JP2021533131A - グリコールアルデヒドからモノエタノールアミンを製造するための方法及び触媒系 - Google Patents
グリコールアルデヒドからモノエタノールアミンを製造するための方法及び触媒系 Download PDFInfo
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- JP2021533131A JP2021533131A JP2021505774A JP2021505774A JP2021533131A JP 2021533131 A JP2021533131 A JP 2021533131A JP 2021505774 A JP2021505774 A JP 2021505774A JP 2021505774 A JP2021505774 A JP 2021505774A JP 2021533131 A JP2021533131 A JP 2021533131A
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- catalyst
- acid
- monoethanolamine
- glycolaldehyde
- reaction mixture
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- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- OJTDGPLHRSZIAV-UHFFFAOYSA-N propane-1,2-diol Chemical compound CC(O)CO.CC(O)CO OJTDGPLHRSZIAV-UHFFFAOYSA-N 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 239000012048 reactive intermediate Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000019635 sulfation Effects 0.000 description 1
- 238000005670 sulfation reaction Methods 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000003911 water pollution Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
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Abstract
Description
(ELxAlyPz)O2、
式中、ELは、ケイ素、マグネシウム、亜鉛、鉄、コバルト、ニッケル、マンガン、クロム、及びそれらの混合物からなる群から選択される元素であり、xはELのモル分率であり、多くの場合少なくとも0.005であり、yはアルミニウムのモル分率であり、少なくとも0.01であり、zはリンのモル分率であり、少なくとも0.01であり、x+y+z=1である。ELが金属の混合物である場合、xは存在する元素混合物の総量を表す。種々のELAPO分子ふるいの調製は当技術分野に周知であり、米国特許第5,191,141号(ELAPO);米国特許第4,554,143号(FeAPO);米国特許第4,440,871号(SAPO);米国特許第4,853,197号(MAPO、MnAPO、ZnAPO、CoAPO);米国特許第4,793,984号(CAPO);米国特許第4,752,651号、及び米国特許第4,310,440号に見出すことができる。代表的なELAPO分子ふるいにはALPO及びSAPO分子ふるいがある。
下記をHastelloy製の100mlのParr反応器に充填した:1グラムのグリコールアルデヒド二量体、1.5グラムの湿ったラネーニッケル(W.R. Grace & Co.)、及び20mlのNH4OH(28%)中の0.18グラムのアルミニウムトリス(トリフルオロメタンスルホナート)(Al−トリフラート)。反応器をN2で2回パージし、次いで、6.2MPa(900psi)H2を充填した。反応混合物を、1100rpmで2時間85℃(185°F)で撹拌した。この期間の後で、反応器を室温に冷却し、反応混合物を濾過して、ニッケル触媒を無色の生成混合物から分離した。この混合物のガスクロマトグラフ(GC)分析に基づいて計算された収率は、93%モノエタノールアミン収率、2%エチレングリコール収率、及び0.5%ジエタノールアミン収率であった。
いくつかの実験を実施して、可溶化された(均一)共触媒としての種々の金属トリフルオロメタンスルホナート(トリフラート)の性能を調査した。各場合に、28%アンモニア水溶液中の5重量%のグリコールアルデヒド二量体を含む原料を、固定量のラネーニッケル及び金属トリフラートと共に、ハイスループットスクリーニングバッチ反応器内で反応させた。ラネーニッケル触媒も金属トリフラート共触媒もなしに、並びにラネーニッケル触媒のみ(金属トリフラート共触媒の非存在下)で、対照実験も実施した。触媒的還元的アミノ化反応を、密封された水素化分解反応器内で、85℃(185°F)及び8.27MPa(1200psi)水素圧の下で、2時間の保持時間で実施した。固体触媒からの分離後に、反応生成物をGCにより分析した。結果は、ラネーニッケルのみの使用と比べて金属トリフラートを共触媒として使用すると、モノエタノールアミンの選択性が増大され得ることを実証した。グリコールアルデヒド転化レベル、副生成物プロピレングリコール及びエチレングリコールへの選択性、並びにモノエタノールアミンへの選択性を含む結果を図1に示す。
いくつかの実験を実施して、種々の固体(不均一)酸共触媒の性能を調査した。各場合に、28%アンモニア水溶液中に5重量%グリコールアルデヒド二量体を含む原料を、固定量のラネーニッケル及び固体酸共触媒と共に、ハイスループットスクリーニングバッチ反応器内で反応させた。ラネーニッケル触媒のみ(固体酸共触媒の非存在下)で、参照実験も実施した。触媒的還元的アミノ化反応を、密封された水素化分解反応器内で、85℃(185°F)及び8.27MPa(1200psi)水素圧の下で、2時間の保持時間で実施した。固体触媒からの分離後に、反応生成物をGCにより分析した。結果は、ラネーニッケルのみの使用と比べて、ゼオライト並びに酸性化された活性炭及び水和又は酸性型の酸化スズなどの固体酸を含む固体酸共触媒を使用すると、モノエタノールアミンへの選択性及びその結果モノエタノールアミンの収率が、増大され得ることを実証した。種々の固体酸共触媒のエタノールアミン及びジエタノールアミン収率結果を図2に示す。
いくつかの実験を実施して、固体(不均一)酸共触媒としての種々のゼオライトの性能を調査した。各場合に、28%アンモニア水溶液中に5重量%グリコールアルデヒド二量体を含む原料を、固定量のラネーニッケル及びゼオライトと共に、ハイスループットスクリーニングバッチ反応器内で反応させた。ラネーニッケル触媒のみ(ゼオライトの非存在下)で、参照実験も実施した。別の実験を、ラネーニッケル及び均一共触媒としての酢酸アンモニウムにより実施した。触媒的還元的アミノ化反応を、密封された水素化分解反応器内で、85℃(185°F)及び8.27MPa(1200psi)水素圧の下で、2時間の保持時間で実施した。固体触媒からの分離後に、反応生成物をGCにより分析した。結果は、ラネーニッケルのみの使用と比べて、ゼオライトを固体(不均一)酸共触媒として使用すると、モノエタノールアミンの選択性が、増大され得ることを実証した。モノエタノールアミンへの選択性、並びに副生成物エチレングリコール、エチレンジアミン、及びジエタノールアミンへの選択性を含む結果を図3に示す。
Claims (20)
- モノエタノールアミンを製造する方法であって、
水素化触媒及び酸共触媒の両方の存在下で、グリコールアルデヒドをアミノ化剤と還元的アミノ化条件下で反応させて前記モノエタノールアミンを製造することを含む方法。 - 前記還元的アミノ化条件が、20℃〜200℃の温度、3MPa〜20MPaの水素分圧、及び0.5時間〜10時間の滞留時間を含む、請求項1に記載の方法。
- 前記グリコールアルデヒドが、少なくとも70%のモノエタノールアミンへのモル選択性で転化される、請求項1又は請求項2に記載の方法。
- 前記グリコールアルデヒドが、10%未満のジエタノールアミンへのモル選択性で転化される、請求項1〜3のいずれか一項に記載の方法。
- 前記反応が、前記グリコールアルデヒド及び前記アミノ化剤が加えられる水性反応混合物中で起こる、請求項1〜4のいずれか一項に記載の方法。
- 前記酸共触媒が、前記水性反応混合物中の固体である、請求項5に記載の方法。
- 前記酸共触媒が、200〜1200μmol/gのルイス酸部位の密度を有する、請求項6に記載の方法。
- 前記酸共触媒が、ゼオライト若しくは非ゼオライトの分子ふるい、金属酸化物、活性炭、又は樹脂を含む、請求項6に記載の方法。
- 前記酸共触媒が、200未満のシリカ対アルミナのモル骨格比を有するゼオライト分子ふるいである、請求項8に記載の方法。
- 前記酸共触媒が、FAU、FER、MEL、MTW、MWW、MOR、BEA、LTL、MFI、LTA、EMT、ERI、MAZ、MEI、及びTONからなる群から選択される構造型を有するゼオライト分子ふるいである、請求項8又は請求項9に記載の方法。
- 前記構造型がBEA又はMFIである、請求項10に記載の方法。
- 前記酸共触媒が前記水性反応混合物に可溶化されている、請求項5に記載の方法。
- 前記酸共触媒が金属トリフラートである、請求項12に記載の方法。
- グリコールアルデヒドが、前記酸共触媒の非存在下で得られる基準モル選択性を少なくとも3%超えるモノエタノールアミンへのモル選択性で転化される、請求項1〜13のいずれか一項に記載の方法。
- 前記グリコールアルデヒドが、アルドース又はケトースの熱分解により得られる、請求項1〜14のいずれか一項に記載の方法。
- 前記モノエタノールアミンの少なくとも一部を硫酸エステル化して、2−アミノエチル硫酸を製造すること;及び
前記2−アミノエチル硫酸の少なくとも一部をスルホン化して、タウリンを製造すること
をさらに含む、請求項1〜15のいずれか一項に記載の方法。 - モノエタノールアミンを製造する方法であって、
水素含有雰囲気を供給する反応器内で、グリコールアルデヒド及びアミノ化剤を含む水性原料を、水素化触媒及び酸共触媒と接触させて、前記モノエタノールアミンを製造することを含み、
前記酸共触媒が、前記水性原料が加えられる反応混合物中で均一又は不均一である方法。 - 前記酸共触媒が前記反応混合物中で不均一であり、前記方法が連続的に実施される、請求項17に記載の方法。
- モノエタノールアミンを製造する方法であって、
水性反応混合物及び水素を水素化触媒及び酸共触媒の両方と還元的アミノ化条件下で接触させることにより、反応物としてアンモニア水溶液と共に前記水性反応混合物に加えられるグリコールアルデヒドの還元的アミノ化を実施することを含み、
前記水素化触媒及び前記酸触媒の組み合わせにより前記還元的アミノ化が触媒され、前記モノエタノールアミンが理論収率の少なくとも70%の収率で製造される方法。 - 前記水素化触媒及び前記酸触媒が、固体二元機能触媒の粒子の形態で一体化している、請求項19に記載の方法。
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EP3830071A1 (en) | 2021-06-09 |
WO2020028322A1 (en) | 2020-02-06 |
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