JPH11158196A - Extraction of tall oil alcohol component contained in tall oil skimming - Google Patents
Extraction of tall oil alcohol component contained in tall oil skimmingInfo
- Publication number
- JPH11158196A JPH11158196A JP34051797A JP34051797A JPH11158196A JP H11158196 A JPH11158196 A JP H11158196A JP 34051797 A JP34051797 A JP 34051797A JP 34051797 A JP34051797 A JP 34051797A JP H11158196 A JPH11158196 A JP H11158196A
- Authority
- JP
- Japan
- Prior art keywords
- tall oil
- extraction
- alcohol component
- skimming
- solvent
- 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.)
- Pending
Links
- 239000003784 tall oil Substances 0.000 title claims abstract description 78
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 238000000605 extraction Methods 0.000 title description 37
- 239000007864 aqueous solution Substances 0.000 claims abstract description 16
- 239000007787 solid Substances 0.000 claims abstract description 11
- 239000005456 alcohol based solvent Substances 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 239000002904 solvent Substances 0.000 abstract description 28
- 238000000034 method Methods 0.000 abstract description 11
- 238000011084 recovery Methods 0.000 abstract description 4
- 238000000926 separation method Methods 0.000 abstract description 4
- 239000000243 solution Substances 0.000 abstract description 3
- 239000005453 ketone based solvent Substances 0.000 abstract description 2
- 239000010410 layer Substances 0.000 description 17
- 239000012044 organic layer Substances 0.000 description 13
- 239000003960 organic solvent Substances 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 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 5
- 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 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 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 5
- 229930182558 Sterol Natural products 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 150000003432 sterols Chemical class 0.000 description 4
- 235000003702 sterols Nutrition 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- -1 diterpene alcohols Chemical class 0.000 description 3
- 239000000344 soap Substances 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229930004069 diterpene Natural products 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- NMRPBPVERJPACX-UHFFFAOYSA-N (3S)-octan-3-ol Natural products CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- WOFPPJOZXUTRAU-UHFFFAOYSA-N 2-Ethyl-1-hexanol Natural products CCCCC(O)CCC WOFPPJOZXUTRAU-UHFFFAOYSA-N 0.000 description 1
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 1
- VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-Methylcyclohexanone Natural products CC1CCC(=O)CC1 VGVHNLRUAMRIEW-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- AEMFNILZOJDQLW-QAGGRKNESA-N androst-4-ene-3,17-dione Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 AEMFNILZOJDQLW-QAGGRKNESA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- MQWCXKGKQLNYQG-UHFFFAOYSA-N methyl cyclohexan-4-ol Natural products CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- 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
- Compounds Of Unknown Constitution (AREA)
- Fats And Perfumes (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明はトール油スキミング
から、ステロール類、ジテルペンアルコール類、直鎖ア
ルコールなどのアルコール成分（以下、トール油アルコ
ール成分という）を抽出する方法に関する。抽出された
トール油アルコール成分は医薬原料、工業原料として有
用である。The present invention relates to a method for extracting alcohol components such as sterols, diterpene alcohols and straight-chain alcohols (hereinafter referred to as tall oil alcohol components) from tall oil skimming. The extracted tall oil alcohol component is useful as a pharmaceutical raw material and an industrial raw material.
【０００２】[0002]
【従来の技術】粗製トール油の原料であるトール油スキ
ミングは、脂肪酸やロジンのナトリウム塩（以下、トー
ル油石鹸という）を主成分として含有する他、ステロー
ル類、ジテルペンアルコール類、直鎖アルコール類など
のトール油アルコール成分を含む。2. Description of the Related Art Tall oil skimming, which is a raw material of crude tall oil, contains fatty acids and sodium salts of rosin (hereinafter referred to as tall oil soap) as main components, sterols, diterpene alcohols, and straight-chain alcohols. Including tall oil alcohol components.
【０００３】トール油スキミングから、これらのトール
油アルコール成分を抽出する方法としては、トール油ア
ルコール成分が油溶性であり、トール油石鹸が水溶性で
あることを利用して、トール油スキミングを水−水溶性
有機溶媒に溶解した後、溶媒抽出する方法が一般的であ
る。たとえば、トール油スキミングを含水イソプロパノ
ールに溶解した後、ベンゼンで抽出する方法（米国特許
明細書2530809号）、トール油スキミングを含水アセト
ンに溶解した後、ヘキサンで抽出する方法（米国特許明
細書3965085号）等が知られている。[0003] As a method for extracting these tall oil alcohol components from tall oil skimming, tall oil skimming is carried out using water, utilizing the fact that the tall oil alcohol component is oil-soluble and the tall oil soap is water-soluble. -A method of dissolving in a water-soluble organic solvent followed by solvent extraction is common. For example, a method of dissolving tall oil skimming in hydrated isopropanol and extracting with benzene (US Pat. No. 2530809), and a method of dissolving tall oil skimming in hydrated acetone and extracting with hexane (US Pat. No. 3965085) ) Etc. are known.
【０００４】しかし、これらの方法により、トール油ア
ルコール成分を効率よく抽出するには多量の低級アルコ
ール類などの水溶性有機溶媒を使用しなければならな
い。また、水層中には水溶性有機溶媒の他に抽出溶媒が
存在するため、水溶性有機溶媒を回収使用するためには
精密分留が必要である。このように、従来行われている
一般的なトール油アルコール成分の抽出方法では、水溶
性有機溶媒の使用が必須とされるため、その回収、分離
の点に問題があり、また水溶性有機溶媒の引火点が低い
ことなどから、工業的に実施するには著しい不利があ
る。However, in order to efficiently extract the tall oil alcohol component by these methods, a large amount of a water-soluble organic solvent such as a lower alcohol must be used. In addition, since the aqueous layer contains an extraction solvent in addition to the water-soluble organic solvent, precise fractionation is required to recover and use the water-soluble organic solvent. As described above, since the conventional method of extracting a tall oil alcohol component generally requires the use of a water-soluble organic solvent, there is a problem in its recovery and separation, and the water-soluble organic solvent Because of its low flash point, there is a significant disadvantage for industrial implementation.
【０００５】こうした水−水溶性有機溶媒と抽出溶媒を
使用することによる問題を解決するため、水−水溶性有
機溶媒にトール油スキミングを溶解する代わりに、水に
トール油スキミングを溶解した後に、ベンゼン、ヘキサ
ン等で溶媒抽出することが考えられる。しかし、この場
合には強い乳化が起こるため有機層と水層を分離するこ
とができない。また、トール油スキミングを水で希釈し
た後、酢酸エチルなどの低級脂肪族エステル類を抽出溶
媒として用いる方法が提案されている（米国特許明細書
2866781号）。しかしながら、上記エステル類が、トー
ル油スキミング中に多量に含まれる水酸化ナトリウムに
より加水分解されるため、抽出溶媒として用いるエステ
ル類の回収率が低いという問題があり、工業的には実施
し難い。In order to solve the problems caused by using such a water-water-soluble organic solvent and an extraction solvent, instead of dissolving tall oil skimming in water-water-soluble organic solvent, after dissolving tall oil skimming in water, Solvent extraction with benzene, hexane, or the like can be considered. However, in this case, the organic layer and the aqueous layer cannot be separated because strong emulsification occurs. Further, a method has been proposed in which tall oil skimming is diluted with water, and a lower aliphatic ester such as ethyl acetate is used as an extraction solvent (US Patent Specification).
No. 2866781). However, since the esters are hydrolyzed by sodium hydroxide contained in a large amount during the tall oil skimming, there is a problem that the recovery rate of the esters used as the extraction solvent is low, and it is difficult to implement industrially.
【０００６】[0006]
【発明が解決しようとする課題】本発明は、抽出溶媒の
回収、分離が容易で、しかもトール油スキミングからト
ール油アルコール成分を効率よく抽出する方法を提供す
ることを目的とする。SUMMARY OF THE INVENTION An object of the present invention is to provide a method for easily extracting and extracting an extraction solvent and efficiently extracting a tall oil alcohol component from tall oil skimming.
【０００７】[0007]
【課題を解決するための手段】本発明者らは、前記課題
を解決すべく鋭意検討を重ねた結果、トール油スキミン
グをその固形分濃度が４０重量％以下になるように調製
した水溶液に、トール油アルコール成分の抽出溶媒とし
て、炭素数４〜１２のアルコール系溶媒および／または
炭素数４〜１２のケトン系溶媒を用いることより前記課
題を解決できることを見出し、本発明を解決するに到っ
た。Means for Solving the Problems The inventors of the present invention have conducted intensive studies to solve the above-mentioned problems, and as a result, have found that tall oil skimming can be carried out in an aqueous solution prepared so that its solid content concentration is 40% by weight or less. The present inventors have found that the above problem can be solved by using an alcoholic solvent having 4 to 12 carbon atoms and / or a ketone solvent having 4 to 12 carbon atoms as an extraction solvent for the tall oil alcohol component. Was.
【０００８】すなわち本発明は、トール油スキミングの
固形分濃度が４０重量％以下になるように調製した水溶
液に、炭素数４〜１２のアルコール系溶媒および／また
は炭素数４〜１２のケトン系溶媒を加え、当該水溶液か
らトール油スキミングに含まれるトール油アルコール成
分を抽出することを特徴とするトール油スキミングに含
まれるトール油アルコール成分の抽出方法に関する。That is, the present invention relates to an aqueous solvent prepared so that the solid content of tall oil skimming is 40% by weight or less, an alcoholic solvent having 4 to 12 carbon atoms and / or a ketone solvent having 4 to 12 carbon atoms. And extracting the tall oil alcohol component contained in the tall oil skimming from the aqueous solution.
【０００９】[0009]
【発明の実施の形態】本発明で用いるトール油スキミン
グは、硫酸塩パルプやソーダパルプの製造廃液の上層に
浮かぶ黒褐色のクリーム状物であり、粗製トール油の原
料となるものである。本発明では、まず、かかるトール
油スキミングに、必要に応じて水を加え、または濃縮し
て、固形分濃度が４０重量％以下の水溶液を調製する。
固形分濃度が４０重量％を超える場合には、本発明の抽
出方法に用いる抽出溶媒を加え撹拌後静置しても有機層
と水層が分離しなかったり分離したとしても有機層に濁
りを生ずる。効率的にトール油アルコール成分の抽出を
行なうには、当該水溶液の固形分濃度を１５重量％以上
に調製するのが好ましい。BEST MODE FOR CARRYING OUT THE INVENTION Tall oil skimming used in the present invention is a black-brown creamy substance floating in the upper layer of a waste liquor for sulfate pulp or soda pulp, and is used as a raw material for crude tall oil. In the present invention, first, water is added or concentrated as necessary to the tall oil skimming to prepare an aqueous solution having a solid concentration of 40% by weight or less.
When the solid content concentration exceeds 40% by weight, the organic solvent and the aqueous layer are not separated even if the extraction solvent used in the extraction method of the present invention is added and stirred and then allowed to stand still. Occurs. In order to efficiently extract the tall oil alcohol component, it is preferable to adjust the solid concentration of the aqueous solution to 15% by weight or more.
【００１０】次いで、上記トール油スキミングを含む所
定濃度以下の水溶液に、抽出溶媒として炭素数４〜１２
のアルコール系溶媒および／または炭素数４〜１２のケ
トン系溶媒を加え、当該水溶液からトール油スキミング
に含まれるトール油アルコール成分を抽出する。炭素数
が３以下のアルコール系溶媒やケトン系溶媒は、水溶性
であるため抽出溶媒として使用できない。Next, an aqueous solution containing the above-mentioned tall oil skimming and having a concentration of not more than a predetermined concentration is added as an extraction solvent to a solution having 4 to 12 carbon atoms.
And / or a ketone solvent having 4 to 12 carbon atoms is added, and the tall oil alcohol component contained in the tall oil skimming is extracted from the aqueous solution. Alcohol solvents and ketone solvents having 3 or less carbon atoms cannot be used as extraction solvents because they are water-soluble.
【００１１】炭素数４〜１２のアルコール系溶媒として
は、たとえば、１−ブタノール、２−ブタノール、１−
ヘキサノール、シクロヘキサノール、１−オクタノー
ル、２−エチル−１−ヘキサノールなどをあげることが
できる。また、炭素数４〜１２のケトン系溶媒として
は、たとえば、２−ブタノン、４−メチル−２−ペンタ
ノン、シクロヘキサノン、２−オクタノンなどをあげる
ことができる。Examples of the alcohol solvent having 4 to 12 carbon atoms include 1-butanol, 2-butanol and 1-butanol.
Hexanol, cyclohexanol, 1-octanol, 2-ethyl-1-hexanol and the like can be mentioned. In addition, examples of the ketone solvent having 4 to 12 carbon atoms include 2-butanone, 4-methyl-2-pentanone, cyclohexanone, and 2-octanone.
【００１２】抽出溶媒の使用量は特に制限されないが、
１回の抽出につき、トール油スキミングを含む水溶液に
対し、通常、２０〜５００重量％程度を用いる。２０重
量％に満たない場合には、抽出溶媒の種類によっては有
機層と水層とが分離しにくい場合がある。一方、５００
重量％を超えて使用しても抽出量は変わらず、むしろ少
量の抽出溶媒を数回に分けて使用する方の抽出効率が高
い。Although the amount of the extraction solvent is not particularly limited,
For one extraction, about 20 to 500% by weight is usually used based on the aqueous solution containing tall oil skimming. If the amount is less than 20% by weight, the organic layer and the aqueous layer may not be easily separated depending on the type of the extraction solvent. On the other hand, 500
The amount of extraction does not change even if it is used in excess of wt%, but rather the extraction efficiency is higher when a small amount of extraction solvent is used in several portions.
【００１３】具体的な、抽出方法としては、たとえば、
上記トール油スキミングを含む所定濃度以下のトール油
スキミングに前記抽出溶媒を加え激しく撹拌した後に静
置し、分離した有機層と水層を分離する方法があげられ
る。抽出温度は通常室温で行うが、抽出溶媒の種類によ
っては最も抽出効率のよい温度で抽出を行うことができ
る。As a specific extraction method, for example,
There is a method in which the above-mentioned extraction solvent is added to tall oil skimming having a predetermined concentration or less including the above-described tall oil skimming, the mixture is vigorously stirred, and the mixture is allowed to stand to separate the separated organic layer and aqueous layer. The extraction is usually performed at room temperature, but depending on the type of extraction solvent, the extraction can be performed at a temperature at which the extraction efficiency is highest.
【００１４】分離した有機層（抽出溶媒層）にはトール
油アルコール成分が含まれている。有機層中のトール油
アルコール成分は、抽出溶媒を留去することにより得ら
れる。トール油アルコール成分の抽出量は、トール油ス
キミングの水溶液の固形分に対し通常５〜１５重量％程
度である。また、本発明の抽出方法に使用した抽出溶媒
は、その殆ど全てを有機層から回収できる。The separated organic layer (extraction solvent layer) contains a tall oil alcohol component. The tall oil alcohol component in the organic layer is obtained by distilling off the extraction solvent. The extraction amount of the tall oil alcohol component is usually about 5 to 15% by weight based on the solid content of the aqueous solution of tall oil skimming. Almost all of the extraction solvent used in the extraction method of the present invention can be recovered from the organic layer.
【００１５】一方、水層にはトール油石鹸が含まれてい
る。なお、１回の抽出では、水層中に抽出されなかった
トール油アルコール成分が含まれている場合があるので
同様の抽出操作を複数回繰り返して行なうこともでき
る。こうして分離された水層にはトール油アルコール成
分を殆ど含まない。On the other hand, the water layer contains tall oil soap. In addition, in one extraction, since the unextracted tall oil alcohol component may be contained in the aqueous layer, the same extraction operation can be repeated several times. The aqueous layer thus separated contains almost no tall oil alcohol component.
【００１６】[0016]
【発明の効果】本発明の抽出方法によれば、トール油ス
キミングからトール油アルコール成分を効率的に抽出で
き、しかも抽出溶媒の回収、分離が容易である。また、
抽出処理されたトール油スキミング中には、トール油ア
ルコール成分が殆どないため、粗製トール油の貯蔵時お
よび蒸留時に、蒸留残査になるいわゆるトール油ピッチ
（トール油アルコール成分と脂肪酸やロジンとのエステ
ル化物）が殆ど生じない。そのため、抽出処理されたト
ール油スキミングから得られる粗製トール油は、トール
油ロジン、トール油脂肪酸の蒸留収率が高く、非常に酸
価の高い高品質なものである。According to the extraction method of the present invention, the tall oil alcohol component can be efficiently extracted from the tall oil skimming, and the recovery and separation of the extraction solvent are easy. Also,
During the extraction-treated tall oil skimming, since there is almost no tall oil alcohol component, so-called tall oil pitch (a mixture of the tall oil alcohol component with fatty acids and rosin) becomes a distillation residue during storage and distillation of crude tall oil. Almost no esterified product). Therefore, the crude tall oil obtained from the extracted tall oil skimming has a high distillation yield of tall oil rosin and tall oil fatty acid, and has high acid value and high quality.
【００１７】[0017]
【実施例】以下に実施例および比較例をあげて本発明を
さらに詳細に説明するが、本発明はこれら実施例に限定
されるものではない。The present invention will be described in more detail with reference to examples and comparative examples, but the present invention is not limited to these examples.
【００１８】実施例１〜８、比較例１〜３ トール油スキミングに水を加え、表１に示すような固形
分濃度のトール油スキミングの水溶液を調製した。な
お、固形分濃度はトール油スキミングの水溶液の一部
を、１０５℃で４時間乾燥させ、その乾燥重量を測定し
て求めた。当該水溶液１０００ｇに対し、表１に示す抽
出溶媒１０００ｇを加え、室温で１０分間激しく撹拌し
た後、分液ロートに移し３０分間静置した。水層と有機
層の分離状態を表１に示す。水層と有機層を分離可能な
ものについては有機層を分離し、水層についてはさらに
２回同様の操作を行った。これらの有機層をあわせた
後、抽出溶媒を除去しトール油アルコール成分を得た。
トール油アルコール成分の抽出量、トール油スキミング
の水溶液の固形分に対する抽出率、トール油アルコール
成分の水酸基価およびトール油アルコール成分中のステ
ロール類の含有率を表２に示す。Examples 1 to 8 and Comparative Examples 1 to 3 Water was added to tall oil skimming to prepare an aqueous solution of tall oil skimming having a solid content as shown in Table 1. The solids content was determined by drying a part of the aqueous solution of tall oil skimming at 105 ° C. for 4 hours and measuring the dry weight. To 1,000 g of the aqueous solution, 1000 g of the extraction solvent shown in Table 1 was added, and the mixture was vigorously stirred at room temperature for 10 minutes, and then transferred to a separating funnel and allowed to stand for 30 minutes. Table 1 shows the separation state of the aqueous layer and the organic layer. The organic layer was separated if the aqueous layer and the organic layer could be separated, and the same operation was further performed twice on the aqueous layer. After combining these organic layers, the extraction solvent was removed to obtain a tall oil alcohol component.
Table 2 shows the extraction amount of the tall oil alcohol component, the extraction ratio of the tall oil skimming solution with respect to the solid content of the aqueous solution, the hydroxyl value of the tall oil alcohol component, and the content of sterols in the tall oil alcohol component.
【００１９】[0019]
【表１】 [Table 1]
【００２０】なお、比較例２〜４では水層と有機相に分
離せず均一相となり茶褐色の沈殿を生じた。比較例５、
６では水層、有機層ともに激しく乳化し水層と有機層が
分離しなかった。In Comparative Examples 2 to 4, the aqueous phase and the organic phase were not separated but became a homogeneous phase, and a brownish precipitate was produced. Comparative Example 5,
In No. 6, both the aqueous layer and the organic layer were vigorously emulsified, and the aqueous layer and the organic layer were not separated.
【００２１】[0021]
【表２】 [Table 2]
【００２２】トール油アルコール成分中のステロール類
の含有率は、得られたトール油アルコールをテトラヒド
ロフラン−メタノール混合溶媒に溶解し、内部標準物質
としてデルタ−４−アンドロステン−３、１７−ジオン
（東京化成、純度９９．５％）を用いガスクロマトグラ
フィー分析により行なった。キャピラリーカラム：ＳＣ
Ａ−５（スペルコ社製）。液相厚 ２５ミクロン、内径
０．２５ｍｍ×３０ｍ。The content of sterols in the tall oil alcohol component can be determined by dissolving the obtained tall oil alcohol in a mixed solvent of tetrahydrofuran and methanol and using delta-4-androstene-3,17-dione (Tokyo) as an internal standard substance. (Purity: 99.5%). Capillary column: SC
A-5 (manufactured by Spelco). Liquid phase thickness 25 microns, inner diameter 0.25 mm x 30 m.
【００２３】実施例１〜８において有機層から分離した
水層には硫酸を加えてｐＨ３に調製した後、トルエンを
加えた。トルエン層を濃縮して得られたもの（改質粗製
トール油）について、ロジン含有率（Ｒ：重量％）、脂
肪酸含有率（Ｆ：重量％）および不けん化物含有率
（Ｕ：重量％）をＡＳＴＭ Ｄ−８０３の方法により測
定した。結果を表３に示す。The aqueous layer separated from the organic layer in Examples 1 to 8 was adjusted to pH 3 by adding sulfuric acid, and then toluene was added. For the product obtained by concentrating the toluene layer (modified crude tall oil), the rosin content (R: wt%), fatty acid content (F: wt%) and unsaponifiable matter content (U: wt%) Was measured by the method of ASTM D-803. Table 3 shows the results.
【００２４】[0024]
【表３】 [Table 3]
【００２５】なお、抽出処理を施していないトール油ス
キミングから得られた粗製トール油のロジン含有率は４
０．２重量％、脂肪酸含有率は５１．０重量％および不
けん化物含有率は８．８重量％であった。The rosin content of the crude tall oil obtained from unextracted tall oil skimming was 4%.
0.2% by weight, fatty acid content was 51.0% by weight and unsaponifiable matter content was 8.8% by weight.
Claims (1)
重量％以下になるように調製した水溶液に、炭素数４〜
１２のアルコール系溶媒および／または炭素数４〜１２
のケトン系溶媒を加え、当該水溶液からトール油スキミ
ングに含まれるトール油アルコール成分を抽出すること
を特徴とするトール油スキミングに含まれるトール油ア
ルコール成分の抽出方法。The tall oil skimming has a solid concentration of 40.
Aqueous solution prepared so as to be less than 4% by weight
12 alcohol solvents and / or 4 to 12 carbon atoms
And extracting a tall oil alcohol component contained in the tall oil skimming from the aqueous solution.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP34051797A JPH11158196A (en) | 1997-11-25 | 1997-11-25 | Extraction of tall oil alcohol component contained in tall oil skimming |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP34051797A JPH11158196A (en) | 1997-11-25 | 1997-11-25 | Extraction of tall oil alcohol component contained in tall oil skimming |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH11158196A true JPH11158196A (en) | 1999-06-15 |
Family
ID=18337744
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP34051797A Pending JPH11158196A (en) | 1997-11-25 | 1997-11-25 | Extraction of tall oil alcohol component contained in tall oil skimming |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH11158196A (en) |
-
1997
- 1997-11-25 JP JP34051797A patent/JPH11158196A/en active Pending
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