Related articles - What is OTTOFUELII?
- Otto Fuel II (OFII) was developed by Dr Otto Reitlinger and introduced by the United States Navy in the mid-1960s as a monopro....
- Oct 14，2021
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| | OTTOFUELII Basic information |
| Product Name: | OTTOFUELII | | Synonyms: | OTTOFUELII;Ottokraftstoffe, als krebserzeugend (R45) gekennzeichnet | | CAS: | 106602-80-6 | | MF: | | | MW: | 0 | | EINECS: | | | Product Categories: | | | Mol File: | Mol File | ![OTTOFUELII Structure]() |
| | OTTOFUELII Chemical Properties |
| RIDADR | 2810 | | HazardClass | 6.1 | | PackingGroup | III |
| | OTTOFUELII Usage And Synthesis |
| Description | Otto Fuel II (OFII) was developed by Dr Otto Reitlinger and
introduced by the United States Navy in the mid-1960s as
a monopropellant, a propellant consisting of a chemical or
mixture that can function on its own without the addition of
a separate substance. It is amixture of three chemical constituents,
propylene glycol dinitrate, dibutyl sebacate, and 2-nitrodiphenylamine,
and has been primarily used as a torpedo
propellant due to its ability to combust in the absence of oxygen.
The development of OFII was significant given that it increased
the speed and range of torpedoes, and despite 50 years in operation,
it currently remains in use as a premier torpedo propellant. | | Uses | OFII is used as a propellant for torpedoes and other weapons
systems. OFII exists as a reddish-orange, oily liquid with a distinct odor and is a mixture of three chemicals, propylene
glycol dinitrate (76%), dibutyl sebacate (22%), and 2-nitrodiphenylamine
(1.5%). The largest component of OFII is
propylene glycol dinitrate, a colorless liquid also known as
1,2-propylene glycol dinitrate, PGDN, or 1,2-propanediol
dinitrate. Propylene glycol dinitrate is a nitrated ester that
constitutes the explosive portion of OFII. OFII’s toxicity is
largely associated with propylene glycol dinitrate.
Dibutyl sebacate, a clear liquid, is added to OFII as
a desensitizing agent to stabilize the mixture. Although
a significant fraction of OFII, dibutyl sebacate is also used in the
production of plastics, including those used for packaging
food, and as a flavor enhancer in foods such as nonalcoholic
beverages, ice creams, candies, and baked goods. Additionally,
it is used as a lubricant in shaving creams. Alternative names for
dibutyl sebacate are decanedioic acid, dibutyl ester, sebacic
acid, and dibutyl decanedioate. The final component of OFII is
2-nitodiphenylamine, a solid that serves as a stabilizer to
control the explosion of propylene glycol dinitrate. It is also
used as a solvent dye. 2-Nitrodiphenylamine is also referred to
as 2-nitrobenzenamine, 2-nitro-N-phenyl, 2-nitro-N-phenylaniline,
and Sudan Yellow 1339. | | Safety Profile | Experimental reproductive effects. When heated to decomposition it emits acrid smoke and irritating vapors. | | Environmental Fate | OFII enters the environment as its three separate chemical
components, with each partitioning into the environment at
rates dependent on their individual chemical and physical
properties. OFII has a relatively low vapor pressure indicating
that little evaporation occurs. OFII is mainly released in water
in waste streams from facilities involved in production or
torpedo rework operations. Limited data on the environmental
fate of OFII indicate that propylene glycol dinitrate is removed
from the water by volatilization, and neither 2-nitrodiphenylamine
nor dibutyl sebacate is volatile or soluble enough for the
partitioning to air or water to be significant fate processes.
2-Nitrodiphenylamine tends to precipitate and has been
detected in river sediments receiving wastewater runoff; this is
considered its most likely fate. Data on biodegradation of
propylene glycol dinitrate and 2-nitrodiphenylamine are
mixed. Some studies indicate that these compounds may
biodegrade while other experiments indicate that these
components are largely recalcitrant to degradation. Dibutyl
sebacate is rapidly biodegraded by a variety of microorganisms.
Propylene glycol dinitrate and 2-nitrodiphenylamine are
photolyzed and photooxidized in water and it is likely that
these substances are similarly broken down in the air.
A bioaccumulation factor has been estimated only for
2-nitrodiphenylamine and indicates that it does not bioconcentrate
in aquatic organisms or biomagnify in the food
chain. More information on the bioconcentration potential of these chemicals, including experimental data, is necessary to
assess the biomagnification risk in the food chain. | | Toxicity evaluation | The mechanism of toxicity for OFII is associated with its major
component, propylene glycol dinitrate. Propylene glycol dinitrate
is an organic nitrate and therefore shares the vasodilating
capacity of therapeutic nitrates, such as nitroglycerin used for
treatment of angina pectoris. Organic nitrates cause peripheral vasodilation, decreased ventricular ejection time, relaxation,
and a longer period of coronary blood flow.
An early consequence of overexposure to propylene glycol
dinitrate (or OFII) is the vasodilation of the cerebral vessels,
which is considered the major contributor in the development
of the typical trinitrotoluene headache. In cases of more severe
overexposure, relaxation of the vascular smooth muscle can
cause a decrease in blood pressure followed by a compensatory
vasoconstriction. The magnitude of the vasodilating effect has
been shown to decrease following repeated exposure to organic
nitrates. While the mechanism for organic nitrate tolerance is
not understood, possibilities include the depletion of sulfhydryl
groups at the receptor sites, reduced availability or activity
of the active intermediate S-nitrosothiol, and alterations in the
pharmacokinetics leading to decreased nitrate concentrations
in vascular tissues. Extreme overexposure to propylene glycol
dinitrate can produce toxic levels of methemoglobin, a property
shared by many organic and inorganic nitrates and also by
aromatic amines, including 2-nitrodiphenylamine. This effect
is significant given that methemoglobin is unable to reversibly
combine with oxygen and carbon dioxide and causes a shift in
the oxygen dissociation curve toward increased oxygen affinity,
inhibiting oxygen transfer from the blood to the tissues. The
mechanism of dibutyl sebacate toxicity is unknown. |
| | OTTOFUELII Preparation Products And Raw materials |
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