JP2022518941A - ポリオールエステルおよび生物源脂肪酸から合成された潤滑基油 - Google Patents
ポリオールエステルおよび生物源脂肪酸から合成された潤滑基油 Download PDFInfo
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- JP2022518941A JP2022518941A JP2021544231A JP2021544231A JP2022518941A JP 2022518941 A JP2022518941 A JP 2022518941A JP 2021544231 A JP2021544231 A JP 2021544231A JP 2021544231 A JP2021544231 A JP 2021544231A JP 2022518941 A JP2022518941 A JP 2022518941A
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/32—Esters
- C10M105/34—Esters of monocarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/32—Esters
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Abstract
Description
ηは、Pa・s単位の動的粘度であり、
ρは、kg/m3単位の流体の密度である。
本発明によるエステルは、少なくとも1つのポリオールと、少なくとも1つのC5-C12飽和脂肪酸および少なくとも1つのC10-C12不飽和脂肪酸を含む脂肪酸の混合物とから形成される。
好ましくは、本発明によるエステル化方法は、少なくとも1つの本発明によるC5-C12飽和脂肪酸および少なくとも1つのC10-C12不飽和脂肪酸を含む脂肪酸の過剰な混合物の存在下で、少なくとも1つの本発明によるポリオールを、触媒を用いて、または用いないでエステル化する工程を含む。
本発明によるエステルは、好ましくは、そのまま潤滑剤基剤または潤滑剤基油として使用される。
・フェニル基またはナフチル基が、例えば、N,N’-ジフェニルフェニレンジアミン、p-オクチルジフェニルアミン、p,p-ジオクチルジフェニルアミン、N-フェニルナフチルアミン、N-フェニル-2-ナフチルアミン、N-(p-ドデシル)フェニル-2-ナフチルアミン、ジ-1-ナフチルアミン、およびジ-2-ナフチルアミン基で置換され得る、ジフェニルアミン、ジナフチルアミン、フェニルナフチルアミン;
・フェノタジン、例えばN-アルキルフェノチアジン;
・イミノ(ビスベンジル);および
・ヒンダードフェノール、例えば6-(t-ブチル)フェノール、2,6-ジ(t-ブチル)フェノール、4-メチル-2,6-ジ(t-ブチル)フェノール、4,4’-メチレンビス(2,6-ジ(t-ブチル)フェノール)。
・有機酸およびそのエステル、金属塩および無水物、例えば、N-オレイルサルコシン、ソルビタンモノオレエート、ナフテン酸鉛、ドデセニルコハク酸およびその部分エステルおよびアミド、ならびに4-ノニルフェノキシ酢酸;
・脂肪族および脂環式の第一級、第二級および第三級アミン、ならびに有機酸および無機酸のアミン塩、例えば油可溶型アルキルアンモニウムカルボキシレート;
・窒素含有複素環式化合物、例えば、チアジアゾール、置換イミダゾリン、およびオキサゾリン;
・キノリン、キノンおよびアントラキノン;
・没食子酸プロピル;
・ジノニルナフタレンスルホン酸バリウム;
・アルケニルコハク酸無水物または酸、ジチオカルバメート、ジチオホスフェートのエステルおよびアミドの誘導体、;
・アルキル酸ホスフェートのアミン塩およびその誘導体。
硫化脂肪酸および脂肪酸エステル、例えば硫化オクチルタレート;
硫化テルペン;
硫化オレフィン;
有機ポリスルフィド;
アミンホスフェート、アルキル酸ホスフェート、ジアルキルホスフェート、アミンジチオホスフェート、トリアルキルおよびトリアリールホスホロチオネート、トリアルキルおよびトリアリールホスフィン、ならびにジアルキルホスファイト、例えば、リン酸モノヘキシルエステルのアミン塩、ジノニルナフタレンスルホネートのアミン塩、トリフェニルホスフェート、トリナフチルホスフェート、ジフェニルクレジルホスフェートおよびフェニルフェニルホスフェート、ナフチルジフェニルホスフェート、トリフェニルホスホロチオネートを含む有機リン誘導体;
ジチオカルバメート、例えばジアルキルジチオカルバミン酸アンチモン;
塩素化および/またはフッ素化炭化水素およびザンセート。
5つの試料を試験する。
・エリスリトールと、n-ヘプタン酸および10-ウンデシレン酸の混合物とのエステル(本発明によるエステル);
・トリメチロールプロパンとn-ヘプタン酸とのエステル(比較例1);
・トリメチロールプロパンと10-ウンデシレン酸とのエステル(比較例2);
・トリメチロールプロパンと不飽和脂肪酸のエステル(比較例3-市販品PRIOLUBE 2044(登録商標)、CRODA製);
・ペンタエリスリトールと線状脂肪酸のエステル(比較例4-市販品NYCOBASE(登録商標)8410、NYCO製);
・ペンタエリスリトールと分岐鎖脂肪酸のエステル(比較例5-市販品NYCOBASE(登録商標)1060X、NYCO製)。
撹拌機、温度計、コンデンサーおよび窒素導入口を備えた250ml三つ口フラスコに、エリスリトール(16.4g、0.13mol)、n-ヘプタン酸(64.3g、0.49mol)および10-ウンデシレン酸(27.8g、0.15mol)を70/30の重量比で入れる。
トリメチロールプロパン(53.8g、0.4mol)およびn-ヘプタン酸(181.5g、1.38mol)を、撹拌機、温度計、コンデンサーおよび窒素導入口を備えた500mlの三口フラスコに入れる。水の理論量が安定するまで、反応混合物を窒素雰囲気下にて185℃で3時間加熱した。次いで、ジルコニウムテトラブタノラート(1.5g、ブタノール中80%、反応物の総重量の0.5重量%)を反応器にバッチ式で添加する。アセンブリを185℃で最大減圧下に3時間30分間段階的に入れ、余分な未反応酸を留去し、生成物187.4gを得る。活性化塩基性アルミナによる下流処理を粗反応生成物に対して行い、0.1mgKOH/gの酸価を有する油を得る。生成物の化学組成をガスクロマトグラフィーによって、トリメチロールプロパントリヘプタノアート98.8%およびトリメチロールプロパンジヘプタノアート0.03%、と確立した。
トリメチロールプロパン(40.4g、0.30mol)および10-ウンデシレン酸(218g、1.17mol)を、撹拌機、温度計、コンデンサーおよび窒素導入口を備えた500ml三つ口フラスコに入れる。水の理論量が安定するまで、反応混合物を窒素雰囲気下にて185℃で3時間加熱した。次いで、ジルコニウムテトラブタノラート(3.2g、ブタノール中80%、反応物の総重量の1重量%)を反応器にバッチ式で添加する。アセンブリを185℃で最大減圧下に3時間30分間段階的に入れ、超過の未反応酸を留去し、生成物195.3gを得る。
酸化安定性は、酸素誘導時間および酸素誘導温度の2つを測定することによって決定される。酸素誘導時間および酸素誘導温度は、示差走査熱量計(DSC)で測定される。
動粘度は、規格ISO 3104に従って40℃および100℃で測定した。
粘度指数(単位なし)は、規格ASTM D 2270に記載の試験方法に従って測定される。結果を以下の表2に示す。
Claims (16)
- 少なくとも1つのポリオールと、少なくとも1つのC5-C12飽和脂肪酸および少なくとも1つのC10-C12不飽和脂肪酸を含む脂肪酸の混合物とのエステル。
- 混合物が主に線状脂肪酸からなる、請求項1に記載のエステル。
- C5-C12飽和脂肪酸がn-ヘプタン酸である、請求項1または2に記載のエステル。
- C10-C12不飽和脂肪酸が10-ウンデシレン酸である、請求項1~3のいずれか一項に記載のエステル。
- C5-C12飽和脂肪酸とC10-C12不飽和脂肪酸との重量比が、1:10~10:1である、請求項1~4のいずれか一項に記載のエステル。
- C5-C12飽和脂肪酸とC10-C12不飽和脂肪酸との重量比が、8:2~2:8である、請求項1~5のいずれか一項に記載のエステル。
- C5-C12飽和脂肪酸とC10-C12不飽和脂肪酸との重量比が、7:3である、請求項1~6のいずれか一項に記載のエステル。
- ポリオールと脂肪酸の混合物との重量比が少なくとも1:5である、請求項1~7のいずれか一項に記載のエステル。
- C5-C12飽和脂肪酸およびC10-C12不飽和脂肪酸が再生可能資源に由来する、請求項1~8のいずれか一項に記載のエステル。
- C5-C12飽和脂肪酸およびC10-C12不飽和脂肪酸がヒマシ油に由来する、請求項3および4のいずれか一項に記載のエステル。
- ポリオールが、ソルビトール、エリスリトール、キシリトール、マンニトール、トリメチロールプロパン、トリメチロールエタン、ペンタエリスリトール、ジペンタエリスリトール、トリペンタエリスリトール、テトラペンタエリスリトール、マルトース、ラクトース、スクロース、ラフィノース、マルトトリオース、およびネオペンチルグリコールからなる群から選択されるかまたはそれらの混合物である、請求項1~10のいずれか一項に記載のエステル。
- ポリオールが再生可能資源に由来する、請求項1~11のいずれか一項に記載のエステル。
- 請求項1~12のいずれか一項で定義される、少なくとも1つのポリオールと、少なくとも1つのC5-C12飽和脂肪酸および少なくとも1つのC10-C12不飽和脂肪酸を含む脂肪酸の混合物とのエステルの、潤滑剤基剤としての使用。
- 請求項1~12のいずれか一項で定義される、少なくとも1つのポリオールと、少なくとも1つのC5-C12飽和脂肪酸および少なくとも1つのC10-C12不飽和脂肪酸を含む脂肪酸の混合物とのエステルを含む、潤滑剤基剤の組成物。
- 少なくとも1つのC5-C12飽和脂肪酸および少なくとも1つのC10-C12不飽和脂肪酸を含む脂肪酸の混合物を、少なくとも1つのポリオールにより、任意選択的に触媒の存在下でエステル化することを含む、エステルの調製方法。
- 請求項15に記載の方法によって得られる、少なくとも1つのポリオールと、少なくとも1つのC5-C12飽和脂肪酸および少なくとも1つのC10-C12不飽和脂肪酸を含む脂肪酸の混合物とのエステル。
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FR1900786A FR3092112B1 (fr) | 2019-01-29 | 2019-01-29 | Huile de base lubrifiante synthetisee a partir d’esters de polyols et d’acides gras biosources |
FR1900786 | 2019-01-29 | ||
PCT/FR2020/050138 WO2020157433A1 (fr) | 2019-01-29 | 2020-01-29 | Huile de base lubrifiante synthetisee a partir d'esters de polyols et d'acides gras biosources |
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Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20240524 |