JP2021527115A - 植物油からバイオ潤滑油を得るプロセス及びバイオ潤滑油 - Google Patents
植物油からバイオ潤滑油を得るプロセス及びバイオ潤滑油 Download PDFInfo
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- JP2021527115A JP2021527115A JP2021517882A JP2021517882A JP2021527115A JP 2021527115 A JP2021527115 A JP 2021527115A JP 2021517882 A JP2021517882 A JP 2021517882A JP 2021517882 A JP2021517882 A JP 2021517882A JP 2021527115 A JP2021527115 A JP 2021527115A
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- Prior art keywords
- oil
- product
- biolubricating
- vegetable oil
- catalyst
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- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 1
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
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- C10M177/00—Special methods of preparation of lubricating compositions; Chemical modification by after-treatment of components or of the whole of a lubricating composition, not covered by other classes
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/31—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of functional groups containing oxygen only in singly bound form
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- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
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Abstract
本発明は、植物油からバイオ潤滑油を得るプロセスであって、(a)分岐脂肪族アルコールを用いて、植物油加水分解の生成物をエステル化反応させる工程と、(b)工程(a)で得られたエステルをエポキシ化反応させる工程と、(c)分岐脂肪族アルコールを用いて、工程(b)で得られたエポキシ化エステルを求核置換反応させる工程とを含むプロセスを説明する。また、本発明は、本プロセスから得られるバイオ潤滑油も説明する。より具体的には、バイオ潤滑油は、本発明の図1に示す式(式中、R1がヒドロキシルであるか又は式R3COO−に基づき、ここでR3がC1−C3のアルキル基、好適にはメチル基であり、R2がC4−C8の炭化水素の直鎖とC1−C3の炭化水素の分岐鎖とからなる)をもつリシノール脂肪酸から生成されるものとして説明される。
Description
(式中、R1がヒドロキシルであるか又は式R3COO−に基づき、ここでR3がC1−C3のアルキル基であり、R2がC4−C8の炭化水素の直鎖とC1−C3の炭化水素の分岐鎖とからなる)からの化合物の混合物を備える。
実施例1‐工程(a)
ヒマシ油の加水分解で得られた脂肪酸を用いて、工程(a)からの反応を実現した。エステル化反応では、アルコールである2−エチルヘキサノールを使用した。このために、脂肪酸の試料を計量して(60g)、500−mL容器へと移した。初期物質の計量した質量から、各モル比及び使用される触媒の質量(3gのAmberlyst−15)に対する、アルコールの体積を計算した(130mL)。
工程(a)での反応から得られたエステルをエポキシ化した。エポキシ化は、原位置で生成された過ギ酸を用いて実現した。反応を開始させるために、70gのエステル(リシノール酸塩)を計量して、500−mL容器へと移した。本システムを、800rpm〜1200rpmの範囲内で撹拌した。次に、ギ酸を反応媒体に追加して(6mL)、その後過酸化水素を追加した(46mL)。反応を、20℃〜40℃の温度で8時間〜24時間観測した。反応混合物を分液漏斗へと移した。相の分離後、有機相(上澄み)を重炭酸ナトリウム5%の溶液で中和して、蒸留水で洗浄した。40分〜80分の間40℃〜80℃であるクーゲルロール装置を用いて、生成物を、まだ存在するギ酸及び過酸化水素を除去するように蒸留した。プロトン核磁気共鳴から得られた転換は95%〜99%であり、質量収率は95%よりも高かった。
まず、エポキシ化したリシノール酸塩の試料を計量して(60g)、還流システム内に接続された容器へと移し、800rpm〜1200rpmで一定して撹拌した。本プロセスの間、本システムを、N2の不活性雰囲気によって継続して加圧した。2−エチルヘキサノールアルコールの体積(67mL)を計測して、アルコールを、触媒であるp−トルエンスルホン酸(6g)を含む500−mL受容器へと移して、完全に溶解させた。混合物を、ゆっくりと反応媒体に追加した。反応を2時間〜6時間観測して、反応の終了後、反応混合物を分液漏斗へと移した。相の分離後、有機相(上澄み)を300mLの重炭酸ナトリウム5%の溶液で中和して、150mLの蒸留水で洗浄した。40分〜80分の間80℃〜100℃の温度であるクーゲルロール装置を用いて、生成物を、余分なアルコールを除去するように蒸留した。プロトン核磁気共鳴から得られた転換は95%〜99%であり、質量収率は90%よりも高かった。
工程(c)で得られた生成物の構造内に存在するヒドロキシルを転換する工程において、酢酸無水物を使用した。
試験は、分岐2−エチルヘキサノールアルコールの、他の直鎖及び循環アルコールと比較して優れた効率性を明示するように、本発明に記載のプロセスの工程(c)における異なるアルコールの効果を比較して、実行された。異なるアルコールによってオキシラン環を開環したことによる反応の後の生成物の物理的性質及び化学的性質の結果を、表1に示す。
Claims (18)
- 植物油からバイオ潤滑油を得るプロセスであって、以下の、
(a)分岐脂肪族アルコールを用いて、前記植物油の加水分解の生成物をエステル化反応させる工程と、
(b)前記工程(a)で得られたエステルをエポキシ化反応させる工程と、
(c)分岐脂肪族アルコールを用いて、前記工程(b)で得られたエポキシ化エステルを求核置換反応させる工程とを含むプロセス。 - 前記工程(a)及び/又は(c)のいずれか一方において用いられる分岐脂肪族アルコールが、C4−C8の炭化水素の直鎖とC1−C3の炭化水素の分岐鎖とからなる、請求項1に記載のプロセス。
- 前記工程(a)及び/又は(c)において用いられる分岐脂肪族アルコールが、2−エチルヘキサノールである、請求項2に記載のプロセス。
- 前記植物油がヒマシ油であり、その加水分解の前記生成物がリシノール脂肪酸である、請求項1に記載のプロセス。
- 植物油加水分解の前記生成物に対して、前記工程(a)でのエステル化反応よりも前に、精製プロセスが行われる、請求項1に記載のプロセス。
- 前記工程(a)で、触媒として、80℃〜100℃の温度範囲で4時間〜8時間の間、ポリスチレン系イオン交換スルホン樹脂が使用され、触媒/植物油の質量比が2.5%と7.5%との間で変わるものが使用され、脂肪酸/アルコールのモル比が1:2と1:4との間で変わるものが使用される、請求項1〜5のいずれか1項に記載のプロセス。
- 前記工程(a)に続いて、以下の、
(a1)前記工程(a)で得られた前記生成物を周囲温度まで冷却する工程と、
(a2)触媒を除去するために、冷却した前記生成物をろ過する工程と、
(a3)余分なアルコールを除去するために、ろ過した前記生成物を蒸留する工程との、1つ又は複数の追加の工程を含む、請求項1〜6のいずれか1項に記載のプロセス。 - 前記工程(b)で、20℃〜40℃の温度範囲で8時間〜24時間の間、ギ酸と過酸化水素とが使用され、エステル/ギ酸/過酸化水素のモル比が1:1:2と1:2:6との間で変わるものが使用される、請求項1〜7のいずれか1項に記載のプロセス。
- 前記工程(a)に続いて、以下の、
(b1)前記工程(b)で得られた前記生成物のデカンテーションによって相を分離させる工程と、
(b2)塩によって有機相を中和させ、続いて洗浄する工程と、
(b3)余分なギ酸及び未反応の過酸化水素を除去するために、中和され洗浄された前記生成物を蒸留する工程との、1つ又は複数の追加の工程を含む、請求項1〜8のいずれか1項に記載のプロセス。 - 前記工程(c)で、触媒として、80℃〜100℃の温度範囲で2時間〜6時間の間、p−トルエンスルホン酸が使用され、触媒/植物油の質量比が5%と15%との間で変わるものが使用され、脂肪酸/アルコールのモル比が1:2と1:4との間で変わるものが使用される、請求項1〜9のいずれか1項に記載のプロセス。
- 前記工程(c)に続いて、以下の、
(c1)前記工程(c)で得られた前記生成物のデカンテーションによって相を分離させる工程と、
(c2)塩によって有機相を中和させ、続いて洗浄する工程と、
(c3)余分なアルコールを除去するために、中和され洗浄された前記生成物を蒸留する工程との、追加の工程を含む、請求項1〜10のいずれか1項に記載のプロセス。 - 前記工程(c)で得られた反応生成物とカルボン酸無水物との反応の工程(d)を含む、請求項1〜11のいずれか1項に記載のプロセス。
- 前記工程(d)が、触媒としての水酸化カリウムと、酢酸、プロパン酸及びブタン酸無水物から選ばれるカルボン酸無水物とを、80℃〜100℃の温度範囲で10時間〜14時間の間使用し、触媒/エステルの質量比が1%と5%との間で変わるものを使用し、エステル/酢酸無水物のモル比が1:1と1:2との間で変わるものを使用して行われる、請求項12に記載のプロセス。
- 前記工程(d)に続いて、以下の、
(d1)前記工程(d)で得られた前記生成物を有機溶媒で希釈する工程と、
(d2)pHを5〜6に調整して、続いて洗浄する工程と、
(d3)前記(d2)で得られた前記生成物を乾燥させる工程と、
(d4)余分な無水物を除去するために、乾燥後の前記生成物を蒸留する工程との、1つ又は複数の追加の工程を含む、請求項12又は13に記載のプロセス。 - 植物油加水分解の生成物から生成されるバイオ潤滑油であって、請求項1〜14のいずれか1項に記載のプロセスから得られるバイオ潤滑油。
- 前記バイオ潤滑油を得る前記プロセスに工程(d)がない場合、R1がヒドロキシルである、請求項16に記載のバイオ潤滑油。
- 120よりも高く、好適には120〜150である粘度指数(VI)と、−40℃よりも低く、好適には−40℃〜−50℃である流動温度と、30分〜60分である酸化安定性とを示す、請求項16又は17に記載のバイオ潤滑油。
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Publication number | Priority date | Publication date | Assignee | Title |
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WO2016020941A2 (en) * | 2014-08-06 | 2016-02-11 | Council Of Scientific & Industrial Research | Preparation of functionalized castor oil derivatives using solid acid and base catalysts |
Non-Patent Citations (3)
Title |
---|
CATALYSIS TODAY, vol. 279, JPN6023015530, 2017, pages 274 - 285, ISSN: 0005045490 * |
JAOCS, vol. 80(8), JPN6023015528, 2006, pages 811 - 815, ISSN: 0005045491 * |
JAOCS, vol. 83(11), JPN6023015529, 2006, pages 959 - 963, ISSN: 0005045489 * |
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