GB689411A - Concentration of organic acids - Google Patents
Concentration of organic acidsInfo
- Publication number
- GB689411A GB689411A GB30666/50A GB3066650A GB689411A GB 689411 A GB689411 A GB 689411A GB 30666/50 A GB30666/50 A GB 30666/50A GB 3066650 A GB3066650 A GB 3066650A GB 689411 A GB689411 A GB 689411A
- Authority
- GB
- United Kingdom
- Prior art keywords
- mixture
- benzene
- diluent
- water
- extract
- 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
- 150000007524 organic acids Chemical class 0.000 title 1
- 235000005985 organic acids Nutrition 0.000 title 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 21
- 239000000203 mixture Substances 0.000 abstract 12
- 239000003085 diluting agent Substances 0.000 abstract 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 8
- 239000000284 extract Substances 0.000 abstract 7
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 abstract 6
- 239000002253 acid Substances 0.000 abstract 5
- 229910019142 PO4 Inorganic materials 0.000 abstract 4
- 150000007513 acids Chemical class 0.000 abstract 4
- 239000007864 aqueous solution Substances 0.000 abstract 4
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 4
- 239000000194 fatty acid Substances 0.000 abstract 4
- 229930195729 fatty acid Natural products 0.000 abstract 4
- 150000004665 fatty acids Chemical class 0.000 abstract 4
- 235000021317 phosphate Nutrition 0.000 abstract 4
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 abstract 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 238000004821 distillation Methods 0.000 abstract 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract 3
- 239000010452 phosphate Substances 0.000 abstract 3
- 235000019260 propionic acid Nutrition 0.000 abstract 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 abstract 3
- 239000000126 substance Substances 0.000 abstract 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 abstract 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical class CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 229940061607 dibasic sodium phosphate Drugs 0.000 abstract 2
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 abstract 2
- 238000000605 extraction Methods 0.000 abstract 2
- 238000000855 fermentation Methods 0.000 abstract 2
- 230000004151 fermentation Effects 0.000 abstract 2
- 235000013379 molasses Nutrition 0.000 abstract 2
- 239000001117 sulphuric acid Substances 0.000 abstract 2
- 235000011149 sulphuric acid Nutrition 0.000 abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- 241000186426 Acidipropionibacterium acidipropionici Species 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 abstract 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 abstract 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000002209 hydrophobic effect Effects 0.000 abstract 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 abstract 1
- 229910052753 mercury Inorganic materials 0.000 abstract 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 abstract 1
- 239000001632 sodium acetate Substances 0.000 abstract 1
- 235000017281 sodium acetate Nutrition 0.000 abstract 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 abstract 1
- 235000017557 sodium bicarbonate Nutrition 0.000 abstract 1
- 239000001509 sodium citrate Substances 0.000 abstract 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 abstract 1
- 235000011083 sodium citrates Nutrition 0.000 abstract 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 abstract 1
- HQUQLFOMPYWACS-UHFFFAOYSA-N tris(2-chloroethyl) phosphate Chemical class ClCCOP(=O)(OCCCl)OCCCl HQUQLFOMPYWACS-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/48—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
- C07C51/44—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation
- C07C51/46—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation by azeotropic distillation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Fatty acids containing up to 4 carbon atoms are extracted from their aqueous solutions by a mixture of a trialkyl phosphate and a hydrophobic diluent which forms an azeotropic mixture with water of lower boiling-point than that of the acids, the diluent, or water or any other azeotropic mixture formed by two or more of these substances. The extract may then be distilled to remove first the diluent/water azeotrope and then the fatty acids (see Group III). The invention may be used to recover the acids produced by the fermentation process of Specification 689,412. The extraction may be performed on a batch or in a continuous manner with concurrent or countercurrent flow of the two phases. In examples: (1), (2) and (4) propionic acid is extracted from its aqueous solution by a mixture of tributyl phosphate and benzene or ethylene chloride; (3) molasses fermented with propionbacterium arabinosum is acidified to pH4 with sulphuric acid and extracted with a mixture of tributyl phosphate and benzene. The extract is distilled to obtain a mixture of acetic, propionic and butyric acids.ALSO:Fatty acids containing up to 4 carbon atoms are extracted from their aqueous solutions by a mixture of a trialkyl phosphate and a hydrophobe diluent which forms an azeotropic mixture with water of lower boiling point than that of the acids, the diluent, or water or any other azeotropic mixture formed by two or more of these substances. The extracts are then distilled to remove first the diluent/water azeotrope and then the fatty acids. The invention may be used to recover the acids produced by the fermentation process of Specification 689,412, [Group IV (b)]. Specified trialkyl phosphates are tripropyl-, tributyl, tri-(butoxy-ethyl), tri-(2-ethylhexyl)-, and tri-(chlor-ethyl)-phos-(2-ethylhexyl)-, and tri(chlor-ethyl)-phosphates. Specified hydrophobe diluents are benzene, toluene, cyclohexane, methylene chloride, trichloroethylene and 1.2-dichloroethane. Some of the diluent may be added to the extract after the extraction process and before or after distillation has commenced. Distillation is preferably effected at below 150 DEG C at sub-atmospheric pressures to minimize hydrolysis of the trialkyl phosphate. If a strong acid is present in the extract a basic substances e.g. sodium citrate, bicarbonate or acetate or dibasic sodium phosphate is added thereto before the distillation. In examples (2) propionic acid is extracted from its aqueous solution with a mixture of tributyl phosphate and benzene and the extract distilled first at atmospheric pressure to remove the benzene/water azeotrope and then at 35-43 mm. of mercury to remove the propionic acid; (3) molasses fermented with propionibacterium arabinosum is acidified to pH4 with sulphuric acid and extracted with a mixture of tributyl phosphate and benzene. The extract is agitated with dibasic sodium phosphate, distilled at atmospheric pressure to remove the water/benzene azeotrope and a mixture of acetic, propionic and butyric acids is then flashed off by reducing the pressure to 35 mm. while continuing the heating.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US689411XA | 1949-12-17 | 1949-12-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB689411A true GB689411A (en) | 1953-03-25 |
Family
ID=22085690
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB30666/50A Expired GB689411A (en) | 1949-12-17 | 1950-12-15 | Concentration of organic acids |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB689411A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104024209A (en) * | 2011-12-01 | 2014-09-03 | 塔明克芬兰公司 | Method for recovering and purifying propionic acid |
| CN105709451A (en) * | 2014-12-23 | 2016-06-29 | 坎普利斯公司 | Process system for separating chemicals, distillation column arrangement, and method of separating chemicals |
-
1950
- 1950-12-15 GB GB30666/50A patent/GB689411A/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104024209A (en) * | 2011-12-01 | 2014-09-03 | 塔明克芬兰公司 | Method for recovering and purifying propionic acid |
| EP2785678A1 (en) * | 2011-12-01 | 2014-10-08 | Taminco Finland Oy | Method for recovering and purifying propionic acid |
| US9024066B2 (en) | 2011-12-01 | 2015-05-05 | Taminco Finland | Method for recovering and purifying propionic acid |
| CN104024209B (en) * | 2011-12-01 | 2015-11-25 | 塔明克芬兰公司 | Method for recovery and purification of propionic acid |
| CN105709451A (en) * | 2014-12-23 | 2016-06-29 | 坎普利斯公司 | Process system for separating chemicals, distillation column arrangement, and method of separating chemicals |
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