GB1059984A - Process for producing metal salts of 2-hydroxyalkane sulfonic acids - Google Patents
Process for producing metal salts of 2-hydroxyalkane sulfonic acidsInfo
- 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
Links
- 238000000034 method Methods 0.000 title abstract 4
- 150000003839 salts Chemical class 0.000 title abstract 4
- 229910052751 metal Inorganic materials 0.000 title abstract 3
- 239000002184 metal Substances 0.000 title abstract 3
- 150000003460 sulfonic acids Chemical class 0.000 title 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 10
- 229910052757 nitrogen Inorganic materials 0.000 abstract 5
- 239000002585 base Substances 0.000 abstract 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- 229910052782 aluminium Inorganic materials 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 abstract 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 abstract 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 150000001340 alkali metals Chemical class 0.000 abstract 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 2
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 abstract 2
- IIYKIPRBEOUOJY-UHFFFAOYSA-L calcium;2-hydroxyethanesulfonate Chemical compound [Ca+2].OCCS([O-])(=O)=O.OCCS([O-])(=O)=O IIYKIPRBEOUOJY-UHFFFAOYSA-L 0.000 abstract 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 abstract 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 abstract 2
- 229910052748 manganese Inorganic materials 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 abstract 2
- 229910052709 silver Inorganic materials 0.000 abstract 2
- 239000003760 tallow Substances 0.000 abstract 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- 229910052725 zinc Inorganic materials 0.000 abstract 2
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 abstract 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 abstract 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 abstract 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Chemical group 0.000 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000002723 alicyclic group Chemical group 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000004411 aluminium Substances 0.000 abstract 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 abstract 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 abstract 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- -1 heterocyclic amines Chemical class 0.000 abstract 1
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 150000004679 hydroxides Chemical class 0.000 abstract 1
- GQZXNSPRSGFJLY-UHFFFAOYSA-N hydroxyphosphanone Chemical compound OP=O GQZXNSPRSGFJLY-UHFFFAOYSA-N 0.000 abstract 1
- 229940046817 hypophosphorus acid Drugs 0.000 abstract 1
- 229910000000 metal hydroxide Inorganic materials 0.000 abstract 1
- 150000004692 metal hydroxides Chemical class 0.000 abstract 1
- 229910044991 metal oxide Inorganic materials 0.000 abstract 1
- 150000004706 metal oxides Chemical class 0.000 abstract 1
- 150000002739 metals Chemical class 0.000 abstract 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical group [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 abstract 1
- JACMPVXHEARCBO-UHFFFAOYSA-N n-pentylpentan-1-amine Chemical compound CCCCCNCCCCC JACMPVXHEARCBO-UHFFFAOYSA-N 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 abstract 1
- 235000010269 sulphur dioxide Nutrition 0.000 abstract 1
- 239000004291 sulphur dioxide Substances 0.000 abstract 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 abstract 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 abstract 1
- 230000008016 vaporization Effects 0.000 abstract 1
- 238000009834 vaporization Methods 0.000 abstract 1
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.
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)
| 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 |
-
1964
- 1964-04-22 GB GB1667864A patent/GB1059984A/en not_active Expired
- 1964-04-24 NL NL6404585A patent/NL6404585A/xx unknown
Cited By (8)
| 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 |
| US4514547A (en) * | 1982-07-06 | 1985-04-30 | Shell Oil Company | 2-Hydroxypropane sulphonic acid derivatives: their preparation and curable compositions thereof |
| US4514335A (en) * | 1982-07-06 | 1985-04-30 | 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 |
| 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 |
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