RU2000106067A - METHOD FOR PRODUCING MIXTURES OF MONOOLEPHIN MONONITRILES WITH FIVE FUNCTIONS OF CARBON CARBON BY CATALYTIC HYDROCYANATION IN THE PRESENCE OF A CATALYST CONTAINING AT LEAST ONE FINE AND SMALL FILTER) - Google Patents
METHOD FOR PRODUCING MIXTURES OF MONOOLEPHIN MONONITRILES WITH FIVE FUNCTIONS OF CARBON CARBON BY CATALYTIC HYDROCYANATION IN THE PRESENCE OF A CATALYST CONTAINING AT LEAST ONE FINE AND SMALL FILTER)Info
- Publication number
- RU2000106067A RU2000106067A RU2000106067/04A RU2000106067A RU2000106067A RU 2000106067 A RU2000106067 A RU 2000106067A RU 2000106067/04 A RU2000106067/04 A RU 2000106067/04A RU 2000106067 A RU2000106067 A RU 2000106067A RU 2000106067 A RU2000106067 A RU 2000106067A
- Authority
- RU
- Russia
- Prior art keywords
- formula
- hydrocyanation
- mixture
- mononitriles
- carbon
- Prior art date
Links
- 238000005669 hydrocyanation reaction Methods 0.000 title claims 11
- 239000000203 mixture Substances 0.000 title claims 11
- 239000003054 catalyst Substances 0.000 title claims 9
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 title claims 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 title claims 2
- 230000003197 catalytic Effects 0.000 title claims 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 230000027455 binding Effects 0.000 claims 7
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims 6
- 125000004432 carbon atoms Chemical group C* 0.000 claims 6
- 239000003446 ligand Substances 0.000 claims 6
- 150000002430 hydrocarbons Chemical class 0.000 claims 5
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 5
- 150000005673 monoalkenes Chemical class 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 4
- 238000006317 isomerization reaction Methods 0.000 claims 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 4
- -1 1,3-butadiene hydrocarbons Chemical class 0.000 claims 3
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 3
- OAICVXFJPJFONN-UHFFFAOYSA-N phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 3
- 229910052698 phosphorus Inorganic materials 0.000 claims 3
- 239000011574 phosphorus Substances 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- BTGRAWJCKBQKAO-UHFFFAOYSA-N Adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 claims 2
- 150000001336 alkenes Chemical class 0.000 claims 2
- 229910052742 iron Inorganic materials 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 229910052759 nickel Inorganic materials 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 125000004430 oxygen atoms Chemical group O* 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (Z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 claims 1
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-Bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 claims 1
- WBAXCOMEMKANRN-UHFFFAOYSA-N 2-methylbut-3-enenitrile Chemical compound C=CC(C)C#N WBAXCOMEMKANRN-UHFFFAOYSA-N 0.000 claims 1
- 229940045714 Alkyl sulfonate alkylating agents Drugs 0.000 claims 1
- 241000554155 Andes Species 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- KTWOOEGAPBSYNW-UHFFFAOYSA-N Ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 claims 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N Phosphite Chemical compound [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims 1
- WKFBZNUBXWCCHG-UHFFFAOYSA-N Phosphorus trifluoride Chemical compound FP(F)F WKFBZNUBXWCCHG-UHFFFAOYSA-N 0.000 claims 1
- 239000005092 Ruthenium Substances 0.000 claims 1
- 210000003371 Toes Anatomy 0.000 claims 1
- 150000008052 alkyl sulfonates Chemical class 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- 125000005228 aryl sulfonate group Chemical group 0.000 claims 1
- 125000004429 atoms Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 150000007942 carboxylates Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 229910052804 chromium Inorganic materials 0.000 claims 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims 1
- 239000011651 chromium Substances 0.000 claims 1
- 229910052803 cobalt Inorganic materials 0.000 claims 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims 1
- 239000010941 cobalt Substances 0.000 claims 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 1
- 150000001925 cycloalkenes Chemical class 0.000 claims 1
- LPBBEMRSRONKMN-UHFFFAOYSA-N cyclopentyl-di(propan-2-yl)phosphane;iron Chemical compound [Fe].CC(C)P(C(C)C)[C]1[CH][CH][CH][CH]1.CC(C)P(C(C)C)[C]1[CH][CH][CH][CH]1 LPBBEMRSRONKMN-UHFFFAOYSA-N 0.000 claims 1
- 150000001993 dienes Chemical class 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- 235000019525 fullness Nutrition 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 125000005842 heteroatoms Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- KLGZELKXQMTEMM-UHFFFAOYSA-N hydride Chemical compound [H-] KLGZELKXQMTEMM-UHFFFAOYSA-N 0.000 claims 1
- 238000011065 in-situ storage Methods 0.000 claims 1
- 229910052738 indium Inorganic materials 0.000 claims 1
- PWHULOQIROXLJO-UHFFFAOYSA-N manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims 1
- 229910052748 manganese Inorganic materials 0.000 claims 1
- 239000011572 manganese Substances 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 229910052762 osmium Inorganic materials 0.000 claims 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical group O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 1
- YWUKEFWDPYXDHH-UHFFFAOYSA-N phosphinite Chemical compound [PH2-]=O YWUKEFWDPYXDHH-UHFFFAOYSA-N 0.000 claims 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 1
- 238000007670 refining Methods 0.000 claims 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims 1
- 229910052703 rhodium Inorganic materials 0.000 claims 1
- 239000010948 rhodium Substances 0.000 claims 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims 1
- 229910052707 ruthenium Inorganic materials 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000011780 sodium chloride Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 239000011593 sulfur Chemical group 0.000 claims 1
- 229910052717 sulfur Chemical group 0.000 claims 1
- 230000001131 transforming Effects 0.000 claims 1
- 229910052720 vanadium Inorganic materials 0.000 claims 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium(0) Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims 1
Claims (19)
где R1 означает остаток формулы РL2, причем остатки L могут быть одинаковыми или разными и означают алкил, циклоалкил или арил;
R1′ означает атом водорода, алкил или остаток формулы PL2, причем остатки L имеют вышеуказанное значение;
R2,R2′,R3,R3′,R4,R4′,R5,R5′, независимо друг от друга, выбирают из группы, состоящей из атома водорода, циклоалкила, арила или алкила, который может быть прерван атомом кислорода или может быть замещен остатком формулы NE1E2, причем Е1 и Е2 могут быть одинаковыми или разными и означают алкил, циклоалкил или арил, или, смотря по обстоятельствам, два из заместителей R2, R3, R4, R5 и/или R2′,R3′,R4′,R5′ в соседних положениях вместе со связывающей их частью циклодентадиенильного кольца могут образовывать ароматический или неароматический от пяти- до семичленного карбоцикл или гетероцикл, который может включать один, два или три гетероатома, выбираемых из группы, состоящей из кислорода, азота и серы;
М означает атом железа, кобальта, никеля, рутения, осмия, родия, марганца, хрома или ванадия;
или их соли и смеси.1. A method of obtaining mixtures of monoolefin mononitriles with 5 carbon atoms, including non-conjugated double carbon-carbon and triple carbon-nitrogen bonds, by catalytic hydrocyanation of 1,3-butadiene or a mixture of 1,3-butadiene hydrocarbons, characterized in that the hydrocyanation is carried out a the presence of a catalyst containing at least one metallocene complex with trivalent phosphorus and zero valence nickel, including at least one monodentate or bidentate metallocene Andes with trivalent phosphorus of general formula (I)
where R 1 means the remainder of the formula PL 2 , and the residues L may be the same or different and mean alkyl, cycloalkyl or aryl;
R 1 ′ represents a hydrogen atom, an alkyl or a residue of the formula PL 2 , wherein the residues L have the above meaning;
R 2 , R 2 ′ , R 3 , R 3 ′ , R 4 , R 4 ′ , R 5 , R 5 ′ , independently of one another, are selected from the group consisting of a hydrogen atom, cycloalkyl, aryl or alkyl, which may be interrupted by an oxygen atom or may be substituted by a residue of the formula NE 1 E 2 , wherein E 1 and E 2 may be the same or different and mean alkyl, cycloalkyl or aryl, or, as the case may be, two of the substituents R 2 , R 3 , R 4, R 5, and ', R 5' in adjacent positions / or R 2 ', R 3', R 4 together with their binding part tsiklodentadienilnogo ring may form an aromatic or nonaromatic of toe - to seven-membered carbocycle or heterocycle which may contain one, two or three heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur;
M means an atom of iron, cobalt, nickel, ruthenium, osmium, rhodium, manganese, chromium or vanadium;
or their salts and mixtures.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19733682.5 | 1997-08-04 | ||
DE19733682A DE19733682A1 (en) | 1997-08-04 | 1997-08-04 | A process for the preparation of mixtures of monoolefinic C¶5¶ mononitriles by catalytic hydrocyanation in the presence of a catalyst comprising at least one metallocene phosphorus (III) nickel (0) complex |
Publications (2)
Publication Number | Publication Date |
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RU2000106067A true RU2000106067A (en) | 2001-11-27 |
RU2228329C2 RU2228329C2 (en) | 2004-05-10 |
Family
ID=7837954
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
RU2000106067/04A RU2228329C2 (en) | 1997-08-04 | 1998-08-04 | Method for preparing mixtures of monoolefinic mononitriles |
Country Status (17)
Country | Link |
---|---|
US (1) | US6169198B1 (en) |
EP (1) | EP1003716B1 (en) |
JP (1) | JP2001513528A (en) |
KR (1) | KR20010022579A (en) |
CN (1) | CN1266424A (en) |
AR (1) | AR010428A1 (en) |
AU (1) | AU9257098A (en) |
BR (1) | BR9810978A (en) |
CA (1) | CA2298585A1 (en) |
DE (2) | DE19733682A1 (en) |
ES (1) | ES2216308T3 (en) |
ID (1) | ID24307A (en) |
MY (1) | MY126401A (en) |
RU (1) | RU2228329C2 (en) |
TR (1) | TR200000327T2 (en) |
TW (1) | TW466221B (en) |
WO (1) | WO1999007671A1 (en) |
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DE10136488A1 (en) * | 2001-07-27 | 2003-02-06 | Basf Ag | Catalyst system comprising Ni(0) and phosphorous ligands is useful for the production of nitrile and dinitrile compounds |
EP1344770A1 (en) * | 2002-03-12 | 2003-09-17 | E.I. du Pont de Nemours and Company | Process for the hydrocyanation of butadiene |
FR2850966B1 (en) | 2003-02-10 | 2005-03-18 | Rhodia Polyamide Intermediates | PROCESS FOR PRODUCING DINITRIL COMPOUNDS |
FR2854891B1 (en) | 2003-05-12 | 2006-07-07 | Rhodia Polyamide Intermediates | PROCESS FOR PREPARING DINITRILES |
DE102004004721A1 (en) | 2004-01-29 | 2005-08-18 | Basf Ag | Process for the separation of pentenenitrile isomers |
DE102004004672A1 (en) * | 2004-01-29 | 2005-08-18 | Basf Ag | Hydrocyanation process |
DE102004004718A1 (en) * | 2004-01-29 | 2005-08-18 | Basf Ag | Hydrocyanation process |
DE102004004682A1 (en) * | 2004-01-29 | 2005-08-18 | Basf Ag | Process for the preparation of adiponitrile by hydrocyanation of 1,3-butadiene |
DE102004004697A1 (en) | 2004-01-29 | 2005-08-18 | Basf Ag | Process for the preparation of pentenenitriles from n-butane |
EP1716105B1 (en) | 2004-01-29 | 2011-04-27 | Basf Se | Method for producing linear pentenenitrile |
DE102004004696A1 (en) * | 2004-01-29 | 2005-08-18 | Basf Ag | Continuous process for the preparation of linear pentenenitriles |
DE102004004673A1 (en) | 2004-01-29 | 2005-08-18 | Basf Ag | Process for the hydrocyanation of butadiene |
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EP2322503B1 (en) * | 2005-10-18 | 2014-12-31 | Invista Technologies S.à.r.l. | Process of making 3-aminopentanenitrile |
WO2007081987A2 (en) | 2006-01-10 | 2007-07-19 | Elevance Renewable Sciences, Inc. | Method of making hydrogenated metathesis products |
US8888908B2 (en) * | 2006-03-07 | 2014-11-18 | Elevance Renewable Sciences, Inc. | Colorant compositions comprising metathesized unsaturated polyol esters |
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US7880028B2 (en) * | 2006-07-14 | 2011-02-01 | Invista North America S.A R.L. | Process for making 3-pentenenitrile by hydrocyanation of butadiene |
US7709673B2 (en) * | 2006-07-14 | 2010-05-04 | Invista North America S.A R.L. | Process for making 3-pentenenitrile by hydrocyanation of butadiene |
WO2008048520A2 (en) * | 2006-10-13 | 2008-04-24 | Elevance Renewable Sciences, Inc. | Methods of making organic compounds by metathesis and hydrocyanation |
EP2121546B1 (en) * | 2006-10-13 | 2017-12-13 | Elevance Renewable Sciences, Inc. | Methods of making alpha, omega-dicarboxylic acid alkene derivatives by metathesis |
WO2008046106A2 (en) | 2006-10-13 | 2008-04-17 | Elevance Renewable Sciences, Inc. | Synthesis of terminal alkenes from internal alkenes via olefin metathesis |
US8906334B2 (en) | 2007-05-14 | 2014-12-09 | Invista North America S.A R.L. | High efficiency reactor and process |
US8101790B2 (en) | 2007-06-13 | 2012-01-24 | Invista North America S.A.R.L. | Process for improving adiponitrile quality |
WO2009091771A2 (en) | 2008-01-15 | 2009-07-23 | Invista Technologies S.A R.L | Process for making and refining 3-pentenenitrile, and for refining 2-methyl-3-butenenitrile |
CN101918356B (en) | 2008-01-15 | 2013-09-25 | 因温斯特技术公司 | Hydrocyanation of pentenenitriles |
JP2011515411A (en) * | 2008-03-19 | 2011-05-19 | インビスタ テクノロジーズ エス エイ アール エル | Method for producing cyclododecatriene and method for producing laurolactone |
KR101610423B1 (en) | 2008-10-14 | 2016-04-08 | 인비스타 테크놀러지스 에스.에이 알.엘. | Process for making 2-secondary-alkyl-4,5-di-(normal-alkyl)phenols |
FR2937321B1 (en) * | 2008-10-21 | 2010-10-22 | Rhodia Operations | PROCESS FOR PRODUCING COMPOUNDS COMPRISING NITRIL FUNCTIONS |
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CN103080075B (en) | 2010-07-07 | 2014-10-29 | 因温斯特技术公司 | Process for making nitriles |
CN103080119B (en) | 2010-09-07 | 2015-04-08 | 因温斯特技术公司 | Nickel compositions for preparing nickel metal and nickel complexes |
WO2013181095A1 (en) | 2012-06-01 | 2013-12-05 | Invista North America S.A R.L. | Stable ligand mixtures and processes for making same |
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CN108997167B (en) * | 2018-08-09 | 2021-05-07 | 大连微凯化学有限公司 | Method for preparing adiponitrile and methylglutaronitrile by hydrocyanation of butadiene |
CN114105817B (en) * | 2021-12-10 | 2022-10-28 | 北京道思克矿山装备技术有限公司 | Method for continuously preparing adiponitrile by 1,3-butadiene hydrocyanation |
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Publication number | Priority date | Publication date | Assignee | Title |
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US4714773A (en) * | 1987-01-09 | 1987-12-22 | E. I. Du Pont De Nemours And Company | Hydrocyanation of butadiene |
BE1008343A3 (en) | 1994-05-06 | 1996-04-02 | Dsm Nv | Bidentate phosphine ligand |
-
1997
- 1997-08-04 DE DE19733682A patent/DE19733682A1/en not_active Withdrawn
-
1998
- 1998-07-31 AR ARP980103803A patent/AR010428A1/en unknown
- 1998-08-03 TW TW087112745A patent/TW466221B/en not_active IP Right Cessation
- 1998-08-04 DE DE59810804T patent/DE59810804D1/en not_active Expired - Fee Related
- 1998-08-04 CA CA002298585A patent/CA2298585A1/en not_active Abandoned
- 1998-08-04 JP JP2000507207A patent/JP2001513528A/en not_active Withdrawn
- 1998-08-04 AU AU92570/98A patent/AU9257098A/en not_active Abandoned
- 1998-08-04 ES ES98945143T patent/ES2216308T3/en not_active Expired - Lifetime
- 1998-08-04 BR BR9810978-2A patent/BR9810978A/en not_active IP Right Cessation
- 1998-08-04 MY MYPI98003554A patent/MY126401A/en unknown
- 1998-08-04 TR TR2000/00327T patent/TR200000327T2/en unknown
- 1998-08-04 US US09/463,820 patent/US6169198B1/en not_active Expired - Fee Related
- 1998-08-04 CN CN98807985A patent/CN1266424A/en active Pending
- 1998-08-04 EP EP98945143A patent/EP1003716B1/en not_active Expired - Lifetime
- 1998-08-04 ID IDW20000229A patent/ID24307A/en unknown
- 1998-08-04 KR KR1020007001170A patent/KR20010022579A/en not_active Application Discontinuation
- 1998-08-04 RU RU2000106067/04A patent/RU2228329C2/en not_active IP Right Cessation
- 1998-08-04 WO PCT/EP1998/004851 patent/WO1999007671A1/en not_active Application Discontinuation
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