WO1996028417A1 - Synthesis of bleach activators - Google Patents
Synthesis of bleach activators Download PDFInfo
- Publication number
- WO1996028417A1 WO1996028417A1 PCT/US1996/002887 US9602887W WO9628417A1 WO 1996028417 A1 WO1996028417 A1 WO 1996028417A1 US 9602887 W US9602887 W US 9602887W WO 9628417 A1 WO9628417 A1 WO 9628417A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- acid
- phenol sulfonate
- process according
- conducted
- acid halide
- Prior art date
Links
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
-
- 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
- C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
Definitions
- the present invention relates to the chemical synthesis of organic compounds which are useful as activators in fabric bleaches and laundry compositions
- amido bleach activators are prepared using economical synthetic methods which employ water as one of the principal reaction solvents Additional benefits of the present invention include the ability to use short reaction times and low reaction temperatures, both of which help achieve reaction products having excellent light or white color
- the present invention encompasses a process for preparing phenol sulfonate esters of hydrocarboyl ammo acids, comprising the steps of
- step (b) reacting the ammo acid halide of step (a) with a phenol sulfonate in the presence of water and base
- Step (a) of the process herein can be conducted using an inorganic acid halide selected from the group consisting of SOCI2, PCI3, PCI5, POCI3 and their corresponding bromides, or oxalyl chloride (COCI)2
- SOCI2 is not too harsh for use with reactants having an amido group, provides improved yields of the corresponding carboxylic acid chlo ⁇ de, and is thus preferred for use in step (a)
- step (b) is conducted in a reaction medium which comprises a two-phase mixture of water and an organic solvent, most preferably using the reaction conditions disclosed hereinafter
- the organic solvent is chosen from those which are compatible with (1 e , non-reactive with) the ammo acid halide formed in step (a)
- Ether solvents, hydrocarbon solvents and the like are useful for this purpose Alcohols, amines and other solvents which could react with the ammo acid halide are avoided All percentages ratios and proportions herein are by weight, unless otherwise specified All documents cited are in relevant part incorporated herein by reference DETAILED DESCRIPTION OF THE INVENTION The process herein is conducted using reagents and conditions as disclosed more fully hereinafter The overall reaction sequence is shown below for the synthesis of the "NACA-OBS" activator
- Step (a) of the reaction herein is conducted as noted hereinafter, typically at room temperature (15°C-25°C)
- Step (b) of the reaction herein is conducted at about 5°C to about 20°C and at a pH range of about 9 to about 12 2, preferably about 10-11 It has now been discovered that this pH range for the reaction medium is critical to allow the phenol sulfonate reactant to be present in its anionic form, yet not be so alkaline as to hydrolyze the desired reaction product
- reaction is virtually instantaneous, and can be monitored, if desired, by the pH drop in the aqueous solvent phase As the pH drops, additional base is added to maintain the pH in the range noted
- NACA-OBS and NAAA-OBS mate ⁇ als can be formulated in combination with known bleaching ingredients such as percarbonate, persulfate, and other peroxy materials to provide cleaning compositions
- bleaching ingredients such as percarbonate, persulfate, and other peroxy materials
- EXAMPLE III A granular bleach composition suitable for use in fab ⁇ c faunde ⁇ ng and general- purpose cleaning operations is as follows
- Zeolite A (0 1-10 micron) 28 0
- optical brightener and protease includes optical brightener and protease, cellulase, lipase and amylase enzymes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Fats And Perfumes (AREA)
- Jet Pumps And Other Pumps (AREA)
- Compounds Of Unknown Constitution (AREA)
Abstract
Description
Claims
Priority Applications (12)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DK96910359T DK0815075T3 (en) | 1995-03-15 | 1996-03-04 | Synthesis of pale activators |
EP96910359A EP0815075B1 (en) | 1995-03-15 | 1996-03-04 | Synthesis of bleach activators |
AT96910359T ATE198322T1 (en) | 1995-03-15 | 1996-03-04 | PRODUCTION OF BLEACH ACTIVATORS |
BR9607470A BR9607470A (en) | 1995-03-15 | 1996-03-04 | Synthesis of bleach activators |
CA002214117A CA2214117C (en) | 1995-03-15 | 1996-03-04 | Synthesis of bleach activators |
SK1092-97A SK109297A3 (en) | 1995-03-15 | 1996-03-04 | Synthesis of bleach activators |
MXPA/A/1997/007037A MXPA97007037A (en) | 1995-03-15 | 1996-03-04 | Synthesis of activators of blanq |
DE69611356T DE69611356T2 (en) | 1995-03-15 | 1996-03-04 | MANUFACTURE OF BLEACH ACTIVATORS |
AU53572/96A AU5357296A (en) | 1995-03-15 | 1996-03-04 | Synthesis of bleach activators |
PL96322212A PL322212A1 (en) | 1995-03-15 | 1996-03-04 | Method of obtaining brigtening agent activators |
NO974095A NO308357B1 (en) | 1995-03-15 | 1997-09-05 | Process for the preparation of the phenolic sulfonate ester of hydroxycarboylamino acids |
GR20010400028T GR3035214T3 (en) | 1995-03-15 | 2001-01-11 | Synthesis of bleach activators |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/404,654 US5523434A (en) | 1995-03-15 | 1995-03-15 | Synthesis of bleach activators |
US08/404,654 | 1995-03-15 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1996028417A1 true WO1996028417A1 (en) | 1996-09-19 |
Family
ID=23600487
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1996/002887 WO1996028417A1 (en) | 1995-03-15 | 1996-03-04 | Synthesis of bleach activators |
Country Status (24)
Country | Link |
---|---|
US (1) | US5523434A (en) |
EP (1) | EP0815075B1 (en) |
AT (1) | ATE198322T1 (en) |
AU (1) | AU5357296A (en) |
BR (1) | BR9607470A (en) |
CA (1) | CA2214117C (en) |
CZ (1) | CZ291279B6 (en) |
DE (1) | DE69611356T2 (en) |
DK (1) | DK0815075T3 (en) |
EG (1) | EG20957A (en) |
ES (1) | ES2153099T3 (en) |
GR (1) | GR3035214T3 (en) |
HU (1) | HUP9801398A3 (en) |
IL (1) | IL117394A (en) |
MA (1) | MA23825A1 (en) |
NO (1) | NO308357B1 (en) |
PL (1) | PL322212A1 (en) |
PT (1) | PT815075E (en) |
RU (1) | RU2158256C2 (en) |
SK (1) | SK109297A3 (en) |
TR (1) | TR199700951T1 (en) |
TW (1) | TW330196B (en) |
WO (1) | WO1996028417A1 (en) |
ZA (1) | ZA962057B (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2001038298A1 (en) * | 1999-11-25 | 2001-05-31 | Siemens Axiva Gmbh & Co. Kg | Method for isolating amido acid phenyl ester sulfonates out of water-solvent mixtures |
US6720441B2 (en) | 1999-11-25 | 2004-04-13 | Siemens Axiva Gmbh & Co. Kg | Recovery and purification of substituted benzenesulfonates |
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---|---|---|---|---|
US6207843B1 (en) | 1996-12-17 | 2001-03-27 | The Procter & Gamble Company | Process for the preparation of N-(alkanoyl) aminoalkanoyloxy benzenesulfonates |
CA2300943A1 (en) | 1997-08-20 | 1999-02-25 | The Procter & Gamble Company | Process for preparing and/or purifying amido acid phenyl ester sulfonates |
AR016969A1 (en) | 1997-10-23 | 2001-08-01 | Procter & Gamble | PROTEASE VARIANTE, ADN, EXPRESSION VECTOR, GUEST MICROORGANISM, CLEANING COMPOSITION, ANIMAL FOOD AND COMPOSITION TO TREAT A TEXTILE |
GB9726246D0 (en) * | 1997-12-11 | 1998-02-11 | Ass Octel | Preparation of esters |
GB9726247D0 (en) * | 1997-12-11 | 1998-02-11 | Ass Octel | Preparation of esters |
US6420331B1 (en) * | 1998-06-10 | 2002-07-16 | Procter & Gamble Company | Detergent compositions comprising a mannanase and a bleach system |
EP0982291B1 (en) * | 1998-07-31 | 2003-03-26 | Clariant GmbH | Process for the preparation of phenyl esters of amidocarboxylic acids |
WO2000031028A2 (en) | 1998-11-20 | 2000-06-02 | The Procter & Gamble Company | Improved synthesis of bleach activators |
DE19900939C2 (en) * | 1999-01-13 | 2001-06-07 | Clariant Gmbh | Process for the preparation of amido acid phenyl esters |
DE60032487T2 (en) | 1999-07-16 | 2007-10-04 | The Procter & Gamble Company, Cincinnati | MEDIUM-CHAINED TENSIDES AND ZWITTERIONIC POLYAMINE-CONTAINING LAUNDRY DETECTIVE COMPOSITIONS |
US6448431B1 (en) | 1999-09-13 | 2002-09-10 | Eastman Chemical Company | Production of aryl carboxylate esters |
US6696401B1 (en) * | 1999-11-09 | 2004-02-24 | The Procter & Gamble Company | Laundry detergent compositions comprising zwitterionic polyamines |
US6812198B2 (en) | 1999-11-09 | 2004-11-02 | The Procter & Gamble Company | Laundry detergent compositions comprising hydrophobically modified polyamines |
BR0015451A (en) | 1999-11-09 | 2002-07-09 | Procter & Gamble | Laundry detergent compositions comprising hydrophobically modified polyamines |
EP1292566A2 (en) | 2000-06-02 | 2003-03-19 | Eastman Chemical Company | Process for hydrolyzing amido-carboxylic acid esters into amido-carboxylic acids |
US6660712B2 (en) * | 2000-06-02 | 2003-12-09 | Dale Elbert Van Sickle | Stabilization of amido acids with antioxidants |
US6498124B2 (en) | 2000-06-02 | 2002-12-24 | Eastman Chemical Company | Isolation of phenyl ester salts from mixtures comprising sulfolane |
US6500973B2 (en) | 2000-06-02 | 2002-12-31 | Eastman Chemical Company | Extractive solution crystallization of chemical compounds |
ATE286876T1 (en) | 2000-06-02 | 2005-01-15 | Eastman Chem Co | PHENYL ESTER SALTS PURIFICATION |
GB2366564A (en) * | 2000-08-30 | 2002-03-13 | Procter & Gamble | Preparation of Esters and Amides |
AU2002239475A1 (en) | 2000-10-27 | 2002-05-27 | The Procter And Gamble Company | Stabilized liquid compositions |
DE10139663A1 (en) * | 2001-08-11 | 2003-02-20 | Clariant Gmbh | High quality acyloxybenzene sulfonate production from low quality phenol sulfonates is catalysed by basic nitrogen-containing compounds |
DE10145223A1 (en) | 2001-09-13 | 2003-04-03 | Basf Ag | Process for the preparation of meso-zeaxanthin |
DE10233827A1 (en) * | 2002-07-25 | 2004-02-12 | Clariant Gmbh | Process for the preparation of acyloxybenzenesulfonates |
DE10300981A1 (en) * | 2003-01-14 | 2004-07-22 | Clariant Gmbh | Process for the preparation of acyloxybenzenesulfonates |
US20080177089A1 (en) | 2007-01-19 | 2008-07-24 | Eugene Steven Sadlowski | Novel whitening agents for cellulosic substrates |
US8558051B2 (en) * | 2007-07-18 | 2013-10-15 | The Procter & Gamble Company | Disposable absorbent article having odor control system |
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US20110240510A1 (en) | 2010-04-06 | 2011-10-06 | Johan Maurice Theo De Poortere | Optimized release of bleaching systems in laundry detergents |
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Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4634551A (en) * | 1985-06-03 | 1987-01-06 | Procter & Gamble Company | Bleaching compounds and compositions comprising fatty peroxyacids salts thereof and precursors therefor having amide moieties in the fatty chain |
EP0294073A1 (en) * | 1987-06-02 | 1988-12-07 | Interox Chemicals Limited | Preparation of esters |
WO1994028106A1 (en) * | 1993-05-20 | 1994-12-08 | The Procter & Gamble Company | Bleaching compounds comprising peroxyacid activators used with enzymes |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4852989A (en) * | 1987-05-08 | 1989-08-01 | The Procter & Gamble Company | Bleaching compounds and compositions comprising fatty peroxyacids salts thereof and precursors therefor having amide moieties in the fatty chain |
-
1995
- 1995-03-15 US US08/404,654 patent/US5523434A/en not_active Expired - Fee Related
-
1996
- 1996-03-04 DE DE69611356T patent/DE69611356T2/en not_active Expired - Fee Related
- 1996-03-04 HU HU9801398A patent/HUP9801398A3/en unknown
- 1996-03-04 EP EP96910359A patent/EP0815075B1/en not_active Expired - Lifetime
- 1996-03-04 AU AU53572/96A patent/AU5357296A/en not_active Abandoned
- 1996-03-04 AT AT96910359T patent/ATE198322T1/en not_active IP Right Cessation
- 1996-03-04 RU RU97117099/04A patent/RU2158256C2/en active
- 1996-03-04 TR TR97/00951T patent/TR199700951T1/en unknown
- 1996-03-04 CA CA002214117A patent/CA2214117C/en not_active Expired - Fee Related
- 1996-03-04 DK DK96910359T patent/DK0815075T3/en active
- 1996-03-04 PT PT96910359T patent/PT815075E/en unknown
- 1996-03-04 ES ES96910359T patent/ES2153099T3/en not_active Expired - Lifetime
- 1996-03-04 SK SK1092-97A patent/SK109297A3/en unknown
- 1996-03-04 WO PCT/US1996/002887 patent/WO1996028417A1/en active IP Right Grant
- 1996-03-04 PL PL96322212A patent/PL322212A1/en unknown
- 1996-03-04 CZ CZ19972875A patent/CZ291279B6/en not_active IP Right Cessation
- 1996-03-04 BR BR9607470A patent/BR9607470A/en not_active Application Discontinuation
- 1996-03-07 IL IL11739496A patent/IL117394A/en active IP Right Grant
- 1996-03-13 EG EG22196A patent/EG20957A/en active
- 1996-03-14 MA MA24182A patent/MA23825A1/en unknown
- 1996-03-14 ZA ZA962057A patent/ZA962057B/en unknown
- 1996-05-02 TW TW085105280A patent/TW330196B/en active
-
1997
- 1997-09-05 NO NO974095A patent/NO308357B1/en unknown
-
2001
- 2001-01-11 GR GR20010400028T patent/GR3035214T3/en not_active IP Right Cessation
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4634551A (en) * | 1985-06-03 | 1987-01-06 | Procter & Gamble Company | Bleaching compounds and compositions comprising fatty peroxyacids salts thereof and precursors therefor having amide moieties in the fatty chain |
EP0294073A1 (en) * | 1987-06-02 | 1988-12-07 | Interox Chemicals Limited | Preparation of esters |
WO1994028106A1 (en) * | 1993-05-20 | 1994-12-08 | The Procter & Gamble Company | Bleaching compounds comprising peroxyacid activators used with enzymes |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2001038298A1 (en) * | 1999-11-25 | 2001-05-31 | Siemens Axiva Gmbh & Co. Kg | Method for isolating amido acid phenyl ester sulfonates out of water-solvent mixtures |
US6720441B2 (en) | 1999-11-25 | 2004-04-13 | Siemens Axiva Gmbh & Co. Kg | Recovery and purification of substituted benzenesulfonates |
Also Published As
Publication number | Publication date |
---|---|
HUP9801398A2 (en) | 1998-12-28 |
CA2214117C (en) | 2002-08-13 |
GR3035214T3 (en) | 2001-04-30 |
ZA962057B (en) | 1996-11-27 |
NO974095L (en) | 1997-09-05 |
CA2214117A1 (en) | 1996-09-19 |
DE69611356D1 (en) | 2001-02-01 |
PL322212A1 (en) | 1998-01-19 |
EP0815075B1 (en) | 2000-12-27 |
BR9607470A (en) | 1997-12-23 |
MA23825A1 (en) | 1996-10-01 |
US5523434A (en) | 1996-06-04 |
CZ287597A3 (en) | 1998-02-18 |
CZ291279B6 (en) | 2003-01-15 |
MX9707037A (en) | 1997-11-29 |
IL117394A0 (en) | 1996-07-23 |
ES2153099T3 (en) | 2001-02-16 |
DE69611356T2 (en) | 2001-07-19 |
ATE198322T1 (en) | 2001-01-15 |
RU2158256C2 (en) | 2000-10-27 |
SK109297A3 (en) | 1998-08-05 |
TR199700951T1 (en) | 1998-01-21 |
TW330196B (en) | 1998-04-21 |
HUP9801398A3 (en) | 2000-03-28 |
NO308357B1 (en) | 2000-09-04 |
EG20957A (en) | 2000-07-30 |
IL117394A (en) | 2000-08-31 |
AU5357296A (en) | 1996-10-02 |
NO974095D0 (en) | 1997-09-05 |
DK0815075T3 (en) | 2001-01-29 |
EP0815075A1 (en) | 1998-01-07 |
PT815075E (en) | 2001-04-30 |
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