131-11-3 Usage
Uses
Used in Plastics and Resin Industry:
Dimethyl phthalate is used as a plasticizer for cellulose acetate, polyvinyl fluoride coating repellent agents, and solvents. It is also an important solvent in the production of various resins, displaying good film-forming character, adhesion, and water resistance. It is often used with diethyl phthalate in cellulose acetate film, varnish, transparent paper, and molding powder production.
Used in Insect Repellent Industry:
Dimethyl phthalate is used as an insect repellent, providing personal protection against biting insects. It has also been employed as a solvent for cellulose acetate in the insect repellent industry.
Used in Chemical Intermediates:
Dimethyl phthalate serves as an intermediate in the production of rodenticide rat poison, rat finished, chlorine mouse ketone intermediates, and other chemical products.
Used in Gas Chromatography:
Dimethyl phthalate is used as a stationary phase in gas chromatography, a technique used to separate and analyze compounds that can be vaporized without decomposition.
Used in Other Industries:
The product can also be used as a nitrile rubber plasticizer, with good resistance to cold products. It can be mixed with other plasticizers to overcome high volatility and low-temperature crystallization issues. Additionally, it is used as a solvent for DEET oil (crude oil) and DDT.
Dimethyl phthalate
Dimethyl phthalate esters is a broad-spectrum, highly effective insect repellent, it is colorless to pale yellow transparent liquid, is an effective insect repellent ingredient in toilet water, it has a good repellent effect on flies, lice, ants, mosquitoes, cockroaches, midges, gadfly, flat fleas, sand fleas, sand midges, sandflies, cicadas; its repellent effect lasts for a long time, and it can be used in different climatic conditions . Under the conditions of using, it’s chemical stable, displaying both high thermal stability and high resistance to sweat. It has good compatibility with common cosmetic and pharmaceutical agents, can be made of solutions, emulsions, pastes, coating agents, gel, aerosol, mosquito coils, micro-capsules and other special repellent agents, and also can be added to other products or materials (such as toilet water), so that product displays the repellent effect as well. Compared with standard mosquito repellent agent and mosquito repellent gel, it is less toxic, and less irritating, with longer repellent time and other notable features, is a repellent gel replacement.
The above information is edited by the lookchem of Tian Ye.
Toxicity
Dimethyl phthalate displays no toxicity or side effects on the skin and mucous membranes, non-allergic and non-skin-permeable etc., it is very safe to use, it is noted that people with sensitive skin may cause skin allergies reaction if repellent ester component is excessive absorbed .
Production method
Esterified under normal pressure with an excess amount of the anhydride (4-fold) in methanol, excess methanol was refluxed with water, DMP was obtained from the reaction. The 600kg anhydride, 450kg methanol 90-95 ℃', 1050ml concentrated sulfuric acid were added into the reaction pot successively, heated to reflux for 24h. After completion of the reaction, methanol recovery, then neutralized with sodium carbonate, washed with water, and then distilled to obtain the finished product. Industrial grade product dimethyl phthalate purity of ≥99%. Material consumption fixed: anhydride 750kg/t, methanol 445kg/t.
Toxicity grading
Low toxicity
Acute toxicity
Oral-rat LD50: 6800 mg/kg; Oral-Mouse LD50: 6800 mg/kg
Irritation data
Eye-rabbit 119 mg
Flammability hazard characteristics
In the case of fire, high temperature, strong oxidants, it is combustible; combustion exhaust irritating smoke.
Storage feature
It should be stored in a complete package with care; warehouse ventilation, away from obvious flame, heat, and oxidants.
Extinguishing agents
Foam, carbon dioxide, dry powder, sand, water mist.
Professional Standards
TLV-TWA 5 mg/m3; STEL 10 mg/m3
History
Screened during World War II, this repellent is exceptionally effective against A. aegypti, lasting 196 d on cloth. Tests have been run against the newer pests A. albopictus and A. aegypti, including five repellents containing DEET (test standard), a controlled release formulation containing DEET, two dosages of DEET in ethanol, and Avon Skin-So- Soft. On the skin, the repellent chemicals provide significant protection from biting; however, A. albopictus is more sensitive to repellents than A. aegypti.
Production Methods
Dimethyl phthalate is produced industrially from phthalic anhydride and methanol.
Synthesis Reference(s)
Tetrahedron Letters, 37, p. 6375, 1996 DOI: 10.1016/0040-4039(96)01351-2The Journal of Organic Chemistry, 35, p. 3205, 1970 DOI: 10.1021/jo00835a002
Air & Water Reactions
Insoluble in water.
Reactivity Profile
Dimethyl phthalate reacts 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 with caustic solutions. Flammable hydrogen is generated by mixing with alkali metals and hydrides. Can generate electrostatic charges by swirling or pouring [Handling Chemicals Safely, 1980. p. 250].
Health Hazard
Symptoms unlikely from any exposure.
Health Hazard
The acute toxicity of dimethyl phthalate intest animals was found to be very low.Ingestion may produce irritation of the gas trointestinal tract, somnolence, hypotension,and coma. The oral LD50 value in miceis 6800 mg/kg. Animal studies have shownthat administration of this compound causeddevelopmental toxicity, having effects on fer tility. Maternal toxicity in Sprague-Dawleyrats was observed at a dietary treatmentlevel of 5% (Field 1989). There was noeffect on average litter size, fetal bodyweight, or the incidence of skeletal or vis ceral malformations.
Fire Hazard
Dimethyl phthalate is combustible.
Flammability and Explosibility
Nonflammable
Pharmaceutical Applications
Dimethyl phthalate is used in pharmaceutical applications as a solvent and plasticizer for film-coatings such as hydroxypropyl methylcellulose, cellulose acetate and cellulose acetate–butyrate mixtures.In addition to a number of industrial applications, dimethyl phthalate is also widely used as an insect repellent with topical preparations typically applied as a 40% cream or lotion; it has also been applied as a tent fabric treatment.
Contact allergens
Phthalates are plasticizers and increase the flexibility of plastics. They are also found in deodorant formulations, perfumes, emollients, and insect repellents.
Safety Profile
Moderately toxic by
ingestion and intraperitoneal routes. Mldly
toxic by inhalation. Experimental
teratogenic and reproductive effects.
Mutation data reported. An eye irritant. A
pesticide and insect repellent. Combustible
when exposed to heat or flame; can react
with oxidizing materials. To fight fire, use
CO2, dry chemical. When heated to
decomposition it emits acrid smoke and
irritating fumes. See also ESTERS.
Safety
In pharmaceutical applications, dimethyl phthalate is used in film coating and as a topically applied insect repellent.Acute exposure to the eyes and mucous membranes can cause irritation, although dimethyl phthalate is considered less irritant than diethyl phthalate. Inhalation of dimethyl phthalate can cause irritation of the respiratory tract; oral ingestion can cause a burning sensation in the mouth, vomiting, and diarrhea. Owing to the low water solubility and relatively high lipid solubility, dimethyl phthalate may accumulate in body tissues after chronic exposure, which may cause central nervous system depression.
Although some animal studies have suggested that high concentrations of dimethyl phthalate may be teratogenic or cause mutagenic effects with bacteria,(5,6) other studies have shown no adverse effects.(7) There are no confirmed reports of human reproductive or developmental effects, and the compound is not generally regarded as a carcinogenic material.
LD50 (chicken, oral): 8.5g/kg
LD50 (guinea pig, oral): 2.4g/kg
LD50 (mouse, IP): 1.38g/kg
LD50 (mouse, oral): 6.8g/kg
LD50 (rabbit, oral): 4.40g/kg
LD50 (rat, IP): 3.38g/kg
LD50 (rat, oral): 6.80g/kg
Source
May leach from plastic products (e.g., tubing, containers) used in laboratories during
chemical analysis of aqueous samples.
Environmental Fate
Biological. In anaerobic sludge, degradation occurred as follows: monomethyl phthalate to phthalic acid to protocatechuic acid followed by ring cleavage and mineralization (Shelton et al., 1984). In a static-culture-?ask screening test, dimethyl phthalate showed significant biodegradation with rapid adaptation. The ester (5 and 10 mg/L) was statically incubated in the dark at 25°C with yeast extract and settled domestic wastewater inoculum. After 7 days, 100% biodegrada-tion was achieved (Tabak et al., 1981).
Photolytic. An aqueous solution containing titanium dioxide and subjected to UV light (λ >290 nm) yielded mono- and dihydroxyphthalates as intermediates (Hustert and Moza, 1988).
Chemical/Physical. Hydrolyzes in water forming phthalic acid and methyl alcohol (Wolfe et al., 1980).
storage
Dimethyl phthalate is sensitive to prolonged exposure to light and it should therefore be stored in a cool, dark, dry, well-ventilated area that is protected from physical damage, and isolated from incompatible substances. Containers of dimethyl phthalate may be hazardous when empty as they may retain product residues such as vapors and liquids. There is a slight fire hazard when exposed to heat, and above the flash point explosive vapor–air mixtures may be formed.Carbon dioxide and carbon monoxide are released when dimethyl phthalate is heated to decomposition. Solutions of dimethyl phthalate in acetone, dimethyl sulfoxide, ethanol (95%), and water are stable for 24 hours under normal laboratory conditions.
Incompatibilities
Dimethyl phthalate is incompatible with strong acids or bases, nitrates, and strong oxidizing agents. As with other phthalates, contact with plastics should be avoided.
Regulatory Status
Dimethyl phthalate is included in a number of topical pharmaceutical formulations. Included in the FDA Inactive Ingredients Database (oral tablets, sustained action). As from 1992, dimethyl phthalate is no longer registered for use as a pesticide in California.
Check Digit Verification of cas no
The CAS Registry Mumber 131-11-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,3 and 1 respectively; the second part has 2 digits, 1 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 131-11:
(5*1)+(4*3)+(3*1)+(2*1)+(1*1)=23
23 % 10 = 3
So 131-11-3 is a valid CAS Registry Number.
InChI:InChI=1/C10H10O4/c1-13-9(11)7-5-3-4-6-8(7)10(12)14-2/h3-6H,1-2H3
131-11-3Relevant articles and documents
Microwave-promoted Beller's synthesis of substituted phthalates
Yang, Yun-Yun,Shou, Wang-Ge,Wang, Yan-Guang
, p. 1383 - 1390 (2006)
A rapid and efficient synthesis of substituted phthalates via microwave-promoted Beller's reaction of aldehydes, amides, and dimethyl acetylenedicarboxylate is described. This one-pot, multicomponent reaction was performed under acetic anhydride-free and solvent-free conditions. Copyright Taylor & Francis Group, LLC.
Comparison of three methods for the methylation of aliphatic and aromatic compounds
Lee, Hyejung,Feakins, Sarah J.,Lu, Zhiyao,Schimmelmann, Arndt,Sessions, Alex L.,Tierney, Jessica E.,Williams, Travis J.
, p. 1633 - 1640 (2017)
Rationale: Methylation protocols commonly call for acidic, hot conditions that are known to promote organic 1H/2H exchange in aromatic and aliphatic C–H bonds. Here we tested two such commonly used methods and compared a third that avoids these acidic conditions, to quantify isotope effects with each method and to directly determine acidic-exchange rates relevant to experimental conditions. Methods: We compared acidic and non-acidic methylation approaches catalyzed by hydrochloric acid, acetyl chloride and EDCI (1-ethyl-3-(3-dimethylaminopropyl)carbodiimide)/DMAP (4-dimethylaminopyridine), respectively. These were applied to two analytes: phthalic acid (an aromatic) and octacosanoic acid (an aliphatic). We analyzed yield by gas chromatography/flame ionization (GC/FID) and hydrogen and carbon isotopic compositions by isotope ratio mass spectrometry (GC/IRMS). We quantified the 1H/2H exchange rate on dimethyl phthalate under acidic conditions with proton nuclear magnetic resonance (1H-NMR) measurements. Results: The δ2H and δ13C values and yield were equivalent among the three methods for methyl octacosanoate. The two acidic methods resulted in comparable yield and isotopic composition of dimethyl phthalate; however, the non-acidic method resulted in lower δ2H and δ13C values perhaps due to low yields. Concerns over acid-catalyzed 1H/2H exchange are unwarranted as the effect was trivial over a 12-h reaction time. Conclusions: We find product isolation yield and evaporation to be the main concerns in the accurate determination of isotopic composition. 1H/2H exchange reactions are too slow to cause measurable isotope fractionation over the typical duration and reaction conditions used in methylation. Thus, we are able to recommend continued use of acidic catalysts in such methylation reactions for both aliphatic and aromatic compounds.
Determination of Total Phthalate in Urine by Gas Chromatography
Albro, Phillip W.,Jordan, Sandra,Corbett, Jean T.,Schroeder, Joanna L.
, p. 247 - 250 (1984)
While urine rarely contains significant quantities of phthalate diesters, it does contain a variety of metabolites (phthalate monoesters) including conjugates.In the absence of bacterial action following excretion, the metabolites retain an intact phthalate ring.A procedure for the hydrolysis of phthalate esters and metabolites to free phthalic acid, recovery and esterification of the acid, and gas chromatographic quantification of the product ester all relative to an internal standard of 4-chlorophthalate has been developed.The measurement limit is 0.5 nmol of total phthalate/mL of urine, and the relative standard deviation is approximately 1.8percent for four or more replicates.The assay is linear between 0.5 and 50 nmol/mL urine, which spans the range of phthalate levels found thus far in human urine samples.The procedure can also be used to determine levels of isophthalate and terephthalate simultaneously with phthalate.
Preparation and isolation of isobenzofuran
Peters, Morten K.,Herges, Rainer
, p. 2659 - 2662 (2017)
The synthesis, isolation and characterization of isobenzofuran are described in this publication. Isobenzofuran is of general interest in synthetic and physical organic chemistry because it is one of the most reactive dienes known. A number of synthetic pathways have been published which all suffer from disadvantages such as low yields and difficult purification. We present a synthetic pathway to prepare isobenzofuran in laboratory scale with high yields, from affordable, commercially available starting materials.
Cleavage of 7- And 8-nitropyrido[1,2-a]benzimidazoles on treatment with dimethyl acetylenedicarboxylate
Varlamov, Alexey V.,Savitkina, Elena A.,Krapivko, Anatoly P.,Chernyshev, Alexey I.,Levov, Alexander N.
, p. 127 - 128 (2005)
7-Nitropyrido[1,2-a]benzimidazole and 8-nitropyrido[1,2-a]benzimidazole undergo cleavage-recyclization under the action of an excess of dimethyl acetylenedicarboxylate.
Barrelene Derivatives-Potential Modules for Assembly
Beerly, Rene,Rebek, Julius
, p. 1813 - 1816 (1995)
Dihydrobarrelene tetraamide 8 was prepared by Diels-Alder reaction of 4 and 5 and indirect transformation of the ester into amide groups.The crystal structure of 8 showed an unpredicted conformation of the four amide groups.
Carbon-Carbon Double Bond Formation Accompanying Hydride Transfer from a Carbanion to 5-Carbalumiflavin
Farng, Oscar L.,Bruice, Thomas C.
, p. 185 - 186 (1984)
Oxidation of the carbanions of dimethyl trans-(1,2-2H0)dihydrophthalate and the corresponding (1,2-2H2) analogue occurs by H- and D- transfer to the 5-position of 5-carbalumiflavin.
The palladium-catalyzed addition of various vinyl compounds to dimethyl acetylenedicarboxylate
Stephan, Constantin,Munz, Christina,Dieck, Heindirk tom
, p. 223 - 227 (1993)
The catalyst precursor (E = COOCH3) reacts with simple vinyl compounds and dimethyl acetylenedicarboxylate to give cyclic 1:2-, 2:1- and 2:2-addition products, namely substituted cyclohexadiene or benzene, cyclopentene and cyclooctadiene derivatives, which can be separated by column chromatography.Palladacyclopent-2-enes, palladacyclohepta-2,4-dienes and palladacyclohept-4-enes, which cannot be trapped, are suggested to be intermediates in the reaction.Different types of products are obtained depending on the nature of the vinyl compound: while α-methyl styrene gives only a cyclohexadiene species following 1:2-addition, vinyl ethers along with 1:2-addition undergo 2:1- and even 2:2-addtition, and cyclopentene and 1,5-cyclooctadiene derivatives are formed.In the course of the reaction with vinyl ethers, alcohols are formed, probably in a reductive elimination step from Pd-H-intermediates in which an alkoxy group occupies a β-position and also in palladium-mediated aromatization of initially formed alkoxy cyclohexadiene and bisalkoxy cyclohexene products.Yields and product ratios can be influence by changing the fixed ligand in the catalyst complex.
Arene synthesis by extrusion reaction X. Synthesis of arenes by deoxygenation of endoxides with cyclopentadienyltitanium trichloride/lithium aluminum hydride and dicyclopentadienyltitanium dichloride/lithium aluminum hydride
Wong, Chi Hung,Hung, Chi Wai,Wong, Henry N. C.
, p. 9 - 14 (1988)
The two homogeneous systems, cyclopentadienyltitanium trichloride/lithium aluminum hydride and dicyclopentadienyltitanium dichloride/lithium aluminum hydride have been utilized to deoxygenate 1,4-endoxides in tetrahydrofuran.The results show that they can provide corresponding arenes in fair yields.
Reactions of 2,3-dicarbomethoxy-7-oxabicycloheptadiene with molybdenum carbonyls
Sun, Chia-Hsing,Chow, Tahsin J.
, p. C21 - C24 (1987)
Thermolysis with either Mo(CO)6 or Mo(CH3CN)3(CO)3 of 2,3-dicarbomethoxy-7-oxabicycloheptadiene (I) gave three major products, i.e. dimethyl phthalate (V), 3,4-dicarbomethoxyfuran (VI), and a dimeric ketone (IX) linked in an exo-trans-exo orientation.The formation of V and IX indicates two reaction pathways which start from a common organometallic intermediate.Compound VI is the major product in the thermal decomposition of IX.
