GB959412A - Mono- or di-esters of citric acid - Google Patents
Mono- or di-esters of citric acidInfo
- Publication number
- GB959412A GB959412A GB37332/61A GB3733261A GB959412A GB 959412 A GB959412 A GB 959412A GB 37332/61 A GB37332/61 A GB 37332/61A GB 3733261 A GB3733261 A GB 3733261A GB 959412 A GB959412 A GB 959412A
- Authority
- GB
- United Kingdom
- Prior art keywords
- citric acid
- citrate
- paper
- mono
- esters
- 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
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 title abstract 14
- 150000005690 diesters Chemical class 0.000 title abstract 3
- 239000000839 emulsion Substances 0.000 abstract 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 239000000123 paper Substances 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical group N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 abstract 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 abstract 2
- -1 aliphatic alcohols Chemical class 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 239000003995 emulsifying agent Substances 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 239000004753 textile Substances 0.000 abstract 2
- NBYLBWHHTUWMER-UHFFFAOYSA-N 2-Methylquinolin-8-ol Chemical class C1=CC=C(O)C2=NC(C)=CC=C21 NBYLBWHHTUWMER-UHFFFAOYSA-N 0.000 abstract 1
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 abstract 1
- HPRXLHZLLKAYPO-UHFFFAOYSA-N 2-hydroxy-2-[2-(11-methyldodecoxy)-2-oxoethyl]butanedioic acid Chemical compound CC(C)CCCCCCCCCCOC(=O)CC(CC(=O)O)(C(=O)O)O HPRXLHZLLKAYPO-UHFFFAOYSA-N 0.000 abstract 1
- QZCLKYGREBVARF-UHFFFAOYSA-N Acetyl tributyl citrate Chemical compound CCCCOC(=O)CC(C(=O)OCCCC)(OC(C)=O)CC(=O)OCCCC QZCLKYGREBVARF-UHFFFAOYSA-N 0.000 abstract 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical group ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 1
- 229920000877 Melamine resin Polymers 0.000 abstract 1
- 239000004640 Melamine resin Substances 0.000 abstract 1
- 229920000297 Rayon Polymers 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 239000003513 alkali Chemical group 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 239000011111 cardboard Substances 0.000 abstract 1
- 150000001860 citric acid derivatives Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 235000013305 food Nutrition 0.000 abstract 1
- 150000002429 hydrazines Chemical class 0.000 abstract 1
- 229910001629 magnesium chloride Inorganic materials 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 238000012856 packing Methods 0.000 abstract 1
- 239000011087 paperboard Substances 0.000 abstract 1
- 239000004014 plasticizer Substances 0.000 abstract 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical class C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 abstract 1
- BDFPEAPQMCIGMG-UHFFFAOYSA-M sodium 2-hydroxy-4-(11-methyldodecoxy)-2-[2-(11-methyldodecoxy)-2-oxoethyl]-4-oxobutanoate Chemical compound C(CC(O)(C(=O)[O-])CC(=O)OCCCCCCCCCCC(C)C)(=O)OCCCCCCCCCCC(C)C.[Na+] BDFPEAPQMCIGMG-UHFFFAOYSA-M 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 abstract 1
- 229920003002 synthetic resin Polymers 0.000 abstract 1
- 239000000057 synthetic resin Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/675—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids of saturated hydroxy-carboxylic acids
- C07C69/704—Citric acid esters
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
Abstract
Mono- and di-esters of citric acid are prepared by esterification of the acid with branched chain aliphatic alcohols containing at least 9 carbon atoms. Examples describe the preparation of diisotridecylcitrate, diisononylcitrate, diisodecyl citrate and monoisotridecylcitrate. The compounds or their salts, for example, with hydrazine, hydroxylamine, ammonia and alkalies substituted hydrazines, hydroxyquinoline and hydroxyquinaldine may be used as emulsifying agents for the preparation of stable and storable emulsions of fully esterified citric acid. The stable emulsions are used to treat paper, textiles or as plasticisers for synthetic resins.ALSO:Mono- or di-esters of citric acid and branched chain aliphatic alchols containing at least 9 carbon atoms, or salts thereof are used as emulsifying agents for fully esterified citric acid ester emulsions which are used for processing textiles, paper and cardboard. In examples, a dyed satin viscose rayon material is treated in a bath with an aqueous emulsion of acetyltributyl citrate, diisotrindecyl citrate and sodium hydroxide containing melamine resin, magnesium chloride and the sodium salt of dodecyl-phenyl sulphonic acid, impregnated in a foulard, dried and condensed at 1550 DEG C; an aqueous emulsion of acetyltributyl and diisotridecyl citrates and sodium diisotridecyl citrate is added to a 4% bleached sulphite pulp which is homogeneously dispersed in a Hollander and the paper made therefrom is soft and flexible and suitable for packing foods or as wrapping paper.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB0060102 | 1960-11-16 | ||
| DEB60103A DE1174754B (en) | 1960-11-16 | 1960-11-16 | Process for the production of citric acid mono- or diesters or their ester salts which are used as emulsifiers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB959412A true GB959412A (en) | 1964-06-03 |
Family
ID=25965779
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB37332/61A Expired GB959412A (en) | 1960-11-16 | 1961-10-18 | Mono- or di-esters of citric acid |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB959412A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4888195A (en) * | 1988-07-26 | 1989-12-19 | Nabisco Brands, Inc. | Ether bridged polyesters and food compositions containing ether bridged polyesters |
| US5049699A (en) * | 1990-01-22 | 1991-09-17 | Haarmanns' Reimer Corp | Regioselective synthesis of mono-alkyl citric acid esters |
| US5338470A (en) * | 1992-12-10 | 1994-08-16 | Mobil Oil Corporation | Alkylated citric acid adducts as antiwear and friction modifying additives |
| CN112574038A (en) * | 2021-01-07 | 2021-03-30 | 北京微量化学研究所 | Selective synthesis method of citric acid monoester |
-
1961
- 1961-10-18 GB GB37332/61A patent/GB959412A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4888195A (en) * | 1988-07-26 | 1989-12-19 | Nabisco Brands, Inc. | Ether bridged polyesters and food compositions containing ether bridged polyesters |
| US5049699A (en) * | 1990-01-22 | 1991-09-17 | Haarmanns' Reimer Corp | Regioselective synthesis of mono-alkyl citric acid esters |
| US5338470A (en) * | 1992-12-10 | 1994-08-16 | Mobil Oil Corporation | Alkylated citric acid adducts as antiwear and friction modifying additives |
| CN112574038A (en) * | 2021-01-07 | 2021-03-30 | 北京微量化学研究所 | Selective synthesis method of citric acid monoester |
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