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Home > Encyclopedia > Hexamethylenediamine

Hexamethylenediamine

Hexamethylenediamine structure

Hexamethylenediamine 

structure
  • CAS No:

    124-09-4

  • Formula:

    C6H16N2

  • Chemical Name:

    Hexamethylenediamine

  • Synonyms:

    1,6-Hexanediamine;1,6-Diaminohexane;Hexamethylenediamine;HMDA;1,6-Hexylenediamine;1,6-Diamino-n-hexane;Hexylenediamine;α,ω-Hexanediamine;V 1;Hi Perm;NSC 9257;80HMD;Advancure;RT Advancure HD;Dytek 70;6-Aminohexylamine;Dytek HMD

  • Categories:

    Cosmetic Ingredient  >  Buffering

Description

Colorless crystalline solid or clear liquid.


Hexamethylenediamine is the organic compound with the formula H2N(CH2)6NH2. The molecule is a diamine, consisting of a hexamethylene hydrocarbon chain terminated with amine functional groups. The colorless solid (yellowish for some commercial samples) has a strong amine odor, similar to piperidine. About 1 billion kilograms are produced annually.


Hexamethylenediamine, solid is a colorless crystalline solid. It is soluble in water. It is corrosive to metals and tissue. Produces toxic oxides of nitrogen during combustion.|Hexamethylenediamine, solution appears as a clear colorless liquid. Burns although some effort is required to ignite. Soluble in water. Corrosive to metals and tissue. Produces toxic oxides of nitrogen during combustion. Used to make nylon.|Liquid; WetSolid, Liquid|HYGROSCOPIC PELLETS OR FLAKES WITH CHARACTERISTIC ODOUR.|Colorless crystalline solid or clear liquid.


Hexamethylenediamine, solid is a colorless crystalline solid. It is soluble in water. It is corrosive to metals and tissue. Produces toxic oxides of nitrogen during combustion.|Hexamethylenediamine, solution appears as a clear colorless liquid. Burns although some effort is required to ignite. Soluble in water. Corrosive to metals and tissue. Produces toxic oxides of nitrogen during combustion. Used to make nylon.|Hexane-1,6-diamine is a C6 alkane-alpha,omega-diamine. It has a role as a human xenobiotic metabolite. It derives from a hydride of a hexane.

Hexamethylenediamine Basic Attributes

116.2

116.20

1098307

204-679-6

ZRA5J5B2QW

0659

9257

2280|1783

DTXSID5024922

COLORLESS LEAFLETS|RHOMBIC BIPYRAMIDAL PLATES

2921229000

Characteristics

52

1.86480

White, may discolor during storage Solution

0.93 g/cm3

42 °C

205 °C

201 °F

n20/D 1.439(lit.)

H2O: 490 g/L (20 ºC);alcohol: soluble (lit.)

2-8°C

Vapour pressure, Pa at 50°C: 200

4 (vs air)

Oral-rat LD50: 750 mg/kg; inhalation-mouse LCL0: 750 mg/m3/10min

Combustible; burning emits toxic nitrogen oxide fumes

0.9-7.6%(V)

ODOR OF PIPERIDINE

pKb= 3.3, pKa= 10.7|pKa = 11.02 (conjugate acid)

SUBLIMES AS LONG NEEDLES|CONVERSION FACTOR: 1 MG/L= 210 PPM; 1 PPM= 4.75 MG/CU M|NEEDLES FROM WATER OR ALCOHOL; FREELY SOL IN WATER; MP: 248 °C /HEXAMETHYLENE DIAMINE DIHYDROCHLORIDE/|HEAT OF SOLUTION (EST): -9 BTU/LB= -5 CAL/G= -0.2X10+5 J/KG

May be sensitive to air. Water soluble.|Water soluble.

Amines, Phosphines, and Pyridines

HEXAMETHYLENEDIAMINE is hygroscopic. This compound can react with strong oxidizing materials. It is incompatible with acids, acid chlorides and acid anhydrides. It is also incompatible with ketones, aldehydes, nitrates, phenols, isocyanates, monomers and chlorinated compounds. (NTP, 1992).|HEXAMETHYLENEDIAMINE is hygroscopic. Can react with strong oxidizing materials. Incompatible with acids, acid chlorides and acid anhydrides. Also incompatible with ketones, aldehydes, nitrates, phenols, isocyanates, monomers and chlorinated compounds (NTP, 1992).

734 to 788 °F (NTP, 1992)|305 °C

(est) -12,200 Btu/lb= -6,790 cal/g= -284X10+5 J/kg

0.7-6.3% in air

203 BTU/LB= 113 CAL/G= 4.73X10+4 J/KG

Safety Information

III

8

UN 2735 8/PG 3

3

34-37-21/22-20/21/22

26-36/37/39-45-22-27

MO1180000

C

The warehouse is ventilated, low-temperature and dry; stored separately from acids and oxidants.

Stable. Combustible. Incompatible with strong oxidizing agents, strong acids, organic materials.

P301 + P312 + P330-P303 + P361 + P353-P304 + P340 + P310-P305 + P351 + P338

H302 + H312-H314-H335

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.|FEASIBILITY OF MICROBIAL DECOMP OF ORGANIC WASTES UNDER CONDITIONS EXISTING IN DEEP WELLS WAS INVESTIGATED. UNDER AEROBIC CONDITIONS TEMP IS NOT A CONSTRAINT; THERMOPHILIC BACTERIA DECOMP A WIDE VARIETY OF COMPOUNDS. GROWTH OF THERMOPHILIC BACTERIA IS POSSIBLE WITH HEXAMETHYLENEDIAMINE.|(1) Add to layer of sodium bisulfite. Spray with water and neutralize. ...

...can react with oxidizing materials.

DHHS/NTP; NTP Technical Report on Toxicity Studies of 1,6-Hexanediamine Dihydrochloride Administered by Drinking Water and Inhalation to F344/N Rats and B6C3F1 Mice. Toxicity Rpt Series No. 24 NIH Publication No. 93-3347 (1993)

UN 1783

P301 + P312 + P330; P303 + P361 + P353; P304 + P340 + P310; P305 + P351 + P338

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)|Combustible.|Corrosives, Flammable - 2nd degree

|Danger|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P260, P261, P264, P270, P271, P280, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P363, P403+P233, P405, and P501|H302+H312 (37.31%): Harmful if swallowed or in contact with skin [Warning Acute toxicity, oral; acute toxicity, dermal]|Aggregated GHS information provided by 1281 companies from 29 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P201, P202, P260, P261, P264, P270, P272, P280, P281, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P307+P311, P308+P313, P309+P311, P310, P312, P314, P321, P322, P330, P333+P313, P363, P405, and P501|P201, P202, P260, P261, P264, P270, P272, P280, P281, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P309+P311, P310, P312, P314, P321, P322, P330, P333+P313, P363, P405, and P501

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2016)

Protective clothing; eye protection. (USCG, 1999)|Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. (ERG, 2016)|Protective clothing; eye protection.|Personnel protection: ... Wear appropriate protective gloves, boots and goggles. ... Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Hexamethylene diamine solution; hexamethylene diamine, solid/

COMBUSTIBLE WHEN EXPOSED TO HEAT OR FLAME...

Explosive limits , vol% in air: 0.9-7.6

Extinguish with water, foam, dry chemical, or carbon dioxide.|If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Solid streams of water may be ineffective. Use "alcohol" foam, dry chemical or carbon dioxide. /Hexamethylene diamine solution/|If material on fire or involved in fire: Use water in flooding quantities as fog. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Solid streams of water may be ineffective. Use "alcohol" foam, dry chemical or carbon dioxide. /Hexamethylene diamine, solid/

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.

If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. /Hexamethylene diamine solution/|If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. /Hexamethylene diamine, solid/|Personnel protection: Avoid breathing vapors. Keep upwind. Avoid bodily contact with the material. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. ... If contact with the material anticipated, wear appropriate chemical protective clothing. /Hexamethylene diamine solution; hexamethylene diamine, solid/

/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Health: 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. /Hexamethylenediamine, solid; Hexamethylenediamine, solution/|/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Fire or Explosion: 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. /Hexamethylenediamine, solid; Hexamethylenediamine, solution/|/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas. /Hexamethylenediamine, solid; Hexamethylenediamine, solution/|/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. /Hexamethylenediamine, solid; Hexamethylenediamine, solution/|For more DOT Emergency Guidelines (Complete) data for HEXAMETHYLENE DIAMINE (8 total), please visit the HSDB record page.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

DIAMINES ARE STRONG BASES & EXHIBIT SKIN & EYE IRRITANT PROPERTIES SIMILAR TO MONOAMINES. /DIAMINES/|THE SOLID MAY BE EXPECTED TO BE STRONGLY IRRITATING OR CAUSTIC TO THE EYES ON ACCOUNT OF ITS ALKALINITY.

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.

Separated from strong oxidants and strong acids. Well closed.

A harmful contamination of the air can be reached rather quickly on evaporation of this substance at 20 °C.

The substance is corrosive to the eyes, skin and respiratory tract. Corrosive on ingestion. Inhalation may cause lung oedema. The effects may be delayed. Medical observation is indicated.

Repeated or prolonged contact with skin may cause dermatitis.

NO open flames. NO contact with hot surfaces.

STRICT HYGIENE!

Use ventilation (not if powder), local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear safety spectacles, face shield or eye protection in combination with breathing protection.

Toxicity

moderately toxic

Hexamethylene diamine's production and use as a chemical intermediate in the production of nylon-type polyimide resins(1) may result in its release to the environment through a variety of waste streams(SRC).

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 286(SRC), determined from a structure estimation method(2), indicates that hexamethylene diamine is expected to have moderate mobility in soil(SRC). Volatilization of hexamethylene diamine is not expected from moist soil surfaces(SRC) given an estimated Henry's Law constant of 3.2X10-9 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Volatilization of hexamethylene diamine from dry soil surfaces is not expected(SRC) based on an extrapolated vapor pressure of 0.12 mm Hg(SRC) at 25 °C(4). Biodegradation is expected to be an important environmental fate process for this compound(SRC). Standard BOD dilution techniques with activated sludge indicate that hexamethylene diamine biodegrades under aerobic conditions(5-7).|AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 286(SRC), determined from a structure estimation method(2), indicates that hexamethylene diamine is expected to adsorb to suspended solids and sediment in water(SRC). Hexamethylene diamine is not expected to volatilize from water surfaces(3,SRC) based on an estimated Henry's Law constant of 3.2X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). An experimental pKa value of 11(5), indicates that hexamethylene diamine will not dissociate significantly at environmentally important pH values(SRC). Biodegradation is expected to occur slowly in aqueous environments(SRC). Degradation rates of 4% and 10% were observed for hexamethylene diamine (50 ppm) incubated in water from the Mino River, Japan and seawater off the coast of Japan over a 3 day incubation period(6). According to a classification scheme(7), an estimated BCF value of 1(3,SRC), from an estimated log Kow of 0.35(8,SRC), suggests that bioconcentration in aquatic organisms is low(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), hexamethylene diamine, which has an extrapolated vapor pressure of 0.12 mm Hg at 25 °C(2,SRC), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase hexamethylene diamine is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be about 6 hours(3,SRC).

The rate constant for the vapor-phase reaction of hexamethylene diamine with photochemically-produced hydroxyl radicals has been estimated as 6.9X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 6 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC). An experimental pKa value of 11(2), indicates that hexamethylene diamine will not dissociate significantly at environmentally important pH values(SRC). Hexamethylene diamine is not expected to undergo hydrolysis or direct photolysis in the environment due to the lack of functional groups to hydrolyze or absorb UV radiation at environmentally significant wavelengths(SRC).

An estimated BCF value of 1 was calculated for hexamethylene diamine(SRC), using an estimated log Kow of 0.35(1,SRC) and a recommended regression-derived equation(2). According to a classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms is low(SRC).

Based on a recommended classification scheme(1), an estimated Koc value of 286(SRC), determined from a structure estimation method(2), indicates that hexamethylene diamine is expected to have moderate mobility in soil(SRC).

The Henry's Law constant for hexamethylene diamine is estimated as 3.2X10-9 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that hexamethylene diamine will be essentially nonvolatile from water surfaces(2,SRC). Hexamethylene diamine is not expected to volatilize from dry soil surfaces based on an extrapolated vapor pressure of 0.12 mm Hg at 25 °C(3).

CONJUNCTIVAL & UPPER RESPIRATORY TRACT IRRITATION HAVE BEEN OBSERVED IN WORKERS HANDLING HEXAMETHYLENEDIAMINE. ... AIR CONCN VARIED FROM 2 & 5.5 MG/CU M DURING NORMAL OPERATIONS TO 32.7 AND 131.5 MG/CU M DURING AUTOCLAVE OPERATIONS IN 2 PLANTS.|.../1 REPORT INDICATES/ THAT HEXAMETHYLENEDIAMINE MAY HAVE BEEN THE CAUSE OF HEMOLYTIC ANEMIA PREVIOUSLY REPORTED IN NYLON WORKERS EXPOSED TO CRUDE ADIPONITRILE. HOWEVER THIS WAS NOT FOUND...IN A /LATER/ STUDY OF WORKERS EXPOSED TO HEXAMETHYLENEDIAMINE.|NIOSH (NOES Survey 1981-1983) has statistically estimated that 11,005 workers (1,701 of these are female) are potentially exposed to hexamethylene diamine in the US(1). Occupational exposure may be through inhalation and dermal contact with this compound at workplaces where hexamethylene diamine is produced or used(2,SRC).

Drug Information

.../HEXAMETHYLENE IS/ ABSORBED THROUGH THE SKIN.|Following oral administration of (14)C-labeled 1,6-diaminohexane to male rats, approx 20% of the administered dose was recovered as (14)CO2 after 72 hr. Urinary and fecal excretion accounted for 47 and 27% of the administered radioactivity, respectively. Of several tissues examined, the highest concn of residual radioactivity were found in the prostate at 24 and 72 hr post-administration.|An isocyanate generation apparatus was developed and stable isocyanate atmospheres were obtained. At a concn of 5 ug 1,6-hexamethylene diisocyanate (HD) per cu m the precision was found to be 7% (n = 5). Three volunteers were each exposed to the different concn of HI (11.9, 20.5, and 22.1 micrograms/ cu m) and three concns of isophorone diisocyanate (IPDI) (12.1, 17.7, and 50.7 micrograms/cu m), in an exposure chamber. The duration of the exposure was 2 hr. Urine and blood samples were collected, and hydrolyzed under alkaline conditions to the HI and IPDI corresponding amines, 1,6-hexamethylene diamine (HDA) and isophorone diamine (IPDA), determined as their pentafluoropropionic anhydride amides (HDA-PFPA and IPDA-PFPA). The HDA- and IPDA-PFPA derivatives were analyzed using liquid chromatography mass spectrometry with thermospray monitoring negative ions. When working up samples from the exposed persons without hydrolysis, no HDA or IPDA was seen. The average urinary excretion of the corresponding amine was 39% for HI and 27% for IPDI . An association between the estimated inhaled dose and the total excreted amount was seen. The average urinary elimination half-time for HDA was 2.5 hr and for IPDA, 2.8 hr. The hydrolysis condition giving the highest yield of HDA and IPDA in urine was found to be hydrolysis wi the 3 M sodium hydroxide during 4 hr. No HDA or IPDA could be found in hydrolyzed plasma (< ca 0.1 micrograms/l) .

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)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. Corrosive chemicals will destroy the membranes of the mouth, throat, and esophagus and, in addition, have a high risk of being aspirated into the victim's lungs during vomiting which increases the medical problems. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. IMMEDIATELY transport the victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. Transport the victim IMMEDIATELY to a hospital. (NTP, 1992)|Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin. Keep victim calm and warm. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. (ERG, 2016)


Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer for medical attention.


Rinse skin with plenty of water or shower. Refer for medical attention .


First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

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/|For basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... Monitor for shock and treat if necessary ... Anticipate seizures and treat if necessary ... For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... Cover skin burns with sterile dressings after decontamination ... . /Organic bases\amines and related compounds/

CONJUNCTIVAL & UPPER RESPIRATORY TRACT IRRITATION HAS BEEN OBSERVED IN WORKERS HANDLING HEXAMETHYLENEDIAMINE. ONE WORKER, OUT OF 20 STUDIED, DEVELOPED ACUTE HEPATITIS FOLLOWED BY DERMATITIS WHICH WAS ATTRIBUTED TO HEXAMETHYLENEDIAMINE. NO ANEMIA WAS OBSERVED.|...CASE...DESCRIBED IN ITALY IN WHICH 20 WORKERS WERE EXPOSED TO HEXAMETHYLENE DIAMINE & 8 SUFFERED FROM IRRITATION TO EYES & UPPER RESPIRATORY TRACT, WHILE ONE CONTRACTED DERMATITIS, & ANOTHER, ACUTE LIVER DISEASE. DERMATITIS HAS...BEEN DESCRIBED IN FRANCE...|Workers involved in the production of condensers were examined. Their contact with hexamethylenediamine, capon lacquer, and epoxide tar results in development of allergic diseases, such as atopic forms of bronchial asthma, allergic rhinitis and dermatitis.

1,6-diaminohexamethylene

The substance can be absorbed into the body by inhalation of its aerosol, through the skin and by ingestion.

Burning sensation. Cough. Laboured breathing. Shortness of breath. Sore throat. Symptoms may be delayed.


MAY BE ABSORBED! Redness. Skin burns. Pain. Blisters.


Redness. Pain. Severe deep burns.

Hexamethylenediamine Use and Manufacturing

Methods of Manufacturing

The production of hexamethylene diamine initially used furfural as a raw material. At present, there are many industrial methods for producing hexamethylene diamine. Depending on the raw materials used, there are adipic acid method, butadiene method, acrylonitrile method, hexanediol method and caprolactam method. Among them, the adipic acid method, butadiene method and acrylonitrile dimerization method are the intermediate adiponitrile hydrogenation to produce hexamethylene diamine. At present, almost all large-scale production methods of hexamethylene diamine are the catalytic hydrogenation of adiponitrile law. 1. Industrially, there are two types of adiponitrile catalytic hydrogenation: high pressure and low pressure. (1) The high-pressure method uses cobalt-copper catalyst, the reaction temperature is 100-135℃, the pressure is 60-65MPa; iron catalyst can also be used, the reaction temperature is 100-180℃, the pressure agent can be liquid ammonia, and sometimes aromatic hydrocarbons (such as toluene) ). The selectivity of hexamethylene diamine is about 90-95%. In production, the gas mixture of liquid hexamethylene, toluene, ammonia, hydrogen-containing ammonia, and a small amount of adiponitrile and toluene is passed into a reactor equipped with a cobalt-copper catalyst. After the crude hexamethylene diamine is exported, first make it Azeotropic distillation with water, and then several vacuum distillations to obtain a high-purity product suitable for manufacturing nylon 66. (2) The low-pressure method uses framework nickel, iron-nickel or chromium-nickel catalysts, and the reaction is carried out in sodium hydroxide solution. The reaction temperature is about 75°C, the pressure is 3MPa, and the selectivity of hexamethylene diamine can reach 99%. In order to prevent catalyst poisoning, the purity of the raw material adiponitrile is very high. 2. The method using adipic acid as the raw material. This method is to pass the adipic acid vapor and excess ammonia through a dehydration catalyst such as silica gel heated to 340°C to generate adiponitrile, and then add methanol and liquid ammonia to it, using silicon Nickel algae is used as a catalyst, and the finished product is obtained by reducing with 10.1325-20.265MPa hydrogen at 90-100°C. 3. The caprolactam method is generally used to treat small production devices such as caprolactam. It is a gas phase reaction of caprolactam and ammonia in the presence of a phosphate (such as manganese, aluminum, calcium, barium or zinc phosphate) catalyst to generate aminoacetonitrile. The reaction temperature is 350°C, and the yield is almost 100%. The resulting aminocapronitrile is then hydrogenated to generate hexamethylene diamine, which is similar to the hydrogenation of adiponitrile.

Uses

Organic synthesis, nylon 66 intermediate.


Drumming/Repackaging

Production

1,000,000,000 - 5,000,000,000 lb|(1972) 3.88X10+11 GRAMS|(1975) 3.40X10+11 GRAMS|Capacity (Jan 1, 1996): Total capacity 1330 million lbs. 930 million lbs (adiponitrile from butadiene); 200 million lbs (adiponitrlie from acrylonitrile); 200 million lbs (transferred adiponitrile).

88% USED IN PRODN OF NYLON 66; 12% USED IN OTHER APPLICATIONS INCLUDING THE PRODN OF NYLON 610 AND 612 (1972)

Grade or purity: Anhydrous: 99.8%; 70% soln

All other basic organic chemical manufacturing|1,6-Hexanediamine: ACTIVE|Amides, vegetable-oil, N,N'-hexanediylbis-: INACTIVE|/NYLON/ MANUFACTURING PROCESS STARTS WITH HIGH-PRESSURE SYNTHESIS OF ADIPIC ACID & HEXAMETHYLENE DIAMINE WHICH ARE HEATED...IN ABSENCE OF AIR TO FORM AMIDE LINKAGES... WATER IS REMOVED & MOLTEN NYLON (...NYLON 66) IS EXTRUDED IN RIBBON-LIKE FORM.../TO BE MELTED & FILAMENTS FORMED/. /POLYAMIDES/

THIN-LAYER CHROMATOGRAPHY WAS USED TO DETERMINE HEXAMETHYLENEDIAMINE IN SANITARY-CHEM STUDIES OF POLYMERS.|Gas chromatographic determination of aliphatic and alicyclic amines as perfluoro fatty acid amides using electron-capture and nitrogen-selective detection is discussed.

Fire Hazards -> Corrosives, Flammable - 2nd degree

Computed Properties

Molecular Weight:116.20
XLogP3:-0.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:5
Exact Mass:116.131348519
Monoisotopic Mass:116.131348519
Topological Polar Surface Area:52
Heavy Atom Count:8
Complexity:31.5
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Downstream Products

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