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

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

Different sources of media describe the Chemical Properties of 109-43-3 differently. You can refer to the following data:
1. clear liquid
2. Dibutyl sebacate is a clear, colorless, oily liquid with a bland to slight butyl odor.

Uses

Different sources of media describe the Uses of 109-43-3 differently. You can refer to the following data:
1. 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.
2. 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℃;

Upstream product

• 111-20-6 1,10-decanedioic acid 
• 71-36-3 butan-1-ol 
• 111-19-3 sebacoyl chloride 
• 109-65-9 1-bromo-butane 
• 592-84-7 n-butyl formate 
• 1002-33-1 octa-1,3-diene 
• 201230-82-2 carbon monoxide 

Downstream Products

• 111-20-6 1,10-decanedioic acid 
• 5278-98-8 Decanedioic acid monobutyl ester 
• 4128-90-9 1,8-Bis<4,6-diamino(1,3,5)triazin-2-yl>octan 
• 112-47-0 1,10-Decanediol 
• 22288-36-4 decanedioic acid benzyl ester-butyl ester 

Relevant articles and documents

Biomass-derived dibasic acids to diesters with inorganic ligand-supported catalyst: synthesis, optimization, characterization

Several attempts have been made to obtain aliphatic dicarboxylic diesters from esterification reaction to develop the biomass-derived platform molecules and green manufacturing processes. In this paper, Na3(H2O)6[AlMo6O18(OH)6], an Anderson-type polyoxometalate, firstly, was reported as a catalyst for diester synthesis from dicarboxylic acid to diester which showed an well productivity and selectivity characterized by 1H and 13C. Response surface methodology (RSM) integrated with the desirability function approach was used to determine the best operative conditions, and the optimal reaction parameters for maximum dipropyl succinate yield (77 ± 2.5%) were identified as 1.19?mol.% catalyst loading, 4.9:1 propanol/succinic acid ratio, 113?°C, and 9.6?h. Three batches of tests were carried for catalyst recycling with 78–75% yield even after 6 cycles of esterification. In addition, the substrate carbon chain was increased for investigation of substrate scope achieving satisfactory results and all products were characterized by 1H and 13C nuclear magnetic resonance spectroscopy.

Direct synthesis of adipic acid esters via palladium-catalyzed carbonylation of 1,3-dienes

The direct carbonylation of 1,3-butadiene offers the potential for a more cost-efficient and environmentally benign route to industrially important adipic acid derivatives. However, owing to the complex reaction network of regioisomeric carbonylation and isomerization pathways, a selective practical catalyst for this process has thus far proven elusive. Here, we report the design of a pyridyl-substituted bidentate phosphine ligand (HeMaRaphos) that, upon coordination to palladium, catalyzes adipate diester formation from 1,3-butadiene, carbon monoxide, and butanol with 97% selectivity and 100% atom-economy under industrially viable and scalable conditions (turnover number > 60,000). This catalyst system also affords access to a variety of other di- and triesters from 1,2- and 1,3-dienes.

Exceptionally active and reusable nanobiocatalyst comprising lipase non-covalently immobilized on multi-wall carbon nanotubes for the synthesis of diester plasticizers

A new method for the synthesis of dicarboxylic acid esters in the presence of a new heterogeneous nanobiocatalyst consisting of Candida antarctica lipase B immobilized on multi-walled carbon nanotubes (MWCNTs) has been developed. Selection and characterization of the support for Candida antarctica lipase B (CALB) was initially performed. Pristine and modified MWCNTs of different geometries, morphologies and surface/core modifications were tested as a lipase carrier and determining that the CheapTubes MWCNTs nanobiocatalyst with a 15.7 wt.% CALB loading was the most active nanobiocatalyst. The model reaction of succinic acid with n-butanol was carried out with a 4-molar excess of alcohol and 150 mg of nanobiocatalyst per 1 mmol of succinic acid at 45 °C in cyclohexane. The di-n-butyl succinate was obtained with 95% yield after 3 h. The activities of the new nanobiocatalysts were compared with the benchmark Novozyme-435 and other acidic catalysts. Recycling studies demonstrated the possibility of utilizing the most active MWCNTs-lipase biocatalyst six times without any significant loss of activity. The main advantage of this study is the superior activity of the new nanobiocatalyst, which resulted in a significant reduction of reaction times as compared to those reported in the literature.

Micro-flow nanocatalysis: synergic effect of TfOH@SPIONs and micro-flow technology as an efficient and robust catalytic system for the synthesis of plasticizers

The combination of continuous flow technology with immobilizing of only 0.13?mol% of triflic acid (TfOH) on silica-encapsulated superparamagnetic iron oxide nanoparticles (SPIONs) under solvent-free conditions successfully provided a powerful, efficient, and eco-friendly route for the synthesis of plasticizers. The turnover frequency value in micro-flow conditions varied in the range of 948.7 to 7384.6 h?1 compared to 403.8 to 3099 h?1 for in-flask. This technique works efficiently, encouraging future applications of micro-flow nano-catalysis in green chemistry.

The synthesis of di-carboxylate esters using continuous flow vortex fluidics

A vortex fluidic device (VFD) is effective in mediating the synthesis of di-esters at room temperature. Processing under ambient conditions allows for a simple and efficient synthesis, whilst operating under continuous flow addresses scalability. The rotational speed of the sample tube and the flow rate were critical variables during reaction optimization, and this relates to the behaviour of the fluid flow at a molecular level. Whilst at specific rotational speeds the tube imparts a vibrational response into the fluid flow, the flow rate dictates residence time and the ability to maintain high levels of shear stress. The combination of mechanically induced vibrations, rapid micromixing, high levels of shear stress and water evaporation results in yields up to 90% for 3.25 minutes or less residence time. These results are key for devising greener and more efficient processes both mediated by the VFD and other continuous flow platforms.

Synthesis of carboxylic acid esters in the presence of micro- and mesoporous aluminosilicates

The catalytic properties of zeolites HY, HBeta, and HZSM-12 and of mesoporous amorphous aluminosilicate in liquid-phase esterification of aliphatic (monobasic C1-C18, dibasic C6, C10) and aromatic (benzoic, trimellitic, phthalic) carboxylic acids with butanol were studied. Zeolite HBeta appeared to be the most active catalyst. Procedures were developed for preparing esters in the presence of zeolitic catalyst HBeta, ensuring 100% selectivity of ester formation at 90-98% conversion of the acid.

NOVEL FORMULATION OF DEHYDRATED LIPID VESICLES FOR CONTROLLED RELEASE OF ACTIVE PHARMACEUTICAL INGREDIENT VIA INHALATION

A new formulation of dehydrated lipid vesicles employs a vesicle preserver and permits the control of release and delivery of active pharmaceutical ingredients into the respiratory system for treatment in particular of asthma. The typical formulation provides controlled release of the active pharmaceutical ingredient from 0% to 100% from 0 to 72 hours after inhalation, changes the systemic administration to topical administration, allows prolonged therapeutic period for one administration, increased stability, with reduced dose, reduced systemic side effects, reduced toxicity.

Polyaldimines

Two component PUR composition can be obtained when a first component (A) is prepared having a PUR prepolymer with isocyanate groups and an aromatic polyisocyanate, a polyol, and a polyaldimine, obtainable from a polyamine with primary aliphatic amino groups and an aldehyde, and a second component (B). Two component PUR composition having high early strength can be obtained when a first component (A) is prepared having a PUR prepolymer with isocyanate groups and an aromatic polyisocyanate, a polyol, and a polyaldimine, obtainable from a polyamine with primary aliphatic amino groups and an aldehyde, which has no C-H groups in the alpha-position to the carbonyl group, and a second component (B) containing water bonded to a carrier material. Independent claims are included for: (1) a process for preparation of a two-component PUR composition involving a step for preparation of a polyaldimine from an aldehyde and a polyamine; (2) a process for mixing a two-component PUR composition where the mixing ratio of the first component A to the second component B is selected so that the ratio of equivalent water (sic) to equivalent aldimine groups is 0.5-10.0, especially 1.0-5.0; and (3) a process for application of a two-component PUR composition involving the steps: mixing of A and B, contacting solid body surface (sic) with the mixed PUR composition, and curing of the mixed PUR composition.

Evolution of products in the combustion of scrap tires in a horizontal, laboratory scale reactor

A horizontal laboratory reactor was used to study the evolution of byproducts from the combustion of scrap tires at five nominal temperatures (ranging from 650 to 1050 °C) and different oxygen:sample ratios A model was used to calculate the bulk air ratio (λ), and the oxygen consumption was discussed considering this ratio λ. More than 100 volatile and semivolatile compounds were identified and quantified by gas chromatography mass spectrometry, plotting their yields vs the bulk air ratio and temperature. Five different behaviors considering the bulk air ratio and the temperature were identified.

Selective monoesterification of dicarboxylic acids catalysed by ion-exchange resins

Symmetrical dicarboxylic acids with 4-14 carbon atoms gave selectively the corresponding monoesters in high yields in the transesterification catalysed by strongly acidic ion-exchange resins in ester-hydrocarbon mixtures. It was found that the rate of the esterification of the dicarboxylic acids is much higher than that of the monocarboxylic acids formed. This result can explain the high selectivity for the monoester formation and can also be explained by the existence of an aqueous layer on the surface of the resins. This method of selective esterification is quite simple and practical. The Royal Society of Chemistry 1999.