JPS6010024B2 - 光スルホン化脂肪酸エステルまたは石油パラフィンのアルカノ−ルアミン塩の連続的製造方法 - Google Patents
光スルホン化脂肪酸エステルまたは石油パラフィンのアルカノ−ルアミン塩の連続的製造方法Info
- Publication number
- JPS6010024B2 JPS6010024B2 JP57182682A JP18268282A JPS6010024B2 JP S6010024 B2 JPS6010024 B2 JP S6010024B2 JP 57182682 A JP57182682 A JP 57182682A JP 18268282 A JP18268282 A JP 18268282A JP S6010024 B2 JPS6010024 B2 JP S6010024B2
- Authority
- JP
- Japan
- Prior art keywords
- fatty acid
- alkanolamine
- photosulfonation
- starting material
- mixture
- 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 claims description 23
- 235000014113 dietary fatty acids Nutrition 0.000 title claims description 17
- 239000000194 fatty acid Substances 0.000 title claims description 17
- 229930195729 fatty acid Natural products 0.000 title claims description 17
- -1 fatty acid ester Chemical class 0.000 title claims description 17
- 239000003208 petroleum Substances 0.000 title claims description 12
- 239000012188 paraffin wax Substances 0.000 title claims description 7
- 150000003839 salts Chemical class 0.000 title claims description 4
- 238000010924 continuous production Methods 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims description 23
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 20
- 238000006277 sulfonation reaction Methods 0.000 claims description 15
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 13
- 239000007858 starting material Substances 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims description 7
- 235000019387 fatty acid methyl ester Nutrition 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 241001465754 Metazoa Species 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 3
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 3
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 claims description 3
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 2
- 230000001035 methylating effect Effects 0.000 claims description 2
- 235000013311 vegetables Nutrition 0.000 claims description 2
- 238000007872 degassing Methods 0.000 claims 1
- 235000014593 oils and fats Nutrition 0.000 claims 1
- 238000004064 recycling Methods 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 7
- HPEUJPJOZXNMSJ-UHFFFAOYSA-N Methyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC HPEUJPJOZXNMSJ-UHFFFAOYSA-N 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 150000003460 sulfonic acids Chemical class 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- CAMHHLOGFDZBBG-UHFFFAOYSA-N epoxidized methyl oleate Natural products CCCCCCCCC1OC1CCCCCCCC(=O)OC CAMHHLOGFDZBBG-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 238000004448 titration Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000003570 air Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229940043279 diisopropylamine Drugs 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 239000004071 soot Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 241000270666 Testudines Species 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- HIGRAKVNKLCVCA-UHFFFAOYSA-N alumine Chemical compound C1=CC=[Al]C=C1 HIGRAKVNKLCVCA-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003165 hydrotropic effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 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)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB08232589A GB2111275B (en) | 1982-10-18 | 1982-11-15 | Tablet input apparatus |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8120789 | 1981-11-06 | ||
| FR8120789A FR2516079A1 (fr) | 1981-11-06 | 1981-11-06 | Procede pour preparer en continu des photosulfonates d'alcanolamine a partir d'esters gras ou de paraffines de petrole et photosulfonates d'alcanolanine ainsi obtenus |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5885855A JPS5885855A (ja) | 1983-05-23 |
| JPS6010024B2 true JPS6010024B2 (ja) | 1985-03-14 |
Family
ID=9263741
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57182682A Expired JPS6010024B2 (ja) | 1981-11-06 | 1982-10-18 | 光スルホン化脂肪酸エステルまたは石油パラフィンのアルカノ−ルアミン塩の連続的製造方法 |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0080388B1 (enExample) |
| JP (1) | JPS6010024B2 (enExample) |
| DE (1) | DE3266052D1 (enExample) |
| FR (1) | FR2516079A1 (enExample) |
| NO (1) | NO823667L (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2578252B1 (fr) * | 1985-03-04 | 1987-05-15 | Dumas Inchauspe | Perfectionnement au procede pour la photosulfoxydation des n-paraffines et des esters gras methyliques |
| ES2125827B1 (es) * | 1997-02-17 | 1999-12-01 | Univ Cadiz | Procedimiento para sintetizar fotosulfanatos a partir de esteres metilicos. |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1418031A1 (de) * | 1957-03-06 | 1968-10-03 | Henri Brunel | Verfahren zur Gewinnung von oberflaechenaktiven Stoffen |
-
1981
- 1981-11-06 FR FR8120789A patent/FR2516079A1/fr active Granted
-
1982
- 1982-10-18 JP JP57182682A patent/JPS6010024B2/ja not_active Expired
- 1982-10-20 EP EP82401925A patent/EP0080388B1/fr not_active Expired
- 1982-10-20 DE DE8282401925T patent/DE3266052D1/de not_active Expired
- 1982-11-04 NO NO823667A patent/NO823667L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2516079B1 (enExample) | 1984-02-17 |
| EP0080388B1 (fr) | 1985-09-04 |
| EP0080388A1 (fr) | 1983-06-01 |
| NO823667L (no) | 1983-05-09 |
| FR2516079A1 (fr) | 1983-05-13 |
| DE3266052D1 (en) | 1985-10-10 |
| JPS5885855A (ja) | 1983-05-23 |
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