JP6831359B2 - 生物学的原材料から得られたパラフィンフラクションを含む組成物及びそれを製造する方法 - Google Patents
生物学的原材料から得られたパラフィンフラクションを含む組成物及びそれを製造する方法 Download PDFInfo
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- JP6831359B2 JP6831359B2 JP2018204951A JP2018204951A JP6831359B2 JP 6831359 B2 JP6831359 B2 JP 6831359B2 JP 2018204951 A JP2018204951 A JP 2018204951A JP 2018204951 A JP2018204951 A JP 2018204951A JP 6831359 B2 JP6831359 B2 JP 6831359B2
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- C07C9/00—Aliphatic saturated hydrocarbons
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Description
一つの例示的な組成物は、例えば、生物学的エステルの構造又はトリグリセリド成分を分解するため及び酸素、リン及び硫黄化合物を除去し、同時にオレイン結合を水素化するための水素化脱酸素(HDO)ステップを第一に含み、このようにして得られた生成物の異性化に続き、従って炭化水素鎖を分枝させ、パラフィンの低温特性を向上させる、プロセスを使用して、生物起源の出発材料から製造される。生成物は、蒸留によって分別(分留)されて(fractionated)、所望のフラクションを与える。
一つの例示的な組成物は、生物学的原材料から製造されたパラフィンの蒸留によって得られる。パラフィンは、生物学的原材料の水素化脱酸素、及び任意的に水素化脱酸素から得られたn‐パラフィン混合物の異性化を含む方法によって製造されてもよい。
[適用性評価]
適用性評価のために使用された材料及び化学品は、以下の(表2)に表される。
分留で得られた全ての9つのフラクションは、それらの物質的性質について分析された。物質的性質及び使用された標準的な方法のリストは、以下の(表3)に示される。
組成分析の目的は、分析された不飽和炭化水素、芳香族、硫黄及びベンゼン含有量である特定の構成成分の分析を含めて、フラクションの炭素分布及び構造を決定することである。
炭素数及び構造分析は、フレームイオン化検出器(FID)を備えたガスクロマトグラフィー法によって行われた。方法は、サンプル内のn‐パラフィン及びパラフィン異性体を決定するために使用される。それは、C6からC36までの範囲に渡る炭素数で分析するために有効であり、個々の構成成分についての定量化の限界は、0.01重量%である。
臭素指数決定は、ASTM D2710([引用文献92])及び修正されたASTM D2710に従って行われた。それは、臭素指数に換算してサンプル内の痕跡量の不飽和化合物を測定するための方法である。臭素指数は、サンプル100グラムと反応し得る臭素のミリグラム数である。本方法の原理は、特定の溶媒内に溶解した既知の質量のサンプルが、標準の臭化物‐臭素酸塩溶液を用いて滴定されることである。終点は、遊離した臭化物の存在が系の電気伝導度に急激な変化を引き起こしたときに、電気的底装置によって示される。それは、100より低い臭素指数を有するサンプルに適用可能である。
芳香族含有量を規定するために、紫外線(UV)‐分光光度計によって芳香族炭化水素の吸収が既知の波長で測定される試験が、芳香族含有量決定のために使用された。
サンプル内の総硫黄含有量を決定するために、ASTM D5453が使用された([引用文献95])。試験は、ネステオイル社中央研究所によって行われた。サンプルは高温燃焼チューブの中に注入され、そこで酸素に富む雰囲気中で硫黄が酸化されて二酸化硫黄になる。次いで、二酸化硫黄は、UV光からエネルギーを吸収してその励起状態に変換される。硫黄含有量は、高電子増倍管を用いて二酸化硫黄から放射される蛍光を測定することによって決定される。
痕跡量のベンゼンは、質量分光分析を用いてガスクロマトグラフィーによって測定される。
予備的適用性評価は3つの部分を含み、それは、化学的適合性、エマルジョン形成能力及び顔料分散安定性である。サンプル量の制限に起因して、パイロット規模分留からの4つのフラクションのみが、下記の適用性評価について試験された。
液体状態又は固体状態の両方における、フラクションと試験材料との間の適合性は、C.Chiyodaら([引用文献97])及びC.Bordesら([引用文献54])によって記述された実験に基づく方法によって評価された。
ここで、(数2)は、混合後の試験材料の重量である。
(数3)は、混合前の試験材料の重量である。
*全ての値は最初からの百分率変化として与えられる。
**百分率の維持された機械的性質は、引張強度、延長、係数、柔軟強度及び衝撃強度を含む。%の維持が100%よりも大きい場合は、200から%の維持された性質を引いた値が計算に使用される。
***この種の報告の情報の多様さに起因して、この情報はガイドラインとしてのみ使用され得る。
乳化剤の存在によってサンプルと水との間にエマルジョンを形成する能力を評価するために、方法は、石油及び合成流体の水分離可能性に関するASTM D1401標準試験方法([引用文献100])、Daaou及びBendedouchによってなされた実験([引用文献101])及び乳化剤製造業者からの技術データシート([引用文献102]、[引用文献103]、[引用文献104])に基づく。加えて、ベースラインとして界面活性剤を用いない試験が行われた。乳化剤を融解するための相及び添加の順序を変化させることによって、W/O及びO/Wエマルジョンの両方が調製された([引用文献105])。表5は、各乳化剤についてのエマルジョン調製を要約する。W/Oエマルジョンに関して、乳化剤の融解温度より低い引火点を有するフラクションについての試験は省略された。次いで、混合物は、1500±15rpmの速度で5分間にわたって撹拌された。
顔料分散安定性を評価するための方法は、Q.Liらによって行われた実験([引用文献68])に基づく。15mLのサンプルは、磁石撹拌子を用いて30分間にわたって0.2gの顔料と混合された。沈降挙動は、10分、30分、1時間、1.5時間及び24時間にモニターされた。加えて、水、アセトン、キシレン及び芳香族を含まないパラフィン溶媒を用いた安定性試験は、比較のために行われた。表6における定性的尺度は、顔料分散安定性レベルを分類するために使用された。
a 1.5時間における
b 初期体積の20%に等しい沈降体積に到達するまで
イソパラフィン混合物分留からの各フラクションの収率は、質量基準及び体積基準の両方に基づいて表8に表される。
以下の表12は、イソパラフィンフラクションの物理的性質を示す。より高い沸点範囲と共に増大している性質は、引火点、アニリン点、動粘度、密度、表面張力、流動点、雲り点、相対蒸発率及び屈折率である。他方では、沸点範囲の増大と共に減少している性質は、カウリブタノール溶解度試験、溶解度パラメータ及び蒸気圧である。
イソパラフィンフラクションについて、炭素数分布は、それらの沸点範囲と対応している。NM490B及びNM291を使用した、IBP‐200℃の沸点範囲を用いたフラクションの結果は、一致している。それは、およそ87重量%のイソパラフィン、12重量%のn‐パラフィン及び1重量%のナフテンを有する。痕跡量のオレフィン、芳香族及び含酸素化合物もまた、それぞれ0.3重量%、0.03重量%及び0.07重量%だけ発見される。イソパラフィンフラクションの構成成分及び構造分析は、表15に表される。
備考:*アアルト大学学位論文の付録F.2 重量基準ppmでの芳香族含有量、及び、付録F.3 重量基準ppmでのベンゼン含有量(15℃における密度を使用)による推定。当該論文の全ての内容は、参照により本明細書に組み込まれる。具体的には、重量基準ppmでの芳香族含有量について、体積から重量基準への変換は、以下の方程式(数4)により計算される。
ここでAは芳香族含有量であり、880は単環芳香族の密度(kg/m3)であり、Dはサンプルの密度(kg/m3)である。重量基準ppmでのベンゼン含有量について、体積から質量基準への変換は、以下の方程式(数5)により計算される。
ここでBはベンゼン含有量であり、Dはサンプルの密度(kg/L)である。
備考:*上述のアアルト大学学位論文の付録F.2及び付録F.3(50℃における密度を使用)による推定。当該論文の全ての内容は、参照により本明細書に組み込まれる。
フラクションの物理的性質及び構成成分は、全ての内容が参照により本明細書に組み込まれるアアルト大学学位論文のセクション5.2“Manufacturers and Commercial aliphatic fluids”)において議論される会社が提供するイソパラフィンの市販製品と比較される。比較の詳細は、アアルト大学学位論文の付録Hに表される。情報は、製造業者のウェブサイトから集められ、したがって、物理的性質及び構成成分の全てが報告される訳ではない。概して、物理的性質、例えば引火点、アニリン点、粘度、密度は、市販製品と比較可能である。しかしながら、続く段落において議論される性質及び構成成分には、いくつかの違いがある。
予備的適用性評価は、異なる物質との化学的適合性、エマルジョン形成能力及び最後に顔料分散安定性に基づく。
備考:N/A:重量の測定が実際的ではなく視覚的結果が観察された,G:溶液がゲルになる,VL:溶液が粘性の液体になる,L:溶液が液体になる,S:膨張が起こり重量は測定不能である,DS:ポリマーがフラクションに溶解する,及び−:実験は行われていない。
備考:N/A:重量の測定が実際的ではなく視覚的結果が観察された,G:溶液がゲルになる,VL:溶液が粘性の液体になる,L:溶液が液体になる,S:膨張が起こり重量は測定不能である,DS:ポリマーがフラクションに溶解する,及び−:実験は行われていない。
以下は、上述の引用文献のリストである。
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Claims (16)
- 組成物であって、
当該組成物の総重量に基づいて40‐50重量%のC14パラフィン、及び
当該組成物の総重量に基づいて35‐45重量%のC15パラフィン、を含み、
前記C14パラフィン及び前記C15パラフィンは、生物学的原材料に由来し、かつ、
当該組成物の総イソパラフィン含有量は、当該組成物の総重量に基づいて、93重量%よりも多く、
前記C14パラフィンは、イソパラフィン及びn-パラフィンを含み、かつ、前記C15パラフィンは、イソパラフィン及びn-パラフィンを含む、
組成物。 - 当該組成物は、当該組成物の総重量に基づいて、45‐50重量%のC14パラフィン及び40‐45重量%のC15パラフィンを含む、請求項1に記載の組成物。
- 当該組成物は、当該組成物の総重量に基づいて、9重量%未満のC13パラフィン及びより軽いパラフィン、並びに、7重量%未満のC16パラフィン及びより重いパラフィンを含む、請求項1に記載の組成物。
- 当該組成物は、当該組成物の総重量に基づいて、5重量%未満のC13パラフィン及びより軽いパラフィン、並びに、3重量%未満のC16パラフィン及びより重いパラフィンを含む、請求項1に記載の組成物。
- 当該組成物の総イソパラフィン含有量は、当該組成物の総重量に基づいて、97重量%よりも多い、請求項1に記載の組成物。
- 前記C14パラフィンはイソパラフィンであり、前記C15パラフィンはイソパラフィンである、請求項1に記載の組成物。
- 前記C14パラフィンはイソパラフィンであり、前記C15パラフィンはイソパラフィンである、請求項2に記載の組成物。
- 当該組成物の総芳香族炭化水素含有量は、重量基準で1500ppm未満である、請求項1に記載の組成物。
- 当該組成物の総芳香族炭化水素含有量は、重量基準で1300ppm未満である、請求項1に記載の組成物。
- 当該組成物の総芳香族炭化水素含有量は、重量基準で500ppm未満である、請求項1に記載の組成物。
- 当該組成物は、240℃から260℃の範囲内に沸点を有する、請求項1に記載の組成物。
- 当該組成物は、245℃から255℃の範囲内に沸点を有する、請求項1に記載の組成物。
- 当該組成物は、溶媒又は溶媒成分としての使用に適する、請求項1に記載の組成物。
- 当該組成物は液体状である、請求項1に記載の組成物。
- 当該組成物はエマルジョンである、請求項1に記載の組成物。
- 当該組成物は、コーティング、塗料、ラッカー、ワニス、光沢剤(polish)、インク、接着剤、封止剤、樹脂、プラスチック、触媒、洗浄用組成物、過酸化物の減感剤、顔料分散、活性成分のためのキャリア流体、抗酸化剤、殺生物剤、殺虫剤、エアフレッシュナー、作物保護用組成物、洗剤、グリース除去用組成物、ドライクリーニング用組成物、化粧品、パーソナルケア用組成物、医薬品、歯科印象材料における増量剤、ワクチン、食品成分、フレーバー用組成物、香料、天然油抽出、油田用化学品、泥水掘削用組成物、抽出プロセス用組成物、エラストマーのための可塑剤、紙処理用化学品、潤滑剤、機能液、変圧器油、金属加工用組成物、圧延若しくは切断用流体、水処理用組成物、木材処理用組成物、建設用化学品、離型材、爆薬、鉱業用化学品、溶媒抽出用組成物、燃料用組成物、暖房用油、ランプ用油又はそれらの組み合わせにおける使用に適する、請求項1に記載の組成物。
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CA2934694C (en) | 2021-09-21 |
AU2014375087A1 (en) | 2016-07-14 |
SG11201605302SA (en) | 2016-07-28 |
JP6450397B2 (ja) | 2019-01-09 |
PL3090026T3 (pl) | 2018-03-30 |
JP2017503855A (ja) | 2017-02-02 |
RU2659040C2 (ru) | 2018-06-27 |
EP3090026A2 (en) | 2016-11-09 |
IL246255B (en) | 2018-12-31 |
BR112016015496A2 (pt) | 2018-03-27 |
CN105874039A (zh) | 2016-08-17 |
DK3090026T3 (en) | 2018-01-02 |
MX2016008775A (es) | 2017-04-04 |
CN105874039B (zh) | 2018-09-11 |
EP3090026B1 (en) | 2017-10-04 |
RU2016127653A (ru) | 2018-02-08 |
KR20160105876A (ko) | 2016-09-07 |
MY178257A (en) | 2020-10-07 |
AU2014375087B2 (en) | 2018-03-15 |
US10131848B2 (en) | 2018-11-20 |
CA2934694A1 (en) | 2015-07-09 |
US9469583B2 (en) | 2016-10-18 |
KR102288260B1 (ko) | 2021-08-09 |
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