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Cas Database

124-09-4

124-09-4

Identification

  • Product Name:1,6-Hexanediamine

  • CAS Number: 124-09-4

  • EINECS:204-679-6

  • Molecular Weight:116.206

  • Molecular Formula: C6H16N2

  • HS Code:2921229000

  • Mol File:124-09-4.mol

Synonyms:1,6-Diamino-n-hexane;1,6-Diaminohexane;Advancure;HMDA;Hexamethylenediamine;Hexylenediamine;Hi Perm;NSC 9257;RT Advancure HD;V 1;a,w-Hexanediamine;

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Safety information and MSDS view more

  • Pictogram(s):CorrosiveC

  • Hazard Codes: C:Corrosive;

  • Signal Word:Danger

  • Hazard Statement:H302 Harmful if swallowedH312 Harmful in contact with skin H314 Causes severe skin burns and eye damage H335 May cause respiratory irritation

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer for medical attention. In case of skin contact Rinse skin with plenty of water or shower. Refer for medical attention . In case of eye contact First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention. If swallowed Rest. Refer for medical attention . See Notes. Vapors cause irritation of eyes and respiratory tract. Liquid irritates eyes and skin, may cause dermatitis. (USCG, 1999)Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. (ERG, 2016) For immediate first aid: Ensure that adequate decontamination has been carried out. If victim is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep victim quiet and maintain normal body temperature. Obtain medical attention. /Organic bases\amines and related compounds/

  • Fire-fighting measures: Suitable extinguishing media Extinguish with water, foam, dry chemical, or carbon dioxide. Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form. (ERG, 2016)Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form. (ERG, 2016) Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Personal protection: complete protective clothing including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Collect leaking and spilled liquid in sealable containers as far as possible. Carefully collect remainder. Then store and dispose of according to local regulations. TREATMENT OF WASTE WATER CONTAINING HEXAMETHYLENEDIAMINE FROM POLYAMIDE MFG IN REVERSE OSMOSIS APPARATUS WITH CELLULOSE ACETATE MEMBRANES WAS STUDIED TO DETERMINE THE EFFECT OF HCL ADDITION ON TRANSPORT OF COMPONENTS OF THE SOLN THROUGH A MEMBRANE & TO ASSESS THE POSSIBILITY OF CHANGING THE PH OF THE CONCN FORMED IN THE APPARATUS.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Separated from strong oxidants and strong acids. Well closed.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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Relevant articles and documentsAll total 118 Articles be found

Supported Ni catalyst for liquid phase hydrogenation of adiponitrile to 6-Aminocapronitrile and hexamethyenediamine

Wang, Chengqiang,Jia, Zekun,Zhen, Bin,Han, Minghan

, (2018)

Supported Ni catalysts prepared under different conditions, for liquid phase hydrogenation of adiponitrile (ADN) to 6-aminocapronitrile (ACN) and hexamethyenediamine (HMD), were investigated. The highly reactive imine intermediate can form condensation byproducts with primary amine products (ACN and HMD), which decreased the yield coefficient of primary amines. The catalysts support, condition of catalyst preparation and dosage of additive were studied to improve the yield. A highly dispersed Ni/SiO2 catalyst prepared by the direct reduction of Ni(NO3)2/SiO2 suppressed the condensation reactions by promoting the hydrogenation of adsorbed imines, and it gave the improved hydrogenation activity of 0.63 mol·kgcat?1·min?1 and primary amine selectivity of 94% when NaOH was added into the reactor.

Zirconium-hydride-catalyzed site-selective hydroboration of amides for the synthesis of amines: Mechanism, scope, and application

Han, Bo,Jiao, Haijun,Wu, Lipeng,Zhang, Jiong

, p. 2059 - 2067 (2021/09/02)

Developing mild and efficient catalytic methods for the selective synthesis of amines is a longstanding research objective. In this respect, catalytic deoxygenative amide reduction has proven to be promising but challenging, as this approach necessitates selective C–O bond cleavage. Herein, we report the selective hydroboration of primary, secondary, and tertiary amides at room temperature catalyzed by an earth-abundant-metal catalyst, Zr-H, for accessing diverse amines. Various readily reducible functional groups, such as esters, alkynes, and alkenes, were well tolerated. Furthermore, the methodology was extended to the synthesis of bio- and drug-derived amines. Detailed mechanistic studies revealed a reaction pathway entailing aldehyde and amido complex formation via an unusual C–N bond cleavage-reformation process, followed by C–O bond cleavage.

Aluminum Metal-Organic Framework-Ligated Single-Site Nickel(II)-Hydride for Heterogeneous Chemoselective Catalysis

Antil, Neha,Kumar, Ajay,Akhtar, Naved,Newar, Rajashree,Begum, Wahida,Dwivedi, Ashutosh,Manna, Kuntal

, p. 3943 - 3957 (2021/04/12)

The development of chemoselective and heterogeneous earth-abundant metal catalysts is essential for environmentally friendly chemical synthesis. We report a highly efficient, chemoselective, and reusable single-site nickel(II) hydride catalyst based on robust and porous aluminum metal-organic frameworks (MOFs) (DUT-5) for hydrogenation of nitro and nitrile compounds to the corresponding amines and hydrogenolysis of aryl ethers under mild conditions. The nickel-hydride catalyst was prepared by the metalation of aluminum hydroxide secondary building units (SBUs) of DUT-5 having the formula of Al(μ2-OH)(bpdc) (bpdc = 4,4′-biphenyldicarboxylate) with NiBr2 followed by a reaction with NaEt3BH. DUT-5-NiH has a broad substrate scope with excellent functional group tolerance in the hydrogenation of aromatic and aliphatic nitro and nitrile compounds under 1 bar H2 and could be recycled and reused at least 10 times. By changing the reaction conditions of the hydrogenation of nitriles, symmetric or unsymmetric secondary amines were also afforded selectively. The experimental and computational studies suggested reversible nitrile coordination to nickel followed by 1,2-insertion of coordinated nitrile into the nickel-hydride bond occurring in the turnover-limiting step. In addition, DUT-5-NiH is also an active catalyst for chemoselective hydrogenolysis of carbon-oxygen bonds in aryl ethers to afford hydrocarbons under atmospheric hydrogen in the absence of any base, which is important for the generation of fuels from biomass. This work highlights the potential of MOF-based single-site earth-abundant metal catalysts for practical and eco-friendly production of chemical feedstocks and biofuels.

PROCESS FOR THE PREPARATION OF HEXAMETHYLENEDIAMINE BY HYDROGENATION OF ADIPONITRILE WITH REDUCED FORMATION OF DIAMINOCYCLOHEXANE

-

Page/Page column 6; 7, (2021/10/02)

The present invention relates to a process for the preparation of hexamethylenediamine by hydrogenation of adiponitrile in the presence of a Raney nickel catalyst, wherein a Raney nickel catalyst modified by treatment with carbon monoxide or carbon dioxide in a liquid medium is used.

Method for preparing 1, 6-hexamethylenediamine from 5-hydroxymethylfurfural

-

Paragraph 140; 0146; 0148, (2021/06/06)

The invention relates to a method for preparing 1, 6-hexamethylenediamine from 5-hydroxymethylfurfural, which is characterized in that the 5-hydroxymethylfurfural is used as a raw material, and the 1, 6-hexamethylenediamine is synthesized by a two-step method under the action of a catalyst. The method comprises the following steps: 1) in a hydrogen atmosphere, reacting the raw material 5-hydroxymethylfurfural with ammonia in the presence of a reductive amination catalyst to generate 2, 5-dimethylamine tetrahydrofuran; and 2) continuing the reaction, and carrying out a ring-opening reaction on the hydrodeoxygenation catalyst to produce the target product 1, 6-hexamethylenediamine. The method is characterized in that the reductive amination catalyst in the step 1) is an M1-M2 supported multi-metal component catalyst. The method is characterized in that the hydrodeoxygenation catalyst in the step 2) is a supported catalyst, and the metal active component is selected from one or more of transition metal elements Rh, Re, Pt, Ir, Pd and Ru. The 1, 6-hexamethylenediamine is produced by using the bio-based material monomer 5-hydroxymethylfurfural as the raw material, so that the method is green and clean, the process is easy to operate, the yield is high, and a wide application prospect is provided for biomass conversion.

Method for preparing organic diamine from amino nitrile organic matter

-

Paragraph 0240-0285, (2021/10/02)

The invention provides a method for preparing organic diamine from an amino nitrile organic matter, which comprises the following steps: (1) reacting the amino nitrile organic matter with hydrogen in a solvent under the action of a catalyst to obtain a reacted material containing the organic diamine; (2) refining the reacted material to obtain crude organic diamine; and (3) adsorbing and purifying the crude organic diamine to obtain the purified organic diamine. According to the method, the amino nitrile organic matter reacts with hydrogen, the reaction selectivity and the conversion rate are high, and the high-purity organic diamine product can be obtained in the subsequent purification mode of combining refining and adsorption purification.

Process route upstream and downstream products

Process route

C<sub>14</sub>H<sub>20</sub>N<sub>6</sub>

C14H20N6

1,6-Hexanediamine
124-09-4

1,6-Hexanediamine

2-imidazolecarbaldehyde
10111-08-7

2-imidazolecarbaldehyde

Conditions
Conditions Yield
With water-d2; at 50 ℃; for 24h; Temperature;
0.26C<sub>14</sub>H<sub>18</sub>N<sub>6</sub><sup>(2-)</sup>*Zn<sup>(2+)</sup>*1.48C<sub>4</sub>H<sub>5</sub>N<sub>2</sub><sup>(1-)</sup>

0.26C14H18N6(2-)*Zn(2+)*1.48C4H5N2(1-)

1,6-Hexanediamine
124-09-4

1,6-Hexanediamine

2-methylimidazole
693-98-1

2-methylimidazole

2-imidazolecarbaldehyde
10111-08-7

2-imidazolecarbaldehyde

Conditions
Conditions Yield
With hydrogen chloride; In dimethylsulfoxide-d6;
0.23C<sub>14</sub>H<sub>18</sub>N<sub>6</sub><sup>(2-)</sup>*Zn<sup>(2+)</sup>*1.54C<sub>4</sub>H<sub>5</sub>N<sub>2</sub><sup>(1-)</sup>

0.23C14H18N6(2-)*Zn(2+)*1.54C4H5N2(1-)

1,6-Hexanediamine
124-09-4

1,6-Hexanediamine

2-methylimidazole
693-98-1

2-methylimidazole

2-imidazolecarbaldehyde
10111-08-7

2-imidazolecarbaldehyde

Conditions
Conditions Yield
With hydrogen chloride; In dimethylsulfoxide-d6;
0.18C<sub>14</sub>H<sub>18</sub>N<sub>6</sub><sup>(2-)</sup>*Zn<sup>(2+)</sup>*1.64C<sub>4</sub>H<sub>5</sub>N<sub>2</sub><sup>(1-)</sup>

0.18C14H18N6(2-)*Zn(2+)*1.64C4H5N2(1-)

1,6-Hexanediamine
124-09-4

1,6-Hexanediamine

2-methylimidazole
693-98-1

2-methylimidazole

2-imidazolecarbaldehyde
10111-08-7

2-imidazolecarbaldehyde

Conditions
Conditions Yield
With hydrogen chloride; In dimethylsulfoxide-d6;
0.12C<sub>14</sub>H<sub>18</sub>N<sub>6</sub><sup>(2-)</sup>*Zn<sup>(2+)</sup>*1.76C<sub>4</sub>H<sub>5</sub>N<sub>2</sub><sup>(1-)</sup>

0.12C14H18N6(2-)*Zn(2+)*1.76C4H5N2(1-)

1,6-Hexanediamine
124-09-4

1,6-Hexanediamine

2-methylimidazole
693-98-1

2-methylimidazole

2-imidazolecarbaldehyde
10111-08-7

2-imidazolecarbaldehyde

Conditions
Conditions Yield
With hydrogen chloride; In dimethylsulfoxide-d6;
0.08C<sub>14</sub>H<sub>18</sub>N<sub>6</sub><sup>(2-)</sup>*Zn<sup>(2+)</sup>*1.84C<sub>4</sub>H<sub>5</sub>N<sub>2</sub><sup>(1-)</sup>

0.08C14H18N6(2-)*Zn(2+)*1.84C4H5N2(1-)

1,6-Hexanediamine
124-09-4

1,6-Hexanediamine

2-methylimidazole
693-98-1

2-methylimidazole

2-imidazolecarbaldehyde
10111-08-7

2-imidazolecarbaldehyde

Conditions
Conditions Yield
With hydrogen chloride; In dimethylsulfoxide-d6;
hexanedinitrile
111-69-3

hexanedinitrile

hexamethylene imine
111-49-9

hexamethylene imine

1,6-Hexanediamine
124-09-4

1,6-Hexanediamine

1-amino-5-cyanopentane
2432-74-8

1-amino-5-cyanopentane

Conditions
Conditions Yield
With hydrogen; aluminum oxide; nickel; at 169.9 ℃; under 760 Torr; Product distribution; varying space velocity of catalysts;
With hydrogen; nickel monophosphide; silica gel; In ethanol; at 199.85 ℃; under 760 Torr; Further Variations:; Catalysts; Product distribution;
19 % Chromat.
65 % Chromat.
16 % Chromat.
With potassium hydroxide; hydrogen; [Ni0.60Mg0.15Al0.25(OH)2](CO32-)0.09(NO3-)0.18; at 79.85 ℃; under 18751.5 Torr; Further Variations:; Catalysts; Reagents; Temperatures; Product distribution;
With hydrogen;
With Ni-doped silica; hydrogen; sodium hydroxide; In methanol; at 80 ℃; for 1.33333h; under 22502.3 Torr; Time; Reagent/catalyst; Catalytic behavior; Autoclave;
With hydrogen; In ethanol; at 119.84 ℃; for 6h; under 15001.5 Torr; Reagent/catalyst; Temperature; Autoclave;
With sepiolite; hydrogen; In ethanol; at 149.84 ℃; for 6h; under 15001.5 Torr; Reagent/catalyst; Temperature;
hexanedinitrile
111-69-3

hexanedinitrile

1,6-Hexanediamine
124-09-4

1,6-Hexanediamine

1-amino-5-cyanopentane
2432-74-8

1-amino-5-cyanopentane

Conditions
Conditions Yield
With Rh/Al2O3; hydrogen; In ethanol; at 80 ℃; for 6h;
75.6%
24.4%
With hydrogen; active elemental iron component; In ammonia; at 70 - 220 ℃; under 75007.5 - 300030 Torr;
hexanedinitrile; With potassium hydroxide; hydrogen; nickel; at 50 ℃; under 15001.5 Torr;
With phosphoric acid; Purification / work up;
With ammonia; hydrogen; iron; at 150 ℃; for 1.16667h; under 232523 Torr;
With tetramethyl ammoniumhydroxide; ammonia; hydrogen; iron; at 150 ℃; for 2h; under 232523 Torr;
With tetraethylammoniumcyanide; ammonia; hydrogen; iron; at 150 ℃; for 3h; under 232523 Torr;
With ammonia; hydrogen; tetra-n-butylammonium cyanide; iron; at 150 ℃; for 5.25h; under 232523 Torr;
With ethylimidazolium chloride; hydrogen; In toluene; at 100 ℃; for 12h; under 75007.5 Torr; Conversion of starting material;
With hydrogen; In toluene; at 100 ℃; for 6h; under 75007.5 Torr; Conversion of starting material;
With 3-methylimidazolinium hydrogensulfate; hydrogen; 3% Ru/C; In toluene; at 100 ℃; for 18h; under 75007.5 Torr; Conversion of starting material;
With ammonia; hydrogen; Raney nickel, Cs2CO3-modified; at 60 ℃; for 12h; under 27752.8 Torr; Product distribution / selectivity;
With ammonia; hydrogen; Cr- and Fe-doped Raney nickel. Cs2CO3-modified; at 60 ℃; for 8 - 14h; under 27752.8 Torr; Product distribution / selectivity;
With ammonia; hydrogen; Cr- and Fe-doped Raney nickel; at 60 ℃; for 4h; under 27752.8 Torr; Product distribution / selectivity;
With ammonia; hydrogen; Raney nickel, Ca(OAc)2-modified; at 60 ℃; for 8h; under 27752.8 Torr; Product distribution / selectivity;
With ammonia; hydrogen; Raney nickel, K2CO3-modified; at 60 ℃; for 10h; under 27752.8 Torr; Product distribution / selectivity;
With ammonia; hydrogen; Raney nickel, Li2CO3-modified; at 60 ℃; for 8h; under 27752.8 Torr; Product distribution / selectivity;
With ammonia; hydrogen; Raney nickel, Mg(OAc)2-modified; at 60 ℃; for 6h; under 27752.8 Torr; Product distribution / selectivity;
With ammonia; hydrogen; nickel; at 60 ℃; for 8h; under 27752.8 Torr; Product distribution / selectivity;
With ammonia; hydrogen; nickel; caesium carbonate; at 60 ℃; for 12h; under 27752.8 Torr; Product distribution / selectivity;
With ammonia; hydrogen; nickel; potassium carbonate; at 60 ℃; for 10h; under 27752.8 Torr; Product distribution / selectivity;
With ammonia; hydrogen; calcium acetate; nickel; at 60 ℃; for 8h; under 27752.8 Torr; Product distribution / selectivity;
With ammonia; hydrogen; magnesium acetate; nickel; at 60 ℃; for 6h; under 27752.8 Torr; Product distribution / selectivity;
With ammonia; hydrogen; lithium carbonate; nickel; at 60 ℃; for 8h; under 27752.8 Torr; Product distribution / selectivity;
hexanedinitrile
111-69-3

hexanedinitrile

hexamethylene imine
111-49-9

hexamethylene imine

1,6-Hexanediamine
124-09-4

1,6-Hexanediamine

di(5-cyanopentyl)-amine

di(5-cyanopentyl)-amine

1-amino-5-cyanopentane
2432-74-8

1-amino-5-cyanopentane

1,8,15-triazapentadecane
143-23-7

1,8,15-triazapentadecane

Conditions
Conditions Yield
With 1-butyl-3-methylimidazolium hydroxide; hydrogen; In ethanol; at 349.84 ℃; for 6h; under 15001.5 Torr; Reagent/catalyst; Temperature; Pressure; Time; Flow reactor; Sealed tube; Inert atmosphere; Ionic liquid;
trans,trans-mucononitrile
5867-88-9

trans,trans-mucononitrile

1,6-Hexanediamine
124-09-4

1,6-Hexanediamine

hexanedinitrile
111-69-3

hexanedinitrile

1-amino-5-cyanopentane
2432-74-8

1-amino-5-cyanopentane

Conditions
Conditions Yield
With ammonia; hydrogen; Raney nickel; In tetrahydrofuran; water; at 110 ℃; for 3h; under 18100.7 Torr; Product distribution / selectivity; Parr reactor;
32.8 %Chromat.
26.3 %Chromat.
With ammonia; hydrogen; Raney nickel; In tetrahydrofuran; water; at 80 ℃; for 3h; under 54302 Torr; Product distribution / selectivity; Parr reactor;
18.4 %Chromat.
75.2 %Chromat.

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  • Amadis Chemical Co., Ltd.
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  • Emails:sales@amadischem.com
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  • Hangzhou Keyingchem Co.,Ltd
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  • Shanghai AngewChem Co., Ltd.
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