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Home > Encyclopedia > Methylcyclopentadienylmanganese tricarbonyl

Methylcyclopentadienylmanganese tricarbonyl

Methylcyclopentadienylmanganese tricarbonyl structure

Methylcyclopentadienylmanganese tricarbonyl 

structure
  • CAS No:

    12108-13-3

  • Formula:

    C9H7MnO3

  • Chemical Name:

    Methylcyclopentadienylmanganese tricarbonyl

  • Synonyms:

    Manganese,tricarbonyl[(1,2,3,4,5-η)-1-methyl-2,4-cyclopentadien-1-yl]-;Manganese,tricarbonyl(methyl-π-cyclopentadienyl)-;Manganese,tricarbonyl(methylcyclopentadienyl)-;Methylcyclopentadienylmanganese tricarbonyl;Tricarbonyl[(1,2,3,4,5-η)-1-methyl-2,4-cyclopentadien-1-yl]manganese;π-Methylcyclopentadienylmanganese tricarbonyl;Tricarbonyl(methylcyclopentadienyl)manganese;Tricarbonyl(2-methylcyclopentadienyl)manganese;(Methylcyclopentadienyl)tricarbonylmanganese;2-Methylcyclopentadienylmanganese tricarbonyl;Methylcymantrene;Tricarbonyl(methyl-π-cyclopentadienyl)manganese;MMT;Tricarbonyl(η5-methylcyclopentadienyl)manganese;Tricarbonyl(η5-methylcyclopentadienyl)manganese(I);Ethyl MMT;Hitec 3000;NSC 22316;Hitec 3062;41536-42-9

  • Categories:

    Organic Chemistry  >  Organometallic Compounds

Description

DARK ORANGE LIQUID WITH CHARACTERISTIC ODOUR.

Methylcyclopentadienylmanganese tricarbonyl Basic Attributes

218.09

217.97800

235-166-5

1E52JN2L3I

1169

2810

Dark orange liquid|Yellow to dark orange [Note: A solid below 36 degrees F].

Characteristics

0.00000

0.78760

yellow liquid

1.39 g/cm3 @ Temp: 20 °C

2.2 °C

233 °C

205 °F

n20/D 1.584(lit.)

Insoluble in water. soluble in hydrocarbon solvents, alcohols, ether, acetone

Poison room

0.05 mm Hg ( 20 °C)

>1 (vs air)

Oral-Rat  LD50: 8 mg/kg; Oral-Mouse  LD50: 34 mg/kg

Flammable; decomposes toxic manganese oxide fumes in the fire

Herbaceous odor|Faint, pleasant odor

Henry's Law constant = 0.019 atm-cu m/mol @ 25 °C

Manganese comprises about 25% of /MMT's/ molecular weight.|Half-life a few seconds in air; decomposes rapidly in sunlight

Safety Information

II

6.1

UN 3281 6.1/PG 2

3

23/24/25-40-50/53-48/23-38-26-24/25

23-26-36/37/39-45-61-60-36/37-28

OP1450000

T,N,T+

Treasury is low temperature, ventilated, dry; stored separately from food raw materials

Stable. Incompatible with strong oxidizing agents.

P260; P273; P280; P284; P301 + P310; P302 + P350

H301; H310 + H330; H315; H372; 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.

Light (decomposes).

Lynam DR et al; Environmental Assessment of MMT Fuel Additive; Sci Total Environ 93: 107-14 (1990)

Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Above 96 °C explosive vapour/air mixtures may be formed.|Flammable - 2nd degree

Use water spray, powder, foam, carbon dioxide.

... PREVENTIVE MEASURE TO AVOID SKIN CONTACT & INHALATION OF VAPORS & PREVENTING SPILLS. RECOMMENDED PROTECTIVE CLOTHING FOR NORMAL WORK INVOLVING POTENTIAL SPILLS & CONTAMINATION ARE IMPERVIOUS GLOVES, BOOTS, APRON & ORGANIC VAPOR RESPIRATOR. IF ODOR OF MATERIAL IS PRESENT, MASK SHOULD BE WORN.|UNDER CERTAIN CIRCUMSTANCES OXYGEN (AIR) BREATHING APPARATUS SHOULD BE USED.|Wear appropriate personal protective clothing to prevent skin contact.|Wear appropriate eye protection to prevent eye contact.

IN EVENT OF SPILLS, ONLY CERTAIN SOLVENTS HAVE PROVEN TO BE SATISFACTORY THUS FAR. LARGE SPILLS CAN BE "CLEANED UP" USING JP-4 OR JP-5 (JET ENGINE FUELS). ISOPROPYL ALC MAY BE USED TO "CLEAN UP" MODERATE SPILLS, WHILE METHYL ETHYL KETONE SHOULD BE USED FOR CLEANING SMALL SPILLS & QUICK DISCONNECTS.

CONTAMINATED CLOTHING SHOULD BE REMOVED IMMEDIATELY FOLLOWED BY THOROUGH WASHING OF CONTAMINATED SKIN & DECONTAMINATION OF CLOTHING & EQUIPMENT IS ESSENTIAL.|Although manganese carbonyls can be absorbed through the skin, MMT is not strongly irritating to the skin or eye. Therefore, exposed workers should be cautioned not to depend on irritation as a warning sign of exposure. They should be instructed to wash the skin and change their clothing as soon as contamination with MMT occurs.|SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.|The worker should immediately wash the skin when it becomes contaminated.|For more Preventive Measures (Complete) data for METHYLCYCLOPENTADIENYL MANGANESE TRICARBONYL (6 total), please visit the HSDB record page.

MODERATELY IRRITATING TO EYES.

Vacated 1989 OSHA PEL TWA 0.2 mg/cu m, as Mn, skin designation, is still enforced in some states.|Permissible Exposure Limit: Table Z-1 Ceiling value: 5 mg/cu m. /Manganese cmpd (as Mn)/

Recommended Exposure Limit: 10 Hr Time-Weighted avg: 0.2 mg/cu m (skin).|Recommended Exposure Limit: 10 Hr Time-Weighted Avg: 1 mg/cu m. /Manganese compounds and fume (as Mn)/|Recommended Exposure Limit: 15 Min Short-Term Exposure Limit: 3 mg/cu m. /Manganese compounds and fume (as Mn)/

Personal protection: chemical protection suit including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Collect leaking liquid in sealable containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

Separated from food and feedstuffs.

The substance is irritating to the eyes and skin. The substance may cause effects on the central nervous system, kidneys, liver and lungs. This may result in tissue lesions. Exposure at high levels could cause death. Medical observation is indicated.

NO open flames. Above 96 °C use a closed system and ventilation.

PREVENT GENERATION OF MISTS! STRICT HYGIENE!

Use ventilation, local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear safety spectacles or eye protection in combination with breathing protection.

Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. Methylcyclopentadienyl manganese tricarbonyl is included on this list.|... Substances for which a Federal Register notice has been published that included consideration of the serious health effects, including cancer, form ambient air exposure to the substance. Manganese (50 FR 32627; Aug. 13, 1985) is included on this list. /Manganese/

Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Manganese, tricarbonyl methylcyclopentadienyl is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 100 lbs.

URBAN/SUBURBAN: In urban areas of the United States without major foundries, mean annual concns of manganese range from 0.03-0.07 ug/cu m(1). In areas with foundries, the mean annual concns of manganese range from 0.2-0.3 ug/cu m(1). Taxi drivers in Toronto, Canada, where methylcyclopentadienyl manganese tricarbonyl (MMT) has been used in gasoline since 1976, are exposed to approximately 0.001-0.03 ug/cu m of respirable manganese and 0.002-0.04 ug/cu m of total manganese in air while driving on urban and suburban roads(2).

Toxicity

most toxic

LD50 Rabbit dermal 140-795 mg/kg|LD50 Rat single intragastric 58 mg/kg|LD50 Mouse single intragastric 230 mg/kg|LC50 Rat inhalation 247 mg/cu m/1 hr|For more Non-Human Toxicity Values (Complete) data for METHYLCYCLOPENTADIENYL MANGANESE TRICARBONYL (8 total), please visit the HSDB record page.

IN ITS CONCENTRATED FORM CMPD IS HIGHLY TOXIC BY ALL ROUTES OF EXPOSURE - BY INHALATION OF VAPORS, INGESTION OF LIQUID & BY PERCUTANEOUS ABSORPTION.

Drug Information

VERY QUICKLY AFTER INHALATION, THERE IS PROMPT INCREASE IN URINARY MANGANESE, WITH 95% OR MORE OF THAT ABSORBED BEING EXCRETED IN URINE. EXCRETION OF MANGANESE RETURNS TO NORMAL RANGE OF 1-8 UG/L IN ABOUT 2-3 DAYS.|/2-METHYLCYCLOPENTADIENYL MANGANESE TRICARBONYL/ ... PENETRATES SKIN VERY RAPIDLY.|IN RATS FOLLOWING ORAL & IV ADMIN OF MMT, RAPID EXCRETION OF (54) MANGANESE OCCURRED. EXTRACTION OF URINE & FECES INDICATED THAT (54) MANGANESE WAS EXCRETED IN INORG FORM. HIGH LEVELS OF (54) MANGANESE FOUND IN URINE ARE NOT TYPICAL OF NORMAL MANGANESE EXCRETION. LIVER, KIDNEYS, & LUNGS CONTAINED HIGHEST CONCN.|GASOLINE SOLN ARE NOT AS READILY ABSORBED AS IS THE PURE MATERIAL.|For more Absorption, Distribution and Excretion (Complete) data for METHYLCYCLOPENTADIENYL MANGANESE TRICARBONYL (8 total), please visit the HSDB record page.

METABOLIC ASPECTS OF METHYLCYCLOPENTADIENYL MANGANESE TRICARBONYL (MMT) WAS STUDIED IN RATS FOLLOWING ORAL & IV DOSING. EXTRACTION OF URINE & FECES INDICATED THAT MMT WAS METABOLIZED & THAT THE (54) MANGANESE WAS EXCRETED IN INORGANIC FORM.|ORALLY ADMIN (3)H-MMT WAS METABOLIZED & EXCRETED IN URINE AS 2 MAJOR METABOLITES, (CO)3MNC5H4CO2H & (CO)3MNC5H4CH2OH, WHICH ACCOUNTED FOR 67% & 14% OF URINARY (3)H, RESPECTIVELY.

Fresh air, rest. Artificial respiration may be needed. Refer for medical attention.


Remove contaminated clothes. Rinse and then wash skin with water and soap.


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. 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 ... . 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 ... . /Manganese and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or in severe respiratory distress. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors for hypotension with a normal fluid volume. Watch for signs of fluid overload ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Manganese and related compounds/

CI-2 IS MODERATELY IRRITATING TO EYES, BUT IS NOT IRRITATING TO SKIN ON SINGLE CONTACT & IS NOT KNOWN TO CAUSE CUTANEOUS SENSITIZATION. ... IT DOES PENETRATE SKIN VERY RAPIDLY. ... 5-15 ML, WHEN SPILLED ON ONE HAND & WRIST OF WORKER ALLEGEDLY CAUSED "THICK TONGUE", GIDDINESS, NAUSEA & HEADACHE WITHIN 3 TO 5 MIN.|WHEN ENCOUNTERED IN CONCN FORM, MATERIAL IS HIGHLY TOXIC & PENETRATES SKIN READILY. WHEN BLENDED WITH FUELS, IT HAS LOW ORDER OF TOXICITY. ... THIS IS QUITE PARALLEL TO THE TOXICITY OF TETRAETHYL LEAD.|While no epidemiologic or other systematic studies of workers exposed to organic manganese compounds have been reported, a few episodes of inadvertent worker exposure have been documented by the manufacturer of MMT. It appears that transfer of the liquid provides opportunities for contamination of clothes and dermal exposure. In one incident two men wearing rubber gloves and air masks got their clothing (shoes and socks, in particular) wet with MMT. They kept working for about 1.5 hours before they changed clothes and reported to the medical department. They had no symptoms other than a slight burning sensation on the skin. No abnormalities were found on physical examination. Urinary manganese levels on the same day were 46 and 137 ug/l, and dropped to 2.9 and 3.4 ug/l respectively, a few weeks later. In another incident in which six workers were dermally exposed for up to 30 minutes, headache was reported by four, nausea by four, dyspnea by three, chest tightness by one, and paresthesia by one. These symptoms appeared five minutes to an hour after exposure and subsided in two hours in four cases; the remaining two reported abdominal distress for two days.

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

Abdominal pain. Dizziness. Headache. Laboured breathing. Nausea. Cough. Sore throat.


MAY BE ABSORBED! Redness. Pain.


Redness. Pain.

Methylcyclopentadienylmanganese tricarbonyl Use and Manufacturing

Methods of Manufacturing

Methylcyclopentadiene with manganese carbonyl.|Manganese(II) chloride is allowed to react with cyclopentadienylmagnesium bromide to form biscyclopentadienylmanganese, an intermediate that reacts with carbon monoxide to give the tricarbonyl; this is then methylated in the presence of Friedel-Crafts catalysts.

Uses

Antiknock fuel additive; dopant for Mn.

Production

(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS|(1976) PROBABLY GREATER THAN 2.27X10+6 GRAMS

As of 1983, MMT was used in about 25% of all regular leaded gasoline in the US and in all unleaded gasoline in Canada, at a rate of 0.03-0.04 g (as manganese) per US gallon.

GAS CHROMATOGRAPHY ATOMIC ABSORPTION SPECTROMETRY WAS USED TO DETERMINE METHYLCYCLOPENTADIENYLMANGANESETRICARBONYL IN AIR SAMPLES.

GAS CHROMATOGRAPHIC DETERMINATION OF METHYLCYCLOPENTADIENYLMANGANESETRICARBONYL IN BIOLOGICAL TISSUES AND FLUIDS.

Fire Hazards -> Flammable - 2nd degree

Computed Properties

Molecular Weight:218.09
Hydrogen Bond Acceptor Count:4
Exact Mass:217.977562
Monoisotopic Mass:217.977562
Topological Polar Surface Area:3
Heavy Atom Count:13
Formal Charge:-1
Complexity:43.3
Covalently-Bonded Unit Count:5
Compound Is Canonicalized:Yes

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