GB406380A - Improvements in the manufacture and production of aminoalkyl sulphonic acids - Google Patents

Improvements in the manufacture and production of aminoalkyl sulphonic acids

Info

Publication number
GB406380A
GB406380A GB2451232A GB2451232A GB406380A GB 406380 A GB406380 A GB 406380A GB 2451232 A GB2451232 A GB 2451232A GB 2451232 A GB2451232 A GB 2451232A GB 406380 A GB406380 A GB 406380A
Authority
GB
United Kingdom
Prior art keywords
obtainable
acid
heating
sulphuric
autoclave
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
Application number
GB2451232A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Priority to GB2451232A priority Critical patent/GB406380A/en
Publication of GB406380A publication Critical patent/GB406380A/en
Expired legal-status Critical Current

Links

Landscapes

  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Aminoalkylsulphonic acids, of the general formula <FORM:0406380/IV/1> , where R and R1 are hydrogen or any hydrocarbon radicle, or jointly, with the nitrogen atom, a heterocyclic nucleus, and R2 is an alkylene group, are manufactured by reacting mineral acid esters of hydroxyalkylamines, or salts thereof, with neutral alkali metal, alkaline earth metal or ammonium salts of sulphurous acid in the presence of some water. The quantity of water may be very small, traces thereof being sufficient, but usually the quantity should be at least equal to that of the mineral acid ester and preferably to that of both reaction components. Neutral or acid esters, or water soluble salts of the latter, from strong non-oxidizing mineral acids, e.g. sulphuric and phosphoric acids and halogen hydracids, are preferred, those from weak acids such as boric acid or from nitric acid being less suitable. Particularly suitable are the acid sulphuric esters of hydroxyalkylamines, obtainable for example by the process of Specification 377,695, or salts thereof, e.g. acid sulphuric esters of mono-, di- or triethanolamine, N-hydroxyethylaniline, N-ethyl-N-hydroxyethylaniline, N-hydroxyethyldiphenylamine (obtainable by heating diphenylamine in an autoclave with ethylene oxide), N-hydroxyethyl-N-benzylamine, N-hydroxyethylpiperidine, N-methyl-N - hydroxyethyl - N - octodecenylamine (obtainable by heating octodecenyl alcohol sulphuric ester with excess of methylamine in a closed vessel and heating the N-methyloctodecenylamine produced with ethylene oxide in an autoclave), N - hydroxyisopropyl - N - methyl - a -naphthylamine (obtainable by heating N-methyl - a - naphthylamine with a - propylene oxide), N - b - hydroxy - n - butyl - N - ethylaniline (obtainable by heating N-ethylaniline with 1 : 2-butylene oxide in a closed vessel), N-b -hydroxy-n-butyl-a - or b -naphthylamine (obtainable similarly from a - or b -naphthylamine), N - b - hydroxy - n - butyldiphenylamine (obtainable similarly from diphenylamine), N - g - hydroxy - n - butyl - N - benzyl - N - n - butylamine (obtainable by heating N-benzyl-N-n-butylamine with 1 : 3-butylene oxide in a closed vessel), N - g - hydroxypropylcyclohexylamine (obtainable by heating cyclohexylamine with 1 : 3-propylene oxide in a closed vessel), N-hydroxyethyl - N - benzylcyclohexylamine (obtainable by heating N-benzylcyclohexylamine with ethylene oxide in a closed vessel), N - butyl - N - b - hydroxypropylaniline (obtainable by heating N-butylaniline with 1 : 2-propylene oxide in a closed vessel) and similar N-aryl-N-hydroxyalkylamines of the general formula NRR1R2, where R is hydrogen or any alkyl, cycloalkyl, aryl or aralkyl radicle, R1 is an aryl or aralkyl radicle, e.g. phenyl, tolyl, xylyl, naphthyl or benzyl, and R2 is a hydroxyalkyl radicle. There may also be employed the corresponding halogen hydracid esters, e.g. butyl chlor-, brom- or iodoethylamine (obtainable by heating butylethanolamine in an autoclave with fuming hydrochloric, hydrobromic or hydriodic acid, in the last case in the presence of red phosphorus), or phosphoric esters or water-soluble salts thereof, especially the alkali metal salts. When employing acid mineral acid esters the reaction mixture is preferably neutralized by means of alkali. The reaction is generally carried out by warming in aqueous solution in a closed vessel, generally to about 120--180 DEG C., though in some cases the temperature should not exceed 160 DEG C. in order to avoid decomposition of the initial materials. Water-soluble, neutral and inert organic diluents, e.g. ethyl alcohol, glycol or acetone, may be added. Suitable sulphites are ammonium, sodium, potassium, lithium, calcium, barium, strontium and magnesium sulphites, especially the first three. The sulphites are advantageously employed in slight excess over the theoretical quantity. The products are intermediates for the preparation of assistants for the textile and related industries, dyestuffs and pharmaceutical preparations. In examples: (1) aminoethanol monosulphuric ester is heated with sodium sulphite in aqueous solution in an autoclave to produce taurine; (2) N - n - butyl - N - hydroxyethylaniline sulphuric ester (obtainable by heating N-n-butylaniline with ethylene oxide, mixing the product with concentrated sulphuric acid and pouring on to ice) is dissolved in water, neutralized with caustic soda and heated in an autoclave with sodium sulphite, yielding N-butyl-N-phenyltaurine sodium salt; (3) the sodium salt of N-methyl-N-hydroxyethylaniline sulphuric ester is heated in aqueous solution in a pressure-tight vessel with sodium sulphite, producing N-methyl-N-phenyltaurine sodium salt; (4) the sodium salt of N-hydroxyethyl-N-benzylaniline sulphuric ester (obtainable by heating N-benzylaniline in a closed vessel with ethylene oxide, treating the product with concentrated sulphuric acid and pouring on to ice) is heated in aqueous solution in a closed vessel with sodium sulphite, to yield N-benzyl-N-phenyltaurine sodium salt; (5) the acid sulphuric ester of N-ethyl-N-hydroxyethyl-a -naphthylamine (obtainable by heating N-ethyl-a -naphthylamine in an autoclave with ethylene oxide and treating the product with concentrated sulphuric acid) is dissolved in water, neutralized with caustic soda and heated in an autoclave with sodium sulphite to produce N-ethyl-N-a -naphthyltaurine, which is liberated by addition of sulphuric acid; (6) the sodium salt of the acid sulphuric ester of N-hydroxyethyldiphenylamine (obtainable by treating N-hydroxyethyldiphenylamine with concentrated sulphuric acid, pouring on to ice, neutralizing with caustic soda and evaporating to dryness) is heated in an autoclave in aqueous solution with sodium sulphite, yielding diphenyltaurine sodium salt.
GB2451232A 1932-09-02 1932-09-02 Improvements in the manufacture and production of aminoalkyl sulphonic acids Expired GB406380A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB2451232A GB406380A (en) 1932-09-02 1932-09-02 Improvements in the manufacture and production of aminoalkyl sulphonic acids

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2451232A GB406380A (en) 1932-09-02 1932-09-02 Improvements in the manufacture and production of aminoalkyl sulphonic acids

Publications (1)

Publication Number Publication Date
GB406380A true GB406380A (en) 1934-03-01

Family

ID=10212815

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2451232A Expired GB406380A (en) 1932-09-02 1932-09-02 Improvements in the manufacture and production of aminoalkyl sulphonic acids

Country Status (1)

Country Link
GB (1) GB406380A (en)

Similar Documents

Publication Publication Date Title
US1932907A (en) Process of preparing aminoalkylsulphonic acids
US2830082A (en) N-(hydroxyalkyl) taurine compounds and method of preparation
US2137314A (en) Process of producing quaternary ammonium compounds
US2018792A (en) Process for the manufacture of hydroxypyrene
US2647117A (en) Preparation of nitrogen-containing materials from olefins
US2106716A (en) Sulphonated alkyl-aryloxyalkylols
GB406380A (en) Improvements in the manufacture and production of aminoalkyl sulphonic acids
US2069336A (en) Production of derivatives of polyhydric alcohols
US2414706A (en) Methods for production of alkali metal trifluoracetate
US1999432A (en) Production of aminoalkyl sulphonic acids
GB875846A (en) Baths for the production of electrolytic metal coatings
US2567676A (en) Production of guanidine sulfate
US3277163A (en) Process for preparing bis-hydroxyalkylsulfones and beta-hydroxyalkylsulfonic acid salts
US2375733A (en) Preparation of dithioammelide
SU504490A3 (en) The method of obtaining derivatives of theophylline
US2542965A (en) Preparation of dihydrocoumarins
US2433542A (en) Sulfuric acid esters and a process of making same
GB759331A (en) Manufacture of basic polyglycol ethers and their use
US2413968A (en) Process for manufacture of nu-alkyl glycines
GB1067762A (en) Production of amines
US2809966A (en) Aminobenzene-sulphoiyyl-z-amino-
US3392185A (en) Process of sulfating alkoxylated derivatives of aliphatic alcohols and phenols
US2676984A (en) Preparation of guanidine from ammonium thiocyanate
US978145A (en) Organic mercury compound.
US2653976A (en) Guanidine sulfate from urea and sulfur dioxide