Cyclopropane
Cyclopropane
CAS: 75-19-4
Molecular Formula: C3H6
Cyclopropane - Names and Identifiers
| Name | Cyclopropane |
| Synonyms | TRIMETHYLENE Cyclopropane CYCLOPROPANE Cyclopropnane trimethylene(cyclic) Trimethylene (cyclic) cyclopropane,liquefied |
| CAS | 75-19-4 |
| EINECS | 200-847-8 |
Cyclopropane - Physico-chemical Properties
| Molecular Formula | C3H6 |
| Molar Mass | 42.08 |
| Density | 0.6190 |
| Melting Point | −128 °C(lit.) |
| Boling Point | −33 °C(lit.) |
| Refractive Index | 1.3799 |
Cyclopropane - Risk and Safety
| Hazard Symbols | F+ - Highly flammable |
| Risk Codes | 12 - Extremely Flammable |
| Safety Description | S9 - Keep container in a well-ventilated place. S16 - Keep away from sources of ignition. S33 - Take precautionary measures against static discharges. |
| UN IDs | UN 1027 2.1 |
Cyclopropane - Upstream Downstream Industry
Cyclopropane - Nature
| vapor density | 1.45 (vs air) |
| acidity coefficient (pKa) | 46(at 25℃) |
| explosion limit value (explosive limit) | 10.4% |
| water solubility | 464mg/L(25 °C) |
| Merck | 13,2777 |
| InChIKey | LVZWSLJZHVFIQJ-UHFFFAOYSA-N |
| EPA chemical information | Cyclopropane (75-19-4) |
Last Update：2024-04-10 22:29:15
Cyclopropane - Uses and synthesis methods
Naphthenic hydrocarbons
Cyclopropane is the first member of the same series of cycloalkanes. It contains 3 carbon atoms. Its chemical properties are more active than ordinary cycloalkanes. Its molecular formula is C3H6, molecular weight is 42.08, colorless and flammable gas, and has the smell of petroleum ether. Steam has 1.45 specific gravity, melting point -126.6 ℃, boiling point -33 ℃. The density under standard temperature and pressure is 1.879g/L. It can be liquefied at 192~588kPa(4~6 atmospheres). Slightly soluble in water, easily soluble in ethanol, ether and other organic solvents. It forms an explosive mixture with air. The explosion limit is 2.4% ~ 10.3% (volume), which is extremely easy to explode. Its combustion and explosiveness are more dangerous than toxicity. Its properties are unstable, it is easy to become an open-chain compound, and it is easy to be absorbed by concentrated sulfuric acid. It is easy to hydrogenate to obtain propane under the action of platinum catalyst, and reacts with bromine to open the chain to generate 1,3-dibromopropane, which is heated under platinum catalysis. At 50°C, it can be rearranged into propylene. Cyclopropane can be used in organic synthesis and as an anesthetic in medicine. Anesthesia concentration: 240~258g/m3 for rabbits, 172~206g/m3 for cats and 258~292g/m3 for dogs. When the concentration exceeds 430~516g/m3, animals can die due to respiratory paralysis. The MLC of dogs is 516g/m3. Cyclopropane also has properties similar to alkanes. If it is not oxidized by potassium permanganate (does not fade), it can be substituted with chlorine to generate chlorocyclopropane. Cyclopropane skeletons are widely found in various organic substances. For example, pyrethroid insecticides are generally carboxylates of cyclopropane. This product can be made by the interaction of 1, 3-dibromopropane or 1, 3-dichloropropane with sodium or zinc.
Cyclopropane is active in nature and is considered to be caused by its special carbocyclic structure. According to quantum mechanical calculations, the carbon ring bond angle is 105.5 °, and the carbon atoms in the molecule bend and overlap, shaped like a banana. Because the carbon and carbon are bent into bonds, not only the degree of overlap is less, but the electron layer is distributed on the outside of the straight line connecting the two carbon atoms, providing a position to be attacked by electrophiles, so reactions such as ring-opening addition are prone to occur.
aliphatic cyclic hydrocarbons
Aliphatic cyclic hydrocarbons are abbreviated as alicyclic hydrocarbons, which are closed-chain hydrocarbons with the properties of aliphatic compounds. It can be divided into saturated cycloalkanes and unsaturated cycloalkenes.
Naphthenes exist in petroleum and are components of petroleum products. Common naphthenic hydrocarbons include: cyclopropane, cyclobutane, cyclohexane, methylcyclohexane, naphthane, liquid fuels and solvents contained in cycloalkane, with a smaller molecular weight, while lubricants contain a larger molecular weight. In chemical production, they are also used as raw materials and solvents. Cycloolefins are by-products of petrochemical and coal coke chemicals and are used as chemical raw materials. The alicyclic hydrocarbons contained in plants are called terpenes (some terpenes are open-chain hydrocarbons). The mixture of terpenes commonly used in industry is turpentine. Most of these compounds are flammable liquids, and their vapor can reach explosive concentration in normal temperature air.
Alicyclic hydrocarbons are toxicologically similar to the corresponding open-chain hydrocarbons. Generally speaking, alicyclic hydrocarbons are anesthetics and central nervous system inhibitors. The inhalation anesthesia effect of cycloalkanes is stronger than that of the corresponding open-chain hydrocarbons. The anesthetic effect of cyclic olefins increases with the increase in the number of double bonds in the molecular structure. The acute toxicity of alicyclic hydrocarbons is low, almost all of them are discharged from the body, and there is generally no risk of chronic poisoning. Liquid alicyclic hydrocarbons are irritating to the skin. High concentrations of vapor can produce mucosal irritation. Cycloolefins are more irritating than cycloalkanes. Direct inhalation of liquid alicyclic hydrocarbons can cause pneumonia, pulmonary edema and pulmonary hemorrhage. No matter whether inhaled, orally or transdermal into the body, alicyclic hydrocarbons have not been found to have a damaging effect on hematopoietic tissues.
Preparation method
1. It is prepared by reducing 1, 2-dibromocyclopropane in absolute ethanol with zinc powder.
2. It is prepared by reducing 1, 3-dibromopropane in absolute ethanol with zinc powder.
3, using 1, 3-dibromopropane as raw material, interacting with sodium vapor, cyclopropane can be produced.
4, using 1, 3-dichloropropane as raw material, heating in the presence of excess zinc powder and absolute ethanol.
5, using 1, 3-dichloropropane as raw material, in the presence of sodium iodide, and reducing with zinc powder.
6. It is prepared by reacting ethylene with diiodomethane under the action of copper-zinc composite catalyst.
production method
Using 1, 3-dibromopropane and zinc powder as raw materials, the reaction is carried out in the presence of alcohol, and the reaction conditions are controlled to generate cyclopropane gas. The crude product was collected by low-temperature liquefaction and then purified by rectification.
category
Harmful gases
toxicity classification
low toxicity
acute toxicity
inhalation-mouse LCL0 282g/m3/2 h
explosive hazard characteristics
Explosive mixing with air
flammability hazard characteristics
Flammable
storage and transportation features
The warehouse is ventilated and dry at low temperature; stored separately from the oxidant
fire extinguishing agent
Carbon dioxide, foam, carbon tetrachloride
Last Update：2024-04-10 22:29:15
Cyclopropane - Security information
| WGK Germany | 1 |
| RTECS number | GZ0690000 |
| auto-ignition temperature | 928 °F |
| HazardClass | 2.1 |
| toxic substance data | 75-19-4(Hazardous Substances Data) |
| Toxicity | LCLo inhalation in mouse: 282gm/m3/2H |
Last Update：2024-04-10 22:29:15
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