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Home > Encyclopedia > 2,6-Lutidine

2,6-Lutidine

2,6-Lutidine structure

2,6-Lutidine 

structure

Description

Colorless oily liquid, melting point-5.8℃, boiling point 144℃(139-141℃,145.6-145.8℃), density 0.9252(20/4℃), refractive index 1.4977, flash point 33℃, soluble in dimethyl formamide, tetrahydrofuran, cold water, hot water, ethanol and ether, with mixed odor of Pyridine and mint. Colorless to yellow liquid 2,6-Dimethylpyridine has a powerful and diffusive minty-tarry odor. It has also been described to have the odor of pyridine and peppermintChEBI: A member of the class of methylpyridines that


Lutidine appears as a colorless liquid with a peppermint odor. Less dense than water. Vapors heavier than air. Produces toxic oxides of nitrogen during combustion. Used to make other chemicals.|Liquid|Colourless oily liquid; Diffusive minty aroma, nutty, coffee-like


Lutidine appears as a colorless liquid with a peppermint odor. Less dense than water. Vapors heavier than air. Produces toxic oxides of nitrogen during combustion. Used to make other chemicals.|2,6-dimethylpyridine is a member of the class of methylpyridines that is pyridine carrying methyl substituents at positions 2 and 6. It derives from a hydride of a pyridine.

2,6-Lutidine Basic Attributes

107.15

107.15

105690

203-587-3

15FQ5D0T3P

2155

2734

DTXSID7051557

Oily liq

29333999

Characteristics

12.9

1.68

Clear Liquid

0.9252 g/cm3 @ Temp: 20 °C

-5.8 °C

144 °C @ Press: 760 Torr

92 °F

n 20/D 1.497(lit.)

H2O: 40 g/100 mL (20 ºC)

−20°C

5.5 hPa (20 °C)

3.70 (Air= 1)

Oral-Rat LD50: 400 mg/kg

It is flammable in case of open flame, high temperature and oxidant; it produces toxic nitrogen oxide gas in case of heat

Odor of pyridine plus peppermint

1.04e-05 atm-m3/mole|Henry's Law constant = 1.04X10-5 atm-cu m/mol @ 25 °C

pKa = 6.60 (conjugate acid)

Highly flammable. Soluble in water.

Amines, Phosphines, and Pyridines

Highly Flammable

LUTIDENE 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

III

3

UN 1993 3/PG 3

3

10-22-36/37/38-20/21/22

26-36/37-16-36-36/37/39

OK9700000

Xn,F,Xi

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

Irritant/Flammable

Stable. Flammable. Incompatible with strong oxidizing agents, acid chlorides, acids, chloroformates. Protect from moisture.

P261-P305 + P351 + P338

H226-H302-H315-H319-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.

REVIEW OF 2,6-DIMETHYLPYRIDINE; HAZARDS, USES & RECOMMENDATIONS FOR STORAGE & HANDLING & MEDICAL TREATMENT IN CASE OF ACCIDENTS.[MOREL C ET AL; CAH NOTES DOC 99: 319 (1980)]

Excerpt from ERG Guide 132 [Flammable Liquids - Corrosive]: Flammable/combustible material. May be ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. (ERG, 2016)

|Warning|H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P312, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, and P501|Aggregated GHS information provided by 426 companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H226: Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P264, P270, P280, P301+P312, P303+P361+P353, P330, P370+P378, P403+P235, and P501

Excerpt from ERG Guide 132 [Flammable Liquids - Corrosive]: Some of these materials may react violently with water. SMALL FIRE: Dry chemical, CO2, water spray or alcohol-resistant foam. LARGE FIRE: Water spray, fog or alcohol-resistant foam. Move containers from fire area if you can do it without risk. Dike fire-control water for later disposal; do not scatter the material. Do not get water inside containers. FIRE INVOLVING TANKS OR CAR/TRAILER LOADS: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. For massive fire, use unmanned hose holders or monitor nozzles; if this is impossible, withdraw from area and let fire burn. (ERG, 2016)

Excerpt from ERG Guide 132 [Flammable Liquids - Corrosive]: As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. 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 132 [Flammable Liquids - Corrosive]: Fully encapsulating, vapor-protective clothing should be worn for spills and leaks with no fire. ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). All equipment used when handling the product must be grounded. Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. A vapor-suppressing foam may be used to reduce vapors. Absorb with earth, sand or other non-combustible material and transfer to containers (except for Hydrazine). Use clean, non-sparking tools to collect absorbed material. LARGE SPILL: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor, but may not prevent ignition in closed spaces. (ERG, 2016)

Excerpt from ERG Guide 132 [Flammable Liquids - Corrosive]: 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)

2,6-Lutidine was detected in oil shale retort water in Australia at a concn of 3 mg/l(1). Effluent from a municipal treatment plant in Hamilton, Ontario released 2,6-lutidine at a rate of 0.42 kg/day(2). Unspecified isomers of lutidine were detected in feedwater and permeate water from an abandoned creosote manufacturing plant in Pensacola, FL at concns of 2.48 and 0.032 mg/l, respectively(3).

2,6-Lutidine was identified, not quantified, in soil from Moscow, Russia(1).

Toxicity

highly toxic

LD50 Rat oral 400 mg/kg|LD50 Guinea pig skin 2500 mg/kg

2,6-Lutidine's production and use as a chemical intermediate in the production of pharmaceuticals, resins, dyestuffs, rubber accelerators and insecticides(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 200(SRC), determined from a measured log Kow of 1.68(2) and a regression-derived equation(3), indicates that 2,6-lutidine is expected to have moderate mobility in soil(SRC). The pKa of 2,6-lutidine is 6.6(4), which indicates that 2,6-lutidine will partially exist in the protonated form in moist soils and cations adsorb to soil surfaces more strongly than neutral compounds(SRC). Volatilization of the neutral species of 2,6-lutidine from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 1.04X10-5 atm-cu m/mole(5), but the protonated form will not volatilize. The potential for volatilization of 2,6-lutidine from dry soil surfaces may exist based upon a vapor pressure of 5.65 mm Hg(6). 2,6-Lutidine biodegrades in soils under aerobic conditions(7). The half-life of 2,6-lutidine was approximately 1 month in an unpolluted surface soil under aerobic conditions with 100% degradation observed after 3 months(7) in a second, 2,6-lutadine was completely degraded in 32 days(8). Little degradation was observed under denitrifying and sulfate-reducing conditions(7).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 200(SRC), determined from a measured log Kow of 1.68 (2) and a regression-derived equation(3), indicates that 2,6-lutidine is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 1.04X10-5 atm-cu m/mole(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 2 and 31 days, respectively(SRC). The pKa of 2,6-lutidine is 6.6(5), which indicates that 2,6-lutidine will partially exist in the protonated form in water and cations will not volatilize(SRC). According to a classification scheme(6), an estimated BCF of 4(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). 2,6-Lutidine was shown to biodegrade under aerobic conditions in soil (especially polluted soil), but the rate of degradation was slower under anaerobic conditions(8); similar biodegradation in water is expected. 2,6-Lutidine was degraded approximately 30% over the course of a 35 day incubation period in column experiments using contaminated groundwater from a coal tar producing chemical facility as inoculum(9).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,6-lutidine, which has a vapor pressure of 5.65 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2,6-lutidine 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 6 days(SRC), calculated from its rate constant of 2.8X10-12 cu cm/molecule-sec at 25 °C (SRC) determined using a structure estimation method(3).

The rate constant for the vapor-phase reaction of 2,6-lutidine with photochemically-produced hydroxyl radicals has been estimated as 2.8X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 6 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The pKa of 2,6-lutidine is 6.6(2), which indicates that 2,6-lutidine will partially exist in the protonated form in the environment(SRC). Analogous 3,5-lutidine has a weak absorption band that extends into the environmental UV spectrum(3), which suggests that direct photolysis is not likely to occur for alkylated pyridines(SRC).

An estimated BCF of 4 was calculated for 2,6-lutidine(SRC), using a log Kow of 1.68(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

The Koc of 2,6-lutidine is estimated as 200(SRC), using a measured log Kow of 1.68(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 2,6-lutidine is expected to have moderate mobility in soil. The pKa of 2,6-lutidine is 6.6(4), which indicates that 2,6-lutidine will partially exist in the protonated form in moist soils and cations adsorb to soil surfaces more strongly than neutral compounds(SRC).

The Henry's Law constant for 2,6-lutidine is 1.04X10-5 atm-cu m/mole(1). This Henry's Law constant indicates that 2,6-lutidine 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 2 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 31 days(SRC). 2,6-Lutidine's Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur(SRC). The pKa of 2,6-lutidine is 6.6(3), which indicates that 2,6-lutidine will partially exist in the protonated form in water and moist soils and cations will not volatilize(SRC). 2,6-Lutidine may volatilize from dry soil surfaces(SRC) based on its vapor pressure of 5.65 mm Hg at 25 °C(4).

Unspecified isomers of lutidine were detected in streamwater and groundwater from an abandoned creosote manufacturing plant in Pensacola, FL at concns of 0.0058 and 0.1 mg/l, respectively(1). 2,6-Lutidine was detected in groundwater near a creosote manufacturing plant in Indianapolis, IN at 1,928 mg/l(2). 2,6-Lutidine was identified, not quantified, in drinking water in the US(3).

2,6-Lutidine was identified, not quantified, in boiled beef(1) and roasted filberts(2).

Occupational exposure to 2,6-lutidine may occur through inhalation and dermal contact with this compound at workplaces where 2,6-lutidine is produced or used. Monitoring data indicate that the general population may be exposed to 2,6-lutidine via ingestion of food and drinking water. Since this compound is a constituent of coal tar and coal tar creosote, the general population may be exposed to 2,6-lutidine from consumer products which contain coal tar or coal tar creosote. (SRC)

Drug Information

Excerpt from ERG Guide 132 [Flammable Liquids - Corrosive]: May cause toxic effects if inhaled or ingested/swallowed. Contact with substance may cause severe burns to skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution. (ERG, 2016)

Excerpt from ERG Guide 132 [Flammable Liquids - Corrosive]: 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. In case of burns, immediately cool affected skin for as long as possible with cold water. Do not remove clothing if adhering to skin. Keep victim calm and warm. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. (ERG, 2016)

/SRP:/ 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 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 patent can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Aniline and related compounds/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen. ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Aniline and related compounds/

2,6-lutidine

2,6-Lutidine Use and Manufacturing

Methods of Manufacturing

It can be isolated by recovering β-picoline fraction from coal coking by-products.

Uses

Isolated from the basic fraction of coal tar. A semi-volatile compound in tobacco.

Production

(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS|(1986) No Data

99% Grade, 98% min. purity grade

Pyridine, 2,6-dimethyl-: ACTIVE

COULSON EA & HALES JL; ANALYST 78: 114 (1953). ...PYRIDINE DERIVATIVES...CAN EASILY BE MEASURED BY ULTRAVIOLET ABSORPTION METHODS. INFRARED SPECTROSCOPY HAS BEEN USED FOR DETERMINATION OF...METHYL PYRIDINES. /PYRIDINE DERIVATIVES/

Food additives -> Flavoring Agents|Flavoring Agents -> JECFA Flavorings Index

Flavoring Agents

Computed Properties

Molecular Weight:107.15
XLogP3:1.7
Hydrogen Bond Acceptor Count:1
Exact Mass:107.073499291
Monoisotopic Mass:107.073499291
Topological Polar Surface Area:12.9
Heavy Atom Count:8
Complexity:62.8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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