JP5147714B2 - 分岐した炭化水素成分の製造方法 - Google Patents
分岐した炭化水素成分の製造方法 Download PDFInfo
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- JP5147714B2 JP5147714B2 JP2008545028A JP2008545028A JP5147714B2 JP 5147714 B2 JP5147714 B2 JP 5147714B2 JP 2008545028 A JP2008545028 A JP 2008545028A JP 2008545028 A JP2008545028 A JP 2008545028A JP 5147714 B2 JP5147714 B2 JP 5147714B2
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Classifications
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
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- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G3/00—Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
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- C10G45/64—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds to change the structural skeleton of some of the hydrocarbon content without cracking the other hydrocarbons present, e.g. lowering pour point; Selective hydrocracking of normal paraffins characterised by the catalyst used containing crystalline alumino-silicates, e.g. molecular sieves
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- C10G65/00—Treatment of hydrocarbon oils by two or more hydrotreatment processes only
- C10G65/02—Treatment of hydrocarbon oils by two or more hydrotreatment processes only plural serial stages only
- C10G65/04—Treatment of hydrocarbon oils by two or more hydrotreatment processes only plural serial stages only including only refining steps
- C10G65/043—Treatment of hydrocarbon oils by two or more hydrotreatment processes only plural serial stages only including only refining steps at least one step being a change in the structural skeleton
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- C10G69/00—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one other conversion process
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- C10G69/04—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one other conversion process plural serial stages only including at least one step of catalytic cracking in the absence of hydrogen
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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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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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- C10G2300/1014—Biomass of vegetal origin
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Description
JP 01 056 792は、高分子量のポリブテンまたはポリイソブチレンを併用した、多くの分岐構造を有するC 30 H 62 の分子式で表される分岐した炭化水素であるスクワランを含む食品加工用潤滑剤について開示している。S.T.Gui, P.T.Cummings, H.D.Cochran, J.D.Moore, S.A.Guptaによる「直鎖状および分岐したアルカンの流動学の非平衡分子動力学シミュレーション」International Journal of Thermophysics, 449〜459ページは、直鎖状および分岐した炭化水素の流動学のNEMDシミュレーションについて言及している。特に、C10(n−デカン、融解Tm=−30℃)、C16(n−ヘキサデカン、Tm=18℃)、C24(n−テトラコサン、Tm=52℃)、C25(10−n−ヘキシルノナデカン)およびC30スクワランについて研究されている。US 4 026 960は、精密機器(クロノメーター)のための潤滑剤として使用される、スクワランと非常に良く似た性質を有する2,7,10,15,18,23−ヘキサメチルテトラコサンについて開示している。
US4,317,948は、転換反応によってアルファ−および分子内オレフィンから潤滑油を製造するための方法を示している。
US2004/230085は、水素化脱酸素化、続く水素化異性化による、脂肪酸または脂肪酸エステルなどの、生物起源からのディーゼル級炭化水素の製造に関係している。
US3,501,546は、チタン担持Pd触媒を用いることによって、24までの炭素原子を有するアルコールまたはアルデヒドからワックス状のパラフィンおよびオレフィンを製造する方法を開示している。該方法では、反応するフィード分子の1つの炭素が失われ、制限された分岐を有する生成物が得られる。
本発明の方法はアルデヒドおよびケトンの縮合段階を含む。アルデヒドおよびケトンは好ましくは脂肪酸または糖質に由来する。下記の式Iに表されている反応において、原料油の分子が互いに反応し、従って分岐成分の炭素鎖長の増加がそれゆえ得られる。さらに、本発明の方法は縮合生成物からヘテロ原子を除去するための水素化脱酸素段階、そして最後に、分子骨格に分岐を形成するための異性化段階を含む。従って、パラフィン系製品の低温特性が改善される。
およびR=C2〜C22である。
本発明は本明細書において、添付の図1によって例示されるが、該図の実施様態に本発明の範囲を制限する意図ではない。
方法の原料油は、C1〜C40アルデヒド、C3〜C79ケトンおよびC2〜C40水酸化アルデヒド、およびそれらの混合物からなる群より選択される少なくとも1つのアルデヒドまたはケトンを含む。合成のおよび生物由来の両方のアルデヒドおよびケトンが、原料油として用いられる。好ましくは生物由来である、随意的に1または複数の公知技術の精製および/または調整段階に付されたC4〜C24脂肪族アルデヒド、C3〜C47ケトンおよびC4〜C24水酸化アルデヒドが、好ましくは使用される。調整段階は、例えば、アルデヒドを生じるアルコールの還元、またはケトンを生じる脂肪酸または脂肪酸アルキルエステルのケトン化のみならず、脂肪酸を製造するための水素化、アルコールまたは酸とのエステル交換、脂肪酸アルキルエステルを製造するためのエステル交換、アルコールを生じる脂肪酸または脂肪酸アルキルエステルの還元を含む。
a)植物性脂肪、植物油、植物ワックス、動物性脂肪、動物油、動物ワックス、魚脂肪、魚油、魚ワックス、および
b)植物性脂肪、植物油、植物ワックス、動物性脂肪、動物油、動物ワックス、魚脂肪、魚油、魚ワックス植物からの加水分解、酸エステル変換または熱分解反応によって得られる遊離脂肪酸または脂肪酸、および
c)植物性脂肪、植物油、植物ワックス、動物性脂肪、動物油、動物ワックス、魚脂肪、魚油、魚ワックス、植物からエステル交換によって得られるエステル、および
d)植物、動物および魚由来の脂肪酸とアルコールのエステル化によって得られる脂肪酸アルキルエステル、および
e)植物性脂肪、植物油、植物ワックス、動物性脂肪、動物油、動物ワックス、魚脂肪、魚油、魚ワックスからの遊離脂肪酸または脂肪酸の還元または加水分解性生物として得られるアルコールおよびアルデヒド、および
f)植物性脂肪、植物油、植物ワックス、動物性脂肪、動物油、動物ワックス、魚脂肪、魚油、魚ワックスから得られる遊離脂肪酸、エステル、アルコールまたはアルデヒドのケトン化反応によって得られるケトン、および
g)生物由来のワックスから加水分解、エステル交換および熱分解によって得られる脂肪族アルコール
h)食品用脂肪およびオイルの廃棄物ならびに回収物、および遺伝子工学によって得られた脂肪、油、およびワックス、および
i)該出発材料の混合物
縮合段階
C1〜C40アルデヒド、C3〜C79ケトンおよびC2〜C40水酸化アルデヒド、およびそれらの混合物からなる群より選択される少なくとも1つの成分を含む原料油が縮合反応に付される。アルデヒドおよび/またはケトンは縮合され、実質的に炭化水素蒸気の炭素数を増加させる。飽和のアルデヒドおよびケトンが好ましくは原料油として用いられる。方法において、アルドール縮合反応が好ましくは用いられ、これゆえ分岐を有する不飽和のアルデヒドまたはケトンが得られる。縮合において、均一または不均一系アルドール縮合触媒が用いられうる。Na/SiO2のような担持されたアルカリ金属触媒が不均一系触媒として挙げられる。均一系触媒は、好ましくは、NaOH、KOHまたはCa(OH)2のようなアルカリまたはアルカリ土類金属水酸化物である。反応温度は80〜400℃で、好ましくはより低い温度がより小さい分子量フィードに用いられ、より高い温度がより大きい分子量フィードに用いられる。随意的にはアルコールのような溶媒が用いられてもよい。反応で使用される均一系触媒の量は1〜20重量%の間でさまざまであるが、好ましくは1.5〜19重量%である。代わりに、アルドール縮合の反応条件は反応生成物として、アルドールのような水酸化アルデヒドを生じるために調整されてもよく、これゆえ、二重結合の反応に基づくオリゴマー化を最小限にされうる。この場合、水酸基もまた次のHDO段階で水として除去されねばならない。
その後のHDO段階において、アルドール縮合反応で得られた生成物のヘテロ原子が除去される。本発明による方法のHDO段階で、アルドール縮合の生成物および水素ガスは、0.1〜20MPaの間の範囲の圧力のもと、好ましくは1〜15MPaの間で、100〜500℃である温度、好ましくは150〜350℃の間、特に好ましくは200〜350℃の間で、流速WHSVが0.1〜10 l/hの範囲で反応される。HDO段階において、元素周期系の第VIII族および/または第VIA族金属を含む特別な触媒、およびアルミナおよび/またはシリカが用いられうる。HDO触媒は好ましくは担持されたPd、Pt、Rh、Ru、Ni、NiMoまたはCoMo触媒であって、担体は活性化された炭素、アルミナ、および/またはシリカである。
HDOおよび随意的の精製段階の後、水素化異性化が、水素気体、水素化された成分、および随意的に添加されたパラフィン系フィードを反応させることによって、異性化触媒の存在の下行われる。水素異性化段階において圧力は0.1〜20MPaの圧力範囲で、好ましくは1〜15MPaである。温度は100〜500℃の間の範囲で、好ましくは200〜400℃の間である。水素化異性化段階においては、モレキュラーシーブおよび元素周期系の第VIII族の金属を含む特別な触媒、例えば、Ni、Pt、およびPdなどが使われる。アルミナおよび/またはシリカが担体として使用される。
アルドール縮合から得られる生成物同様、原料油が、緩やかな条件で、不飽和のアルコールなどの、水素化可能な二重結合を水素化するために、および触媒の活性は主にその表面でのコール生成によって失われるので、次の加工段階でのコーク生成を減少させるために、随意的な前水素化段階に付された。前水素化は水素化触媒の存在下、50〜400℃の間の温度で、0.1〜20MPaの間の範囲の水素圧の下、好ましくは、100〜300℃の間の温度、1〜10MPaの範囲の水素圧で行われる。前水素化触媒は元素周期系の第VIII族および/または第VIA族の金属を含む。前水素化触媒は好ましくは担持されたPd、Pt、Ni、Ru、Rh、Cu、CuCr、NiMoまたはCoMo触媒であり、担体は活性化された炭素、アルミナおよび/またはシリカのいずれかである。
水素化異性化段階につづいて、随意的の脱ろう段階が触媒的にまたは溶剤脱ろうのどちらかによって行われる。触媒的な脱ろうにおいて、任意のパラフィン系添加フィードと同様、水素ガスおよび異性化される成分は脱ろう触媒の存在下反応する。元素周期系の第VIII族の金属、例えばNi、Pt、およびPdを含むゼオライト触媒が相応に使用される。脱ろう段階において、圧力は0.1〜20MPaの範囲で様々であり、温度は100〜500℃の間である。
上記で得られた生成物は、随意的に二重結合および芳香族化合物を除去するために最終加工に付されうる。該最終加工が、触媒の存在下水素を用いて行われる場合、水素化最終加工と呼ばれ、圧力がこれゆえ1〜20MPaの範囲で、好ましくは2〜15MPaの間、50〜500℃の間の範囲の温度、好ましくは200〜400℃の間で行われる。水素化最終加工では、元素周期系の第VIII族の金属を含む特別な触媒およびアルミナおよび/またはシリカが使用される。水素化最終加工の触媒は、好ましくは担持されたPd、Pt、またはNi触媒であり担体はアルミナおよび/またはシリカである。最終加工は、クレイやモレキュラーシーブスのような吸収性の材料を用いて極性成分を除去することによってもなされる。
本発明による方法は、ベースオイルに適切な、高品質な枝分かれ構造を有する飽和炭化水素成分を与える。ベースオイル生成物は非常にすばらしい粘性および低温特性をもつ。本発明による方法は、副生成物として、ディーゼル燃料プールに適したパラフィン系炭化水素生成物を与える。ディーゼル成分は一般的にいくつかの短い炭素−炭素側鎖を含み、結果として非常に低い曇点および低温フィルター目詰まり点をもつが、依然として高いセタン価を有する。加えて、溶媒、ガソリン、および/またはガソリンの成分に適した炭化水素の成分が副生成物として得られた。全てのこれらの生成物は好ましくは生物由来である。
1.本発明のベースオイルは、C18アルデヒドを含むフィードをアルドール縮合、水素化、および水素化異性化することによって得られる。
2.本発明のベースオイルは、C23ケトンおよびC5アルデヒドを含むフィードをアルドール縮合、水素化、および水素化異性化することによって得られる。
3.本発明のベースオイルは、C23ケトンを含むフィードをアルドール縮合、水素化、および水素化異性化することによって得られる。
4.GTLはフィッシャー−トロプシュワックス状留分の異性化生成物である。
5.SWは、鉱物油由来の軟ろうのワックス状留分の異性化生成物である。
6.VHVIは鉱物油由来の水素化分解され異性化されたベースオイルである。
1 C(n).H(2n+2) パラフィン
2 C(n).H(2n) モノナフテン
3 C(n).H(2n−2) ジナフテン
4 C(n).H(2n−4) トリナフテン
5 C(n).H(2n−6) テトラナフテン
6 C(n).H(2n−8) ペンタナフテン
本発明の方法は、副生成物としてのディーゼルおよびガソリン成分のみならず、再生可能な天然原料由来のベースオイル製造のための、ヘテロ原子を含む、生物由来の再生可能な出発材料の使用を特に許す。従来の粗油に加えて、高品質な分岐を有するパラフィン系ベースオイルのための完全に新しい原料が、本発明により提供される。またグリーンハウス効果に寄与している二酸化炭素排出もまた、再生利用不可能なものに代えて再生利用可能な原材料を使用することによって減少させることができる。
C16アルデヒドからの炭化水素成分の製造
アルドール縮合反応のため、パーム油由来のC16脂肪族アルデヒド200gおよび水に溶解された20%NaOH100gがパール反応器に入れられた。混合は250rpmで、温度は250℃に、そして圧力は0.5MPaに調整された。緩やかな窒素パージが、反応から遊離される水を取り除くために維持された。反応は、GC分析で縮合したアルデヒドの量が安定化されるまで行われた。反応後、生成物は塩酸によって中和され、水で洗浄され、そして塩化カルシウムで乾燥された。
C23ケトンおよびフルフラールからの炭化水素成分の製造
アルドール縮合段階において、14.6gのラウロン(パーム核油由来のC23ケトン)、150mlのイソプロパノールおよび15mlの10%NaOH水溶液が混合され、そして、丸底フラスコ中で80℃にて20分間還流された。15gのフルフラール(アルドヘキソース糖由来のアルデヒド)が添加され、そして加熱還流が5時間継続された。放冷後、アルコールがロータリーエバポレーターによって蒸発させられた。反応は繰り返され、そして2度の合成からの残渣が酢酸エチルに溶解され、氷中で冷却され、そして未反応のラウロンが低温溶液からろ過された。
植物油由来のケトンからの炭化水素成分の製造
アルドール縮合段階において、10gのパーム油脂肪酸由来のC31/C33/C35ケトン混合物および2gのNaOHが丸底フラスコ中撹拌下30分間400℃まで加熱された。放冷後、合成生成物が50mlの酢酸エチルに溶解され、ろ過され、そして希釈液が蒸発させられた。
水素化異性化
実施例1で得られたC32パラフィンワックスが、パール反応器中で、還元されたPtモレキュラーシーブ/Al2O3触媒を用いて異性化され、ベースオイルクラスの分岐のパラフィンを得た。前加熱されたパラフィンは、340℃で3MPaの水素圧の下、−15℃未満の流動点が得られるまで異性化された。最終的に、軽い留分は減圧下生成物から蒸留された。
Claims (18)
- C1〜C40アルデヒド、C3〜C79ケトン、C2〜C40ヒドロキシアルデヒドおよびそれらの混合物からなる群より選択される少なくとも1つのアルデヒドおよび/またはケトンを含む原料油が、アルドール縮合触媒の存在下で、アルドール縮合触媒としてアルカリまたはアルカリ土類金属の水酸化物を用いて、80〜400℃の範囲の温度でアルドール縮合され、縮合生成物が水素化脱酸素化触媒の存在下、0.1〜20MPaの範囲の水素圧下、100〜500℃の範囲の温度で水素化脱酸素化され、かつその後、異性化触媒の存在下、0.1〜20MPaの範囲の水素圧下、100〜500℃の範囲の温度で水素化異性化されることを特徴とするベースオイルを製造する方法。
- 原料油が、C4〜C24脂肪族アルデヒド、C3〜C47ケトン、C4〜C24ヒドロキシアルデヒドおよびそれらの混合物からなる群より選択される少なくとも1つのフィード成分を含むことを特徴とする請求項1記載の方法。
- 前記フィード成分が、生物起源の出発材料から誘導され、該出発材料が、植物油、植物ワックスおよび植物性脂肪;動物油、動物性脂肪および動物ワックス;魚油、魚脂肪および魚ワックス;食品用脂肪および油の回収物;遺伝子工学によって得られる脂肪、油およびワックス;藻類および昆虫由来の油および脂肪;酸加水分解法によって糖質から製造されるアルデヒドおよびケトン、ならびに該出発材料の混合物からなる群より選択されることを特徴とする請求項2記載の方法。
- 水素化脱酸素化が、150〜350℃の範囲の温度で、1〜15MPaの範囲の水素圧の下で行われることを特徴とする請求項1記載の方法。
- 水素化脱酸素化触媒が、元素周期系の第VIII族または第VIA族の金属からなる群より選択される少なくとも1つの成分、および担体を含むことを特徴とする請求項1記載の方法。
- 前記元素周期系の第VIII族または第VIA族の金属が、Pd、Pt、Rh、Ru、Ni、NiMoまたはCoMo金属であることを特徴とする請求項5記載の方法。
- 前記担体が、活性炭、アルミナおよび/またはシリカ担体であることを特徴とする請求項5記載の方法。
- 水素化異性化が、1〜15MPaの範囲の水素圧の下、200〜400℃の範囲の温度で行われることを特徴とする請求項1記載の方法。
- 水素化異性化触媒が、元素周期系の第VIII族の金属、モレキュラーシーブを担体とともにまたは担体なしで含むことを特徴とする請求項1記載の方法。
- 前記元素周期系の第VIII族の金属がPd、PtまたはNi金属であることを特徴とする請求項9記載の方法。
- 前記担体がアルミナおよび/またはシリカであることを特徴とする請求項9記載の方法。
- 縮合の前に、前水素化が、0.1〜20MPaの間の水素圧の下で、50〜400℃の間の温度で、前水素化触媒の存在下で行われることを特徴とする請求項1記載の方法。
- 前記前水素化が、1〜10MPaの間の水素圧の下で行われることを特徴とする請求項12記載の方法。
- 前記前水素化が、150〜300℃の間の温度で行われることを特徴とする請求項12記載の方法。
- 前水素化触媒が、担持された、元素周期系の第VIII族および/または第VIA族の金属を含むことを特徴とする請求項12記載の方法。
- 前記前水素化触媒が、担持されたPd、Pt、Rh、Ru、Ni、Cu、CuCr、NiMoまたはCoMo触媒であり、担体が、活性炭、アルミナおよび/またはシリカであることを特徴とする請求項15記載の方法。
- 炭化水素または炭化水素の混合物が、原料油におよび/または製法段階で希釈液として添加されることを特徴とする請求項1記載の方法。
- 副生成物として、ディーゼル成分およびガソリンが製造されることを特徴とする請求項1〜17のいずれかに記載の方法。
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FI20055665L (fi) * | 2005-12-12 | 2007-06-13 | Neste Oil Oyj | Prosessi haarautuneen hiilivetykomponentin valmistamiseksi |
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