DE2440209A1 - BETA-SULFO-PROPIONIC ACID COMPOUNDS AND THE PROCESS FOR THEIR PRODUCTION - Google Patents

Description

24AÖ209

BASF Aktiengesellschaft

Our sign; O ₀ Z ₀ 30 756 WB / Be βγΟΟ Ludwigshafen, August 20, 1974

ß-sulfo-propionic acid compounds and processes for their

Manufacturing

The invention relates to the new ß-sulfo-propionic acid compounds and a process for their preparation by reacting alcohols, acid amides or amines with ß-sulfocarboxylic anhydrides ^

It is known from the Journal of the American Society, Volume 62, pages 2 JQ ^ to 2 397 (1940) to convert β-sulfo-propionic anhydride with methanol, ammonia or amines to give the corresponding ester or amide.

There were now the new ß-sulfo-propionic acid compounds formula

\ OR ₀ ,-SO, / ι i2 \ it ι d. - 3 R, - O-C-C- 4-R- , - \ j - L * "KjLLf lVii I - ) I C- /
η R ₂

wherein R is a straight-chain aliphatic radical with at least 4 carbon atoms, an araliphatic radical, a 2-ethylhexyl radical means the individual radicals Rp are identical or different can be and each a hydrogen atom or an aliphatic Denote remainder, R ^. for an oxygen atom or the

Radical -N-, in which R ^ denotes a hydrogen atom or an aliphatic radical, Z a hydrogen ion, the radical CH ₀ -CH ₀ R ₁ -

S), an alkali ion or the radical R ₅ -NH,

CHp-CHp R ₁ -

in which the individual radicals R ₁ - can be identical or different and each denotes an aliphatic radical or a hydrogen atom, η stands for 0 or an integer from 1 to 100, in addition also η for 0 and at the same time R ₁ and R, together 495 / 73 - 2 -

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for the rest of V

H-C -— C-R ^, in which R / - a Il j 6 6

N N-- hydroxyethyl group or a

Denotes hydrogen atom and R ₂

Rp has the above meaning, found »

It has also been found that ß-sulfo-propionic acids formula

Yes,

where R, a straight-chain aliphatic radical with at least 4 carbon atoms, an araliphatic radical, a 2-ethyl » Hexyl radical means that the individual radicals Rp are identical or different can be and each denotes a hydrogen atom or an aliphatic radical, R-, for an oxygen atom or the

Radical -N-, in which R ^. denotes a hydrogen atom or an aliphatic radical, η for 0 or an integer of 1 up to 100, beyond that η also stands for 0 and at the same time R, and R-, together for the remainder H

R ₂

can be wherein Rg represents a hydroxyethyl group or a hydrogen atom and Rp as defined above is advantageously obtained by reaction of alcohols or amines with acid anhydrides, if alcohols, amides or amines of the formula

o-C-C-j-R ^ -H II,

wherein R ,, R ₂ , R, and η have the aforementioned meaning, with

hydrides of the Forπ

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ß-sulfocarboxylic anhydrides of the formula - "5 -

24402U9

OοZ ₀ 30 756

CH ^ - SO,

ο-

III,

where Rp has the aforementioned meaning, implements »

It has also been found that the process is carried out advantageously if the β-sulfo-propionic acids Ia obtained are used with Alkali, morpholine or a base of the formula

R ₅ -N
^R.

IV,

wherein R ^ has the aforementioned meaning to ß-sulfo-propiohsäureverbindungen the formula

o-c-c-4-R,

There

S ^R 2

-CC-CH ₀ -SO, ι 2 3

H ₂

in which R ,, R ₂ , R ,, η have the aforementioned meaning and Y denotes

.CH ₀ -CH ₀ Rr-

S 2 \ 2 O Φ

O, an alkali ion or the radical R _K -NH

CHp- CHp, Rj-

means, in which the individual radicals R, - are identical or different can be and each an aliphatic radical or a hydrogen denote atom, implements.

The reaction can be used in the case of the use of sulfopropionic anhydride, Represent dodecyl alcohol and morpholine by the following formula:

' ^: , OJHi

6. "Τ T W A.

o.z. 30 756

+ OC-CH ₂ -GH ₂ -SO

CH ₂ -CH ₂

^CH 2 " ^C 5

In view of the prior art, the process according to the invention provides a large number of new β-sulfo-propionic acid ^{compounds in a simple and economical manner in the form of corresponding Es 1} IPr, monoacylamides and diacylamides in good yield and purity.

The starting materials II and III can be reacted in a stoichiometric amount or in excess, preferably in a ratio of 0.5 to 2.5 mol of starting material II per mole of starting material III. Preferred starting materials II, III and IV and correspondingly preferred end products I, Ia and Ib are those in whose formulas R _{1 is} a straight-chain alkyl radical with 4 to 26 carbon atoms, advantageously with 8 to 24, in particular with 12 to 24 carbon atoms, an alkenyl radical with 4 to 26, in particular having 8 to 24 carbon atoms, an alkylcarbonyl group having from 4 to 26, preferably 8 to 24, especially having 12 to 24 carbon atoms, aralkyl of ¹ J to 26, advantageously 10 to 24, especially from 10 to l8 carbon atoms, in particular denotes a nonylphenyl radical, an isooctylphenyl radical or an octylphenyl radical, a 2-ethylhexyl radical, the individual radicals Rp can be the same or different and each denotes a hydrogen atom or an alkyl radical with 1 to 4 carbon atoms, Η * for an oxygen atom or the radical R ₁ ,

-N- stands,

wherein R ₁ denotes a hydrogen atom, an alkyl group with 1 to 4 carbon atoms or a hydroxyethyl group, Z denotes a hydrogen ion, the remainder

CH ₀ -CH

a sodium atom or a

CH ₀ -CH ^d

biiHBiÜ / 0977
ORIGINAL iNSPECTED

O ₀ line 30 75β

_φ A

Potassium atom or the radical R, -

R _K -NH
^R 5

denotes in which the individual radicals R ₁ - can be identical or different and each denotes an alkyl radical having 1 to 26, advantageously 8 to 24, in particular 12 to 24 carbon atoms, a hydroxyethyl group or a hydrogen atom, η for 0 or an integer from 2 to 80, in addition also η for 0 and at the same time R, and R ^ together for the remainder

can stand in which Rg is a hydroxyethyl group or represents a hydrogen atom and Rp represents the aforementioned preferred meaning has "

The abovementioned radicals can still be carried out under the reaction conditions inert groups and / or atoms, eg "B" carbonamido, Cyano, nitro groups, chlorine, bromine atoms, carbalkoxy, acylamido groups each with 2 to 4 carbon atoms, alkyl groups, Alkoxy groups each having 1 to 4 carbon atoms may be substituted. Mixtures of straight-chain alcohols, as they are obtained e.g. in the oxo synthesis, implemented and the resulting mixtures of end products I directly, ζ "Β, to surfactants. This saves you the usually laborious and lossy insulation in an economical way of the individual alcohols of the mixtures. Another series of very valuable alcohols for reaction with sulfocarboxylic anhydride obtained by transalkylation of straight-chain alcohols with epoxides such as alkylene oxide and / or propylene oxide, with the alcohols in a ratio of 1 to 100 mol of alkylene oxide or mixture the epoxides are converted per mole of alcohol. If one assumes mixtures of amines, eg fatty amines such as laurylamine, then mixtures of the sulfonates of these amines with the corresponding ß-sulfopropionic acid amides are obtained,

For example, the following compounds are suitable as starting materials II: n-butyl alcohol, 2-ethylhexanol, n-octanol, decanol,

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ORIGINAL! MSPECfED

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Dodecanol, tetradecyl alcohol, octadecyl alcohol, stearic acid ethanolamide, lauric acid glycol half-ester, octylphenol, nonylphenol, dodecylphenol; Butylamine, decylamine, dodecylamine, octadecylamine, dibutylamine, methylbutylamine, methylbenzylamine, methyltetradecylamine, N-ethanol-N-butylamine; n-nonanol, n-undecanol, tridecanol, pentadecanol, hexadecanol, heptadecanol, n-tetracosanol, octadecenyl alcohol, 2-undecyl-5-hydroxyethyl-imidazoline, n-nonylamine, oleylamine, 2-ethylhexylamine, hexacosanol, lauric acid ethanolamide; the aforementioned with 2, 3 * ^> 5, 25 * 80, 100 moles of ethylene oxide or propylene oxide or moles of ethylene oxide / propylene oxide (in a ratio of 0.1 to 20 moles of propylene oxide per mole of ethylene oxide) alkoxylated alcohols, e.g., ₀ nonylphenyl-trisoxy-ethyl alcohol

CqH ₁ Q— (f V> - OCHp-CHp-4- ^ OH; or corresponding mixtures "

Possible starting materials III are: ß-sulfopropionic anhydride, ß-sulfopivalic anhydride, 2-ethylhexane ~ l-sulfonic acid-2-carboxylic acid anhydrido

The reaction is carried out usually at a temperature from 0 to 120 ⁰ C, preferably from 20 to 9O ⁰ C, under atmospheric or superatmospheric pressure, continuously or discontinuously "is expediently without solvent. However, it is also possible to use organic solvents which are inert under the reaction conditions, such as chlorinated hydrocarbons, for example ethylene chloride, chloroform; cyclic ethers, for example dioxane, tetrahydrofuran; aliphatic or aromatic hydrocarbons, such as toluene, heptane, petroleum ether, to be used.

The reaction can be carried out, for example, as follows: The sulfocarboxylic acid anhydride III is, if appropriate in a solvent, with thorough mixing with the corresponding starting material II offset. The mixture is then kept at the reaction temperature for a further 2 to 3 hours. Then the end product is in usually separated off, e.g. by distillation. More advantageous but you will neutralize the resulting sulfonic acid Ia with bases IV, alkali or morpholine and the end product Ib in the usual way Manner, for example by crystallization from suitable solvents such as alkanols, e.g. ethanol, isobutanol; Halocarbon

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2UÜ2ÜB

Hydrogen such as ethylene chloride, chloroform; Tetrahydrofuran, acetone, ethyl acetate, diethyl ether, "isolate. In the case of using amines II, the neutralization is expediently carried out by an appropriate excess of amine II. Neutralization is generally carried out at a temperature of 0 to 80 ° C., without pressure or under pressure, continuously or discontinuously, with an amount of 1 to 4, preferably 1.6 to 15 equivalents of base per mole of end product Ia for 0.1 to 12 hours. Preferred bases are sodium and potassium compounds, in particular sodium hydroxide and potassium hydroxide, morpholine, ammonia, primary Secondary or tertiary alkylamines with 1 to 26, advantageously up to 4 or 8 to 24 carbon atoms per alkyl group, for example dimethylamine, methylamine, trimethylamine, triethylamine, diethylamine, monoethylamine, propylamine, dipropylamine, tripropylamine, dibutylamine, butylamine, tributylamine, nonylamine, dinonylamine, trinonylamine , Tetracosylamine, isopropylamine, diisopropylamine, triisopropylamine, stearylamine, distearylamine , Tristearylaminj hydroxyethyl groups containing amines, for example ethanolamine, diethanolamine, triethanolamine, butyldiethanolamine, dimethylethanolamine "After the neutralization, the salt in the conventional manner, Z ₀ B. separated by filtration, ■

The new end products I which can be produced by the process of the invention are auxiliaries in the textile field, for example "detergents, Cleaning or wetting agents, dishwashing detergents, hair shampoos, emulsifiers, flotation aids, plasticizers and valuable ones Starting materials for the production of such auxiliaries, as well as dyes and pesticides, are obtained in this way with all end products of the following examples, e.g. with the mixture of dodecyl-dioxäthyl-propionäureesterß-sulfonat-sodium and tetradecyl-dioxäthyl-propionäureesterß-sulfonat-sodium (Quantity ratio 1: <l) already in a concentration of 10 to 100 parts in 1,000 parts of water very good wetting effect on cellulose material, and a very good washing effect on white washing of cotton fabrics and of Wool articles impregnated with olive oil or mineral oil. Furthermore, all end products of the following examples, e.g. the mixture of dodecyl-tris-oxethyl-propionic acid-ß-sulfonate-sodium salt and octadecyl-tris-oxäthyl-propion-

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acid-ß-sulfonate sodium salt (proportion 1: 1), in moderately foaming '"dishwashing detergents of, for example, the following composition be used;

5 parts of alkylbenzenesulfonic acid diethanolamine salt, 5 parts of nonylphenol, 10 moles of ethylene oxide 5 parts of dodecyl / octadecyl-tris-oxäthyl-propionäureester-

ß-sulfonate sodium (l: l) 5 parts isopropanol
5 parts of tetrakaiium pyrophosphate
75 parts of water

The parts mentioned in the following examples are parts by weight '

example 1

To a melt of 54.5 parts of .beta.-Sulfopropionsäureanhydrid be at 65 ⁰ C under stirring, 29.6 parts of n-butanol added. After two hours of stirring at 70 ⁰ C, the sulfonic acid I formed is by the addition of 51 * 7 parts butyldiethanolamine neutralized Man, 122 parts is obtained (83.8% of theory) propionate-.beta. (butyldiäthanolammonium) sulfonate as a brown oil "

Example 2

50 parts of 2-ethylhexanol are slowly added at 75 ° C. to a melt of 163 parts of β-sulfopropionic anhydride. After three hours of stirring at 80 ° C the mixture under stirring at 50 ⁰ C with 90 parts of 50 percent strength by weight sodium hydroxide solution to pH 5 is set Man yield receives propionic acid-2-äthylhexylesterß-sulfonatnatrium in the form of a 64 weight percent paste, which is readily soluble in water, : 265 parts (90.5 % of theory). n ^ ° = 1.4589.

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.. ^ r. "- 0.Z = 30 756

Example 3.

a) IJO parts of dodecyl alcohol are slowly added to a melt of 95 parts of β-sulfopropionic anhydride at 75 to 80 ° C. with stirring, the mixture being slightly cooled. After three hours of stirring at 85 ⁰ C to 225 parts obtained

Propionic acid dodecyl ester-ß-sulfonic acid. from Pp 36 to 38 C (from ethylene chloride).

b) 28.6 parts of morpholine are added to 96.8 parts of sulfonic acid I at 40 ° C. with stirring. The mixture is diluted with 100 parts of ethylene chloride and stirred at 60 ° C. for 2 hours. After 800 parts of petroleum ether have been added, the dodecyl propionate ß-morpholinium sulfonate which has crystallized out is filtered off with suction and recrystallized from ethanol. Pp 74-77 ° C; Yield: 100 parts (81.5 % of theory).

Example 4. ■ '■

65.5 parts of β-sulfopivalic anhydride are introduced into 74.5 parts of dodecyl alcohol at 25 ° C. with stirring. After completion the exothermic reaction slowly increases the mixture to 70.degree heated and stirred at this temperature for 3 hours. The pivalic acid dodecyl ester-ß-sulfonic acid is obtained in the form of a yellow oil of n ^ ° = 1.4563.

37 parts of morpholine are slowly added to the end product I. After diluting with 250 parts of petroleum ether, the mixture is stirred for one hour. After cooling, the suspension obtained is filtered off with suction and recrystallized from acetone “pp. 70.5 to 72 ° C .; Yield 146 parts (74.2 % of theory) of dodecyl pivalate-morpholinium sulfonate.

Example. 5

To a melt of 4l parts ß-Sulfopropionsäureanhydrid be at 65 ⁰ C with stirring 48.5 parts of a mixture of straight-chain alcohols having the composition: 27> 5 wt% 12 wt% Nonylalkoholi Decylalköhol;.. 6o, 5% Undecy percent.! Alcohol

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O ₀ line 30 756

given. After three hours of stirring at 70 ° C., the mixture is cooled and ^{neutralized at 0} ° C. with 48 parts of a 25 percent strength by weight sodium hydroxide solution. A water-soluble paste with a content of 137 parts (100 % of theory) of propionic acid onyl or decyl or undecyl ester-ß-sodium sulfonate is obtained
Mp 280-285 ⁰ C (dec.) (From acetone). The quantitative ratio of the esters corresponds to the quantitative ratio of the starting alcohols.

Example 6

To a melt of 4l Sulfopropionsaureanhydrid parts of a mixture of straight-chain alcohols having the composition are at 70 to 80 ⁰ C 64 parts 28.5 wt "$ dodecanol; 27 wt "^
Tridecanol; ., Where 23 wt ^ Tetradecanolj 21.5 wt.% Pentadecanol. After three hours of stirring at 70 ⁰ C, the present as a dark brown oil sulfonic acid I is neutralized by adding 26.5 parts of 50 percent strength by weight sodium hydroxide solution. You get
130 parts (100 % of theory) propionic acid tridecyl or dodecyl or tetradecyl or pentadecyl ester-ß-sulfonate sodium

20th
vom np = 1.46lj5o The quantitative ratio

Quantity ratio of the starting alcohols.

Example 7

20th
vom np = 1.46lj5o The proportion of the esters corresponds to this

78 parts of a mixture of n-hexadecyl alcohol and n-octadecyl alcohol (2 to 1) are added to a melt of 4 l parts of β-sulfopropionic anhydride with stirring. After three hours
Stirring at 75 ⁰ C is added, the brown melt in 350 parts of ethylene chloride and with stirring at 50 to 7O ⁰ C with
29 parts of morpholine were added. The ethylene chloride is distilled off in vacuo and the residue is recrystallized from ethanol. 142 parts (96 % of theory) of the propionic acid hexadecyl / octadecyl ester-β-sulfonic acid morpholinium salt are obtained
Form of light brown crystals. Mp 76 to 8O ⁰ C. The proportion of the ester corresponds to the proportion of the starting alcohols.

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O.Z. "30,756

Example 8.

To a melt of 4l parts Sulfopropionsaureanhydrid be at 60 to 70 ⁰ C, with stirring, 68.5 parts of a fatty alcohol mixture having the composition: 30 wt Dodecanolj 4l.Gew $ _o $ tetradecanol;. 18% by weight of hexadecanol; After three hours of stirring, the sulfonic acid I is obtained as a brown oil, which is ^{neutralized by adding 26.4 parts of 50 percent strength by weight sodium hydroxide solution at 30 °} C. By precipitating with acetone, 93 parts of propionic acid are obtained. dodecyl "or" -tetradecyl- or "hexadecyl or octadecyl _{o-ester-sulfonate-sodium} as white crystals, which are clearly water-soluble. Pp 300 ⁰ C (dec.). The quantitative ratio of the esters corresponds to the quantitative ratio of the starting alcohols.

Example 9 '

To a melt of 4l parts ß-Sulfopropionsäureanhydrid be at 50 to 70 ⁰ C, with stirring, 99.5 parts of an oxyethylated with 3 moles of ethylene oxide alcohol mixture of n-dodecyl and n-tetradecyl alcohol (55.5: 45.5) was added. After three hours of stirring at 70 ⁰ C the mixture at 40 to 70 ⁰ C and 28.6 parts of morpholine is added and stirred for a further 3 hours "is obtained 159 parts (94% der.Theorie) Propionsäure.dodecyl / tetradecyl-trisoxäthyl-ester- ß-sulfonic acid morpholinium salt

20th
as a light brown paste, n _D = 1.4598. The quantitative ratio of the esters corresponds to the quantitative ratio of the starting alcohols.

Example 10

In 133 parts of a mixture of n-dodecyl and n-tetradecyl-trisoxäthylalkohol (55: 46) 65.5 Teileß-Sulfopivalinsäureanhydrid be registered at 60 to 70 ⁰ C is obtained. 198 parts (practically quantitative) sulfonic acid I as a red-brown oil of n ^ ° = 1.4613.

By adding 39 * 5 parts of 50 percent strength by weight sodium hydroxide solution is neutralized. 237 parts (practically quantitative) of dodecyl / tetradecyl-tris-oxethyl-pivalic acid ester-ß-sulfonate

- 12 β Π 9 θ 1 0 / -Π 9- 7 7

- 12 - O.Z. 30 75β

Z44U209

sodium as a 91.6 percent aqueous solution “The quantitative ratio the ester corresponds to the quantitative ratio of the starting alcohols.

Example 11

To 227 parts of a mixture of straight-chain alcohols oxyethylated with 80 mol of ethylene oxide and having the composition: 65% by weight of hexadecanol; 35 wt. $ Octadecanol are added 9.5 parts Sulfopropionsäureanhydrid at 70 ⁰ C "After three hours of stirring at 75 to 8O ⁰ C to give the Propionsäureestersulfosäuren I as a brown oil (Ns = I, 46l7)" by the addition of 236 parts of water and 10 parts of 50 percent strength by weight sodium hydroxide solution at 4O ⁰ C until SSC is neutralized to give 482 parts of propionic acid-.beta.-sodium sulfonate mixture of the above alcohol in the form of an aqueous paste "the proportion of the ester corresponds to the proportion of the starting alcohols"

Example 12

To a melt of 129 parts of ß-sulfopropionic anhydride 378 parts of n-nonanol are added at 70 to 80 ° C with stirring, which had been oxalkylated with 3 moles of ethylene oxide and 2 moles of propylene oxide. After stirring for a further two hours at 80 ° C., one obtains 508 parts (practically quantitative) propionylnonylpentaoxalkylester-ß-sulfonic acid as brown oil (n ^ ° = 1.4590). The neutralization takes place by adding 57 parts of 50 percent strength by weight sodium hydroxide solution and 250 parts of water. 815 parts are obtained (practically ' quantitative) sodium salt in the form of a 66 percent aqueous solution.

Example 13

To a melt of 41 parts of beta-Sulfopropionsäureanhydrid be ΙΟβ parts n-tetracosanol at 60 to 70 ⁰ C under stirring. After four hours of stirring at 7O ⁰ C 147 parts are obtained (almost quantitative) Propionsäuretetracosylesterß-sulfonic acid as a brown oil (n ^ ° = 1.4537). After diluting with

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260 parts of water are added to the mixture with 24 parts of 50 percent by weight Sodium hydroxide solution neutralized. 4050 parts are obtained (practically quantitative) sodium salt in the form of a 35 cent aqueous oil.

Example 14

To 4l Sulfopropionsäureanhydrld parts 78 parts n-octadecenyl alcohol are added at 60 ° C with stirring "After three hours of stirring at 70 ⁰ C is obtained II9 parts (practically quantitative) Propionsäureoctadecenylester-.beta.-sulfonic acid as a brown oil (n ^ ⁰ = 1.4550) . At 70 ⁰ C 45 parts of triethanolamine are added "The mixture is further 2 hours at 7O ⁰ C stirred obtained 163 '1-ile (practically quantitative) paste-like triethanolamine salt.

Example 15

To 4l parts ß-Sulfopropionsäureanhydrld at 70 ⁰ C ■ Il8,5 parts Nony! Phenol, which is öxalkyliert with 4 moles of ethylene oxide, with stirring "After two hours of stirring at 75 ° C 42.8 parts at 40 ° C to 6o dibutylamine was added and the mixture is further 2 hours at 7O ⁰ C _o stirred to give 192 parts (97% of theory) propionic acid nonylphenyltetraoxäthylester-.beta.-sulfonic acid-dibutylammoniumsalz as a brown oil _(n 2 ° = 1.4904).

Example 16

To 1 ^ 0.6 parts of isooctylphenol, which are alkoxylated with 25 moles of ethylene oxide, 13.6 parts of .beta.-Sulfopropionsäureanhydrid are added with stirring at 7O ⁰ C. After J> hours bei.70 ⁰ C. 144.2 parts are obtained (practically quantitative) Endstöff Ϊ (ng ^v = 1.4847). After adding 270 parts of water, 12 parts of 50 percent strength by weight sodium hydroxide solution are added and the mixture is stirred at 40 ° C. for 2 hours. 426 parts (practically quantitative) isooctylphenyl propionate ß-sodium sulfonate are obtained as a light brown, 35 Ρϊό percent aqueous oil "

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. o "z" 50 756 ■ 244Ü2

Example I7

To 68 parts of beta-Sulfopropionsäureanhydrid are added at 8O ⁰ C 1J54 parts of 2-undecyl-5-hydroxyethyl-imidazolin "The mixture is stirred for 4 hours at 80 ° C after, wherein I98 parts (98% of theory) of N- (2 = undecyl-5-oxethyl-imidazolinyl) -propionic acid-ß-sulfonic acid is obtained, n ^ = 1.4892.,

Example l8

54.5 parts of sulfopropionic anhydride are added to a solution of 120 parts of n-nonylamine in 250 parts of ethylene chloride at 40 ° C with stirring. ^% theory) propionyl (-nonylamid) -ß-sulfonate ~ Nonylammoniumsalz be obtained in the form of colorless crystals of Pp 167-169 ⁰ C.

Example I9

To a solution of 160 parts of oleyl amine in 200 parts of ethylene chloride 4l parts Sulfopropionsäureanhydrid be at 50 to 6o ° C optionally "25 components are To the resulting red-brown oil 50 percent strength by weight sodium hydroxide solution was added after one hour and the mixture stirred for one hour at 8O ⁰ C. After cooling, the suspension is filtered off with suction and the residue is heated ^{with acetone at 56 ° C. for 0.5 hours.} Obtained I67 parts (65.5% of theory) propionyl (oleylamid-) ß-sodium sulfonate, mp 304-309 ⁰ C ₀

Example 20

To 4l parts Sulfopropionsäureanhydrid 144 parts of di- (2-ethylhexyl) amine are added with stirring at 70 to 80 ⁰ C. After two hours of stirring at 130 ⁰ C 176 parts are obtained (70% of theory) propionyl [di- (2-ethylhexyl) amide ~ j ß-sulfonic acid (di-2-ethylhexyl) ammonium salt as a brown oil from the n ^ = 1.4724.

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OoZ. 30 756

■ "■■ · 2.44U2U9

Example 21

To 136 parts of ß-sulfopropionic anhydride are added at 70 to 80.degree 243 parts of lauric acid ethanolamide are added with stirring = After three hours of stirring at 80 ° C., 379 parts are obtained (practically quantitative) Lauroylethanolamido-propionic acid-ß-sulfanic acid from n ^ ° = 1.4719.

After dilution with 250 parts of water, the mixture is neutralized with 120 parts of 50 percent strength by weight sodium hydroxide solution <, 7 ^ 3 parts (practically quantitative) of the sodium salt are obtained in the form of a 55 percent white paste »

- 16 -

'60 98 10/09 7

Claims (1)

Claims p
1 c- CC-CH ₂ -SO, where R-, a straight-chain aliphatic radical with at least 4 carbon atoms, an araliphatic radical, a 2-ethylhexyl radical, the individual radicals R _{2 can be the} same or different and each denotes a hydrogen atom or an aliphatic radical, R, for an oxygen atom or the remainder Rj, -N-, where R ₂ denotes a hydrogen atom or an aliphatic radical, Z denotes a hydrogen atom and the radical CH ₂ —CH ₂ ^ O, an alkali ion or the CH ^ -CH ^ rest means in which the individual radicals same or can be different and each denotes an aliphatic radical or a hydrogen atom, η for 0 or a whole number from 1 to 100, in addition also η for 0 and at the same time R, and R, together for the remainder H -CR ₆ can stand, where Rg is a Hydroxyäthylgrup- pe or a hydrogen atom and Rp has the aforementioned meaning ₀ H- 98 10/0977 - 17 «O, Z ₈ 30 756 ■ -. ■■■ 244U2U9 2ο Process for the production of ß-sulfo-propionic acids formula Yes, where R _{1 is} a straight-chain aliphatic radical with at least 4 carbon atoms, an araliphatic radical, a 2-ethylhexyl radical, the individual radicals Rp can be the same or different and each denote a hydrogen atom or an aliphatic radical, R-, for an oxygen atom or the remainder R ₂ , -N- is - in which R _{2 is} a hydrogen atom or denotes an aliphatic radical, η stands for 0 or an integer from 1 to 100, in addition also η for 0 and at the same time R, and R ^ ₅ together for the radical H -C-R, - ι R, can stand in which Rg is a hydroxyethyl group or a Means hydrogen atom and Rp has the aforementioned meaning, by reacting alcohols or amines with acid anhydrides, characterized in that alcohols, acid amides or Amines of the formula R- II, where R., Rp, R., and η have the aforementioned meaning, with ß-sulfocarboxylic anhydrides of the formula 0 dd CH ^ - SO, ■ 0 III, - 18 - b C 9 ß 1 0 / C O.Z. 30 756 244U2Ü9 where Rp has the aforementioned meaning, implements " Process according to Claim 2, characterized in that the ß-sulfo-propionic acids Ia obtained are mixed with alkali, morpholine or a base of the formula H
R ₅ -N Rr- IV, wherein R ₁ - has the aforementioned meaning, to ß-sulfo-propionic acid compounds of the formula OR ₀
ti t2 ? 72 OCC -) - R ^ -CC-CH ₀ -SO- 11/3 t 2 H H / η R ^ where R ,, Rp, R ^, η have the aforementioned meaning and Y denotes rest CH ₀ -CH 2 \ CHp-CHp R ₁ - , an alkali ion or the radical R ^ -N-H 5 t means in which the individual radicals Rp- are identical or different can be and each denote an aliphatic radical or a hydrogen atom. BASF Aktiengesellschaft 609810/0977