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Home > Encyclopedia > Dibutyl sebacate

Dibutyl sebacate

pharmaceutical raw materials
Dibutyl sebacate structure

Dibutyl sebacate 

structure
  • CAS No:

    109-43-3

  • Formula:

    C18H34O4

  • Chemical Name:

    Dibutyl sebacate

  • Synonyms:

    Decanedioic acid,1,10-dibutyl ester;Sebacic acid,dibutyl ester;Decanedioic acid,dibutyl ester;PX 404;Bis(n-butyl) sebacate;Dibutyl sebacate;Polycizer DBS;Staflex DBS;Kodaflex DBS;Di-n-Butyl sebacate;Ergoplast SDB;Dibutyl decanedioate;Sebacic acid di-n-butyl ester;Uniflex DBS;DBS;Reomol DBS;NSC 3893;98781-27-2;39393-66-3

  • Categories:

    Cosmetic Ingredient  >  Film Forming

Description

Dibutyl sebacate (Dibutyl decanedioate) is a dibutyl ester of sebacic acid, mainly used as a plasticizer in production of plastics[1].


Liquid|COLOURLESS OILY LIQUID.|colourless to oily liquid; fruity but very mild odour with a very faint fruity oily taste


Dibutyl decanedioate is a fatty acid ester.

Dibutyl sebacate Basic Attributes

314.46000

314.46

203-672-5

4W5IH7FLNY

1349

3893

DTXSID1041847

Colorless liquid

2917131000

Characteristics

52.60000

5.3

Liquid

0.9405 g/cm3 @ Temp: 15 °C

-10 °C

344.5 °C

>230 °F

n20/D 1.441(lit.)

hexane, toluene, ethanol and acetone: soluble

4.69X10-6 mm Hg @ 25 deg C

Relative vapour density (air = 1): 10.8

Odorless

183.89 Ų [M+H]+

690 °F (365 °C)

Safety Information

NONH for all modes of transport

3

R40; R36/37/38

S36/37; S36; S26

VS1150000

Xn; Xi

Well closed.

P261-P305 + P351 + P338

H315-H319-H335

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Combustible liquid when exposed to heat or flame; can react with oxidizing materials.

Dibutyl sebacate is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and 2) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part.|Dibutyl sebacate is an indirect food additive for use only as a component of adhesives.|Prior-Sanctioned Food Ingredients: Substances classified as plasticizers, when migrating from food-packaging material shall include: dibutyl sebacate.

Combustible.

|Warning|H315 (98.57%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 469 companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

...CARBON DIOXIDE, DRY CHEM.

Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Collect leaking and spilled liquid in sealable containers as far as possible. Carefully collect remainder. Then store and dispose of according to local regulations.

Well closed.

A harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C; on spraying or dispersing, however, much faster.

Repeated or prolonged contact may cause skin sensitization.

NO open flames.

STRICT HYGIENE!

Use ventilation.

Protective gloves. Protective clothing.

Wear safety goggles.

| 0 - Materials that, under emergency conditions, would offer no hazard beyond that of ordinary combustible materials.| 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.

Toxicity

Mildly toxic by ingestion. Experimental reproductive effects.

LD50 Rat oral 16-32 g/kg|LD50 Rat oral 16.0 g/kg|LD50 Rat oral 16 g/kg

NOT REPORTED FOUND IN NATURE.

Dibutyl sebacate's production and use as a plasticizer, rubber softener, flavoring agent and cosmetic and perfume ingredient(1) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 575(SRC), determined from a water solubility of 40 mg/l(2) and a regression-derived equation(3), indicates that dibutyl sebacate is expected to have low mobility in soil(SRC). Volatilization of dibutyl sebacate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.8X10-8 atm-cu m/mole(SRC), calculated from a vapor pressure of 4.7X10-6 mm Hg(4) and water solubility of 40 mg/l(2). Dibutyl sebacate is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Dibutyl sebacate and other plasticizers were readily biodegraded by pure bacterial and fungal cultures(5,6).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 575(SRC), determined from a water solubility of 40 mg/l(2) and a regression-derived equation(3), indicates that dibutyl sebacate is expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is not expected to be an important fate process(3) based upon an estimated Henry's Law constant of 4.8X10-8 atm-cu m/mole(SRC), calculated from a vapor pressure of 4.7X10-6 mm Hg(4) and water solubility of 40 mg/l(2). A base-catalyzed second-order hydrolysis rate constant of 0.05 L/mole-sec(SRC) was estimated using a structure estimation method(5); this corresponds to half-lives of 4.5 years and 166 days at pH values of 7 and 8, respectively(5). Dibutyl sebacate and other plasticizers were readily biodegraded by pure bacterial and fungal cultures(6,7). According to a classification scheme(8),an estimated BCF of 77(SRC), from its water solubility(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dibutyl sebacate, which has a vapor pressure of 4.7X10-6 mm Hg at 25 °C(2), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase dibutyl sebacate 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 21 hours(SRC), calculated from its estimated rate constant of 1.8X10-11 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3). Particulate-phase dibutyl sebacate may be removed from the air by wet and dry deposition(SRC). Dibutyl sebacate may also undergo direct photolysis in the environment since this compound contains functional groups that can absorb light greater than 290 nm(4).

The rate constant for the vapor-phase reaction of dibutyl sebacate with photochemically-produced hydroxyl radicals has been estimated as 1.8X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 21 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). A base-catalyzed second-order hydrolysis rate constant of 0.05 L/mole-sec(SRC) was estimated using a structure estimation method(2); this corresponds to half-lives of 4.5 years and 166 days at pH values of 7 and 8, respectively(2). The expected hydrolysis products are butanol and sebacic acid. Dibutyl sebacate may also undergo direct photolysis in the environment since this compound contain a functional group that can absorb light greater than 290 nm(3).

An estimated BCF of 77 was calculated for dibutyl sebacate(SRC), using a water solubility of 40 mg/l(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

The Koc of dibutyl sebacate is estimated as 575(SRC), using a water solubility of 40 mg/l(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that dibutyl sebacate is expected to have low mobility in soil(SRC).

The Henry's Law constant for dibutyl sebacate is estimated as 4.8X10-8 atm-cu m/mole(SRC) from its vapor pressure, 4.7X10-6 mm Hg(1), and water solubility, 40 mg/l(2). This Henry's Law constant indicates that dibutyl sebacate is expected to be essentially nonvolatile from water surfaces(3). Dibutyl sebacate's estimated Henry's Law constant(1,2) indicates that volatilization from moist soil surfaces is not expected to be an important environmental fate process(SRC). Volatilization from dry soil surfaces is not expected to be an important fate process(SRC) based on the vapor pressure of this compound(1).

Dibutyl sebacate was identified, not quantified, in drinking water from the US(1).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 4,826 workers (2,128 of these are female) are potentially exposed to dibutyl sebacate in the US(1). Occupational exposure to dibutyl sebacate may occur through inhalation and dermal contact with this compound at workplaces where dibutyl sebacate is produced or used(SRC). The general population is exposed to dibutyl sebacate through the use of consumer products that contain this compound(SRC).

Drug Information

IN VITRO PANCREATIC LIPASE HYDROLYZES DIBUTYL SEBACATE AS RAPIDLY AS IT DOES TRIOLEIN, & FROM THIS IT CAN BE CONCLUDED THAT THE PLASTICIZER IS METABOLIZED IN THE BODY BY SAME ROUTE AS FATS.

Fresh air, rest.


Remove contaminated clothes. 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.

dibutyl sebacate

Dibutyl sebacate Use and Manufacturing

Methods of Manufacturing

BY DISTILLATION OF SEBACIC ACID WITH BUTYL ALCOHOL IN PRESENCE OF CONCN HCL IN BENZENE SOLN OR BY REACTING BUTYL ALCOHOL & SEBACYL CHLORIDE...

Uses

Synthetic flavoring adjuvant.


Pigments


Ink, toner, and colorant products

Production

500,000 - 1,000,000 lb|(1972) 2.04X10+9 GRAMS|(1975) 2.54X10+9 G (INCL 2-ETHYLHEXYL)

Pharmaceutical and medicine manufacturing|Decanedioic acid, 1,10-dibutyl ester: ACTIVE|REPORTED USES: NON-ALCOHOLIC BEVERAGES 1.0-5.0; ICE CREAM, ICES, ETC 2.0-5.0 PPM; CANDY 15 PPM; BAKED GOODS 15 PPM.|DIBUTYL SEBACATE IS A VERY GOOD PLASTICIZER FOR POLYVINYL CHLORIDE, TO WHICH IT IMPARTS EXCELLENT LOW-TEMPERATURE RESISTANCE, FLEXIBILITY BEING RETAINED OVER WIDE TEMP RANGE.|IT IS...PLASTICIZER OF CHOICE FOR CELLULOSE ACETOBUTYRATE, POLYVINYL BUTYRAL, RUBBER HYDROCHLORIDE, & POLYVINYLIDENE CHLORIDE. IT IS EQUALLY COMPATIBLE WITH NITROCELLULOSE, ETHYL CELLULOSE, POLYSTYRENE, & MANY SYNTHETIC RUBBERS.|...ITS USE IN FOOD-PACKAGING INDUSTRY IS AUTHORIZED IN FRANCE, US, & ITALY.

DIBUTYL SEBACATE, ADDITIVE IN PVDC FILM, WAS EXTRACTED BY SOLVENTS IN FATTY FOODS & DETERMINED BY GAS CHROMATOGRAPHY.|GAS-CHROMATOGRAPHIC DETERMINATION OF DIBUTYL SEBACATE IN AIR OF INDUSTRIAL PREMISES.

EPA Safer Chemical Functional Use Classes -> Emollients;Skin Conditioning Agents;Solvents|Safer Chemical Classes -> Green circle - The chemical has been verified to be of low concern|Food additives -> Flavoring Agents|Flavouring Agent -> FLAVOURING_AGENT; -> JECFA Functional Classes|Flavoring Agents -> JECFA Flavorings Index|Cosmetics -> Emollient; Film forming; Hair conditioning; Plasticiser; Skin conditioning

Flavoring Agents|Flavouring Agent -> FLAVOURING_AGENT;

Computed Properties

Molecular Weight:314.5
XLogP3:5.3
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:17
Exact Mass:314.24570956
Monoisotopic Mass:314.24570956
Topological Polar Surface Area:52.6
Heavy Atom Count:22
Complexity:248
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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