GB2251248A - Preparing tall oil by hydrochloric acid extraction - Google Patents
Preparing tall oil by hydrochloric acid extraction Download PDFInfo
- Publication number
- GB2251248A GB2251248A GB9126949A GB9126949A GB2251248A GB 2251248 A GB2251248 A GB 2251248A GB 9126949 A GB9126949 A GB 9126949A GB 9126949 A GB9126949 A GB 9126949A GB 2251248 A GB2251248 A GB 2251248A
- Authority
- GB
- United Kingdom
- Prior art keywords
- tall oil
- acid
- hydrochloric acid
- soft soap
- separated
- 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.)
- Granted
Links
- 239000003784 tall oil Substances 0.000 title claims abstract description 80
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 title claims abstract description 44
- 238000000605 extraction Methods 0.000 title 1
- 239000000344 soap Substances 0.000 claims abstract description 34
- 238000000034 method Methods 0.000 claims abstract description 14
- 239000002253 acid Substances 0.000 claims description 25
- 230000020477 pH reduction Effects 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 13
- 239000001117 sulphuric acid Substances 0.000 abstract description 13
- 235000011149 sulphuric acid Nutrition 0.000 abstract description 13
- 239000006227 byproduct Substances 0.000 abstract description 3
- 239000001913 cellulose Substances 0.000 abstract description 3
- 229920002678 cellulose Polymers 0.000 abstract description 3
- 239000000203 mixture Substances 0.000 description 18
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 15
- 238000004458 analytical method Methods 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 10
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 10
- 150000007513 acids Chemical class 0.000 description 9
- 235000014113 dietary fatty acids Nutrition 0.000 description 8
- 239000000194 fatty acid Substances 0.000 description 8
- 229930195729 fatty acid Natural products 0.000 description 8
- 150000004665 fatty acids Chemical class 0.000 description 7
- 238000004817 gas chromatography Methods 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 description 5
- BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 description 5
- QUUCYKKMFLJLFS-UHFFFAOYSA-N Dehydroabietan Natural products CC1(C)CCCC2(C)C3=CC=C(C(C)C)C=C3CCC21 QUUCYKKMFLJLFS-UHFFFAOYSA-N 0.000 description 5
- NFWKVWVWBFBAOV-UHFFFAOYSA-N Dehydroabietic acid Natural products OC(=O)C1(C)CCCC2(C)C3=CC=C(C(C)C)C=C3CCC21 NFWKVWVWBFBAOV-UHFFFAOYSA-N 0.000 description 5
- NFWKVWVWBFBAOV-MISYRCLQSA-N dehydroabietic acid Chemical compound OC(=O)[C@]1(C)CCC[C@]2(C)C3=CC=C(C(C)C)C=C3CC[C@H]21 NFWKVWVWBFBAOV-MISYRCLQSA-N 0.000 description 5
- 229940118781 dehydroabietic acid Drugs 0.000 description 5
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 4
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 4
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 4
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 4
- 239000005642 Oleic acid Substances 0.000 description 4
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 4
- 235000020778 linoleic acid Nutrition 0.000 description 4
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 4
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 239000005864 Sulphur Substances 0.000 description 3
- 229920005610 lignin Polymers 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000004537 pulping Methods 0.000 description 3
- RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 2
- OPZZWWFHZYZBRU-UHFFFAOYSA-N butanedioic acid;butane-1,1-diol Chemical compound CCCC(O)O.OC(=O)CCC(O)=O OPZZWWFHZYZBRU-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000010865 sewage Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 235000018185 Betula X alpestris Nutrition 0.000 description 1
- 235000018212 Betula X uliginosa Nutrition 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- -1 acids fatty acids Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000010413 mother solution Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B13/00—Recovery of fats, fatty oils or fatty acids from waste materials
- C11B13/005—Recovery of fats, fatty oils or fatty acids from waste materials of residues of the fabrication of wood-cellulose (in particular tall-oil)
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
- Y02W30/00—Technologies for solid waste management
- Y02W30/50—Reuse, recycling or recovery technologies
- Y02W30/74—Recovery of fats, fatty oils, fatty acids or other fatty substances, e.g. lanolin or waxes
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Abstract
The present invention relates to a procedure for producing tall oil from tall oil soft soap produced as a by-product in the cellulose industry. The procedure comprises the steps of acidifying the tall oil soft soap with hydrochloric acid and separating the tall oil thus obtained. Hydrochloric acid replaces the more usual sulphuric acid and is ecologically more acceptable.
Description
I 2231243 1 Production of tall oil The present invention relates to c
procedure for producing tall oil from tall oil soft soap produced as a by-product in the cellulose industry, and by separating the tall oil thus produced from the mother water and lignin.
As a by-product of the cellulose industry valuable tall oil soft soap is produced, gathering in pulp production on the surface of the solution while concentrating the mother solution, i.e. in conjunction with water vaporization. The soft soap is shaved off from the surface of the vessel and acidified, whereby tall oil is produced. The tall oil is distilled further, whereby valuable rosin acids and fatty acids are obtained as distillation fractions.
The reaction is chemically simple, and the rosin and fatty acids present therein in the form of sodium salts are made to react with sulphuric acid, whereby respective carboxyl acids and sodium sulphate are produced.
For the acidification of tall oil soft soap, sulphuric acid has been used, this being well suited for said purpose since it makes possible the addition of neutralized sulphuric acid in the chemical cycle of the pulp mill. The sodium sulphate thus produced is a useful addition in substituting the sulphur losses in the pulping process. However, owing to the limitations concerning the protection of the environment, the pulp mills have reduced their sulphur releases to the extent that the sulphuric acid used in the acidification process of tall oil soft soap no longer can be used to substitute the considerably reduced sulphur losses of the pulp mill. Therefore, endeavours have been made to develop acidification alternatives in producing tall oil.
2 In conjunction with the present invention it was surprisingly found that for acidifying tall oil soft soap, monovalent hydrochloric acid can be used instead of bivalent sulphuric acid. The amount of hydrochloric acid needed for an equal amount of tall oil soft soap is equal to that of the bivalent sulphuric acid. The hydrochloric acid is low in price, it is readily available, and the sewage produced In acidifying the hydrochloric acid is ecologically more beneficial than the sewage produced in acidifying sulphuric acid.
As regards the corrosion properties, sulphurIc acid and hydrochloric acid are very similar. In certain conditions and in certain concentrations, however, the sulpuric acid is more corroding than the hydrochloric acid, because of which the use of sulphuric acid is recommended, too.
The essential characteristics of the invention are presented in the accompanying claims.
For hydrochloric acid, dilute, concentrated or gaseous hydrochloric acid can be used on the condition that its amount is sufficient for neutralizing the fatty and rosin acids present in the tall oil soft soap. Excess use causes extra costs.
The acidification of tall oil soft soap is carried out in the temperature range 60 to 2200C, preferably in the range 85 to 100C. At temperatures over 1OWC, a pressure reaction is to be considered. The reaction time is not very significant but the best time was found to be 10 to 30 minutes. No advantage was gained from a longer.time.
The changes in the quality of the tall o.11 soft soap are dependent on the quality of timber used in manufacturing pulp. When pulping only pine, good quality tall oil soft 3 soap is produced, the acid number of the tall oil obtained therefrom being 140 to 160 mg KOH/g and the rosin acid content being 30 to 50. However, in pulping birch the quality of the soft soap changes so that the acid number of the respective tall oil is 100 to 120 mg KOH/g, being even lower, the rosin acid content being then 20 to 30%. Irrespective of the quality, hydrochloric acid can appropriately be used in acidification process of tall oils instead of the sulphuric acid.
After the acidification process, the tall oil layer can be separated from the mother water and the lignin layers either by allowing the layers to be separated or by centrifugalizing them off with a centrifuge.
The invention is illustrated with the following examples.
Example 1
42 ml of 37% hydrochloric acid were used and 42 ml water were added. The mixture was heated to 800C. In the mixture 190 g of 50% tall oil soft soap were added gradually. It was mixed for 10 minutes at 800C and 15 minutes at 900C, whereafter the mixture was poured into a graduated glass. The layers were allowed to be separated at 80C for 30 minutes, whereafter the tall oil could be decanted off. The analyses of the tall oil thus obtained were as follows.
yield % 57.5 acid number mg KOH/g 150 rosin acids % 34 unsaponifiable 12 fatty acids % 54 Calculated: separated tall oil/tall oil soft soap 100% 4 Example 2 ml water were used and 50 ml of 40% sulphuric acid were added. The mixture was heated to 9WC and 200 g of 450C tall oil soft soap were added. It was mixed for 10 minutes at 800C and 15 minutes at 900C, whereafter the mixture was poured into a graduated glass. The layers were allowed to be separated at 80C for 30 minutes, whereafter the tall oil could be decanted off. The analyses of the tall oil thus obtained were as follows.
yield % acid number mg KOH/g rosin acids % unsaponifiable % fatty acids % 150 35 12 53 Calculated: separated tall oil/tall oil soft soap 100% Using the Examples 1 and 2, a gas chromatography analysis was carried out; for the tower, a 25 meter quartz capillary tower as the butane diol succinate liquid phase (BDS) was used. The run was carried out isothermically at 1970C. The main components were as follows.
Example 1 Example 2 9-C18:1 14.6% 14.4% (oleic acid) 9.12-C18:2 20.5% 19.9% (linoleic acid) abietic acid 13.1% 11.7% dehydroabietic acid 7% 7% It can be seen in the above results that in using hydrochloric acid, both the quality and yield of the tall oil are entirely comparable with the tall oil produced using sulphuric acid.
Examnle 3 34 ml of 37 hydrochloric acid were used and 34 ml water were added thereto. The mixture was heated to 900C. Into the mixture 280 g of tall oil soft soap at 50C were added gradually. It was mixed for 30 minutes at 90C, whereafter the mixture was poured into a graduated glass. The layers were allowed to be separated at 900C for 60 minutes, whereafter the tall oil could be decanted off. The analyses of the tall oil thus obtained were as follows.
yield acid number mg KOH/g water rosin acids % unsaponifiable 21 108 4.5 34 12 Calculated: separated tall oil/tall oil soft soap 100 ExamDle 4 34 ml of 37 hydrochloric acid were used and 34 ml water were added. The mixture was heated to 9WC, and 150 g of tall oil soft soap at 50C were added. It was mixed for 30 minutes at 900C, whereafter the mixture was poured into a graduated glass. The layers were allowed to be separated at 900C for 60 minutes, whereafter the tall oil could be decanted off. The analyses of the tall oil thus obtained were as follows.
6 yield % acid number mg KOH/g water % rosin acids fatty acids unsaponifiable % 37% 149 1.5 32.7 51.4 15.9 Calculated: separated tall oil/tall oil soft soap 100 From the Examples 3 and 4 a gas chromatography analysis was made; for the tower a 25 meter quartz capillary tower was used as the butane diol succinate liquid Dhase (BDS). The run was carried out isothermically at 197'C. The main components were as follows.
Example 3
Example 4
9-C18:1 14.3% 17.7% (oleic acid) 9.12-C18:2 19.3%' 24.7% (linoleic acid) abietic acid 11.6% dehydroabietic acid 7.8% 16.0% 5.9% It is seen from the above results that a change in the soap/hydrochloric acid ratio makes no great effect on the quality of tall oil being separated, but only on the layer separation rate.
Exami:)1e 5 34 ml of 37 hydrochloric acid were used and 34 ml water were added thereto. The acid mixture was heated to 600C and 190 g of 500C tall oil soft soap were added to the 1 7 mixture. It was mixed for 30 minutes at 6WC, whereafter the mixture was poured into a graduated glass. The layers were allowed to be separated for 75 minutes, whereafter the tall oil could be decanted off. The analyses of the tall oil thus obtained were as follows.
yield % 26 acid number mg KOH/g 151 rosin acids % 35 unsaponifiable 13 fatty acids % 52 Calculated: separated tall oil/tall oil soft soap 100 % One may see from the results that at a low temperature like above the yield becomes smaller and the separation of the layers more difficult.
Example 6
63 g of tall oil soft soap, 11.3 ml of concentrated 37 hydrochloric acid and 11.3 ml water were used. The ingredients were inserted in an autoclave and the temperature was raised to 1700C. It was allowed to be mixed for 30 minutes at 170C, whereafter the mixture was allowed to cool down and the separated tall oil was decanted off. The analyses of the tall oil thus obtained were as follows.
yield acid number mg KOH/g rosin acids unsaponifiable fatty acids % 134 32.9 14.7 52.4 8 Calculated: separated tall oil/tall oil soft soap 1 From the tall oil obtained in the manner described in Examples 5 and 6 a gas chromatography analysis was carried out (BDS tower, 197C, lsothermic run). The main components of the tall oil were as follows.
Example 5
Example 6
9-C18:1 14.7% 13.9% 9.12-C18:2 20.4% 18.2% abietic acid 19.7% 18.8% dehydroabietic acid 6.8% 10.2% Example 7
34 ml of concentrated 37% hydrochloric acid were used and 34 ml water were added thereto. The mixture was heated to 970C and 190 g of 500C tall oil soft soap were added. It was mixed for 30 minutes at 970C, whereafter the mixture was poured into a graduated glass, and after a while, the separated lignin and tall oil layer were decanted off from the mother water. The mixture was poured into a centrifuge tube and was centrifugalized 5300 x g for 20 minutes. The analyses of the tall oil thus obtained were as follows.
yield acid number mg KOH/g unsaponifiable 47 152.5 13.2 Calculated: separated tall oil/tall oil soft soap 100% 9 On the basis of a gas chromatography analysis (BDS tower, 197C, isothermic run), the main components of the tall oil were as follows.
9-C18: 1 (oleic acid) 9. 12-C18:2 (linoleic acid) abietic acid dehydroabietic acid 15.3 14% 25% 7.8% On the basis of analyses, the tall oil separated by centrifugalizing is of good quality.
ExamiDle 8 63 g soap, 11.3 ml concentrated 37% hydrochloric acid and 11.3 ml water were used. The ingredients were inserted into an autoclave and the temperature was raised to 2200C, the pressure being 14 bar. It was allowed to be mixed for 30 minutes at 2200C, whereafter the mixture was allowed to cool and the separated tall oil was decanted off. The analyses of the tall oil thus obtained were as follows.
yield 3% acid number mg KOH/g rosin acids unsaponifiable fatty acids % 49 124 29 19 48 Calculated: separated tall oil/tall oil soft soap 100% The low acid number of the separated tall oil is obviously due to esterification or decarboxylation.
From the tall oil obtained as in Example 8 a gas chromatography analysis was performed (BDS tower, 19711C, isothermic run). The main components of the tall oil were as follows.
9-C18: 1 (oleic acid) 9.12-C18:2 (linoleic acid) abietic acid dehydroabietic acid 15.5% 15. 5-% 11. 3% 15.59% On the basis of the gas chromatography analysis it seems to be that differences compared with the earlier ones commence being found in acid distributions at said high temperature; isomerisation of linoleic and abietic acids taking place.
The above examples are illustrative embodiments of the present invention. Many other processes falling within the scope of the present invention will be apparent to persons skilled in the art.
11
Claims (6)
1. A procedure for producing tall oil from tall oil soft soap by acidifying tall oil soft soap and by separating the tall oil thus obtained, characterized in that the acidification is carried out with hydrochloric acid.
2. A procedure according to claim 1, characterized in that the acidification is done at 600 to 2200C.
3. A procedure according to claim 2, characterised in that the acidification is done at 850 to 1000C.
4. A procedure according to claim 1 or 2 characterized in that the acidification reaction is carried out under pressurized conditions at a temperature over 1000C.
5. A procedure according to any preceding claim, characterized in that the acid number of the tall oil thus 0 obtained is 100 to 160 mg KOH/g.
2
6. A procedure for producing tall oil from tall oil soft soap substantially as hereinbefore described in example 1 and examples 3 to 8.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI906451A FI93868C (en) | 1990-12-28 | 1990-12-28 | Manufacture of tall oil |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB9126949D0 GB9126949D0 (en) | 1992-02-19 |
| GB2251248A true GB2251248A (en) | 1992-07-01 |
| GB2251248B GB2251248B (en) | 1994-03-30 |
Family
ID=8531663
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB9126949A Expired - Fee Related GB2251248B (en) | 1990-12-28 | 1991-12-19 | Production of tall oil |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPH06340890A (en) |
| AT (1) | AT399172B (en) |
| CA (1) | CA2056836C (en) |
| CH (1) | CH682238A5 (en) |
| CZ (1) | CZ281616B6 (en) |
| DE (1) | DE4141913C2 (en) |
| ES (1) | ES2054541B1 (en) |
| FI (1) | FI93868C (en) |
| FR (1) | FR2671096B1 (en) |
| GB (1) | GB2251248B (en) |
| IT (1) | IT1252221B (en) |
| NO (1) | NO178897C (en) |
| PL (1) | PL168096B1 (en) |
| RU (1) | RU2029782C1 (en) |
| SE (1) | SE505831C2 (en) |
| SK (1) | SK279772B6 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994011571A1 (en) * | 1992-11-10 | 1994-05-26 | Lt-Dynamics Oy | Method for acidification of soap with sodium bisulphite solution |
| WO2016040915A1 (en) * | 2014-09-12 | 2016-03-17 | Arizona Chemical Company, Llc | Process for recovering crude tall oil |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH275810A (en) * | 1948-04-16 | 1951-06-15 | Jihoceske Papirny Narodni Podn | Process for the production of tall oil. |
| GB695702A (en) * | 1949-06-29 | 1953-08-19 | Ernest Segessemann | Improved tall oil treatment |
| US2530809A (en) * | 1949-08-23 | 1950-11-21 | Pittsburgh Plate Glass Co | Fractionation of tall oil |
| US3109839A (en) * | 1962-02-26 | 1963-11-05 | Sharples Corp | Production of organic acids |
| US3575952A (en) * | 1969-10-02 | 1971-04-20 | Scm Corp | Tall oil recovery |
| US3804819A (en) * | 1972-05-03 | 1974-04-16 | Scm Corp | Recovery of fatty acids from tall oil heads |
| US4495095A (en) * | 1983-04-04 | 1985-01-22 | Union Camp Corporation | Acidulation and recovery of crude tall oil from tall oil soaps |
| US4483791A (en) * | 1983-06-22 | 1984-11-20 | Sylvachem Corporation | Recovery of fatty acids from tall oil heads |
| GB8915263D0 (en) * | 1989-07-03 | 1989-08-23 | Unilever Plc | Process for soap splitting using a high temperature treatment |
-
1990
- 1990-12-28 FI FI906451A patent/FI93868C/en not_active IP Right Cessation
-
1991
- 1991-12-03 CA CA 2056836 patent/CA2056836C/en not_active Expired - Fee Related
- 1991-12-09 CH CH3613/91A patent/CH682238A5/de unknown
- 1991-12-16 IT IT91MI3363 patent/IT1252221B/en active IP Right Grant
- 1991-12-18 AT AT0251091A patent/AT399172B/en not_active IP Right Cessation
- 1991-12-18 DE DE4141913A patent/DE4141913C2/en not_active Expired - Fee Related
- 1991-12-19 GB GB9126949A patent/GB2251248B/en not_active Expired - Fee Related
- 1991-12-20 ES ES9102851A patent/ES2054541B1/en not_active Expired - Lifetime
- 1991-12-20 SE SE9103811A patent/SE505831C2/en not_active IP Right Cessation
- 1991-12-23 PL PL91292944A patent/PL168096B1/en unknown
- 1991-12-27 NO NO915117A patent/NO178897C/en unknown
- 1991-12-27 RU SU5010424 patent/RU2029782C1/en active
- 1991-12-27 CZ CS914119A patent/CZ281616B6/en not_active IP Right Cessation
- 1991-12-27 SK SK4119-91A patent/SK279772B6/en unknown
- 1991-12-27 FR FR9116224A patent/FR2671096B1/en not_active Expired - Fee Related
-
1992
- 1992-01-02 JP JP1818792A patent/JPH06340890A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994011571A1 (en) * | 1992-11-10 | 1994-05-26 | Lt-Dynamics Oy | Method for acidification of soap with sodium bisulphite solution |
| WO2016040915A1 (en) * | 2014-09-12 | 2016-03-17 | Arizona Chemical Company, Llc | Process for recovering crude tall oil |
| US10041020B2 (en) | 2014-09-12 | 2018-08-07 | Kraton Chemical, Llc | Process for recovering crude tall oil |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2056836A1 (en) | 1992-06-29 |
| NO178897B (en) | 1996-03-18 |
| FI93868B (en) | 1995-02-28 |
| SK279772B6 (en) | 1999-03-12 |
| ATA251091A (en) | 1994-08-15 |
| AT399172B (en) | 1995-03-27 |
| PL168096B1 (en) | 1996-01-31 |
| PL292944A1 (en) | 1992-09-07 |
| RU2029782C1 (en) | 1995-02-27 |
| CS411991A3 (en) | 1992-07-15 |
| SE9103811D0 (en) | 1991-12-20 |
| FI93868C (en) | 1995-06-12 |
| ES2054541B1 (en) | 1995-02-01 |
| IT1252221B (en) | 1995-06-05 |
| GB2251248B (en) | 1994-03-30 |
| GB9126949D0 (en) | 1992-02-19 |
| ITMI913363A0 (en) | 1991-12-16 |
| CZ281616B6 (en) | 1996-11-13 |
| JPH06340890A (en) | 1994-12-13 |
| SE505831C2 (en) | 1997-10-13 |
| FR2671096A1 (en) | 1992-07-03 |
| NO178897C (en) | 1996-06-26 |
| FI906451A0 (en) | 1990-12-28 |
| DE4141913C2 (en) | 1999-04-29 |
| NO915117D0 (en) | 1991-12-27 |
| CH682238A5 (en) | 1993-08-13 |
| CA2056836C (en) | 1999-05-04 |
| SE9103811L (en) | |
| FI906451A (en) | 1992-06-29 |
| DE4141913A1 (en) | 1992-07-02 |
| FR2671096B1 (en) | 1994-10-07 |
| ES2054541A1 (en) | 1994-08-01 |
| ITMI913363A1 (en) | 1993-06-16 |
| NO915117L (en) | 1992-06-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19991219 |