US3251829A - 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 - Google Patents
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 Download PDFInfo
- Publication number
- US3251829A US3251829A US348830A US34883064A US3251829A US 3251829 A US3251829 A US 3251829A US 348830 A US348830 A US 348830A US 34883064 A US34883064 A US 34883064A US 3251829 A US3251829 A US 3251829A
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- US
- United States
- Prior art keywords
- fatty acid
- sugars
- sugar
- esters
- production
- 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 - Lifetime
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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
Definitions
- -Hydrocarbons suitable for carrying out the present invention are, for example, methylene chloride, chloroform, 1,2-dichloroethane, 1,2-dichloropropane, acetone, methyl ethyl ketone as well as benzene, toluene, xylene andchlorobenzene.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
Description
United States Patent 2 Claims. (Cl. 260234) In-the production of sugar fatty acid esters, especially sugar monofatty acid esters, from sugars, such as e.g. saccharose, raffinose or trehalose, and fatty acid alkyl esters, such as e.g. stearic acid, oleic acid or palmitic acid methyl ester, in dimethyl formamide, dimethyl acetamide, dialkyl sulphoxide or butyrolactone, it is necessary to use an excess of sugars, referred to the amount of fatty acid alkyl esters employed, and, after termination of the reaction, to separate the unreacted sugars from the sugar fatty acid esters formed.
The present invention relates to a process for the separation of unreacted sugars from the reaction mixture obtained in such a production of sugar fatty acid esters; the process is characterised in that the reaction mixture which still contains the dimethyl formamide, dimethyl acetamide, dialkyl 'sulphoxide or butyrolactone, is mixed with those aliphatic hydrocarbons containing halogen or keto groups, or with those aromatic halogen-containing or halogen-free hydrocarbons which are miscible with dimethyl formamide, dimethyl acetamide, dialkyl sulphoxide or butyrolactone, and that the sugars which precipitate, are separated.
-Hydrocarbons suitable for carrying out the present invention are, for example, methylene chloride, chloroform, 1,2-dichloroethane, 1,2-dichloropropane, acetone, methyl ethyl ketone as well as benzene, toluene, xylene andchlorobenzene.
The necessary amounts of these hydrocarbons can easily be established by preliminary experiments. In general, it is recommended to use an amount of hydrocarbons at least equal to that of the solvents dimethyl formamide, dimethyl acetamide, dialkyl sulphoxide or butyrolactone, used for the production of the sugar esters.
The temperature of the reaction mixture to be mixed with the hydrocarbons according to the invention can lie between 20 and 90 C., but preferably between 40 and 60 C. If desired, the reaction mixture which still contains the dimethyl formamide, dimethyl acetamide, dialkyl sulphoxide or butyrolactone can also be added to the hydrocarbons. In order to complete the separation of the unreacted sugars, the mixture consisting of the reaction mixture and the hydrocarbons according to the invention is expediently thoroughly stirred for some time.
3,251,829 Patented May 17, 1966 By means of the process of the present invention it is possible to liberate the sugar fatty acid esters from the unreacted sugars in a simple way and without loss, so that they can subsequently be worked up in usual manner.
The unreacted sugars thereby precipitate in a form in which they can easily be filtered off; they can then directly be used again for the production of sugar esters. Due to this fact, the process of the invention is superior to the knOWn processes in which the solvent employed is first removed from the reaction mixture by evaporation and the unreacted sugars are then separated from the residue by selective dissolving by means of a dilute aqueous common salt solution or by means of a mixture of butanol and a dilute common salt solution. These methods involve considerable losses of sugar fatty acids, and the recovery of the unreacted sugars from the aqueous common salt solutions is very cumbersome.
Example 308 g. (0.9 mol) of saccharose, 89.4 g. (0.3 mol) of stearic acid methyl ester and 3 g. of potassium carbonate are reacted in known manner in 1.2 litres of dimethyl formamide to give the saccharose monofatty acid ester. When the reaction is completed, 2.2 litres of 1,2-dichloropropane are added with stirring within 45 minutes to the solution at C., the temperature is maintained at 60 C., and the reaction mixture subsequently further stirred at 60 C. for 10-15 minutes. The precipitated sugar is then filtered oif and dried in a vacuum. The 1,2-dichloropropane is distilled off from the filtrate at 40-50" C. and 15 mm. Hg, and the remaining solution of the sugar ester in dimethyl formamide is worked up in known manner.
We claim: 7
1. The process for the separation of unreacted sugars from the reaction mixture obtained during the production of sugar fatty acid esters by reacting fatty acid alkyl esters and excess amounts of a sugar in a reaction medium selected from the group consisting of dimethyl formamide, dimethyl acetamide, dialkyl sulphoxide and butyrolactone, said process consisting of the steps of mixing the reaction mixture containing said reaction medium with an agent selected from the groups consisting of halogenated aliphatic hydrocarbons, halogenated aromatic hydrocarbons, and halogen-free hydrocarbons which are miscible with said reaction medium to thereby precipitate said excess sugar and separating said precipitated sugar.
2. The process of claim 1 wherein said sugar is saccharose, said reaction medium is dimethyl formamide, and 1,2-dichloropropane is the mixed agent.
References Cited by the Examiner UNITED STATES PATENTS 2,893,990 7/1959 Hass et al 260234 2,931,802 4/1960 Tovey et a1. 260234 2,938,716 8/1960 Davis 260234 LEWIS GOTTS, Primary Examiner.
Claims (1)
1. THE PROCESS FOR THE SEPARATION OF UNREACTED SUGARS FROM THE REACTION MIXTURE OBTAINED DURING THE PRODUCTION OF SUGAR FATTY ACID ESTERS BY REACTING FATTY ACID ALKYL ESTERS AND EXCESS AMOUNTS OF A SUGAR IN A REACTION MEDIUM SELECTED FROM THE GROUP CONSISTING OF DIMETHYL FORMAMIDE, DIMETHYL ACETAMIDE, DIALKYL SULPHOXIDE AND BUTAYROLACTONE, SAID PROCESS CONSISTING OF THE STEPS OF MIXING THE REACTION MIXTURE CONTAINING SAID REACTION MEDIUM WITH AN AGENT SELECTED FROM THE GROUPS CONSISTING OF HALOGENATED ALIPHATIC HYDROCARBONS, HALOGENATED AROMATIC HYDROCARBONS, AND HALOGEN-FREE HYDROCARBONS WHICH ARE MISCIBLE WITH SAID REACTION MEDIUM TO THEREBY PRECIPITATE SAID EXCESS SUGAR AND SEPARATING SAID PRECIPITATED SUGAR.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF0039297 | 1963-03-21 |
Publications (1)
Publication Number | Publication Date |
---|---|
US3251829A true US3251829A (en) | 1966-05-17 |
Family
ID=7097707
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US348830A Expired - Lifetime US3251829A (en) | 1963-03-21 | 1964-03-02 | 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 |
Country Status (8)
Country | Link |
---|---|
US (1) | US3251829A (en) |
AT (1) | AT256884B (en) |
BE (1) | BE645483A (en) |
CH (1) | CH427767A (en) |
DE (1) | DE1270021B (en) |
FR (1) | FR1385342A (en) |
GB (1) | GB1012424A (en) |
NL (1) | NL6402771A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3347848A (en) * | 1964-07-08 | 1967-10-17 | Ismail Roshdy | Process for the production of sucrose esters of fatty acids |
DE4015733A1 (en) * | 1990-05-16 | 1991-11-21 | Grillo Werke Ag | Mono and/or di:ester(s) of alpha D-methyl-glucoside prepn. - by solvent-free process in presence of carrier impregnated with basic catalyst and poly:carboxylic acid soap |
DE4103681A1 (en) * | 1991-02-07 | 1992-08-13 | Grillo Werke Ag | DERIVATIVES OF DISACCHARIDE ALCOHOLS, PROCESS FOR THEIR PREPARATION AND THEIR USE |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2893990A (en) * | 1955-12-12 | 1959-07-07 | Sugar Res Foundation Inc | Process for producing sugar esters |
US2931802A (en) * | 1958-04-30 | 1960-04-05 | Eastman Kodak Co | Mixed esters of glucose and sucrose |
US2938716A (en) * | 1956-05-28 | 1960-05-31 | Harold B Conant | Apparatus for producing copper oxide cells |
-
1963
- 1963-03-21 DE DEP1270A patent/DE1270021B/en active Pending
-
1964
- 1964-02-24 CH CH221864A patent/CH427767A/en unknown
- 1964-03-02 US US348830A patent/US3251829A/en not_active Expired - Lifetime
- 1964-03-11 AT AT210464A patent/AT256884B/en active
- 1964-03-12 GB GB10517/64A patent/GB1012424A/en not_active Expired
- 1964-03-16 NL NL6402771A patent/NL6402771A/xx unknown
- 1964-03-20 FR FR968025A patent/FR1385342A/en not_active Expired
- 1964-03-20 BE BE645483D patent/BE645483A/xx unknown
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2893990A (en) * | 1955-12-12 | 1959-07-07 | Sugar Res Foundation Inc | Process for producing sugar esters |
US2938716A (en) * | 1956-05-28 | 1960-05-31 | Harold B Conant | Apparatus for producing copper oxide cells |
US2931802A (en) * | 1958-04-30 | 1960-04-05 | Eastman Kodak Co | Mixed esters of glucose and sucrose |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3347848A (en) * | 1964-07-08 | 1967-10-17 | Ismail Roshdy | Process for the production of sucrose esters of fatty acids |
DE4015733A1 (en) * | 1990-05-16 | 1991-11-21 | Grillo Werke Ag | Mono and/or di:ester(s) of alpha D-methyl-glucoside prepn. - by solvent-free process in presence of carrier impregnated with basic catalyst and poly:carboxylic acid soap |
DE4103681A1 (en) * | 1991-02-07 | 1992-08-13 | Grillo Werke Ag | DERIVATIVES OF DISACCHARIDE ALCOHOLS, PROCESS FOR THEIR PREPARATION AND THEIR USE |
Also Published As
Publication number | Publication date |
---|---|
AT256884B (en) | 1967-09-11 |
FR1385342A (en) | 1965-01-08 |
GB1012424A (en) | 1965-12-08 |
DE1270021B (en) | 1968-06-12 |
BE645483A (en) | 1964-07-16 |
CH427767A (en) | 1967-01-15 |
NL6402771A (en) | 1964-09-22 |
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