JP5536385B2 - 不飽和ポリマー中の炭素−炭素二重結合の連続水素化方法 - Google Patents
不飽和ポリマー中の炭素−炭素二重結合の連続水素化方法 Download PDFInfo
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- JP5536385B2 JP5536385B2 JP2009172454A JP2009172454A JP5536385B2 JP 5536385 B2 JP5536385 B2 JP 5536385B2 JP 2009172454 A JP2009172454 A JP 2009172454A JP 2009172454 A JP2009172454 A JP 2009172454A JP 5536385 B2 JP5536385 B2 JP 5536385B2
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- catalyst
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- rhodium
- hydrogen
- carbon
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- 125000003375 sulfoxide group Chemical group 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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Description
OsQX(CO)(L)(PR3)2
(式中、Qは水素およびフェニルビニル基の1つであってもよく、Xはハロゲン、テトラヒドロボレートおよびアルキル−またはアリール−カルボキシレートの1つであってもよく、Lは酸素分子、ベンゾニトリルまたは配位子なしの1つであってもよく、Rはシクロヘキシル、イソプロピル、第二ブチルおよび第三ブチルの1つであってもよく、前記第三ブチルは1つのRがメチルであるときのみ存在し、但し、QがフェニルビニルであるときにはXはハロゲンであり、Lは配位子なしであり、かつ、Xがアルキル−またはアリール−カルボキシレートであるときにはQは水素であり、Lは配位子なしであり、前記ハロゲンは塩素および臭素から選択される)で表されるオスミウム触媒が特に好適である。好ましくは、Qは水素であり、Xは、塩素、テトラヒドロボレートおよびアセテートから選択され、Lは酸素分子かまたは配位子なしであり、Rはシクロヘキシルまたはイソプロピルである。追加のアルキルまたはアリール−カルボキシレートには、クロロアセテートおよびベンゾエートが含まれる。
(R1 mB)lMXn
(式中、Mはルテニウムまたはロジウムであり、基R1は同一であるかまたは異なり、それぞれC1〜C8アルキル基、C4〜C8シクロアルキル基、C6〜C15アリール基またはC7〜C15アラルキル基であり、Bはリン、ヒ素、硫黄またはスルホキシド基S=Oであり、Xは水素または陰イオン、好ましくはハロゲン、特に好ましくは塩素または臭素であり、lは2、3または4であり、mは2または3であり、nは1、2または3、好ましくは1または3である)の触媒を使用することが可能である。
図5に示したオープン羽根内部構造および形状を有する24の混合要素と1ミリメートル穴のガススパージャとを備えた反応器1を使用して、約38重量パーセントのアクリロニトリル含有率を有するブタジエンアクリロニトリルポリマー(モノクロロベンゼン中の溶液として用いた)を水素化した。分子式OsHCl(CO)[P(シクロヘキシル)3]2のオスミウム系錯体を、モノクロロベンゼン中の溶液の形態で触媒として用いた。水素は、本質的に純粋なガスとして使用した。運転温度および圧力がそれぞれ138℃および3.45MPaである状態で、モノクロロベンゼン中の2.5重量パーセントのポリマー溶液を用い、80μMの触媒を用いた。この連続プロセスで達成された最高水素化度は98%であった。詳細を表Iに示す。
触媒濃度が130μMであることを除いて、実施例1で記載された方法を、表IIIに記載の異なる水素流量、不飽和ポリマーの水素化および運転条件で繰り返した。この場合には、不飽和ポリマーの濃度は、実施例1で使用したポリマーの2倍であり、それ故に液体ホールドアップ(liquid holdup)は少なかった。
Claims (7)
- 溶媒および触媒の存在下において、水素化ニトリルゴムを製造するための、ニトリルゴム中の炭素−炭素二重結合の連続水素化方法であって、前記ニトリルゴム、前記触媒、および水素を、オープン羽根形状を有する静的内部要素を備えた反応器に通す方法。
- 前記触媒が有機金属触媒であり、前記有機金属触媒が、下記式
(R1 mB)lMXn
(式中、Mはルテニウムまたはロジウムであり、R1は同一であるかまたは異なり、且つそれぞれがC1〜C8アルキル基、C4〜C8シクロアルキル基、C6〜C15アリール基またはC7〜C15アラルキル基であり;Bはリン、ヒ素、硫黄、またはスルホキシド基S=Oであり;Xは水素または陰イオンであり;lは2、3または4であり;mは2または3であり;nは1、2または3である)
で表されるロジウムまたはルテニウム含有錯体触媒である、請求項1に記載の方法。 - 前記有機金属触媒が、トリス(トリフェニルホスフィン)ロジウム(I)クロリド、トリス(トリフェニルホスフィン)ロジウム(III)トリクロリド、およびトリス(ジメチルスルホキシド)ロジウム(III)トリクロリド、ならびに式((C 6 H 5 ) 3 P) 4 RhHのテトラキス(トリフェニルホスフィン)ロジウムヒドリド、および前記トリフェニルホスフィンが完全にまたは部分的にトリシクロヘキシルホスフィンで置き換えられたものに相当する化合物からなる群から選択される、請求項1又は2に記載の方法。
- 前記触媒が有機金属触媒であり、前記有機金属触媒が下記式
OsQX(CO)(L)(PR3)2
(式中、Qは水素およびフェニルビニル基の1つであってよく;Xはハロゲン、テトラヒドロボレート、およびアルキル−またはアリール−カルボキシレートの1つであってよく;Lは、酸素分子、ベンゾニトリル、または配位子なしの1つであってもよく;Rはシクロヘキシル、イソプロピル、第二ブチル、および第三ブチルの1つであってよく、前記第三ブチルは1つのRがメチルであるときのみ存在し;但し、QがフェニルビニルであるときにはXはハロゲンであり且つLは配位子なしであり、また、Xがアルキル−またはアリール−カルボキシレートであるときにはQは水素であり且つLは配位子なしであり、前記ハロゲンは塩素および臭素から選択される)
で表されるオスミウム含有触媒である、請求項1に記載の方法。 - 前記式中、Qは水素であり、Xは塩素、テトラヒドロボレート、およびアセテートから選択され、Lは酸素分子であるか又は配位子なしであり、Rはシクロヘキシルまたはイソプロピルである、請求項4に記載の方法。
- 前記ニトリルゴム、前記溶媒、および前記水素が、前記静的内部要素を備えた反応器に送られる前にプレミキサーを通される、請求項1〜5のいずれか一項に記載の方法。
- 前記触媒が、前記プレミキサーに、および/または前記静的内部要素を備えた反応器に加えられる、請求項6に記載の方法。
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EP08161098A EP2147931A1 (en) | 2008-07-24 | 2008-07-24 | Process for the continuous hydrogenation of carbon-carbon double bonds in an unsaturated polymer |
EP08161098.2 | 2008-07-24 |
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JP2010031276A JP2010031276A (ja) | 2010-02-12 |
JP2010031276A5 JP2010031276A5 (ja) | 2012-07-12 |
JP5536385B2 true JP5536385B2 (ja) | 2014-07-02 |
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US (1) | US20100093932A1 (ja) |
EP (2) | EP2147931A1 (ja) |
JP (1) | JP5536385B2 (ja) |
KR (1) | KR20100011930A (ja) |
CN (1) | CN101633714A (ja) |
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EP2289947A1 (en) * | 2009-08-26 | 2011-03-02 | University Of Waterloo | Nano-sized hydrogenated diene-based latex particles |
DE102010019771A1 (de) * | 2010-05-07 | 2011-11-10 | Dürr Systems GmbH | Zerstäuber mit einem Gittermischer |
TWI617352B (zh) * | 2012-12-25 | 2018-03-11 | 南帝化學工業股份有限公司 | 催化劑組成物及使用該組成物之不飽合共聚物之氫化方法 |
CN103333290B (zh) * | 2013-07-23 | 2015-09-30 | 蒲城瑞鹰新材料科技有限公司 | 一种氢化丁腈橡胶的微通道反应器连续生产工艺 |
TWI649335B (zh) * | 2013-12-30 | 2019-02-01 | 德商艾朗希歐德意志有限公司 | 含酚之氫化腈橡膠 |
CN112142883B (zh) * | 2019-06-28 | 2022-06-07 | 沈阳化工研究院有限公司 | 一种共轭二烯烃聚合物连续加氢方法及装置 |
KR102454095B1 (ko) | 2020-10-30 | 2022-10-14 | 한국과학기술연구원 | 액상유기물수소운반체를 이용한 연속식 수소저장장치 |
CN115106029B (zh) * | 2022-06-10 | 2023-11-03 | 九江捷豹药械有限公司 | 一种消毒凝胶的制备装置 |
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DE3529252A1 (de) | 1985-08-16 | 1987-02-19 | Bayer Ag | Verfahren zur selektiven hydrierung ungesaettigter verbindungen |
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US7666950B2 (en) * | 2006-06-01 | 2010-02-23 | Lanxess Deutschland Gmbh | Process for preparing hydrogenated nitrile rubbers |
TW200842132A (en) * | 2007-04-20 | 2008-11-01 | Chi Mei Corp | Apparatus for hydrogenation and method for hydrogenating conjugated diene polymer by employing the apparatus |
-
2008
- 2008-07-24 EP EP08161098A patent/EP2147931A1/en not_active Withdrawn
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2009
- 2009-07-17 CA CA2672634A patent/CA2672634A1/en not_active Abandoned
- 2009-07-21 US US12/506,528 patent/US20100093932A1/en not_active Abandoned
- 2009-07-22 EP EP09166071A patent/EP2151455B1/en not_active Not-in-force
- 2009-07-23 JP JP2009172454A patent/JP5536385B2/ja not_active Expired - Fee Related
- 2009-07-23 BR BRPI0919182-8A patent/BRPI0919182A2/pt not_active IP Right Cessation
- 2009-07-23 KR KR1020090067287A patent/KR20100011930A/ko not_active IP Right Cessation
- 2009-07-23 TW TW098124800A patent/TW201016727A/zh unknown
- 2009-07-24 CN CN200910160830A patent/CN101633714A/zh active Pending
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KR20100011930A (ko) | 2010-02-03 |
CA2672634A1 (en) | 2010-01-24 |
EP2147931A1 (en) | 2010-01-27 |
BRPI0919182A2 (pt) | 2012-07-31 |
CN101633714A (zh) | 2010-01-27 |
EP2151455B1 (en) | 2012-11-14 |
EP2151455A1 (en) | 2010-02-10 |
JP2010031276A (ja) | 2010-02-12 |
US20100093932A1 (en) | 2010-04-15 |
TW201016727A (en) | 2010-05-01 |
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