SE505831C2 - Process for producing tall oil from tall oil soap - Google Patents
Process for producing tall oil from tall oil soapInfo
- Publication number
- SE505831C2 SE505831C2 SE9103811A SE9103811A SE505831C2 SE 505831 C2 SE505831 C2 SE 505831C2 SE 9103811 A SE9103811 A SE 9103811A SE 9103811 A SE9103811 A SE 9103811A SE 505831 C2 SE505831 C2 SE 505831C2
- Authority
- SE
- Sweden
- Prior art keywords
- tall oil
- acid
- soap
- soft
- hydrochloric acid
- Prior art date
Links
- 239000003784 tall oil Substances 0.000 title claims abstract description 62
- 239000000344 soap Substances 0.000 title claims abstract description 28
- 238000000034 method Methods 0.000 title claims abstract description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 38
- 239000002253 acid Substances 0.000 claims description 21
- 230000020477 pH reduction Effects 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 17
- 239000006227 byproduct Substances 0.000 abstract 1
- 229920002678 cellulose Polymers 0.000 abstract 1
- 239000001913 cellulose Substances 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 150000007513 acids Chemical class 0.000 description 9
- 239000011347 resin Substances 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- RSWGJHLUYNHPMX-UHFFFAOYSA-N 1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid Chemical compound C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- 150000004665 fatty acids Chemical class 0.000 description 6
- 238000004817 gas chromatography Methods 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
- 239000003921 oil Substances 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
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 4
- 239000005642 Oleic acid Substances 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
- 229920005610 lignin Polymers 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000010665 pine oil Substances 0.000 description 3
- 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
- 239000007788 liquid Substances 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- QRDZSRWEULKVNW-UHFFFAOYSA-N 6-hydroxy-2-oxo-1h-quinoline-4-carboxylic acid Chemical compound C1=C(O)C=C2C(C(=O)O)=CC(=O)NC2=C1 QRDZSRWEULKVNW-UHFFFAOYSA-N 0.000 description 1
- 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
- 235000008578 Pinus strobus Nutrition 0.000 description 1
- 240000007320 Pinus strobus Species 0.000 description 1
- 238000005119 centrifugation Methods 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
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 230000035484 reaction time 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
Description
505 831 2 oljetvål är lika stor som den som erfordras för den tvåvärda svavelsyran. Saltsyran har lågt pris, är lätt tillgänglig och det avfall som bildas vid surgörande med saltsyran är ekologiskt mera gynnsam än det avfall som produceras i surgörande med svavelsyra. 505 831 2 oil soap is as large as that required for the divalent sulfuric acid. The hydrochloric acid has a low price, is easily available and the waste formed during acidification with the hydrochloric acid is ecologically more favorable than the waste produced in acidification with sulfuric acid.
Beträffande korrosionsegenskaperna är svavelsyra och saltsyra mycket lika. Under vissa betingelser och i vissa koncentra- tioner är emellertid svavelsyra mera korrosiv än saltsyra, av vilken anledning svavelsyran även rekommenderas.In terms of corrosion properties, sulfuric acid and hydrochloric acid are very similar. However, under certain conditions and in certain concentrations, sulfuric acid is more corrosive than hydrochloric acid, for which reason sulfuric acid is also recommended.
De väsentliga kännetecknen hos uppfinningen presenteras i de efterföljande patentkraven.The essential features of the invention are set forth in the appended claims.
Avseende saltsyra kan utspädd, koncentrerad eller gasformig saltsyra användas under förutsättning att mängden därav är tillräcklig för att neutralisera de fett- och hartssyror som föreligger i den mjuka talloljetvålen. Användning av överskott förorsakar extra kostnader.With respect to hydrochloric acid, dilute, concentrated or gaseous hydrochloric acid may be used provided that the amount thereof is sufficient to neutralize the fatty and resin acids present in the soft tall oil soap. Use of surplus causes extra costs.
Surgöring av mjuk talloljetvål genomföres i temperaturområdet so till 220 °c, företrädesvis i området ss till loo °c. vid temperaturer över 100 °C, skall en tryckreaktion beaktas.Acidification of soft tall oil soap is carried out in the temperature range s0 to 220 ° C, preferably in the range ss to loo ° c. at temperatures above 100 ° C, a pressure reaction must be taken into account.
Reaktionstiden är inte särskilt betydelsefull, men den bästa tiden befanns vara 10 till 30 minuter. Ingen fördel erhölls av en längre tid.The reaction time is not very significant, but the best time was found to be 10 to 30 minutes. No benefit was obtained for a long time.
Förändringarna i kvalité hos den mjuka talloljetvålen beror av den kvalité av timmer som användes i framställning av massa. Vid massaframställning av enbart tall erhålles en mjuk talloljetvål, av god kvalité där syratalet hos den därifrån erhållna talloljan är 140 till 160 mg KOH/g och hartssyrahalten är 30 till 50 %. Vid massaframställning av björk ändras tvålens kvalité, varvid syratalet hos ifråga- varande tallolja är 100 till 120 mg KOH/g och ännu lägre, och varvid hartssyrahalten är 20 till 30 %. Oberoende av 5Û5 831 3 kvalitén kan saltsyra på riktigt sätt användas i förfarandet vid surgöring av talloljor istället för svavelsyran.The changes in the quality of the soft tall oil soap depend on the quality of the timber used in the production of pulp. In mass production of pine alone, a soft pine oil soap is obtained, of good quality where the acid number of the pine oil obtained therefrom is 140 to 160 mg KOH / g and the resin acid content is 30 to 50%. In the mass production of birch, the quality of the soap changes, the acid number of the tall oil in question being 100 to 120 mg KOH / g and even lower, and the resin acid content being 20 to 30%. Regardless of the quality, hydrochloric acid can be properly used in the process of acidifying tall oils instead of the sulfuric acid.
Efter surgörings-förfarandet kan talloljeskiktet avskiljas från modervatten- och ligninskikten, antingen genom att låta skikten separera eller genom att avcentrifugera dem med en centrifug.After the acidification process, the tall oil layer can be separated from the mother water and lignin layers, either by allowing the layers to separate or by centrifuging them with a centrifuge.
Uppfinningen belyses med följande exempel.The invention is illustrated by the following examples.
Exempel 1 42 ml 37 % saltsyra användes och 42 ml vatten tillsattes.Example 1 42 ml of 37% hydrochloric acid were used and 42 ml of water were added.
Blandningen uppvärmdes till 80 °C. I blandningen tillsattes 190 g 50 % mjuk talloljetvål gradvis. Den blandades i 10 minuter vid 80 °C och 15 minuter vid 90 °C, varefter blandnin- gen hälldes i ett graderat glas. Skikten fick separera vid 80 °C under 30 minuter varefter talloljan kunde avdekanteras.The mixture was heated to 80 ° C. To the mixture was gradually added 190 g of 50% soft tall oil soap. It was mixed for 10 minutes at 80 ° C and 15 minutes at 90 ° C, after which the mixture was poured into a graduated glass. The layers were allowed to separate at 80 ° C for 30 minutes after which the tall oil could be decanted.
Analyserna av den sålunda erhållna talloljan var såsom följer.The analyzes of the tall oil thus obtained were as follows.
Utbyte.* % 57,5 Syratal mg KOH/g 150 Hartssyror 34 Icke förtvålningsbar 12 Fettsyror 54 * Beräknat: Avskild tallolja/mjuk talloljetvål * 1oø % Exempel 2 50 ml vatten användes och 50 ml 40 % svavelsyra tillsattes.Yield. *% 57.5 Acid number mg KOH / g 150 Resin acids 34 Non-saponifiable 12 Fatty acids 54 * Calculated: Separated tall oil / soft tall oil soap * 100% Example 2 50 ml of water were used and 50 ml of 40% sulfuric acid were added.
Blandningen uppvärmdes till 90 °C och 200 g 45 °C mjuk talloljetvål tillsattes. Den blandades i 10 minuter vid 80 °C och 15 minuter vid 90 °C, varefter blandningen hälldes i ett graderat glas. Skikten fick separera vid 80 °C under 30 minuter varefter talloljan kunde avdekanteras. Analyserna av den sålunda erhållna talloljan var såsom följer. 505 831 4 Utbyte * % ss Syratal mg KOH/g 150 Hartssyror % 35 Icke förtvålningsbar % 12 Fettsyror % 53 * Beräknat: Avskiia tailolja/mjuk tailoljetvåi * 1oo z Med användning av Exemplen 1 och 2 genomfördes en gaskroma- tografi-analys; såsom torn användes ett 25 m kvartskapillär- torn som den flytande butandiol-succinat-fasen (BDS).The mixture was heated to 90 ° C and 200 g of 45 ° C soft tall oil soap was added. It was mixed for 10 minutes at 80 ° C and 15 minutes at 90 ° C, after which the mixture was poured into a graduated glass. The layers were allowed to separate at 80 ° C for 30 minutes after which the tall oil could be decanted. The analyzes of the tall oil thus obtained were as follows. 505 831 4 Yield *% ss Acid number mg KOH / g 150 Resin acids% 35 Non-saponifiable% 12 Fatty acids% 53 * Calculated: Separate tail oil / soft tail oil soap * 1000 z Using a gas chromatography analysis using Examples 1 and 2; As a tower, a 25 m quartz capillary tower was used as the liquid butanediol succinate (BDS) phase.
Körningen genomfördes isotermt vid 197 °C. Huvudkomponenterna var såsom följer.The run was performed isothermally at 197 ° C. The main components were as follows.
Exempel 1 Exempel 2 9-C18:1 14,6 % 14,4 % (oleinsyra) 9,12-ciszz 20,5 % 19,9 % (linoleinsyra) abietinsyra 20,5 % 11,7 % dehydro-abietinsyra 7, % 7, % Det framgår av resultaten ovan, att vid användning av saltsyra, både kvalité och utbyte av talloljan är i sin helhet jämförbara med den tallolja som framställes med användning av svavelsyra.Example 1 Example 2 9-C18: 1 14.6% 14.4% (oleic acid) 9,12-cisz 20.5% 19.9% (linoleic acid) abietic acid 20.5% 11.7% dehydroabietic acid 7, % 7,% It appears from the results above, that when using hydrochloric acid, both the quality and yield of the tall oil are in their entirety comparable to the tall oil produced using sulfuric acid.
Exempel 3 34 ml 37 % saltsyra användes och 34 ml vatten tillsattes.Example 3 34 ml of 37% hydrochloric acid were used and 34 ml of water were added.
Blandningen uppvärmdes till 90 °C. I blandningen tillsattes 280 g mjuk talloljetvål vid 50 °C gradvis. Den blandades i 30 minuter vid 90 °C, varefter blandningen hälldes i ett graderat glas. Skikten fick separera vid 90 °C under 60 minuter varefter talloljan kunde avdekanteras. Analyserna av den sålunda erhållna talloljan var såsom följer. 505 831 Utbyte-* % 21 Syratal mg KOH/g 108 Vatten 4,5 Hartssyror 34 Icke förtvålningsbar 12 * Beräknat: Avskild tallolja/mjuk tailøljetvål * 1oo % EXemQGl Q 34 ml 37 % saltsyra användes och 34 ml vatten tillsattes.The mixture was heated to 90 ° C. Gradually 280 g of soft tall oil soap was added to the mixture at 50 ° C. It was mixed for 30 minutes at 90 ° C, after which the mixture was poured into a graduated glass. The layers were allowed to separate at 90 ° C for 60 minutes after which the tall oil could be decanted. The analyzes of the tall oil thus obtained were as follows. 505 831 Yield *% 21 Acid number mg KOH / g 108 Water 4.5 Resin acids 34 Non-saponifiable 12 * Calculated: Separated tall oil / soft tail oil soap * 100% EXemQGl Q 34 ml 37% hydrochloric acid was used and 34 ml water was added.
Blandningen uppvärmdes till 90 °C och 150 g mjuk talloljetvål vid 50 °C tillsattes. Den blandades i 30 minuter vid 90 °C, varefter blandningen hälldes i ett graderat glas. Skikten fick separera vid 90 °C under 60 minuter varefter talloljan kunde avdekanteras. Analyserna av den sålunda erhållna talloljan var såsom följer.The mixture was heated to 90 ° C and 150 g of soft tall oil soap at 50 ° C was added. It was mixed for 30 minutes at 90 ° C, after which the mixture was poured into a graduated glass. The layers were allowed to separate at 90 ° C for 60 minutes after which the tall oil could be decanted. The analyzes of the tall oil thus obtained were as follows.
Utbyte * % 37 Syratal mg KOH/g 149 Vatten 1,5 Hartssyror % 32,7 Fettsyror % 51,4 Icke förtvålningsbar % 15,9 * Beräknat: Avskild tailolja/mjuk talloljetvål * 1oo % Från Exemplen 1 och 2 genomfördes en gaskromatografianalys; såsom torn användes ett 25 m kvartskapillär-torn som den flytande butandiol-succinat-fasen (BDS). Körningen genomfördes isotermt vid 197 °C. Huvudkomponenterna var såsom följer. 505 831 6 Exempel 3 Exempel 4 9-Cl8zl 14,3 % 17,7 % (oleinsyra) 9,12-C18:2 19,3 % 24,7 % (linoleinsyra) abietinsyra 11,6 % 16,0 % dehydro-abietinsyra 7,8 % 5,9 % Det framgår av resultaten ovan, att en förändring i förhållan- det tvål/saltsyra inte har någon stor effekt å kvalitén av tallolja som avsepareras, men endast på skiktens separations- hastighet.Yield *% 37 Acid number mg KOH / g 149 Water 1.5 Resin acids% 32.7 Fatty acids% 51.4 Non-saponifiable% 15.9 * Calculated: Separated tail oil / soft tall oil soap * 100% From Examples 1 and 2 a gas chromatography analysis was performed; As a tower, a 25 m quartz capillary tower was used as the liquid butanediol succinate (BDS) phase. The run was performed isothermally at 197 ° C. The main components were as follows. 505 831 Example 3 Example 4 9-Cl8zl 14.3% 17.7% (oleic acid) 9,12-C18: 2 19.3% 24.7% (linoleic acid) abietic acid 11.6% 16.0% dehydro- abietic acid 7.8% 5.9% It appears from the results above that a change in the soap / hydrochloric acid ratio has no major effect on the quality of tall oil that is separated, but only on the separation speed of the layers.
Exempel 5 34 ml saltsyra användes och 50 ml vatten tillsattes. Bland- ningen uppvärmdes till 60 °C och 190 g 50 °C mjuk talloljetvål tillsattes. Den blandades i 30 minuter vid 60 °C, varefter blandningen hälldes i ett graderat glas. Skikten fick separera 75 minuter varefter talloljan kunde avdekanteras. Analyserna av den sålunda erhållna talloljan var såsom följer.Example 5 34 ml of hydrochloric acid were used and 50 ml of water were added. The mixture was heated to 60 ° C and 190 g of 50 ° C soft tall oil soap was added. It was mixed for 30 minutes at 60 ° C, after which the mixture was poured into a graduated glass. The layers were allowed to separate for 75 minutes after which the tall oil could be decanted. The analyzes of the tall oil thus obtained were as follows.
Utbyte * a; za Syratal mg KOH/g 151 Hartssyror % 35 Icke förtvålningsbar % 13 Fettsyror % 52 * Beräknat: Avsxiid tallolja/mjuk talloljetvål * 1oo æ Det framgår av resultaten att vid låg temperatur som ovan blir utbytet mindre och separationen av skikten svårare. 505 831 Egemgel 6 63 g mjuk talloljetvål, 11,3 g koncentrerad 37 % saltsyra och 11,3 ml vatten användes. Ingredienserna insattes i en autoklav och temperaturen höjdes till 170 °C. De fick blandas under 30 min vid 170 °C, varpå blandningen fick kallna och avseparerad tallolja avdekanterades. Analyserna av den sålunda erhållna talloljan var såsom följer.Yield * a; za Acid number mg KOH / g 151 Resin acids% 35 Non-saponifiable% 13 Fatty acids% 52 * Calculated: Avsxiid tall oil / soft tall oil soap * 1oo æ It appears from the results that at low temperature as above the yield becomes smaller and the separation of the layers more difficult. 505 831 Egemgel 6 63 g of soft tall oil soap, 11.3 g of concentrated 37% hydrochloric acid and 11.3 ml of water were used. The ingredients were placed in an autoclave and the temperature was raised to 170 ° C. They were allowed to mix for 30 minutes at 170 ° C, after which the mixture was allowed to cool and separated pine oil was decanted off. The analyzes of the tall oil thus obtained were as follows.
Utbyte * % so Syratal mg KOH/g 134 Hartssyror % 32,9 Icke förtvâlningsbar % 14,7 Fettsyror % 52,4 * Beräknat: Avskim tallolja/mjuk talløljetvål * 1oo æ Från talloljan erhållen på det sätt som beskrives i Exemplen 5 och 6 genomfördes en gaskromatografianalys (BDS-torn 197 °C, isoterm körning). Huvudkomponenterna i talloljan var såsom följer.Yield *% so Acid number mg KOH / g 134 Resin acids% 32.9 Non-digestible% 14.7 Fatty acids% 52.4 * Calculated: Defoam tall oil / soft tall oil soap * 100 æ From the tall oil obtained in the manner described in Examples 5 and 6 a gas chromatography analysis was performed (BDS tower 197 ° C, isothermal run). The main components of the tall oil were as follows.
Exempel 5 Exempel 6 9-Cl8:l 14,7 % 13,9 % 9,l2-Cl8:2 20,4 % 18,2 % abietinsyra 19,7 % 18,8 % dehydro-abietinsyra 6,8 % 10,2 % Exempel 7 34 ml koncentrerad 37 % saltsyra användes och 34 ml vatten tillsattes. Blandningen uppvärmdes till 97 °C och 190 g 50 °C mjuk talloljetvål tillsattes. Den blandades i 30 minuter vid 90 °C, varefter blandningen hälldes i ett graderat glas, och efter en stund avdekanterades de avseparerade lignin- och talloljeskikten från modervattnet. Blandningen 505 851 8 glas, och efter en stund avdekanterades de avseparerade lignin- och talloljeskikten från modervattnet. Blandningen hälldes i ett centrifugrör och centrifugerades 5300 x g under 20 min.Example 5 Example 6 9-Cl8: 1 14.7% 13.9% 9, 12-Cl8: 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 of water were added. The mixture was heated to 97 ° C and 190 g of 50 ° C soft tall oil soap was added. It was mixed for 30 minutes at 90 ° C, after which the mixture was poured into a graduated glass, and after a while the separated lignin and tall oil layers were decanted from the mother water. The mixture 505 851 8 glasses, and after a while the separated lignin and tall oil layers were decanted from the mother water. The mixture was poured into a centrifuge tube and centrifuged at 5300 x g for 20 minutes.
Analyserna av den sålunda erhållna talloljan var såsom följer.The analyzes of the tall oil thus obtained were as follows.
Utbyte * % 47 Syratal mg KOH/g 152,5 Icke förtvålningsbar % 13,2 * Beräknat: Avskild tallolja/mjuk talloljetvål * 100 % På basis av en gaskromatografianalys (BDS-torn 197 °C, isoterm körning), var huvudkomponenterna i talloljan såsom följer. 9-C18:l 15,3 % (oleinsyra) 9,12-c1s:2 14, % (linoleinsyra) abietinsyra 25, % dehydro-abietinsyra 7,8 % På basis av analyserna är genom centrifugering avseparerad a tallolja av god kvalite.Yield *% 47 Acid number mg KOH / g 152.5 Non-saponifiable% 13.2 * Calculated: Separated tall oil / soft tall oil soap * 100% Based on a gas chromatography analysis (BDS tower 197 ° C, isothermal run), the main components of the tall oil were as follows. 9-C18: l 15.3% (oleic acid) 9,12-c1s: 2 14,% (linoleic acid) abietic acid 25,% dehydro-abietic acid 7.8% On the basis of the analyzes, tall oil of good quality is separated by centrifugation.
Exempel 8 63 g tvål, 11,3 ml 37 % koncentrerad saltsyra och 11,3 ml vatten användes. Ingredienserna insattes i en autoklav och temperaturen höjdes till 220 °C, varvid trycket var 14 bar.Example 8 63 g of soap, 11.3 ml of 37% concentrated hydrochloric acid and 11.3 ml of water were used. The ingredients were placed in an autoclave and the temperature was raised to 220 ° C, the pressure being 14 bar.
Den fick blandas i 30 min vid 220 °C, varefter blandningen fick kallna och den avseparerade talloljan avdekanterades.It was allowed to mix for 30 minutes at 220 ° C, after which the mixture was allowed to cool and the separated tall oil was decanted off.
Analyserna av den sålunda erhållna talloljan var såsom följer. 505 831 9 utbyte * æ 49 Syratal mg KOH/g 124 Hartssyror % 29 Icke förtvålningsbar % 19 Fettsyror % 48 * * Beräknat: Avskíld tallolja/mjuk talloljetvål 100 % Det låga syratalet hos den separerade talloljan beror uppenbarligen på förestring eller dekarboxylering.The analyzes of the tall oil thus obtained were as follows. 505 831 9 exchange * æ 49 Acid number mg KOH / g 124 Resin acids% 29 Non-saponifiable% 19 Fatty acids% 48 * * Calculated: Peeled tall oil / soft tall oil soap 100% The low acid number of the separated tall oil is obviously due to esterification or decarboxylation.
Från den i Exempel 8 erhållna talloljan genomfördes en gaskromatografianalys (BDS-torn 197 °C, isoterm körning).From the tall oil obtained in Example 8, a gas chromatography analysis was performed (BDS tower 197 ° C, isothermal run).
Huvudkomponenterna i talloljan var såsom följer. 9-Cl8:1 15,5 % (oleinsyra) 9,12-C18:2 15,5 % (linoleinsyra) abietinsyra 11,3 % dehydro-abietinsyra 15,9 % På basis av gaskromatografi-analysen förefaller det vara så att skillnader jämfört med tidigare börjar påträffas i syradistribution vid denna höga temperatur, varvid isomeri- sering av linolein- och abietinsyror äger rum.The main components of the tall oil were as follows. 9-Cl8: 1 15.5% (oleic acid) 9,12-C18: 2 15.5% (linoleic acid) abietic acid 11.3% dehydro-abietic acid 15.9% Based on the gas chromatography analysis, it appears that differences compared to before, acid distribution begins to be found at this high temperature, whereby isomerization of linoleic and abietic acids takes place.
Claims (1)
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 |
|---|---|
| SE9103811L SE9103811L (en) | |
| SE9103811D0 SE9103811D0 (en) | 1991-12-20 |
| SE505831C2 true SE505831C2 (en) | 1997-10-13 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE9103811A SE505831C2 (en) | 1990-12-28 | 1991-12-20 | Process for producing tall oil from tall oil soap |
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) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI95723C (en) * | 1992-11-10 | 1996-04-11 | Lt Dynamics Oy | Method of acidifying soap with a large overdose of NaHSO3 solution |
| US10041020B2 (en) | 2014-09-12 | 2018-08-07 | Kraton Chemical, 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 DE DE4141913A patent/DE4141913C2/en not_active Expired - Fee Related
- 1991-12-18 AT AT0251091A patent/AT399172B/en not_active IP Right Cessation
- 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 FR FR9116224A patent/FR2671096B1/en not_active Expired - Fee Related
- 1991-12-27 CZ CS914119A patent/CZ281616B6/en not_active IP Right Cessation
- 1991-12-27 NO NO915117A patent/NO178897C/en unknown
- 1991-12-27 SK SK4119-91A patent/SK279772B6/en unknown
- 1991-12-27 RU SU5010424 patent/RU2029782C1/en active
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1992
- 1992-01-02 JP JP1818792A patent/JPH06340890A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| NO915117D0 (en) | 1991-12-27 |
| FI906451A0 (en) | 1990-12-28 |
| RU2029782C1 (en) | 1995-02-27 |
| ES2054541B1 (en) | 1995-02-01 |
| NO178897B (en) | 1996-03-18 |
| FR2671096A1 (en) | 1992-07-03 |
| GB2251248B (en) | 1994-03-30 |
| CH682238A5 (en) | 1993-08-13 |
| JPH06340890A (en) | 1994-12-13 |
| FI906451A (en) | 1992-06-29 |
| SE9103811L (en) | |
| PL168096B1 (en) | 1996-01-31 |
| ES2054541A1 (en) | 1994-08-01 |
| DE4141913A1 (en) | 1992-07-02 |
| DE4141913C2 (en) | 1999-04-29 |
| ITMI913363A1 (en) | 1993-06-16 |
| CA2056836A1 (en) | 1992-06-29 |
| FI93868C (en) | 1995-06-12 |
| CS411991A3 (en) | 1992-07-15 |
| NO915117L (en) | 1992-06-29 |
| ATA251091A (en) | 1994-08-15 |
| SE9103811D0 (en) | 1991-12-20 |
| SK279772B6 (en) | 1999-03-12 |
| GB9126949D0 (en) | 1992-02-19 |
| AT399172B (en) | 1995-03-27 |
| FI93868B (en) | 1995-02-28 |
| FR2671096B1 (en) | 1994-10-07 |
| ITMI913363A0 (en) | 1991-12-16 |
| CA2056836C (en) | 1999-05-04 |
| GB2251248A (en) | 1992-07-01 |
| PL292944A1 (en) | 1992-09-07 |
| IT1252221B (en) | 1995-06-05 |
| NO178897C (en) | 1996-06-26 |
| CZ281616B6 (en) | 1996-11-13 |
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