基本情報
- 標準SMILES
CC(C)COC(=O)c1ccccc1C(=O)OCC(C)C- InChIKey
MGWAVDBGNNKXQV-UHFFFAOYSA-N- 分子式
- C16H22O4
- 平均分子量
- 278.34 g/mol
- 単同位体質量
- 278.15180918
名称と識別子
- 優先名称
- Diisobutyl phthalate
- IUPAC
- bis(2-methylpropyl) benzene-1,2-dicarboxylate
- 英語名
- Diisobutylphthalate
- 分子式
- C16H22O4
- 分子量
- 278.34
名称と別名
名称をさらに表示
データベース識別子
- CAS
84-69-5- PubChem CID
- 6782
- DTXSID
DTXSID9022522- ChEMBL
CHEMBL1370662- ChEBI
CHEBI:79053- UNII
- IZ67FTN290
- EC Number
- 201-553-2
- Nikkaji
- J3.535A
物性
構造計算による物性
- XLogP
- 4.1
- 極性表面積
- 52.6 Ų
- 水素結合供与体数
- 0
- 水素結合受容体数
- 4
- 回転可能結合数
- 8
- 重原子数
- 20
- 形式電荷
- 0
- 複雑度
- 290
実験および物理化学的性質
LogP
log Kow = 4.11
4.11
4.11
Density
1.047 at 68 °F (USCG, 1999) - Denser than water; will sink
1.0490 g/cu cm at 15 °C
1.04 g/cm³
Solubility
Insoluble (NTP, 1992)
Phthalate esters are soluble to various extents in many common organic solvents and oils, but have a relatively low solubility in water. /Phthalate esters/
Soluble in carbon tetrachloride
In water, 6.2 mg/L at 24 °C
0.0062 mg/mL at 24 °C
Solubility in water, g/100ml at 20 °C: 0.0001
Flash Point
385 °F (NTP, 1992)
365 °F (185 °C) (Open cup)
185 °C o.c.
Boiling Point
563 to 568 °F at 760 mmHg (NTP, 1992)
296.5 °C; 159 °C at 4 mm Hg
296.00 °C. @ 760.00 mm Hg
320 °C
Melting Point
-83 °F (NTP, 1992)
-64 °C
< 25 °C
-37 °C
Vapor Density
9.59 (NTP, 1992) - Heavier than air; will sink (Relative to Air)
Relative vapor density (air = 1): 9.6
Vapor Pressure
0.00665 [mmHg]
4.76X10-5 mm Hg at 25 °C /from experimentally derived coefficients/
Vapor pressure, Pa at 20 °C: 0.01
物理化学的性質
- 融点
- -64 °C · -64 °C
- 沸点
- 296.5 °C · 296.5 °C
- 比重(密度)
- 1.039 g/cm3 · 1.039 g/cm3
安全と法規制
GHS分類
GHS Classification
Danger
H360Df: May damage the unborn child; Suspected of damaging fertility [Danger Reproductive toxicity]
P203, P280, P318, P405, and P501 (click each P-code to see the statement)
This chemical does not meet GHS hazard criteria for 0.1% (1 of 744) of reports.
危険有害性情報
Regulatory Information
Chemical: 1,2-Benzenedicarboxylic acid, bis(2-methylpropyl) ester
Hazard Traits - Carcinogenicity; Developmental Toxicity; Endocrine Toxicity; Immunotoxicity; Reproductive Toxicity; Respiratory Toxicity;Authoritative List - CECBP - Priority Chemicals; EC Annex VI CMRs - Cat. 1B; EC EDs;Report - if used as a fragrance or flavor ingredient
Regulation (EC) No 178/2002 (amended)
1,2-Benzenedicarboxylic acid, 1,2-bis(2-methylpropyl) ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,2-Benzenedicarboxylic acid, 1,2-bis(2-methylpropyl) 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: 30-08-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/13519;Status: Active Update: 22-07-2013 https://echa.europa.eu/registration-dossier/-/registered-dossier/1354;Status: Cease Manufacture Update: 15-09-2010 https://echa.europa.eu/registration-dossier/-/registered-dossier/1834;Status: Active Update: 12-11-2012 https://echa.europa.eu/registration-dossier/-/registered-dossier/1908;Status: Cease Manufacture Update: 03-01-2013 https://echa.europa.eu/registration-dossier/-/registered-dossier/7169;Status: Cease Manufacture Update: 11-02-2014 https://echa.europa.eu/registration-dossier/-/registered-dossier/1730
Restricted substance: Diisobutyl phthalate;EC: 201-553-2;Restriction condition document: PDF link
Fire Hazards
This chemical is combustible. (NTP, 1992)
Combustible. Gives off irritating or toxic fumes (or gases) in a fire.
Hazards Summary
Can be absorbed through skin; Effects on reproduction in animal testing: increase in resorptions in absence of maternal toxicity; [ICSC] Oral LD50 (mouse) = 10,000 mg/kg (Effects include weakness and coma.); [ChemIDplus] Like dioctyl phthalate, it may cause CNS depression and mild liver toxicity after ingestion of large amounts; [HSDB] A very mild skin and eye irritant, based on animal studies; [CHEMINFO] An irritant; [MSDSonline] See PHTHALATE ESTERS.
Special Reports
U.S. Consumer Product Safety Commission; Toxicity Review for Diisobutyl Phthalate (84-69-5)(July 14, 2011).[Available from, as of November 5, 2012: http://www.cpsc.gov/]
European Chemicals Bureau; IUCLID Dataset, Diisobutyl Phthalate (84-69-5), 60 pp. (2000 CD-ROM edition). Contains information on use, toxicology, and environmental effects of this chemical as supplied to the European Union by industry.[Available from, as of April 24, 2008: http://esis.jrc.ec.europa.eu/]
Nat'l Research Council Canada; Phthalate Esters in the Aquatic Environment (1980) NRCC No. 17583
USEPA; Ambient Water Quality Criteria Doc: Phthalate Esters (1980) EPA 440/5-80-067
USEPA/ECAO; Atlas Document for: Phthalate Esters (1980)
TSCA Requirements
Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. Effective date 09/29/06; Reporting date 11/28/06.
Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 1,2-Benzenedicarboxylic acid, bis(2-methylpropyl) ester is included on this list. Effective date 10/04/82; Sunset date 10/04/92.
Reactivity Profile
DI-ISOBUTYL PHTHALATE reacts with acids to liberate heat along with isobutyl alcohol and phthalic acid. May react sufficiently exothermically with strong oxidizing acids to ignite the reaction products. Heat is also generated by interaction with caustic solutions. Flammable hydrogen is generated by mixing with alkali metals and hydrides. Can generate electrostatic charges in handling [Handling Chemicals Safely, 1980. p. 250].
安全と保護具
Fire Fighting
Fire Extinguishing Agents Not to Be Used: Water or foam amy cause frothing.;Fire Extinguishing Agents: Dry powder, carbon dioxide, foam (USCG, 1999)
Use water spray, alcohol-resistant foam, powder, carbon dioxide.
First Aid Measures
Fresh air, rest.
Rinse and then wash skin with water and soap.
Rinse with plenty of water for several minutes (remove contact lenses if easily possible).
Rinse mouth.
First Aid
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.;SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.;INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.;INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)
Nonfire Spill Response
SMALL SPILLS AND LEAKAGE: If you spill this chemical, use absorbent paper to pick up all liquid spill 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 alcohol followed by washing with a strong 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.;STORAGE PRECAUTIONS: You should store this chemical under refrigerated temperatures and away from oxidizers, mineral acids and bases. (NTP, 1992)
Disposal Methods
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 quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
Preventive Measures
Strict hygiene! Avoid exposure of (pregnant) women!
Do not eat, drink, or smoke during work.
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.
毒性情報
Body Burden
Diisobutyl phthalate was measured in 48-hr expired air samples of pregnant New York women at 0.03-1.3 ug/cu m in samples taken Mar to Sept 2000 and in pregnant Krakow, Poland women at 0.31-8.1 ug/cu m in samples taken Nov 2000 to Mar 2001(1).
Interactions
20 ug/insect DIBP applied topically on the ventral abdomen or by intrathoracic injection /to Musca domestica (housefly)/ did not exert appreciable toxicity. House flies were pretreated topically with DIBP (20 ug/insect), followed 30 min later by topical application of a non-toxic dose of chlorpyrifos (0.008 ug/insect, LD50=0.04 ug/insect) in order to test for a possible synergistic action. A mortality of 35% was observed within 24 hr.
10 white mice/group received ip application of 500 mg/kg DIBP, after 30 min ip injection of 60 mg/kg hexobarbital sodium. Control animals received vehicle instead of DIBP. The treatment of mice with DIBP prior to hexobarbital /sodium/ caused prolongation of sleeping time (control: 46 min; DIBP: 72 min). DIBP appeared to demonstrate CNS depression.
10 male ICR mice/group received ip application of DIBP on 3 consecutive days (1.921, 0.768, 0.384 mL/kg) and 50 mg/kg pentobarbital sodium ... . The pretreatment of mice with DIBP caused a dose-related significant reduction of sleeping time. ...
Health Effects
Phthalate esters are endocrine disruptors. Animal studies have shown that they disrupt reproductive development and can cause a number of malformations in affected young, such as reduced anogenital distance (AGD), cryptorchidism, hypospadias, and reduced fertility. The combination of effects associated with phthalates is called 'phthalate syndrome’. (A2883)
Ecotoxicity Values
LC50; Species: Pimephales promelas (Fathead minnow) age 29 days, mean length 17.6 mm, mean weight 0.056 g; Conditions: flow through, 25.1 °C, pH 7.38, hardness 44.8 mg/L CaCO3, alkalinity 49.4 mg/L CaCO3, dissolved oxygen 7.0 mg/L; Concentration: 0.9 mg/L for 96 hr (95% confidence limit: 0.73-1.10 mg/L) /99+% purity/
EC50; Species: Pimephales promelas (Fathead minnow) age 29 days, mean length 17.6 mm, mean weight 0.056 g; Conditions: flow through, 25.1 °C, pH 7.38, hardness 44.8 mg/L CaCO3, alkalinity 49.4 mg/L CaCO3, dissolved oxygen 7.0 mg/L; Concentration: 0.73 mg/L for 96 hr (95% confidence limit: 0.73-1.10 mg/L); Effect: Affected fish lost schooling behavior, were hypoactive and underreactive to external stimuli, were darkly colored, and lost equilibrium prior to death. /99+% purity/
LC50; Species: Leuciscus idus (Orfe); Conditions: static, 20 °C; Concentration: 4.2 mg/L for 48 hr /Marlowet EF emulsifier added/
EC50; Species: Scenedesmus subspicatus (Green algae); Concentration: 1 mg/L for 72 hr; Effect: biomass /Conditions of bioassay not specified in source examined/ /Purity 97.5% (peak area)/
For more Ecotoxicity Values (Complete) data for DIISOBUTYL PHTHALATE (6 total), please visit the HSDB record page.
Environmental Fate
TERRESTRIAL FATE: Based on a classification scheme(1), a log Koc value of 3.14(2), indicates that diisobutyl phthalate is expected to have low mobility in soil(SRC). Volatilization of diisobutyl phthalate from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.8X10-6 atm-cu m/mole(SRC), based upon its vapor pressure, 4.76X10-5 mm Hg(3), and water solubility, 6.2 mg/L(4). Diisobutyl phthalate is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Utilizing the Japanese MITI test, 98% of the Theoretical BOD was reached in 4 weeks(5) indicating that biodegradation is an important environmental fate process in soil(SRC).
AQUATIC FATE: Based on a classification scheme(1), a log Koc value of 3.14(2), indicates that diisobutyl phthalate is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 2.8X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 4.76X10-5 mm Hg(4), and water solubility, 6.2 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 22 and 165 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 240(SRC), from its log Kow of 4.11(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is high, provided the compound is not metabolized by the organism(SRC). Diisobutyl phthalate was completely biodegraded during 6 day die-away tests using water from an urban river and polluted seawater(9), indicating that biodegradation may be an important environmental fate process in water(SRC).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), diisobutyl phthalate, which has a vapor pressure of 4.76X10-5 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase diisobutyl phthalate 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 1.2 days(SRC), calculated from its rate constant of 9.3X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase diisobutyl phthalate may be removed from the air by wet and dry deposition(SRC). Diisobutyl phthalate contains chromophores that absorb at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).
Food Survey Values
Diisobutyl phthalate was identified as a volatile flavor component of a baked potato(1).
Mean concentrations of diisobutyl phthalate in food as a source of exposure among Europeans(1).[Table#5306]
Adverse Effects
Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.;Reproductive Toxin - A chemical that is toxic to the reproductive system, including defects in the progeny and injury to male or female reproductive function. Reproductive toxicity includes developmental effects. See Guidelines for Reproductive Toxicity Risk Assessment.
Exposure Routes
The substance can be absorbed into the body through the skin and by ingestion.
Oral (L1903) ; inhalation (L1903) ; dermal (L1903)
Toxicity Summary
Phthalate esters are endocrine disruptors. They decrease foetal testis testosterone production and reduce the expression of steroidogenic genes by decreasing mRNA expression. Some phthalates have also been shown to reduce the expression of insulin-like peptide 3 (insl3), an important hormone secreted by the Leydig cell necessary for development of the gubernacular ligament. Animal studies have shown that these effects disrupt reproductive development and can cause a number of malformations in affected young. (A2883)
Average Daily Intake
The average daily intake of diisobutyl phthalate as a result of exposure to house dust containing this compound, measured in residents of 9 cities in China and in Albany, NY; sampling was conducted from May to July 2010(1).;Table: Dust Ingestion and Dermal Adsorption (ng/kg-bw/day) [Table#5304]
The mean estimated daily intake of diisobutyl phthalate in residents for Central Taiwan were 0.26, 1.28, and 0.91 ug/kg-bw/day for pregnant women, children age 2 and age 5, respectively(1). The tolerable daily intake among Europeans has been set at 100 ug/kg body weight/day(2).
Ecotoxicity Excerpts
/AQUATIC SPECIES/ The effect of DIBP on reproduction rate in Daphnia magna (water flea) was examined in a 21 day experiment. NOEC = 1 mg/L; LOEC = 3 mg/L. An emulsifier was used for preparation of the stock.
/AQUATIC SPECIES/ Diisobutyl phthalate inhibited the growth of cells of the protozoa, tetrahymena pyriformis (strain W) completely at 50 ug/mL.
/PLANTS/ Radish (Raphanus sativus) seedlings were exposed to 160 to 180 ng/cu dm with an air flow of 3.0 cu dm/min over 2 wk/ Chlorosis occured rapidly, and the radishes died within ca 14 days.
/PLANTS/ No visible adverse effects were observed /in Sinapis alba L. (Yellow mustard)/ by administration of 2.5 ug/sq cm onto the surface of the leaves /for 15 days/. /Purity >99.5%/
/PLANTS/ Electron transport reactions at concentrations between 10 to 1000 mmol/cu m DIBP were measured using thylakoid membranes from spinach chloroplasts. The effects on full chain electron transport (coupled PS1+PS2), uncoupled electron transport, and phtosystem 1 (PS1) activity were determined. Couple PS1+PS2: 80% inhibition at 100-1000 mmol/cu m, 50% inhibition (I50) at 42 mmol/cu m; uncoupled: 60% inhibition at 100 to 1000 mmol/cu m, 50% inhibition (I50) at 87 mmol/cu m; PS1 activity: up to 1000 mmol/cu m only 40% inhibition.
法規制情報
Regulatory Information
Chemical: 1,2-Benzenedicarboxylic acid, bis(2-methylpropyl) ester
Hazard Traits - Carcinogenicity; Developmental Toxicity; Endocrine Toxicity; Immunotoxicity; Reproductive Toxicity; Respiratory Toxicity;Authoritative List - CECBP - Priority Chemicals; EC Annex VI CMRs - Cat. 1B; EC EDs;Report - if used as a fragrance or flavor ingredient
Regulation (EC) No 178/2002 (amended)
1,2-Benzenedicarboxylic acid, 1,2-bis(2-methylpropyl) ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,2-Benzenedicarboxylic acid, 1,2-bis(2-methylpropyl) 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: 30-08-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/13519;Status: Active Update: 22-07-2013 https://echa.europa.eu/registration-dossier/-/registered-dossier/1354;Status: Cease Manufacture Update: 15-09-2010 https://echa.europa.eu/registration-dossier/-/registered-dossier/1834;Status: Active Update: 12-11-2012 https://echa.europa.eu/registration-dossier/-/registered-dossier/1908;Status: Cease Manufacture Update: 03-01-2013 https://echa.europa.eu/registration-dossier/-/registered-dossier/7169;Status: Cease Manufacture Update: 11-02-2014 https://echa.europa.eu/registration-dossier/-/registered-dossier/1730
Restricted substance: Diisobutyl phthalate;EC: 201-553-2;Restriction condition document: PDF link
TSCA Requirements
Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. Effective date 09/29/06; Reporting date 11/28/06.
Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 1,2-Benzenedicarboxylic acid, bis(2-methylpropyl) ester is included on this list. Effective date 10/04/82; Sunset date 10/04/92.
安全データ
- 注意喚起語
- 危険
- 危険有害性情報
- コード 危険有害性情報 危険有害性クラス 区分 注意喚起語 シンボル P コード H410
化学と産業
薬理情報
Metabolism/Metabolites
Three genetically distinct carboxylesterases from rat liver ER and one from human liver have been identified as the most important xenobiotic-hydrolyzing esterases. Hydrolysis of DIBP by human and 2 of the rat liver esterases was minor in comparison to other phthalate esters. The activity decreased with increasing lipophilicity of the cmpd.
Phthalate esters are first hydrolyzed to their monoester derivative. Once formed, the monoester derivative can be further hydrolyzed in vivo to phthalic acid or conjugated to glucuronide, both of which can then be excreted. The terminal or next-to-last carbon atom in the monoester can also be oxidized to an alcohol, which can be excreted as is or first oxidized to an aldehyde, ketone, or carboxylic acid. The monoester and oxidative metabolites are excreted in the urine and faeces. (A2884)
Absorption, Distribution and Excretion
This study examined the extent of dermal absorption of a series of phthalate diesters in the rat. Those tested were dimethyl, diethyl, dibutyl, diisobutyl, dihexyl, di(2-ethylhexyl), diisodecyl, and benzyl butyl phthalate. Hair from a skin area (1.3 cm in diameter) on the back of male F344 rats was clipped, the (14)C-phthalate diester was applied in a dose of 157 mumol/kg, and the area of application was covered with a perforated cap. The rat was restrained and housed for 7 days in a metabolic cage that allowed separate collection of urine and feces. Urine and feces were collected every 24 hr, and the amount of (14)C excreted was taken as an index of the percutaneous absorption. At 24 hr, diethyl phthalate showed the greatest excretion (26%). As the length of the alkyl side chain increased, the amount of (14)C excreted in the first 24 hr decreased signficantly. The cumulative percentage dose excreted in 7 days was greatest for diethyl, dibutyl, and diisobutyl phthalate, about 50-60% of the applied (14)C; an intermediate (20-40%) for dimethyl, benzyl butyl, and dihexyl phthalate. Urine was the major route of excretion of all phthalate diesters except for diisodecyl phthalate. This compound was poorly absorbed and showed almost no urinary excretion. After 7 days, the percentage dose for each phthalate that remained in the body was minimal showed no specific tissue distribution. Most of the unexcreted dose remained in the area of application. These data show that the structure of the phthalate diester determines the degree of dermal absorption. Absorption maximized with diethyl phthalate and then decreased significantly as the alkyl side chain length increased.
用途と製造
Uses
Used as plasticizer; [Hawley] Used in paints, lacquers, and varnishes; Also used in the paper and pulp industry and to make boards, chemicals, polymers, adhesives, softeners, and viscosity adjusters; [IUCLID]
Pulp and Paper Processing [Category: Industry];Painting (Pigments, Binders, and Biocides) [Category: Paint];Working with Glues and Adhesives [Category: Other]
... Used in many PVC formulations, principally for ease of gelation.
Paints, lacquers and varnishes industry ... paper, pulp and board industry ... adhesive, binding agents ... softeners ... viscosity adjusters ... plastificante ...
... /DiBP/ has been used as a plasticizer for nitrocellulose (lowest cost plasticizer for cellulose nitrate), cellulose ether, and polyacrylate and polyacetate dispersions. It is used in nail polish, cosmetics, lubricants, floor carpets, tapestry, clothing treatments, rubber dentistry settings, as a fuel stabilizer, in leather varnishes and lacquers, as a concrete additive, as an adjusting agent for lead chromate paint pigments, explosive material, lacquer manufacturing, and methyl methacrylate applications. DiBP is also used in printing inks for paper and packaging. Because DiBP has similar properties as dibutyl phthalate (DBP), it can be used as a substitute for DBP.
In Australia, DiBP is imported for use a plasticizer in the manufacture of PVC and rubber and as a component of industrial adhesives and catalyst systems for polypropylene and fiberglass manufacture. It is also sold in Australia to various institutions and laboratories for research and product development.
U.S. Production
2023: 250,000 - <400,000 lb;2022: 250,000 - <400,000 lb;2021: 250,000 - <400,000 lb;2020: 550,000 - <700,000 lb
1,2-Benzenedicarboxylic acid, bis(2-methylpropyl) ester is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).
Production volumes for non-confidential chemicals reported under the Inventory Update Rule.[Table#5308]
Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: 1,2-Benzenedicarboxylic acid, 1,2-bis(2-methylpropyl) ester. Aggregated National Production Volume: 500,000 to < 1 million pounds.
Methods of Manufacturing
... DiBP is manufactured commercially in a closed system by catalytically esterifying phthalic anhydride with n-butyl alcohols (isobutanol). As with other phthalates, the unreacted alcohols are recovered and reused, and the DiBP mixture is purified by vacuum distillation or activated charcoal. The purity of DiBP can achieve 99% or greater using current manufacturing processes. The remaining fraction of DiBP may contain a maximum of 0.1% water.
The first step, alcoholysis of phthalic anhydride (PA) to give the monoester, is rapid and goes to completion. The reaction generally starts at elevated temperatures and proceeds exothermically. The second step is the conversion of the monoester to a diester with the formation of water. This is a reversible reaction and proceeds more slowly than the first, thus determining the overall rate of reaction. To shift the equilibrium towards the diester, the water of reaction is removed by distillation. The rate of reaction can be influenced by the choice of catalyst and the reaction temperature. For fast conversion rates, high reaction temperatures are generally used. However, these are influenced by the boiling point of the alcohol and/or the type of catalyst. ... Currently, nearly all major phthalate producers use amphoteric catalysts for the esterification of high boiling alcohols. ... The reaction temperatures for the amphoteric catalysts are about 200 °C. At this temperature side reactions are minimized, and the alcohol can be recycled without purification. By using this type of catalyst, over 99.5 % conversion to diester can be achieved. /Phthalates/
Formulations/Preparations
The water based adhesive may contain typically up to 15% DIBP. ...
Trade Name: Uniplex 155
General Manufacturing Information
Adhesive Manufacturing;Paint and Coating Manufacturing;Rubber Product Manufacturing
1,2-Benzenedicarboxylic acid, 1,2-bis(2-methylpropyl) ester: ACTIVE
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