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Butyl phthalyl butyl glycolate

HCID 6819
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
85-70-1
Standard SMILES
CCCCOC(=O)COC(=O)c1ccccc1C(=O)OCCCC
InChIKey
GOJCZVPJCKEBQV-UHFFFAOYSA-N
Molecular formula
C18H24O6
Average molar mass
336.4 g/mol
Monoisotopic mass
336.15728848

Overview

Butyl phthalyl butylglycolate is a benzoate ester.

Names & identifiers

Preferred name
Butyl phthalyl butyl glycolate
IUPAC
2-O-(2-butoxy-2-oxoethyl) 1-O-butyl benzene-1,2-dicarboxylate
English name
Butyl phthalyl butyl glycolate
Molecular formula
C18H24O6
Molecular weight
336.38

Names & synonyms

Butyl phthalyl butyl glycolate85-70-1Butoxycarbonylmethyl butyl phthalateReomol 4pgButyl carbobutoxymethyl phthalateButyl glycolyl butyl phthalateButyl phthalate butyl glycolate2-butoxy-2-oxoethyl butyl phthalateButylphthalyl butylglycolateDibutyl o-carboxybenzoyloxyacetateSanticizer B 16Morflex 190
Show more names
BPBGButyl phthalyl butyl glycollateN-BUTYL PHTHALYL N-BUTYL GLYCOLATEDIBUTYL O-(O-CARBOXYBENZOYL)GLYCOLATEreomol4pgBPBG STANDARDsanticizerb16santicizerb-16
Glycolic acid, butyl ester, butyl phthalateButylcarbobutoxymethyl phthalatePhthalic acid, butyl ester, ester with butyl glycolateDTXSID7023938Glycolic acid, phthalate, dibutyl ester1,2-Benzenedicarboxylic acid, 2-butoxy-2-oxoethyl butyl esterPhthalic acid, butyl ester, butyl glycolateAI3-01793 (USDA)

Database identifiers

CAS

Properties

Computed structural properties

XLogP
4.6
Topological polar surface area
78.9 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
6
Rotatable bonds
13
Heavy atoms
24
Formal charge
0
Complexity
406

Experimental & physicochemical properties

PolymersPlastics & Rubber -> Phthalate Esters
CosmeticsFilm forming
SpringerMaterials PropertiesViscosity
PesticidesPesticide -> EPA IRIS
OdorODORLESS
TasteTASTELESS
Density1.097
Color/FormCOLORLESS LIQUID
SolubilityPhthalate esters are soluble to various extents in many common organic solvents and oils, but have a relatively low solubility in water. /Phthalate esters/
Flash Point390 °F (199 °C) (Open cup)
Endocrine DisruptorsPotential endocrine disrupting compound

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 3 items

H413 (100%): May cause long lasting harmful effects to aquatic life [Hazardous to the aquatic environment, long-term hazard]

P273, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Regulatory Information · 3 items

Chemical: 1,2-Benzenedicarboxylic acid, 2-butoxy-2-oxoethyl butyl ester

Regulation (EC) No 178/2002 (amended)

1,2-Benzenedicarboxylic acid, 2-butoxy-2-oxoethyl butyl 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.

Fire PotentialSLIGHT, WHEN EXPOSED TO HEAT OR FLAME; CAN REACT WITH OXIDIZING MATERIALS.
Hazards Summary · 1 item

Like dioctyl phthalate, it may cause CNS depression and mild liver toxicity after ingestion of large amounts; [HSDB] A mild eye irritant, based on animal studies; Targets kidneys, CNS, male reproductive system, and eyes; [MSDSonline] See PHTHALATE ESTERS.

FDA Requirements · 2 items

Butylphthalate butyl glycolate is an indirect food additive for use only as a component of adhesives.

Butylphthalyl butyl glycolate is classified as a plasticizer, when migrating from food-packaging material.

Special Reports · 3 items

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)

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

BUTYLGLYCOLYLBUTYL PHTHALATE OR DIISOOCYTL PHTHALATE WAS ADMIN IN DIET TO MALE SPRAGUE DAWLEY RATS, BEAGLE DOGS & MINIATURE PIGS IN DOSE OF 50 MG/KG FOR 21-28 DAYS BEFORE ORAL ADMIN OF SINGLE DOSE OF SAME CMPD LABELED WITH (14)C IN CARBONYL GROUP. DIISOOCYTL PHTHALATE WAS LESS READILY METABOLIZED THAN BUTYLGLYCOLYL BUTYL PHTHALATE BY ALL SPECIES.

Absorption, Distribution and Excretion · 1 item

BUTYLGLYCOLYLBUTYL PHTHALATE WAS ADMIN IN DIET TO MALE SPRAGUE DAWLEY RATS, BEAGLE DOGS & MINIATURE PIGS IN DOSE OF 50 MG/KG FOR 21-28 DAYS BEFORE ORAL ADMIN OF SINGLE DOSE OF SAME CMPD LABELED WITH (14)C IN CARBONYL GROUP. IT WAS EXCRETED MAINLY IN THE URINE IN RATS (77-83%), DOGS (72-75%) AND PIGS (68-89%).

Uses & manufacturing

Uses · 3 items

Used as a plasticizer for polyvinyl chloride; [HSDB]

Plasticizer for polyvinyl chloride. FDA approved for use in vinyl food wrappings.

It is used for making a variety of packaging films.

U.S. ProductionProduction volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#978]
Use ClassificationCosmetics -> Film forming
General Manufacturing Information · 3 items

1,2-Benzenedicarboxylic acid, 1-(2-butoxy-2-oxoethyl) 2-butyl ester: ACTIVE

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/

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
85-70-1
PubChem CID
6819
DTXSID
DTXSID7023938
ChEMBL
CHEMBL3182027
ChEBI
CHEBI:191079
UNII
I5LOD5H050
EC Number
201-624-8
Nikkaji
J4.378H
Boiling Point
345 °C

Physicochemical properties

Melting point
25 °C · 25°C
Boiling point
220 °C · 220 °C (10 mmHg)
Density
1.1 · 1.1
refractive index
20 · n20/D 1.49(lit.)
Flash point
199 °C · 199 °C
storage temp.
-20 °C · Hygroscopic, -20°C Freezer, Under inert atmosphere
solubility
Chloroform (Sparingly), Methanol (Slightly)
form
Oil
color
Colourless
Specific Gravity
1.1 · 1.1
Odor
100 % · at 100.00%. odorless
Water Solubility
12 mg/L · 12mg/L(20 ºC)
Henry's Law Constant
4.7 · 4.7×102 mol/(m3Pa) at 25℃, HSDB (2015)
Cosmetics Ingredients Functions
PLASTICISERFILM FORMING
LogP
4.253 · 4.253 (est)
Indirect Additives used in Food Contact Substances
BUTYL PHTHALYL BUTYL GLYCOLATE
CAS DataBase Reference
85 · 85-70-1(CAS DataBase Reference)
FDA 21 CFR
181.27 · 181.27
EWG's Food Scores
1 · 1
FDA UNII
5 LOD5H050 · I5LOD5H050
EPA Substance Registry System
2 · 2-Butoxy-2-oxoethyl butyl phthalate (85-70-1)
Hazard statements
413 · H413
Hazard Codes
N-T
Risk Statements
62 · 62-61-51
Safety Statements
61 · 61-53-45
RTECS
535000 · TI0535000
TSCA
TSCA listed
HS Code
29173490 · 29173490
Hazardous Substances Data
85 · 85-70-1(Hazardous Substances Data)
TSCA Requirements · 1 item

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, 2-butoxy-2-oxyethyl butyl ester is included on this list. Effective date 10/04/82; Sunset date 1/13/86.

NFPA Hazard Classification · 3 items

1 - Materials that, under emergency conditions, can cause significant irritation.

1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.

0 - Materials that in themselves are normally stable, even under fire conditions.

Hazard Classes and CategoriesAquatic Chronic 4 (100%)
State Drinking Water Guidelines · 2 items

(MN) MINNESOTA 7000 ug/L

(FL) FLORIDA 7,000

Safety & protection

Fire Fighting ProceduresWater or foam may cause frothing.
Disposal Methods · 1 item

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 · 1 item

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.

Toxicology

Body BurdenButyl glycolyl butyl phthalate was identified, not quantified, in the adipose tissue in 6 of 46(1) and 8 of 46(2) humans sampled in the US.
InteractionsMICE INJECTED IP WITH 60 MG/KG HEXOBARBITAL, 30 MIN AFTER PRETREATMENT WITH 500 MG/KG BUTYLGLYCOLYL BUTYL PHTHALATE SHOWED AN INCR HEXOBARBITAL INDUCED SLEEPING TIME, WHILE MICE TREATED WITH 250 MG/KG BUTYLGLYCOLYL BUTYL PHTHALATE DID NOT.
Ecotoxicity Values · 3 items

LC50; Species: Oryzias latipes (Medaka, high-eyes); Conditions: freshwater, static, 10 °C; Concentration: 34000 ug/L for 24 or 48 hr

LC50; Species: Oryzias latipes (Medaka, high-eyes); Conditions: freshwater, static, 20 °C; Concentration: 17500 ug/L for 24 or 48 hr

LC50; Species: Oryzias latipes (Medaka, high-eyes); Conditions: freshwater, static, 30 °C; Concentration: 17500 ug/L for 24 or 48 hr

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1.5X10+4(SRC), determined from a structure estimation method(2), indicates that butyl glycolyl butyl phthalate is expected to be immobile in soil(SRC). Volatilization of butyl glycolyl butyl phthalate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.1X10-8 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Butyl glycolyl butyl phthalate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 7.1X10-6 mm Hg(SRC), determined from a fragment constant method(4). Rates of 84.5 to >99% biodegradation in 24 hrs using a semi-continuous activated sludge test(5) suggests that biodegradation may be an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1.5X10+4(SRC), determined from a structure estimation method(2), indicates that butyl glycolyl butyl phthalate is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.1X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 300(SRC), from an estimated log Kow of 4.15(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is high(SRC). However, bioconcentration studies on compounds which are structurally similar suggest that bioconcentration may be lower than that indicated by the regression-derived equations due to the ability of aquatic organisms to readily metabolize this class of compounds(8). Hydrolysis is expected to be an important process(SRC) based on estimated hydrolysis half-lives of 11 and 1 days at pHs 7 and 8, respectively(9). A 95% biodegradation in 2 days using the river die-away test(10) suggests 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), butyl glycolyl butyl phthalate, which has an estimated vapor pressure of 7.1X10-6 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase butyl glycolyl butyl 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 40 hours(SRC), calculated from its rate constant of 9.7X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase butyl glycolyl butyl phthalate may be removed from the air by wet or dry deposition(SRC). Butyl glycolyl butyl phthalate does contain chromophores that absorb at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Ecotoxicity Excerpts · 1 item

/AQUATIC SPECIES/ The study was conducted to determine the effects of treatment and seawater dilution of municipal wastewater on marine organisms. An experimental facility was built in southeast Florida that provided both unchlorinated and chlorinated effluent from three standard treatments: primary settling, chemical flocculation, and activated sludge secondary treatment. Exposure tests lasting longer than one month were conducted on the sheepshead minnow (Cyprinodon variegatus) and the pink shrimp (Penaeus duorarum), with each of these six effluent types at seawater dilution ratios of 30:1, 100:1, and 300:1. The shrimp showed a much more sensitive response than the minnow. Almost 100% mortality occurred for shrimp exposed to the unchlorinated 30:1 seawater dilutions of primary-settled wastewater, while mortality for the other two effluents were similar to controls. Mortality could not be attributed to any of the chemicals measured in the wastewater. For the 30:1 dilution experiments, chlorination usually resulted in much higher toxicity; increasing the dilution factor from 30:1 to 100:1 reduced the mortality observed (in both unchlorinated and chlorinated tests) essentially to control levels. Little bioaccumulation of metals or chlorinated organics in exposed specimens.

Effluent ConcentrationsButyl glycolyl butyl phthalate was identified in the fly ash from combined coal/refuse combustion(1).
EPA IRIS Information · 2 items

Butylphthalyl butylglycolate (BPBG)

1 mg/kg-day

Soil Adsorption/Mobility · 1 item

Using a structure estimation method based on molecular connectivity indices(1), the Koc of butyl glycolyl butyl phthalate can be estimated to be 1.5X10+4(SRC). According to a classification scheme(2), this estimated Koc value suggests that butyl glycolyl butyl phthalate is expected to be immobile in soil.

Atmospheric ConcentrationsSOURCE DOMINATED: Butyl glycolyl butyl phthalate was detected in the air at a Hamilton, Ontario, water works plant located adjacent to a municipal incinerator, at a concentration of 750 ng/cu m(1).
Human Toxicity Excerpts · 1 item

/ALTERNATIVE and IN VITRO TESTS/ Comparative toxicity of phthalate esters to HeLa-S3 cells was studied by determining their effect on doubling time of the cells. The toxicity of the esters decreasing in order: diethyl phthalate, butylphthalyl butyl glycolate, di-iso-butyl phthalate, ethyl phthalyl ethyl glycolate, bis(2-ethylhexyl) phthalate, dimethyl isophthalate, dibutyl phthalate, methyl phthalyl ethyl glycolate, dimethyl phthalate, and dioctyl phthalate.

Artificial Pollution SourcesButyl glycolyl butyl phthalate's production and use as a plasticizer(1) may result in its release to the environment through various waste streams(SRC).

Regulatory information

FDA Requirements · 2 items

Butylphthalate butyl glycolate is an indirect food additive for use only as a component of adhesives.

Butylphthalyl butyl glycolate is classified as a plasticizer, when migrating from food-packaging material.

TSCA Requirements · 1 item

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, 2-butoxy-2-oxyethyl butyl ester is included on this list. Effective date 10/04/82; Sunset date 1/13/86.

State Drinking Water Guidelines · 2 items

(MN) MINNESOTA 7000 ug/L

(FL) FLORIDA 7,000

Safety data

tsca
TSCA listed
rtecs
TI0535000
hs_code
29173490
risk_code
62-61-51
hazard_code
N-T
safety_code
61-53-45
Hazard statements
H413
Hazardous Substances Data
85-70-1(Hazardous Substances Data)

IT IS COMPATIBLE WITH POLYVINYL CHLORIDE, POLYVINYL ACETATE, ETHYL CELLULOSE, & NITRILE RUBBER, & IS USED FOR MAKING A VARIETY OF PACKAGING FILMS, TO WHICH IT IMPARTS VERY GOOD STABILITY TO HEAT & LIGHT.

Applications

UsesButyl phthalyl butyl glycolate is used as a plasticizer for polyvinylchloride. It isusedformaking avarietyofpackaging films because it imparts very good stability to heat and light.

UsesVinyl.

Upstream & downstream products

Upstream raw materials

Butyl 2-chloroacetate

Suppliers36 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖北万得化工有限公司15377098680 15377098680 · [email protected]
Hebei Chuanghai Biotechnology Co., Ltd+86-17732866630 · [email protected]
Hebei Zhuanglai Chemical Trading Co Ltd+86-16264648883 · [email protected]
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]
爱斯特(成都)生物制药股份有限公司+86-28-85122536 85324413 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
玛雅试剂+86 (573) 82222445 (0)18006601000 452520369 · [email protected]
赛默飞世尔科技(中国)有限公司800-810-5118 · [email protected]
上海遐瑞医药科技有限公司+86 21 61551611
TCI AMERICA800-4238616 · [email protected]
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
TCI Europe320-37350700 · [email protected]
九鼎化学(上海)科技有限公司4009209199 · [email protected]
艾吉析科技(上海)有限公司17717235263 17717235263 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]
湖北齐飞医药化工有限公司027-59322506 18071128681 · [email protected]
上海思域化工科技有限公司021-34053660 · [email protected]
武汉卡诺斯科技有限公司18064039730 · [email protected]
BOC Sciences[email protected]
上海贤鼎生物科技有限公司021-021-52271985 17721149837 · [email protected]
Shaanxi Didu New Materials Co. Ltd+86-86-17392712779 +86-13289823923 · [email protected]
上海臻励生物科技有限公司021-16621358918; 18516310516;16621358918;13045646768 · [email protected]
上海易恩化学技术有限公司400-400-1332688 18019345275 · [email protected]
厦门盈融达化工有限公司+86-0592-6210733 · [email protected]
career henan chemical co+86-0371-86658258 · [email protected]
TCI Chemicals (India) Pvt. Ltd.[email protected]
Aladdin Scientific[email protected]
上海安谱实验科技股份有限公司18502138905 · [email protected]
山东天铭生物科技发展有限责任公司400-9019001 400-901-9001
广东翁江化学试剂有限公司0751-2815983 13927872582 · [email protected]
北京百灵威科技有限公司18210857532 18210857532 · [email protected]
湖北实顺生物科技有限公司027-59223025 15107168801 · [email protected]

Additional notes

DefinitionChEBI: Butyl phthalyl butylglycolate is a benzoate ester.