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Dodecylamine

Dodecylamine structure

Dodecylamine 

structure
  • CAS No:

    124-22-1

  • Formula:

    C12H27N

  • Chemical Name:

    Dodecylamine

  • Synonyms:

    1-Dodecanamine;Dodecylamine;Laurylamine;Alamine 4;Armeen 12D;1-Aminododecane;n-Dodecylamine;Laurinamine;1-Dodecylamine;Nissan Amine BB;n-Laurylamine;Amine BB;Kemamine P 690;Monododecylamine;Farmin 20D;Lauramine;Monolaurylamine;HAN 12;Lipomin 12D;Adogen 163D;126162-08-1;27177-40-8

  • Categories:

    Cosmetic Ingredient  >  Antistatic

Description

WHITE CRYSTALLINE POWDER WITH CHARACTERISTIC ODOUR.


Dodecanamine appears as a yellow liquid with an ammonia-like odor. Insoluble in water and less dense than water. Hence floats on water. Contact may irritate skin, eyes and mucous membranes. May be toxic by ingestion, inhalation or skin absorption. Used to make other chemicals.|Liquid; OtherSolid|WHITE CRYSTALLINE POWDER WITH CHARACTERISTIC ODOUR.


Dodecanamine appears as a yellow liquid with an ammonia-like odor. Insoluble in water and less dense than water. Hence floats on water. Contact may irritate skin, eyes and mucous membranes. May be toxic by ingestion, inhalation or skin absorption. Used to make other chemicals.

Dodecylamine Basic Attributes

185.350

185.35

268-953-7

YWY9OD6A2K

1364

2735

DTXSID3021984

OIL

2921199090

Characteristics

26.02000

5.18

Dodecanamine appears as a yellow liquid with an ammonia-like odor. Insoluble in water and less dense than water. Hence floats on water. Contact may irritate skin, eyes and mucous membranes. May be toxic by ingestion, inhalation or skin absorption. Used to make other chemicals.

0.8015 g/cm3 @ Temp: 20 °C

28.3 °C

259 °C

100.4±13.1 °C

1.444

Solubility in water: poor

Store in a cool, dry place. Store in a tightly closed container. Corrosives area.

8.05X10-3 mm Hg at 25 deg C

AMINE ODOR

Insoluble in water.

Amines, Phosphines, and Pyridines

DODECANAMINE neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Safety Information

II

8

UN 3259 8/PG 3

2

R20/21/22;R34

S26-S36/37/39-S45-S60-S61

JR6475000

C:Corrosive;

Separated from acids, acid anhydrides, acid chlorides and oxidants. Store in an area without drain or sewer access. Provision to contain effluent from fire extinguishing.

Stable. Combustible. Incompatible with acid chlorides, acids, acid anhydrides, oxidizing agents.

P261-P273-P280-P301 + P310-P305 + P351 + P338-P310

H304-H314-H335-H373-H410

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.

... Can react with oxidizing materials.

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. Gives off irritating or toxic fumes (or gases) in a fire.

|Danger|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P260, P261, P264, P270, P271, P273, P280, P301+P310, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P314, P321, P330, P331, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 46 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H290 (62.66%): May be corrosive to metals [Warning Corrosive to Metals]|P234, P260, P261, P264, P270, P271, P273, P280, P301+P310, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P314, P321, P330, P331, P363, P390, P391, P403+P233, P404, P405, and P501|Aggregated GHS information provided by 747 companies from 23 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P260, P261, P264, P270, P271, P280, P301+P310, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P314, P321, P330, P331, P363, P403+P233, 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)

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)

Combustible when exposed to heat or flame ...

To fight fire, use foam, carbon dioxide, dry chemical.

Personal protection: chemical protection suit including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Sweep spilled substance into covered sealable containers. Carefully collect remainder. Then store and dispose of according to local regulations.

Separated from acids, acid anhydrides, acid chlorides and oxidants. Store in an area without drain or sewer access. Provision to contain effluent from fire extinguishing.

No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation 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.

NO open flames.

AVOID ALL CONTACT! IN ALL CASES CONSULT A DOCTOR!

Use local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear face shield or eye protection in combination with breathing protection.

Toxicity

LD50 Mouse ip 320 mg/kg

Dodecylamine's production and use as a cationic surface-active agent(1) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 9,300(SRC) determined from an estimated log Kow of 4.8(2,SRC) and a regression-derived equation(3) indicates that dodecylamine is expected to be immobile in soil(SRC). A pKa of 10.63(4) indicates dodecylamine will exist predominately in the protonated form at environmental pHs and as a result, volatilization from moist soil surfaces is not expected to be an important fate process(SRC). Dodecylamine is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 8.05X10-3 mm Hg(5). A 60% of theoretical BOD in an activated sludge inoculum over a 12 day incubation period suggests that dodecylamine may biodegrade in soil(6).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 9,300(SRC) determined from an estimated log Kow of 4.8(2,SRC) and a regression-derived equation(3) indicates that dodecylamine is expected to adsorb to suspended solids and sediment in the water column(SRC). A pKa of 10.63(4) indicates that volatilization from water surfaces is not expected to be an important fate process since this compound will exist predominately in the protonated form at environmental pHs(SRC). According to a classification scheme(5), an estimated BCF of 2,400(3,SRC), from an estimated log Kow(2,SRC), suggests the potential for bioconcentration in aquatic organisms is very high(SRC). A 60% of theoretical BOD in an activated sludge inoculum over a 12 day incubation period, suggests that dodecylamine may biodegrade in water(6).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dodecylamine, which has a vapor pressure of 8.05X10-3 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase dodecylamine 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 8.4 hours(SRC) from its rate constant of 4.6X10-11 cu cm/molecule-sec estimated using a structure estimation method(3).

The rate constant for the vapor-phase reaction of dodecylamine with photochemically-produced hydroxyl radicals has been estimated as 4.6X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 8.4 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1).

An estimated BCF of 2,400 was calculated for dodecylamine(SRC), using an estimated log Kow of 4.8(1,SRC) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is very high.

The Koc of dodecylamine is estimated as 9,300(SRC), using an estimated log Kow of 4.8(1,SRC) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that dodecylamine is expected to be immobile in soil. An H-Type isotherm was observed for the sorption of dodecylamine to sodium montmorillonite in aqueous solution; this type of isotherm indicates that the solute is preferentially sorbed to such an extent that no measurable amount remains in solution(4).

The Henry's Law constant for dodecylamine is estimated as 2.7X10-4 atm-cu m/mole(SRC), using a fragment constant estimation method(1). This Henry's Law constant indicates that the neutral form of dodecylamine is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as approximately 14 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 110 days(SRC). A pKa of 10.63(3) indicates dodecylamine will exist predominately in the protonated form at environmental pHs and therefore volatilization from water and moist soil surfaces is not expected to be an important fate process(SRC). Dodecylamine is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 8.05X10-3 mm Hg(4).

Dodecylamine was detected in the following samples of mixed pickles, mg/kg: cucumber in aromatic vinegar, 2.7; cucumber in aromatic vinegar brine, 1.9 mg/l; pepperoni, 6.4; pepperoni brine, 0.7 mg/l; pickled onions, 3.6; pickled onions brine, 0.1 mg/l(1).

...HIGHER BOILING POINTS SHOULD DECR HAZARD FROM VAPOR EXPOSURES. /HIGHER ALKYLAMINES/|NIOSH (NOES Survey 1981-1983) has statistically estimated that 2,136 workers (306 of these are female) are potentially exposed to dodecylamine in the US(1). Occupational exposure to dodecylamine may occur through inhalation and dermal contact with this compound at workplaces where dodecylamine is produced or used(SRC).

Drug Information

Agents that modify interfacial tension of water; usually substances that have one lipophilic and one hydrophilic group in the molecule; includes soaps, detergents, emulsifiers, dispersing and wetting agents, and several groups of antiseptics. (See all compounds classified as Surface-Active Agents.)

AMINES ARE WELL ABSORBED FROM GUT & RESPIRATORY TRACT. /AMINES/

MONOAMINE...& DIAMINE OXIDASE...OCCUR WIDELY...MOST CONCN IN LIVER, KIDNEY, & INTESTINAL MUCOSA. ...ASSUMED THAT THEY PLAY AN IMPORTANT ROLE IN "DETOXICATION" OF AMINES...AMMONIA FORMED IS CONVERTED TO UREA. HYDROGEN PEROXIDE IS ACTED ON BY CATALASE...ALDEHYDE FORMED /GIVES A/...CARBOXYLIC ACID. /AMINES/

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)

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.


Remove contaminated clothes. 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.

EARLY TREATMENT /CORROSIVE BURNS OF ESOPHAGUS/ CONSISTS OF IV FLUID THERAPY, BROAD SPECTRUM ANTIBIOTICS, SEDATION, PARENTERAL HYDROCORTISONE & MORE IMPORTANTLY MAINTAINING PATENCY OF THE ESOPHAGUS FOLLOWED BY DILATATION. /ALKALIES/|THE READY AVAILABILITY OF MILK OR WATER, ACCEPTANCE BY CHILD & LACK OF TOXIC SIDE EFFECTS MAKE THEM DILUENTS OF CHOICE FOR ALKALINE CORROSIVE AGENTS.

dodecylamine

The substance can be absorbed into the body by ingestion.

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


Redness. Pain. Skin burns.


Redness. Pain. Severe deep burns.

Dodecylamine Use and Manufacturing

Methods of Manufacturing

REACTION OF DODECANOIC ACID WITH AMMONIA TO FORM LAURONITRILE, FOLLOWED BY CATALYTIC HYDROGENATION TO FORM DODECYLAMINE|Lauric acid, broad cut/lauric acid, narrow cut + ammonia (nitrile formation/hydrogenation).

Uses

Intermediates

Production

500,000 - 1,000,000 lb|(1971) 3.1X10+8 GRAMS|(1975) GREATER THAN 1.36X10+6 GRAMS (EST)

PRIMARILY AS A CHEMICAL INTERMEDIATE FOR THE FUNGICIDE, DODECYLGUANIDINE ACETATE (1976)

All other basic organic chemical manufacturing|1-Dodecanamine: ACTIVE|Amines, C12-18-alkyl: ACTIVE|WASTEWATER CONTAINING 1 G UO2/L WAS TREATED WITH DODECYLAMINE ACETATE (50 MG) & 20 MG TAKASA FROTH. UO2 RECOVERY IN FROTH WAS 98%.|EVALUATED FOR INHIBITORY ACTIVITY AGAINST S MUTANS 6715, DODECYLAMINE SHOWED GOOD ACTIVITY. FURTHER IN VITRO STUDIES AGAINST OTHER PLAQUE-FORMING BACTERIA ARE NEEDED TO DETERMINE BEST CLINICAL AGENT.

Cosmetics -> Antistatic

Computed Properties

Molecular Weight:185.35
XLogP3:5.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:10
Exact Mass:185.214349865
Monoisotopic Mass:185.214349865
Topological Polar Surface Area:26
Heavy Atom Count:13
Complexity:81.2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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