo-cis-hexahydroterephthalic acid → 1,4-cyclohexanedicarboxylic acid (619-82-9) + cis-cyclohexane-1,4-dicarboxylic acid (619-81-8)

Conditions	Yield
With acetic acid; zinc

1.4-dibromo-trans-hexahydroterephthalic acid → 1,4-cyclohexanedicarboxylic acid (619-82-9) + cis-cyclohexane-1,4-dicarboxylic acid (619-81-8)

Conditions	Yield
With sodium amalgam
With acetic acid; zinc
With acetic acid; zinc

cyclohexane-tetracarboxylic acid-(1.1.4.4) → 1,4-cyclohexanedicarboxylic acid (619-82-9) + cis-cyclohexane-1,4-dicarboxylic acid (619-81-8)

Conditions	Yield
at 240℃;

dipotassium-salt of/the/ terephthalic acid → 1,4-cyclohexanedicarboxylic acid (619-82-9) + cis-cyclohexane-1,4-dicarboxylic acid (619-81-8)

Conditions	Yield
With copper-nickel-cobalt catalyst; water at 320℃; Hydrogenation;

terephthalic acid (100-21-0) + acetic acid (64-19-7) + platinum black → 1,4-cyclohexanedicarboxylic acid (619-82-9) + cis-cyclohexane-1,4-dicarboxylic acid (619-81-8)

Conditions	Yield
Hydrogenation;

dimethyl 1-cyclohexen-1,4-dicarboxylate (22646-79-3) + acetic acid (64-19-7) + platinum → 1,4-cyclohexanedicarboxylic acid (619-82-9) + cis-cyclohexane-1,4-dicarboxylic acid (619-81-8)

Conditions	Yield
Behandlung des Reaktionsprodukts mit warmer wss. Salzsaeure.Hydrogenation;
Behandlung des Reaktionsprodukts mit methanol. Natronlauge.Hydrogenation;

cyclohex-1-ene-1,4-dicarboxylic acid (2205-27-8) + hydrogen iodide (10034-85-2) → 1,4-cyclohexanedicarboxylic acid (619-82-9)

Conditions	Yield
at 240℃;

cyclohexane-1,1,4-tricarboxylic acid (1459-30-9) → carbon dioxide (124-38-9) + 1,4-cyclohexanedicarboxylic acid (619-82-9)

Conditions	Yield
at 200 - 220℃;

1,4-dibromo-trans-cyclohexane-1,4-dicarboxylic acid dimethyl ester (1659-96-7) + acetic acid (64-19-7) + zinc-dust → 1,4-cyclohexanedicarboxylic acid (619-82-9) + cis-cyclohexane-1,4-dicarboxylic acid (619-81-8)

Conditions	Yield
anschl. Verseifung;

2,5-dibromo-cyclohexane-1,4-dicarboxylic acid (58498-22-9) + acetic acid (64-19-7) + zinc dust → 1,4-cyclohexanedicarboxylic acid (619-82-9)

Conditions	Yield
2.5-dibromo-trans-hexahydroterephthalic acid;

2-bromo-cyclohexane-1,4-dicarboxylic acid (58498-24-1) + acetic acid (64-19-7) + zinc dust → 1,4-cyclohexanedicarboxylic acid (619-82-9)

Conditions	Yield
2-bromo-trans-hexahydroterephthalic acid;

1,4-dibromo-cyclohexane-1r,4t-dicarboxylic acid (54638-93-6) + sodium amalgam → 1,4-cyclohexanedicarboxylic acid (619-82-9) + cis-cyclohexane-1,4-dicarboxylic acid (619-81-8)

ethanol (64-17-5) + 1,4-cyclohexanedicarboxylic acid (619-82-9) → diethyl cyclohexane-trans-1,4-dicarboxylate (19145-96-1)

Conditions	Yield
With sulfuric acid for 20h; Reflux;	100%

cobalt(II) nitrate hexahydrate + 1,4-cyclohexanedicarboxylic acid (619-82-9) + water (7732-18-5) → Co5(OH)8(trans-1,4-cyclohexanedicarboxylate)*4H2O

Conditions

Yield

With NaOH In water High Pressure; a soln. of Co-contg. compd. was added to a soln. of a mixt. of cis- and trans-1,4-cyclohexanedicarboxylic acid and NaOH; addn. of barbityric acid (2 mmol) and an aq. soln. of NaOH (2 mmol); heating in autoclave at 170-200°C for 16 h; cooling in a water bath; the barbituric acid was sepd. from the crystalsby flotation in a water/methanol mixt. and decantation; the crystals we re washed with acetone and dried in air; elem. anal. powder XRD;

99%

1,4-cyclohexanedicarboxylic acid (619-82-9) + cis-cyclohexane-1,4-dicarboxylic acid (619-81-8) + N,N-Bis-(2-methoxy-ethyl)-2-({[2-(4-methoxy-phenyl)-ethylcarbamoyl]-methyl}-amino)-acetamide; hydrochloride → N,N'-bis(N-(2-(4-methoxyphenyl)ethyl)carboxamidomethyl)-N,N'-bis(N,N-di(2-methoxyethyl)carboxamidomethyl)cyclohexane-1,4-dicarboxamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In 1,4-dioxane; hydrogenchloride at 25℃; for 16h; Condensation;	97%

1,4-cyclohexanedicarboxylic acid (619-82-9) → trans-1,4-cyclohexanedicarboxylic acid dichloride (13170-66-6, 14571-47-2, 19988-54-6)

Conditions	Yield
With thionyl chloride; N-benzyl-N,N,N-triethylammonium chloride In 1,2-dichloro-ethane for 0.5h; Heating;	96%
With thionyl chloride
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane for 18h; Ambient temperature;

nickel(II) nitrate hexahydrate + 1,4-cyclohexanedicarboxylic acid (619-82-9) + tris[4-(1Himidazol-1-yl)-phenyl]amine + water (7732-18-5) → {[Ni(tris[4-(1Himidazol-1-yl)-phenyl]amine)(trans-1,4-cyclohexanedicarboxylic acid(-2H))-(H2O)]·H2O}n

Conditions	Yield
In N,N-dimethyl-formamide at 120℃; for 72h; Autoclave; High pressure;	85%

cobalt(II) nitrate hexahydrate + 1,4-cyclohexanedicarboxylic acid (619-82-9) + tris[4-(1Himidazol-1-yl)-phenyl]amine + water (7732-18-5) → {[Co(tris[4-(1Himidazol-1-yl)-phenyl]amine)(trans-1,4-cyclohexanedicarboxylic acid(-2H))(H2O)]·H2O}n

Conditions	Yield
In N,N-dimethyl-formamide at 120℃; for 72h; Autoclave; High pressure;	80%

1,4-cyclohexanedicarboxylic acid (619-82-9) + 6-[(4-hydroxyphenyl)oxy]hexyl acrylate → C23H30O7

Conditions	Yield
With dmap; 2,6-di-tert-butyl-4-methyl-phenol; diisopropyl-carbodiimide In 1-methyl-pyrrolidin-2-one at 45℃; for 16h; Inert atmosphere;	77%
With dmap; 3,5-dibutyl-4-hydroxytoluene; diisopropyl-carbodiimide In 1-methyl-pyrrolidin-2-one at 45℃; for 15h;	75%
Stage #1: trans-hexahydroterephthalic acid With methanesulfonyl chloride; triethylamine In tetrahydrofuran at 20 - 30℃; for 2.16667h; Inert atmosphere; Stage #2: 6-[(4-hydroxyphenyl)oxy]hexyl acrylate With dmap; triethylamine In tetrahydrofuran at 15 - 30℃; for 2.16667h;	65%

1,4-cyclohexanedicarboxylic acid (619-82-9) + C13H16O4 → C21H26O7

Conditions	Yield
With dmap; 3,5-dibutyl-4-hydroxytoluene; diisopropyl-carbodiimide In 1-methyl-pyrrolidin-2-one at 45℃; for 15h;	77%

1,4-cyclohexanedicarboxylic acid (619-82-9) + N-{[2-(4-methoxy-phenyl)-ethylcarbamoyl]-methyl}-2-[({{[2-(4-methoxy-phenyl)-ethylcarbamoyl]-methyl}-[(3,4,5-trimethoxy-benzylcarbamoyl)-methyl]-carbamoyl}-methyl)-amino]-N-[(3,4,5-trimethoxy-benzylcarbamoyl)-methyl]-acetamide; hydrochloride → C108H138N14O30

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In N,N-dimethyl-formamide at 25℃; for 16h; Condensation;	76%

2,5-Dihydroxybenzaldehyde (1194-98-5) + 1,4-cyclohexanedicarboxylic acid (619-82-9) → C22H20O8

Conditions	Yield
With dmap; diisopropyl-carbodiimide In chloroform at 15 - 25℃; for 6h; Inert atmosphere;	75.1%
With dmap; diisopropyl-carbodiimide In chloroform at 15 - 25℃; for 6h; Inert atmosphere;	18 g

1,4-cyclohexanedicarboxylic acid (619-82-9) + tributyltin chloride (1461-22-9) → [((n-Bu)3Sn)2(trans-1,4-cyclohexanedicarboxylate)]

Conditions	Yield
With sodium ethoxide In benzene Schlenk; ligand (1 mmol) and sodium ethoxide (2 mmol) in benzene stirredfor 10 min, Sn compd. (2 mmol) added, stirred for 12 h at 40°C; filtered, concd., pptd., recrystd. (Et2O), elem. anal.;	75%

1,4-cyclohexanedicarboxylic acid (619-82-9) + tribenzyltin(IV) chloride (3151-41-5) → [((PhCH2)3Sn)2(trans-1,4-cyclohexanedicarboxylate)]

Conditions	Yield
With sodium ethoxide In benzene Schlenk; ligand (1 mmol) and sodium ethoxide (2 mmol) in benzene stirredfor 10 min, Sn compd. (2 mmol) added, stirred for 12 h at 40°C; filtered, concd., pptd., recrystd. (Et2O), elem. anal.;	75%

Re2(O2CCH3)Cl4(dppm)2 + ethanol (64-17-5) + 1,4-cyclohexanedicarboxylic acid (619-82-9) → cis-Re2Cl4(μ-dppm)2(μ-O2CC6H11CO2Et)*2EtOH

Conditions	Yield
In ethanol mixt. of Re-complex and ligand was refluxed in EtOH for 3 ds under N2; filtered, washed with EtOH and Et2O; elem. anal.;	74%

1,4-cyclohexanedicarboxylic acid (619-82-9) + C15H18O5 → C23H28O8

Conditions	Yield
With dmap; 3,5-dibutyl-4-hydroxytoluene; diisopropyl-carbodiimide In 1-methyl-pyrrolidin-2-one at 45℃; for 16h;	73%

1,4-cyclohexanedicarboxylic acid (619-82-9) + triphenyltin chloride (639-58-7) → [(Ph3Sn)2(trans-1,4-cyclohexanedicarboxylate)]

Conditions	Yield
With sodium ethoxide In benzene Schlenk; ligand (1 mmol) and sodium ethoxide (2 mmol) in benzene stirredfor 10 min, Sn compd. (2 mmol) added, stirred for 12 h at 40°C; filtered, concd., pptd., recrystd. (Et2O), elem. anal.;	71%

1,4-cyclohexanedicarboxylic acid (619-82-9) + aluminium(III) chloride hexahydrate → [Al(OH)(trans-1,4-cyclohexanedicarboxylate)]*H2O (1447716-31-5)

Conditions	Yield
With pyridine In water; N,N-dimethyl-d6-formamide at 130℃; for 12h; Concentration; Reagent/catalyst; Solvent; Autoclave; High pressure;	71%

1,4-cyclohexanedicarboxylic acid (619-82-9) + dimethyltin oxide (2273-45-2) → C8H10O4(2-)*2CH3(1-)*Sn(4+)

Conditions	Yield
In ethanol; toluene for 8h; Reflux; Dean-Stark;	71%

hexaaquanickel(II) nitrate + 1,4-cyclohexanedicarboxylic acid (619-82-9) → [Ni(H2O)4(μ2-trans-1,4-cyclohexanedicarboxylato)]

Conditions	Yield
With NaOH In water High Pressure; a soln. of a mixt. of cis- and trans-1,4-cyclohexanedicarboxylic acid (65/35) or only the trans isomer with NaOH in H2O added to a soln. of Ni complex, sealed, heated to 100°C for 1 d in an autoclave; cooled, crystals washed with H2O and acetone, dried in air; elem. anal.;	70%

cadmium(II) nitrate tetrhydrate + 1,4-cyclohexanedicarboxylic acid (619-82-9) + trans-1,2-bis(pyridin-4-yl)ethene (13362-78-2) → [Cd2(trans-1,4-e,e-cyclohexanedicarboxylate)(trans-1,4-a,a-cyclohexanedicarboxylate)((E)-1,2-bis(4-pyridyl)ethylene)2]n

Conditions	Yield
With KOH In water High Pressure; (C6H10)(COOH)2 (0.46 mmol), KOH (0.93 mmol), Cd(NO3)2*4H2O (0.46 mmol), and (C5H4N)2C2H2 (0.46 mmol) suspended in H2O; heated in pressure tube (120°C, 4 d);	70%
With KOH In ethanol; water (C6H10)(COOH)2 (0.46 mmol) dissolved in EtOH containing KOH (0.93 mmol);soln. of Cd(NO3)2*4H2O (0.46 mmol) and (C5H4N)2C2H2 (0.46 mmol) in EtOH -H2O (7:1) added; evapd. (4 d, room temp.); elem. anal.;	44%

Upstream product

• 865-50-9 iodomethane-d3 
• 105-08-8 bis-1,4-(hydroxymethyl)cyclohexane 
• 75-03-6 ethyl iodide 
• 94-60-0 dimethyl 1,4-cyclohexane dicarboxylate 
• 100-21-0 terephthalic acid 
• 120-61-6 1,4-benzenedicarboxylic acid dimethyl ester 
• 619-81-8 cis-cyclohexane-1,4-dicarboxylic acid 
• 3399-22-2 dimethyl 1,4-cyclohexanedicarboxylate 
• 2205-27-8 cyclohex-1-ene-1,4-dicarboxylic acid 
• 1459-30-9 cyclohexane-1,1,4-tricarboxylic acid 
• 3919-11-7 trans-Cyclohex-2-ene-1,4-dicarboxylic acid 
• 153032-61-2 1,1,4,4-Cyclohexanetetracarboxylic acid 
• 79-37-8 oxalyl dichloride 
• 2719-27-9 cyclohexanylcarbonyl chloride 

Downstream Products

• 735331-42-7 cyclohexane-1,4-dicarboxylic acid dipentafluorophenylester 
• 589-90-2 1,4 dimethylcyclohexane 
• 937802-15-8 divinyl cyclohexane-1,4-dicarboxylate 
• 1234477-64-5 C₂₆H₃₈FN₃O₆ 
• 1270019-99-2 (cyclohexane-1,4-dicarboxylate)(11-fluoro-dipyrido[3,2-a:2',3'-c]phenazine)lead(II) 
• 18720-35-9 bicyclo[2.2.2]octane-1,4-dicarboxylic acid monomethyl ester 

Relevant academic research and scientific papers

PRODUCTION METHOD FOR 1,4-CYCLOHEXANEDICARBOXYLIC ACID DERIVATIVE, 1,4-DICYANOCYCLOHEXANE AND 1,4-BIS(AMINOMETHYL)CYCLOHEXANE

A production method for producing a 1,4-cyclohexanedicarboxylic acid derivative, involves subjecting an aqueous ammonia solution of 1,4-cyclohexanedicarboxylic acid to heat concentration, thereby precipitating a 1,4-cyclohexanedicarboxylic acid derivative as a crystal.

Highly-efficient Ru/Al-SBA-15 catalysts with strong Lewis acid sites for the water-assisted hydrogenation of: P -phthalic acid

Ruthenium nanoparticles supported onto aluminum-doped mesoporous silica catalysts (Ru/Al-SBA-15) are fabricated using hydrothermal and impregnation methods for catalysis application. The Ru/Al-SBA-15-3 catalyst at a Si/Al molar ratio of 3 exhibited excellent catalytic performance for the hydrogenation of p-phthalic acid with high conversion efficiency (100.0%) and cis-isomer selectivity (84.0%) in water. Moreover, this system displays exceptional stability and recyclability through preserving the conversion efficiency, as well as a cis-isomer selectivity of 90.2 and 83.3%, respectively, after reusing it fourteen times. Such an exceptional system can also be ideal for the hydrogenation of aromatic dicarboxylic acids and their ester derivatives in water. Strong Lewis acid sites due to doped Al species play significant roles in the hydrogenation reaction. Moreover, isotope labeling studies indicated that water molecules effectively participated in the hydrogenation reaction. Hydrogen and water contributed half of the hydrogen atoms for this hydrogenation reaction. In the end, a plausible mechanistic pathway for the hydrogenation of p-phthalic acid using the Ru/Al-SBA-15-3 catalyst in water is proposed.

Catalyst for aqueous phase catalytic hydrogenation of phthalic acids and ester derivatives thereof and preparation method and application thereof

The invention discloses a catalyst for aqueous phase catalytic hydrogenation of phthalic acids and ester derivatives thereof, a preparation method and application thereof. The catalyst adopts an acidic composite carrier of aluminum-doped ordered mesoporous silica, and combines specific Si/Al, ordered mesoporous size and active component loading capacity to realize catalytic hydrogenation of phthalic acids and ester derivatives thereof in the water phase to prepare corresponding cyclohexanedicarboxylic acids and derivatives thereof. The catalyst is low in raw material cost, simple in preparation process and lower in noble metal loading capacity, wherein the catalytic reaction temperature is 40-100 DEG C, the hydrogen pressure is 3-6MPa, the reaction time is 0.2-3h, the conditions are mild,the solvent is pollution-free and the catalytic efficiency is high.

POWDERY 1,4-CYCLOHEXANEDICARBOXYLIC ACID

An object of the present invention is to provide a powder of high-purity 1,4-cyclohexanedicarboxylic acid with excellent powder flowability. The invention provides a powder of high-purity 1,4-cyclohexanedicarboxylic acid having particle size distributions (volume basis) such that D10 is within a range of 5 to 55 μm, D50 is within a range of 40 to 200 μm, and D90 is within a range of 170 to 800 μm; and having an aerated bulk density of 0.4 to 0.8 g/cm3, a packed bulk density of 0.5 to 1.0 g/cm3, and a compressibility of 10 to 23%.

METHOD FOR PRODUCING 1,4-DICYANOCYCLOHEXANE, 1,4-BIS(AMINOMETHYL)CYCLOHEXANE AND 1,4-CYCLOHEXANEDICARBOXYLIC ACID

A method for producing 1,4-dicyanocyclohexane, having a step of obtaining 1,4-dicyanocyclohexane by subjecting a heated concentrate of an aqueous ammonia solution of 1,4-cyclohexanedicarboxylic acid to a cyanation reaction.

Method for synthesizing cyclohexanecarboxylic acid by catalyzing hydrogenation of benzene rings through rubidium-gallium-loaded catalytic material

The invention relates to the fine chemical engineering field and particularly relates to a method for synthesizing cyclohexanecarboxylic acid by catalyzing hydrogenation of benzene rings through a rubidium-gallium-loaded catalytic material. According to the method, aromatic ring carboxylic acid is catalyzed by virtue of the rubidium-gallium-loaded catalytic material in deionized water and generates selective addition reaction with hydrogen at a low temperature and a relatively low pressure so as to generate cyclohexanecarboxylic acid; the reaction temperature is low, the reaction pressure is lower than that in the prior art, no organic solvent is adopted, the side reactions are few, and the product is conveniently purified, and the method is suitable for industrial production; and the prepared rubidium-gallium-loaded catalytic material can be recycled, is high in catalytic activity and strong in selectivity and is a very promising novel catalytic material.

Catalytic hydrogenation products of aromatic and aliphatic dicarboxylic acids

Hydrogenation of aromatic dicarboxylic acids gave 100 % selectivity to respective cyclohexane dicarboxylic acid with 5 % Pd/C catalyst. 5 % Ru/C catalyst was observed to give over hydrogenation products at 493 K and at lower temperature (453 K) the selectivity for cyclohexane dicarboxylic acids was increased. Hydrogenation of phthalic acid with Ru-Sn/Al2O3 catalyst was observed to give phthalide instead of 1,2-benzene dimethanol or 2-hydroxy methyl benzoic acid. Ru-Sn/Al2O3 catalyst selectively hydrogenated the carboxylic group of cyclohexane dicarboxylic acids to give cyclohexane dimethanol. Use of proper catalysts and reaction conditions resulted in desired products.

PREPARATION METHOD OF 1,4-CYCLOHEXANEDICARBOXYLIC ACID AND PREPARATION METHOD OF 1,4-CYCLOHEXANEDIMETHANOL

The present invention relates to a method for producing 1,4-cyclohexanedicarboxylic acid and a method for producing 1,4-cyclohexanedimethanol. According to the present invention, the method ensures high conversion rates by allowing most of the reactants to participate in a reaction, improves economic feasibility and efficiency in the reaction by simplifying a reaction process, achieves high selectivity by minimizing by-products within a short period of time, and stably controls flow rate of reactants and products. To this end, the method for producing 1,4-cyclohexanedicarboxylic acid includes a step of bringing terephthalic acid and hydrogen gas into contact via counter current in the presence of a metal catalyst which is immobilized on a silica carrier and contains a palladium (Pd) compound.COPYRIGHT KIPO 2018

Synthesis of 1,4-Cyclohexanedimethanol, 1,4-Cyclohexanedicarboxylic Acid and 1,2-Cyclohexanedicarboxylates from Formaldehyde, Crotonaldehyde and Acrylate/Fumarate

Valuable polyester monomers and plasticizers—1,4-cyclohexanedimethanol (CHDM), 1,4-cyclohexanedicarboxylic acid (CHDA), and 1,2-cyclohexanedicarboxylates—have been prepared by a new strategy. The synthetic processes involve a proline-catalyzed formal [3+1+2] cycloaddition of formaldehyde, crotonaldehyde, and acrylate (or fumarate). CHDM is produced after a subsequent hydrogenation step over a commercially available Cu/Zn/Al catalyst and a one-pot hydrogenation/oxidation/hydrolysis process yields CHDA, whereas 1,2-cyclohexanedicarboxylate is obtained by a Pd/C-catalyzed tandem decarbonylation/hydrogenation step.

Preparation method for 1,4-cyclohexanedimethanol or 1,4-cyclohexanedicarboxylic acid

The invention relates to a preparation method for 1,4-cyclohexanedimethanol or 1,4-cyclohexanedicarboxylic acid. The preparation method for 1,4-cyclohexanedimethanol comprises the following steps: step 1, subjecting crotonaldehyde, formaldehyde and acrylate to a D-A cycloaddition reaction under base catalysis so as to produce ester group-substituted cyclohexene formaldehyde; and step 2, subjectinga resulting product to complete hydrogenation under the action of a transition metal catalyst to produce 1,4-cyclohexanedimethanol. The preparation method for 1,4-cyclohexanedicarboxylic acid comprises the following steps: step 1, subjecting crotonaldehyde, formaldehyde and acrylate to a D-A cycloaddition reaction under base catalysis so as to produce ester group-substituted cyclohexene formaldehyde; step 2, subjecting a double bond on the resulting product to hydrogenation so as to form an ester group-substituted cyclohexane formaldehyde or cyclohexane methanol; step 3, subjecting cyclohexane formaldehyde or cyclohexane methanol or a mixture thereof to a one-step oxidation reaction so as to form ester group-substituted cyclohexanecarboxylic acid; and step 4, carrying out hydrolysis on aresulting product of the previous step so as to produce 1,4-cyclohexanedicarboxylic acid. The invention provides novel processes for preparing the fine chemicals consisting of 1,4-cyclohexanedimethanol and 1,4-cyclohexanedicarboxylic acid from lignocellulose-based platform chemicals.