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Isobutylene
POLYISOBUTENE · usb · p20 · p118 · p200 · oppanolb100 · PIB=Oppanol(R) · POLY(ISOBUTYLENE) 24'000
Identifikatoren & physikalische Daten
| CAS No. | 9003-27-4 |
|---|---|
| Summenformel | C4H8 |
| Durchschnittliche Molmasse | 56,11 g/mol |
| SMILES | C=C(C)C |
| InChIKey | VQTUBCCKSQIDNK-UHFFFAOYSA-N |
| ChEBI | CHEBI:43907 |
| EC No. | 204-066-3 |
Chemische & physikalische Eigenschaften
| XLogP | 2,1 |
|---|---|
| Polarare Oberfläche (TPSA) | 0 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 0 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 4 |
| Formalladung | 0 |
| Komplexität | 23 |
| Stoffklassen | Other Classes -> Aliphatics, UnsaturatedFlammable agents - 4th degree |
| SpringerMaterials Properties | Coriolis coupling |
| LogP (Verteilungskoeffizient) | log Kow = 2.342.35 |
| Geruch | Coal gas odor |
| Dichte | 0.59 at 68 °F (USCG, 1999) - Less dense than waterwill float0.589 g/cu cm at 25 °C (p >1 atm)Density: 0.6 at 20 °CRelative density (water = 1): 0.590.6 @25 °C0.92 g/mL at 25 °C (lit.) |
| Color/Form | Colorless gasColorless volatile liquid or easily liquefied gas |
| Löslichkeit | Insoluble (NTP, 1992)In water, 263 mg/L at 25 °CVery soluble in ethanol and ethersoluble in benzene, sulfuric acidSoluble in organic solventsSolubility in water, g/100ml at 20 °C: 0.03 |
| Flammpunkt | -105 °F (NTP, 1992)-76 °C-80 °C (-112 °F) - closed cup-105 °F (-76 °C)-76.1 °C c.c.>212 |
| Siedepunkt | 19.6 °F at 760 mmHg (NTP, 1992)-7.0 °C-6.9 °C-6.9 °C @760 [mm Hg]300 °C |
| Decomposition | Hazardous decomposition products formed under fire conditions: Carbon oxidesWhen heated to decomposition it emits acrid smoke and fumes. |
| Schmelzpunkt | -220.5 °F (NTP, 1992)-140.7 °C-140.3 °C54-56 °C |
| Dampfdichte | 1.9 (NTP, 1992) - Heavier than airwill sink (Relative to Air)1.94 (Air = 1)Relative vapor density (air = 1): 1.94 |
| Tg | -61 |
| Brechungsindex | n20/D 1.51 |
| Aggregatzustand | slab/chunk |
| Farbe | colorlessor white |
| Stabilität | Stability Combustible. Incompatible with strong oxidizing agents. |
| Kosmetik-Inhaltsstoffe Funktionen | VISCOSITY CONTROLLINGBINDINGFILM FORMING |
| InChI | InChI=1S/C4H8/c1-4(2)3/h1H2,2-3H3 |
| InChIKey | VQTUBCCKSQIDNK-UHFFFAOYSA-N |
| SMILES | C=C(C)C |
| Oberflächenspannung | 33.6mN/m at 20°C |
| EPA chemische Informationen | Polyisobutylene (9003-27-4) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH220: Extremely flammable gas [Danger Flammable gases]P203, P210, P222, P280, P377, P381, and P403 (click each P-code to see the statement)This chemical does not meet GHS hazard criteria for < 0.1% (1 of 1424) of reports.H220 (99.9%): Extremely flammable gas [Danger Flammable gases] |
|---|---|
| Regulatorische Informationen | Chemical: 1-Propene, 2-methyl-1-Propene, 2-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1-Propene, 2-methyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 15-05-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/161061-Propene, 2-methyl- (isobutene): HSNO Approval: HSR001004 Approved with controlsThe New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.) |
| Weitere Sicherheitsinformationen | IMAP assessments - 1-Propene, 2-methyl-: Human health tier I assessment |
| DOT-Kennzeichnung | Flammable Gas |
| Brandgefahren | Behavior in Fire: Containers may explode in fire. Vapor is heavier than air and may travel a long distance to a source of ignition and flash back. (USCG, 1999)· EXTREMELY FLAMMABLE.Extremely flammable. Gas/air mixtures are explosive. Risk of fire and explosion on contact with oxidizing agents or halogens. See Chemical Dangers. |
| Brandpotenzial | A very dangerous fire and explosion hazard when exposed to heat or flame.Highly flammable, dangerous fire, and explosion risk. |
| Gesundheitsgefahren | Inhalation of moderate concentrations causes dizziness, drowsiness, and unconsciousness. Contact with eyes or skin may cause irritationthe liquid may cause frostbite. (USCG, 1999)· Vapors may cause dizziness or asphyxiation without warning, especially when in closed or confined areas. |
| Gefahrenübersicht | In confined space spill, may displace air and act as simple asphyxiantEvaporating liquid can cause frostbiteInhalation of high concentrations can cause CNS depression[ICSC] May cause irritationInhalation of high concentrations can cause CNS depression and anesthesia[MSDSonline] See Butene, all isomers. |
| DOT-Nummer und Handbuch | 1055 1151075 115 |
| FDA-Anforderungen | Isobutylene is an indirect food additive for use only as a component of adhesives. |
| Reaktive Gruppe | Hydrocarbons, Aliphatic Unsaturated |
| EG-Einstufung | Symbol: F+R: 12S: (2)-9-16-33Note: C |
| UN-Einstufung | UN Hazard Class: 2.1 |
| Brandbekämpfung | Excerpt from ERG Guide 115 [Gases - Flammable (Including Refrigerated Liquids)]:Shut off supplyif not possible and no risk to surroundings, let the fire burn itself out. In other cases extinguish with water spray, powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water. Combat fire from a sheltered position. |
| Erste-Hilfe-Maßnahmen | Fresh air, rest. Artificial respiration may be needed. Refer for medical attention.ON FROSTBITE: rinse with plenty of water, do NOT remove clothes. Refer for medical attention .First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention. |
| Freisetungsmaßnahmen | · CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. |
| Erste Hilfe | EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.General First Aid: |
| Sichere Lagerung | Fireproof. Separated from incompatible materials. See Chemical Dangers. Cool. |
| Expositionsschutz und Persönliche Schutzausrüstung | · Wear positive pressure self-contained breathing apparatus (SCBA). |
| Brandbekämpfungsverfahren | Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.Use water spray to cool unopened containers.To fight fire, stop flow of gas. |
| Lagerbedingungen | Keep container tightly closed in a dry and well-ventilated place. |
| Reinigungsverfahren | ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low areas. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Methods and materials for containment and cleaning up: Clean up promptly by sweeping or vacuum. |
| Freisetung ohne Brand | Excerpt from ERG Guide 115 [Gases - Flammable (Including Refrigerated Liquids)]: |
| Entsorgungsverfahren | SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air qualitypotential migration in air, soil or watereffects on animal, aquatic and plant lifeand conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.Product: Burn in a chemical incinerator equipped with an afterburner and scrubber but exert extra care in igniting as this material is highly flammable. Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Contaminated packaging: Dispose of as unused product. |
| Verschüttetes entsorgen | Evacuate danger area! Consult an expert! Ventilation. Remove all ignition sources. Do NOT wash away into sewer. NEVER direct water jet on liquid. Personal protection: chemical protection suit including self-contained breathing apparatus. |
| Wechselwirkungen | Gas-liquid chromatography was used to study brain hydrocarbon content in rats and mice inhaling mixtures of butane and isobutylene. There was summation of CNS depressant effects of butane and isobutylene toward potentiation rather than antagonism. |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 32(SRC), determined from a structure estimation method(2), indicates that isobutylene is expected to have very high mobility in soil(SRC). Volatilization of isobutylene from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 0.218 atm-cu m/mole(3). Isobutylene is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 2,308 mm Hg at 25 °C(4). Isobutylene was degraded to 1,2-epoxy butane by pure cultures of methanotrophic bacteria(5), suggesting biodegradation may occur at intefaces between aerobic and anaerobic conditions in soil(SRC).FIELD STUDY: Isobutylene was detected at 165 and 125 ppbv in 2 gas recovery wells at the Case Passerini landfill site in Florence, Italy. The concentration was <10 ppbv in cover soil samples at depths of 0, 30, 50 and 70 cm. Sampling was conducted during the summer dry season in July(1).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 32(SRC), determined from a structure estimation method(2), indicates that isobutylene is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 0.218 atm-cu m/mole(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 2 and 71 hours, respectively(SRC). According to a classification scheme(5), an estimated BCF of 16(SRC), from its log Kow of 2.34(6) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Isobutylene was degraded to 1,2-epoxy butane by pure cultures of methanotrophic bacteria(7), suggesting biodegradation may occur at intefaces between aerobic and anaerobic conditions in water(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), isobutylene, which has a vapor pressure of 2,308 mm Hg at 25 °C(2), is expected to exist solely as a gas in the ambient atmosphere. Gas-phase isobutylene is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC)the half-life for this reaction in air is estimated to be 7.5 hours(SRC), calculated from its rate constant of 5.14X10-11 cu cm/molecule-sec at 25 °C(3). The rate constant for the gas-phase reaction of isobutylene with ozone has been measured as 1.2X10-17 cu cm/molecule-sec at 25 °C(4). This corresponds to an atmospheric half-life of about 23 hours at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(4). Isobutylene does not absorb UV light at wavelengths >290 nm(5) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC). |
| Unerwünschte Wirkungen | Neurotoxin - Acute solvent syndrome |
| Expositionspfade | The substance can be absorbed into the body by inhalation. |
| Toxizitätsübersicht | IDENTIFICATION AND USE: Isobutylene is an easily liquefied gas. It is used to produce diisobutylene, trimers, butyl rubber, and other polymers. It is also used to produce antioxidants for foods, packaging, food supplements, and for plastics. HUMAN STUDIES: Isobutene causes CNS depression at higher concentrations. There is a linear relationship between the degree of CNS depression and the cerebral concentrations. Isobutylene was not mutagenic when tested in the in vitro micronucleus test using human lymphocytes. ANIMAL STUDIES: Isobutene, at 30%, produces no CNS depression in mice, and excitement and CNS depression in 7 to 8 min at 40%, but immediate CNS depression in 2-2.25 min at 50%, or in 50-60 sec at 60 to 70%. Exposure to isobutene by inhalation for 2 years resulted in increased incidences and/or severities of nasal lesions including hyaline degeneration of the olfactory epithelium in mice and hyaline degeneration of the respiratory epithelium in male and female mice. There was no evidence of carcinogenic activity of isobutylene in male or female mice exposed to 500, 2,000, or 8,000 ppm 6 hours per day, 5 days per week, for 105 weeks. There was some evidence of carcinogenic activity of isobutene in male rats based on an increased incidence of follicular cell carcinoma of the thyroid gland. It was negative when tested for mutagenicity in Escherichia coli, the Ames Salmonella typhimurium assay, and a modified Salmonella assay, with and without metabolic activation. No increase in the frequency of micronucleated erythrocytes was seen in peripheral blood of male or female mice treated with isobutylene by inhalation for 14 weeks. |
| Signs and Symptoms | Dizziness. Drowsiness. Lethargy. Nausea. Unconsciousness. Vomiting.ON CONTACT WITH LIQUID: FROSTBITE.See Skin. |
| Ongoing Test Status | The following link will take the user to the National Toxicology Program (NTP) Test Status of Agents Search page, which tabulates the results and current status of tests such as "Short-Term Toxicity Studies", "Long-term Carcinogenicity Studies", "Developmental Studies", "Genetic Toxicology Studies", etc., performed with this chemical. Testing status for isobutylene is available.[Available from, as of November 3, 2017: https://ntpsearch.niehs.nih.gov/?e=True&ContentType=Testing+Status] |
| Effluent Concentrations | Isobutylene was identified, not quantified, in the effluent of a plastic incineration plant in Japan(1). |
| Soil Adsorption/Mobility | Using a structure estimation method based on molecular connectivity indices(1), the Koc of isobutylene can be estimated to be 32(SRC). According to a classification scheme(2), this estimated Koc value suggests that isobutylene is expected to have very high mobility in soil(SRC). |
| Natural Pollution Sources | Isobutylene is a component of petroleum and natural gas. |
| Atmospheric Concentrations | URBAN/SUBURBAN: Isobutylene was detected in Los Angeles, CA at a concentration of 2.35 ug/cu m(1). Combined isomers of isobutylene and 1-butene were detected in Washington DC at a mean concentration of 0.67 ppb and a maximum concentration of 2.25 ppb in 1991(2). Isobutylene was identified, not quantified, in Chicago, IL, Raleigh, NC, Atlanta, GA and Budapest, Hungary(3). Combined isomers of isobutylene and 1-butene were detected in urban areas around Vienna, Austria at mean concentrations of 9.6 and 10.1 ppb at 2 different sampling locations(4). Isobutylene was detected at street levels in London, England at a mean concentration of 19 ppb(5). Isobutylene was detected in the atmosphere of London, England at concentrations of 132-1,506 parts per trillion at altitudes between 453 and 758 m(5). Isobutylene was detected at a mean concentration of 8.8 ppbC in urban air samples from a car park in Lancaster, England sampled June-July 1983(6). Butenes, including isobutylene, were detected at the following locations in Sweden: outdoor park (0.09 ug/cu m), city streets (0.7-7.7 ug/cu m) and a parking garage (7.7 ug/cu m)(7). Isobutylene was detected in Porto Alegre, Brazil at concentration range of 1-15 ug/cu m(8). The average concentration of isobutylene was 2.7 ppbv (range of 0.4-9.3in the atmosphere of Taipei metropolitan area, Taiwan, a region characterized by high passenger car and motor bike traffic and few major industrial sites(9).SOURCE DOMINATED: Isobutylene has been identified, not quantified, in the exhaust of automobiles(1-3). Isobutylene was detected at a concentration of 60 and 28 ug/cu m in the emissions of automobiles(4). Isobutylene was detected at concentrations of 0.14 ppb (87 octane) and 0.13 ppb (89 octane) in automobile exhaust(5).SOURCE DOMINATED: Isobutylene was detected in the Caldecott Tunnel, CA at a concentration of 0.058 g/L of August 1994 when vehicles were using low oxygenated gasoline and 0.089 g/l in October 1994 when vehicles were using high oxygenated gasoline(1). Combined isomers of isobutylene and 1-butene were detected in the Lincoln Tunnel, NY at a mean concentration of 344.9 ppb in 1970 and 89.1 ppb in 1982(2). Isobutylene concentrations of <5 mg HC/km were determined in the exhaust emissions from gasoline- and LPG-powered catalyst-equipped vehicles operating at the altitude of Mexico City in 1996(3). An average concentration of 758.8 ug/cu m (6 samples) was reported in the air at an ethanol and gasoline service station with 5 pumps in the Flamengo District, Rio de Janiero, Brazil, sampled on June 9, 2004(4).SOURCE DOMINATED: Isobutylene sources to the atmosphere in Cairo, Egypt, June 1997(1).[Table#1717]RURAL/REMOTE: Isobutylene was detected at a mean concentration of <0.5 ppbC in rural air samples and at 1.0 ppb in polluted rural air in northwest, Englandsampling was conducted during May-June, 1983(1). |
| Human Toxicity Excerpts | /SIGNS AND SYMPTOMS/ Isobutene ... causes CNS depression at higher concentrations. There is a linear relationship between the degree of CNS depression and the cerebral concentrations./GENOTOXICITY/ 2-Methylpropene (isobutene), a gaseous compound widely used in chemical industries, is metabolized to the epoxide 2-methyl-1,2-epoxypropane. The parent compound has previously been shown to be non-mutagenic in a modified Ames test, whereas the epoxide metabolite gave a positive result. In this study, both compounds have been tested in the in vitro micronucleus test using human lymphocytes. Propylene oxide, a well known mutagenic compound, served as a positive control. It was found that 2-methylpropene had no mutagenic effect, whereas its epoxide induced a statistically significant dose-dependent increase in the number of micronuclei. The effect observed was comparable with that obtained for propylene oxide. |
| Luftstandards | This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Isobutylene is produced, as an intermediate or a final product, by process units covered under this subpart. |
| DHS Chemicals of Interest (COI) | 2-Methylpropene110000Flammable chemical that can be released at a facility. |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 39022000 |
| RTECS-Nr. | UD1010000 |
| Sicherheitshinweise (S) | 24/25 |
| Lagerklasse | 10 - Combustible liquids |
| Gefahrstoffdaten | 9003-27-4(Hazardous Substances Data) |
Anwendungen & Verwendung
Verwenden
polyisobutene (hydrogenated) is an emollient.Polyisobutylene, sometimes called butyl rubber, and other times PIB, is a vinyl polymer. It's very similar to polyethylene and polypropylene in structure, except that every other carbon is substituted with two methyl groups. It is made from the monomer isobutylene, by cationic vinyl polymerization.Polyisobutylene is a synthetic rubber, or elastomer. It's special because it's the only rubber that's gas impermeable. That is, it's the only rubber that can hold air for long periods of time. You may have noticed that balloons will go flat after a few days. This is because they are made of polyisoprene, which is not gas impermeable. Because polyisobutylene will hold air, it is used to make things like the inner tubes, liner layers of tires, and the inner liners of basketballs.
Herstellung & Synthese
synthetische
Silicone rubbers are prepared as follows: Other groups may replace the methyl groups. Silicone rubbers have excellent ozone and weathering resistance, good electrical properties, and good adhesion to metal.