110-22-5 Usage
Chemical Properties
Different sources of media describe the Chemical Properties of 110-22-5 differently. You can refer to the following data:
1. colourless liquid with a pungent odour.
2. Diacetyl peroxide as a commercial product is a colorless
liquid with a pungent odor. As a solid it is crystalline (sandlike)
with a sharp odor. The commercial product consists of a
25%solution of acetyl peroxide in dimethyl phthalate. It is an
organic peroxide and a carboxylic peracid derivative. It sinks
in water. Diacetyl peroxide is a colorless crystal. It must be
kept in solution because of its shock sensitivity and high
explosion risk.
Uses
Diacetyl peroxide diluted solutions with<25% strength are used as free-radicalsources to initiate polymerizations and inorganic syntheses.
General Description
Colorless liquid with a sharp odor. Consists of a solution of acetyl peroxide in dimethyl phthalate. Sinks in water.
Reactivity Profile
Peroxides, such as ACETYL PEROXIDE, are good oxidizing agents. Organic compounds can ignite on contact with concentrated peroxides. Strongly reduced material such as sulfides, nitrides, and hydrides may react explosively with peroxides. There are few chemical classes that do not at least produce heat when mixed with peroxides. Many produce explosions or generate gases (toxic and nontoxic). Generally, dilute solutions of peroxides (<70%) are safe, but the presence of a catalyst (often a transition metal such as cobalt, iron, manganese, nickel, or vanadium) as an impurity may even then cause rapid decomposition, a buildup of heat, and even an explosion. Solutions of peroxides often become explosive when evaporated to dryness or near-dryness.
Health Hazard
Different sources of media describe the Health Hazard of 110-22-5 differently. You can refer to the following data:
1. Contact with liquid causes irritation of eyes and skin. If ingested, irritates mouth and stomach.
2. The concentrated compound is a severe eyehazard. An amount of 60 mg in a 1-minuterinse caused severe irritation in rabbit’s eyes.Skin contact of its solution may cause irritation.Toxicity of this compound should be oflow order. Diacetyl peroxide caused lung andblood tumors in rats. Its carcinogenic actionon humans is not reported.
Fire Hazard
Behavior in Fire: May explode. Burns with accelerating intensity.
Safety Profile
Severe skin and eye irritant. Questionable carcinogen with experimental tumorigenic data. Dangerous fire hazard by spontaneous chemical reaction. A powerful oxidizing agent; can cause ignition of organic materials on contact. Severe explosion hazard when shocked or exposed to heat. It may explode spontaneously in storage and should be used as soon as prepared. It will react with water or steam to produce heat; can react vigorously with reducing materials; emits toxic fumes on contact with acid or acid fumes. To fight fire, use CO2, dry chemical.
27' and not warmed over 30'. Do not add to hot materials. Do not add accelerator to this material. Store in origmal container with vented cap. Avoid bodily contact. This material is nearly always stored and handled as a 25% solution in an inert solvent. See also ACETYL PEROXIDE 25% solution (in dimethyl phthalate); and PEROXIDES, ORGANIC. Storage
storage
Diacetyl peroxide is stored and shipped as a25% solution in dimethyl phthalate; the storagetemperature must not go down below-5°C (23°F) or above 32°C (89.6°F); it isstored in a cool and well-ventilated areaisolated from other chemicals and protectedfrom physical damage. Concentration, maximumto 25%, can be shipped in amber bottlesor polyethylene carboy containers with ventcaps not exceeding 10 and 45 lb.
Waste Disposal
It is ignited on the ground in a remoteoutdoor area using a long torch. Rinse theempty containers with 5–10% caustic sodaor caustic potash solution.
Check Digit Verification of cas no
The CAS Registry Mumber 110-22-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 0 respectively; the second part has 2 digits, 2 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 110-22:
(5*1)+(4*1)+(3*0)+(2*2)+(1*2)=15
15 % 10 = 5
So 110-22-5 is a valid CAS Registry Number.
InChI:InChI=1/C4H6O4/c1-3(5)7-8-4(2)6/h1-2H3
110-22-5Relevant articles and documents
Ogata et al.
, p. 838,839 (1965)
Generation of mono- and bis-dioxiranes from 2,3-butanedione
Sawwan, Nahed,Greer, Alexander
, p. 5796 - 5799 (2006)
Biacetyl reacts with oxone to give bis-dioxirane [3,3′-dimethyl-3, 3′-bidioxirane, 3B] and mono-dioxirane [1-(3-methyl-dioxiran-3-yl) ethanone, 3A)]. Bis-dioxirane 3B is formed when two oxygens are incorporated into biacetyl, while mono-dioxirane 3A incorporated only one. A greater stability is observed in 3B compared to 3A, which is attributed to an α-dioxiranyl (anomeric) effect in the former. In contrast, 3A suffers from a destabilizing π-electron withdrawing effect from the adjacent carbonyl group.
The Role of Iodanyl Radicals as Critical Chain Carriers in Aerobic Hypervalent Iodine Chemistry
Hyun, Sung-Min,Yuan, Mingbin,Maity, Asim,Gutierrez, Osvaldo,Powers, David C.
supporting information, p. 2388 - 2404 (2019/09/12)
Selective O2 utilization remains a substantial challenge in synthetic chemistry. Biological small-molecule oxidation reactions often utilize aerobically generated high-valent catalyst intermediates to effect substrate oxidation. Available synthetic methods for aerobic oxidation catalysis are largely limited to substrate functionalization chemistry by low-valent catalyst intermediates (i.e., aerobically generated Pd(II) intermediates). Motivated by the need for new chemical platforms for aerobic oxidation catalysis, we recently developed aerobic hypervalent iodine chemistry. Here, we report that in contrast to the canonical two-electron oxidation mechanisms for the oxidation of organoiodides, the developed aerobic hypervalent iodine chemistry proceeds via a radical chain mechanism initiated by the addition of aerobically generated acetoxy radicals to aryl iodides. Despite the radical chain mechanism, aerobic hypervalent iodine chemistry displays substrate tolerance similar to that observed with traditional terminal oxidants, such as peracids. We anticipate that these insights will enable new sustainable oxidation chemistry via hypervalent iodine intermediates. O2 is routinely utilized in biological catalysis to generate high-valent catalyst intermediates that engage in substrate oxidation chemistry. Analogous synthetic chemistry via aerobically generated high-valent intermediates would enable new sustainable synthetic methods but is largely unknown because of the challenges in selective O2 utilization. We have developed aerobic hypervalent iodine chemistry as a platform for coupling O2 reduction with a diverse set of substrate functionalization mechanisms. Many of the synthetic applications of hypervalent iodine reagents rely on selective two-electron oxidation-reduction chemistry. Here, we report that one-electron oxidation reactions pathways via iodanyl radical intermediates are critical in aerobic hypervalent iodine chemistry. The new appreciation for the critical role that iodanyl radicals can play in the synthesis of hypervalent iodine compounds will provide new opportunities in sustainable oxidation catalysis. Aerobic hypervalent iodine chemistry provides a strategy for coupling the one-electron chemistry of O2 with two-electron processes typical of organic synthesis. We show that in contrast to the canonical two-electron oxidation of aryl iodides, aerobic synthesis proceeds by a radical chain process initiated by the addition of aerobically generated acetoxy radicals to aryliodides to generate iodanyl radicals. Robustness analysis reveals that the developed aerobic oxidation chemistry displays substrate tolerance similar to that observed in peracid-based methods and thus holds promise as a sustainable synthetic method.
Palladium-catalyzed ortho-functionalization of azoarenes with aryl acylperoxides
Qian, Cheng,Lin, Dongen,Deng, Yuanfu,Zhang, Xiao-Qi,Jiang, Huanfeng,Miao, Guang,Tang, Xihao,Zeng, Wei
, p. 5866 - 5875 (2014/08/05)
With the aid of an azo directing group, Pd-catalyzed ortho-sp2 C-H bond activation/functionalization of azoarenes with aryl acyl peroxides has been explored. This transformation provides easy access to regioselectively introducing acyloxyl and aryl groups into azoarenes by simply changing the reaction temperature and solvent. This journal is the Partner Organisations 2014.
