3a,4,7,7a-Tetrahydro-4,7-methanoindene

3a,4,7,7a-Tetrahydro-4,7-methanoindene - Names and Identifiers

Name	Dicyclopentadiene
Synonyms	DCPD Dicyopentadiene Dicyclopentadiene Dicyclopentadiene dimer ALPHA-DICYCLOPENTADIENE 3a,4,7,7a-tetrahydro-7-methanoindene 3a,4,7,7a-Tetrahydro-4,7-methanoindene dicyclopentadiene (stabilized with bht) 3a,4,7,7a-tetrahydro-7-methano-1h-indene 4,7-Methanoindene, 3a,4,7,7a-tetrahydro- 3,4,7,7-Tetrahydro-4,7-methano-1H-indene 4,7-methano-3a,4,7,7a-tetrahydro-1H-indene 4,7-methano-1H-indene,3a,4,7,7a-tetrahydro- Cyclopentadiene dimer~3a,4,7,7a-Tetrahydro-4,7-methanoindene
CAS	77-73-6
EINECS	201-052-9
InChI	InChI=1/C10H12/c1-2-9-7-4-5-8(6-7)10(9)3-1/h1-2,4-5,7-10H,3,6H2
InChIKey	HECLRDQVFMWTQS-UHFFFAOYSA-N

3a,4,7,7a-Tetrahydro-4,7-methanoindene - Physico-chemical Properties

Molecular Formula	C10H12
Molar Mass	132.2
Density	0.986g/mLat 25°C(lit.)
Melting Point	33°C(lit.)
Boling Point	170°C(lit.)
Flash Point	114°F
Water Solubility	Immiscible with water.
Vapor Presure	3 hPa (20 °C)
Appearance	Liquid
Specific Gravity	0.968
Color	Clear
Odor	Camphor-like.
Exposure Limit	ACGIH: TWA 0.5 ppm; STEL 1 ppmNIOSH: TWA 5 ppm(30 mg/m3)
Merck	14,2739
BRN	1904092
Storage Condition	Store below +30°C.
Stability	Stable at room temperature, but may form explosive peroxides if stored in contact with air. Incompatible with oxidizing agents. Decomposes on heating. Flammable.
Sensitive	4: no reaction with water under neutral conditions
Explosive Limit	0.8-6.3%(V)
Refractive Index	n20/D 1.511
Physical and Chemical Properties	Characteristics of colorless crystals, similar to camphor odor. boiling point 170 ℃ (decomposition) freezing point 31.5 ℃ relative density 0.979 refractive index 1.5061 flash point 32.22 ℃ soluble in alcohol.
Use	Used in the manufacture of metal organic compounds, ferrocene, pesticides, monosodium glutamate and petroleum resins

3a,4,7,7a-Tetrahydro-4,7-methanoindene - Risk and Safety

Risk Codes	R11 - Highly Flammable R20/22 - Harmful by inhalation and if swallowed. R36/37/38 - Irritating to eyes, respiratory system and skin. R51/53 - Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R23 - Toxic by inhalation R22 - Harmful if swallowed R10 - Flammable
Safety Description	S36/37 - Wear suitable protective clothing and gloves. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
UN IDs	UN 2048 3/PG 3
WGK Germany	3
RTECS	PC1050000
TSCA	Yes
HS Code	29021990
Hazard Class	3
Packing Group	III
Toxicity	LD50 orally in Rabbit: 353 mg/kg LD50 dermal Rabbit 4940 mg/kg

3a,4,7,7a-Tetrahydro-4,7-methanoindene - Upstream Downstream Industry

Downstream Products

1-Adamantanamine hydrochloride
Carboprost methylate

3a,4,7,7a-Tetrahydro-4,7-methanoindene - Nature

Open Data Verified Data

colorless crystal, similar to camphor odor. The relative density was 0.979. Boiling point 170 degrees C (decomposition). The freezing point was 31.5 °c. Refractive index 5061. Flash point 32. 22 °c. Spontaneous ignition point 680. Soluble in alcohol. This product has a and beta two isomers, mouth isomer freezing point 33 ℃, isomer freezing point 19.5 ℃. Dicyclopentadiene is mainly contained in the isomer, boiling point of 170 deg C. Because this product contains double bonds, it is easy to carry out addition reaction and self polymerization reaction.

Last Update：2024-01-02 23:10:35

3a,4,7,7a-Tetrahydro-4,7-methanoindene - Preparation Method

Open Data Verified Data

The light benzene fraction of coal tar is distilled, and the benzene head fraction of <70 ° C., which contains about 30% of the cyclopentadiene, is then heated and polymerized to obtain the final dicyclopentadiene.
The C5 fraction in the hydrocarbon cracking industry is used as a raw material, which is obtained by heating dimerization and then performing vacuum distillation separation. Secondly, using cyclopentadiene as raw material, it can also be obtained by dimerization.

Last Update：2022-01-01 10:38:32

3a,4,7,7a-Tetrahydro-4,7-methanoindene - Use

Open Data Verified Data

This product is used as a raw material for synthetic rubber, pesticide, medicine, synthetic resin, paint and coating, etc., and is used as a high energy fuel after hydrogenation.

Last Update：2022-01-01 10:38:31

3a,4,7,7a-Tetrahydro-4,7-methanoindene - Safety

Open Data Verified Data

This product is toxic, with paralytic and local irritation, acute poisoning can cause Coma. The oral LD50 of rats was 820mg/kg body weight, and the skin absorption LD50 of rabbits was 6.72/kg body weight. The main pathological changes of oral poisoning in rats were extensive congestion and hemorrhage of lung, stomach, intestine, kidney and bladder. Devices and equipment containers should be sealed, and ventilation should be strengthened. The maximum allowable concentration in the air is 5 mg/m3. The operator should wear protective gear. Acute poisoning should be moved to the fresh air, according to the general anesthetic drug treatment.
This product is packaged in a small-mouth iron drum and stored in a cool and ventilated place. The materials shall be stored and transported according to the regulations on hazardous and flammable materials.

Last Update：2022-01-01 10:38:32

3a,4,7,7a-Tetrahydro-4,7-methanoindene - Reference Information

freezing point	31.5 ℃
NIST chemical information	information provided by: webbook.nist.gov (external link)
EPA chemical substance information	information provided by: ofmpeb.epa.gov (external link)
Introduction	Dicyclopentadiene (DCPC) is a dimer of cyclopentadiene. By first heating, cyclopentadiene is copolymerized into dicyclopentadiene, dicyclopentadiene is separated from other light components (boiling point <45 ℃) by distillation, and then other required Dienes are separated by solvent extraction, monoene and saturated hydrocarbon components. High purity dicyclopentadiene is colorless crystals at room temperature, containing impurities, light yellow oily liquid, irritating camphor flavor, insoluble in water, soluble in alcohol, ether and other organic solvents.
Application	DCPD can be converted to CPD at a certain temperature, thus greatly broadening the application of DCPD. From basic organic chemical raw materials to new metal polymer materials, DCPD has important uses, can be used as the production of unsaturated resin, metallocene, adamantane, glutaraldehyde, dicyclopentadiene chloride (insecticide) widely used in medicine, pesticides, spices, leather, synthetic rubber and other fields, in addition can also be used as high-energy fuel.
Use	raw material of polypentene rubber; Production of cyclopentanediol -1,2, cyclopentene oxide (such as dicyclopentadiene dicarboxylic acid, etc.); Stabilizer of organophosphorus bactericide; Synthetic chlorinated hydrocarbon insecticide; Raw material of pharmaceutical ketamine; Under heating, depolymerization is cyclopentadiene, styrene, acrylonitrile, isoprene and other compounds containing olefin bond Diels-Alders reaction, the product is the monomer of synthetic resin; Used as the third monomer of Ethylene Propylene Rubber, (I. E, has excellent electrical properties, heat resistance, weather resistance, drug resistance, widely used as automotive components); Synthetic Norbornene raw materials; Used as linseed oil, soybean oil, tung oil, fish oil modifier, improve its curing speed; Resin synthesized by this product, can be used as rubber adhesive, ink, coating; Production of polychlorocyclopentadiene pesticides (such as Aldrin, Di's agent, chlordane, heptachlor, etc.); also used as a fragrance (e. G. Tricyclodecyl acetate) Flame retardants (such as chlordane anhydride), polyester and other raw materials; The four hydride of this product is the high energy fuel of the rocket and jet engine. for the manufacture of metal organic compounds, ferrocene, pesticides, monosodium glutamate and petroleum resin, etc. cyclopentadiene dimer (or cyclopentadiene) the main uses are:(1) it is used as the third component of ethylene-propylene copolymer (EPDM);(2) it is used as a raw material for synthesizing ethylnorbornene (ENB);(3) it is reacted with maleic anhydride to obtain Norbornene dianhydride, used as raw materials of epoxy resin curing agent, polyester resin, alkyd resin, insecticide;(4) hexachlorocyclopentadiene, hexachloromethylene hydrogenated phthalic anhydride of hexachloromethylene, as a flame retardant for synthetic resin;(5) dicyclopentadiene for tung oil, linseed oil, soybean oil, fish oil, etc., can accelerate the drying, improve water resistance, alkali resistance;(6) dicyclopentadiene resin can be used as rubber adhesives, pressure-sensitive adhesives, hot-melt adhesives, inks, coatings, etc; (8) cyclopentene obtained by partial hydrogenation of cyclopentadiene, and then polymerized to obtain 1, 5-trans polycyclopentene;(9) cyclopentadiene is a raw material for the production of Aldrin, Diels class pesticides;(10) cyclopentadiene is also used in drug synthesis. For example, the intermediate α-cyclopentadienyl methyl mandelate of gastric Changle is obtained by the addition of methyl phenylacetonate and cyclopentadiene;(11) it is used as a high-energy fuel after hydrogenation. it can be used as the third monomer of ethylene-propylene rubber. For the synthesis of ethylene norbornene, also used as Ethylene Propylene Rubber third monomer. The reaction with maleic anhydride gives Norbornene dianhydride, which is used as an epoxy resin curing agent. Dicyclopentadiene on tung oil, linseed oil, soybean oil, fish oil modification, can accelerate the drying, improve water resistance, alkali resistance. Raw materials for the production of cyclopentadiene resins, paints and coatings. After hydrogenation, it is used as a high-energy fuel. It is mainly used in medicine, pesticide, synthetic resin, perfume, synthetic rubber and other fields. Can be used for the production of adamantane, 2-chloro-5-chloromethylpyridine, metallocene, glutaraldehyde, carbamate, epoxy resin curing agent, flame retardant, dicyclopentadiene chloride (insecticide) and so on. cyclopentadiene and dicyclopentadiene can be used for self-polymerization to produce various grades of petroleum resins. Copolymers of cyclopentadiene or dicyclopentadiene with various monomers are fully rubbers, resin inks, coatings, adhesives and sizing materials. dicyclopentadiene has active chemical properties and can be used as high energy fuel. Through a variety of chemical reactions, can produce metal derivatives, epoxy resins, polymers, norbornene compounds, adamantane, glutaraldehyde, perfume, pharmaceutical and Other Fine Chemicals for the preparation of sulfamethoxine, sulfamethoxazole and other sulfa drugs
preparation method	a method for preparing high-purity dicyclopentadiene, mainly including the following steps 1) A certain amount of crude dicyclopentadiene and diluent are added to the mixing tank, and the mass ratio of dicyclopentadiene to diluent is (1-4): 1. 2) The diluted dicyclopentadiene raw material obtained in step 1) is driven into the Depolymerization and rectification tower kettle by the metering pump; Under normal pressure, dicyclopentadiene depolymerization reaction takes place in the tower kettle to produce cyclopentadiene, the theoretical plate number of the Depolymerization and rectification column is 10~40, the column temperature is 160~200 ℃, the reflux ratio is 0.5~5, and the depolymerization time is 1~3H, the cyclopentadiene produced by depolymerization is purified by rectification in the Upper rectification column, and the high-purity cyclopentadiene product is obtained at the top of the column, and the kettle liquid of the column is continuously removed. 3) the cyclopentadiene obtained at the top of the column in step 2) is subjected to a one-tube reactor to dimerize cyclopentadiene to produce dicyclopentadiene at a reaction pressure of 0.1-1.5MPa and a reaction temperature of 40-120 ℃, the residence time was 4-10H.
production method	The light benzene fraction of coal tar was distilled, and the benzene head fraction of <70 ° C was cut, which contains about 30% cyclopentadiene, and then by heating, polymerization, distillation to obtain dicyclopentadiene. The C5 fraction in the hydrocarbon cracking industry is used as a raw material, which is obtained by heating dimerization and then performing vacuum distillation separation. Secondly, using cyclopentadiene as raw material, it can also be obtained by dimerization.
category	flammable liquid
toxicity grade	high toxicity
Acute toxicity	oral-rat LD50: 353 mg/kg; Oral-mouse LD50: 190 mg/kg
stimulation data	Skin-rabbits 10 mg/24 h severe; eye-rabbit 500 mg/24 h mild
explosive hazard characteristics	explosive when mixed with air
flammability hazard characteristics	flammable in case of open flame, high temperature and oxidant; combustion-induced smoke
storage and transportation characteristics	The warehouse is ventilated and dried at low temperature; It is stored separately from the oxidant; It is not suitable for long storage, to prevent aggregation
extinguishing agent	dry powder, dry sand, carbon dioxide, foam, 1211 extinguishing agent
Occupational Standard	TWA 30 mg/m3; Tel 54 mg/m3
spontaneous combustion temperature	503°C
toxic substance data	information provided by: pubchem.ncbi.nlm.nih.gov (external link)

Last Update：2024-04-09 20:02:46

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