DE1801712A1 - Verfahren zur Herstellung nichtionischer oberflaechenaktiver Thioaetheralkohole - Google Patents
Verfahren zur Herstellung nichtionischer oberflaechenaktiver ThioaetheralkoholeInfo
- Publication number
- DE1801712A1 DE1801712A1 DE19681801712 DE1801712A DE1801712A1 DE 1801712 A1 DE1801712 A1 DE 1801712A1 DE 19681801712 DE19681801712 DE 19681801712 DE 1801712 A DE1801712 A DE 1801712A DE 1801712 A1 DE1801712 A1 DE 1801712A1
- Authority
- DE
- Germany
- Prior art keywords
- carbon atoms
- compound according
- hydroxyalkyl
- mercapto
- alkylene
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 18
- -1 thioether alcohols Chemical class 0.000 title description 5
- 238000004519 manufacturing process Methods 0.000 title description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 8
- 239000007858 starting material Substances 0.000 claims description 7
- 239000013543 active substance Substances 0.000 claims description 5
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004149 thio group Chemical group *S* 0.000 claims 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 7
- 238000005282 brightening Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 4
- GGMUJCCSBRQVTP-UHFFFAOYSA-N 1-sulfanyldodecan-2-ol Chemical compound CCCCCCCCCCC(O)CS GGMUJCCSBRQVTP-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000012459 cleaning agent Substances 0.000 description 3
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 150000002924 oxiranes Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- XXIIBORLMZZLPO-UHFFFAOYSA-N 1-sulfanylhexan-2-ol Chemical compound CCCCC(O)CS XXIIBORLMZZLPO-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229960003339 sodium phosphate Drugs 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000019635 sulfation Effects 0.000 description 1
- 238000005670 sulfation reaction Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000001226 triphosphate Substances 0.000 description 1
- 235000011178 triphosphate Nutrition 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/002—Surface-active compounds containing sulfur
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
- Y10S516/02—Organic and inorganic agents containing, except water
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Degasification And Air Bubble Elimination (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19681801712 DE1801712A1 (de) | 1968-10-08 | 1968-10-08 | Verfahren zur Herstellung nichtionischer oberflaechenaktiver Thioaetheralkohole |
| NL6913512.A NL160248C (nl) | 1968-10-08 | 1969-09-04 | Werkwijze ter bereiding van oppervlakte-actieve, zwavel bevattende epoxyalkaanadducten en oppervlakte-actieve produkten, alsmede werkwijze voor het reinigen van textiel. |
| CH1378669A CH542189A (de) | 1968-10-08 | 1969-09-10 | Verfahren zur Herstellung nichtionischer oberflächenaktiver Thioätheralkohole |
| JP44071332A JPS4928168B1 (enrdf_load_stackoverflow) | 1968-10-08 | 1969-09-10 | |
| GB4651169A GB1288239A (enrdf_load_stackoverflow) | 1968-10-08 | 1969-09-22 | |
| FR6933465A FR2020112A1 (enrdf_load_stackoverflow) | 1968-10-08 | 1969-10-01 | |
| US863350A US3661851A (en) | 1968-10-08 | 1969-10-02 | Polyalkyleneglycol ethers of hydroxyalkylmercaptans and process |
| BE739766D BE739766A (enrdf_load_stackoverflow) | 1968-10-08 | 1969-10-02 | |
| US05/578,546 USRE29243E (en) | 1968-10-08 | 1975-05-19 | Polyalkyleneglycol ethers of hydroxyalkylmercaptans and process |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19681801712 DE1801712A1 (de) | 1968-10-08 | 1968-10-08 | Verfahren zur Herstellung nichtionischer oberflaechenaktiver Thioaetheralkohole |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1801712A1 true DE1801712A1 (de) | 1970-05-21 |
Family
ID=5709886
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681801712 Pending DE1801712A1 (de) | 1968-10-08 | 1968-10-08 | Verfahren zur Herstellung nichtionischer oberflaechenaktiver Thioaetheralkohole |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3661851A (enrdf_load_stackoverflow) |
| JP (1) | JPS4928168B1 (enrdf_load_stackoverflow) |
| BE (1) | BE739766A (enrdf_load_stackoverflow) |
| CH (1) | CH542189A (enrdf_load_stackoverflow) |
| DE (1) | DE1801712A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2020112A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1288239A (enrdf_load_stackoverflow) |
| NL (1) | NL160248C (enrdf_load_stackoverflow) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3988377A (en) * | 1965-10-22 | 1976-10-26 | Lever Brothers Company | Hydroxy substituted sulfoxides and thiothers |
| USRE29243E (en) * | 1968-10-08 | 1977-05-31 | Henkel & Cie G.M.B.H. | Polyalkyleneglycol ethers of hydroxyalkylmercaptans and process |
| US3998948A (en) * | 1968-11-05 | 1976-12-21 | Societe Anonyme Dite: L'oreal | Surface active agent containing hydroxylated alkylsulfinyl chains and composition containing surface active agent having hydroxylated alkylthio and/or hydroxylated alkylsulfinyl chains |
| US3988378A (en) * | 1974-01-10 | 1976-10-26 | Ciba-Geigy Corporation | Reaction product of mercaptans, alkylene oxides and glycidol |
| ZA777510B (en) * | 1976-12-27 | 1979-01-31 | Dow Chemical Co | Froth flotation process |
-
1968
- 1968-10-08 DE DE19681801712 patent/DE1801712A1/de active Pending
-
1969
- 1969-09-04 NL NL6913512.A patent/NL160248C/xx not_active IP Right Cessation
- 1969-09-10 JP JP44071332A patent/JPS4928168B1/ja active Pending
- 1969-09-10 CH CH1378669A patent/CH542189A/de not_active IP Right Cessation
- 1969-09-22 GB GB4651169A patent/GB1288239A/en not_active Expired
- 1969-10-01 FR FR6933465A patent/FR2020112A1/fr not_active Withdrawn
- 1969-10-02 US US863350A patent/US3661851A/en not_active Expired - Lifetime
- 1969-10-02 BE BE739766D patent/BE739766A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4928168B1 (enrdf_load_stackoverflow) | 1974-07-24 |
| NL160248C (nl) | 1979-10-15 |
| NL6913512A (enrdf_load_stackoverflow) | 1970-04-10 |
| FR2020112A1 (enrdf_load_stackoverflow) | 1970-07-10 |
| CH542189A (de) | 1973-09-30 |
| BE739766A (enrdf_load_stackoverflow) | 1970-04-02 |
| US3661851A (en) | 1972-05-09 |
| GB1288239A (enrdf_load_stackoverflow) | 1972-09-06 |
| NL160248B (nl) | 1979-05-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHW | Rejection |