CH382144A - Verfahren zur Herstellung von Alkylsulfinaten - Google Patents

Verfahren zur Herstellung von Alkylsulfinaten

Info

Publication number: CH382144A
Authority: CH; Switzerland
Prior art keywords: converted; bis; water; alkyl; preparation
Prior art date: 1959-03-10

Application number

CH196560A

Other languages

German (de)

English (en)

Inventor

Hellmuth Dr Lehmann

Heinrich Dr Kloes

Original Assignee

Bayer 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.)

1959-03-10

Filing date

1960-02-22

Publication date

1964-09-30

1960-02-22 Application filed by Bayer Ag filed Critical Bayer Ag

1964-09-30 Publication of CH382144A publication Critical patent/CH382144A/de

Links

125000000217 alkyl group Chemical group 0.000 title claims description 6
238000000034 method Methods 0.000 title claims description 6
238000002360 preparation method Methods 0.000 title claims description 3
239000003513 alkali Substances 0.000 claims description 4
238000010438 heat treatment Methods 0.000 claims description 3
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
229940042795 hydrazides for tuberculosis treatment Drugs 0.000 claims description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 7
239000000706 filtrate Substances 0.000 description 7
239000000243 solution Substances 0.000 description 7
238000004448 titration Methods 0.000 description 7
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 6
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
229910052736 halogen Inorganic materials 0.000 description 4
QJNULWKDWXIXLJ-UHFFFAOYSA-N 1,2-bis(methylsulfonyl)ethane Chemical compound CS(=O)(=O)CCS(C)(=O)=O QJNULWKDWXIXLJ-UHFFFAOYSA-N 0.000 description 3
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 3
-1 alkyl sulfochlorides Chemical class 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
238000001816 cooling Methods 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
239000000203 mixture Substances 0.000 description 3
150000004767 nitrides Chemical class 0.000 description 3
LYPGDCWPTHTUDO-UHFFFAOYSA-M sodium;methanesulfinate Chemical compound [Na+].CS([O-])=O LYPGDCWPTHTUDO-UHFFFAOYSA-M 0.000 description 3
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
XNEFVTBPCXGIRX-UHFFFAOYSA-N methanesulfinic acid Chemical compound CS(O)=O XNEFVTBPCXGIRX-UHFFFAOYSA-N 0.000 description 2
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
JCKAPFIQSHKDSQ-UHFFFAOYSA-N 1,2-bis(ethylsulfonyl)ethane Chemical compound CCS(=O)(=O)CCS(=O)(=O)CC JCKAPFIQSHKDSQ-UHFFFAOYSA-N 0.000 description 1
MYGXWCOFMXCNRN-UHFFFAOYSA-N 1-(2-butylsulfonylethylsulfonyl)butane Chemical compound CCCCS(=O)(=O)CCS(=O)(=O)CCCC MYGXWCOFMXCNRN-UHFFFAOYSA-N 0.000 description 1
NRIUHZGWMQFPDF-UHFFFAOYSA-N 1-(2-decylsulfonylethylsulfonyl)decane Chemical compound CCCCCCCCCCS(=O)(=O)CCS(=O)(=O)CCCCCCCCCC NRIUHZGWMQFPDF-UHFFFAOYSA-N 0.000 description 1
KDQPZZDGHJSJNM-UHFFFAOYSA-N ClC1=C(C)C=C(C(=C1)S(=O)(=O)NN)[N+](=O)[O-] Chemical compound ClC1=C(C)C=C(C(=C1)S(=O)(=O)NN)[N+](=O)[O-] KDQPZZDGHJSJNM-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
238000005727 Friedel-Crafts reaction Methods 0.000 description 1
239000012359 Methanesulfonyl chloride Substances 0.000 description 1
FUXRVSQOZPLTIG-UHFFFAOYSA-N N'-methylsulfonylmethanesulfonohydrazide Chemical compound CS(=O)(=O)NNS(C)(=O)=O FUXRVSQOZPLTIG-UHFFFAOYSA-N 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
VJRITMATACIYAF-UHFFFAOYSA-N benzenesulfonohydrazide Chemical compound NNS(=O)(=O)C1=CC=CC=C1 VJRITMATACIYAF-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
CGJUVNOIOSKGHJ-UHFFFAOYSA-N butane-1-sulfinic acid;sodium Chemical compound [Na].CCCCS(O)=O CGJUVNOIOSKGHJ-UHFFFAOYSA-N 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
239000012954 diazonium Substances 0.000 description 1
150000001989 diazonium salts Chemical class 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
DCKAWKLGSBZQEC-UHFFFAOYSA-N ethanesulfonohydrazide Chemical compound CCS(=O)(=O)NN DCKAWKLGSBZQEC-UHFFFAOYSA-N 0.000 description 1
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
DOUHZFSGSXMPIE-UHFFFAOYSA-N hydroxidooxidosulfur(.) Chemical compound [O]SO DOUHZFSGSXMPIE-UHFFFAOYSA-N 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
238000002955 isolation Methods 0.000 description 1
VKHZYWVEBNIRLX-UHFFFAOYSA-N methanesulfonohydrazide Chemical compound CS(=O)(=O)NN VKHZYWVEBNIRLX-UHFFFAOYSA-N 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
DOBIKJGBGIMKEG-UHFFFAOYSA-N n'-butylsulfonylbutane-1-sulfonohydrazide Chemical compound CCCCS(=O)(=O)NNS(=O)(=O)CCCC DOBIKJGBGIMKEG-UHFFFAOYSA-N 0.000 description 1
150000002902 organometallic compounds Chemical class 0.000 description 1
230000007017 scission Effects 0.000 description 1
235000002639 sodium chloride Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
PWTKGKOPWBXLRD-UHFFFAOYSA-M sodium;decane-1-sulfinate Chemical compound [Na+].CCCCCCCCCCS([O-])=O PWTKGKOPWBXLRD-UHFFFAOYSA-M 0.000 description 1
UWIVVFQECQYHOB-UHFFFAOYSA-M sodium;ethanesulfinate Chemical compound [Na+].CCS([O-])=O UWIVVFQECQYHOB-UHFFFAOYSA-M 0.000 description 1
150000003455 sulfinic acids Chemical class 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical class OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C313/00—Sulfinic acids; Sulfenic acids; Halides, esters or anhydrides thereof; Amides of sulfinic or sulfenic acids, i.e. compounds having singly-bound oxygen atoms of sulfinic or sulfenic groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C313/02—Sulfinic acids; Derivatives thereof
- C07C313/04—Sulfinic acids; Esters thereof

Landscapes

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

CH196560A 1959-03-10 1960-02-22 Verfahren zur Herstellung von Alkylsulfinaten CH382144A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DEF27910A DE1145168B (de)	1959-03-10	1959-03-10	Verfahren zur Herstellung von chlorionenfreien waessrigen Loesungen von alkylsulfinsauren Salzen

Publications (1)

Publication Number	Publication Date
CH382144A true CH382144A (de)	1964-09-30

Family

ID=7092651

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH196560A CH382144A (de)	1959-03-10	1960-02-22	Verfahren zur Herstellung von Alkylsulfinaten

Country Status (3)

Country	Link
BE (1)	BE588508A (fr)
CH (1)	CH382144A (fr)
DE (1)	DE1145168B (fr)

1959
- 1959-03-10 DE DEF27910A patent/DE1145168B/de active Pending
1960
- 1960-02-22 CH CH196560A patent/CH382144A/de unknown
- 1960-03-10 BE BE588508A patent/BE588508A/fr unknown

Also Published As

Publication number	Publication date
DE1145168B (de)	1963-03-14
BE588508A (fr)	1960-07-01

Publication	Publication Date	Title
US2275125A (en)	1942-03-03	Nu-cyclohexyl sulphamic acid and salts
CH382144A (de)	1964-09-30	Verfahren zur Herstellung von Alkylsulfinaten
Hellerman	1927	The preparation of β-triphenylethylamine. Rearrangement of β-triphenylpropionhydroxamic acid
AT220135B (de)	1962-03-12	Verfahren zur Herstellung wässeriger Lösungen von Alkali-Alkylsulfinaten
US2273443A (en)	1942-02-17	Organic mercury compound
US3557198A (en)	1971-01-19	Process for the production of alkali metal salicylates
DE1938227A1 (de)	1971-02-11	Verfahren zur Herstellung von Mono- und Dicarbomethoxybenzolsulfonaten
Kharasch et al.	1931	The chemistry of organic gold compounds. IV. Gold imide compounds
DE1939924B2 (de)	1977-10-13	Verfahren zur herstellung von allantoin in waessrigem medium
DE904895C (de)	1954-02-22	Verfahren zur Herstellung von Salzen von Sulfonamiden
US2208641A (en)	1940-07-23	Soluble sulphanilic acid amide derivatives
US2228051A (en)	1941-01-07	Compound of hydroxyquinoline-sulphonic acids and the production thereof
DE845503C (de)	1952-07-31	Verfahren zur Herstellung von Chlormethylgruppen enthaltenden aromatischen Verbindungen
DE950286C (de)	1956-10-04	Verfahren zur Herstellung eines Hydrazons des Isonicotinsaeurehydrazids
AT243082B (de)	1965-10-25	Farbstoffbildner für das Chromogenentwicklungsverfahren
US748101A (en)	1903-12-29	Aromatic esters and process of making same.
DE572723C (de)	1933-03-22	Verfahren zur Darstellung von Chlor- und Bromderivaten der 2-Aminonaphthalin-1-sulfonsaeure
DE960985C (de)	1957-03-28	Verfahren zur Herstellung von Adipinsaeuredinitril
DE802636C (de)	1951-02-15	Verfahren zur Herstellung von Glykosiden des Sulfanilamids
DE450022C (de)	1927-09-27	Verfahren zur Darstellung von Allylarsinsaeure
SU60273A1 (ru)	1941-06-30	Способ получени 3,3'-диамино-4,4'-диоксиарсенобензола
Morgan	1958	Isolation of Two Sodium Methazonates
DE474659C (de)	1929-04-09	Verfahren zur Herstellung von reinen Nitrosamindruckfarben
DE840398C (de)	1952-06-03	Verfahren zur Herstellung der 1-Oxynaphthalin-2,3,4,6-tetrasulfonsaeure bzw. eines esterartigen Anhydrids dieser Verbindung
DE574943C (de)	1933-04-21	Verfahren zur Darstellung von Tetrazolen