DE1256650B - Verfahren zur Herstellung von N-acylierten 2-Amino-alkan-sulfonsaeuren-(1) bzw. von 2-Amino-alkan-sulfonsaeuren-(1) - Google Patents
Verfahren zur Herstellung von N-acylierten 2-Amino-alkan-sulfonsaeuren-(1) bzw. von 2-Amino-alkan-sulfonsaeuren-(1)Info
- Publication number
- DE1256650B DE1256650B DEA49944A DEA0049944A DE1256650B DE 1256650 B DE1256650 B DE 1256650B DE A49944 A DEA49944 A DE A49944A DE A0049944 A DEA0049944 A DE A0049944A DE 1256650 B DE1256650 B DE 1256650B
- Authority
- DE
- Germany
- Prior art keywords
- sulfonic acid
- alkane
- amino
- acid
- acylated
- 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 13
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000002253 acid Substances 0.000 claims description 12
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 8
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 4
- -1 l-butene Chemical compound 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 4
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadecene Natural products CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- JNAYPRPPXRWGQO-UHFFFAOYSA-N 2-chloropropanenitrile Chemical compound CC(Cl)C#N JNAYPRPPXRWGQO-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- OHXAOPZTJOUYKM-UHFFFAOYSA-N 3-Chloro-2-methylpropene Chemical compound CC(=C)CCl OHXAOPZTJOUYKM-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 238000006434 Ritter amidation reaction Methods 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 150000001925 cycloalkenes Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 238000010490 three component reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/08—Sulfation or sulfonation products of fats, oils, waxes, or higher fatty acids or esters thereof with monovalent alcohols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/22—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEA49944A DE1256650B (de) | 1965-08-07 | 1965-08-07 | Verfahren zur Herstellung von N-acylierten 2-Amino-alkan-sulfonsaeuren-(1) bzw. von 2-Amino-alkan-sulfonsaeuren-(1) |
| DE19651545565 DE1545565A1 (de) | 1965-08-07 | 1965-11-12 | Verfahren zur Herstellung von 3,4-Dihydro-2,2-dioxo-1,2,5-oxathiazinen |
| BE685152D BE685152A (enrdf_load_stackoverflow) | 1965-08-07 | 1966-08-05 | |
| NL6611091A NL6611091A (enrdf_load_stackoverflow) | 1965-08-07 | 1966-08-05 | |
| CH1132166A CH512445A (de) | 1965-08-07 | 1966-08-05 | Verfahren zur Herstellung von N-Acyl-2-amino-alkan-sulfonsäuren-(1) oder ihren Salzen |
| FR72326A FR1488814A (fr) | 1965-08-07 | 1966-08-05 | Procédé de préparation d'acides nu-acyl-2-amino-alcane-sulfoniques-(1), de leurs sels, esters ou amides ou d'acides 2-amino-alcane-sulfoniques-(1) |
| GB35453/66A GB1090779A (en) | 1965-08-07 | 1966-08-08 | Substituted alkane sulphonic acids and derivatives thereof |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEA49944A DE1256650B (de) | 1965-08-07 | 1965-08-07 | Verfahren zur Herstellung von N-acylierten 2-Amino-alkan-sulfonsaeuren-(1) bzw. von 2-Amino-alkan-sulfonsaeuren-(1) |
| DEA0050766 | 1965-11-12 | ||
| DEA0052177 | 1966-04-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1256650B true DE1256650B (de) | 1967-12-21 |
Family
ID=27208966
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEA49944A Pending DE1256650B (de) | 1965-08-07 | 1965-08-07 | Verfahren zur Herstellung von N-acylierten 2-Amino-alkan-sulfonsaeuren-(1) bzw. von 2-Amino-alkan-sulfonsaeuren-(1) |
| DE19651545565 Pending DE1545565A1 (de) | 1965-08-07 | 1965-11-12 | Verfahren zur Herstellung von 3,4-Dihydro-2,2-dioxo-1,2,5-oxathiazinen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19651545565 Pending DE1545565A1 (de) | 1965-08-07 | 1965-11-12 | Verfahren zur Herstellung von 3,4-Dihydro-2,2-dioxo-1,2,5-oxathiazinen |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE685152A (enrdf_load_stackoverflow) |
| CH (1) | CH512445A (enrdf_load_stackoverflow) |
| DE (2) | DE1256650B (enrdf_load_stackoverflow) |
| GB (1) | GB1090779A (enrdf_load_stackoverflow) |
| NL (1) | NL6611091A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3203692C1 (de) * | 1982-02-04 | 1983-06-09 | Standard Elektrik Lorenz Ag, 7000 Stuttgart | Fernsprechanlage |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL172650C (nl) * | 1970-02-03 | 1983-10-03 | Lubrizol Corp | Werkwijze voor het bereiden van amidoalkaansulfonzuren. |
| US3998796A (en) * | 1972-09-22 | 1976-12-21 | The Lubrizol Corporation | Nitrogen and sulfur-containing amphoteric compounds and polymers thereof |
| US3956354A (en) * | 1973-05-07 | 1976-05-11 | The Lubrizol Corporation | Method for the preparation of sulfonic acid esters from free sulfonic acids |
| US3960918A (en) * | 1973-06-26 | 1976-06-01 | The Lubrizol Corporation | Preparation of esters of amidoalkanesulfonic acids |
| FR2384751A1 (fr) * | 1977-03-23 | 1978-10-20 | Francaise Coop Pharma | Nouveaux derives de la taurine a activite neuro-musculaire renforcee |
| JPS54106427A (en) | 1978-02-09 | 1979-08-21 | Nitto Chem Ind Co Ltd | Purification of 2-acrylamide-2-methylpropane sulfonic acid |
| US6448347B1 (en) * | 1998-12-11 | 2002-09-10 | The Lubrizol Corporation | Continuous production of 2-acrylamido-2-methylpropane-sulfonic acid in a small reactor integrated with acrylic polymer fiber production |
| WO2002049991A2 (en) * | 2000-12-19 | 2002-06-27 | The Lubrizol Corporation | Aminosulfonate product-treated nitrogen-containing salt particles |
| CN106590591A (zh) * | 2015-10-20 | 2017-04-26 | 中国石油化工股份有限公司 | 采油用驱油剂组合物及其制备方法 |
| CN106589232B (zh) * | 2015-10-20 | 2020-08-07 | 中国石油化工股份有限公司 | 疏水缔合丙烯酰胺共聚物及其制备方法 |
| GB202310301D0 (en) * | 2023-07-05 | 2023-08-16 | Innospec Ltd | Compositions and method and uses related thereto |
-
1965
- 1965-08-07 DE DEA49944A patent/DE1256650B/de active Pending
- 1965-11-12 DE DE19651545565 patent/DE1545565A1/de active Pending
-
1966
- 1966-08-05 NL NL6611091A patent/NL6611091A/xx unknown
- 1966-08-05 CH CH1132166A patent/CH512445A/de not_active IP Right Cessation
- 1966-08-05 BE BE685152D patent/BE685152A/xx unknown
- 1966-08-08 GB GB35453/66A patent/GB1090779A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3203692C1 (de) * | 1982-02-04 | 1983-06-09 | Standard Elektrik Lorenz Ag, 7000 Stuttgart | Fernsprechanlage |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1090779A (en) | 1967-11-15 |
| NL6611091A (enrdf_load_stackoverflow) | 1967-02-08 |
| CH512445A (de) | 1971-09-15 |
| BE685152A (enrdf_load_stackoverflow) | 1967-01-16 |
| DE1545565A1 (de) | 1969-10-16 |
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