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Ethyl cellulose structure
Ethyl cellulose structure

Ethyl cellulose

Iupac Name:2-[N-butyl-4-[(2,6-dicyano-4-nitrophenyl)diazenyl]-3-methylanilino]ethyl acetate
CAS No.: 9004-57-3
Molecular Weight:448.47400
Modify Date.: 2022-04-18 21:43
Introduction: ethyl cellulose is a binder, film former, and thickener. It is used in suntan gels, creams, and lotions. This is the ethyl ether of cellulose. View more+
1. Names and Identifiers
1.1 Name
Ethyl cellulose
1.2 Synonyms

1,3-Benzenedicarbonitrile, 2-((4-((2-(acetyloxy)ethyl)butylamino)-2-methylphenyl)azo)-5-nitro- 1,3-Benzenedicarbonitrile, 2-[(E)-2-[4-[[2-(acetyloxy)ethyl]butylamino]-2-methylphenyl]diazenyl]-5-nitro- 2-(Butyl{4-[(E)-(2,6-dicyano-4-nitrophenyl)diazenyl]-3-methylphen yl}amino)ethyl acetate 2-(Butyl{4-[(E)-(2,6-dicyano-4-nitrophenyl)diazenyl]-3-methylphenyl}amino)ethyl acetate ampacete/c aquacoat aquacoatecd30 aquacoatecd30fmc cellulose,triethylether celluloseethyl EINECS 232-674-9 MFCD00131037 n-butyl-n-(2-acetoxyethyl)-4-((4-nitro-2,6-dicyanophenyl)azo)-3-methylbenzeneamine nixone/c spt50cps

1.3 CAS No.
9004-57-3
1.4 CID
24832091
1.5 EINECS(EC#)
232-674-9
1.6 Molecular Formula
C20H38O11 (isomer)
1.7 Inchi
InChI=1S/C20H38O11/c1-6-26-10-12-16(17(27-7-2)18(28-8-3)20(25-5)30-12)31-19-14(23)13(22)15(24-4)11(9-21)29-19/h11-23H,6-10H2,1-5H3
1.8 InChkey
ZZSNKZQZMQGXPY-UHFFFAOYSA-N
1.9 Canonical Smiles
CCOCC1C(C(C(C(O1)OC)OCC)OCC)OC2C(C(C(C(O2)CO)OC)O)O
1.10 Isomers Smiles
CCOCC1C(C(C(C(O1)OC)OCC)OCC)OC2C(C(C(C(O2)CO)OC)O)O
2. Properties
3.1 Density
1.45
3.1 Melting point
240-255ºC
3.1 Boiling point
657.6°C at 760 mmHg
3.1 Refractive index
1.14
3.1 Flash Point
351.5°C
3.1 Precise Quality
448.18600
3.1 PSA
147.66000
3.1 logP
5.75476
3.1 Solubility
esters, aromatic hydrocarbons, alcohols and ketones: soluble
3.2 Appearance
white to liqht tan
3.3 Storage
Ambient temperatures.
3.4 Chemical Properties
white to slightly yellowish powder
3.5 Color/Form
WHITE NEEDLES FROM BENZENE
FREE-FLOWING, WHITE TO LIGHT TAN POWDER
AVAILABLE COMMERCIALLY AS CLEAR FILM OR SHEET
White, granular, thermoplastic solid
3.6 PH
AQ SUSPENSIONS ARE NEUTRAL TO LITMUS
3.7 Water Solubility
insoluble
3.8 Spectral Properties
Index of refraction: 1.47
SPECIFIC OPTICAL ROTATION: +26.1 DEG @ 20 DEG C/D (IN BENZENE)
FORMS FILMS THAT HAVE REFRACTIVE INDEX OF ABOUT 1.47
3.9 Stability
Stable under normal temperatures and pressures.
3.10 StorageTemp
2-8°C
3. Use and Manufacturing
4.1 Usage
ethyl cellulose is a binder, film former, and thickener. It is used in suntan gels, creams, and lotions. This is the ethyl ether of cellulose.
4. Safety and Handling
5.1 Hazard Codes
Xi
5.1 Risk Statements
R36/37/38
5.1 Safety Statements
S26-S36
5.1 Exposure Standards and Regulations
Substances migrating to food from paper and paperboard products used in food packaging that are generally recognized as safe for their intended use, within section 409 of the Act. Ethyl cellulose is included on this list.
Ethyl cellulose is a food additive permitted for direct addition to food for human consumption, as long as 1) the quantity of the substance added to food does not exceed the amount reasonably required to accomplish its intended physical, nutritive, or other technical effect in food, and 2) any substance intended for use in or on food is of appropriate food grade and is prepared and handled as a food ingredient.
Ethyl cellulose is a food additive permitted in feed and drinking water of animals.
Certification of this color additive when used as a diluent in color additive mixtures for marking food is not necessary for the protection of the public health, and therefore batches thereof are exempt from the certification pursuant to section 721(c) of the act.
5.2 DisposalMethods
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.
5.3 RIDADR
NONH for all modes of transport
5.3 FirePotential
FIRE HAZARD: MODERATE, WHEN EXPOSED TO HEAT OR FLAME OR BY CHEMICAL REACTION WITH OXIDIZING AGENTS. FLAMMABILITY VARIES WITH DEGREE OF REPLACEMENT OF OH- RADICAL OF CELLULOSE BY ETHYL RADICALS.
PRECAUTIONS FOR MODERATE FIRE HAZARD SHOULD BE ADOPTED FOR SOLID MATERIAL. IT IS FREQUENTLY HANDLED AS PASTE OR A SOLN IN FLAMMABLE SOLVENT, WHEN PRECAUTIONS FOR FLAMMABLE LIQUIDS & VAPORS MAY HAVE TO BE OBSERVED.
5.4 Safety Profile
Low toxicity by ingestion and skin contact. A skin irritant. When heated to decomposition it emits acrid smoke and irritating fumes
5.5 Formulations/Preparations
To avoid brittleness, ethyl cellulose formulations usually include an antioxidant such as hydroquinone monobenzyl ether, 4-hexylpyrocatechol, or diphenylamine.
Grades: Technical; NF; FCC
Commercial product has ethoxy content of 43-50%
Most frequently used in solvent mixtures containing 60 to 80 percent aromatic hydrocarbon and 20 to 40 percent alcohol; this percentage of alcohol results in minimum viscosity. /Ethyl cellulose resins/
5.6 Incompatibilities
Incompatible with paraffin wax and microcrystalline wax.
5.7 WGK Germany
1
5.7 RTECS
FJ5950500
5.7 Report

Reported in EPA TSCA Inventory.

5.8 Safety

Low toxicity by ingestion and skin contact. A skin irritant. When heated to decomposition it emits acrid smoke and irritating fumes.
Hazard Codes?Ethyl cellulose (CAS NO.9004-57-3):?IrritantXi
Risk Statements: 36/37/38?
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36: Wear suitable protective clothing.
WGK Germany: 1

5.9 Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rabbit LD50 skin > 5gm/kg (5000mg/kg) ? Food and Cosmetics Toxicology. Vol. 19, Pg. 113, 1981.
rat LD50 oral > 5gm/kg (5000mg/kg) ? Food and Cosmetics Toxicology. Vol. 19, Pg. 113, 1981.

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s) No symbol.
Signal word

No signal word.

Hazard statement(s)

none

Precautionary statement(s)
Prevention

none

Response

none

Storage

none

Disposal

none

2.3 Other hazards which do not result in classification

none

7. Other Information
7.0 Merck
14,3781
7.1 Chemical Properties
white to slightly yellowish powder
7.2 Chemical Properties
Ethylcellulose is a tasteless, free-flowing, white to light tan-colored powder.
7.3 Uses
ethyl cellulose is a binder, film former, and thickener. It is used in suntan gels, creams, and lotions. This is the ethyl ether of cellulose.
7.4 Uses
Film-former in coatings, hot-melt adhesives and transfer inks and as a plastic coating for a variety of substrates.
7.5 Uses
In the manufacture of plastics and lacquers. Pharmaceutic aid (tablet binder).
7.6 Uses
Used as a binder and filler in dry vitamin preparations, as a component of protective coatings for vitamin and mineral tablets, and as a fixative in flavoring compounds. It is a cellulose ether containing ethyoxy groups attached by an ether linkage and containing an anhydrous basis of not more than 2.6 ethoxy groups per anhydroglucose unit.
7.7 Production Methods
Ethylcellulose is prepared by treating purified cellulose (sourced from chemical-grade cotton linters and wood pulp) with an alkaline solution, followed by ethylation of the alkali cellulose with chloroethane as shown below, where R represents the cellulose radical:
RONa + C2H5Cl→ROC2H5+NaCl
The manner in which the ethyl group is added to cellulose can be described by the degree of substitution (DS). The DS designates the average number of hydroxyl positions on the anhydroglucose unit that have been reacted with ethyl chloride. Since each anhydroglucose unit of the cellulose molecule has three hydroxyl groups, the maximum value for DS is three.
7.8 Preparation
Ethyl cellulose is prepared by reacting cellulose with caustic to form caustic cellulose, which is then reacted with chloroethane to form ethyl cellulose. Plasticgrade material contains 44-48% ethoxyl.
Although not as resistant as cellulose esters to acids, it is much more resistant to bases. An outstanding feature is its toughness at low temperatures.
7.9 Brand name
Aquacoat ECD (FMC);Ethocel (Dow Chemical).
7.10 Pharmaceutical Applications
Ethylcellulose is widely used in oral and topical pharmaceutical formulations.
The main use of ethylcellulose in oral formulations is as a hydrophobic coating agent for tablets and granules.Ethylcellulose coatings are used to modify the release of a drug, to mask an unpleasant taste, or to improve the stability of a formulation; for example, where granules are coated with ethylcellulose to inhibit oxidation. Modified-release tablet formulations may also be produced using ethylcellulose as a matrix former.
Ethylcellulose, dissolved in an organic solvent or solvent mixture, can be used on its own to produce water-insoluble films. Higher-viscosity ethylcellulose grades tend to produce stronger and more durable films. Ethylcellulose films may be modified to alter their solubility, by the addition of hypromellose or a plasticizer. An aqueous polymer dispersion (or latex) of ethylcellulose such as Aquacoat ECD (FMC Biopolymer) or Surelease (Colorcon) may also be used to produce ethylcellulose films without the need for organic solvents. Drug release through ethylcellulose-coated dosage forms can be controlled by diffusion through the film coating. This can be a slow process unless a large surface area (e.g. pellets or granules compared with tablets) is utilized. In those instances, aqueous ethylcellulose dispersions are generally used to coat granules or pellets. Ethylcellulose-coated beads and granules have also demonstrated the ability to absorb pressure and hence protect the coating from fracture during compression.
High-viscosity grades of ethylcellulose are used in drug microencapsulation.
Release of a drug from an ethylcellulose microcapsule is a function of the microcapsule wall thickness and surface area.
In tablet formulations, ethylcellulose may additionally be employed as a binder, the ethylcellulose being blended dry or wetgranulated with a solvent such as ethanol (95%). Ethylcellulose produces hard tablets with low friability, although they may demonstrate poor dissolution.
Ethylcellulose has also been used as an agent for delivering therapeutic agents from oral (e.g. dental) appliances.
In topical formulations, ethylcellulose is used as a thickening agent in creams, lotions, or gels, provided an appropriate solvent is used. Ethylcellulose has been studied as a stabilizer for emulsions.
Ethylcellulose is additionally used in cosmetics and food products.
7.11 Safety Profile
Low toxicity by ingestion and skin contact. A skin irritant. When heated to decomposition it emits acrid smoke and irritating fumes
7.12 Safety
Ethylcellulose is widely used in oral and topical pharmaceutical formulations. It is also used in food products. Ethylcellulose is not metabolized following oral consumption and is therefore a noncalorific substance. Because ethylcellulose is not metabolized it is not recommended for parenteral products; parenteral use may be harmful to the kidneys.
Ethylcellulose is generally regarded as a nontoxic, nonallergenic, and nonirritating material.
As ethylcellulose is not considered to be a health hazard, the WHO has not specified an acceptable daily intake. The highest reported level used in an oral product is 308.8 mg in an oral sustained release tablet.
LD50 (rabbit, skin): >5 g/kg
LD50 (rat, oral): >5 g/kg
7.13 storage
Ethylcellulose is a stable, slightly hygroscopic material. It is chemically resistant to alkalis, both dilute and concentrated, and to salt solutions, although it is more sensitive to acidic materials than are cellulose esters.
Ethylcellulose is subject to oxidative degradation in the presence of sunlight or UV light at elevated temperatures. This may be prevented by the use of antioxidant and chemical additives that absorb light in the 230–340nm range.
Ethylcellulose should be stored at a temperature not exceeding 32°C (90°F) in a dry area away from all sources of heat. It should not be stored next to peroxides or other oxidizing agents.
7.14 Incompatibilities
Incompatible with paraffin wax and microcrystalline wax.
7.15 Regulatory Status
GRAS listed. Accepted for use as a food additive in Europe. Included in the FDA Inactive Ingredients Database (oral capsules, suspensions and tablets; topical emulsions and vaginal preparations). Included in nonparenteral medicines licensed in Europe. Included in the Canadian List of Acceptable Non-medicinal Ingredients.
7.16 Usage
Ethyl cellulose is used as a food additive and as an emulsifier. It is also used as a film-former in coatings, hot-melt adhesives and transfer inks. Further, it is employed as a binder, filler, plastic coating and diluents of color. In addition to this, it is used in lacquers and plastic toughing.
8. Computational chemical data
  • Molecular Weight: 448.47400g/mol
  • Molecular Formula: C20H38O11
  • Compound Is Canonicalized: True
  • XLogP3-AA: -1.5
  • Exact Mass: 454.24141202
  • Monoisotopic Mass: 454.24141202
  • Complexity: 496
  • Rotatable Bond Count: 12
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 11
  • Topological Polar Surface Area: 135
  • Heavy Atom Count: 31
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count: 10
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
  • CACTVS Substructure Key Fingerprint: AAADcfB4PAAAAAAAAAAAAAAAAAAAAAAAAAAkSAAAAAAAAAAAAAAAGgAACAAACBSwgAMCCAAABgAAAAAAAAAAAAAAAAAAAAAAAAAREAIAAAAiQAAFAAAHAAHAYAwAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
10. Realated Product Infomation