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109-43-3

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109-43-3 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.

Check Digit Verification of cas no

The CAS Registry Mumber 109-43-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 9 respectively; the second part has 2 digits, 4 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 109-43:
(5*1)+(4*0)+(3*9)+(2*4)+(1*3)=43
43 % 10 = 3
So 109-43-3 is a valid CAS Registry Number.

109-43-3 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (A18231)  Di-n-butyl sebacate, 90+%   

  • 109-43-3

  • 100g

  • 296.0CNY

  • Detail
  • Alfa Aesar

  • (A18231)  Di-n-butyl sebacate, 90+%   

  • 109-43-3

  • 500g

  • 1019.0CNY

  • Detail
  • Sigma-Aldrich

  • (PHR1216)  Dibutylsebacate  pharmaceutical secondary standard; traceable to USP

  • 109-43-3

  • PHR1216-3X1.2ML

  • 732.19CNY

  • Detail
  • USP

  • (1187091)  Dibutylsebacate  United States Pharmacopeia (USP) Reference Standard

  • 109-43-3

  • 1187091-1ML

  • 4,326.66CNY

  • Detail
  • Sigma-Aldrich

  • (80865)  Dibutylsebacate  analytical standard

  • 109-43-3

  • 80865-1ML

  • 458.64CNY

  • Detail
  • Aldrich

  • (84840)  Dibutylsebacate  ≥97.0% (GC)

  • 109-43-3

  • 84840-250ML

  • 431.73CNY

  • Detail
  • Aldrich

  • (84840)  Dibutylsebacate  ≥97.0% (GC)

  • 109-43-3

  • 84840-1L

  • 967.59CNY

  • Detail
  • Sigma-Aldrich

  • (84838)  Dibutylsebacate  Selectophore, ≥97.0%

  • 109-43-3

  • 84838-5ML

  • 1,297.53CNY

  • Detail
  • Sigma-Aldrich

  • (84838)  Dibutylsebacate  Selectophore, ≥97.0%

  • 109-43-3

  • 84838-25ML

  • 5,374.98CNY

  • Detail
  • Aldrich

  • (D49504)  Dibutylsebacate  technical grade

  • 109-43-3

  • D49504-250ML

  • 583.83CNY

  • Detail
  • Aldrich

  • (D49504)  Dibutylsebacate  technical grade

  • 109-43-3

  • D49504-1L

  • 1,325.61CNY

  • Detail

109-43-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name Dibutyl sebacate

1.2 Other means of identification

Product number -
Other names Dibutyl Decanedioate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Emollients;Skin Conditioning Agents;Solvents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:109-43-3 SDS

109-43-3Synthetic route

1,10-decanedioic acid
111-20-6

1,10-decanedioic acid

butan-1-ol
71-36-3

butan-1-ol

dibutyl sebacate
109-43-3

dibutyl sebacate

Conditions
ConditionsYield
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

1,10-decanedioic acid

n-butyl formate
592-84-7

n-butyl formate

A

Decanedioic acid monobutyl ester
5278-98-8

Decanedioic acid monobutyl ester

B

dibutyl sebacate
109-43-3

dibutyl sebacate

Conditions
ConditionsYield
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

sebacoyl chloride

butan-1-ol
71-36-3

butan-1-ol

dibutyl sebacate
109-43-3

dibutyl sebacate

1-bromo-butane
109-65-9

1-bromo-butane

1,10-decanedioic acid
111-20-6

1,10-decanedioic acid

A

Decanedioic acid monobutyl ester
5278-98-8

Decanedioic acid monobutyl ester

B

dibutyl sebacate
109-43-3

dibutyl sebacate

Conditions
ConditionsYield
With sodium hydroxide; Aliquat 336 In toluene for 24h; Heating;
scrap tire

scrap tire

A

pyrene
129-00-0

pyrene

B

dibutyl sebacate
109-43-3

dibutyl sebacate

C

1,3-diphenylbenzene
92-06-8

1,3-diphenylbenzene

D

2-benzylnaphthalene
613-59-2

2-benzylnaphthalene

Conditions
ConditionsYield
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

octa-1,3-diene

carbon monoxide
201230-82-2

carbon monoxide

butan-1-ol
71-36-3

butan-1-ol

dibutyl sebacate
109-43-3

dibutyl sebacate

Conditions
ConditionsYield
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

dibutyl sebacate

A

1,10-decanedioic acid
111-20-6

1,10-decanedioic acid

B

Decanedioic acid monobutyl ester
5278-98-8

Decanedioic acid monobutyl ester

Conditions
ConditionsYield
With diethyl ether; water; sodium butanolate
dibutyl sebacate
109-43-3

dibutyl sebacate

hexachloroethane
67-72-1

hexachloroethane

Conditions
ConditionsYield
bei der Chlorierung im Sonnenlicht;
dibutyl sebacate
109-43-3

dibutyl sebacate

BIGUANIDE
56-03-1

BIGUANIDE

6,6'-octane-1,8-diyl-bis-[1,3,5]triazine-2,4-diamine
4128-90-9

6,6'-octane-1,8-diyl-bis-[1,3,5]triazine-2,4-diamine

dibutyl sebacate
109-43-3

dibutyl sebacate

benzyl alcohol
100-51-6

benzyl alcohol

decanedioic acid benzyl ester-butyl ester
22288-36-4

decanedioic acid benzyl ester-butyl ester

Conditions
ConditionsYield
With sodium methylate
dibutyl sebacate
109-43-3

dibutyl sebacate

toluene
108-88-3

toluene

butan-1-ol
71-36-3

butan-1-ol

sodium

sodium

1,10-Decanediol
112-47-0

1,10-Decanediol

dibutyl sebacate
109-43-3

dibutyl sebacate

fumaroyl azide

fumaroyl azide

trans-ethenediyl diisocyanate
1441-73-2

trans-ethenediyl diisocyanate

tetrachloromethane
56-23-5

tetrachloromethane

dibutyl sebacate
109-43-3

dibutyl sebacate

sodium

sodium

2-hydroxy-cyclodecanone-(1)

2-hydroxy-cyclodecanone-(1)

Conditions
ConditionsYield
at 125 - 140℃;

109-43-3Relevant articles and documents

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

Chen, Zhe,Han, Sheng,Lu, Deli,Xu, Yumeng

, (2021/08/23)

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.

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

Szelwicka, Anna,Boncel, S?awomir,Jurczyk, Sebastian,Chrobok, Anna

, p. 41 - 47 (2019/02/07)

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.

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

Britton, Joshua,Dalziel, Stuart B.,Raston, Colin L.

, p. 2193 - 2200 (2016/04/19)

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.

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