US2928860A - Inhibition of color formation during sulfation - Google Patents

Description

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United States Patent INHIBITION OF COLOR FORMATION DURIN SULFATION Robert C. Harrington, Jr., Kingsport, Tenn., as'signor to Eastman Kodak Company, Rochester, N.Y., a corporation of New Jersey No Drawing. Application May 23, 1956 Serial N0. 586,652

7 Claims. (Cl. 260-458) This invention relates to the synthesis of light colored sulfated products. More particularly it relates to an improved process wherein certain compounds may be added to the reaction for producing-sulfated fatty alcohols for inhibiting the formation of undesired color during the carrying out of said reactions.

Sulfation or sulfamation or the like treatment of various organic compounds is a well-known procedure in industry. Many procedures and materials for carrying out such type of process are described in the prior art, such as in the publication Unit Processes in Organic Synthesis, by Groggins. Also, the publication Industrial and Engineering Chemistry, for September 1954, describes a number of processes for sulfating various: compounds.

In general in the prior art the sulfating agents used are sulfuric acid, chlorosulfonic acid and sulfamic acid. While such prior art sulfating media and processes have been economical and successful for many purposes, there has resulted in many instances a darkening of the desired product.

Previous approaches to preparing light colored products have frequently dealt with the use of bleaching agents on the sulfated product after the completion of the reaction. Other methods of improving thequality of the sulfated alcohol have been concerned with the use of involved or costly methods of sulfation which require elaborate equipment, unusual conditions or call for the handling of hazardous chemicals such as liquid sulfur trioxide.

There are a number of instances in the industry whereit is desirable to have a light colored product. For ex-' ample, in the treatment of textiles where sulfated com-. pounds are frequently used, it is apparent that the employment of such sulfated compounds which do not have. a good color may tend to detract from the quality of the treated textile. It is apparent, therefore, that providing an improved process whereby sulfated products of improved color may be obtained, represents a highly desirable result. i

This invention has for an object to provide an im-'.; proved process for preparing light colored sulfated products such as light colored sulfated fatty alcohols; Still another object is to provide a relatively economical and simple method for sulfating fatty alcohols in high yields and of light color. An additional object is to provide an improved method as indicated which will produce light colored sulfated fatty alcohols which may be used for surfactants, detergents, yarn treating agents and the like purposes. A still further object is to provide an improved method for pro'dueinglight colored productsof the class indicated, which method may be carried out in highly colored products.

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product. A still further object of this invention is to provide a process which will produce light colored ammonium salts of sulfated fatty alcohols. Still another object of this invention is to provide a species of process which permits the production of light colored products and which may be applied to unsaturated long chain alcohols. Other objects will appear hereinafter.

After extensive investigation I have found that there are certain chemical compounds which I term color inhibitors which chemical compounds may be incorporated in sulfation reactions to greatly reduce the amount of color formed in these reactions. Sulfated products prepared by the method of this invention are generally uniformly light in color and retain their whiteness inthe acidic state over long periods of standing or even under the influence of moderately high temperatures. This is believed to be an unexpected result as it is well-. known that sulfated alcohols in the acidic state tend to decompose on standing. Or, such sulfated alcohols on being warmed for a short period of time tend to give While my invention in its broader aspects may be described as incorporating color inhibitors into sulfation reactions, for a better understanding of the details of my invention, I will consider my invention under the following three headings:

A. In accordance with this phase of my invention a thioamide type of compound would be added to the sulfation reaction as a color inhibitor. Examples of the compounds which have been found to be effective are as follows: thiourea, 1,3-diethyl thiourea, 1,3-dirnethyl thiourea, l-allyl thiourea, and thioacetamide.

. mechanism concerning the color inhibitor reaction is not known, it has been found that compounds of the thioamide type referred to above, namely compounds which contain a sulfur atom, and which can exist in the tautomeric form as shown below are effective color inhibitors.

in sulfation reactions of the type under consideration:

i r CNH2.:',C=NH Therefore, under this phase of my invention a thio amide type of compound as illustrated above is incorpoconventional equipment an'd with easily obtained ingredi- I to remove from or undesirable to leave in the finished rated in the sulfation reaction. That is, the alcohol to be sulfated has mixed therewith, for example, a small, amount'of the thio compound. Thereafter the sulfating agent suchas sulfuric acid is added with agitation. By this procedure wherein color inhibitor is present, the. initial formation of color bodies is bypassed and a much purer final product is made possible.

B. In accordance with this phase of my invention I have found species of process particularly adaptable to preparing ammonium salts of sulfated alcohols characterized by being light in color and having good stability under conditions of high temperature or long standing. A particularlynoteworthy aspect of this part of my invention is the application of my process to the sulfama tion of unsaturated alcohols. As far as I am aware, nowhere has the use of thio compounds of the class indicated been described as color inhibitors in the processing of unsaturated alcohols. In'accordance with this part of my invention, for example, the sulfated fatty al-' cohols are prepared much the same as in the usual manner using various known catalysts such as acetamide or urea and in addition incorporating into the reaction a color inhibitor in accordance ith the present invention.-

Sul fation reactions under this part of my invention appatently depend on the presence of a catalyst such as acetamide to drive the sulfamation to completion, while the thioamide addition in accordance with the present invention serves only to reduce the amount of color formed and apparently has little catalytic eifect on the sulfamation reaction itself. It is thought important to discuss this point in order that technical differences of the process in accordance with the present invention may be observed over the prior art.

This fact that in the present process my thioamide addition functions as a color inhibitor and not as a catalyst is amply supported by experiments which show that sulfamation of oleyl alcohol in the presence of a thioarnide of the present invention, by itself results in. little or no reaction even over extends periods of heating to relatively high temperatures, say above 120 C. The mixture resulting from this treatment in the presence of the thioamide and without a catalyst, is of relatively dark color and shows negligible sulfation activity.

On the other hand, if the same type of reaction is carried out using both a catalyst such as acetamide and a color inhibitor in accordance with the present invention, such as thiourea, the resultant product is uniformly light in color, has a high organically combined 80;; value and shows good surface activity. Here again the exact manner in which the thioamide compound of the present invention functions to reduce the amount of color is not known. However, it appears that compounds capable of existing in the tautomeric form shown below are effective in this feature of reducing color. Thiourea is one of the simplest compounds of this type. The general class of compounds may be formulated as follows:

where R can be an H, alkyl (CH CH (CH or I have further found in reactions of this type that thiourea and its derivatives are quite compatible in the reaction mixtures. Due to the fact, as mentioned above, that a sulfarnation catalyst is present, the thiourea need only serve to effect the reaction in such a manner that the final color is much lower than when no color inhibitor is used. The general reaction under this part of my invention for making ammonium salts of sulfated fatty alcohols, may be illustrated by formula as follows:

HzNSOaOH and ROH----- ROSO1ONH4 thiourea 120 0. alkyl ammonium sulfate In the above formula R represents a saturated or unsaturated aliphatic chain of 5-20 carbon atoms, and R represents an aliphatic fatty residue of 1-20 carbon atoms. While this part of my invention is particularly applicable to the treatment of unsaturated alcohols exemplified by oleyl alcohol, my invention may also be applied to other unsaturated alcohols containing from 5-20 carbon atoms in a straight or branched chain. Also my invention may be applied to saturated alcohols containing from 520 carbon atoms, examples of which are amyl, isoamyl, octyl, lauryl, octadecyl and the like. Also, certain other alcohols containing more than one primary hydroxyl group or secondary hydroxyl group in addition to the primary hydroxyl group, exemplified by decanediol-l,10 and alcohols obtained by the hydrogenation of castor oil, may be treated.

Other alcohols which may be treated are as follows: aliphatic alcohols in which the carbon chain is interrupted by other atoms or other groups such as --O--, --S--, -CO-, --CONH, --COO-, etc., examples of which are the polyalkylene glycols, alkoxy ethanols, keto alcohols, acid-amido alcohols, mono esters of glycols, etc.; and aromatic alcohols such as phenylethyl alcohol.

C. In accordance with the third part of my invention, 1 have found that inhibition of color formation during spear-see; t

sulfation or sulfamation may be accomplished by incorporating the chemical compound hydrogen peroxide into the reaction. However, the use of hydrogen peroxide is somewhat more limited in that generally it would not be used in a sulfation reaction wherein the sulfating media was essentially comprised of chlorosulfonic or sulfamic acids. Expressed in another way, I would prefer to use the hydrogen peroxide species of my invention only when the sulfating media was comprised of sulfuric acid. The reaction under this part of my invention may be illustrated by formula as shown below:

A R OH-l-HzS 04+(HzOi)--- R OS OzOH (light colored) +H10 R=saturated fatty residue A still further understanding of the details of my invention will be had from a consideration of the several examples which follow. The first group of examples, namely Example I to Xvi, are directed to operations in accord ance with part A of my invention. The next group of examples, XVII to XXI, will be for illustrating operations under part B. The remaining examples will be with regard to operations under part C. It is to be understood that these examples are set forth primarily for illustrating certain specific embodiments.

EXAMPLE I Preparation of lauryl acid sulfate.0ne mole (186 grams) of lauryl alcohol was placed in a beaker, and to it was added 1 gram of thiourea. Stirring was started, and at the same time, the addition of 1 mole (98 grams) of concentrated sulfuric acid was begun. The sulfuric acid was added at such a rate that the temperature of the reaction mixture was maintained at 50 C. After all the sulfuric acid had been added, the temperature was raised to 70 C. for 15 minutes. On analysis, the resulting lauryl acid sulfate was found to have an organically combined value of 13.73%, and a color, on 50-50 dilution with isopropanol, of 81% transmittance at 400 mu.

EXAMPLE II Preparation of lauryl acid sulfate.-A total of 10 grams of thiourea was added to 1 mole (186 grams) of lauryl.

alcohol in a beaker. Stirring was commenced and the addition of 1 mole (98 grams) of concentrated sulfuric acid started. The acid was added at such a rate that the reaction temperature was maintained at 50 C. At the end of this time, the temperature was raised to 70 C. for 15 minutes after which a sample was analyzed to give the following results. Organically combined 50;, 15.61% and 81% transmittance (on 50-50 dilution with isopropanol) at 400 mu.

EXAMPLE III Preparation of lauryl acid sulfate.--One mole (186 grams) of lauryl alcohol was placed in a beaker, and to it, with stirring, was added a sulfating mixture consisting of 5 grams of thiourea and 98 grams of concentrated sulfuric acid. The sulfating mixture was added at a rate to maintain the reaction temperature at 50 C. At the end of this time, the temperature was raised to 70 C. for 15 minutes, after which a sample was collected for analysis. The analysis showed this white sulfated product to have an organically combined 80;, value of 14.76% and a percenttransmittance at 400 mu of 92.5%.

EXAMPLE IV EXAMPLE Preparation of lauryl acid sulfate-using chlorasulfonic acid.-A sulfating mixture consisting of grams of thiourea dissolved in 1 mole (116 grams) of chlorosulalong with the analytical results are tabulated as follows:

6. Oleyl alcohol was sulfated in 'a manner similar to the examples just listed to show the applicability of these color inhibitors to unsaturated systems; The procedures,

Inhibitor Added Organit0.- Reaction cally 7 Example Color Inhibitor Suliatlng Agent Temp., Color 1 Com- Number C. bined Alcohol Sulfatlng S0,,

Agent Percent X 10 gramsthiourea Yes"... 0on0. Sulfuric.. 30 25 14 XI Yes 30 18 12 XII -.do Yes".-. Ohlorosulfonicacid-- 20 10 13 XIII 10 grams thioecetamide. Yes Cone. sulfuric 21 11 IV.. 10 grams 1-a1ly1-2- ..do-... 60 13 thlourea. XV 10 grams 1,3-dlethyl-2- do 30 47.6 12' V thiourea. XV Blan 25 0.0 I 11 1 Reported as percent transmittance at 500 mu based on 50-50 dilution of sulfated product with isopropanol. All reactions listed in this table were run using 1 mole (268 grams) oleyl alcohol and 1 mole of sulfating agent.

fonic acid was added to 1 mole (186 grams) of lauryl alcohol at a rate to maintain the reaction temperature at -40 C. When the addition of sulfating agent was complete, the reaction mixture was stirred for an additional 30 minutes while a stream of air or nitrogen was blown through it to remove the hydrogen chloride. sample of the finished material had an analysis showing 16.4% organically combined S0 and a color of 80% at 400 mu.

EXAMPLE VI EXAMPLE VII Preparation of lauryl acid sulfate using thioacetamide as a color inhibitor.-Ten grams of thioacetamide was added to 1 mole (186 grams) of lauryl alcohol, after which vigorous'stirring, and the addition of 1 mole (98 grams) of concentrated sulfuric acid was started. The acid was added at a rate to maintain a reaction temperature of 45 C. A sample of the white material obtained from this reaction showed 46% transmittance at 400 mu (on 50-50 dilution with isopropanol) and an organically combined S0 content of 14%.

EXAMPLE VIII Preparation of lauryl acid sulfate using I-allyl-Z-thiourea as a color inhibitor.0ne mole of lauryl alcohol was sulfated atf50 C. with a mixture 'of 10 grams of 1"-allyl-2'-thiou'rea in 1 mole of concentrated sulfuricacid to give an exceptionally white product having "an organically combined SOQcontent of 14.98% and 91% transmittance at 400 mu (after 50-50 dilution with isopropanol). p

' EXAMPLE IX Preparation of lauryl acid sulfateusing 1,3-diethyl-2- thiourea as a color inhibitor.0ne mole of lauryl alcohol was again sulfated at 50 C. with a mixture consisting of 10 grams of l,3-diethyl-2-thiourea dissolved in one mole (98 grams) of concentrated sulfuric acid to give a white product. On analysis, this sulfated material showed an organically combined 50;, content of 16%, and 91% transmittance at 400 mu (on 50-50 dilution with isopropanol).

The following examples are set forth in particular for.

illustrating procedures in accordance with part B of the instant invention: EXAMPLE XVII Preparation of oleyl ammonium sulfate using small per-- centages of thiourea.A mixture of 268 g. (1 mole) of oleyl alcohol, 1 g. of thiourea and 42 g. of mineral oil is placed in a beaker and stirred. The mixture is heated to 80 C. at which time 10 g. of acetamide and 100 g. of sulfamic acid are added. The temperature is then raised to 120 C. and held there for 50 minutes at which time the,

reaction is complete. The product was light in color and had a percent transmittance at 500 mu (on 50-50.

dilution with isopropanol) of and anorganieally combined S0 value of 19.6%. This product was highly surface active.

EXAMPLE XVIII Preparation of oleyl ammonium sulfate using intermediate percentages of thiourea.A mixture of 268 g. (1 mole) of oleyl alcohol, 5 g. of thiourea, and 42 g. mineral oil was placed in a beaker and heated to C. with good agitation. At this point 10 g. of acetamide was added along with g. sulfamic acid. The temperature was next raised to C. for 50 minutes to complete the reaction. A white, pasty product having a percent transmittance (on 50-50 dilution with isopropanol) at 500 muof 83% was obtained. The organically combined S0 value was 21% and the product showed high surface activity.

EXAMPLE XIX Preparation of oleyl ammonium sulfate using high percentages of thiourea.A mixture of 268 g. (1 mole) of oleyl alcohol, 42 g. of mineral oil, and 10 g. of thiourea was heated to 80 C. with agitation. At this temperature 10 g. of acetamide and 100 g. of sulfamic acid were added and the temperature raised to 120 C. for 50 minutes. The product obtained at the end of this time was light in color having 84% transmittance at 500 mu (on 50-50 dilution with isopropanol). The organically combined 80;; value was 19.8%.

EXAMPLE XX Preparation of oleyl ammonium sulfate using I-allyl- 2-thi0urea.A mixtureof 268 g. (1 mole) of oleyl alcohol, 42 g. of mineral oil, and 5 g. of 1-allyl-2-thiourea This mixture was stirredand heated to 80 C. at which time 10 g. of acetamide and 100 g. of sulfamic acid were added. The temperature was then raised to 120 C. where it was'maintained'fon 50 minutes. The product resulting from this reaction had a. percent transmittance of 83.4% at 500 mu (on 50-50 dilution with isopropanol). The organically comwas placed in a beaker.

bined 80;, value was 18.26%.

EXAMPLE XXI Preparationof lauryl ammonium sulfate.-A mixture" of 186 g. (1. mole); of lauryl alcohol, 30 g. of mineral oil, and g; of thiourea were placed in a beaker and stirred; This mixture was heated to 80' C. at which time. 5 g. of acetamide and 100 g. of sulfamic acid were added; The reaction temperature was maintained at 120 C. for 50 minutes. The resulting product was a white solid having 95.5% transmittance at 500' mu (on 50-50- dilution with isopropanol). This product alsohm an organically combined S0 value of 21.5 and was highly surface active.

In the above Examples XVI-IXXI the sulfating com.- bination used, as clearly shown in these examples, comprised sulfamic acid in conjunction with a small amount of acetamide. For convenience of reference such combination is referred to hereinafter as suifamic acid-acetamide catalyst.

Thatproceeding in accordance with my invention as described above wherein the long chain alcohol to be treated has: added thereto a color inhibitor chemical: with the beneficial. result-that an improved product is obtained, is further shown by the following tests. That is, under the first table which appears below, a sample of oleyl ammonium sulfate produced in accordance with my invention is considered. It will be. noted from this table that the transmittance percent (quality of product based on color). is very much better than product not pro duced in accordance with my invention. That is, products produced by my invention exhibit a relatively highvalue. of 84%., 83% or the like as compared with 47% for product not made, in accordance with my invention.

In the next table similar comparison is shown for lauryl ammonium sulfate produced in accordance with my' invention, having a transmittance value of around 96% as compared with a lower value for a product produced in a conventional manner.

Table I OLEYL ALIMONIUM SULFATE l At 500 mu on 50-50 dilution with isopropanol. Organically combined S0 EXAMPLE XXII Preparation of lauryl acid sulfate using dilute lauryl alcohol (high temperature).-A sulfating mixture consisting of 98 grams of concentrated sulfuric acid and 2 grams of 50% hydrogen peroxide was added slowly to a mixture consisting of 186 grams. (1 mole) of lauryl alcohol and 20 grams of mineral oii. The reaction temperaturercached 60 C. during the addition of the sulfating mixture, and was thereafter maintained at 80 C. for minutes. A light colored product was obtained from this reaction which showed high surface active properties.

EXAMPLE XXIII Preparation of lauryl acid sulfate using uming sulfuric acid-A sulfating mixture consisting of 98 grams of 15% fuming sulfuric acid and 2.5 grams of 50% hydrogen peroxide was added slowly, and with good agitation, to a mixture consisting of 186 grams of lauryl alcohol and 20 gramsv of mineral oil. The temperature was allowed to reach a maximum of 45 C. during the addition of the sulfating mixture, but was then raised to. 60 C.. for 3.0 minutes, after which it was cooled to room temperature. The resulting product was very light in color, had a percent transmission of 85% at 500 mu, and showed strong surface active properties.

EXAMPLE XXIV Preparation of lauryl acid sulphate (high peroxide content, high temperature).A sulfating mixture consisting of 98 grams of concentrated sulfuric acid and 5 grams of 50%. hydrogen peroxide was added to 186 grams of lauryl alcohol with good agitation. The temperature reached 55 C. during the addition, and was then raised to C, for 15 minutes, after which the product was cooled to room temperature. A white material was obtained. which showed 14% organically combined sulfur trioxide and 100% transmission at 500 mu. Lauryl acid sulfate prepared by this method showed the usual surface active properties.

EXAMPLE XXVI Preparation of lauryl acid sulfate (intermediate peroxide content, high temperature) .-A sulfating'mixture consistof 98 grams of concentrated sulfuric acid and 3 grams of 50% hydrogen peroxide was added with good agitation to 136 grams of lauryl alcohol. The temperature of the reaction medium was kept at 70 C. for 15 minutes after addition of the sulfating mixture and then cooled to roomtemperature. The: resulting product was a white. solid, had an organically combined sulfur trioxide content of 14%, and a percent transmission of 100% at 500 mu.

- EXAMPLE XXVIII Preparationof lauryl acid sulfate (low peroxide content; low z'empemture).-A sulfati'ngmixture consisting of 98 grams of concentrated sulfuric acid and 1 gram of 50% hydrogen peroxide was added with agitation to 1.86 grams of lauryl alcohol. The temperature of the reaction reached 50 C. during this addition, and was held at 50 C. for an additional 15 minutes. The cooled product was white in color and showed transmis- The resulting product sion at 500 mu. The organically combined sulfur trioxide was 15% and the compound was highly surface active.

EXAMPLE XXIX Preparation of lauryl acid sulfate (low peroxide content, high temperature).-A sulfating mixture consisting of 98 grams concentrated sulfuric acid and 1 gram of 50% hydrogen peroxide was added with strong agitation to 186 grams of lauryl alcohol. The temperature reached 55 C. during this addition, but was raised to. 70 C. and

V held there for 15 minutes after the addition was'complete. The white product obtained from this reaction had an organically combined sulfur trioxide content of 15% and a transmission of 99% at 500 mu.

In order to permit clearer understanding of the results obtained by this method of synthesis, the analytical values are listed in tabular form as follows:

Examination of this table clearly shows the beneficial efiect that the inclusion of hydrogen peroxide in the sulfating mixture has. Using reaction conditions consisting of a hydrogen peroxide content of 0.5 gram to 2.5 grams per mole of concentrated sulfuric acid and a temperature range of 50-70" C., these variations still give a white product having a high organically combined sulfur trioxide content and good stability on storage in the acidic state.

The particular and practical utility of my invention enabling the production of lighter'colored sulfated products is apparent to a substantial extent merely from the visual inspection of the products obtained. However, these benefits are further apparent when sulfated'alcohols are used in textile treating compositions. A textile treating composition was made up containing 2% of light color sulfated lauryl alcohol produced in accordance with the present invention. This treating composition was applied to continuous filament 150 denier cellulose acetate yarn. No darkening of the yarn was observed due to this initial application. After a period of six months the yarn thus treated was examined. No darkening of the yarn was noted after this extended period. The amount of the color inhibitor added by weight and with respect to the weight of the alcohol being processed, would be from the relatively small amount of 0.1% to the higher amount such as 20%.

As may be seen from the above examples using the improved process of the present invention, in many instances the temperature of sulfation can be kept within the range above room temperature but below 100 C. The maximum temperature which'would be employed generally will not exceed 150 C. A suitable temperature range is from 50 to 130 C. The reaction time in general, as indicated by the above examples, is only from V2 hour to two hours. The maximum time of reaction "in general will not exceed about 4 hours. As indicated in the examples, I prefer to thoroughly agitate the sulfating media with the compound being sulfated.

I claim:

1. The process of sulfating long-chain alcohols to ob tain a product of improved color, which comprises incorporating with the alcohols 0.l20%, with respect to the weight of the alcohol, of a color inhibitor from the group consisting of thiourea, diethyl thiourea, dimethyl thiourea, allyl thiourea and thioacetamide, agitating the aforesaid mixture, incorporating into the mixture 21. sulfat ing agent from the group consisting of sulfuric acid,

chlorosulfonic acid, and sulfamic acid-acetamide catalyst, holding the temperature of the reaction within the range from room temperature to 150 C., and after the reaction has taken place, isolating the sulfated alcohol product of improved color.

2. The process in accordance with claim 1 wherein the long-chain alcohol is lauryl alcohol and the temperature is maintained between 50l30 C.

3. The process of preparing lauryl sulfate of improved color which comprises mixing lauryl alcohol with not more than 10% by weight of thiourea as a color inhibitor, sulfating the aforementioned mixtures with sulfuric acid while maintaining the temperature within the range of 50-130 C.

4. The process of producing an oleyl sulfate exhibiting a transmittance (at 500 mu on 50-50 dilution with isopropanol) of greater than 58%, which comprises adding 0.l20%, with respect to the weight of the alcohol, of a compound from the group consisting of thiourea, diethyl thiourea, dimethyl thiourea, allyl thiourea and thioacetamide as a color inhibitor to the oleyl alcohol to be sulfated, then treating the mixture of alcohol and color inhibitor with sulfuric acid while maintaining, the temperature between 50-130 C.

5. The process in accordance with claim 4 wherein the sulfating agent is chlorosulfonic acid.

6. The process of sulfating an alcohol containing 10-20 carbon atoms which comprises reacting the alcohol in the presence of 0.l20%, with respect to the weight of the alcohol, of a color inhibitor from the group consisting of thiourea, diethyl thiourea, dimethyl thiourea, allyl thiourea and thioacetamide incorporated with the alcohol, and in the presence of a sulfating agent from the group consisting of sulfuric acid, chlorosulfonic acid and sulfamic acid-acetamide catalyst, maintaining the, temperature of the reaction between 50-130 C. and isolating the sulfated alcohol of improved color.

7. The process of producing a sulfate product of improved color from an alcohol from the group consisting of lauryl alcohol and oleyl alcohol which comprises mixing the alcohol with 0. 1-20%, with respect to the weight of the alcohol, of a color inhibitor from the group consisting of thiourea, diethyl thiourea, dimethyl thiourea,

allyl thiourea and thioacetamide, also incorporating a content of mineral oil, agitating the aforesaid components and heating them to approximately C. and then adding sulfamic acid and acetamide, raising the temperature to approximately C. and thereafter isolating reaction products of improved color.

References Cited in the file of this patent UNITED STATES PATENTS

Claims (1)

1. THE PROCESS OF SULFATING LONG-CHAIN ALCOHOLS TO OBTAIN A PRODUCT OF IMPROVED COLOR, WHICH COMPRISES INCORPORATING WITH THE ALCOHOLS 0.1-20%, WITH RESPECT TO THE WEIGHT OF THE ALCOHOL, OF A COLOR INHIBITOR FROM THE GROUP CONSISTING OF THIOUREA, DIETHYL THIOUREA, DIMETHYL THIOREA, ALLYL THIOUREA AND THIOACETAMIDE, AGITATING THE AFORESAID MIXTURE, INCORPORTING INTO THE MIXTURE A SULFATING AGENT FROM THE GROUP CONSISTING OF SULFURIC ACID, CHLOROSULFONIC ACID, AND SULFAMIC ACID-ACETAMIDE CATALYST, HOLDING THE TEMPERATURE OF THE REACTION WITHIN THE RANGE FROM ROOM TEMPERATURE TO 150*C., AND AFTER THE REACTION HAS TAKEN PLACE, ISOLATING THE SULFATED ALCOHOL PRODUCT OF IMPROVED COLOR.