JPS626532B2 - - Google Patents
Info
- Publication number
- JPS626532B2 JPS626532B2 JP54044954A JP4495479A JPS626532B2 JP S626532 B2 JPS626532 B2 JP S626532B2 JP 54044954 A JP54044954 A JP 54044954A JP 4495479 A JP4495479 A JP 4495479A JP S626532 B2 JPS626532 B2 JP S626532B2
- Authority
- JP
- Japan
- Prior art keywords
- cobalt
- fatty acid
- water
- methanol
- acetic acid
- 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 39
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 30
- 229930195729 fatty acid Natural products 0.000 claims description 30
- 239000000194 fatty acid Substances 0.000 claims description 30
- 229910017052 cobalt Inorganic materials 0.000 claims description 24
- 239000010941 cobalt Substances 0.000 claims description 24
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 17
- 150000004665 fatty acids Chemical class 0.000 claims description 17
- 150000005846 sugar alcohols Polymers 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- -1 fatty acid ester Chemical class 0.000 claims description 13
- 239000007788 liquid Substances 0.000 claims description 10
- 239000007791 liquid phase Substances 0.000 claims description 4
- 238000000605 extraction Methods 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- FDPHDGUADUFPHZ-UHFFFAOYSA-L cobalt(2+);heptanoate Chemical compound [Co+2].CCCCCCC([O-])=O.CCCCCCC([O-])=O FDPHDGUADUFPHZ-UHFFFAOYSA-L 0.000 description 11
- 239000012071 phase Substances 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- 150000001336 alkenes Chemical class 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- NCGQPNAQUYGWMI-UHFFFAOYSA-N [3-heptanoyloxy-2,2-bis(heptanoyloxymethyl)propyl] heptanoate Chemical compound CCCCCCC(=O)OCC(COC(=O)CCCCCC)(COC(=O)CCCCCC)COC(=O)CCCCCC NCGQPNAQUYGWMI-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- UQJDVLPHTXQTRP-UHFFFAOYSA-N 2,2-bis(heptanoyloxymethyl)butyl heptanoate Chemical compound CCCCCCC(=O)OCC(CC)(COC(=O)CCCCCC)COC(=O)CCCCCC UQJDVLPHTXQTRP-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 235000021588 free fatty acids Nutrition 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000004711 α-olefin 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Description
【発明の詳細な説明】
本発明は多価アルコールの脂肪酸エステルおよ
び脂肪酸コバルトを含む混合液から脂肪酸コバル
トを分離する方法に関するものであり、特に本発
明はコバルトカルボニル錯体を触媒とするヒドロ
エステル化反応におけるコバルトの回収方法とし
て工業的に有利に適用される。Detailed Description of the Invention The present invention relates to a method for separating fatty acid cobalt from a mixed liquid containing a fatty acid ester of a polyhydric alcohol and a fatty acid cobalt. In particular, the present invention relates to a hydroesterification reaction using a cobalt carbonyl complex as a catalyst. It is advantageously applied industrially as a method for recovering cobalt.
コバルトカルボニル錯体を触媒とする多価アル
コール、オレフインおよび一酸化炭素のヒドロエ
ステル化反応による多価アルコールの脂肪酸エス
テルの製造法においては、反応生成液からパラフ
インまたはオレフインを用いて多価アルコールの
脂肪酸エステルを抽出することによりコバルトカ
ルボニル錯体を分離する方法が提案されている
（特公昭53−31128、特公昭53−37327）。この方法
の利点は、コバルトを活性種の形態で回収できる
ためにそのまま反応系に循環して使用し得るとこ
ろにあるが、コバルトカルボニル錯体がパラフイ
ンまたはオレフインにある程度溶解することによ
る回収ロスと回収触媒の失活による触媒活性の低
下のために、新触媒の追加と回収触媒の活性化処
理を行なつて収率を一定に維持する必要がある。 In the method for producing fatty acid esters of polyhydric alcohols by the hydroesterification reaction of polyhydric alcohols, olefins and carbon monoxide using a cobalt carbonyl complex as a catalyst, fatty acid esters of polyhydric alcohols are produced using paraffin or olefin from the reaction product liquid. A method has been proposed to separate cobalt carbonyl complexes by extracting them (Japanese Patent Publications No. 53-31128 and No. 53-37327). The advantage of this method is that cobalt can be recovered in the form of active species, so it can be recycled to the reaction system and used as is, but there is a recovery loss due to the cobalt carbonyl complex dissolving to some extent in paraffin or olefin, and recovery catalyst Since the catalyst activity decreases due to the deactivation of the catalyst, it is necessary to maintain the yield constant by adding new catalyst and activating the recovered catalyst.
一般に、前述したヒドロエステル化反応による
多価アルコールの脂肪酸エステルの製造法におい
て得られる反応生成液には、多価アルコールの脂
肪酸エステル、未反応オレフイン、コバルトカル
ボニル錯体、コバルトカルボニル錯体に対して過
剰量のピリジン類塩基配位子、および副反応によ
り生成する原料オレフインよりも炭素原子数が１
個多い脂肪酸が含まれている。この反応生成液を
蒸留して未反応オレフインおよびピリジン類塩基
を留去すれば、コバルトカルボニル錯体はその不
安定性のゆえにすみやかに分解して、共存する遊
離の脂肪酸に捉えられて脂肪酸コバルトに転化
し、多価アルコールの脂肪酸エステルおよび脂肪
酸コバルトを含む混合液が得られる。本発明にお
いては、主として上記のような混合液が対象とな
るが、勿論他の方法で得られる多価アルコールの
脂肪酸エステルおよび脂肪酸コバルトを含む混合
液も対象とすることができる。 In general, the reaction product liquid obtained in the method for producing fatty acid esters of polyhydric alcohols by the hydroesterification reaction described above contains an excess amount of fatty acid esters of polyhydric alcohols, unreacted olefins, cobalt carbonyl complexes, and cobalt carbonyl complexes. The number of carbon atoms is 1 compared to the pyridine base ligand and the raw material olefin produced by the side reaction.
Contains a lot of fatty acids. When this reaction product solution is distilled to remove unreacted olefins and pyridine bases, the cobalt carbonyl complex is quickly decomposed due to its instability and is captured by coexisting free fatty acids and converted into fatty acid cobalt. , a liquid mixture containing fatty acid ester of polyhydric alcohol and fatty acid cobalt is obtained. In the present invention, the above-mentioned mixed liquids are mainly targeted, but, of course, mixed liquids containing fatty acid esters of polyhydric alcohols and fatty acid cobalt obtained by other methods can also be targeted.
本発明において、多価アルコールの脂肪酸エス
テルとはグリセリン、エチレングリコール、トリ
メチロールプロパン、ペンタエリスリトール等の
多価アルコールの炭素原子数４〜31、好ましくは
５〜13の脂肪酸とのモノエステルまたはポリエス
テルであつて、通常はコバルトカルボニル錯体お
よびピリジン類塩基の存在下に前記多価アルコー
ルを炭素原子数３〜30、好ましくは４〜12のオレ
フインおよび一酸化炭素と反応させることにより
得られる。また、脂肪酸コバルトとは炭素原子数
４〜31、好ましくは５〜13の脂肪酸のコバルト塩
であり、通常は前記多価アルコールの脂肪酸エス
テルの酸成分と同一構造を有する脂肪酸のコバル
ト塩である。勿論、前記混合液中には若干のピリ
ジン類塩基あるいは遊離の脂肪酸が含まれていて
もよい。 In the present invention, the fatty acid ester of a polyhydric alcohol is a monoester or polyester of a polyhydric alcohol such as glycerin, ethylene glycol, trimethylolpropane, or pentaerythritol with a fatty acid having 4 to 31 carbon atoms, preferably 5 to 13 carbon atoms. It is usually obtained by reacting the polyhydric alcohol with an olefin having 3 to 30 carbon atoms, preferably 4 to 12 carbon atoms, and carbon monoxide in the presence of a cobalt carbonyl complex and a pyridine base. The fatty acid cobalt is a cobalt salt of a fatty acid having 4 to 31 carbon atoms, preferably 5 to 13 carbon atoms, and usually has the same structure as the acid component of the fatty acid ester of the polyhydric alcohol. Of course, the mixed liquid may contain some pyridine base or free fatty acid.
本発明は、前述した多価アルコールの脂肪酸エ
ステルおよび脂肪酸コバルトを含む混合液に、メ
タノールもしくは酢酸および水を添加して、脂肪
酸コバルトをメタノールもしくは酢酸および水が
形成する液相に抽出することにより達成される。
メタノールまたは酢酸の添加量は混合液中のエス
テルに対して0.5〜10重量倍、好ましくは２〜５
重量倍であり、水の添加量はメタノールまたは酢
酸に対して0.1〜10重量倍、好ましくは0.2〜0.4重
量倍であり、添加時または添加後に、液−液の接
触を良好にするために、５分間〜２時間程度撹拌
することが望ましい。本発明においては、温度、
圧力、雰囲気などの条件は支配的因子ではなく、
常温、常圧下に大気中においても本発明を実施す
ることができる。 The present invention is achieved by adding methanol or acetic acid and water to the above-mentioned mixed liquid containing fatty acid ester of polyhydric alcohol and fatty acid cobalt, and extracting fatty acid cobalt into a liquid phase formed by methanol or acetic acid and water. be done.
The amount of methanol or acetic acid added is 0.5 to 10 times the weight of the ester in the mixture, preferably 2 to 5 times the weight of the ester.
The amount of water added is 0.1 to 10 times the weight of methanol or acetic acid, preferably 0.2 to 0.4 times the weight of methanol or acetic acid. During or after addition, in order to improve liquid-liquid contact, It is desirable to stir for about 5 minutes to 2 hours. In the present invention, temperature,
Conditions such as pressure and atmosphere are not the dominant factors;
The present invention can also be carried out in the atmosphere at normal temperature and pressure.
以上の操作により脂肪酸コバルトはメタノール
もしくは酢酸および水が形成する液相に抽出さ
れ、主に多価アルコールの脂肪酸エステルよりな
る相と分離する。 Through the above operations, fatty acid cobalt is extracted into a liquid phase formed by methanol or acetic acid and water, and separated from a phase mainly consisting of fatty acid esters of polyhydric alcohols.
多価アルコールの脂肪酸エステルは上記した相
から蒸留等の手段により不純物を除去することに
より純度よく得ることができる。一方、脂肪酸コ
バルトはメタノールもしくは酢酸および水が形成
する相より溶媒に留去することにより取得できる
が、通常は、そのままあるいは適当に濃縮したの
ち、ヒドロエステル化反応の触媒原料として使用
される。 The fatty acid ester of polyhydric alcohol can be obtained with high purity by removing impurities from the above-mentioned phase by means such as distillation. On the other hand, fatty acid cobalt can be obtained by distilling off a phase formed by methanol or acetic acid and water into a solvent, but it is usually used as a catalyst raw material for the hydroesterification reaction as it is or after being appropriately concentrated.
次に本発明を実施例により更に具体的に説明す
るが、本発明はその要旨を越えない限り、以下の
実施例に限定されるものではない。 Next, the present invention will be explained in more detail with reference to examples, but the present invention is not limited to the following examples unless it exceeds the gist thereof.
実施例 １
ヘプタン酸コバルト7.19重量％を含有するペン
タエリスリトールテトラヘプタノエート1.99ｇに
メタノール7.81ｇおよび水0.78ｇを添加し、30分
間撹拌したのち30分間静置し、二液相に分離させ
た。各相を分取してそれぞれペンタエリスリトー
ルテトラヘプタノエートおよびヘプタン酸コバル
トについて定量した結果、メタノールおよび水が
形成する相（上層）に、ペンタエリスリトールテ
トラヘプタノエートはその24％が分配し、ヘプタ
ン酸コバルトはその100％が分配していた。Example 1 7.81 g of methanol and 0.78 g of water were added to 1.99 g of pentaerythritol tetraheptanoate containing 7.19% by weight of cobalt heptanoate, stirred for 30 minutes, and then allowed to stand for 30 minutes to separate into two liquid phases. . As a result of separating each phase and quantifying pentaerythritol tetraheptanoate and cobalt heptanoate, it was found that 24% of pentaerythritol tetraheptanoate partitioned into the phase (upper layer) formed by methanol and water, and heptanoate 100% of the acid cobalt was distributed.
実施例 ２
ヘプタン酸コバルト6.25重量％を含有するトリ
メチロールプロパントリヘプタノエート2.01ｇに
メタノール7.28ｇおよび水0.81ｇを添加し、実施
例１と同様の操作を行なつた。その結果、メタノ
ールおよび水が形成する相（上層）に、トリメチ
ロールプロパントリヘプタノエートはその44％が
分配し、ヘプタン酸コバルトはその78％が分配し
ていた。Example 2 7.28 g of methanol and 0.81 g of water were added to 2.01 g of trimethylolpropane triheptanoate containing 6.25% by weight of cobalt heptanoate, and the same operation as in Example 1 was carried out. As a result, 44% of trimethylolpropane triheptanoate and 78% of cobalt heptanoate were distributed in the phase formed by methanol and water (upper layer).
実施例 ３
ヘプタン酸コバルト6.55重量％を含有するペン
タエリスリトールテトラヘプタノエート2.06ｇに
酢酸10.4ｇおよび水3.99ｇを添加し、実施例１と
同様の操作を行なつた。その結果、酢酸および水
が形成する相（下層）に、ペンタエリスリトール
テトラヘプタノエートはその１％が分配し、ヘプ
タン酸コバルトはその87％が分配していた。Example 3 10.4 g of acetic acid and 3.99 g of water were added to 2.06 g of pentaerythritol tetraheptanoate containing 6.55% by weight of cobalt heptanoate, and the same operation as in Example 1 was carried out. As a result, 1% of pentaerythritol tetraheptanoate and 87% of cobalt heptanoate were distributed in the phase formed by acetic acid and water (lower layer).
実施例 ４
ヘプタン酸コバルト6.89重量％を含有するトリ
メチロールプロパントリヘプタノエート2.09ｇに
酢酸10.5ｇおよび水3.97ｇを添加し、実施例１と
同様の操作を行なつた。その結果、酢酸および水
が形成する相（下層）に、トリメチロールプロパ
ントリヘプタノエートはその９％が分配し、ヘプ
タン酸コバルトはその77％が分配していた。Example 4 10.5 g of acetic acid and 3.97 g of water were added to 2.09 g of trimethylolpropane triheptanoate containing 6.89% by weight of cobalt heptanoate, and the same operation as in Example 1 was carried out. As a result, 9% of trimethylolpropane triheptanoate and 77% of cobalt heptanoate were distributed in the phase formed by acetic acid and water (lower layer).
実施例 ５
ヘプタン酸コバルト4.2重量％および炭素原子
数20〜28のα−オレフイン混合物28.5重量％を含
有するエチレングリコールと炭素原子数21〜29の
脂肪酸のジエステル2.0ｇに酢酸1.0ｇおよび水10
ｇを添加し、80℃で30分間撹拌したのち冷却して
析出した固体を別した。水溶液相中に含有され
るヘプタン酸コバルトを定量したところ、ヘプタ
ン酸コバルトの回収率は99％であつた。Example 5 2.0 g of a diester of ethylene glycol and C21-29 fatty acids containing 4.2% by weight of cobalt heptanoate and 28.5% by weight of a mixture of C20-28 alpha-olefins, 1.0 g of acetic acid and 10 g of water
After stirring at 80°C for 30 minutes, the mixture was cooled and the precipitated solid was separated. When the cobalt heptanoate contained in the aqueous solution phase was quantified, the recovery rate of cobalt heptanoate was 99%.
Claims (1)
酸コバルトを含む混合液にメタノールもしくは酢
酸および水を添加して、脂肪酸コバルトをメタノ
ールもしくは酢酸および水が形成する液相に抽出
することを特徴とする脂肪酸コバルトの抽出分離
法。1 Extraction of fatty acid cobalt, characterized by adding methanol or acetic acid and water to a mixed liquid containing a fatty acid ester of a polyhydric alcohol and fatty acid cobalt, and extracting fatty acid cobalt into a liquid phase formed by methanol or acetic acid and water. Separation method.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4495479A JPS55139334A (en) | 1979-04-13 | 1979-04-13 | Extractive separation of cobalt salt of fatty acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4495479A JPS55139334A (en) | 1979-04-13 | 1979-04-13 | Extractive separation of cobalt salt of fatty acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55139334A JPS55139334A (en) | 1980-10-31 |
| JPS626532B2 true JPS626532B2 (en) | 1987-02-12 |
Family
ID=12705871
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4495479A Granted JPS55139334A (en) | 1979-04-13 | 1979-04-13 | Extractive separation of cobalt salt of fatty acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS55139334A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6420529U (en) * | 1987-07-27 | 1989-02-01 |
-
1979
- 1979-04-13 JP JP4495479A patent/JPS55139334A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6420529U (en) * | 1987-07-27 | 1989-02-01 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS55139334A (en) | 1980-10-31 |
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