Pyrrolidine
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Pyrrolidine
structure -
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CAS No:
123-75-1
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Formula:
C4H9N
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Chemical Name:
Pyrrolidine
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Synonyms:
Pyrrolidine;Azacyclopentane;Prolamine;Pyrrole,tetrahydro-;Tetrahydropyrrole;Tetramethylenimine;Pyrrolidine ring;Butylenimine;Azolidine;Perhydropyrrole;NSC 62781;9: PN: WO2017048620 SEQID: 14 claimed sequence
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CAS No:
Description
COLOURLESS-TO-YELLOW LIQUID WITH PUNGENT ODOUR.
Pyrrolidine, also known as tetrahydropyrrole, is an organic compound with the molecular formula (CH2)4NH. It is a cyclic secondary amine, also classified as a saturated heterocycle. It is a colourless liquid that is miscible with water and most organic solvents. It has a characteristic semen-like odor. Compared to acyclic secondary amines, it is about 10 times more basic.
Pyrrolidine appears as a colorless to pale yellow liquid with an ammonia-like odor. Vapors heavier than air. Produces toxic oxides of nitrogen during combustion.|Liquid|COLOURLESS-TO-YELLOW LIQUID WITH PUNGENT ODOUR.|Colourless liquid; Penetrating amine-type aroma
Pyrrolidine appears as a colorless to pale yellow liquid with an ammonia-like odor. Vapors heavier than air. Produces toxic oxides of nitrogen during combustion.|Pyrrolidine is a cyclic amine whose five-membered ring contains four carbon atoms and one nitrogen atom; the parent compound of the pyrrolidine family. It is a saturated organic heteromonocyclic parent, a member of pyrrolidines and an azacycloalkane. It is a conjugate base of a pyrrolidinium ion.
Pyrrolidine Basic Attributes
71.12
71.12
102395
204-648-7
LJU5627FYV
1315
62781
1922
DTXSID3059559
Colorless to pale yellow liq
2933990090
Characteristics
12
0.46
Liquid
0.8520 g/cm3 @ Temp: 22.5 °C
57.69 °C
86.71 °C
37 °F
1.428
Miscible with alcohol, ether, chloroform and water.
Flammables area
128 mm Hg ( 39 °C)
2.45 (vs air)
Oral-Rat LD50: 300 mg/kg; Oral-Mouse LD50: 450 mg/kg
It is flammable in case of open flame, high temperature and oxidant; produces toxic nitrogen oxide gas when heated
1.6-10.6%(V)
Unpleasant, ammoniacal odor
POWERFUL, AMMONIACAL TASTE
2.39e-06 atm-m3/mole|Henry's Law constant = 2.39X10-6 atm-cu m/mol at 25 dec C
pK at 25 °C = 2.89|pKa = 11.31
Hydroxyl radical reaction rate constant = 7.85X10-11 cu cm/molec-sec at 25 °C (est)
Highly flammable. Very soluble in water.
Amines, Phosphines, and Pyridines
Highly Flammable
PYRROLIDINE 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. May generate hydrogen, a flammable gas, in combination with strong reducing agents such as hydrides. An explosion occurred when a mixture of pyrrolidine, benzaldehyde, and propionic acid was heated in an attempt to form porphyrins.
-673.75 Kcal/mol at 298 K and 1 atm
LOWER: 2.9% @ -2 °C, UPPER 13.0% @ 29.8 °C
The vapour is heavier than air and may travel along the ground; distant ignition possible.
Corrosive
529 J/g at 0.1 MPa
Critical temperature: 568.55 K; Critical pressure: 5.6134X10+6 Pa
Safety Information
II
3
UN 1922 3/PG 2
2
11-22-23-34-35-20/21/22-20/22-R35-R20/21/22-R11
16-26-36/37/39-45-33-S45-S36/37/39-S26-S16
UX9650000
F,T,C
The warehouse is ventilated, low temperature and dry; stored separately from oxidants and acids
Stable; flammable. Incompatible with strong acids, strong oxidizing agents.
P210-P280-P305 + P351 + P338-P310
H225-H302 + H332-H314
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
... Can react vigorously with oxidizing materials.|An explosion occurred when benzaldehyde, pyrrolidine and propionic acid were heated to form porphins.
UN 1922
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)|Highly flammable. Gives off irritating or toxic fumes (or gases) in a fire. Vapour/air mixtures are explosive.|Flammable - 3rd degree, Reactive - 1st degree
|Danger|H225 (20.67%): Highly Flammable liquid and vapor [Danger Flammable liquids]|P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P280, P301+P312, P301+P330+P331, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P330, P363, P370+P378, P403+P235, P405, and P501|Aggregated GHS information provided by 1621 companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H225: Highly Flammable liquid and vapor [Danger Flammable liquids]|P210, P233, P240, P241, P242, P243, P260, P264, P270, P271, P280, P284, P301+P310, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P307+P311, P310, P320, P321, P330, P363, P370+P378, P403+P233, P403+P235, P405, and P501
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)|NO open flames, NO sparks, and NO smoking. Closed system, ventilation, explosion-proof electrical equipment and lighting. Use non-sparking handtools. Prevent build-up of electrostatic charges (e.g., by grounding).|PREVENT GENERATION OF MISTS! Prevent inhalation with Ventilation, local exhaust, or breathing protection. Prevent skin contact with Protective gloves. Protective clothing. Prevent eye contact with Face shield or eye protection in combination with breathing protection.|SRP: When working with strong solutions of acids or bases or other caustic or corrosive materials, always wear a full face mask. When working with caustic or corrosive gases or vapors, a full face mask will not protect the eyes or prevent inhaling the material. A full face respirator is required.|Personnel protection: ... Wear appropriate chemical protective gloves, boots and goggles. ... Wear positive pressure self-contained breathing apparatus when fighting fires involving this material.
Dangerous fire hazard when exposed to heat or flame.|Vapor/air mixtures are explosive.
LOWER: 2.9% @ -2 °C, UPPER 13.0% @ 29.8 °C|Explosive limits , vol% in air: 2.9-13.0
Alcohol foam, carbon dioxide, dry chemical|If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical or carbon dioxide.
Remove all ignition sources. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent and remove to safe place. Personal protection: chemical protection suit including self-contained breathing apparatus.
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.|SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.|To prevent ingestion Do not eat, drink, or smoke during work.|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. Attempt to stop leak if without undue personnel hazard. Use water spray to knock-down vapors.|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.
/GUIDE 132: FLAMMABLE LIQUIDS - CORROSIVE/ Fire or Explosion: 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.|/GUIDE 132: FLAMMABLE LIQUIDS - CORROSIVE/ Health: 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.|/GUIDE 132: FLAMMABLE LIQUIDS - CORROSIVE/ Public Safety: CALL Emergency Response Telephone Number on Shipping Paper first. If Shipping Paper not available or no answer, refer to appropriate telephone number listed on the inside back cover. As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering.|/GUIDE 132: FLAMMABLE LIQUIDS - CORROSIVE/ 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.|For more DOT Emergency Guidelines (Complete) data for PYRROLIDINE (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.
Pyrrolidine vapor caused irritation to the skin, eyes, nose and lungs of rats.
Remove all ignition sources. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Personal protection: chemical protection suit including self-contained breathing apparatus.
Fireproof. Separated from strong oxidants and acids. Well closed.
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 and skin. The substance is irritating to the respiratory tract. The substance may cause effects on the nervous system.
NO open flames, NO sparks and NO smoking. Closed system, ventilation, explosion-proof electrical equipment and lighting. Use non-sparking handtools. Prevent build-up of electrostatic charges (e.g., by grounding).
PREVENT GENERATION OF MISTS!
Use ventilation, local exhaust or breathing protection.
Protective gloves. Protective clothing.
Wear face shield or eye protection in combination with breathing protection.
| 2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.| 3 - Liquids and solids that can be ignited under almost all ambient temperature conditions. Materials produce hazardous atmospheres with air under almost all ambient temperatures or, though unaffected by ambient temperatures, are readily ignited under almost all conditions.| 1 - Materials that in themselves are normally stable but that can become unstable at elevated temperatures and pressures.
Pyrrolidine was identified in the primary effluent at a concentration of 14 ug/L from municipal wastewater treatment plants(1).
Cigarettes contain 42 ug/cigarette of pyrrolidine(1). When smoked, 20 ug/cigarette of pyrrolidine is released (5 ug inhaled by smoker, 15 ug released into the environment)(1).|In tobacco & cigarette smoke condensate (tar), pyrrolidine was one of predominant amines found in both substances.
Toxicity
highly toxic
Formation of n-nitrosopyrrolidine in a dog's stomach from Na nitrate & pyrrolidine. N-nitrosopyrrolidine disappeared rapidly from stomach, probably due to absorption.
LD50 Rat oral 300 mg/kg|LC50 Mouse inhalation 1300 mg/cu m/2 hr|LD50 Mouse iv 56 mg/kg|For more Non-Human Toxicity Values (Complete) data for PYRROLIDINE (8 total), please visit the HSDB record page.
FOUND IN TOBACCO & CARROT LEAVES. PROBABLE BIOSYNTHESIS FROM ORNITHINE & PUTRESCINE.|Pyrrolidine was detected in spinach(1,2) and miso(1). Pyrrolidine was also detected in red radish, celery, maize, apple peels, beans, kale, paprika red, cornichons, barley, hops, and malt(2).
Pyrrolidine's production and use in the synthesis of drugs and antibiotics(1) and in vulcanization accelerators(1) may result in its release to the environment through various waste streams.
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 42(SRC), determined from a log Kow of 0.46(2) and a regression-derived equation(3), indicates that pyrrolidine is expected to have very high mobility in soil(SRC). The pKa of pyrrolidine is 11.31(4), indicating that this compound will primarily exist in the cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5). Volatilization of pyrrolidine from moist soil surfaces is not expected to be an important fate process as cations do not volatilize(SRC). Pyrrolidine is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 62.7 mm Hg(6). Pyrrolidine was found to degrade anaerobically via denitrification in 7-15 days in microbial consortia from freshwater sediments, estuarine sediments and activated sludge(7).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 42(SRC), determined from a log Kow of 0.46(2) and a regression-derived equation(3), indicates that pyrrolidine is not expected to adsorb to suspended solids and sediment(SRC). A pKa of 11.31(4) indicates pyrrolidine will exist almost entirely in the cation form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(5). According to a classification scheme(6), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Pyrrolidine was found to degrade anaerobically via denitrification in 7-15 days in microbial consortia from freshwater sediments, estuarine sediments and activated sludge(8).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), pyrrolidine, which has a vapor pressure of 62.7 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase pyrrolidine 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 5 hours(SRC), calculated from its rate constant of 7.8X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Pyrrolidine does not contain chromophores that absorb at wavelengths >290 nm(4) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
The rate constant for the vapor-phase reaction of pyrrolidine with photochemically-produced hydroxyl radicals has been estimated as 7.8X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 5 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Pyrrolidine is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). Pyrrolidine does not contain chromophores that absorb at wavelengths >290 nm(2) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
An estimated BCF of 3 was calculated in fish for pyrrolidine(SRC), using a log Kow of 0.46(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 pyrrolidine is estimated as 42(SRC), using a log Kow of 0.46(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that pyrrolidine is expected to have very high mobility in soil. The pKa of pyrrolidine is 11.31(4), indicating that this compound will primarily exist in the cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5).
The Henry's Law constant for pyrrolidine is 2.39X10-6 atm-cu m/mole(1). A pKa of 11.31(1) indicates pyrrolidine will exist almost entirely in the cation form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(2). Pyrrolidine is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 62.7 mm Hg(3).
SURFACE WATER: Pyrrolidine was detected in the Alster, Au, Kruckau and Pinnau rivers of Germany at 1.5 ug/kg, 2.5 ug/kg, 0.2 ug/kg, and 0.9 ug/kg, respectively(1).
Pyrrolidine was detected in 10 g samples of baked ham at 0.013 ppm(1). Pyrrolidine can be found in tilsiter, camembert, limburger, and brown bread cheeses at 19.9 mg/kg, 1 mg/kg, 0.1 mg/kg and 0.3 mg/kg, respectively(2). In coffee, pyrrolidine was detected in coffee extract and freeze dried coffee at 10 mg/kg and 11 mg/kg, respectively(3).
Occupational exposure to pyrrolidine may occur through inhalation and dermal contact with this compound at workplaces where pyrrolidine is produced or used. Monitoring and use data indicate that the general population may be exposed to pyrrolidine via ingestion of food and drinking water, use of tobacco products, and dermal contact with this compound and other products containing pyrrolidine. (SRC)
Drug Information
Pyrrolidine, one of biogenic volatile amines, possesses nicotine-like synaptotropic actions on the nervous systems. Pyrrolidine levels in the tissue were examined by using mass fragmentographic technique. High concn of pyrrolidine were found in the seminal vesicle and lung of rabbits. Only trace amt of pyrrolidine existed in the brain of mice and rats, although higher concn were detected in the brain of rabbits. In the rat brain, however, high levels of pyrrolidine were found in the pineal gland, pituitary gland and corpus striatum.
When orally admin, secondary amine pyrrolidine, which is present in normal human urine, was converted to n-nitrosamines in the Escherichia coli-infected bladder of rats.|When microsomes and post-microsomal supernatant are used together, 4 major products are produced, 2 of which can be shown to arise from the major microsomal product. Several of these products have been isolated and 1 of the major products has been tentatively identified as piperidine.|Formation of n-nitrosopyrrolidine in a dog's stomach from Na nitrate & pyrrolidine. N-nitrosopyrrolidine disappeared rapidly from stomach, probably due to absorption.|Carcinogen n-nitrosopyrrolidine formed from free proline via pyrrolidine.
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)
Fresh air, rest. 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.
Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). 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 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mg/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 dry sterile dressings after decontamination ... . /Organic bases/Amines and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. If patient is unresponsive to these measures, vasopressors may be helpful. 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. ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Organic bases/Amines and related compounds/
/SIGNS AND SYMPTOMS/ Inhalation: Burning sensation. Convulsions. Cough. Headache. Nausea. Sore throat. Vomiting. Skin: Redness. Skin burns. Pain. Blisters. Eyes: Redness. Pain. Blurred vision. Severe deep burns. Ingestion: Convulsions. Sore throat. Vomiting. (See Inhalation).
pyrrolidine
The substance can be absorbed into the body by inhalation and by ingestion.
Burning sensation. Convulsions. Cough. Headache. Nausea. Sore throat. Vomiting.
Redness. Skin burns. Pain. Blisters.
Redness. Pain. Blurred vision. Severe deep burns.
Pyrrolidine Use and Manufacturing
Reaction of 1,4-butanediol and ammonia over a dehydration catalyst|Usually prepared by reduction of pyrrole.|Pyrrolidine can be produced from butanediol and ammonia, e.g., over an aluminum thorium oxide catalyst at 300 °C or over a nickel catalyst at 200 °C and 20 MPa under hydrogenation conditions. It can also be produced from tetrahydrofuran and ammonia over aluminum oxide at 275-375 °C.|Production can be obtained by reaction of 1,4-dihydroxyalkanes with amines in the presence of dehydrating agents at elevated temperatures or by reaction of primary amines with 1,4-dihaloalkanes. The dry distillation of 1,4-butanediamine dihydrochloride also generates pyrrolidine.|Via overall 5-endo-trig cyclizations of homoallylic tosylamides.
A heterocyclic compound used as a building block in the synthesis of wide range of pharmaceutical compounds, namely matrix metalloprotein inhibitors (MMPIs) and aminopeptidase N inhibitors (APNIs).
Intermediates
Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#360]
Grades: 95% min purity
All other basic organic chemical manufacturing|Pyrrolidine: ACTIVE|A study of the rates of the competitive nitrosations of pyrrolidine, p-cresol & l-cysteine hydrochloride. Formation of n-nitrosopyrrolidine was observed only in reactions done @ 120 °C.
IDENTIFICATION OF PYRROLIDINE BY GLC-MS (MASS SPECTROMETRY) IN PLANT-DERIVED MATERIAL.|A SIMPLE AND SELECTIVE GAS CHROMATOGRAPHIC METHOD WAS ESTABLISHED FOR DETERMINING NATURALLY OCCURRING SECONDARY AMINES.|HIGH PRESSURE LIQUID CHROMATOGRAPHY USED TO DETERMINE ALIPHATIC SECONDARY AMINES IN MEAT AND FISH PRODUCTS.
Food additives -> Flavoring Agents|Flavoring Agents -> JECFA Flavorings Index|Fire Hazards -> Flammable - 3rd degree, Reactive - 1st degree
Flavoring Agents
Analysis Methods
| Name | Column Shape | Active Phase(℃) | Retention index | Temperature Control | Method | Comments | Reference |
|---|---|---|---|---|---|---|---|
| Kovats' RI, non-polar column, isothermal | Capillary | OV-101 | 692. | 110. | isothermal | 50. m/0.3 mm/0.4 μm, He | Zhuravleva, I.L.Evaluation of the polarity and boiling points of nitrogen-containing heterocyclic compounds by gas chromatographyRuss. Chem. Bull. (Engl. Transl.)2000, 49, 2, 325-328. |
| Kovats' RI, non-polar column, isothermal | Packed | C78, Branched paraffin | 674.9 | 130. | isothermal | Chromosorb G HP; Column length: 3.3 m | Reddy, K.S.Dutoit, J.-Cl.Kovats, E. sz.Pair-wise interactions by gas chromatography. I. Interaction free enthalpies of solutes with non-associated primary alcohol groupsJ. Chromatogr.1992, 609, 1-2, 229-259. |
| Kovats' RI, non-polar column, isothermal | Packed | Apolane | 680. | 130. | isothermal | Column length: 3.7 m | Dutoit, J.Gas chromatographic retention behaviour of some solutes on structurally similar polar and non-polar stationary phasesJ. Chromatogr.1991, 555, 1-2, 191-204. |
| Kovats' RI, non-polar column, isothermal | Packed | Apiezon L | 690. | 100. | isothermal | N2 or He, Chromosorb G, AW; Column length: 2.7 m | Zhuravleva, I.L.Kapustin, Yu.P.Golovnya, P.B.Retention indices of some isoaliphatic and heterocyclic nitrogenous basesZh. Anal. Khim.1976, 31, 1378-1380. |
| Kovats' RI, non-polar column, isothermal | Packed | PMS-100 | 645. | 130. | isothermal | He, Celite 545 (44-60 mesh); Column length: 3. m | Anderson, A.Jurel, S.Shymanska, M.Golender, L.Gas-liquid chromatography of some aliphatic and heterocyclic mono- and pollyfunctional amines. VII. Retention indices of amines in some polar and unpolar stationary phasesLatv. PSR Zinat. Akad. Vestis Kim. Ser.1973, 1, 51-63. |
Computed Properties
Molecular Weight:71.12
XLogP3:0.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:71.073499291
Monoisotopic Mass:71.073499291
Topological Polar Surface Area:12
Heavy Atom Count:5
Complexity:22.8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Recommended Suppliers of Pyrrolidine
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