Quick Search
DICYCLOPENTADIENE
CAS number: 77-73-6
EC number: 201-052-9
Chemical formula: C10H12
Molar mass: 132.20 g/mol
Dicyclopentadiene, abbreviated DCPD, is a chemical compound with formula C10H12.
At room temperature, Dicyclopentadiene is a clear light yellow color liquid with an acrid odor.
Dicyclopentadienes energy density is 10,975 Wh/l.
Dicyclopentadiene is coproduced in large quantities in the steam cracking of naphtha and gas oils to ethylene.
The major use of Dicyclopentadiene is in resins, particularly, unsaturated polyester resins.
Dicyclopentadiene is also used in inks, adhesives, and paints.
Chemical Formula for Dicyclopentadiene: C10H12
What is Dicyclopentadiene?
Dicyclopentadiene (DCPD) is produced as part of the separation process of crude C5 streams which is a by-product of ethylene manufacture.
Dicyclopentadiene is a colourless, waxy, flammable solid or liquid, with a camphor-like odour.
How is Dicyclopentadiene Used?
Chemicals derived from Dicyclopentadiene are used in many products, ranging from high quality optical lenses through to flame retardants for plastics and hot melt adhesives.
As a chemical intermediate, Dicyclopentadiene is used for making insecticides, hardener and dryer in linseed and soybean oil, and in the production of EPDM (ethylene propylene diene monomer) elastomers, metallocenes, resins, varnishes, and paints.
DCPD-containing products are also used in the production of hydrocarbon resins and unsaturated polyester resins.
Uses and Applications
Dicyclopentadiene is used in the production of commodity resins and polymers, such as hydrocarbon resins, unsaturated polyester resins and ethylene-propylene-diene rubbers.
Other uses for dicyclopentadiene are seen in the creation of specialty polymers and fine chemicals such as flame retardants, agrochemicals, specialty norbornenes, flavor and fragrance intermediates. Ashland uses dicyclopentadiene in multiple products.
Synthesis and structure
The spontaneous dimerization of cyclopentadiene at room temperature to form dicyclopentadiene proceeds to around 50% conversion over 24 hours and yields the endo isomer in better than 99:1 ratio as the kinetically favored product (about 150:1 endo:exo at 80 °C).
However, prolonged heating results in isomerization to the exo isomer.
The pure exo isomer was first prepared by base-mediated elimination of hydroiodo-exo-dicyclopentadiene.
Thermodynamically, the exo isomer is about 0.7 kcal/mol more stable than the endo isomer.
Dicyclopentadiene is a colorless liquid produced by heating crude oil (recovery of hydrocarbon streams from high temperature cracked petroleum fractions).
Dicyclopentadiene is a reactive intermediate used to produce a wide range of resins.
The majority of dicyclopentadiene interacts with the environment from releases during Dicyclopentadienes production, use, transport, or disposal.
Dicyclopentadiene is a low to moderate hazard material and the risk of adverse health effects associated with both occupational and consumer use of this chemical is anticipated to be low.
Exposure controls in the workplace serve to prevent adverse health effects to workers.
Consumers are unlikely to come into contact with harmful levels of dicyclopentadiene, as Dicyclopentadiene is found only in trace quantities in consumer products.
Chemical Properties
Cyclopentadiene is a crystalline solid or a liquid (above 32°C) with a disagreeable, camphor-like odor.
The Odor Threshold is 0.011 (detectable); 0.020 ppm (recognizable).
cyclopentadiene, although a stable molecule, has a strong tendency to form the more stable dimer dicyclopentadiene.
This dimerisation already takes place at room temperature and its rate rapidly increases with elevated temperatures.
This reaction however is reversible too; dicyclopentadiene "cracks" at temperatures above 140°C to form two cyclopentadiene molecules.
The physical properties of pure cyclopentadiene and dicyclopentadiene are given below as well as some product specific characteristics and compositions.
Uses
Dicyclopentadiene is used in the synthesis of chlorinated hydrocarbon pesticides and ferrocene; in paint, varnish, and resin manufacture; in elastomers used as water pond liners, and as a repellent for animals such as hares, rabbits, and deer, in winter or in summer.
Dicyclopentadiene is applied in the form of impregnated strip on deciduous and coniferous trees, or by spraying around ornamental plants and shrubs.
Dicyclopentadiene or DCPD is the dimer of cyclopentadiene (CPD) formed by a DielsAlder addition reaction.
DCPD products originate from high temperature cracking of petroleum fractions and are best characterized as highly reactive intermediates used for a wide range of resins, i. e. aromatic hydrocarbons, unsaturated polyesters, phenolics and epoxies.
Dicyclopentadiene RESIN GRADE - Dicyclopentadiene is most used in aromatic hydrocarbon and unsaturated polyester resins.
Dicyclopentadiene, UPR Grade- Developed for use in unsaturated polyester resins.
Dicyclopentadiene HIGH PURITY- Suited for water-white resins and specialty applications.
As a chemical intermediate in the manufacture of pesticides; in the production of resin coatings, adhesives, and fuel additives
Appearance: Colorless, crystalline solid
Odor: disagreeable, camphor-like
Density: 0.978 g/cm3
Melting point: 32.5 °C (90.5 °F; 305.6 K)
Boiling point: 170 °C (338 °F; 443 K)
Solubility in water: 0.02%
Solubility: very soluble in ethyl ether, ethanol
soluble in acetone, dichloromethane, ethyl acetate, n-hexane, toluene
log P: 2.78
Vapor pressure: 180 Pa (20 °C)
Decomposes at: 170-172°C
Melting point: 32-34°C
Density: 0.98 g/cm³
Solubility in water, g/100ml at 25°C: 0.002
Flash point: 32°C o.c.
Auto-ignition temperature: 503°C
Explosive limits, vol% in air: 0.8-6.3
Octanol/water partition coefficient as log Pow: 2.78
Dicyclopentadiene (DCPD) is the dimer of cyclopentadiene that is produced through the Diels-Alder Reaction.
Dicyclopentadiene is a colorless, flammable substance with a camphor-like odor.
The growing consumption of batteries and increasing use of dicyclopentadiene as industrial catalysts and solvents have been driving the market growth.
Production Methods
Dicyclopentadiene is produced by recovery from hydrocarbon streams from high temperature cracked petroleum fractions.
Dicyclopentadiene is also a by-product of the coke oven industry.
Cyclopentadiene polymerizes to dicyclopentadiene on standing.
Dicyclopentadiene is produced by thermal cracking of petrochemical feedstocks or as a by-product of the coke oven industry.
Dicyclopentadiene is also formed by spontaneous dimerization of cyclopentadiene.
General Description
A liquid with an acrid odor. Flash point 90°F.
The vapors are irritating to the eyes and respiratory system.
Subject to polymerization if subjected to heat for prolonged periods or if contaminated.
If the polymerization takes place inside a container, the container may violently rupture.
Insoluble in water.
Density 8.2 lb / gal.
Dicyclopentadiene is used in paints, varnishes, as an intermediate in insecticides, as a flame retardant in plastics.
Reactivity Profile
Dicyclopentadiene may react vigorously with oxidizing agents.
May react exothermically with reducing agents to release hydrogen gas.
Can undergo exothermic polymierization reactions In the presence of various catalysts (such as acids) or initiators, if subjected to heat for prolonged periods, or if contaminated.
Many undergo autoxidation upon exposure to the air to form explosive peroxides.
Dicyclopentadiene Reactions
Above 150 °C, dicyclopentadiene undergoes a retro-Diels–Alder reaction at an appreciable rate to yield cyclopentadiene.
The reaction is reversible and at room temperature cyclopentadiene dimerizes over the course of hours to re-form dicyclopentadiene.
Cyclopentadiene is a useful diene in Diels–Alder reactions as well as a precursor to metallocenes in organometallic chemistry.
Dicyclopentadiene is not available commercially as the monomer, due to the rapid formation of dicyclopentadiene; hence, Dicyclopentadiene must be prepared by "cracking" the dicyclopentadiene (heating the dimer and isolating the monomer by distillation) shortly before Dicyclopentadiene is needed.
The thermodynamic parameters of this process have been measured.
At temperatures above about 125 °C in the vapor phase, dissociation to cyclopentadiene monomer starts to become thermodynamically favored (the dissociation constant Kd = [cyclopentadiene]2 / [dicyclopentadiene] > 1).
For instance, the values of Kd at 149 °C and 195 °C were found to be 277 and 2200, respectively.
By extrapolation, Kd is on the order of 10–4 at 25 °C, and dissociation is disfavored.
In accord with the negative values of ΔH° and ΔS° for the Diels–Alder reaction, dissociation of dicyclopentadiene is more thermodynamically favorable at high temperatures.
Equilibrium constant measurements imply that ΔH° = –18 kcal/mol and ΔS° = –40 eu for cyclopentadiene dimerization.
Hydrogenation of dicyclopentadiene gives endo-tetrahydridodicyclopentadiene (TH-dimer), a fuel in military applications.
On reaction with aluminium chloride at elevated temperature, this C10 hydrocarbon rearranges to adamantane.
Dicyclopentadiene polymerizes.
Copolymers are formed with ethylene or styrene.
The "norbornene double bond" participates.
Using ring-opening metathesis polymerization a homopolymer polydicyclopentadiene is formed.
Hydroformylation of DCP gives the dialdehyde called TCD dialdehyde (TCD = tricyclodecane).
This dialdehyde can be oxidized to the dicarboxylic acid and to a diol.
All of these derivatives have some use in polymer science.
Hydrogenation of dicyclopentadiene gives the saturated derivative C10H16, which undergoes acid-catalyzed rearrangement to adamantane.
Dicyclopentadiene, abbreviated DCPD, is the dimer of cyclopentadiene (CPD).
In the pure state DCPD is a volatile solid with a characteristic odour.
Dicyclopentadiene is coproduced in large quantities in the steam cracking of naphtha and gas oils to ethylene.
In addition, Dicyclopentadiene can be prepared in a Diels-Alderreaction of 2 cyclopentadiene molecules.
Most dicyclopentadiene is used as co-monomer in the production of synthetic resins, in particular unsaturated polyesters and synthetic rubbers, for example EPDM. Poly (DCPD), which contains some dicyclopentadiene as monomer is used in printing inks and engineering plastics.
Dicyclopentadiene, abbreviated DCPD, is a chemical compound with formula C10H12.
At room temperature, Dicyclopentadiene is a white crystalline solid with a camphor-like odor.
Dicyclopentadienes energy density is 10,975 Wh/l.
Dicyclopentadiene is coproduced in large quantities in the steam cracking of naphtha and gas oils to ethylene.
The major use is in resins, particularly, unsaturated polyester resins.
Dicyclopentadiene is also used in inks, adhesives, and paints.
CPD, although a stable molecule, has a strong tendency to form the more stable dimer DCPD.
This dimerization already takes place at room temperature and its rate rapidly increases with elevated temperatures.
This reaction however is reversible too; DCPD “cracks” at temperatures above 140°C to form two CPD molecules.
The physical properties of pure CPD and DCPD are given below as well as some product specific characteristics and compositions.
Dicyclopentadiene (DCPD) modified unsaturated polyester resins (UPRs) are mostly used for hulls, decks, and bathroom facilities.
Main advantages of these polymers over orthophthalic or isophthalic polyesters are their relatively low shrinking, reduced styrene emission, lower cost, and fast curing in thin layers.
On the other hand, once cured, these materials are more brittle and have lower glass transition temperatures and lower chemical resistance due to their different chemical constitutions.
DCPD UPRs with standard grades are usually produced with high-quality DCPD (over a 85% purity) using the so-called “water process”, a synthesis consisting of two reaction steps.
An adduct of maleic anhydride with DCPD is firstly formed with water, and then, Dicyclopentadiene reacts with the other esterification monomers such as acids and glycols.
DCPD raw materials used in this study were prepared by a unique distillation process developed by ORLEN Unipetrol and
University of Chemistry and Technology, Prague.
This technology allows producing a wide spectrum of DCPD quality by adjusting the content of another norbornene dimer: methyl dicyclopentadiene (MeDCPD).
Dicyclopentadiene or DCPD is the dimer of cyclopentadiene (CPD) formed by a Diels-Alder addition reaction.
DCPD products originate from high-temperature cracking of petroleum fractions and are best characterized as highly reactive intermediates used for a wide range of resins, i. e. aromatic hydrocarbons, unsaturated polyesters, phenolics and epoxies.
Characteristics, properties, manufacture and applications of dicyclopentadiene (DCPD) are discussed and summarized.
The manufacturers and end users are mentioned. Dicyclopentadiene is a cyclopentadiene (CPD) dimer; Dicyclopentadiene is recovered from the C5 fraction produced together with ethene by steam cracking of naphthas, gas oils and heavy hydrocracking residues.
Two general categories of industrial use of CPD and DCPD are: production of resins and polymers including hydrocarbon resins, unsaturated polyester resins and production of fine chemicals such as norbornene and ethylidenenorbornene and special polymers including cyclic olefin copolymers and poly(dicyclopentadiene).
Some flame retardants, agrochemicals, norbornenes, flavor and fragrance intermediates are also based on cyclopentadiene.
High-purity DCPD (93–95 wt.%) is cracked to give CPD and intermediates such as ENB.
ENB and high-purity DCPD are used in the production of ethene-propene-diene rubbers (EPDM).
High-purity DCPD can be further upgraded to an ultrapure grade (over 98 wt.% DCPD).
Polymerization of ultrapure DCPD leads to poly(DCPD), which is used in catalytic reactive injection molding (RIM).
Dicyclopentadiene can be analyzed by this reverse phase (RP) HPLC method with simple conditions.
The mobile phase contains an acetonitrile (MeCN), water, and phosphoric acid.
For Mass-Spec (MS) compatible applications the phosphoric acid needs to be replaced with formic acid.
Smaller 3 µm particles columns available for fast UPLC applications.
This liquid chromatography method is scalable and can be used for isolation impurities in preparative separation.
Dicyclopentadiene also suitable for pharmacokinetics.
CAS Number: 77-73-6
Molecular Formula: C₁₀H₁₂
Appearance: Clear Colorless Low-Melting Solid
Melting Point: N/A
Storage Room Temperature
Solubility: Chloroform (Slightly), Methanol (Slightly)
Category: Building Blocks; Miscellaneous;
Applications: Dicyclopentadiene is used in the preparation of poly(ionic liquid) brushes, used in anti-bacterial and anti-biofouling applications.
Also used in the preparation of copolymer structures in the synthesis of nanocapsules.
Dicyclopentadiene is coproduced in large quantities in the steam cracking of naphtha and gas oils to ethylene.
The major use is resins, particularly unsaturated polyester resins.
Dicyclopentadiene is also used in inks, adhesives, and paints.
Dicyclopentadiene is co-produced with ethylene from the C5 fraction in the steam cracking of naphtha and gas oils.
The largest consumption of
dicyclopentadiene is linked to the production of resins including unsaturated polyester resins, petroleum resins, terpolymers, polynorbornenes, and other cyclic olefin polymers.
Dicyclopentadiene is used to manufacture pesticides, paints, varnishes, metal derivative, epoxy resin, adamantane, glutaraldehyde, perfumery, flame retardants, medicine, other chemicals.
Exposure:
People may be exposed to DCPD in the workplace where Dicyclopentadiene is a part of an industrial process or when the chemical is released into the environment.
Drinking/Eating: People may be exposed by drinking contaminated water, although DCPD’s strong odor in water would discourage people from drinking Dicyclopentadiene.
People who handle contaminated soil may be exposed when they eat, or when they touch their mouths with dirty hands.
Touching: People may be exposed if they handle the chemical, or contaminated soil or water.
Although the chemical may irritate the skin, Dicyclopentadiene does not easily pass through the skin.
Breathing: If DCPD is in the air, people may breathe Dicyclopentadiene in.
If DCPD is in water, Dicyclopentadiene can pass into the air and people could inhale the chemical while washing, bathing or cooking.
Synomys:
77-73-6
Cyclopentadiene dimer
Bicyclopentadiene
Biscyclopentadiene
Dicyklopentadien
Dimer cyklopentadienu
4,7-Methano-1H-indene, 3a,4,7,7a-tetrahydro-
DCPD
3a,4,7,7a-Tetrahydro-4,7-methanoindene
3a,4,7,7a-tetrahydro-1H-4,7-methanoindene
NSC 7352
4,7-Methanoindene, 3a,4,7,7a-tetrahydro-
endo-Dicyclopentadiene
1,3-Cyclopentadiene, dimer
4,7-Methano-3a,4,7,7a-tetrahydroindene
CHEBI:34695
NCGC00090776-02
Tricyclo[5.2.1.0(2,6)]deca-3,8-diene
EXO-DICYCLOPENTADIENE
1755-01-7
Dicyklopentadien [Czech]
Dimer cyklopentadienu [Czech]
CCRIS 4790
HSDB 321
Prometa XP 100
1,3-CPD
3a,4,7,7a-Tetrahydro-4,7-methano-1H-indene
933-60-8
alpha-Dicyclopentadiene (endo form)
EINECS 201-052-9
UN2048
Tricyclo(5.2.1.0)-3,8-decadiene
Dicyclopentadiene homopolymer
BRN 1904092
AI3-03386
Dicyclopentadiene, 95%, stabilized with 100-200 ppm 4-tert-Butylcatechol
4,7-Methano-1H-indene, 3a,4,7,7a-tetrahydro-, homopolymer
UN 2048
1, dimer
25038-78-2
Tricyclo[5.2.1.0<2,6>]deca-3,8-diene
ACMC-20p1dy
DSSTox_CID_5023
EC 201-052-9
DSSTox_RID_77632
DSSTox_GSID_25023
2-05-00-00391 (Beilstein Handbook Reference)
MLS001055376
CHEMBL1570502
DTXSID5025023
NSC7352
bicyclopentadiene
biscyclopentadiene
1,3-CPD
cyclopentadiene dimer
1,3-cyclopentadiene, dimer
DCPD
alpha-dicyclopentadiene (endo form)
dicyclopentadiene [UN2048] [Flammable liquid]
dicyklopentadien
4,7-methano-1H-indene, 3a,4,7,7a-tetrahydro-
4,7-methanoindene, 3a,4,7,7a-tetrahydro-
prometa XP 100
3a,4,7,7a-tetrahydro-4,7-methanoindene
tricyclo(5.2.1.0)-3,8-decadiene
HMS3039J06
WLN: L C555 A DU IUTJ
NSC-7352
Tox21_400017
MFCD00082365
STL445669
AKOS000119974
AKOS022186108
EBD2156423
MCULE-9069962871
3a,7,7a-Tetrahydro-4,7-methanoindene
4,7-Methano-1H-indene, 3a,4,7,7a-tetrahydro-, (3a.alpha.,4.alpha.,7.alpha.,7a.alpha.)-
CAS-77-73-6
NCGC00090776-01
NCGC00090776-03
AC-16096
SMR000677942
Tricyclo[5.2.1.02,6]deca-3,8-diene
Dicyclopentadiene contains BHT as stabilizer
D0443
C14411Dicyclopentadiene [UN2048]
Q419053
J-520256
Q-200967
F0001-1975
(3a.alpha.,4.alpha.,7.alpha.,7a.alpha.)-3a,4,7,7a-Tetrahydro-4,7-methano-1H-indene
1,3-Cyclopentadiene, dimer
247-724-5 [EINECS]
26472-00-4 [RN]
3a,4,7,7a-tetrahydro-1H-4,7-methanoindene
4,7-Methano-1H-indene, 3a,4,7,7a-tetrahydro- [ACD/Index Name]
Bicyclopentadiene
Biscyclopentadiene
Dicyclopentadiene [Wiki]
Dicyclopentadiene [UN2048] [Flammable liquid]
Tricyclo[5.2.1.02,6]deca-3,8-dien [German] [ACD/IUPAC Name]
Tricyclo[5.2.1.02,6]deca-3,8-diene [ACD/IUPAC Name]
Tricyclo[5.2.1.02,6]déca-3,8-diène [French] [ACD/IUPAC Name]
(3aα,4α,7α,7aα)-3a,4,7,7a-tetrahydro-4,7-methano-1H-indene
(3aα,4α,7α,7aα)-3a,4,7,7a-Tetrahydro-4,7-methano-1H-indene
1,3-CPD
3a,4,7,7a-Tetrahydro-1H-4,7-methano-indene
3a,4,7,7a-Tetrahydro-4,7-methano-1H-indene
3a,4,7,7a-Tetrahydro-4,7-methanoindene
4,7-Methano-3a,4,7,7a-tetrahydroindene
4,7-Methanoindene, 3a,4,7,7a-tetrahydro-
538-75-0 [RN]
Bis[cyclopentadiene]
cyclopenta-1,3-diene; cyclopentane
Cyclopentadiene dimer
Dicyclopentadiene (stabilised)
Dicyklopentadien
Dimer cyklopentadienu
MFCD00078246 [MDL number]
Tricyclo(5.2.1.0)-3,8-decadiene
Tricyclo[5.2.1.0(2,6)]deca-3,8-diene
tricyclo[5.2.1.0<2,6>]deca-3,8-diene
tricyclo[5.2.1.02,6]deca-3,8-diene
UN 2048
WLN: L C555 A DU IUTJ
