JP2002504075A - 改良型金属―リガンド錯体触媒プロセス - Google Patents
改良型金属―リガンド錯体触媒プロセスInfo
- Publication number
- JP2002504075A JP2002504075A JP52143997A JP52143997A JP2002504075A JP 2002504075 A JP2002504075 A JP 2002504075A JP 52143997 A JP52143997 A JP 52143997A JP 52143997 A JP52143997 A JP 52143997A JP 2002504075 A JP2002504075 A JP 2002504075A
- Authority
- JP
- Japan
- Prior art keywords
- reaction product
- product fluid
- metal
- reaction
- organophosphite ligand
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
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- 238000000034 method Methods 0.000 title claims description 271
- 230000008569 process Effects 0.000 title claims description 165
- 230000003197 catalytic effect Effects 0.000 title description 20
- 239000003054 catalyst Substances 0.000 claims abstract description 196
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 139
- 239000012530 fluid Substances 0.000 claims abstract description 139
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 123
- 150000008301 phosphite esters Chemical class 0.000 claims abstract description 118
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 73
- 239000011574 phosphorus Substances 0.000 claims abstract description 70
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 64
- 150000007513 acids Chemical class 0.000 claims abstract description 26
- 238000006243 chemical reaction Methods 0.000 claims description 109
- 238000007037 hydroformylation reaction Methods 0.000 claims description 108
- 150000001299 aldehydes Chemical class 0.000 claims description 82
- 239000000047 product Substances 0.000 claims description 80
- 150000001875 compounds Chemical class 0.000 claims description 77
- 239000002253 acid Substances 0.000 claims description 73
- 238000000926 separation method Methods 0.000 claims description 57
- 239000010948 rhodium Substances 0.000 claims description 49
- 238000006460 hydrolysis reaction Methods 0.000 claims description 42
- 230000007062 hydrolysis Effects 0.000 claims description 40
- 229910052703 rhodium Inorganic materials 0.000 claims description 40
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 39
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- 230000009849 deactivation Effects 0.000 claims description 28
- 150000002897 organic nitrogen compounds Chemical class 0.000 claims description 23
- 150000002430 hydrocarbons Chemical group 0.000 claims description 22
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- 238000006731 degradation reaction Methods 0.000 claims description 19
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- 230000006315 carbonylation Effects 0.000 claims description 7
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- 238000007098 aminolysis reaction Methods 0.000 claims description 5
- 238000009901 transfer hydrogenation reaction Methods 0.000 claims description 5
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 4
- 239000012084 conversion product Substances 0.000 claims description 4
- 238000006317 isomerization reaction Methods 0.000 claims description 4
- 125000004437 phosphorous atom Chemical group 0.000 claims description 4
- 230000000087 stabilizing effect Effects 0.000 claims description 4
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- 150000004891 diazines Chemical class 0.000 claims description 3
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 2
- 239000012964 benzotriazole Substances 0.000 claims description 2
- 229940126062 Compound A Drugs 0.000 claims 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims 1
- -1 phosphorus acidic compounds Chemical class 0.000 abstract description 89
- 229910052751 metal Inorganic materials 0.000 description 67
- 239000002184 metal Substances 0.000 description 67
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 40
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- 239000007858 starting material Substances 0.000 description 37
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- 239000000243 solution Substances 0.000 description 19
- 125000003118 aryl group Chemical group 0.000 description 18
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 17
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- 125000000217 alkyl group Chemical group 0.000 description 16
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- 239000000126 substance Substances 0.000 description 15
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 14
- 238000004821 distillation Methods 0.000 description 14
- 150000002739 metals Chemical class 0.000 description 14
- 125000001424 substituent group Chemical group 0.000 description 14
- 241000894007 species Species 0.000 description 13
- 238000000354 decomposition reaction Methods 0.000 description 12
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 12
- 238000005516 engineering process Methods 0.000 description 12
- 125000000962 organic group Chemical group 0.000 description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 11
- 150000003839 salts Chemical class 0.000 description 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 11
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
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- 150000002431 hydrogen Chemical class 0.000 description 8
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- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 7
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- 235000010290 biphenyl Nutrition 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
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- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
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- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
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- ILLOBGFGKYTZRO-UHFFFAOYSA-N tris(2-ethylhexyl) phosphite Chemical compound CCCCC(CC)COP(OCC(CC)CCCC)OCC(CC)CCCC ILLOBGFGKYTZRO-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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Abstract
Description
Claims (1)
- 【特許請求の範囲】 1. 一種以上の燐系酸性化合物、金属−オルガノホスファイトリガンド錯体触 媒及び随意としての遊離オルガノホスファイトリガンドを含有する反応生成物流 体から前記の一種以上の燐系酸性化合物を分離するための方法であって、 前記反応生成物流体から前記の一種以上の燐系酸性化合物を少なくともある程 度の量除去するのに充分な水で前記反応生成物流体を処理することを含む、前記 方法。 2. オルガノホスファイトリガンドを加水分解による分解に対して安定化する ため及び(又は)金属−オルガノホスファイトリガンド錯体触媒を失活に対して 安定化するための方法であって、 金属−オルガノホスファイトリガンド錯体触媒及び随意としての遊離のオルガ ノホスファイトリガンドを含有し且つ一種以上の燐系酸性化合物をもまた含有す る反応生成物流体を、該反応生成物流体から前記の一種以上の燐系酸性化合物を 少なくともある程度の量除去するのに充分な水で処理することを含む、前記方法 。 3. オルガノホスファイトリガンドの加水分解による分解及び(又は)金属− オルガノホスファイトリガンド錯体触媒の失活を防止し且つ(又は)減少させる ための方法であって、 金属−オルガノホスファイトリガンド錯体触媒及び随意としての遊離のオルガ ノホスファイトリガンドを含有し且つ一種以上の燐系酸性化合物をもまた含有す る反応生成物流体を、該反応生成物流体から前記の一種以上の燐系酸性化合物を 少なくともある程度の量除去するのに充分な水で処理することを含む、前記方法 。 4. 金属−オルガノホスファイトリガンド錯体触媒及び随意としての遊離のオ ルガノホスファイトリガンドの存在下で一種以上の反応成分を反応させて一種以 上の製品を含む反応生成物流体を製造することを含む改良型方法であって、 該方法から誘導され且つ該方法の間に生成した燐系酸性化合物をもまた含有す る前記反応生成物流体の少なくとも一部を、該反応生成物流体から前記燐系酸性 化合物を少なくともある程度の量除去するのに充分な水で処理することによって 、前記オルガノホスファイトリガンドの加水分解による分解及び前記金属−オル ガノホスファイトリガンド錯体触媒の失活を防止し且つ(又は)減少させること を含む、前記方法。 5. (i)少なくとも一つの反応帯域中で金属−オルガノホスファイトリガン ド錯体触媒及び随意としての遊離のオルガノホスファイトリガンドの存在下で一 種以上の反応成分を反応させて一種以上の製品を含む反応生成物流体を生成させ 、 (ii)少なくとも一つの分離帯域中又は前記の少なくとも一つの反応帯域中で前 記反応生成物流体から一種以上の製品を分離する ことを含む請求の範囲第4項記載の改良型方法であって、 (a)該方法から誘導され且つ該方法の間に生成した燐系酸性化合物をもまた含 有する前記反応生成物流体の少なくとも一部を、前記の少なくとも一つの反応帯 域又は前記の少なくとも一つの分離帯域から取り出し、 (b)取り出された該方法から誘導され且つ該方法の間に生成した燐系酸性化合 物をもまた含有する反応生成物流体の少なくとも一部を、少なくとも一つのスク ラバー帯域中で、前記反応生成物流体から前記燐系酸性化合物を少なくともある 程度の量除去するのに充分な水で処理し、 (c)処理された反応生成物流体を前記の少なくとも一つの反応帯域又は前記の 少なくとも一つの分離帯域に戻す ことによって、前記オルガノホスファイトリガンドの加水分解による分解及び前 記金属−オルガノホスファイトリガンド錯体触媒の失活を防止し且つ(又は)減 少させることを含む、前記方法。 6. (i)少なくとも一つの反応帯域中で金属−オルガノホスファイトリガン ド錯体触媒及び随意としての遊離のオルガノホスファイトリガンドの存在下で一 種以上の反応成分を反応させて一種以上の製品を含む反応生成物流体を生成させ 、 (ii)少なくとも一つの分離帯域中又は前記の少なくとも一つの反応帯域中で前 記反応生成物流体から一種以上の製品を分離する ことを含む請求の範囲第4項記載の改良型方法であって、 該方法から誘導され且つ該方法の間に生成した燐系酸性化合物をもまた含有す る前記反応生成物流体の少なくとも一部を、該反応生成物流体から前記燐系酸性 化合物を少なくともある程度の量除去するのに充分な水を前記の少なくとも一つ の反応帯域及び(又は)前記の少なくとも一つの分離帯域中に導入することによ って処理することによって、前記オルガノホスファイトリガンドの加水分解によ る分解及び前記金属−オルガノホスファイトリガンド錯体触媒の失活を防止し且 つ(又は)減少させることを含む、前記方法。 7. ヒドロホルミル化、ヒドロアシル化(分子内及び分子間)、ヒドロシアン 化、ヒドロアミド化、ヒドロエステル化、アミノリシス、アルコーリシス、カル ボニル化、異性化又は移動水素化方法を含む、請求の範囲第1〜6項のいずれか に記載の方法。 8. 前記の少なくとも一つの反応帯域中及び(又は)前記の少なくとも一つの 分離帯意中に導入される水が、有機相に加えて別個の水性相又は水相を作るのに 充分な量である、請求の範囲第6項記載の方法。 9. 反応生成物流体から水を分離することをさらに含む、請求の範囲第6項記 載の方法。 10. 接触させる水が2〜7.5のpHを有する、請求の範囲第1〜6項のい ずれかに記載の方法。 11. 工程(b)における処理後の水が一種以上のアルデヒドを含有する、請 求の範囲第5項記載の方法。 12. 工程(b)における処理後の水から前記の一種以上のアルデヒドを回収 し、回収された一種以上のアルデヒドを前記の少なくとも一つの反応帯域又は前 記の少なくとも一つの分離帯域に戻すことをさらに含む、請求の範囲第11項記 載の方法。 13. 前記金属−オルガノホスファイトリガンド錯体触媒が均質又は不均質で ある、請求の範囲第1〜6項のいずれかに記載の方法。 14. 前記反応生成物流体が均質若しくは不均質金属−オルガノホスファイト リガンド錯体触媒を含有し、又は前記反応生成物流体の少なくとも一部が方法の 間に固定不均質金属−オルガノホスファイトリガンド錯体触媒と接触する、請求 の範囲第1〜6項のいずれかに記載の方法。 15. 前記の反応生成物流体からの一種以上の製品の分離を、該方法から誘導 され且つ該方法の間に生成した燐系酸性化合物をもまた含有する反応生成物流体 の少なくとも一部を水で処理する前又は処理した後に行なう、請求の範囲第5又 は6項記載の方法。 16. 燐系酸性化合物を含有する接触後の水を、該燐系酸性化合物を少なくと もある程度の量中和するのに充分な強塩基で処理することをさらに含む、請求の 範囲第1〜6項のいずれかに記載の方法。 17. 前記金属−オルガノホスファイトリガンド錯体触媒が、 (i)次式: (ここで、R1は4〜40個又はそれ以上の炭素原子を有する置換又は非置換三 価炭化水素基を表わす) によって表わされるモノオルガノホスファイト; (ii)次式: (ここで、R2は4〜40個又はそれ以上の炭素原子を有する置換又は非置換二 価炭化水素基を表わし、 Wは1〜18個又はそれ以上の炭素原子を有する置換又は非置換一価炭化水素 基を表わす) によって表わされるジオルガノホスファイト; (iii)次式: (ここで、各R6は同一であっても異なっていてもよく、置換又は非置換一価炭 化水素基を表わす) によって表わされるトリオルガノホスファイト; 及び (iv)次式: (ここで、Xは2〜40個の炭素原子を有する置換又は非置換n価炭化水素橋渡 し基を表わし、 各R7は同一であっても異なっていてもよく、4〜40個の炭素原子を有する 二価炭化水素基を表わし、 各R8は同一であっても異なっていてもよく、1〜24個の炭素原子を有する 置換又は非置換一価炭化水素基を表わし、 a及びbは同一であっても異なっていてもよく、それぞれ0〜6の値を有し、 但しaとbとの合計a+bは2〜6であり、 nはa+bに等しい) によって表わされる2個以上の第三級(三価)燐原子を含有するオルガノポリホ スファイト: から選択されるオルガノホスファイトリガンドと錯化したロジウムを含む、請求 の範囲第1〜6項のいずれかに記載の方法。 18. 反応生成物流体中に存在する燐系酸性化合物をこれもまた前記反応生成 物流体中に存在する有機窒素化合物によって掃去し、且つ、前記燐系酸性化合物 と前記有機窒素化合物との間の反応の転化生成物の燐系酸性化合物の少なくとも ある程度の量をも水処理によって除去する、請求の範囲第1〜6項のいずれかに 記載の方法。 19. 前記有機窒素化合物がジアゾール、トリアゾール、ジアジン及びトリア ジンより成る群から選択される、請求の範囲第18項記載の方法。 20. 有機窒素化合物がベンゾイミダゾール又はベンゾトリアゾールである、 請求の範囲第19項記載の方法。
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US08/753,503 US5786517A (en) | 1995-12-06 | 1996-11-26 | Metal-ligand complex catalyzed processes |
PCT/US1996/019400 WO1997020797A1 (en) | 1995-12-06 | 1996-12-05 | Improved metal-ligand complex catalyzed processes |
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US (1) | US5786517A (ja) |
EP (1) | EP0876321B1 (ja) |
JP (1) | JP4050791B2 (ja) |
CN (1) | CN1078877C (ja) |
AU (1) | AU720764B2 (ja) |
BR (1) | BR9611664A (ja) |
CA (1) | CA2239569C (ja) |
CZ (1) | CZ174998A3 (ja) |
DE (1) | DE69612570T2 (ja) |
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MX (1) | MX206142B (ja) |
PL (1) | PL327107A1 (ja) |
SK (1) | SK68598A3 (ja) |
WO (1) | WO1997020797A1 (ja) |
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JP2008508355A (ja) * | 2004-08-02 | 2008-03-21 | ユニオン・カーバイド・ケミカルズ・アンド・プラスティックス・テクノロジー・コーポレイション | ヒドロホルミル化プロセスの安定化 |
JP2014503492A (ja) * | 2010-11-12 | 2014-02-13 | ダウ テクノロジー インベストメンツ リミティド ライアビリティー カンパニー | 水の添加によるヒドロホルミル化におけるファウリングの緩和 |
JP2017512785A (ja) * | 2014-03-31 | 2017-05-25 | ダウ テクノロジー インベストメンツ リミティド ライアビリティー カンパニー | ヒドロホルミル化プロセス |
JP2018529686A (ja) * | 2015-09-30 | 2018-10-11 | ダウ テクノロジー インベストメンツ リミティド ライアビリティー カンパニー | 有機リン化合物の生成プロセス |
JP2018529685A (ja) * | 2015-09-30 | 2018-10-11 | ダウ テクノロジー インベストメンツ リミティド ライアビリティー カンパニー | 有機リン化合物の生成プロセス |
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DE10349343A1 (de) * | 2003-10-23 | 2005-06-02 | Basf Ag | Stabilisierung von Hydroformylierungskatalysatoren auf Basis von Phosphoramiditliganden |
SA112330271B1 (ar) | 2011-04-18 | 2015-02-09 | داو تكنولوجى انفستمنتس ال ال سى | تخفيف التلوث في عمليات هيدروفورملة عن طريق إضافة الماء |
BR112014016137B1 (pt) | 2011-12-30 | 2021-02-09 | Basf Se | forma cristalina não solvatada, monossolvato de tolueno cristalino, solvato de acetona cristalino, composição, processo para a preparação do monossolvato de tolueno cristalino, processo para a preparação de uma forma cristalina não solvatada, processo para a preparação do solvato de acetona cristalino, método para obter o solvato de acetona cristalino, uso de uma forma cristalina, e, método para produzir um catalisador de metal de transição |
MY164954A (en) | 2011-12-30 | 2018-02-28 | Basf Se | Method for purifying organic diphosphite compounds |
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CN111545247B (zh) * | 2020-03-25 | 2023-06-09 | 华东师范大学 | 一种sba-15负载的多相手性膦金催化剂及其制备方法和应用 |
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1996
- 1996-11-26 US US08/753,503 patent/US5786517A/en not_active Expired - Lifetime
- 1996-12-05 SK SK685-98A patent/SK68598A3/sk unknown
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- 1996-12-05 WO PCT/US1996/019400 patent/WO1997020797A1/en not_active Application Discontinuation
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- 1996-12-05 CN CN96198726A patent/CN1078877C/zh not_active Expired - Lifetime
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2008508355A (ja) * | 2004-08-02 | 2008-03-21 | ユニオン・カーバイド・ケミカルズ・アンド・プラスティックス・テクノロジー・コーポレイション | ヒドロホルミル化プロセスの安定化 |
JP2014503492A (ja) * | 2010-11-12 | 2014-02-13 | ダウ テクノロジー インベストメンツ リミティド ライアビリティー カンパニー | 水の添加によるヒドロホルミル化におけるファウリングの緩和 |
JP2017512785A (ja) * | 2014-03-31 | 2017-05-25 | ダウ テクノロジー インベストメンツ リミティド ライアビリティー カンパニー | ヒドロホルミル化プロセス |
JP2018529686A (ja) * | 2015-09-30 | 2018-10-11 | ダウ テクノロジー インベストメンツ リミティド ライアビリティー カンパニー | 有機リン化合物の生成プロセス |
JP2018529685A (ja) * | 2015-09-30 | 2018-10-11 | ダウ テクノロジー インベストメンツ リミティド ライアビリティー カンパニー | 有機リン化合物の生成プロセス |
Also Published As
Publication number | Publication date |
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DE69612570T2 (de) | 2001-11-15 |
BR9611664A (pt) | 1999-02-23 |
AU1129997A (en) | 1997-06-27 |
EP0876321B1 (en) | 2001-04-18 |
CZ174998A3 (cs) | 1998-11-11 |
WO1997020797A1 (en) | 1997-06-12 |
MX9804493A (es) | 1998-10-31 |
PL327107A1 (en) | 1998-11-23 |
CA2239569C (en) | 2007-06-12 |
DE69612570D1 (de) | 2001-05-23 |
AU720764B2 (en) | 2000-06-08 |
CA2239569A1 (en) | 1997-06-12 |
SK68598A3 (en) | 1999-03-12 |
CN1078877C (zh) | 2002-02-06 |
EA001358B1 (ru) | 2001-02-26 |
US5786517A (en) | 1998-07-28 |
EP0876321A1 (en) | 1998-11-11 |
CN1203575A (zh) | 1998-12-30 |
EA199800524A1 (ru) | 1998-12-24 |
MX206142B (es) | 2002-01-24 |
JP4050791B2 (ja) | 2008-02-20 |
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