CA1187893A - Manufacture of acyl isethionates - Google Patents
Manufacture of acyl isethionatesInfo
- Publication number
- CA1187893A CA1187893A CA000409951A CA409951A CA1187893A CA 1187893 A CA1187893 A CA 1187893A CA 000409951 A CA000409951 A CA 000409951A CA 409951 A CA409951 A CA 409951A CA 1187893 A CA1187893 A CA 1187893A
- Authority
- CA
- Canada
- Prior art keywords
- acid
- sulphonic acid
- organic
- isethionate
- sulphonic
- 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
- -1 acyl isethionates Chemical class 0.000 title claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 title description 3
- 239000003054 catalyst Substances 0.000 claims abstract description 17
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000000194 fatty acid Substances 0.000 claims abstract description 11
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 10
- 229930195729 fatty acid Natural products 0.000 claims abstract description 10
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 10
- 239000000203 mixture Substances 0.000 claims abstract description 9
- 150000003751 zinc Chemical class 0.000 claims abstract description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 44
- 239000011787 zinc oxide Substances 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 19
- 150000007513 acids Chemical class 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 230000003197 catalytic effect Effects 0.000 claims description 9
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical class OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 3
- 239000004711 α-olefin Substances 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 150000004996 alkyl benzenes Chemical class 0.000 claims description 2
- 239000012188 paraffin wax Substances 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims 1
- 239000011701 zinc Substances 0.000 description 10
- 229940045998 sodium isethionate Drugs 0.000 description 8
- LADXKQRVAFSPTR-UHFFFAOYSA-M sodium;2-hydroxyethanesulfonate Chemical compound [Na+].OCCS([O-])(=O)=O LADXKQRVAFSPTR-UHFFFAOYSA-M 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 229910001220 stainless steel Inorganic materials 0.000 description 5
- 239000010935 stainless steel Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 230000007797 corrosion Effects 0.000 description 4
- 238000005260 corrosion Methods 0.000 description 4
- 239000003599 detergent Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000004448 titration Methods 0.000 description 3
- LRDIEHDJWYRVPT-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC(O)=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 LRDIEHDJWYRVPT-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 238000010960 commercial process Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- 229910000619 316 stainless steel Inorganic materials 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 101001003194 Eleusine coracana Alpha-amylase/trypsin inhibitor Proteins 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 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
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 241001272720 Medialuna californiensis Species 0.000 description 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- UREZNYTWGJKWBI-UHFFFAOYSA-M benzethonium chloride Chemical compound [Cl-].C1=CC(C(C)(C)CC(C)(C)C)=CC=C1OCCOCC[N+](C)(C)CC1=CC=CC=C1 UREZNYTWGJKWBI-UHFFFAOYSA-M 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 229910001651 emery Inorganic materials 0.000 description 1
- 150000002190 fatty acyls Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229940045996 isethionic acid Drugs 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- CXKWCBBOMKCUKX-UHFFFAOYSA-M methylene blue Chemical compound [Cl-].C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 CXKWCBBOMKCUKX-UHFFFAOYSA-M 0.000 description 1
- 229960000907 methylthioninium chloride Drugs 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- YZYKBQUWMPUVEN-UHFFFAOYSA-N zafuleptine Chemical compound OC(=O)CCCCCC(C(C)C)NCC1=CC=C(F)C=C1 YZYKBQUWMPUVEN-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/295,943 US4405526A (en) | 1981-08-24 | 1981-08-24 | Process for producing directly esterified fatty acyl isethionate by a mixed zinc oxide-sulfonic acid catalyst |
| US295,943 | 1981-08-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1187893A true CA1187893A (en) | 1985-05-28 |
Family
ID=23139896
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000409951A Expired CA1187893A (en) | 1981-08-24 | 1982-08-23 | Manufacture of acyl isethionates |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4405526A (https=) |
| EP (1) | EP0073626B1 (https=) |
| BR (1) | BR8204913A (https=) |
| CA (1) | CA1187893A (https=) |
| DE (1) | DE3271376D1 (https=) |
| ES (1) | ES8306105A1 (https=) |
| IN (1) | IN156363B (https=) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4476055A (en) * | 1982-07-06 | 1984-10-09 | Westvaco Corporation | C21-Dicarboxylic acid isethionates as primary anionic surfactants |
| 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 |
| US4536338A (en) * | 1983-11-09 | 1985-08-20 | Lever Brothers Company | Process for manufacture of fatty acid esters of hydroxy sulfonates |
| DE3706232A1 (de) * | 1987-02-26 | 1988-09-08 | Hoechst Ag | Verfahren zur herstellung von acyloxialkansulfonaten |
| US5739365A (en) * | 1991-06-26 | 1998-04-14 | Ppg Industries, Inc. | Method for preparing ammonium hydroxyalkyl sulfonates and ammonium alkanoyl alkyl sulfonates produced therefrom |
| US5384421A (en) * | 1992-08-21 | 1995-01-24 | Hoechst Celanese Corporation | Process for making sodium acylisethionates |
| 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 |
| US5523432A (en) * | 1994-04-07 | 1996-06-04 | Henkel Kommanditgesellschaft Auf Aktien | Process for the production of quaternary ammonium salts of fatty acid hydroxyalkanesulfonic acids |
| US5473089A (en) * | 1994-04-14 | 1995-12-05 | Henkel Kommanditgesellschaft Auf Aktien | Process for the production of ammonium fatty acid hydroxyalkanesulfonates |
| US5496959A (en) * | 1994-05-23 | 1996-03-05 | Hoechst Celanese Corporation | Preparation of N-acyl taurates |
| DE19640573A1 (de) * | 1996-10-01 | 1998-04-02 | Clariant Gmbh | Tensidmischungen mit einem Gehalt an Acyloxialkansulfonaten |
| US6069262A (en) * | 1997-10-06 | 2000-05-30 | Finetex, Inc. | Fatty acid esters of hydroxyalkyl sulfonate salts and process for producing same |
| US6362145B1 (en) | 2000-11-14 | 2002-03-26 | Clariant International Ltd. | Clear soap bar comprising metal catalyst sodium cocoyl isethionate |
| US6963004B2 (en) * | 2003-12-23 | 2005-11-08 | Unilever Home & Personal Care Usa, Division Of Conopco, Inc. | Process for making directly esterified fatty acid isethionate using group 4 metal based, particularly zirconium based catalysts |
| JP4607704B2 (ja) * | 2005-08-23 | 2011-01-05 | 第一工業製薬株式会社 | アルコキシル化用触媒及びアルコキシレートの製造方法 |
| US20100005706A1 (en) | 2008-07-11 | 2010-01-14 | Innospec Fuel Specialties, LLC | Fuel composition with enhanced low temperature properties |
| US9593298B2 (en) | 2011-06-20 | 2017-03-14 | Innospec Limited | Composition comprising fatty acyl isethionate and synthetic wax and method producing the same |
| CN121064069A (zh) | 2016-09-28 | 2025-12-05 | 联合利华知识产权控股有限公司 | Defi和酰胺牛磺酸盐的混合物及其制备方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE559839A (https=) * | 1956-08-09 | |||
| GB824447A (en) * | 1956-08-10 | 1959-12-02 | Gen Aniline & Film Corp | Improved process of preparing anionic surface active agents |
| GB848463A (en) * | 1957-05-10 | 1960-09-14 | Unilever Ltd | Improvements in the manufacture of surface-active acylated hydroxy sulphonates |
| US3004049A (en) * | 1959-12-01 | 1961-10-10 | Gen Aniline & Film Corp | Production of ester type anionic surface active agents |
| US3320292A (en) * | 1963-09-05 | 1967-05-16 | Lever Brothers Ltd | Preparation of sulfonated fatty acid ester surface-active agents |
| US3383396A (en) * | 1963-10-30 | 1968-05-14 | Lever Brothers Ltd | Preparation of surface-active agents using a dissolved zirconium catalyst |
| US3394155A (en) * | 1964-05-22 | 1968-07-23 | Lever Brothers Ltd | Preparation of surface-active agents |
| US3429136A (en) * | 1964-12-11 | 1969-02-25 | Lever Brothers Ltd | Process for preparing hydroxy sulfonate esters |
| US3880897A (en) * | 1973-09-13 | 1975-04-29 | Gillette Co | Method of making acyl esters of hydroxy alkane sulfonates |
-
1981
- 1981-08-24 US US06/295,943 patent/US4405526A/en not_active Expired - Lifetime
-
1982
- 1982-08-11 IN IN212/BOM/82A patent/IN156363B/en unknown
- 1982-08-23 EP EP82304437A patent/EP0073626B1/en not_active Expired
- 1982-08-23 DE DE8282304437T patent/DE3271376D1/de not_active Expired
- 1982-08-23 ES ES515185A patent/ES8306105A1/es not_active Expired
- 1982-08-23 BR BR8204913A patent/BR8204913A/pt not_active IP Right Cessation
- 1982-08-23 CA CA000409951A patent/CA1187893A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US4405526A (en) | 1983-09-20 |
| EP0073626A3 (en) | 1984-03-28 |
| EP0073626A2 (en) | 1983-03-09 |
| IN156363B (https=) | 1985-07-06 |
| EP0073626B1 (en) | 1986-05-28 |
| ES515185A0 (es) | 1983-05-01 |
| ES8306105A1 (es) | 1983-05-01 |
| BR8204913A (pt) | 1983-08-02 |
| DE3271376D1 (en) | 1986-07-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1187893A (en) | Manufacture of acyl isethionates | |
| EP2217688B1 (en) | Isomerized alpha olefin sulfonate and method of making the same | |
| US3234258A (en) | Sulfation of alpha olefins | |
| JP2787777B2 (ja) | 内部オレフインスルホネートの製造方法 | |
| US4536338A (en) | Process for manufacture of fatty acid esters of hydroxy sulfonates | |
| JPS6059903B2 (ja) | 内部オレフインスルホン酸塩の製造法 | |
| CA1287839C (en) | PROCESS FOR THE PRODUCTION OF MOBILE PASTES OF WASHING-ACTIVE .alpha.-SULFOFATTY ACID ESTER SALTS OF HIGH SOLIDS CONTENT | |
| CA1273353A (en) | Preparation of acyloxy benzene sulfonate | |
| US5252770A (en) | Process for the production of carbonate esters | |
| US3980588A (en) | Detergents containing olefin sulfonate | |
| US4299965A (en) | Preparation of benzotriazole | |
| US4061603A (en) | Detergents | |
| JPS59122454A (ja) | α−スルホ脂肪酸アルキルエステル塩の製造法 | |
| US4910335A (en) | Decolorization of alkanesulfonic and arenesulfonic acids | |
| US4309317A (en) | Clear aqueous olefin sulfonate solution | |
| JPS63132997A (ja) | 洗浄性ビルダ−およびビルダ−入り洗剤 | |
| US4279786A (en) | Homogeneous aqueous alpha-olefin sulfonate composition | |
| JP3376676B2 (ja) | α−スルホ脂肪酸アルキルエステル塩の製造方法 | |
| IE47145B1 (en) | Method for hydrolysis of casein | |
| EP0690838B1 (en) | Process to manufacture alkylbenzenesulphonic acid | |
| KR0141413B1 (ko) | 알파 술포지방산 에스테르염의 표백방법 | |
| SU576038A3 (ru) | Способ получени галоидангидридов моногалоидуксусной кислоты | |
| US2849450A (en) | Manufacture of salts of alkyl acid sulfates in one step | |
| SU859357A1 (ru) | Способ получени аллилсульфоната натри | |
| JPS5925369A (ja) | α−スルホ脂肪酸エステルの漂白方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEC | Expiry (correction) | ||
| MKEX | Expiry |