13291-61-7

Basic information

• Product Name: 1,2-Cyclohexylenedinitrilotetraacetic acid
• Synonyms: 1,2-diaminocyclohexane-n,n,n’-tetraaceticacidhydrate;n’-1,2-cyclohexanediylbis[n-(carboxymethyl)-trans-glycin;trans-1,2-diaminocyclohexanetetraacetic;trans-1,2-diaminocyclohexanetetraaceticacid;trans-cyclohexane-1,2-dinitrilotetraaceticacid;HEXAVER(R) TITRANT;CDTA;CDTA REAGENT
• CAS NO: 13291-61-7
• Molecular Formula: C₁₄H₂₂N₂O₈
• Molecular Weight: 346.33
• EINECS: 236-308-9
• Product Categories: organic amine
• Mol File: 13291-61-7.mol
• Article Data: 1

Chemical Properties

• Melting Point: 213-216 °C(lit.)
• Boiling Point: 670.8 °C at 760 mmHg
• Flash Point: 359.5 °C
• Appearance: white powder
• Density: 1.48 g/cm³
• Vapor Pressure: 0Pa at 25℃
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 1.78±0.10(Predicted)
• Water Solubility: 425.4g/L at 25℃
• Stability: Stable. Incompatible with strong oxidizing agents. Combustible.
• CAS DataBase Reference: 1,2-Cyclohexylenedinitrilotetraacetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Cyclohexylenedinitrilotetraacetic acid(13291-61-7)
• EPA Substance Registry System: 1,2-Cyclohexylenedinitrilotetraacetic acid(13291-61-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• F: 9
• Hazardous Substances Data: 13291-61-7(Hazardous Substances Data)

Usage

Chemical Properties

white powder

Uses

Different sources of media describe the Uses of 13291-61-7 differently. You can refer to the following data:
1. 1,2-Cyclohexanedinitrilotetraacetic acid
2. 1,2-Cyclohexylenedinitrilotetraacetic Acid is used as a chelating agent in the phytoextraction of Ni from contaminated soil.

Flammability and Explosibility

Notclassified

Purification Methods

Dissolve CDTA in aqueous NaOH as its disodium salt, then precipitate it by adding HCl. The free acid is filtered off and boiled with distilled water to remove traces of HCl [Bond & Jones Trans Faraday Soc 55 1310 1959]. Recrystallise it from water and dry it in vacuo.[Beilstein 13 III 10.]

Synthetic route

formaldehyd (50-00-0) + trans-1,2-Diaminocyclohexane (1121-22-8, 1436-59-5, 20439-47-8, 21436-03-3, 41013-43-8, 694-83-7) + sodium cyanide (143-33-9) → trans-1,2-Cyclohexanediaminetetraacetic acid (13291-61-7)

Conditions	Yield
With sodium hydroxide; water at 70℃; unter vermindertem Druck;

trans-1,2-Diaminocyclohexane (1121-22-8, 1436-59-5, 20439-47-8, 21436-03-3, 41013-43-8, 694-83-7) + chloroacetic acid (79-11-8) → trans-1,2-Cyclohexanediaminetetraacetic acid (13291-61-7)

Conditions	Yield
With sodium hydroxide at 90 - 95℃;

trans-1,2-Cyclohexanediaminetetraacetic acid (13291-61-7) + 1,2-diamino-benzene (95-54-5) → ortho-Bis-trans-cyclohexane

Conditions	Yield
at 140 - 180℃;	95%
In ethylene glycol at 140 - 180℃;	95%
at 180 - 200℃;

trans-1,2-Cyclohexanediaminetetraacetic acid (13291-61-7) + water (7732-18-5) + dihydrogen peroxide (7722-84-1) + titanium tetrachloride (7550-45-0) + sodium hydroxide (1310-73-2) → Na2[Ti(peroxo)(trans-cyclohexanediaminetetraacetato)] dihydrate

Conditions	Yield
In water acid dissolved in H2O at pH 6.0 with NaOH, soln. added to TiCl4, H2O2 added, pH adjusted to 5.5 (NaOH), stirred for 5 h; soln. kept in refrigerator for 5 d; elem. anal.;	95%

trans-1,2-Cyclohexanediaminetetraacetic acid (13291-61-7) + water (7732-18-5) + titanium tetrachloride (7550-45-0) → Ti(trans-cyclohexanediaminetetraacetato)(H2O) dihydrate

Conditions	Yield
With NH4OH In water acid dissolved in H2O at pH 6.0 with NH4OH, soln. added to TiCl4; ppt. collected, washed (cold H2O, ethanol); elem. anal.;	95%

trans-1,2-Cyclohexanediaminetetraacetic acid (13291-61-7) → trans-1,2-diaminocyclohexane-N,N,N',N'-tetraacetic acid dianhydride

Conditions	Yield
With pyridine; acetic anhydride at 55 - 60℃; for 3h;	94%

trans-1,2-Cyclohexanediaminetetraacetic acid (13291-61-7) + palladium dichloride → C6H10(NH(CH2COOH)2)2(2+)*PdCl4(2-)*2H2O=(C6H10(NH(CH2COOH)2)2){PdCl4}*2H2O

Conditions	Yield
With hydrogenchloride In hydrogenchloride; acetic acid a soln. of PdCl2 in aq. HCl was mixed with a soln. of the aminocarbonic acid in acetic acid, addn. of concd. HCl; slow evapd. in a water bath, recrystd. from 1 M HCl; elem. anal.;	91%

rubidium hydroxide + trans-1,2-Cyclohexanediaminetetraacetic acid (13291-61-7) + cobalt(II) carbonate (759403-02-6) → rubidium trans-1,2-cyclohexanediaminetetraacetatocobaltate(III) monohydrate

Conditions	Yield
With dihydrogen peroxide In water byproducts: CO2, H2O; water added to a mixt. of CoCO3 and ligand, mixt. heated to 70°C, 30% H2O2 added, soln. stirred at 70°C for 15 min, RbOH added, reacted for 15 min; under N2; cold EtOH added to the filtrate, mixt. stirred for 30 min at 0°C, filtered, ppt. washed with EtOH, acetone, and dried in vac. at 120°C for 16 h; elem. anal.;	90.9%

trans-1,2-Cyclohexanediaminetetraacetic acid (13291-61-7) + cobalt(II) carbonate (759403-02-6) → potassium trans-1,2-cyclohexanediaminetetraacetatocobaltate(III) monohydrate

Conditions	Yield
With potassium hydroxide; dihydrogen peroxide In water byproducts: CO2, H2O; water added to a mixt. of CoCO3 and ligand, mixt. heated to 70°C, 30% H2O2 added, soln. stirred at 70°C for 15 min, KOH added, reacted for 15 min; under N2; cold EtOH added to the filtrate, mixt. stirred for 30 min at 0°C, filtered, ppt. washed with EtOH, acetone, and dried in vac. at 120°C for 16 h; elem. anal.;	88.7%

cesium hydroxide + trans-1,2-Cyclohexanediaminetetraacetic acid (13291-61-7) + cobalt(II) carbonate (759403-02-6) → cesium trans-1,2-cyclohexanediaminetetraacetatocobaltate(III) monohydrate

Conditions	Yield
With dihydrogen peroxide In water byproducts: CO2, H2O; water added to a mixt. of CoCO3 and ligand, mixt. heated to 70°C, 30% H2O2 added, soln. stirred at 70°C for 15 min, CsOH added, reacted for 15 min; under N2; cold EtOH added to the filtrate, mixt. stirred for 30 min at 0°C, filtered, ppt. washed with EtOH, acetone, and dried in vac. at 120°C for 16 h; elem. anal.;	88.5%

trans-1,2-Cyclohexanediaminetetraacetic acid (13291-61-7) + platinum(II) chloride → C6H10(NH(CH2COOH)2)2(2+)*PtCl4(2-)*2H2O=(C6H10(NH(CH2COOH)2)2){PtCl4}*2H2O

Conditions	Yield
With hydrogenchloride In hydrogenchloride; acetic acid a soln. of PtCl2 in aq. HCl was mixed with a soln. of the aminocarbonic acid in acetic acid, addn. of concd. HCl; slow evapd. in a water bath, recrystd. from 1 M HCl; elem. anal.;	81%

manganese(IV) oxide (1313-13-9) + manganese(II) nitrate + trans-1,2-Cyclohexanediaminetetraacetic acid (13291-61-7) → K{Mn(cdta)}*2.5H2O

Conditions	Yield
molar ratio of C14H22N2O8:Mn(NO3)2=2:1, 0°C, 0.5-1 h; filtrn. of excess MnO2, addn. of an equal vol. of cold ethanol, then standing for several hours at 0°C, washing with abs. ethanol, drying in vac. at room temp.;	80%
molar ratio of C14H22N2O8:Mn(NO3)2=2:1, 0°C, 0.5-1 h; filtrn. of excess MnO2, addn. of an equal vol. of cold ethanol, then standing for several hours at 0°C, washing with abs. ethanol, drying in vac. at room temp.;	80%
molar ratio of C14H22N2O8:Mn(NO3)2=2:1, 0°C, 0.5-1 h; filtrn. of excess MnO2, addn. of an equal vol. of cold ethanol, then standing for several hours at 0°C, washing with abs. ethanol;
molar ratio of C14H22N2O8:Mn(NO3)2=2:1, 0°C, 0.5-1 h; filtrn. of excess MnO2, addn. of an equal vol. of cold ethanol, then standing for several hours at 0°C, washing with abs. ethanol;

trans-1,2-Cyclohexanediaminetetraacetic acid (13291-61-7) + vanadium(III) chloride (7718-98-1) → potassium (trans-1,2-cyclohexanediamine-N,N,N',N'-tetraacetato)aquavanadate(III)*2H2O

Conditions	Yield
With K2CO3; KHCO3 In water addn. of K2CO3 to a suspn. of H4cydta in water, then addn. of VCl3 and KHCO3 (under N2); reducing of volume by evapn., filtn., washing with water and ethanol, elem. anal.;	69%

terbium(III) perchlorate + trans-1,2-Cyclohexanediaminetetraacetic acid (13291-61-7) + cobalt(II) perchlorate hexahydrate → [Tb2Co2(trans-1,2-diaminocyclohexane-N,N,N',N'-tetraacetate)2(μ3-OH)2(H2O)6].6H2O

Conditions	Yield
With sodium hydroxide In water at 90℃; for 24h; pH=5.4; Sealed tube;	52%

dodecatungstosilic acid + samarium(III) chloride hexahydrate + trans-1,2-Cyclohexanediaminetetraacetic acid (13291-61-7) → [Sm2(H2CyDTA)2(H2O)12][H2SiW12O40]·17H2O

Conditions	Yield
Stage #1: dodecatungstosilic acid; samarium(III) chloride hexahydrate In water at 20℃; for 0.5h; Stage #2: trans-1,2-Cyclohexanediaminetetraacetic acid In water at 60℃; for 2h; pH=1.9;	42%

gadolinium(III) perchlorate + trans-1,2-Cyclohexanediaminetetraacetic acid (13291-61-7) + cobalt(II) perchlorate hexahydrate → [Gd2Co2(trans-1,2-diaminocyclohexane-N,N,N',N'-tetraacetate)2(μ3-OH)2(H2O)6].6H2O

Conditions	Yield
With sodium hydroxide In water at 90℃; for 24h; pH=5.4; Sealed tube;	42%

4NH4(1+)*SiW12O40(4-)*4H2O=(NH4)4(SiW12O40)*4H2O + trans-1,2-Cyclohexanediaminetetraacetic acid (13291-61-7) + water (7732-18-5) + zinc(II) acetate dihydrate (5970-45-6) → (NH4)2[Zn5(trans-N,N,N',N'-1,2-cyclohexanediaminotetraacetato)2(H2O)16][SiW12O40]*8H2O

Conditions	Yield
With NaOH In water Zn- and Si-contg. compds. (1.0 mmol and 0.2 mmol, resp.) were dissolved in H2O; the soln. was stirred for 0.5 h at 85°C; addn. of hot soln. of a ligand (0.75 mmol); cooling; pH = 3.4 (NaOH); stirring for 0.5 hat 85°C; the soln. was filtered; the filtrate was allowed to evap. in air at roomtemp.; crystals were obtained after 2 wk; elem. anal.;	41%

dodecatungstosilic acid + yttrium(III) chloride hexahydrate + trans-1,2-Cyclohexanediaminetetraacetic acid (13291-61-7) → [Y2(H2CyDTA)2(H2O)12][H2SiW12O40]·14H2O

Conditions	Yield
Stage #1: dodecatungstosilic acid; yttrium(III) chloride hexahydrate In water at 20℃; for 0.5h; Stage #2: trans-1,2-Cyclohexanediaminetetraacetic acid With sodium hydroxide In water at 60℃; for 2h; pH=3.2;	41%

4NH4(1+)*SiW12O40(4-)*4H2O=(NH4)4(SiW12O40)*4H2O + trans-1,2-Cyclohexanediaminetetraacetic acid (13291-61-7) + water (7732-18-5) + strontium chloride → (NH4)4[Sr3(trans-N,N,N',N'-1,2-cyclohexanediaminotetraacetic acid-3H)2(H2O)14][SiW12O40]*2H2O

Conditions	Yield
With NaOH In water Sr-contg. compd. (1.0 mmol) was dissolved in H2O; addn. of a soln. of a ligand (0.10 mmol) and Si-contg. compd. (0.10 mmol); pH = 1.8 (NaOH); stirring for 1 h at 70°C; the soln. was filtered; the filtrate was allowed to evap. in air at roomtemp.; crystals were obtained after 1 wk; elem. anal.;	39%

cadmium(II) sulfate*8/3H2O + 4NH4(1+)*SiW12O40(4-)*4H2O=(NH4)4(SiW12O40)*4H2O + trans-1,2-Cyclohexanediaminetetraacetic acid (13291-61-7) → (NH4)4[Cd4(trans-N,N,N',N'-1,2-cyclohexanediaminotetraacetato)2(H2O)8][SiW12O40]*6H2O

Conditions	Yield
With NaOH In water Cd- and Si-contg. compds. (1.0 mmol and 0.2 mmol, resp.) were dissolved in H2O; the soln. was stirred for 0.5 h at 85°C; addn. of hot soln. of a ligand (0.5 mmol); cooling; pH = 4.4 (NaOH); stirring for 0.5 h at 85°C; the soln. was filtered; the filtrate was allowed to evap. in air at roomtemp.; crystals were obtained after 10 d; elem. anal.;	39%

dodecatungstosilic acid + europium(III) chloride hexahydrate + trans-1,2-Cyclohexanediaminetetraacetic acid (13291-61-7) → [Eu2(H2CyDTA)2(H2O)12][H2SiW12O40]·17H2O

Conditions	Yield
Stage #1: dodecatungstosilic acid; europium(III) chloride hexahydrate In water at 20℃; for 0.5h; Stage #2: trans-1,2-Cyclohexanediaminetetraacetic acid In water at 60℃; for 2h; pH=1.8;	39%

nickel(II) chloride hexahydrate + 4NH4(1+)*SiW12O40(4-)*4H2O=(NH4)4(SiW12O40)*4H2O + trans-1,2-Cyclohexanediaminetetraacetic acid (13291-61-7) + sodium hydroxide (1310-73-2) → (NH4)3[Ni4Na(H2O)10(trans-N,N,N',N'-1,2-cyclohexanediaminotetraacetato)2][SiW12O40]*10H2O

Conditions	Yield
In water Ni- and Si-contg. compds. (1.0 mmol and 0.2 mmol, resp.) were dissolved in H2O; the soln. was stirred for 0.5 h at 85°C; addn. of hot soln. of a ligand (0.75 mmol); cooling; pH = 3.4 (NaOH); stirring for 0.5 hat 85°C; the soln. was filtered; the filtrate was allowed to evap. in air at roomtemp.; crystals were obtained after 3 wk; elem. anal.;	38%

lanthanum(III) perchlorate + trans-1,2-Cyclohexanediaminetetraacetic acid (13291-61-7) + cobalt(II) perchlorate hexahydrate + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → [La2Co2(trans-1,2-diaminocyclohexane-N,N,N',N'-tetraacetate)2(μ4-OH)(DMF)2(H2O)6].ClO4.1.5H2O

Conditions	Yield
With sodium hydroxide In water at 90℃; for 24h; pH=5.4; Sealed tube;	38%

gadolinium(III) perchlorate + trans-1,2-Cyclohexanediaminetetraacetic acid (13291-61-7) + cobalt(II) perchlorate hexahydrate + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → [Gd2Co2(trans-1,2-diaminocyclohexane-N,N,N',N'-tetraacetate)2(μ4-OH)(DMF)2(H2O)6]*ClO4*1.5H2O

Conditions	Yield
With sodium hydroxide In water at 90℃; for 24h; pH=5.4; Sealed tube;	36%

Upstream product

• 50-00-0 formaldehyd 
• 1121-22-8 trans-1,2-Diaminocyclohexane 
• 143-33-9 sodium cyanide 
• 79-11-8 chloroacetic acid 

Downstream Products

• 124705-99-3 (R,R)-2,6-bis(pyrrolidin-2-yl)pyridine 
• 124706-02-1 (R,S)-2,6-bis(pyrrolidin-2-yl)pyridine 
• 124706-04-3 (S,S)-2,6-bis(pyrrolidin-2-yl)pyridine 

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