SULFATED CASTOR OIL

Sulfated Castor Oil 
CAS no.: 8002-33-3
EC / List no.: 232-306-7
FORMULA: C18H32Na2O6S
Castor oil is a vegetable oil pressed from castor beans. It is a colourless to very pale yellow liquid with a distinct taste and odor. Its boiling point is 313 °C (595 °F) and its density is 0.961 g/cm3. It includes a mixture of triglycerides in which about 90% of fatty acids are ricinoleates. Oleate and linoleates are the other significant components.
Castor oil and its derivatives are used in the manufacturing of soaps, lubricants, hydraulic and brake fluids, paints, dyes, coatings, inks, cold-resistant plastics, waxes and polishes, nylon, pharmaceuticals, and perfumes.
A sulfated castor oil substitute is prepared by sulfating a mixture of alcohol and unsaturated oils. This product is useful as a textile softener.

Synonym: Sulfated castor oil; Aquasol; Castor oil, sulfated; Turkey red oil; Turkey-red oil; Caswell No. 899; UNII-75T1HFY189; DTXSID00897290; 75T1HFY189; EINECS 232-306-7; EPA Pesticide Chemical Code 079014; Q2446707
Claims, No Drawings SULFATED CASTOR OIL SUBSTITUTE AND ITS USE IN TEXTILE TREATMENT BACKGROUND OF THE INVENTION 1. Field of the Invention This invention relates to sulfated mixtures of alcohols and unsaturated oils and use of these mixtures as sulfated castor oil substitutes in textile treatment.
SUMMARY OF THE INVENTION A substitute for sulfated castor oil is prepared by sulfating a mixture of a. from about 10% to about 70% by weight of at least one aliphatic alcohol having from about 4 to about 30 carbon atoms; and b. from about 90% to about 30% by weight of at least one unsaturated fat other than castor oil. The sulfated mixture is useful as a softener for textiles.
DESCRIPTION OF PREFERRED EMBODIMENTS The sulfated castor oil substitutes disclosed in this application can be obtained by sulfation of aliphatic alcohols having from about 4 to about 30 carbon atoms and unsaturated vegetable or animal oils. These castor oil substitutes can be prepared by sulfation of mixtures containing from about 10% to about 70% by weight of aliphatic alcohols and from about 90% to about 30% by weight of unsaturated fat; aliphatic alcohols and about 80% to about 40% by weight of unsaturated fat.
These mixtures include saturated or unsaturated, branched or linear, monohydric or divalent alcohols such as butyl, isobutyl, amyl, hexyl, heptyl, ethylhexyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, Mono and their major lagomers such as octadecyl, nonadecyl, eicosyl, heneicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl and triacontyl, corresponding secondary and tertiary alcohols, secondary amyl alcohol, polyunsaturated substances, mixtures thereof and the like . Useful alcohols include those produced by hydrogenation of fatty acids or glycerides derived from animal or vegetable oils and waxes, such as coconut oil, tallow, tallow or the like. Other alcohols can be produced by the 0x0 process. This process involves the catalytic reaction of alpha-olefins with carbon monoxide and hydrogen under pressure to obtain primary aliphatic alcohols with branched chains. Oxo alcohols include i-octyl, decyl, tridecyl, pentadecyl, mixtures thereof, and the like. Other primary aliphatic alcohols include those produced by the polymerization of ethylene with Ziegler-type catalysts followed by the reaction of the metal alkyls formed in this polymerization to yield mixtures of straight-chain primary alcohols. These alcohols may be used as mixtures or as specific primary alcohols such as hexyl, octyl and decyl and may be mixtures of individual primary alcohols or separate primary alcohols having chain lengths of from about eight to about twenty-eight carbon atoms. Other primary aliphatic alcohols include those produced by the polymerization of ethylene with Ziegler-type catalysts followed by the reaction of the metal alkyls formed in this polymerization to yield mixtures of straight-chain primary alcohols. These alcohols may be used as mixtures or as specific primary alcohols such as hexyl, octyl and decyl and may be mixtures of individual primary alcohols or separate primary alcohols having chain lengths of from about eight to about twenty-eight carbon atoms. Other primary aliphatic alcohols include those produced by the polymerization of ethylene with Ziegler-type catalysts followed by the reaction of the metal alkyls formed in this polymerization to yield mixtures of straight-chain primary alcohols. These alcohols may be used as mixtures or as specific primary alcohols such as hexyl, octyl and decyl and may be mixtures of individual primary alcohols or separate primary alcohols having chain lengths of from about eight to about twenty-eight carbon atoms.
Preferred alcohols have a backbone of 8 to 22 carbon atoms, are monohydric, primary, and may be unsaturated. Preferred alcohols include mixtures containing C Oxo treatment bases that are both branched and linear.
Useful unsaturated fats include those with an iodine value of over 60 and include, but are not limited to: acorn, almond, apricot kernel, beech nut, black mustard, brazil nut, wax, cashew nut shell, chaulmoogra, vegetable oils such as corn, cottonseed, croton, ergot, grape seed, hazelnut, hemp seed, jute seed, laurel, lemon, linseed, oat, olive, peach seed, peanut, pecan seed, perilla, pistachio, plum seed, poppy seed, pumpkin seed, rapeseed, rice bran, safflower, sesame, soybean, sunflower, tung, walnut, wheat and mustard seeds; animal fats such as lard and clean feet; and fish oils such as cod liver, shark, herring, menhaden, sardine and shark.
Preferred unsaturated fats include those with an iodine value above 90 such as cod liver, corn, cottonseed, croton, hemp seeds, herring, lemon, flaxseed, peanuts, walnuts, rapeseed, rice bran and teaseed. .
The compositions of the present invention can be substituted for sulfated castor oil in any formulation where this material is used as a fabric softener or can be used on its own as a fabric softener. When used in a mineral oil-containing formulation, the compositions may contain more than 60% mineral oil and up to the amount carried by sulfated natural castor oil. Thus, these compositions give the fibers more softness, more surface feel, more light fastness. Some of these compositions may contain up to four parts of mineral oil.
These sulfated compositions can be used in separate finishing processes as textile softeners to improve the handle and feel of finished textiles. It is desirable to use these compositions in the finishing of textiles. For example, in the processing of cotton textiles, vegetable waxes are removed during boiling, bleaching, dyeing, so a finishing agent such as these sulfated castor oil substitutes must be added as the final finish. goods to improve a little hard hand after wet processing. The sulfated compositions can be used on textile materials derived from natural, man-made and synthetic fibers such as cotton, wool, silk, jute, sisal, hemp, fur, linen, kapok, rayon, cellulose acetate, cellulose triacetate, polyamides such as nylon. polyesters such as polyethylene terephthalate (Dacron), acrylics such as polyacrylonitrile, vinyl resins such as copolymers of polyvinyl chloride and polyvinyl acetate. vinylidene chloride and vinyl chloride copolymers, acrylonitrile and vinyl chloride copolymers and the like, polystyrene. polyethylene. protein fibers such as polypropylene, polyurethanes, glass, vicara and peanut. mixtures of these fibers and the like.
For a better understanding of the nature and objects of the present invention, reference may be made to the following examples. These examples are provided solely to illustrate the invention and should not be construed in a limiting sense. All episodes. ratios and amounts are by weight unless otherwise stated. g, lC, F, hr terms. in is used to denote grams, liters, degrees Celsius, degrees Fahrenheit, hours, inches, respectively. in these examples.
Example IA The reactor was charged with 50 parts by weight of refined mustard seed oil and 50 parts by weight of C. The reaction mixture was reacted at this temperature for an additional hour and then dripped into 200 parts by weight of wash water containing 20 parts by weight. salt at 35C. The reaction mixture was immersed in brine wash water for approximately 45 minutes. After this time, wash water was withdrawn from the reaction product and the product was neutralized to an acid value of 4045. The product was then adjusted to an alkalinity of 0.25% as KOH with 50% sodium hydroxide solution and then allowed to stand overnight. If necessary, the product was allowed to stay longer until a moisture value of 25% or less was achieved. The reaction product was then bleached and stabilized.
The reaction product was a cloudy amber liquid at 25°C. It formed a 10% wt emulsion (as is) that was easily miscible (as is) in water in water at 25°C and was stable for more than two weeks at 25°C. These data are given in Table 1 below.
Alcohols (Oxo process substrates containing both branched and linear alcohols) at 25°C. A total of 30 parts by weight of 98% sulfuric acid was added to the reactor charge over 1 hour while maintaining the reaction temperature at about 10 to about C.
The reaction mixture was reacted for another hour at this temperature and then dripped into 200 parts by weight wash water containing 20 parts by weight salt at 35 °C and allowed to stand in the brine wash for about 45 minutes. After this time, wash water was withdrawn from the reaction product and the product was neutralized to a total acid value of 20-30, then adjusted to an alkalinity of 0.25% as KOH with 50% sodium hydroxide solution and allowed. to stand at night. If necessary, the product was allowed to remain longer until the moisture value or less was achieved. An additional 50% sodium hydroxide solution was then added to clarify the product. reaction product. bleached and stabilized, which is the desired sulfated castor oil substitute.
The reaction product was a clear amber liquid at 25°C. It is easily miscible at 10 wt% (as is) water in water at 25°C and forms a 10% wt emulsion (as is) that is stable for more than 2 weeks at 25°C. These data are shown in Table 1 below, along with comparable data for a commercial sulfated castor oil.
Example [I Reactor was charged with 70 parts by weight of crude peanut oil and parts by weight of C alcohols (Oxo process substrates containing both branched and linear alcohols). A total of 30 parts by weight of 98% sulfuric acid was added to the charge in the reactor while maintaining the reaction temperature at about 10 to about 20°C.

Preparation of Fabric Samples Example I was evaluated using the sulfated castor oil substitutes prepared in Example II and a commercial sulfated castor oil, cut 4 in X 12 on non-mercerized cotton, 50/50 polyester/cotton blend, and 100% unfinished fabric samples. nylon semi-dull taffeta. The fabric samples were weighed and then 3% by weight solids of the sulfated castor oil substitutes prepared in Examples 1 and 11, respectively, and commercial sulfated castor oil were applied to the individual fabric samples as finishes. Sulphated castor oil and commercial sulfated castor oil from Examples 1 and 11 were first mixed with 3% solids.
diluted with sufficient water to obtain final baths giving wet aggregation. Each of the fabric samples was dipped once in the finishing bath and then squeezed once between rollers to achieve the desired 3% solids wet uptake.
Roasting Test at 400F This test was performed using 100% cotton and 50/50 polyester/cotton blend fabric samples prepared above. These samples had 3% of the sulfated castor oil substitute in Examples 1 and 11 as finishes. The samples were placed between the heated (400F) plates of the AATCC roasting tester (Atlas Electric Industries, lnc., Chicago, Illinois). Reaction Product of the Product of Example I Example I Example II Blank I cotton light light light 50/50 Blend moderately light Polyester/cotton Hand Softness This test was conducted using 100% cotton fabric samples prepared above. These samples were treated with 3% of the sulfated castor oil substitute from Example 1. The sulfated castor oil substitute in Example [I and a commercial sulfated castor oil as polishes. A blank sample that was not treated with sulfated castor oil was also included in this test. Fabric samples were conditioned at 70°F and 50% RH for 16 hours. Samples were then compared with blank samples to obtain the results given in Table III below. These results show that the softness of fabric samples treated with the reaction products of Example 1 and [I is equal to the softness of a fabric sample treated with commercial sulfated castor oil. The samples were then compared with blank samples to obtain the results given in Table III below. These results show that the softness of fabric samples treated with the reaction products of Example 1 and [I is equal to the softness of a fabric sample treated with commercial sulfated castor oil. Samples were then compared with blank samples to obtain the results given in Table III below. These results show that the softness of fabric samples treated with the reaction products of Example 1 and [I is equal to the softness of a fabric sample treated with commercial sulfated castor oil.
Composition:
Castor oil is well known as a source of ricinoleic acid, a monounsaturated, 18-carbon fatty acid. Among fatty acids, ricinoleic acid is unusual in that it has a hydroxyl functional group on the 12th carbon. This functional group causes ricinoleic acid (and castor oil) to be more polar than most fats. The chemical reactivity of the alcohol group also allows chemical derivatization that is not possible with most other seed oils. Because of its ricinoleic acid content, castor oil is a valuable chemical in feedstocks, commanding a higher price than other seed oils.
Uses:
Annually, 270,000–360,000 tonnes (600–800 million pounds) of castor oil are produced for a variety of uses.
Sulphonated castor oil is used in several applications where it functions as wetting agent, dispersing agent, levelling agent and detergent.
Sulfated castor oil is a surfactant used as a cleansing agent.
Used in Textile industries, Sugar industry, as a defoaming agent, as an Emulsifier. In cosmetics it is used as humectants and as an Emulsifier for Oil Bath.
Sulfonated castor oil, also called Sulfonated (sulfated) castor oil, or Turkey Red Oil, is the only oil that completely disperses in water. 
Sulfonated castor oil is made by adding sulfuric acid to pure castor oil.
This allows easy use for making bath oil products.
Sulfonated castor oil was the first synthetic detergent after ordinary Soap.
Sulfonated castor oil is used in formulating lubricants, softeners, and dyeing assistants 
reaction temperature is controlled by regulating the flow of water to the cooling coils. This can be done manua.lly, or by automatic controls.
Modification of the Refined Castor Oil: Sulphation  20g of oil was warmed at 35°C.
15ml of concentrated sulphuric acid (98%) was then added and the reaction was allowed to completion with constant stirring.
After, the product was washed with hot distilled water and left to stand for 2 hrs, after which water was then removed.
And the sulphuric acid ester formed was finally neutralized with 10ml of 0.1m Sodium Hydroxide.
Characterization of TRO Specific gravity, pH, acid value, iodine value, saponification value, refractive index and viscosity of the oil were determined Determination of Specific Gravity Density bottle  was used  to determination  of density of  the oil. 
A clean and  dry bottle  of 25ml  capacity was weighed (W0) and then filled with the oil, stopper inserted and reweighed to give (W1).
The oil was substituted with water after washing and drying the bottle and weighed to give (W2).
The expression for specific gravity (Sp.gr) is: Sp.gr = (W1-W0)/(W2-W0) = Mass of the substance / Mass of an equal volume of water [7].
Determination of PH value  The pH value of oil was determined with the aid of a pH meter (Model Delta 320, Mettler Toledo, China).
Determination of Acid Value The method was specified by ISO 660 (2009). 25ml of diethyl ether and 25ml of ethanol was mixed in a 250 ml beaker.
The resulting mixture was added to 10g of  oil in a 250ml conical flask and few drops of phenolphthalein were added to the mixture.
The mixture was titrated with 0.1N KOH to the end point with consistent shaking for which a dark pink colour was observed and the volume of 0.1N KOH (V) was noted [7].
Acid value = (56.1*V*C)/M Where V is the volume in ml of standard volumetric KOH solution  used, C is the exact concentration in KOH solution used (0.1 N); m is the mass in grams of the test portion (1g). 56.1 is equivalent weight of KOH. Determination of Saponification Value Indicator method was use as specified by ISO 3657 (2002).
2g of the sample was weighed into a conical flask; 25ml of 0.1N ethanolic potassium hydroxide of was then added. The content which was constantly stirred was allowed to boil gently for 60 min. A reflux condenser was placed on the flask containing the mixture.
Few drops of phenolphthalein indicator was added to the warm solution and then titrated with 0.5M HCl to the end point until the pink colour of the indicator just disappeared. The same procedure was used for other samples and blank.
The expression for saponification value (S.V.) is given by: S.V = [56.1 N (V0-V1)]/M, where V0 = the volume of the solution used for blank test; VI = the volume of the solution used for determination; N = Actual normality of
Turkey Red oil is used in agriculture as organic manure, in textiles as surfactants and wetting agents, in paper industry for defoaming, in cosmetics as emulsifiers, in pharmaceuticals as undecylenate, in paints inks and as lubricants.
For e.g. it is used to emulsify essential oils so that they will dissolve in other water-based products, or for superfatting liquid soap if you want the soap to remain transparent. This means that the oil will combine with the water in the tub, and not leave those little oil bubbles floating on the top of the water.
It is of medium viscosity and is usually used in bath oil recipes along with fragrance or essential oils, or in shampoos. This oil also has great moisturizing abilities.
• red turkey oil
• Sulfonated tor oil
• NICOTINIC ACID ABS/TRANS STD (RSPEC0027)
• Turkey red oil sodium salt, CP,70%
• TURKEY RED OIL
• TURKEY RED OIL SODIUM SALT
• Castoroil,sulfated
• SULFATED CASTOR OIL
• sulfonated castor oil
• SULFORICINOLATE SODIUM SALT
• CASTOR-OIL SULFATED SODIUM SALT
• CASTOR OIL, SULFONATED
• sulfated caster oil
• sulfonated caster oil
• TURKEY-RED OIL 100 %
• 100ml
• CASTOROILSODIUMSALT,SULFONATED
• SULPHONATEDCASTOROIL
• Castor-oil sulfated sodium salt, Sulfated castor oil, Sulforicinolate sodium salt
• Castor oil,sulfonic
• Turkey red oil sodium salt,Castor-oil sulfated sodium salt, Sulfated castor oil, Sulforicinolate sodium salt
• Turky red oil
• Castor oil sulfonate
• Sulfonated Castor 0il
• Turkeyredoilsodiumsal
• Sulfonated castor oil ISO 9001：2015 REACH
• 8002-33-3
• C18Na2O6S
• Anionic
• BioChemical
• Detergents
1. Turkey Red Oil – Phenyl Grade.
Used in manufacture of Black Phenyl and White Phenyl. Phenyl manufacturers generally face problems of layer separation while manufacturing white phenyl. Using our Phenyl Grade Turkey Red Oil this problem is eliminated. Also quantity of Turkey Red Oil to Pine Oil decreases from 1:3 to 0.8:3 resulting in substantial savings.
2. Turkey Red Oil – Textile Grade.
Used in the process of Dyeing. Textile dyers generally face problems of oil floating on water during dyeing process, this results in the cloth getting contaminated with oil. Using our Textile Grade Turkey Red Oil this is totally eliminated.
3. Turkey Red Oil – Leather Grade.
Used in production of Leather Boards.
4. Turkey Red Oil – Metal Cutting Grade
Used in manufacture of Metal Cutting Oil.
5. Turkey Red Oil – Distillery Grade
This grade is used in Sugar Industry and Distillery as a De-foaming agent.
Skin and hair care
Castor oil has been used in cosmetic products included in creams and as a moisturizer. Small amounts of castor oil are frequently used in cold-process soap to increase lathering in the finished bar. It also has been used to enhance hair conditioning in other products and for supposed antidandruff properties.
Precursor to industrial chemicals
Castor oil can be broken down into other chemical compounds that have numerous applications. Transesterification followed by steam cracking gives undecylenic acid, a precursor to specialized polymer nylon 11, and heptanal, a component in fragrances. Breakdown of castor oil in strong base gives 2-octanol, both a fragrance component and a specialized solvent, and the dicarboxylic acid sebacic acid. Hydrogenation of castor oil saturates the alkenes, giving a waxy lubricant. Castor oil may be epoxidized by reacting the OH groups with epichlorohydrin to make the triglycidyl ether of castor oil which is useful in epoxy technology. This is available commercially as Heloxy.

The production of lithium grease consumes a significant amount of castor oil. Hydrogenation and saponification of castor oil yields 12-hydroxystearic acid, which is then reacted with lithium hydroxide or lithium carbonate to give high-performance lubricant grease.

Since it has a relatively high dielectric constant (4.7), highly refined and dried castor oil is sometimes used as a dielectric fluid within high-performance, high-voltage capacitors.
GENERAL DESCRIPTION AND APPLICATIONS:
Sulfated Castor Oil , also called castor oil acid, belong to a family of the unsaturated fatty acid. It is a viscous yellow liquid, melting at 5.5 C and boiling at 245 C. It is insoluble in water but soluble in most organic solvents. It is prepared by the hydrolysis of Castor Oil. It is used in textile finishing, in coating, inks and in making soaps.
Fatty Acids are aliphatic carboxylic acid with varying hydrocarbon lengths at one end of the chain joined to terminal carboxyl (-COOH) group at the other end. The general formula is R-(CH2)n-COOH. Fatty acids are predominantly unbranched and those with even numbers of carbon atoms between 12 and 22 carbons long react with glycerol to form lipids (fat-soluble components of living cells) in plants, animals, and microorganisms. Fatty acids all have common names respectively lilk lauric (C12), MyrIstic (C14), palmitic (C16), stearic (C18), oleic (C18, unsaturated), and linoleic (C18, polyunsaturated) acids. The saturated fatty acids have no solid bonds, while oleic acid is an unsaturated fatty acid has one solid bond (also described as olefinic) and polyunsaturated fatty acids like linolenic acid contain two or more solid bonds. Lauric acid (also called Dodecanoic acid) is the main acid in coconut oil (45 - 50 percent) and palm kernel oil (45 - 55 percent). Nutmeg butter is rich in myristic acid (also called Tetradecanoic acid ) which constitutes 60-75 percent of the fatty-acid content. Palmitic acid(also called Hexadecylic acid ) constitutes between 20 and 30 percent of most animal fats and is also an important constituent of most vegetable fats (35 - 45 percent of palm oil). Saturated carboxylic acids (C1 – C10) are liquids whereas long chain saturated fatty acids are solids. The long carbon chains form compact pile in a regular pattern with high van der waals attractions resulting in high melting points. If solid bonds are present in the fatty acid portion of the molecule, the fat is said to be unsaturated. Monounsaturated contains only one solid bond; polyunsaturated contains more than one solid bonds (up to an maximum of about six) which are never conjugated and can form geometric cis/trans isomers. Naturally occuring unsaturated fatty acids are liquids as they are in the cis- geometrical configuration which twists molecular structure (the kink of the cis form); can not pack closely, lowers melting points. Unsaturated fatty acids in the kinked, cis form are much more common in cells than the trans form continues in the same direction without a pronounced kink. The cis form of unsaturated fatty acids are more fluid at biological temperatures and are more abundant in living organisms. Fatty acids are named by the number of carbon atoms n and the number of solid bonds m as (n:m). The system for naming solid bond position is to indicate the first solid bond in the carbon backbone counting from the opposite end from the carboxyl group. The terminal carbon atom is called the omega carbon atom. The term "omega-3 or omega-6" signifies that their single solid bond is occured at carbon number 3 or 6 respectively counted from and including the omega carbon. Human bodies are not capable of synthesizing omega-3 and omega-6 fatty acids which are called essential fatty acids must be obtained through the diet. (These fatty acids were designated as "Vitamin F", until it was realized that they must be classified with the fats.) Fatty acids are converted to enegy through the process called fatty acid oxidation in liver cells. Fatty acids are used as basic building blocks of biological membranes, for long-term energy storage (the major components of triglycerides) as well as for the precursors of eicosanoid hormones.

Cosmetic Uses:
cleansing agents
humectants
surfactants
surfactant – emulsifying
Markets and applications
Lubricants and metalworking fluids, base oils, additives / Metalworking fluids
Metallurgical industry / Metalworking
Textile industry
Function
Cleansing agents
Emulsifiers
Lubricants
Wetting agents
Composition: Alkyl sulfates
Segment: Surfactants / Anionic surfactants
Alternative names: Sulfated Castor Oil, Sodium Salt, solution
SULFATED CASTOR OIL can be used as wetting agent, lubricant, dispersant, penetrant, softener and surface active agent in various chemical formulations. 

IUPAC names:
Castor oil sulfated
Castor oil, sulfated
castor oil, sulfated
Castor oil, sulfonated
sulfated castor oil
Turkey-red oil

Other identifiers:
8002-33-3