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77-94-1

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77-94-1 Usage

Outline

Tributyl citrate (TBC) is a good environmental plasticizers, lubricants. At room temperature, it is non-toxic, it has fruit flavor, it is colorless oily liquid. Boiling point is 170℃ (133.3Pa), flash point (open cup) is 185℃. It is soluble in most organic solvents. Volatile is small, it has good compatibility with the resin, it has high efficiency in plastification, in Europe and other countries it is allowed for food packaging and medical products, as well as children's soft toys, pharmaceuticals, medical products, flavors and fragrances, cosmetics manufacturing and other industries.Products can be given a good cold resistance, water resistance and mildew resistance. The product which is resin plasticized can exhibit good transparency and low temperature flexural properties, and has low volatility and low extraction resistance in different media, thermal stability, it does not change color when be heat. The product which prepared by lubricating oil can have good lubricating properties.

New non-toxic plasticizer

The most commonly used plasticizer is phthalate esters industrially, because it can induce cancer, the use in foreign countries has been controlled strictly , China has also formulated relevant laws and regulations, and will phase out its use in food packaging materials, medical appliances toys . Tributyl citrate (TBC) is a new non-toxic plasticizer, because it has good compatibility, high plasticizing efficiency, non-toxic and less volatile, weather resistance and other characteristics of broad interest, it is used as the preferred alternative green products in place of phthalic dimethyl esters. With the growing awareness of environmental protection and improvement of environmental regulations, the development and production of tributyl citrate has excellent prospects. Tributyl citrate is usually caused with citric acid and n-butanol in the presence of catalyst by esterifying, the conventional catalyst is concentrated sulfuric acid, although its low price, high catalytic activity, it can cause serious corrosion for equipment, post-processing process is complex, the select of reaction is poor, environmental pollution is serious and other defects, and thus the work of seeking alternative catalysts in place of concentrated sulfuric acid is very active, some better catalytic effect of the catalyst has been found: [Sodium bisulfate catalytic synthesis of tributyl citrate] Monohydrate Sodium hydroxide is a strong ionic compounds, the study found that it is soluble in water, aqueous solution is strongly acidic but it is insoluble in organic acids and alcohols reaction system, it can be used as a catalyst for esterification, studies show that the catalyst has a high activity catalytic, good stability, high yield, easy separation, convenient synthesis method, no corrosion, no pollution and other advantages. [Synthesis of solid superacid catalyst] Superacid is an acid, which the strength is greater than 100% sulfuric acid. Studies have shown that using it as a catalyst for the esterification reaction has good selectivity, fast response, high yield, easy separation, ease of operation, and the catalyst is stable, reusable, non-corrosive, non-polluting, it is a kind of promising catalyst. [Synthesis of p-toluenesulfonic acid catalysis] Toluenesulfonic acid is a strong organic acid, it can be used to instead of concentrated sulfuric acid as the esterification catalyst, and the corrosion for equipment and waste pollution is much smaller than that of sulfuric acid, it is also high activity and selectivity, cheap, dosage less, good product color, it is fit catalyst for industrial production. [Miscellaneous catalytic synthesis of tributyl citrate] Heteropolyacid is a multi-proton acid, the stronger of acidity, the more conducive to the formation of salt, it provide more favorable conditions for other nucleophilic attack, thus it speeds up the rate of the esterification reaction. It is non-volatile, the thermal stability is well, it also cause less pollution and can reduce equipment corrosion, it is an ideal esterification catalyst. The above information is edited by the lookchem of Wang Xiaodong.

Chemical properties

It is colorless, oily liquid, slightly scented. It is insoluble in water, soluble in methanol, acetone, carbon tetrachloride, acetic acid, castor oil, mineral oil, organic solvents.

Uses

Different sources of media describe the Uses of 77-94-1 differently. You can refer to the following data:
1. This product is innocuous plasticizer, it can be used for granulation of non-toxic PVC, it can be used for packaging materials in food production, soft toys for children, medical products, the plasticizer for polyvinyl chloride, vinyl chloride copolymers, cellulose resin.
2. Plasticizer and solvent for nitrocellulose lacquers; in polishes, inks and similar Preparations; also as anti-foam agent.
3. Tributyl Citrate, is a non-phthalate plasticizer, that can be used for the preparation of resins. It can also used for the synthesis of Acetyl Tributyl Cirate, a valuable biodegradable plasticizer of low toxicity, found in nail polish and other cosmetics.
4. Tributyl citrate can be used:To incorporate in zein film to enhance its mechanical properties for industrial processing.As a plasticizer to improve the ductile properties of poly(lactide) polymers.

Chemical Properties

Different sources of media describe the Chemical Properties of 77-94-1 differently. You can refer to the following data:
1. Colorless or pale-yellow, stable, odorless, nonvolatile liquid. Practically insoluble in water. Combustible.
2. Tributyl citrate is a clear, odorless, practically colorless, oily liquid.

Production Methods

Tributyl citrate is prepared by the esterification of citric acid with butanol.

General Description

Tributyl citrate is an ester of citric acid. It is used to plasticize polymers for coating solid drug dosage forms, tablets and capsules.Certified pharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to pharmacopeia primary standards.

Pharmaceutical Applications

Tributyl citrate is used to plasticize polymers in formulated pharmaceutical coatings. The coating applications include capsules, tablets, beads, and granules for taste masking, immediate release, sustained-release, and enteric formulations.

Safety

Tributyl citrate is used in oral pharmaceutical formulations. It is generally regarded as an essentially nontoxic and nonirritating material. However, ingestion of large quantities may be harmful. LD50 (cat, oral): >50 mL/kg LD50 (mouse, IP): 2.9 g/kg LD50 (rat, oral): >30 mL/kg

storage

Tributyl citrate should be stored in well-closed containers in a cool, dry location at temperatures not exceeding 38℃. When stored in accordance with these conditions, tributyl citrate is a stable material.

Incompatibilities

Tributyl citrate is incompatible with strong alkalis and oxidizing materials.

Regulatory Status

Approved in the USA for indirect food contact in food films. Included in the Canadian List of Acceptable Non-medicinal Ingredients.

Check Digit Verification of cas no

The CAS Registry Mumber 77-94-1 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 7 respectively; the second part has 2 digits, 9 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 77-94:
(4*7)+(3*7)+(2*9)+(1*4)=71
71 % 10 = 1
So 77-94-1 is a valid CAS Registry Number.
InChI:InChI=1/C18H32O7/c1-4-7-10-23-15(19)13-18(22,17(21)25-12-9-6-3)14-16(20)24-11-8-5-2/h22H,4-14H2,1-3H3

77-94-1 Well-known Company Product Price

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

  • (A10266)  Tri-n-butyl citrate, 99%   

  • 77-94-1

  • 50g

  • 89.0CNY

  • Detail
  • Alfa Aesar

  • (A10266)  Tri-n-butyl citrate, 99%   

  • 77-94-1

  • 250g

  • 394.0CNY

  • Detail
  • Alfa Aesar

  • (A10266)  Tri-n-butyl citrate, 99%   

  • 77-94-1

  • 1000g

  • 874.0CNY

  • Detail
  • Sigma-Aldrich

  • (PHR1154)    pharmaceutical secondary standard; traceable to USP

  • 77-94-1

  • PHR1154-1G

  • 732.19CNY

  • Detail
  • USP

  • (1680608)  Tributylcitrate  United States Pharmacopeia (USP) Reference Standard

  • 77-94-1

  • 1680608-500MG

  • 4,662.45CNY

  • Detail

77-94-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Tributyl citrate

1.2 Other means of identification

Product number -
Other names 1,2,3-Propanetricarboxylic acid, 2-hydroxy-, tributyl ester

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
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:77-94-1 SDS

77-94-1Synthetic route

citric acid
77-92-9

citric acid

butan-1-ol
71-36-3

butan-1-ol

Citroflex-4
77-94-1

Citroflex-4

Conditions
ConditionsYield
With 1,3-propanesultone; sulfuric acid; manganese(II) acetate; Cycloheximide In water; toluene at 65 - 100℃; for 31h; Temperature; Ionic liquid;98.6%
With dimesitylammonium pentafluorobenzenesulfonate In n-heptane at 80℃; for 24h;97%
With 3H(1+)*O40SiW12(4-)*C21H22O3PS(1+) Concentration; Reflux; Dean-Stark;97.5%
sulfuric acid
7664-93-9

sulfuric acid

citric acid
77-92-9

citric acid

butan-1-ol
71-36-3

butan-1-ol

Citroflex-4
77-94-1

Citroflex-4

Conditions
ConditionsYield
at 150℃; sowie bei 175grad und 200grad;
citric acid
77-92-9

citric acid

butan-1-ol
71-36-3

butan-1-ol

A

monobutyl citrate
118068-28-3

monobutyl citrate

B

dibutyl ether
142-96-1

dibutyl ether

C

Citroflex-4
77-94-1

Citroflex-4

D

sym-di-n-butyl citrate
101996-65-0

sym-di-n-butyl citrate

Conditions
ConditionsYield
Amberlyst 15 at 25 - 120℃; for 16h;
Glyoxilic acid
298-12-4

Glyoxilic acid

butan-1-ol
71-36-3

butan-1-ol

A

Dibutyl maleate
105-76-0

Dibutyl maleate

B

di-n-butyl oxalate
2050-60-4

di-n-butyl oxalate

C

dibutyl succinate
141-03-7

dibutyl succinate

D

L-(-)-di-n butyl malate
1587-18-4

L-(-)-di-n butyl malate

E

dibutyl tartrate
344268-32-2

dibutyl tartrate

F

propane-1,2,3-tricarboxylic acid tributyl ester
38094-11-0

propane-1,2,3-tricarboxylic acid tributyl ester

G

Citroflex-4
77-94-1

Citroflex-4

H

dibutyl fumarate
105-75-9

dibutyl fumarate

I

C11H20O5
117538-83-7

C11H20O5

J

C12H22O4S3
94086-70-1

C12H22O4S3

Conditions
ConditionsYield
Stage #1: Glyoxilic acid With sodiumsulfide nonahydrate In water at 90℃; for 168h;
Stage #2: butan-1-ol With hydrogenchloride at 90℃; for 2h;
n-Butyl chloride
109-69-3

n-Butyl chloride

sodium citrate
68-04-2

sodium citrate

Citroflex-4
77-94-1

Citroflex-4

Conditions
ConditionsYield
Stage #1: n-Butyl chloride With potassium iodide In acetone for 2h; Inert atmosphere; Reflux;
Stage #2: sodium citrate In N,N-dimethyl-formamide at 60℃; for 3h; Temperature;
Citroflex-4
77-94-1

Citroflex-4

acetic anhydride
108-24-7

acetic anhydride

acetyltributyl citrate
77-90-7

acetyltributyl citrate

Conditions
ConditionsYield
dmap at 100℃; for 24h;93%
With 1-butyl-3-methylimidazolium 4-methylbenzenenesulfonate; 1-butyl-3-methylimidazolium Tetrafluoroborate at 50℃; for 8h;19%
at 70 - 80℃; Concentration;
vinyl acetate
108-05-4

vinyl acetate

Citroflex-4
77-94-1

Citroflex-4

acetyltributyl citrate
77-90-7

acetyltributyl citrate

Conditions
ConditionsYield
With potassium tert-butylate; 1-ethyl-3-methylimidazolium tetrafluoroborate In tetrahydrofuran at 70℃; for 12h; Reagent/catalyst; Solvent; Time; Temperature; Concentration; Inert atmosphere;81%
Citroflex-4
77-94-1

Citroflex-4

acetic acid
64-19-7

acetic acid

acetyltributyl citrate
77-90-7

acetyltributyl citrate

Conditions
ConditionsYield
[Mes2NH2](+)[O3SC6F5](-) In n-heptane at 115℃; for 48h;31%
Citroflex-4
77-94-1

Citroflex-4

1-propene-1,2,3-tricarboxylic acid tributyl ester
343599-72-4

1-propene-1,2,3-tricarboxylic acid tributyl ester

Conditions
ConditionsYield
With phosphoric acid; acetic anhydride at 155℃; durch Leiten des Reaktionsprodukts durch ein auf 425grad erhitztes Rohr;
With sulfuric acid; acetic anhydride at 155℃; durch Leiten des Reaktionsprodukts durch ein auf 425grad erhitztes Rohr;
Citroflex-4
77-94-1

Citroflex-4

hexan-1-ol
111-27-3

hexan-1-ol

tri-n-hexyl citrate
16544-70-0

tri-n-hexyl citrate

Conditions
ConditionsYield
aluminium(III) triflate at 150 - 195℃; under 37.5038 - 7500.75 Torr; Conversion of starting material;
Citroflex-4
77-94-1

Citroflex-4

C22H35ClO9

C22H35ClO9

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tetrachloromethane / 4 h / 70 °C / Inert atmosphere
2: phosphorus trichloride / 60 °C
View Scheme
succinic acid anhydride
108-30-5

succinic acid anhydride

Citroflex-4
77-94-1

Citroflex-4

C22H36O10

C22H36O10

Conditions
ConditionsYield
In tetrachloromethane at 70℃; for 4h; Inert atmosphere;

77-94-1Relevant articles and documents

Preparation supported heteropoly (acid)/polyaniline catalysts and catalytic synthesis of tributyl citrate

Wang, Limin,Ding, Bin,Zhang, Miao

, p. 33124 - 33129 (2019)

A series of polyaniline supported heteropoly acids were prepared through a simple method at room temperature. The obtained heterogeneous catalysts were comprehensively characterized by powder FTIR spectroscopy, UV-vis spectra, NH3 temperature programmed desorption (TPD) and scanning electron microscopy (SEM). The influence of various process parameters such as heteropoly loading (10 to 25 wt%), catalyst amount (3-5%), molar ratio of n-butanol to citric acid (3 to 5), and reaction time (3.5-12 h) have been investigated over heteropoly/polyaniline catalysts with the aim to maximize citric acid conversion and tributyl citrate selectivity. The different catalytic tests has shown that the catalyst exhibits high conversion and selectivity by using the as-prepared heteropoly/polyaniline catalysts for esterification under appropriate conditions. The present method of using 20% heteropoly/polyaniline catalyst for the synthesis of tributyl citrate would be environmentally benign in the reusability of catalyst.

PLASTICIZER COMPOSITION AND RESIN COMPOSITION INCLUDING THE SAME

-

Paragraph 0119-0120; 0122, (2021/07/31)

Provided is a plasticizer composition including: a cyclohexane-1,2-diester-based substance of the following Chemical Formula 1; and a citrate-based substance of the following Chemical Formula 2: wherein in Chemical Formula 1 and Chemical Formula 2: R1 and R2 each independently are a C8 to C10 alkyl group; and R3 to R5 each independently are a C5 to C10 alkyl group.

Citrate plasticizer

-

Paragraph 0027-0029, (2021/05/15)

The invention discloses a citrate plasticizer and a preparation method thereof, and the preparation method of citrate comprises the following steps: firstly, citric acid and alcohol react to prepare citric acid triester, and then dianhydride acylation is carried out to prepare carboxyl-containing citric acid triester. After chlorination, the carboxyl-containing citric acid triester and the tris(2-ethoxyl) isocyanurate are subjected to esterification reaction to prepare triester citrate containing the isocyanurate. According to the present invention, the preparation method has characteristics of simple operation, wide raw material source and mild reaction condition, and meets the industrial production, the prepared triester citrate containing isocyanurate has a good plasticizing effect and excellent thermal stability, low-temperature flexibility, solvent extraction resistance, migration resistance and flame retardance, and can be widely applied to plastic rubber plasticizers.

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