109-43-3

Basic information

• Product Name: Dibutyl sebacate
• Synonyms: Dibutyl sebacinate;dibutyl1,8-octanedicarboxylate;Dibutylester kyseliny sebakove;dibutylesterkyselinysebakove;Kodaflex DBS;kodaflexdbs;Monoplex dbs;monoplexdbs
• CAS NO: 109-43-3
• Molecular Formula: C₁₈H₃₄O₄
• Molecular Weight: 314.46
• EINECS: 207-395-0
• Product Categories: pharmacetical;Piperazine derivates;Fatty Acid Esters (Plasticizer);Functional Materials;Plasticizer
• Mol File: 109-43-3.mol
• Article Data: 20

Chemical Properties

• Melting Point: 205 °C (dec.)(lit.)
• Boiling Point: 178-179 °C3 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear/Liquid
• Density: 0.94
• Vapor Pressure: 4.14E-05mmHg at 25°C
• Refractive Index: n20/D 1.441(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: hexane, toluene, ethanol and acetone: soluble
• Water Solubility: 50mg/L(temperature not stated)
• BRN: 1798308
• CAS DataBase Reference: Dibutyl sebacate(CAS DataBase Reference)
• NIST Chemistry Reference: Dibutyl sebacate(109-43-3)
• EPA Substance Registry System: Dibutyl sebacate(109-43-3)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 40-36/37/38
• Safety Statements: 36/37-36-26
• WGK Germany: 3
• RTECS: VS1150000
• TSCA: Yes
• Hazardous Substances Data: 109-43-3(Hazardous Substances Data)

Usage

Chemical Properties

clear liquid

Chemical Properties

Dibutyl sebacate is a clear, colorless, oily liquid with a bland to slight butyl odor.

Uses

Dibutyl sebacate (DBS) is a dibutyl ester of sebacic acid. Dibutyl sebacate can be used for plastics in use in the food packaging industry, in plastics used for medical devices, and for pharmaceutical applications. Dibutyl sebacate is also used as a desensitizer in Otto fuel II, a torpedo monopropellant.

Uses

Dibutyl sebacate has been used as a plasticizer to prepare free ethylcellulose films. It can be utilized as a core in liquid-core capsules with cross-linked alginate/polyacrylamide membrane prepared via co-extrusion jet-break-up method for the extraction of the pesticide, atrazine.

Production Methods

Dibutyl sebacate is manufactured by the esterification of n-butanol and sebacic acid in the presence of a suitable catalyst, and by the distillation of sebacic acid with n-butanol in the presence of concentrated acid.

Preparation

By distillation of sebacic acid with butyl alcohol in the presence of concentrated HCl in benzene solution or by reacting butyl alcohol and sebacyl chloride

General Description

Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards. Dibutyl sebacate is a commonly used plasticizer, which can be synthesized by the reaction of butyl alcohol and sebacyl chloride or by the distillation of sebacic acid with butyl alcohol in the presence of concentrated hydrochloric acid in benzene solution.

Flammability and Explosibility

Nonflammable

Pharmaceutical Applications

Dibutyl sebacate is used in oral pharmaceutical formulations as a plasticizer for film coatings on tablets, beads, and granules, at concentrations of 10–30% by weight of polymer. It is also used as a plasticizer in controlled-release tablets and microcapsule preparations. Dibutyl sebacate is also used as a synthetic flavor and flavor adjuvant in food products;for example,up to 5ppm is used in ice cream and nonalcoholic beverages.

Safety Profile

Mddly toxic by ingestion. Experimental reproductive effects. Combustible liquid when exposed to heat or flame; can react with oxidzing materials. To fight fire, use CO2 position it emits acrid smoke and fumes. See also ESTERS and n-BUTYL. ALCOHOL.

Safety

Dibutyl sebacate is used in cosmetics, foods, and oral pharmaceutical formulations, and is generally regarded as a nontoxic and nonirritant material. Following oral administration, dibutyl sebacate is metabolized in the same way as fats. In humans, direct eye contact and prolonged or repeated contact with the skin may cause very mild irritation. Acute animal toxicity tests and long-term animal feeding studies have shown no serious adverse effects to be associated with orally administered dibutyl sebacate.LD50 (rat, oral): 16g/kg

storage

Dibutyl sebacate should be stored in a closed container in a cool, dry location. Dibutyl sebacate is stable under the recommended storage conditions and as used in specified applications under most conditions ofuse.Asanester,dibutylsebacatemayhydrolyzeinthe presence of water at high or low pH conditions.

Incompatibilities

Dibutyl sebacate is incompatible with strong oxidizing materials and strong alkalis.

Regulatory Status

Included in the FDA Inactive Ingredients Database (oral capsules, granules, film-coated, sustained action, and tablets). Included in the Canadian List of Acceptable Non-medicinal Ingredients.

Synthetic route

1,10-decanedioic acid (111-20-6) + butan-1-ol (71-36-3) → dibutyl sebacate (109-43-3)

Conditions	Yield
With triflic acid on silica-encapsulated superparamagnetic iron oxide nanoparticles In neat (no solvent) at 90℃; for 0.25h; Catalytic behavior; Time; Reagent/catalyst; Flow reactor; Green chemistry;	96%
With Candida antarctica lipase B In cyclohexane at 45℃; for 6h;	80%
With hydrogenchloride; benzene

1,10-decanedioic acid (111-20-6) + n-butyl formate (592-84-7) → Decanedioic acid monobutyl ester (5278-98-8) + dibutyl sebacate (109-43-3)

Conditions	Yield
With Dowex 50W-X2 (50-100 mesh) In octane at 100℃; for 4.33333h;	A 93% B 4%
With Dowex 50Wx2 In octane at 100℃; for 4.33333h; Esterification;	A 93% B 4%

sebacoyl chloride (111-19-3) + butan-1-ol (71-36-3) → dibutyl sebacate (109-43-3)

1-bromo-butane (109-65-9) + 1,10-decanedioic acid (111-20-6) → Decanedioic acid monobutyl ester (5278-98-8) + dibutyl sebacate (109-43-3)

Conditions	Yield
With sodium hydroxide; Aliquat 336 In toluene for 24h; Heating;

scrap tire → pyrene (129-00-0) + dibutyl sebacate (109-43-3) + 1,3-diphenylbenzene (92-06-8) + 2-benzylnaphthalene (613-59-2)

Conditions	Yield
With air at 650 - 850℃; Oxidation; Formation of xenobiotics; Further byproducts given. Title compound not separated from byproducts;

octa-1,3-diene (1002-33-1) + carbon monoxide (201230-82-2) + butan-1-ol (71-36-3) → dibutyl sebacate (109-43-3)

Conditions	Yield
With palladium(II) trifluoroacetate; HeMaRaphos; toluene-4-sulfonic acid In toluene at 120℃; under 30003 Torr; for 24h; regioselective reaction;

dibutyl sebacate (109-43-3) → 1,10-decanedioic acid (111-20-6) + Decanedioic acid monobutyl ester (5278-98-8)

Conditions	Yield
With diethyl ether; water; sodium butanolate

dibutyl sebacate (109-43-3) → hexachloroethane (67-72-1)

Conditions	Yield
bei der Chlorierung im Sonnenlicht;

dibutyl sebacate (109-43-3) + BIGUANIDE (56-03-1) → 6,6'-octane-1,8-diyl-bis-[1,3,5]triazine-2,4-diamine (4128-90-9)

dibutyl sebacate (109-43-3) + benzyl alcohol (100-51-6) → decanedioic acid benzyl ester-butyl ester (22288-36-4)

Conditions	Yield
With sodium methylate

dibutyl sebacate (109-43-3) + toluene (108-88-3) + butan-1-ol (71-36-3) + sodium → 1,10-Decanediol (112-47-0)

dibutyl sebacate (109-43-3) + fumaroyl azide → trans-ethenediyl diisocyanate (1441-73-2)

tetrachloromethane (56-23-5) + dibutyl sebacate (109-43-3) + sodium → 2-hydroxy-cyclodecanone-(1)

Conditions	Yield
at 125 - 140℃;

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Recommend Products

• 22288-36-4  decanedioic acid benzyl ester-butyl ester 
• 100-51-6  benzyl alcohol 
• 1002-33-1  octa-1,3-diene 
• 201230-82-2  carbon monoxide 
• 71-36-3  butan-1-ol 
• 129-00-0  pyrene 
• 92-06-8  1,3-diphenylbenzene 
• 613-59-2  2-benzylnaphthalene 
• 5278-98-8  Decanedioic acid monobutyl ester 
• 111-20-6  1,10-decanedioic acid 
• 592-84-7  n-butyl formate 
• 111-19-3  sebacoyl chloride 
• 4128-90-9  1,8-Bis<4,6-diamino(1,3,5)triazin-2-yl>octan 
• 56-03-1  BIGUANIDE