GB1059984A - Process for producing metal salts of 2-hydroxyalkane sulfonic acids - Google Patents

Process for producing metal salts of 2-hydroxyalkane sulfonic acids

Info

Publication number
GB1059984A
GB1059984A GB1667864A GB1667864A GB1059984A GB 1059984 A GB1059984 A GB 1059984A GB 1667864 A GB1667864 A GB 1667864A GB 1667864 A GB1667864 A GB 1667864A GB 1059984 A GB1059984 A GB 1059984A
Authority
GB
United Kingdom
Prior art keywords
formula
oxide
reacted
nitrogen
nitrogen base
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
GB1667864A
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.)
GAF Chemicals Corp
Original Assignee
General Aniline and Film Corp
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 General Aniline and Film Corp filed Critical General Aniline and Film Corp
Publication of GB1059984A publication Critical patent/GB1059984A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)

Abstract

Metal salts of 2-hydroxyalkane sulphonic acids of the formula HOCHR-CHR1SO3M, wherein R and R1 each represent a hydrogen atom or an alkyl radical and M represents an alkali metal, alkaline earth metal or Ag, Zn, Mn or Al cation are obtained by reacting ammonia or a volatile amine of the formula R2N(R3)R4, wherein R2 R3 and R4 are as hereinafter defined with sulphur dioxide in the presence of water, to form a bisulphite which is then reacted with an alkylene oxide to give the salt of the nitrogen base of 2-hydroxyalkane sulphonate of the formula <FORM:1059984/C2/1> wherein R2, R3 and R4 each represent hydrogen or an alkyl, alkenyl, alicyclic, or aryl or any two of R2, R3 and R4 form with the N atom a heterocyclic radical; which is then reacted with a metal hydroxide or oxide selected from the alkali metals, alkaline earth metals or Ag, Zn, Mn or Al in the presence of water and the nitrogen base removed by vaporization. The above process may be carried out continuously, the nitrogen base being recovered from the process and reused. Suitable nitrogen bases include methylamine, dimethylamine, trimethylamine, ethylamine, diethylamine, triethylamine, propylamine, dipropylamine, tripropylamine, butylamine, dibutylamine, tributylamine, amylamine, diamylamine, hexylamine, cyclohexylamine, octylamine, dodecylamine, aniline, methyl aniline, their isomers and their mixtures, and also heterocyclic amines of the formula <FORM:1059984/C2/2> where X represents oxygen, sulphur, nitrogen or a methylene radical, m represents 2 or 3 and n represents an integer of 1 to 3. Specific examples include morpholine and piperidine. Unsaturated heterocyclic compounds such as pyridine and quinoline may also be used. Specified alkylene oxides include ethylene oxide, propylene oxide, butylene oxide, their isomers and their mixtures. Salts of those metals which on hydrolysis yield hydroxides may be used provided objectionable anions are not produced, e.g. aluminium isopropylate. Examples are given and an example is also given in which calcium isethionate prepared according to the process is reacted with tallow acid in the presence of hypophosphorus acid to give the tallow ester of calcium isethionate.
GB1667864A 1963-04-25 1964-04-22 Process for producing metal salts of 2-hydroxyalkane sulfonic acids Expired GB1059984A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US27549463A 1963-04-25 1963-04-25

Publications (1)

Publication Number Publication Date
GB1059984A true GB1059984A (en) 1967-02-22

Family

ID=23052542

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1667864A Expired GB1059984A (en) 1963-04-25 1964-04-22 Process for producing metal salts of 2-hydroxyalkane sulfonic acids

Country Status (2)

Country Link
GB (1) GB1059984A (en)
NL (1) NL6404585A (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0098623A1 (en) * 1982-07-06 1984-01-18 Shell Internationale Researchmaatschappij B.V. 2-Hydroxypropane sulphonic acid derivatives; their preparation and curable compositions containing them
US4476055A (en) * 1982-07-06 1984-10-09 Westvaco Corporation C21-Dicarboxylic acid isethionates as primary anionic surfactants
US4499028A (en) * 1982-09-07 1985-02-12 Witco Chemical Corporation Preparation of isethionic acid
US4514335A (en) * 1982-07-06 1985-04-30 Westvaco Corporation C21 -Dicarboxylic acid isethionates as primary anionic surfactants
US4571309A (en) * 1983-07-20 1986-02-18 Westvaco Corporation C22 -Cycloaliphatic tricarboxylic acid derived isethionate esters and method of preparation
US5646320A (en) * 1993-10-28 1997-07-08 Henkel Corporation Process for making isethionate ester salts
US5763632A (en) * 1993-10-28 1998-06-09 Henkel Corporation Process for making isethionate ester salts

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0098623A1 (en) * 1982-07-06 1984-01-18 Shell Internationale Researchmaatschappij B.V. 2-Hydroxypropane sulphonic acid derivatives; their preparation and curable compositions containing them
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
US4514547A (en) * 1982-07-06 1985-04-30 Shell Oil Company 2-Hydroxypropane sulphonic acid derivatives: their preparation and curable compositions thereof
US4499028A (en) * 1982-09-07 1985-02-12 Witco Chemical Corporation Preparation of isethionic acid
US4571309A (en) * 1983-07-20 1986-02-18 Westvaco Corporation C22 -Cycloaliphatic tricarboxylic acid derived isethionate esters and method of preparation
US5646320A (en) * 1993-10-28 1997-07-08 Henkel Corporation Process for making isethionate ester salts
US5763632A (en) * 1993-10-28 1998-06-09 Henkel Corporation Process for making isethionate ester salts

Also Published As

Publication number Publication date
NL6404585A (en) 1964-10-26

Similar Documents

Publication Publication Date Title
GB1064169A (en) Surface active sulpho compounds
GB1059984A (en) Process for producing metal salts of 2-hydroxyalkane sulfonic acids
US3084187A (en) Substituted aminoalkanesulfonic acids
GB1094205A (en) Process for the preparation of amino-acid surface active agents
US4276224A (en) Anthraquinone sulphonamide compounds and preparation
EP0446971B1 (en) Process for the preparation of substituted sulphonic acids and/or sulphonates
US2345061A (en) Organic compound and process for producing the same
GB1459830A (en) Process for the preparation of thiocarbamic acid o-esters
US3406202A (en) Preparation of aniline thioethers
US2694723A (en) Xanthogenato-sulfonates and process for the preparation of mercaptoalkanesulfonates
GB2008588A (en) Recovering salts of aspartic acid
US2670369A (en) Phosphonamic acids
US3200127A (en) 2-amino-1 sulfonic acids
US4579687A (en) Process for producing salt of alpha-sulfo fatty acid alkyl ester
GB848463A (en) Improvements in the manufacture of surface-active acylated hydroxy sulphonates
US2346569A (en) Reaction of saturated hydrocarbon carboxylic acids with admixed sulphur dioxide and chlorine
US2524084A (en) Peroxidic sulfonic acids and salts
US2559585A (en) Preparation of sulfonic acid compounds
US3258474A (en) Amphoteric alpha-sulfo fatty amides and a method of producing them
US3041338A (en) 5-hydroxy substituted tetrahydro-pyrimidines
EP0102140A1 (en) Catalyzed preparation of amines from alkyl sulfates
US3200139A (en) beta-sulfatosulfonamides
US2574554A (en) Bis carbonyl dithiophosphate compounds
US2402823A (en) Surface-active agents
US2921083A (en) Organic thiosulfates