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Dimethylterephthalat
DMT · dimethy · TEREPHTHALIC ACID DIMETHYL ESTER · 1,4-Benzenedicarboxylicacid,dimethylester · di-meterephthalate · Dimethyl p-phthalate · Terephthalate, dimethyl · Terephthalic acid methyl ester
Identifikatoren & physikalische Daten
| CAS No. | 120-61-6 |
|---|---|
| Summenformel | C10H10O4 |
| Durchschnittliche Molmasse | 194,18 g/mol |
| Monoisotopische Masse | 194,0579088 g/mol |
| SMILES | COC(=O)c1ccc(C(=O)OC)cc1 |
| InChIKey | WOZVHXUHUFLZGK-UHFFFAOYSA-N |
| PubChem CID | 8441 |
| ChEMBL | CHEMBL1870757 |
| ChEBI | CHEBI:156286 |
| EC No. | 204-411-8 |
| DTXSID | DTXSID0020498 |
| Lokaler Name | Dimethylterephthalat |
Chemische & physikalische Eigenschaften
| XLogP | 2,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 52,6 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 4 |
| Schwere Atome | 14 |
| Formalladung | 0 |
| Komplexität | 192 |
| Stoffklassen | Other Classes -> Other Aromatic Compounds |
| SpringerMaterials Properties | 13C nuclear magnetic resonance spectrum |
| Pestizide | Pesticide -> EPA IRIS |
| LogP (Verteilungskoeffizient) | log Kow = 2.252.35 |
| Dichte | 1.2 at 68 °F 1.08 at 145 °C (liquid) (USCG, 1999) - Denser than waterwill sink1.075 g/cu cm at 141 °C1.2 g/cm³1,29 g/cm3 |
| Viscosity | Liquid viscosity = 1.0682X10-3 Pa.s |
| Color/Form | Colorlesss crystalsNEEDLES FROM ETHER |
| Löslichkeit | less than 1 mg/mL at 55 °F (NTP, 1992)Soluble in ether and hot alcoholSoluble in chloroformslightly soluble in ethanol. methanol0.3 G/ML IN HOT WATERIn water, 19 mg/L at 25 °CSolubility in water at 13 °C: very poorwater: slightly soluble0.0493g/L at 20°CIt is slightly soluble in water but soluble in hot alcohol and ether. |
| Flammpunkt | 308 °F (NTP, 1992)141 °C146 °C OC308 °F (153 °C) (Open cup)141 °C c.c.154 °C |
| Siedepunkt | 572 °F at 760 mmHg (sublimes) (NTP, 1992)288 °C |
| Decomposition | When heated to decomposition it emits acrid smoke and irritating fumes. |
| Schmelzpunkt | 284 to 288 °F (NTP, 1992)141 °CHeat of fusion at melting point = 3.1630X10+7 J/kmol140 °C |
| Dampfdichte | 1.04 (vs air) |
| Dampfdruck | 1.15 mm Hg ( 93 °C) |
| Brechungsindex | 1.4752 |
| Lagerbedingungen | Store below +30°C. |
| Aggregatzustand | Flakes or Pellets |
| pKa (Säurekonstante) | 0[at 20 ℃] |
| Farbe | White |
| Explosionsgrenze | 0.8-11.8%(V) |
| Spezifische Wärmekapazität | Cp(crystal): 1.34 J/(g·K), at 25℃ |
| Merck | 14,9162 |
| BRN | 1107185 |
| Henry-Konstante | 7.4×10-2 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| Stabilität | Stable. Incompatible with strong acids, strong bases, strong oxidizing agents. |
| InChI | 1S/C10H10O4/c1-13-9(11)7-3-5-8(6-4-7)10(12)14-2/h3-6H,1-2H3 |
| InChIKey | WOZVHXUHUFLZGK-UHFFFAOYSA-N |
| SMILES | COC(=O)c1ccc(cc1)C(=O)OC |
| LogP (Verteilungskoeffizient) | 2.25 at 25℃ |
| CAS Datenbank | 120-61-6(CAS DataBase Reference) |
| EPA chemische Informationen | Dimethyl terephthalate (120-61-6) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 75.8% (405 of 534) of all reports.WarningH317 (13.7%): May cause an allergic skin reaction [Warning Sensitization, Skin]P261, P272, P280, P302+P352, P321, P333+P317, P362+P364, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 534 reports by companies from 9 notifications to the ECHA C&L Inventory. |
|---|---|
| Regulatorische Informationen | Chemical: 1,4-Benzenedicarboxylic acid, dimethyl ester1,4-Benzenedicarboxylic acid, 1,4-dimethyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,4-Benzenedicarboxylic acid, 1,4-dimethyl ester 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: 11-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/151731,4-Benzenedicarboxylic acid, dimethyl ester: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right. |
| DOT-Kennzeichnung | Poison |
| Brandgefahren | This chemical is combustible. (NTP, 1992)Combustible. Finely dispersed particles form explosive mixtures in air. |
| Gesundheitsgefahren | Molten DMT will cause severe burns of skin on contact. (USCG, 1999) |
| Gefahrenübersicht | An irritant[ICSC] May be irritating to the eyes[HSDB] Causes urinary tract calculi in high-dose animal studiesThere are no published reports of human studies[AIHA] An irritant[MSDSonline] |
| Reaktive Gruppe | Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters |
| Special Reports | European Chemicals BureauIUCLID Dataset, Dimethyl terephthalate (120-61-6), 62 pp. (2000 CD-ROM edition). Available from the Database Query page at: http://ecb.jrc.it/esis/esis.php as of May 13, 2008 |
| Reactivity Profile | DIMETHYL TEREPHTHALATE is an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. Can generate electrostatic charges. [Handling Chemicals Safely 1980. p. 250]. This compound is sensitive to heat. The molten material reacts with water due to the temperature. This compound is incompatible with strong oxidizers, strong acids and strong bases. |
| 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. Dimethyl terephthalate is produced, as an intermediate or a final product, by process units covered under this subpart. |
| Chemical Dangers | Decomposes on burning. This produces irritating fumes. |
| Physical Dangers | Dust explosion possible if in powder or granular form, mixed with air. |
| Air and Water Reactions | When mixed with air, the vapor or dust forms very hazardous and highly reactive mixtures. (NTP, 1992). Insoluble in water. |
| Brandbekämpfung | Fire Extinguishing Agents: Water, dry chemical, foam, carbon dioxide (USCG, 1999)Use water spray, foam, powder, carbon dioxide. |
| Erste-Hilfe-Maßnahmen | Fresh air, rest.Rinse and then wash skin with water and soap.First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth. |
| 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. |
| Sichere Lagerung | Store in an area without drain or sewer access. |
| Firefighting Hazards | Poisonous gases are produced in fire. |
| Brandbekämpfungsverfahren | Extinguish with water, dry chemicals, foam, or carbon dioxide.From a secure, explosion-proof location, use water spray to cool exposed containers. If cooling streams are ineffective (venting sound increases in volume and pitch, tank discolors, or shows any signs of deforming), withdraw immediately to a secure position.Alcohol foam. Water or foam may cause frothing. |
| Lagerbedingungen | Dimethyl terephthalate is stored molten in insulated heated tanks, and is perferentially shipped molten in insulated rail tank cars or tank trucks. It is also solidified into briquettes or flakes, and shipped in 1 ton or 25 kg bags.Store in tightly closed containers in a cool, well-ventilated area away from oxidizers, nitrates, acids and sources of ignition |
| Freisetung ohne Brand | SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then dampen the solid spill material with toluene, then transfer the dampened material to a suitable container. Use absorbent paper dampened with toluene to pick up any remaining material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent-wash all contaminated surfaces with toluene followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. |
| Entsorgungsverfahren | SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. 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 soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations. |
| Verschüttetes entsorgen | Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered sealable containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations. |
| Preventive Measures | SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place. |
| Isolation and Evacuation | Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: |
| Zielorgane | Urinary |
| Ökotoxizitätswerte | LC50 Pimephales promelas (fathead minnow) 9.6 mg/L/96 hr, staticLC50 Daphnia magna (water flea) 30.4 mg/L/48 hr /Conditions of bioassay not specified in source examined/LC50 Daphnia magna (water flea) > 100 mg/L/96 hr, staticLC50 Dugesia tigrina (flatworm) > 100 mg/L/96 hr, staticFor more Ecotoxicity Values (Complete) data for DIMETHYL TEREPHTHALATE (8 total), please visit the HSDB record page. |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 400(SRC), determined from a log Kow of 2.25(2) and a regression-derived equation(3), indicates that dimethyl terephthalate is expected to have moderate mobility in soil(SRC). Volatilization of dimethyl terephthalate from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 1.3X10-4 atm-cu m/mole(SRC), derived from its vapor pressure, 0.01 mm Hg(4), and water solubility, 19 mg/L(5). Dimethyl terephthalate is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Dimethyl terephthalate, at a concentration of 0.5%, degraded completely in 15 days at 30 °C in soil with a pH of 8.2 and 60% moisture content(6).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 400(SRC), determined from a log Kow of 2.25(2) and a regression-derived equation(3), indicates that dimethyl terephthalate is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 1.3X10-4 atm-cu m/mole(SRC), derived from its vapor pressure, 0.01 mm Hg(4), and water solubility, 19 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 13 hours and 8.3 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 11(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). A 3 day river die-away test using 50, 40, and 5 ppm dimethyl terephthalate resulted in 100% biodegradation in all three tests of river water, and 27, 38, and 49% biodegradation in the three tests of sea water(8) suggesting dimethyl terephthalate is expected to biodegrade in aquatic environments(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dimethyl terephthalate, which has a vapor pressure of 0.01 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase dimethyl terephthalate 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 28 days(SRC), calculated from its rate constant of 5.7X10-13 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Dimethyl terephthalate does contain chromophores that absorb at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC). |
| Ökotoxizitätsauszüge | /PLANTS/ Ryegrass, radish, lettuce /were tested in/ 7-Day germination exposures to /dimethyl terephthalate/ concentrations of 0, 1, 10, 100, or 1000 mg/L. There were 80 seeds used for each exposure test level and 40 seeds for control. ... No Adverse Effect Concn: 10 mg/L (rye grass, radish ), 1 mg/L (lettuce)./PLANTS/ Corn, marigold, lettuce, radish /seedlings were tested in/ 1-week phytotoxicity /aasays/ to /dimethyl terephthalate/ concentrations of 0, 100, and 1000 mg/L. There were 10 corn seedlings and 20 seedlings for the other species per exposure level. ... No Adverse Effect Concn: >1000 mg/L (radish, marigold, lettuce), >100 mg/L (corn). |
| Signs and Symptoms | Redness. |
| Ongoing Test Status | The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=120-61-6] |
| Effluent Concentrations | The concentration of dimethyl terephthalate in the waste water from a dimethyl terephthalate manufacturing plant was less than 0.5 mg/L whereas its acid was found at 459 mg/L(1). This is due to the hydrolysis of dimethyl terephthalate to the acid(1). Dimethyl terephthalate was identified in an industrial wastewater survey sample extracts at a concentration of 557 ng/uL in the organics industry and 21 ng/uL in the organics and plastics industry(2). Dimethyl terephthalate was identified, not quantified, in advanced waste treatment concentrates in Lake Tahoe, CA and in Pomona, CA(3). |
| ICSC Environmental Data | The substance is harmful to aquatic organisms. |
| EPA IRIS Information | Dimethyl terephthalate (DMT)Urinary1 x 10 ^-1 mg/kg-day |
| Soil Adsorption/Mobility | The Koc of dimethyl terephthalate is estimated as 400(SRC), using a log Kow of 2.25(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that dimethyl terephthalate is expected to have moderate mobility in soil. |
| Atmospheric Concentrations | RURAL/REMOTE: Dimethyl terephthalate was identified, not quantified, in a forest atmosphere in West Germany(1). |
| Human Toxicity Excerpts | /HUMAN EXPOSURE STUDIES/ An oily paste containing 80% DMT showed no irritant effects 24 hr after 10 applications to human skin./OTHER TOXICITY INFORMATION/ ... Calculations based on the solubility of calcium terephthalate indicate that humans would have to absorb at least 2.0 grams per day terephthalic acid or 2.5 grams per day dimethyl terephthalate to develop bladder stones. |
| Wassergefährdungsklasse (WGK) | 1 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | 3256 |
| Zollcode | 2917 37 00 |
| RTECS-Nr. | WZ1225000 |
| R-Sätze (R) | 36/37/38 |
| Toxizität | LD50 orally in Rabbit: 3200 mg/kg |
| Sicherheitshinweise (S) | 24/25 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 120-61-6(Hazardous Substances Data) |
| Selbstentzündungstemperatur | 520 °C DIN 51794 |
Anwendungen & Verwendung
Beschreibung
Dimethyl terephthalate (DMT) is an organic compound with the formula C6H4(CO2CH3)2. It is the diester formed from terephthalic acid and methanol. It is a white solid that melts to give a distillable colourless liquid.
Verwenden
Dimethyl terephthalate is used in the production of polyesters, including polyethylene terephthalate (PET) and poly trimethylene terephthalate. It consists of benzene substituted with carboxy methyl groups (CO2CH3) at the 1 and 4 positions. Because DMT is volatile, it is an intermediate in some schemes for the recyclic of PET, e.g. from plastic bottles. Hydrogenation of DMT affords the diol cyclohexanedimethanol, which is a useful monomer.
Herstellung & Synthese
synthetische
Several processes have been developed for the preparation of dimethyl terephthalate from p-xylene, but the most important proceeds as follows: The oxidation steps are carried out in the liquid phase at about 170C and 1.5 MPa (15 atmospheres) in the presence of a cobalt acetate or naphthenate catalyst whilst the esterifications are conducted at about 150C. Dimethyl terephthalate may also be produced by esterification of terephthalic acid.