US3394155A - Preparation of surface-active agents - Google Patents

Preparation of surface-active agents Download PDF

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Publication number
US3394155A
US3394155A US369597A US36959764A US3394155A US 3394155 A US3394155 A US 3394155A US 369597 A US369597 A US 369597A US 36959764 A US36959764 A US 36959764A US 3394155 A US3394155 A US 3394155A
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US
United States
Prior art keywords
acid
reaction
acids
fatty
fatty acids
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
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US369597A
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English (en)
Inventor
Cahn Arno
Lemaire Henry
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Lever Brothers Co
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Lever Brothers Co
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Publication date
Priority to US369597A priority Critical patent/US3394155A/en
Application filed by Lever Brothers Co filed Critical Lever Brothers Co
Priority to DE1965U0011731 priority patent/DE1493370A1/de
Priority to AT464865A priority patent/AT256791B/de
Priority to DK257665AA priority patent/DK114128B/da
Priority to NL656506470A priority patent/NL143560B/xx
Priority to SE6657/65A priority patent/SE324761B/xx
Priority to FR17988A priority patent/FR1434018A/fr
Priority to ES0313248A priority patent/ES313248A1/es
Application granted granted Critical
Publication of US3394155A publication Critical patent/US3394155A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
    • C07C303/22—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids

Definitions

  • coco fatty acids containing substantial quantities of the C -C fatty acids, are added in a quantity sufficient to provide the desired proportion of coco esters in the final product, but insufiicient to completely consume the hydroxy sulfonate.
  • additional fatty acid is added to provide a high conversion of the hydroxy sulfonate, the additional fatty acid, however, containing substantially lower proportions of the C3-C1Z fatty acids.
  • the present invention relates to the preparation of surface-active agents. More particularly, it relates to a process for preparing surface-active agents of the general formula RCOORSO M, where R is a monovalent aliphatic hydrocarbon radical having from 7 to 19 carbon atoms, R is selected from the group consisting of divalent aliphatic hydrocarbon radicals containing from 2 to 4 carbon atoms and aryl and alkyl-aryl radicals containing from 6 to 8 carbon atoms, and M is an alkali metal cation, the surface-active agents being prepared by the direct esterification of the corresponding hydroxy-sulfonatc.
  • RCOORSO M where R is a monovalent aliphatic hydrocarbon radical having from 7 to 19 carbon atoms, R is selected from the group consisting of divalent aliphatic hydrocarbon radicals containing from 2 to 4 carbon atoms and aryl and alkyl-aryl radicals containing from 6 to 8 carbon atoms, and M is an alkali metal cation, the
  • reaction promoter i.e., compounds which promote a high conversion of the hydroxy-sulfonate to the corresponding ester.
  • reaction promoters While the inventive concept of the present invention may be practiced Without employing them, for commercial purposes it is usually preferred that they be used.
  • Compounds having this effect include, but are not limited to, salts of strong acids and weak bases such as stannous sulfate, titanium sulfate, cadmium sulfate, tungsten phosphate; acids or acid formers such as chloroacetic acid, ethyl chloroformate, coconut fatty acid chloride, boric acid, para-toluene sulfonic acid; neutral or basic compounds such as cerium oxide, lanthanum oxide, didymium oxide, zinc oxide and zinc soaps, magnesium oxide and magnesium soaps.
  • strong acids and weak bases such as stannous sulfate, titanium sulfate, cadmium sulfate, tungsten phosphate
  • acids or acid formers such as chloroacetic acid, ethyl chloroformate, coconut fatty acid chloride, boric acid, para-toluene sulfonic acid
  • neutral or basic compounds such as cerium oxide, lanthanum oxide, didymium oxide
  • the organic acids which are suitable for the manufacture of surface-active agents may be used.
  • these are the carboxylic acids of aliphatic hydrocarbons having from 8 to 20 carbon atoms.
  • Such acids include the unsubstituted, saturated or unsaturated, straight-chain, fatty acids, such as lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, stearolic acid, acids derived from bone grease (a mixture of C fatty acids), acids derived from palm kernel oil (a mixture of C fatty acids), and acids derived from coconut oil (a mixture of C fatty acids), and acids derived from tallow (a mixture of saturated and unsaturated C fatty acids).
  • Synthetic acids such as those derived from the 0x0 and Koch processes may also be used. Aliphatic acids of the foregoing types may be used pure or may be employed as mixtures. For preparing surface-active agents, the foregoing acids should be selected so that the ultimate product will contain a major portion of C C fatty acid esters. This will normally require the use of acids having at least about 40% of the C C fatty acids.
  • R is a divalent hydrocarbon radical containing 2 to 4 carbon atoms, particularly ethylene, methylethylene, dimethylethylene, propylene or butylene.
  • R may also be an aryl or alkyl-aryl group containing from 6 to 8 carbon atoms.
  • M is preferably an alkali metal (e.g. lithium, sodium, potassium, rubidium and calcium), especially sodium or potassium.
  • the preferred second reactant may be prepared by the reaction of an epoxide, for example ethylene oxide, propylene oxide or butylene oxide, with sodium bisulfite. Examples of compounds suitable for use as the second reactant are sodium isethionate, potassium methyl isethionate, sodium dimethyl isethionate and sodium 3-hydroxypropane-sulfonate.
  • the reaction is normally carried out using an excess of the acid reactant.
  • the amount of excess acid may exceed 2. moles per mole.
  • the excess acid in addition to producing a high utilization of the hydroxy-sulfonate, assists in maintaining the product in liquid form during the reaction and in reducing formation of foam.
  • the reaction product contains significant amounts of free acid reactant.
  • the products of the reaction are generally used as detergents, such as in the manufacture of detergent tablets or the manufacture of detergent hand soaps in bar form.
  • the acids of lower molecular weight adversely affect the qualities of the detergent products.
  • the presence of the lower molecular weight fatty acids containing up to 10 carbon atoms is particularly undesirable from the standpoint of odor. These same acids are also irritating and are therefore undesirable when used in hand soap bars or other applications where mildness to the skin is desirable.
  • the C3-C12 fatty acids are undesirable because they adversely affect the plodding characteristics of the finished product. While the removal of excess free acid reactant by distillation or by neutralization is known, such processes have the disadvantage of introducing extra processing steps, or of introducing neutralization products, e.g., sodium soaps, which are not necessarily desirable.
  • acyl hydroxy-sulfonate esters of the formula RCOOR'SO M can be produced directly, containing acceptably small residues of unreacted acids of low molecular weight, by adding in successive steps two aliphatic acid reactants of the formula RCOOH.
  • the acid which is to form the major portion of the ester is reacted with the hydroxy-sulfonate.
  • This first acid includes C to C aliphatic acids of the formula RCOOH but may contain acids having from about 8 to about 20 carbon atoms.
  • coconut fatty acids are typical of the commercially useful fatty acids which may be used as the first acid.
  • the coconut fatty acids contain predominantly C to C fatty acids and contain in excess of C3 to C12 acids.
  • the reaction is allowed to proceed, after the addition of the first portion of the acid, for a period of 30 to 50 minutes at the reaction temperature. At the end of this period the first step in the preferred embodiment of the reaction will be substantially complete, although the esterification reaction will not have ceased.
  • a second aliphatic acid of higher molecular weight is added, and the reaction allowed to proceed to substantial completion.
  • Aliphatic acids suitable for use in this second step are of the formula RCOOH, and consist essentially of C to C acids. Talow fatty acids are typical of those which may be used.
  • the amount of the second acid which is added should be sufficient so that the total amount of the first and second acid reactants is at least about 1.2 moles of acid per mole of hydroxy-sulfonate. This ratio will provide for a high uilization of the hydroXy-sulfonate. In addition it will maintain the fluidity of the reaction system and will reduce the foaminess thereof as discussed above.
  • the reaction in each step is carried out at a temperature sufficient to result in a completed reaction in a reasonable time.
  • a temperature typically, in the absence of a reaction promoter, a temperature of about 200 to about 250 C. will be required. However, if a reaction promoter is employed, the maximum reaction temperature need not exceed about 240 C.
  • the amount of the fatty 3 acid added during the first step is sufficient to react with approximately 60%-80% of the hydroxy sulfonate present, yielding an initial reaction product containing from 50% to 60% ester, to free fatty acid, and 15% to 20% unreacted hydroxy-sulfonate.
  • the amount of uncombined lower molecular weight fatty acids will depend on the proportion of such acids in the acid reactant. If coconut fatty acids are employed as the reactant, these will typically be in the order of 12%15% uncombined lower molecular Weight acids.
  • the addition of the second higher molecular weight fatty acid causes the reaction to continue further toward completion, in accordance with the governing equilibria, and will produce a conversion of hydroxy-sulfonate to the corresponding ester in the order of 90%95%.
  • the first and second fatty acids are consumed at relative rates which are in substantially the same proportion to each other as the relative concentration of these acids present. Accordingly, an additional portion of unreacted fatty acid remaining from the first step .of the reaction, normally about 30%35% thereof, is converted to the corresponding ester.
  • the resulting product will contain a lower concentration of unreacted lower molecular weight fatty acid than would have resulted if the conventional, single-step process, had been employed. For instance, if coconut fatty acids and tallow fatty acids are used, as described above, in two successive steps, the resulting product will contain .in the order of 0.080.11 part of unreacted lower molecular weight fatty acids (per part of acyl hydroxy sulfonate), while had a sufiicient amount of coconut fatty acids been employed to complete the reaction in a single step, the product would contain about 0.100.l7 part of free lower molecular weight fatty acids.
  • While the present invention is particularly applicable to acyl hydroxysulfonates prepared by direct esterification employing fatty acids containings in excess of 40% C -C fatty acids, it is not to be so limited. Even when employing fatty acids containing a sufficiently low concentration of C C fatty acids that objectionable residues do not remain, an improvement in properties may be obtained by the practice of the present invention.
  • EXAMPLE 1 The following test was performed to illustrate a typical application of the step-wise addition of fatty acid reactants according to the present invention.
  • the reactor was heated on an oil bath to 230 C., all of the initial water being removed during the heating period.
  • the reaction temperature of 230 C. was maintained for 40 minutes.
  • fatty acid 2 In this illustrative example, coconut fatty acid was used as fatty acid 2 to simplify the calculations.
  • a higher weight molecular fatty acid, such as stearic acid would normally be used in its place, and would be equivalent in all respects.
  • the reaction was continued at 230 C. until water evolution ceased, indicating the end of the reaction. The termination of the reaction was verified by continuing the heating and stirring for an additional 10 minutes after cessation of water evolution.
  • Emersol 132 may be computed from these analyses. Since the Emersol 132 contained no C to C fatty acids, the amounts of these radicals appearing in TABLE III-REACTION YIELDS the product may be assigned to the coconut fatty acids.
  • lgolgrtltgio %IF1attyf' The amounts of C to C acids associated with the coco- Gl 0 1'18 080 Example Sodium Isethionate 2110, Percent Percent nut fatty acid and the Emersol 4 respectlvely y be Fm Acidl Fatty e Actlve COHWISIOII computed based on the known distribution of fatty acids (56%yCrgn) A idg a in these acids.
  • Example 2 coconut fatty acids were used as fatty acid 2 for ease of analysis and illustration.
  • Example 4 a mixture of 45% steam: and 55% palmitic acid was used as fatty acid 2.
  • Rati0 Weight of fatty acid per total weight of fatty acid-isethionate 1 and 2.
  • a method of preparing an ester of the formula RCOORSO M Where R is an aliphatic hydrocarbon having from 7 to 19 carbon atoms, R is selected from the group consisting of divalent hydrocarbon radicals containing from 2 to 4 carbon atoms and divalent aryl and alkylaryl radicals containing from 6 to 8 carbon atoms, and M is an alkali metal, comprising reacting a first acid of the formula R COOH, where R is an aliphatic hydrocarbon radical of 7 to 19 carbon atoms, said first acid including C to C acids, with a hydroxysulfonate of the formula HOR'SO M, R being as defined above, and continuing said reaction until the reaction is substantially completed, the effective ratio of said first acid to said hydroxy-sulfonate being between about 0.8 and about 1.1 moles per mole, and thereafter adding to the reaction mass a second acid of the formula R COOH, where R consists essentially of aliphatic hydrocarbon radicals of'13 to 19 carbon atoms, the total effective amount of
  • a method of preparing an ester of the formula RCOORSO M where R is an aliphatic hydrocarbon having from 7 to 19 carbon atoms, R is selected from the group consisting of divalent hydrocarbon radicals containing from 2 to 4 carbon atoms and divalent aryl and alkylaryl radicals containing from 6 to 8 carbon atoms, and M is an alkali metal comprising reacting a first acid of the formula R COOH, wherein R is an aliphatic hydrocarbon radical of 7 to 19 carbon atoms, said first acid containing a major amount of C to C acids and at least about 40% (l -C acids, with a hydroxy-sulfonate of the formula HOR'SO M, said reaction being carried to substantial completion in the presence of a reaction promoter and at a temperature between about 200 and about 240 C., the effective ratio of said first acid to said hydroxysulfonate being between about 0.8 and about 1.1 moles per mole, and thereafter adding to the reaction mass a second acid of the formula R CO

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Detergent Compositions (AREA)
US369597A 1964-05-22 1964-05-22 Preparation of surface-active agents Expired - Lifetime US3394155A (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
US369597A US3394155A (en) 1964-05-22 1964-05-22 Preparation of surface-active agents
AT464865A AT256791B (de) 1964-05-22 1965-05-21 Verfahren zur Herstellung von Estern
DK257665AA DK114128B (da) 1964-05-22 1965-05-21 Fremgangsmåde til fremstilling af acylerede hydroxysulfonater.
NL656506470A NL143560B (nl) 1964-05-22 1965-05-21 Werkwijze ter bereiding van vetzure esters van hydroxyalkaansulfonaten met de algemene formule rcoor'so3m.
DE1965U0011731 DE1493370A1 (de) 1964-05-22 1965-05-21 Verfahren zur Herstellung von oberflaechenaktiven Stoffen
SE6657/65A SE324761B (de) 1964-05-22 1965-05-21
FR17988A FR1434018A (fr) 1964-05-22 1965-05-21 Procédé de préparation d'agents tensio-actifs
ES0313248A ES313248A1 (es) 1964-05-22 1965-05-21 Un metodo para preparar un ester de formula rcoor'so3m.

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US369597A US3394155A (en) 1964-05-22 1964-05-22 Preparation of surface-active agents

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US (1) US3394155A (de)
AT (1) AT256791B (de)
DE (1) DE1493370A1 (de)
DK (1) DK114128B (de)
ES (1) ES313248A1 (de)
FR (1) FR1434018A (de)
NL (1) NL143560B (de)
SE (1) SE324761B (de)

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4405526A (en) * 1981-08-24 1983-09-20 Lever Brothers Company Process for producing directly esterified fatty acyl isethionate by a mixed zinc oxide-sulfonic acid catalyst
US4476055A (en) * 1982-07-06 1984-10-09 Westvaco Corporation C21-Dicarboxylic acid isethionates as primary anionic surfactants
JPS6041659A (ja) * 1983-05-11 1985-03-05 エシル　コ−ポレ−シヨン アシロキシベンゼンスルホン酸塩の製造方法
US4514335A (en) * 1982-07-06 1985-04-30 Westvaco Corporation C21 -Dicarboxylic acid isethionates as primary anionic surfactants
US4515721A (en) * 1982-09-27 1985-05-07 Jordan Chemical Company Process for the production of fatty acid esters of hydroxyalkyl sulfonate salts
US4571309A (en) * 1983-07-20 1986-02-18 Westvaco Corporation C22 -Cycloaliphatic tricarboxylic acid derived isethionate esters and method of preparation
US4588532A (en) * 1984-02-17 1986-05-13 Rhone-Poulenc Chimie De Base Preparation of para-acyloxybenzene sulfonates
US4588531A (en) * 1983-10-19 1986-05-13 Basf Aktiengesellschaft Preparation of alkali metal and alkaline earth metal salts of acyloxybenzenesulfonic acids
DE3442579A1 (de) * 1984-11-22 1986-05-22 Akzo Gmbh Oberflaechenaktive kondensationsprodukte
EP0220656A1 (de) * 1985-10-26 1987-05-06 Hoechst Aktiengesellschaft Kontinuierliches Verfahren zur Herstellung von Acyloxybenzolsulfonsäuren
US5100588A (en) * 1985-07-05 1992-03-31 Hoechst Aktiengesellschaft Process for the preparation of acyloxybenzenesulfonic acids and their salts
US5300665A (en) * 1992-09-16 1994-04-05 Rhone-Poulenc Surfactants And Specialties, L.P. Process for preparing fatty acid esters and amides of sulfonic acid salts
US5359127A (en) * 1987-02-26 1994-10-25 Hoechst Aktiengesellschaft Process for the preparation of acyloxyalkanesulfonates
US5384421A (en) * 1992-08-21 1995-01-24 Hoechst Celanese Corporation Process for making sodium acylisethionates
US5723432A (en) * 1992-02-05 1998-03-03 The Proctor & Gamble Company Stable pumpable liquid composition of acyloxy alkane and process for the storage thereof
US6069262A (en) * 1997-10-06 2000-05-30 Finetex, Inc. Fatty acid esters of hydroxyalkyl sulfonate salts and process for producing same
US6184399B1 (en) 1997-03-20 2001-02-06 Akzo Nobel Nv Process for preparing a fatty acyl isethionate salt
US6362145B1 (en) 2000-11-14 2002-03-26 Clariant International Ltd. Clear soap bar comprising metal catalyst sodium cocoyl isethionate

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3029264A (en) * 1958-04-29 1962-04-10 Lever Brothers Ltd Preparation of a mixture of fattyacyl-oxyalkane sulphonates

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3029264A (en) * 1958-04-29 1962-04-10 Lever Brothers Ltd Preparation of a mixture of fattyacyl-oxyalkane sulphonates

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4405526A (en) * 1981-08-24 1983-09-20 Lever Brothers Company Process for producing directly esterified fatty acyl isethionate by a mixed zinc oxide-sulfonic acid catalyst
US4476055A (en) * 1982-07-06 1984-10-09 Westvaco Corporation C21-Dicarboxylic acid isethionates as primary anionic surfactants
US4514335A (en) * 1982-07-06 1985-04-30 Westvaco Corporation C21 -Dicarboxylic acid isethionates as primary anionic surfactants
US4515721A (en) * 1982-09-27 1985-05-07 Jordan Chemical Company Process for the production of fatty acid esters of hydroxyalkyl sulfonate salts
JPS6041659A (ja) * 1983-05-11 1985-03-05 エシル　コ−ポレ−シヨン アシロキシベンゼンスルホン酸塩の製造方法
US4571309A (en) * 1983-07-20 1986-02-18 Westvaco Corporation C22 -Cycloaliphatic tricarboxylic acid derived isethionate esters and method of preparation
US4588531A (en) * 1983-10-19 1986-05-13 Basf Aktiengesellschaft Preparation of alkali metal and alkaline earth metal salts of acyloxybenzenesulfonic acids
US4588532A (en) * 1984-02-17 1986-05-13 Rhone-Poulenc Chimie De Base Preparation of para-acyloxybenzene sulfonates
DE3442579A1 (de) * 1984-11-22 1986-05-22 Akzo Gmbh Oberflaechenaktive kondensationsprodukte
US5100588A (en) * 1985-07-05 1992-03-31 Hoechst Aktiengesellschaft Process for the preparation of acyloxybenzenesulfonic acids and their salts
EP0220656A1 (de) * 1985-10-26 1987-05-06 Hoechst Aktiengesellschaft Kontinuierliches Verfahren zur Herstellung von Acyloxybenzolsulfonsäuren
US4803015A (en) * 1985-10-26 1989-02-07 Hoechst Aktiengesellschaft Continuous process for the production of acyloxybenzenesulfonic acids
US5359127A (en) * 1987-02-26 1994-10-25 Hoechst Aktiengesellschaft Process for the preparation of acyloxyalkanesulfonates
US5723432A (en) * 1992-02-05 1998-03-03 The Proctor & Gamble Company Stable pumpable liquid composition of acyloxy alkane and process for the storage thereof
US5384421A (en) * 1992-08-21 1995-01-24 Hoechst Celanese Corporation Process for making sodium acylisethionates
US5300665A (en) * 1992-09-16 1994-04-05 Rhone-Poulenc Surfactants And Specialties, L.P. Process for preparing fatty acid esters and amides of sulfonic acid salts
US6184399B1 (en) 1997-03-20 2001-02-06 Akzo Nobel Nv Process for preparing a fatty acyl isethionate salt
US6069262A (en) * 1997-10-06 2000-05-30 Finetex, Inc. Fatty acid esters of hydroxyalkyl sulfonate salts and process for producing same
US6362145B1 (en) 2000-11-14 2002-03-26 Clariant International Ltd. Clear soap bar comprising metal catalyst sodium cocoyl isethionate

Also Published As

Publication number Publication date
SE324761B (de) 1970-06-15
DK114128B (da) 1969-06-02
NL6506470A (de) 1965-11-23
DE1493370A1 (de) 1969-04-10
NL143560B (nl) 1974-10-15
ES313248A1 (es) 1965-12-16
AT256791B (de) 1967-09-11
FR1434018A (fr) 1966-04-01

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