US2893990A - Process for producing sugar esters - Google Patents

Process for producing sugar esters Download PDF

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Publication number
US2893990A
US2893990A US552281A US55228155A US2893990A US 2893990 A US2893990 A US 2893990A US 552281 A US552281 A US 552281A US 55228155 A US55228155 A US 55228155A US 2893990 A US2893990 A US 2893990A
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United States
Prior art keywords
sucrose
esters
grams
ester
employed
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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 - Lifetime
Application number
US552281A
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English (en)
Inventor
Henry B Hass
Foster D Snell
William C York
Lloyd I Osipow
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Sugar Res Foundation Inc
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Sugar Res Foundation Inc
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Filing date
Publication date
Priority to NL111638D priority Critical patent/NL111638C/xx
Application filed by Sugar Res Foundation Inc filed Critical Sugar Res Foundation Inc
Priority to US552281A priority patent/US2893990A/en
Priority to FR1146644D priority patent/FR1146644A/fr
Application granted granted Critical
Publication of US2893990A publication Critical patent/US2893990A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
    • C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
    • C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
    • C07H13/06—Fatty acids
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B23—MACHINE TOOLS; METAL-WORKING NOT OTHERWISE PROVIDED FOR
    • B23K—SOLDERING OR UNSOLDERING; WELDING; CLADDING OR PLATING BY SOLDERING OR WELDING; CUTTING BY APPLYING HEAT LOCALLY, e.g. FLAME CUTTING; WORKING BY LASER BEAM
    • B23K5/00—Gas flame welding
    • B23K5/02—Seam welding
    • B23K5/06—Welding longitudinal seams
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
    • 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
    • C11D1/66—Non-ionic compounds
    • C11D1/662—Carbohydrates or derivatives
    • 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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/02—Inorganic compounds ; Elemental compounds
    • C11D3/04—Water-soluble compounds
    • C11D3/06—Phosphates, including polyphosphates

Definitions

  • the present invention relates to a novel process for producing esters of sucrose or raflinose and fatty acids having from about 6 to 30 carbon atoms and to the esters obtained thereby.
  • the monoand di-esters of the invention may be employed in producing poultry, cattle and swine rations to improve the digestibility of such rations.
  • esters of the present invention maybe employed for secondary oil for petroleum recovery whereby aqueous whereby solutions of these esters are used to displace residual oil from the underground rock and thereby permit more efficient recovery of petroleum from the ground,
  • the product obtained issubstantially a mono-ester. If one mole of sucrose is employed with two moles ,of a fattyacid ester of a volatile alcohol, the product is essentially a di-ester of sucrose.
  • By using largeenough ratios of non-sucrose ester it is possible to provide esters ofsucrose in which several hydroxyls are esterified.
  • the resulting dimethylformamide solution was further distilled in vacuo to a thick syrup, which was precipitated with acetone.
  • the acetone solution was evaporated, producing a residue which was composed of 22 grams (0.036 mole) of relatively pure sucrose mono-stearate, having a melting point of about 5253 C.; M1 +33.2, for an absolute yield of 24.6% based upon the amount of distearin employed in the reaction.
  • the unreacted sucrose obtained above was filtered and dried to be used in subsequent processes. Pure sucrose monostearate was found to have a melting point of 5253 C.
  • Example VI A solution was prepared by dissolving about 70 grams (0.208 mole) of sucrose in 400 ml. of N,N-dimethylformamide. With the resulting solution was mixed 92 grams (0.14 mole) of tristearin dissolved in 400 ml. of dimethylformamide. The mixture was placed in a pressure bomb along with 3 grams of trisodium phosphate. The bomb was heated for about 8 hours at a temperature of C. One-half of the dimethylformamide was removed by distillation and the resulting sucrose monostearate was recovered as in Example II. The quantity of recovered substantially-pure sucrose mono-stearate indicated a conversion yield of about 29%.

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  • 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)
  • Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Inorganic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Mechanical Engineering (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Saccharide Compounds (AREA)
US552281A 1955-12-12 1955-12-12 Process for producing sugar esters Expired - Lifetime US2893990A (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
NL111638D NL111638C (nl) 1955-12-12
US552281A US2893990A (en) 1955-12-12 1955-12-12 Process for producing sugar esters
FR1146644D FR1146644A (fr) 1955-12-12 1956-01-06 Nouveaux esters de saccharides et d'acides gras, leur procédé de préparation et leurs applications

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US552281A US2893990A (en) 1955-12-12 1955-12-12 Process for producing sugar esters

Publications (1)

Publication Number Publication Date
US2893990A true US2893990A (en) 1959-07-07

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Family Applications (1)

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US552281A Expired - Lifetime US2893990A (en) 1955-12-12 1955-12-12 Process for producing sugar esters

Country Status (3)

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US (1) US2893990A (nl)
FR (1) FR1146644A (nl)
NL (1) NL111638C (nl)

Cited By (73)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2951015A (en) * 1957-07-02 1960-08-30 Pfizer & Co C Aqueous readily injectable therapeutic compositions containing water-insoluble penicillin and sucrose dilaurate
US2992082A (en) * 1958-06-24 1961-07-11 Eastman Kodak Co Anti-sludging hydrocarbon fuel oils
US2997491A (en) * 1959-09-29 1961-08-22 Procter & Gamble Method for preparing partial fatty esters of inositol
US2997493A (en) * 1959-09-29 1961-08-22 Procter & Gamble Method for preparing straight chain hexitol fatty esters
US2997490A (en) * 1959-05-08 1961-08-22 Procter & Gamble Method for preparing fatty esters
US2999023A (en) * 1959-05-08 1961-09-05 Drew & Co Inc E F Confectionary coating compositions
US2999858A (en) * 1956-09-18 1961-09-12 Robert S Aries Preparation of sucrose monoesters
US3023183A (en) * 1959-06-29 1962-02-27 Cuban American Sugar Company Esterification
US3024229A (en) * 1957-07-26 1962-03-06 Bayer Ag Preparation of ester salts of di and trisaccharides
US3053677A (en) * 1959-11-12 1962-09-11 Eastman Kodak Co Petroleum wax for paper coatings
US3054789A (en) * 1959-02-06 1962-09-18 Ledoga Spa Process for the preparation of pure sucrose esters
US3061629A (en) * 1958-11-19 1962-10-30 Celanese Corp Dialkyl sulfoxide in preparation of isocyanate-polyol adduct
US3096324A (en) * 1960-08-24 1963-07-02 Eastman Kodak Co Process for manufacturing sugar esters
US3141012A (en) * 1960-06-01 1964-07-14 North American Sugar Ind Inc Recovering solid polyhydric alcohols from transesterification reaction masses
DE1200276B (de) * 1959-10-08 1965-09-09 Bayer Ag Verfahren zum Herstellen von Carbonsaeureestern nichtreduzierender Zucker
US3219484A (en) * 1961-08-07 1965-11-23 Colonial Sugar Refining Co Process for the purification of sugars and their derivatives
DE1205511B (de) * 1961-10-31 1965-11-25 Ledoga Spa Verfahren zur Trennung von Rohrzuckermono- und -diestern gesaettigter oder ungesaettigter Fettsaeuren mit 6 bis 30 Kohlenstoffatomen
DE1205510B (de) * 1961-09-12 1965-11-25 Ledoga Spa Verfahren zur quantitativen Abtrennung von reinen Rohrzuckermono- bzw. -diestern gesaettigter oder ungesaettigter Fettsaeuren mit 6 bis 30 Kohlenstoffatomen
US3231562A (en) * 1959-05-21 1966-01-25 Dainippon Seito Kabushiki Kais Process for recovering unreacted sucrose from reaction solution of fatty acid sucrose ester
US3248381A (en) * 1961-11-21 1966-04-26 Ledoga Spa Process for the preparation of watersoluble and water-insoluble sucrose esters and products obtained thereby
US3251829A (en) * 1963-03-21 1966-05-17 Bayer Ag Process for the separation of unreacted sugars from reaction mixtures obtained in the production of sugar fatty acid esters from sugars and fatty acid alkyl esters
US3476598A (en) * 1966-05-10 1969-11-04 Varney Chem Corp Sucrose based surfactants as aids in sugar refining and sugar crystallization processes
US3480616A (en) * 1966-04-06 1969-11-25 Nebraska State Esterification of polyhydric compounds in the presence of transparent emulsifying agent
US3481881A (en) * 1965-02-06 1969-12-02 Boehme Chem Fab Kg Soap or detergent rinsing agent
US3867301A (en) * 1971-09-11 1975-02-18 Dai Ichi Kogyo Seiyaku Co Ltd Detergent compositions
US3872020A (en) * 1971-09-14 1975-03-18 Dai Ichi Kogyo Seiyaku Co Ltd Detergent compositions
US3954976A (en) * 1973-12-14 1976-05-04 The Procter & Gamble Company Pharmaceutical compositions for inhibiting absorption of cholesterol
JPS5244803A (en) * 1976-08-24 1977-04-08 Dai Ichi Kogyo Seiyaku Co Ltd Detergent compositions
US4087371A (en) * 1971-12-23 1978-05-02 Grillo-Werke Aktiengesellschaft Method of preventing incrustation on heated surfaces, and composition for the practice of the method
WO1980000452A1 (en) * 1978-08-30 1980-03-20 Quimica Milen Sa Non-polluting detergent composition containing soap and sucrose esters
US4241054A (en) * 1978-12-08 1980-12-23 The Procter & Gamble Company Detoxifying lipophilic toxins
US4259202A (en) * 1979-02-27 1981-03-31 Toyo Contact Lens Co., Ltd. Cleaning and preservative solution for contact lenses
US4306062A (en) * 1979-05-24 1981-12-15 Talres Development (N.A.) N.V. Process for the preparation of sucrose monoesters
US4379755A (en) * 1978-08-10 1983-04-12 Nihon Surfactant Industry Co., Ltd. Gelatinizing agent composition, and gel and aqueous emulsion prepared therefrom
US4395365A (en) * 1980-09-08 1983-07-26 Nissan Motor Co., Ltd. Metal cleaning composition containing a fatty acid succrose ester and other detergent components
US4496547A (en) * 1981-12-25 1985-01-29 Mitsui Toatsu Chemicals, Inc. Saccharide fatty acid ester for bloat-prevention or bloat-treatment
US4517360A (en) * 1983-06-23 1985-05-14 The Procter & Gamble Company Synthesis of higher polyol fatty acid polyesters using carbonate catalysts
US4518772A (en) * 1983-06-23 1985-05-21 The Proctor & Gamble Company Synthesis of higher polyol fatty acid polyesters using high soap:polyol ratios
US4686205A (en) * 1983-07-07 1987-08-11 Ralston Purina Company Intake limiting feed for animals containing sucrose octaacetate
US4806632A (en) * 1986-12-29 1989-02-21 The Procter & Gamble Company Process for the post-hydrogenation of sucrose polyesters
US4822875A (en) * 1986-12-17 1989-04-18 The Procter & Gamble Company Sucrose polyesters which behave like cocoa butters
US4865848A (en) * 1987-02-26 1989-09-12 Alza Corporation Skin permeation enhancer compositions using sucrose esters
US4877871A (en) * 1988-06-14 1989-10-31 Nabisco Brands, Inc. Synthesis of sucrose polyester
EP0346845A2 (en) * 1988-06-14 1989-12-20 Mitsubishi Chemical Corporation Process for producing sucrose fatty acid polyester
US4927920A (en) * 1988-11-15 1990-05-22 Nebraska Department Of Economic Development, State Of Nebraska, U.S.A. Sugar ester synthesis
US4940586A (en) * 1987-02-26 1990-07-10 Alza Corporation Skin permeation enhancer compositions using sucrose esters
US4942054A (en) * 1987-05-13 1990-07-17 Curtice-Burns, Inc. Process for producing low calorie foods from alkyl glycoside fatty acid polyesters
WO1990011285A1 (en) * 1989-03-17 1990-10-04 Nebraska Department Of Economic Development, State Of Nebraska Separation and purification of sugar esters
US4962092A (en) * 1987-05-06 1990-10-09 The Procter & Gamble Company Compositions for treating duodenal ulcers
US5006648A (en) * 1986-07-23 1991-04-09 Van Den Bergh Foods Co., Division Of Conopco Inc. Process for preparing partial polyol fatty acid esters
USRE33885E (en) * 1975-11-03 1992-04-14 The Procter & Gamble Company Compositions for inhibiting absorption of cholesterol
USRE33996E (en) * 1976-02-12 1992-07-14 The Procter & Gamble Company Compositions for treating hypercholesterolemia
USRE34617E (en) * 1976-02-12 1994-05-24 The Procter & Gamble Company Vitaminized compositions for treating hypercholesterolemia
WO1994022919A1 (en) * 1993-04-07 1994-10-13 Alko Group Ltd. Applications and methods for the preparation of fatty acid esters of polysaccharides
US5424420A (en) * 1993-10-05 1995-06-13 Kraft Foods, Inc. Method for preparing saccharide polyesters by transesterification
US5439697A (en) * 1993-09-09 1995-08-08 The Pillsbury Company Low-fat spreadable compositions
US5440027A (en) * 1993-10-05 1995-08-08 Kraft General Foods, Inc. Method for preparing saccharide fatty acid polyesters by transesterification
US5453498A (en) * 1992-02-12 1995-09-26 Dai-Ichi Kogyo Seiyaku Co., Ltd. Process for production of high-monoester sucrose higher fatty acid esters
US5550220A (en) * 1987-05-13 1996-08-27 Curtice-Burns, Inc. Alkyl glycoside fatty acid polyester fat substitute food compositions and process to produce the same
US5559226A (en) * 1991-04-12 1996-09-24 The Procter & Gamble Company Process for making polyol fatty acid polyesters having oxidative stability
US5596085A (en) * 1995-04-11 1997-01-21 Kraft Foods, Inc. Method for preparing polyol fatty acid polyesters by transesterification
US5756716A (en) * 1995-06-07 1998-05-26 Kimball Chase Tech. Ltd. Sugar-ester manufacturing process
WO1998054276A1 (en) * 1997-05-30 1998-12-03 Oded Broshi An edible, pleasant tasting, bubble making composition
US5968566A (en) * 1996-05-14 1999-10-19 Mlp Operating Company Refrigerated yeast-raised pizza dough
US6121440A (en) * 1998-01-29 2000-09-19 The Procter & Gamble Company Process for synthesis of polyol fatty acid polyesters
US6497898B1 (en) 1993-10-07 2002-12-24 Kanebo Ltd Surfactant, and an emulsion-type cosmetic composition and a lipsome containing said surfactant
US20040063928A1 (en) * 2001-01-18 2004-04-01 Jo In-Ho Preparation of aliphatic acid ester of carbohydrate
US20070259084A1 (en) * 2006-05-04 2007-11-08 Gaonkar Anilkumar G Coffee-Derived Surfactants
US7304153B1 (en) 1990-09-11 2007-12-04 The Procter And Gamble Co. Polyol polyester synthesis
US20130312975A1 (en) * 2012-05-23 2013-11-28 Basf Se Process for Water Wetting Oil-Wet Surfaces
WO2018045248A1 (en) * 2016-09-01 2018-03-08 Hs Manufacturing Group Llc Methods for biobased derivatization of cellulosic surfaces
KR20190069016A (ko) * 2017-12-11 2019-06-19 주식회사 비제이바이오켐 당류계 지방산 에스테르 제조방법
US10717917B2 (en) 2016-06-24 2020-07-21 Croda, Inc. Method and composition for asphaltene dispersion

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1158486B (de) * 1959-02-06 1963-12-05 Ledoga Spa Verfahren zur Herstellung von reinen Saccharosemono- bzw. -diestern langkettiger, gesaettigter oder ungesaettigter Fettsaeuren mit 6 bis 30 Kohlenstoffatomen bzw. deren Mischungen
FR2540511B1 (fr) * 1983-02-04 1985-08-09 Henkel France Composition liquide de nettoyage, ainsi que procede de nettoyage a partir de cette composition
JPH0662659B2 (ja) * 1988-04-18 1994-08-17 第一工業製薬株式会社 ショ糖脂肪酸エステルを含む反応混合物の処理方法
FR2670493A1 (fr) * 1990-12-13 1992-06-19 Isochem Sa Nouveaux composes monoesters du saccharose tels que les 2-0-acylsaccharoses et les 6-0-acylsaccharoses, ainsi que leurs procedes de synthese.

Citations (7)

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US1959590A (en) * 1932-03-22 1934-05-22 Hercules Powder Co Ltd Fatty acid esters of carbohydrates and method for producing
US2147241A (en) * 1937-08-14 1939-02-14 Corn Prod Refining Co Production of fatty acid esters from starch factory byproducts
US2399959A (en) * 1942-07-02 1946-05-07 Procter & Gamble Process of producing esters
US2586897A (en) * 1948-07-03 1952-02-26 Victor Chemical Works Detergent composition
US2594453A (en) * 1950-04-01 1952-04-29 Monsanto Chemicals Detergent compositions
US2602789A (en) * 1949-08-23 1952-07-08 Joseph H Schwartz Ether-esters of polyhydroxy compounds
US2700022A (en) * 1952-07-15 1955-01-18 California Research Corp Sugar ester-containing lubricant compositions

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1959590A (en) * 1932-03-22 1934-05-22 Hercules Powder Co Ltd Fatty acid esters of carbohydrates and method for producing
US2147241A (en) * 1937-08-14 1939-02-14 Corn Prod Refining Co Production of fatty acid esters from starch factory byproducts
US2399959A (en) * 1942-07-02 1946-05-07 Procter & Gamble Process of producing esters
US2586897A (en) * 1948-07-03 1952-02-26 Victor Chemical Works Detergent composition
US2602789A (en) * 1949-08-23 1952-07-08 Joseph H Schwartz Ether-esters of polyhydroxy compounds
US2594453A (en) * 1950-04-01 1952-04-29 Monsanto Chemicals Detergent compositions
US2700022A (en) * 1952-07-15 1955-01-18 California Research Corp Sugar ester-containing lubricant compositions

Cited By (91)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2999858A (en) * 1956-09-18 1961-09-12 Robert S Aries Preparation of sucrose monoesters
US2951015A (en) * 1957-07-02 1960-08-30 Pfizer & Co C Aqueous readily injectable therapeutic compositions containing water-insoluble penicillin and sucrose dilaurate
US3024229A (en) * 1957-07-26 1962-03-06 Bayer Ag Preparation of ester salts of di and trisaccharides
US2992082A (en) * 1958-06-24 1961-07-11 Eastman Kodak Co Anti-sludging hydrocarbon fuel oils
US3061629A (en) * 1958-11-19 1962-10-30 Celanese Corp Dialkyl sulfoxide in preparation of isocyanate-polyol adduct
US3054789A (en) * 1959-02-06 1962-09-18 Ledoga Spa Process for the preparation of pure sucrose esters
US2997490A (en) * 1959-05-08 1961-08-22 Procter & Gamble Method for preparing fatty esters
US2999023A (en) * 1959-05-08 1961-09-05 Drew & Co Inc E F Confectionary coating compositions
US3231562A (en) * 1959-05-21 1966-01-25 Dainippon Seito Kabushiki Kais Process for recovering unreacted sucrose from reaction solution of fatty acid sucrose ester
US3023183A (en) * 1959-06-29 1962-02-27 Cuban American Sugar Company Esterification
US2997491A (en) * 1959-09-29 1961-08-22 Procter & Gamble Method for preparing partial fatty esters of inositol
US2997493A (en) * 1959-09-29 1961-08-22 Procter & Gamble Method for preparing straight chain hexitol fatty esters
US3251827A (en) * 1959-10-08 1966-05-17 Bayer Ag Process for the production of sugar esters
DE1200276B (de) * 1959-10-08 1965-09-09 Bayer Ag Verfahren zum Herstellen von Carbonsaeureestern nichtreduzierender Zucker
US3053677A (en) * 1959-11-12 1962-09-11 Eastman Kodak Co Petroleum wax for paper coatings
US3141012A (en) * 1960-06-01 1964-07-14 North American Sugar Ind Inc Recovering solid polyhydric alcohols from transesterification reaction masses
US3096324A (en) * 1960-08-24 1963-07-02 Eastman Kodak Co Process for manufacturing sugar esters
US3219484A (en) * 1961-08-07 1965-11-23 Colonial Sugar Refining Co Process for the purification of sugars and their derivatives
DE1205510B (de) * 1961-09-12 1965-11-25 Ledoga Spa Verfahren zur quantitativen Abtrennung von reinen Rohrzuckermono- bzw. -diestern gesaettigter oder ungesaettigter Fettsaeuren mit 6 bis 30 Kohlenstoffatomen
DE1205511B (de) * 1961-10-31 1965-11-25 Ledoga Spa Verfahren zur Trennung von Rohrzuckermono- und -diestern gesaettigter oder ungesaettigter Fettsaeuren mit 6 bis 30 Kohlenstoffatomen
US3248381A (en) * 1961-11-21 1966-04-26 Ledoga Spa Process for the preparation of watersoluble and water-insoluble sucrose esters and products obtained thereby
US3251829A (en) * 1963-03-21 1966-05-17 Bayer Ag Process for the separation of unreacted sugars from reaction mixtures obtained in the production of sugar fatty acid esters from sugars and fatty acid alkyl esters
DE1270021B (de) * 1963-03-21 1968-06-12 Bayer Ag Verfahren zur Abtrennung nicht-umgesetzter Zucker aus dem bei der Herstellung von Zuckerfettsaeureestern aus Fettsaeurealkylestern und ueberschuessigen Mengen an Zuckernin Dimethylformamid, Dimethylacetamid, Dialkylsulfoxyd oder Butyrolacton erhaltenenReaktionsgemisch
US3481881A (en) * 1965-02-06 1969-12-02 Boehme Chem Fab Kg Soap or detergent rinsing agent
US3480616A (en) * 1966-04-06 1969-11-25 Nebraska State Esterification of polyhydric compounds in the presence of transparent emulsifying agent
US3476598A (en) * 1966-05-10 1969-11-04 Varney Chem Corp Sucrose based surfactants as aids in sugar refining and sugar crystallization processes
US3867301A (en) * 1971-09-11 1975-02-18 Dai Ichi Kogyo Seiyaku Co Ltd Detergent compositions
US3872020A (en) * 1971-09-14 1975-03-18 Dai Ichi Kogyo Seiyaku Co Ltd Detergent compositions
US4087371A (en) * 1971-12-23 1978-05-02 Grillo-Werke Aktiengesellschaft Method of preventing incrustation on heated surfaces, and composition for the practice of the method
US3954976A (en) * 1973-12-14 1976-05-04 The Procter & Gamble Company Pharmaceutical compositions for inhibiting absorption of cholesterol
USRE33885E (en) * 1975-11-03 1992-04-14 The Procter & Gamble Company Compositions for inhibiting absorption of cholesterol
USRE34617E (en) * 1976-02-12 1994-05-24 The Procter & Gamble Company Vitaminized compositions for treating hypercholesterolemia
USRE33996E (en) * 1976-02-12 1992-07-14 The Procter & Gamble Company Compositions for treating hypercholesterolemia
JPS5314565B2 (nl) * 1976-08-24 1978-05-18
JPS5244803A (en) * 1976-08-24 1977-04-08 Dai Ichi Kogyo Seiyaku Co Ltd Detergent compositions
US4379755A (en) * 1978-08-10 1983-04-12 Nihon Surfactant Industry Co., Ltd. Gelatinizing agent composition, and gel and aqueous emulsion prepared therefrom
WO1980000452A1 (en) * 1978-08-30 1980-03-20 Quimica Milen Sa Non-polluting detergent composition containing soap and sucrose esters
US4241054A (en) * 1978-12-08 1980-12-23 The Procter & Gamble Company Detoxifying lipophilic toxins
US4259202A (en) * 1979-02-27 1981-03-31 Toyo Contact Lens Co., Ltd. Cleaning and preservative solution for contact lenses
US4306062A (en) * 1979-05-24 1981-12-15 Talres Development (N.A.) N.V. Process for the preparation of sucrose monoesters
US4395365A (en) * 1980-09-08 1983-07-26 Nissan Motor Co., Ltd. Metal cleaning composition containing a fatty acid succrose ester and other detergent components
US4496547A (en) * 1981-12-25 1985-01-29 Mitsui Toatsu Chemicals, Inc. Saccharide fatty acid ester for bloat-prevention or bloat-treatment
US4518772A (en) * 1983-06-23 1985-05-21 The Proctor & Gamble Company Synthesis of higher polyol fatty acid polyesters using high soap:polyol ratios
US4517360A (en) * 1983-06-23 1985-05-14 The Procter & Gamble Company Synthesis of higher polyol fatty acid polyesters using carbonate catalysts
US4686205A (en) * 1983-07-07 1987-08-11 Ralston Purina Company Intake limiting feed for animals containing sucrose octaacetate
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FR1146644A (fr) 1957-11-13

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