WO1999051344A1 - Alkylidenkomplexe des rutheniums mit n-heterozyklischen carbenliganden; verwendung als hochaktive, selektive katalysatoren für die olefin-metathese - Google Patents
Alkylidenkomplexe des rutheniums mit n-heterozyklischen carbenliganden; verwendung als hochaktive, selektive katalysatoren für die olefin-metathese Download PDFInfo
- Publication number
- WO1999051344A1 WO1999051344A1 PCT/EP1999/001785 EP9901785W WO9951344A1 WO 1999051344 A1 WO1999051344 A1 WO 1999051344A1 EP 9901785 W EP9901785 W EP 9901785W WO 9951344 A1 WO9951344 A1 WO 9951344A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- carbon atoms
- radicals
- hydrogen
- cyclic
- groups
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
- C07F15/0046—Ruthenium compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2265—Carbenes or carbynes, i.e.(image)
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2265—Carbenes or carbynes, i.e.(image)
- B01J31/2269—Heterocyclic carbenes
- B01J31/2273—Heterocyclic carbenes with only nitrogen as heteroatomic ring members, e.g. 1,3-diarylimidazoline-2-ylidenes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
- C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
- C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
- C07C2/08—Catalytic processes
- C07C2/26—Catalytic processes with hydrides or organic compounds
- C07C2/32—Catalytic processes with hydrides or organic compounds as complexes, e.g. acetyl-acetonates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C6/00—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions
- C07C6/02—Metathesis reactions at an unsaturated carbon-to-carbon bond
- C07C6/04—Metathesis reactions at an unsaturated carbon-to-carbon bond at a carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/313—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of doubly bound oxygen containing functional groups, e.g. carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/475—Preparation of carboxylic acid esters by splitting of carbon-to-carbon bonds and redistribution, e.g. disproportionation or migration of groups between different molecules
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
- C08G61/04—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms
- C08G61/06—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds
- C08G61/08—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds of carbocyclic compounds containing one or more carbon-to-carbon double bonds in the ring
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/10—Polymerisation reactions involving at least dual use catalysts, e.g. for both oligomerisation and polymerisation
- B01J2231/14—Other (co) polymerisation, e.g. of lactides, epoxides
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/50—Redistribution or isomerisation reactions of C-C, C=C or C-C triple bonds
- B01J2231/54—Metathesis reactions, e.g. olefin metathesis
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/50—Redistribution or isomerisation reactions of C-C, C=C or C-C triple bonds
- B01J2231/54—Metathesis reactions, e.g. olefin metathesis
- B01J2231/543—Metathesis reactions, e.g. olefin metathesis alkene metathesis
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
- B01J2531/0261—Complexes comprising ligands with non-tetrahedral chirality
- B01J2531/0263—Planar chiral ligands, e.g. derived from donor-substituted paracyclophanes and metallocenes or from substituted arenes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/821—Ruthenium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- C07C2531/22—Organic complexes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- C07C2531/24—Phosphines
Definitions
- the invention relates to alkylidene complex compounds of ruthenium with N-heterocyclic carbene ligands and a process for the preparation of olefins by olefin metathesis from acyclic olefins with two or more carbon atoms or / and from cyclic olefins with four or more carbon atoms, at least one of these alkylidene complex compounds being used as a catalyst becomes.
- olefin metathesis is an essential component since by this reaction olefins can be synthesized without by-products.
- the olefin metathesis not only has great potential in the field of preparative, organic synthesis (RCM, ethenolysis, metathesis of acyclic olefins), but also in polymer chemistry (ROMP, ADMET, alkyne polymerization). Since its discovery in the 1950s, several large-scale processes have been implemented. Nevertheless, olefin metathesis has only recently become a broadly applicable synthesis method through the discovery of new catalysts (JC Mol in: B.
- the task was to develop tailor-made metathesis catalysts which, in addition to a high tolerance towards functional groups, are distinguished by a variable ligand sphere and which fine-tune the catalyst for specific properties of different types
- X 1 and X 2 represent an anionic ligand in which R 1 and R 2 are identical or different from one another, but can also have a cycle in which R 1 and R 2 are hydrogen or / and represent a hydrocarbon group, the hydrocarbon groups being the same or different from one another, straight-chain, branched, cyclic or / and non-cyclic radicals from the group consisting of alkyl radicals with 1 to 50 carbon atoms, alkenyl radicals with 1 to 50 carbon atoms, alkynyl radicals with 1 to 50 carbon atoms, Aryl radicals with 1 to 30 carbon atoms and silyl radicals exist, the hydrogen atoms in the hydrocarbon and / or silyl groups being partially or wholly by an alkyl, aryl, alkenyl, alkynyl, metallocenyl, Halogen, nitro, nitroso, hydroxy, alkoxy, aryloxy, amino, amido, carboxy, carbonyl
- R 1 , R 2 , R 3 and R 4 in the formulas II, III, IV and V are identical or different and represent hydrogen or / and hydrocarbon groups, the hydrocarbon groups being the same or different, cyclic, non-cyclic, straight-chain or / and branched residues from the group of alkyl residues with 1 to 50 carbon atoms, alkenyl residues with 1 to 50
- the alkyl radicals, alkenyl radicals or alkynyl radicals in the formulas I to V preferably have 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms.
- the complex compounds according to the invention are highly active catalysts for olefin metathesis. They are particularly inexpensive.
- the olefin metathesis with the catalysts according to the invention is characterized not only by a high tolerance towards a wide variety of functional groups but also by its variety in the ligand sphere. By varying the easily accessible N-heterocyclic carbene ligands, activity and selectivity can be controlled in a targeted manner, and chirality can also be introduced in a simple manner.
- anionic ligands X 1 and X 2 are preferably those according to the invention.
- Isocyanate, thiocyanate and isothiocyanate are preferred.
- the hydrogen in the hydrocarbon groups R 1 , R 2 , R 3 and R 4 can be partially or completely replaced by halogen, nitro, nitroso, hydroxyl, alkoxy, aryloxy, Amino, amido, carboxy, carbonyl,
- R 3 and R 4 can represent a fused ring system.
- the ligands L 1 and L 2 of the complex compound of the general structural formula I can a chelating ligand of the general formula VI
- Alkoxy, aryloxy, amino, amido, carboxy, carbonyl, thio or / and sulfonyl groups preferably by alkyl, aryl or / and metallocenyl groups, can be substituted one or more times, identically or independently of one another.
- the ligands of the general formulas II, IM, IV, V or / and VI can have central, axial and / or planar chirality.
- R 1 to R 2 are preferably hydrogen, substituted or / and unsubstituted alkyl, alkenyl or / and aryl radicals, X 1 and X 2 are preferably halide, alkoxide and / or carboxylate ions and L 1 and L 2 are preferred for an N-heterocyclic carbene of the general formula II.
- the complexes are usually synthesized by ligand substitution of corresponding phosphine complexes. According to reaction equation (1), these can be selectively substituted twice or simply according to reaction equation (2). In the case of simple substitution, the second phosphine can be selectively replaced by another electron donor, e.g. B. pyridine, phosphine, N-heterocycle carbene, phosphite, stibine, arsine are substituted accordingly
- another electron donor e.g. B. pyridine, phosphine, N-heterocycle carbene, phosphite, stibine, arsine are substituted accordingly
- this invention also encompasses the processes of all olefin metathesis reactions such as ring opening metathesis polymerization (ROMP), metathesis acyclic olefins, ethenolysis, ring closure metathesis (RCM), acyclic diene metathesis polymerization (ADMET) and depolymerization of olefinic polymers.
- ring opening metathesis polymerization (ROMP)
- metathesis acyclic olefins ethenolysis
- RCM ring closure metathesis
- ADMET acyclic diene metathesis polymerization
- depolymerization of olefinic polymers depolymerization of olefinic polymers.
- functional groups in particular groups of alcohols, amines, thiols, ketones, aldehydes, carboxylic acids, esters, amides, ethers, silanes,
- Sulfides and halogens allow the presence of such functional groups during the metathesis reaction.
- the object is further achieved by a process for the preparation of acyclic olefins having two or more carbon atoms and / or of cyclic olefins having four or more carbon atoms, each in accordance with the general formula
- VII VII from acyclic olefins with two or more carbon atoms and / or from cyclic olefins with four or more carbon atoms, each in accordance with the general formula VII, by olefin metathesis reaction in the presence of at least one catalyst, which is characterized in that a catalyst after a of claims 1 to 7 is used and that R ' ⁇ R' 2 , R ' 3 and R' 4 in the general formula VII for hydrogen or / and
- hydrocarbon groups the hydrocarbon group consisting of identical or independently different straight-chain, branched, cyclic or / and non-cyclic radicals from the group of alkyl radicals with 1 to 50 carbon atoms, alkenyl radicals with 1 to 50 carbon atoms, alkynyl radicals with 1 to 50
- Metallocenyl groups are single or multiple, the same or different from each other.
- the olefins used preferably contain one or more double bonds.
- R ' 1 , R' 2 , R ' 3 and R' 4 form a cycle in the olefins of the general formula VII to be prepared in pairs, once or several times, identically or independently of one another.
- the hydrogen in the hydrocarbon groups R ' ⁇ R' 2 , R ' 3 and R' 4 is partly or wholly by halogen, silyl, nitro, nitroso, hydroxyl, alkoxy , Aryloxy, amino, amido, carboxy, carbonyl, thio, sulfonyl or / and metallocenyl groups are replaced one or more times, identically or independently of one another.
- the process can be carried out with or without a solvent, but preferably with organic solvents.
- the process according to the invention can preferably be carried out with the addition of a Brönstedt acid, preferably HCl, HBr, HI, HBF 4 , HPF 6 or / and
- Trifluoroacetic acid or / and with the addition of a Lewis acid, preferably of BF 3 , AICI 3 and / or Znl 2 , are carried out.
- NCH 1 19.9 and 1 18.9
- NCH 56.7, 56.1, 55.0 and 54.7
- NCHMeNaph 24.7, 24.3, 21 .0 and 20.0
- NCHMeNaph 1 19.9 and 1 18.9
- Examples include norbornene, cyclooctene and functionalized
- Formula VIII illustrates the basic structure of the norbornene derivatives used in Table 2.
- Typical reaction mixture for the metathesis of 1-octene 49 ⁇ l (0.31 mmol) of 1-octene were added to a solution of 3.6 mg (6.3 ⁇ mol) 1_ in 2 ml dichloroethane, and the reaction mixture was placed in a 60 ° C. oil bath. After 3 h the reaction mixture was analyzed by GC / MS.
- the selectivity indicates the proportion of 7-tetradecene compared to other metathetic products
- 6-tridecene was obtained as the most common by-product in addition to 7-tetradecene and 6-dodecene, 1-heptene and 2-nonen in small quantities.
- the product distribution is strongly dependent on the catalyst used. In the case of 2, 7-tetradecene was obtained almost selectively; on the other hand, the more active complex 1_ only delivered 7-tetradecene with a selectivity of 63% at high conversion.
- essentially 6-tridecene was obtained from the cross-metathesis of 1-octene with 2-octene.
Abstract
Description
Claims
Priority Applications (11)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IL13859599A IL138595A (en) | 1998-04-06 | 1999-03-18 | Alkylidene complexes of ruthenium with n-heterocyclic carbene ligands and their use as highly active, selective catalysts for olefin metathesis |
DE59912097T DE59912097D1 (de) | 1998-04-06 | 1999-03-18 | Alkylidenkomplexe des rutheniums mit n-heterozyklischen carbenliganden; verwendung als katalysatoren für die olefin-metathese |
EP99910357A EP1087838B1 (de) | 1998-04-06 | 1999-03-18 | Alkylidenkomplexe des rutheniums mit n-heterozyklischen carbenliganden; verwendung als katalysatoren für die olefin-metathese |
JP2000542103A JP4531253B2 (ja) | 1998-04-06 | 1999-03-18 | N−複素環式カルベン配位子を含むルテニウムのアルキリデン錯体;オレフィンメタセシス用の高活性選択性触媒としての使用 |
US09/647,742 US6635768B1 (en) | 1998-04-06 | 1999-03-18 | Alkylidene complexes of ruthenium containing N-heterocyclic carbene ligands; use as highly active, selective catalysts for olefin metathesis |
US10/630,552 US7294717B2 (en) | 1998-04-06 | 2003-07-29 | Alkylidene complexes of ruthenium containing N-heterocyclic carbene ligands; use as highly active, selective catalysts for olefin metathesis |
US11/021,967 US7652145B2 (en) | 1998-04-06 | 2004-12-23 | Alkylidene complexes of ruthenium containing N-heterocyclic carbene ligands; use as highly active, selective catalysts for olefin metathesis |
US11/828,828 US7378528B2 (en) | 1998-04-06 | 2007-07-26 | Alkylidene complexes of ruthenium containing N-heterocyclic carbene ligands; use as highly active, selective catalysts for olefin metathesis |
US12/115,139 US20080207911A1 (en) | 1998-04-06 | 2008-05-05 | Alkylidene complexes of ruthenium containing n-heterocyclic carbene ligands; use as highly active, selective catalysts for olefin metathesis |
US13/090,688 US8153810B2 (en) | 1998-04-06 | 2011-04-20 | Alkylidene complexes of ruthenium containing N-heterocyclic carbene ligands; use as highly active, selective catalysts for olefin metathesis |
US14/193,785 US20150038723A1 (en) | 1998-04-06 | 2014-02-28 | Alkylidene complexes of ruthenium containing n-heterocyclic carbene ligands; use as highly active, selective catalysts for olefin metathesis |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19815275A DE19815275B4 (de) | 1998-04-06 | 1998-04-06 | Alkylidenkomplexe des Rutheniums mit N-heterozyklischen Carbenliganden und deren Verwendung als hochaktive, selektive Katalysatoren für die Olefin-Metathese |
DE19815275.2 | 1998-04-06 |
Related Child Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US09/647,742 A-371-Of-International US6635768B1 (en) | 1998-04-06 | 1999-03-18 | Alkylidene complexes of ruthenium containing N-heterocyclic carbene ligands; use as highly active, selective catalysts for olefin metathesis |
US09647742 A-371-Of-International | 1999-03-18 | ||
US10/630,552 Division US7294717B2 (en) | 1998-04-06 | 2003-07-29 | Alkylidene complexes of ruthenium containing N-heterocyclic carbene ligands; use as highly active, selective catalysts for olefin metathesis |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1999051344A1 true WO1999051344A1 (de) | 1999-10-14 |
Family
ID=7863687
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1999/001785 WO1999051344A1 (de) | 1998-04-06 | 1999-03-18 | Alkylidenkomplexe des rutheniums mit n-heterozyklischen carbenliganden; verwendung als hochaktive, selektive katalysatoren für die olefin-metathese |
Country Status (6)
Country | Link |
---|---|
US (7) | US6635768B1 (de) |
EP (1) | EP1087838B1 (de) |
JP (1) | JP4531253B2 (de) |
DE (2) | DE19815275B4 (de) |
IL (1) | IL138595A (de) |
WO (1) | WO1999051344A1 (de) |
Cited By (43)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2000058322A1 (en) * | 1999-03-31 | 2000-10-05 | California Institute Of Technology | Novel ruthenium metal alkylidene complexes coordinated with triazolylidene ligands that exhibit high olefin metathesis activity |
WO2001070387A1 (de) * | 2000-03-23 | 2001-09-27 | Merck Patent Gmbh | Verfahren zur metathesereaktion ungesättigter organischer verbindungen |
JP2002020395A (ja) * | 2000-07-04 | 2002-01-23 | Sekisui Chem Co Ltd | 新規な高メタセシス活性の有機金属錯体化合物、これを含有してなるメタセシス反応触媒、この触媒を用いた重合方法、並びにこの重合方法により得られた樹脂組成物 |
US6409875B1 (en) | 1999-02-05 | 2002-06-25 | Materia, Inc. | Metathesis-active adhesion agents and methods for enhancing polymer adhesion to surfaces |
EP1115491A4 (de) * | 1998-09-10 | 2002-11-20 | Univ New Orleans Foundation | Katalysatorkomplex mit carben-ligand |
EP1275675A1 (de) * | 1999-12-07 | 2003-01-15 | Zeon Corporation | Durch ringöffnende polymerisation hergestellte copolymere, hydrierungsprodukt durch ringöffnende polyerisation hergestellter copolymere und verfahren zur herstellung derselben |
WO2003011455A1 (en) | 2001-08-01 | 2003-02-13 | California Institute Of Technology | Hexacoordinated ruthenium or osmium metal carbene metathesis catalysts |
WO2003011875A1 (de) | 2001-07-31 | 2003-02-13 | Bayer Chemicals Ag | Neue übergangsmetall-komplexe und deren einsatz in übergangsmetall-katalysierten reaktionen |
US6525125B1 (en) | 1999-02-05 | 2003-02-25 | Materia, Inc. | Polyolefin compositions having variable density and methods for their production and use |
WO2003027079A1 (fr) * | 2001-09-20 | 2003-04-03 | Zeon Corporation | Complexes de ruthenium, leur procede de preparation, et procedes de production de polymeres a anneau ouvert de cycloolefines et de produits d'hydrogenation associes, au moyen desdits complexes en tant que catalyseurs |
US6583236B1 (en) | 1999-02-05 | 2003-06-24 | Cymetech, Llc | Polyolefin compositions having enhanced ultraviolet and oxidative resistance and methods for their production and use |
US6620955B1 (en) | 2001-11-15 | 2003-09-16 | Richard L. Pederson | Chelating carbene ligand precursors and their use in the synthesis of metathesis catalysts |
JP2003531818A (ja) * | 1999-11-18 | 2003-10-28 | エル ペダーソン リチャード | フェロモン又はその成分のメタセシス合成方法 |
EP1373170A1 (de) * | 2001-03-30 | 2004-01-02 | California Institute Of Technology | Kreuz-metathese von funktionalisierten und substituierten olefinen unter einsatz von gruppe 8 übergangsmetall-carben-komplexe als methatese-katalysatoren |
US6696597B2 (en) | 1998-09-01 | 2004-02-24 | Tilliechem, Inc. | Metathesis syntheses of pheromones or their components |
US6838489B2 (en) | 2001-03-23 | 2005-01-04 | Cymetech, Llc | High activity metal carbene metathesis catalysts generated using a thermally activated N-heterocyclic carbene precursor |
US6900347B2 (en) | 1998-09-01 | 2005-05-31 | Tilliechem, Inc. | Impurity inhibition in olefin metathesis reactions |
WO2005094345A2 (en) | 2004-03-29 | 2005-10-13 | California Institute Of Technology | Latent, high-activity olefin metathesis catalysts containing an n-heterocyclic carbene ligand |
WO2005121158A1 (en) | 2004-06-09 | 2005-12-22 | University Technologies International Inc. | Transition metal carbene complexes containing a cationic substituent as catalysts of olefin metathesis reactions |
US7002049B2 (en) | 2002-08-19 | 2006-02-21 | Eastman Chemical Company | Process for α,β-dihydroxyalkenes and derivatives |
EP1698686A1 (de) | 2004-11-23 | 2006-09-06 | Institut Français du Pétrole | Gleichzeitige Herstellung von Olefinen und Estern durch Ethenolyse von ungesättigten Fetten in nicht-wässrigen ionischen Flüssigkeiten. |
EP1810961A1 (de) * | 2006-01-24 | 2007-07-25 | Institut Français du Pétrole | Verfahren zur gleichzeitigen Produktion von Olefinen und Diestern oder Disäuren mittels Homometathese von ungesättigten Fettkörpern in nichtwässrigen, ionischen Flüssigkeiten |
US7285593B1 (en) | 1998-05-19 | 2007-10-23 | Advanced Polymer Technologies, Inc. | Polyolefin compositions optionally having variable toughness and/or hardness |
US7329758B1 (en) | 1999-05-24 | 2008-02-12 | California Institute Of Technology | Imidazolidine-based metal carbene metathesis catalysts |
DE102007020694A1 (de) | 2007-05-03 | 2008-11-06 | Evonik Degussa Gmbh | Schwefelhaltige Metathesekatalysatoren |
US7507854B2 (en) | 1998-09-01 | 2009-03-24 | Materia, Inc. | Impurity reduction in Olefin metathesis reactions |
WO2010066959A1 (fr) | 2008-12-10 | 2010-06-17 | Ifp | Composition catalytique et procede de metathese de corps gras insature. |
EP2210870A1 (de) | 2009-01-23 | 2010-07-28 | Evonik Degussa GmbH | Hydroxy- und aldehydfunktionale Verbindungen |
WO2010084053A1 (de) | 2009-01-23 | 2010-07-29 | Evonik Degussa Gmbh | Verfahren zur herstellung von aldehydfuntionale verbindungen |
US8008224B2 (en) | 2005-12-16 | 2011-08-30 | Materia, Inc. | Organometallic ruthenium complexes and related methods for the preparation of tetra-substituted and other hindered olefins |
US8241575B2 (en) | 2008-01-28 | 2012-08-14 | The Johns Hopkins University | Molecularly imprinted polymer sensor device |
JP2012229232A (ja) * | 2000-06-23 | 2012-11-22 | California Inst Of Technology | クロスメタセシスおよび閉環メタセシスによる、官能性および非官能性オレフィンの合成 |
US8552191B2 (en) | 2007-03-22 | 2013-10-08 | Opko Health, Inc. | Process and intermediates for the synthesis of 8-[{1-(3,5-bis-(trifluoromethyl)phenyl)-ethoxy}-methyl]-8-phenyl-1,7-diaza-spiro[4.5]decan-2-one compounds |
EP2270063A3 (de) * | 1999-05-31 | 2013-10-30 | Zeon Corporation | Verfahren zur Herstellung von Hydrogenierter, durch Ringöffnung erhaltenes, Cycloolefinpolymer |
WO2013186238A1 (de) | 2012-06-13 | 2013-12-19 | Basf Se | Verfahren zur herstellung makrocyclischer ketone |
US9233994B2 (en) | 2010-03-22 | 2016-01-12 | University Court Of The University Of St. Andrews | Ruthenium complexes for use in olefin metathesis |
US9249144B2 (en) | 2008-09-05 | 2016-02-02 | Opko Health, Inc. | Process and intermediates for the synthesis of 8-[{1-(3,5-bis-(trifluoromethyl)phenyl)-ethoxy}-methyl]-8-phenyl-1,7-diaza-spiro[4.5]decan-2-one compounds |
WO2016063282A1 (en) | 2014-10-21 | 2016-04-28 | Stratasys Ltd. | Three-dimensional inkjet printing using ring-opening metathesis polymerization |
WO2017134673A1 (en) | 2016-02-07 | 2017-08-10 | Stratasys Ltd. | Three-dimensional printing combining ring-opening metathesis polymerization and free radical polymerization |
WO2017134674A1 (en) | 2016-02-05 | 2017-08-10 | Stratasys Ltd. | Three-dimensional inkjet printing using ring-opening metathesis polymerization |
US9796889B2 (en) | 1999-02-05 | 2017-10-24 | Materia, Inc. | Metathesis-active adhesion agents and methods for enhancing polymer adhesion to surfaces |
WO2017187434A1 (en) | 2016-04-26 | 2017-11-02 | Stratasys Ltd. | Three-dimensional inkjet printing using ring-opening metathesis polymerization |
US11173653B2 (en) | 2016-02-05 | 2021-11-16 | Stratasys Ltd. | Three-dimensional inkjet printing using polyamide-forming materials |
Families Citing this family (136)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19815275B4 (de) | 1998-04-06 | 2009-06-25 | Evonik Degussa Gmbh | Alkylidenkomplexe des Rutheniums mit N-heterozyklischen Carbenliganden und deren Verwendung als hochaktive, selektive Katalysatoren für die Olefin-Metathese |
DE10015452A1 (de) | 2000-03-29 | 2001-10-04 | Bayer Ag | Verfahren zur Polymerisation von polar substituierten Cycloalkenen |
US7494927B2 (en) * | 2000-05-15 | 2009-02-24 | Asm International N.V. | Method of growing electrical conductors |
DE10064750A1 (de) * | 2000-12-22 | 2002-06-27 | Bayer Ag | Verfahren zur Herstellung von 1,6-Hexandiolen |
KR100869981B1 (ko) * | 2001-03-26 | 2008-11-24 | 다우 글로벌 테크놀로지스 인크. | 불포화 지방산 에스테르 또는 불포화 지방산과 저급 올레핀과의 상호교환반응 |
JP2005523931A (ja) | 2002-04-29 | 2005-08-11 | ダウ グローバル テクノロジーズ インコーポレイティド | 種子油の工業的利用のための統合化学プロセス |
DE10231368A1 (de) * | 2002-07-11 | 2004-02-05 | Studiengesellschaft Kohle Mbh | Verfahren zur Herstellung von Imidazoliumsalzen |
US7094898B2 (en) * | 2003-05-29 | 2006-08-22 | University Of Ottawa | Ruthenium compounds, their production and use |
US7205424B2 (en) * | 2003-06-19 | 2007-04-17 | University Of New Orleans Research And Technology Foundation, Inc. | Preparation of ruthenium-based olefin metathesis catalysts |
ATE400542T1 (de) * | 2003-10-09 | 2008-07-15 | Dow Global Technologies Inc | Verbessertes verfahren zur synthese ungesättigter alkohole |
KR101162394B1 (ko) | 2004-02-23 | 2012-07-06 | 란세스 인크. | 저분자량 니트릴 고무의 제조 방법 |
CA2462011A1 (en) * | 2004-02-23 | 2005-08-23 | Bayer Inc. | Process for the preparation of low molecular weight nitrile rubber |
US20060129013A1 (en) * | 2004-12-09 | 2006-06-15 | Abazajian Armen N | Specific functionalization and scission of linear hydrocarbon chains |
DE102004060247A1 (de) * | 2004-12-15 | 2006-06-29 | Studiengesellschaft Kohle Mbh | Neue N-heterocyclische Carbene und ihre Anwendung in der Katalyse |
US8025922B2 (en) | 2005-03-15 | 2011-09-27 | Asm International N.V. | Enhanced deposition of noble metals |
US7666773B2 (en) | 2005-03-15 | 2010-02-23 | Asm International N.V. | Selective deposition of noble metal thin films |
US8461223B2 (en) | 2005-04-07 | 2013-06-11 | Aspen Aerogels, Inc. | Microporous polycyclopentadiene-based aerogels |
US7750149B2 (en) * | 2005-04-11 | 2010-07-06 | Wisconsin Alumni Research Foundation | Seven-membered heterocyclic carbenes and their metal complexes |
JP2006342212A (ja) * | 2005-06-07 | 2006-12-21 | Kuraray Co Ltd | 開環メタセシス重合体の製造方法、並びに、開環メタセシス重合体及びそれから得られる成形体 |
US20070014919A1 (en) * | 2005-07-15 | 2007-01-18 | Jani Hamalainen | Atomic layer deposition of noble metal oxides |
WO2007112242A1 (en) * | 2006-03-23 | 2007-10-04 | Shell Oil Company | Olefin conversion process and olefin recovery process |
US7435484B2 (en) * | 2006-09-01 | 2008-10-14 | Asm Japan K.K. | Ruthenium thin film-formed structure |
DE102007018148A1 (de) | 2007-04-16 | 2008-10-23 | Evonik Degussa Gmbh | Verfahren zur Metathese in elektronenarmen aromatischen Lösungsmitteln |
CA2691196C (en) * | 2007-06-21 | 2016-05-24 | Amgen Inc. | Methods of synthesizing cinacalcet and salts thereof |
US20090087339A1 (en) * | 2007-09-28 | 2009-04-02 | Asm Japan K.K. | METHOD FOR FORMING RUTHENIUM COMPLEX FILM USING Beta-DIKETONE-COORDINATED RUTHENIUM PRECURSOR |
BRPI0911432B1 (pt) † | 2008-04-08 | 2018-01-02 | Evonik Degussa Gmbh | COMPLEXOS DE Ru-CARBENO, SEUS PROCESSOS DE PREPARAÇÃO E SEU USO |
EP2147721A1 (de) * | 2008-07-08 | 2010-01-27 | Lanxess Deutschland GmbH | Katalysator-Systeme und deren Verwendung für Metathese-Reaktionen |
EP2157076A1 (de) * | 2008-08-21 | 2010-02-24 | Cognis IP Management GmbH | Verfahren zur Herstellung von ungesättigten alpha, omega Dicarbonsäurediestern |
US8084104B2 (en) * | 2008-08-29 | 2011-12-27 | Asm Japan K.K. | Atomic composition controlled ruthenium alloy film formed by plasma-enhanced atomic layer deposition |
US9206223B2 (en) | 2008-09-22 | 2015-12-08 | Aileron Therapeutics, Inc. | Methods for preparing purified polypeptide compositions |
WO2010051268A1 (en) * | 2008-10-31 | 2010-05-06 | Dow Global Technologies Inc. | Olefin metathesis process employing bimetallic ruthenium complex with bridging hydrido ligands |
DK2352712T3 (en) * | 2008-11-26 | 2018-09-10 | Elevance Renewable Sciences | PROCEDURES FOR PREPARING JET FUEL FROM NATURAL OIL MATERIALS THROUGH METATES REACTIONS |
WO2010062932A1 (en) * | 2008-11-26 | 2010-06-03 | Elevance Renewable Sciences, Inc. | Methods of producing jet fuel from natural oil feedstocks through oxygen-cleaved reactions |
US9379011B2 (en) | 2008-12-19 | 2016-06-28 | Asm International N.V. | Methods for depositing nickel films and for making nickel silicide and nickel germanide |
WO2010129051A1 (en) * | 2009-05-05 | 2010-11-11 | Stepan Company | Sulfonated internal olefin surfactant for enhanced oil recovery |
US20110020546A1 (en) * | 2009-05-15 | 2011-01-27 | Asm International N.V. | Low Temperature ALD of Noble Metals |
US9222056B2 (en) | 2009-10-12 | 2015-12-29 | Elevance Renewable Sciences, Inc. | Methods of refining natural oils, and methods of producing fuel compositions |
US9051519B2 (en) | 2009-10-12 | 2015-06-09 | Elevance Renewable Sciences, Inc. | Diene-selective hydrogenation of metathesis derived olefins and unsaturated esters |
WO2011046872A2 (en) | 2009-10-12 | 2011-04-21 | Elevance Renewable Sciences, Inc. | Methods of refining and producing fuel from natural oil feedstocks |
US9000246B2 (en) | 2009-10-12 | 2015-04-07 | Elevance Renewable Sciences, Inc. | Methods of refining and producing dibasic esters and acids from natural oil feedstocks |
US8735640B2 (en) | 2009-10-12 | 2014-05-27 | Elevance Renewable Sciences, Inc. | Methods of refining and producing fuel and specialty chemicals from natural oil feedstocks |
US9382502B2 (en) | 2009-10-12 | 2016-07-05 | Elevance Renewable Sciences, Inc. | Methods of refining and producing isomerized fatty acid esters and fatty acids from natural oil feedstocks |
US9169447B2 (en) | 2009-10-12 | 2015-10-27 | Elevance Renewable Sciences, Inc. | Methods of refining natural oils, and methods of producing fuel compositions |
US9175231B2 (en) | 2009-10-12 | 2015-11-03 | Elevance Renewable Sciences, Inc. | Methods of refining natural oils and methods of producing fuel compositions |
US9365487B2 (en) | 2009-10-12 | 2016-06-14 | Elevance Renewable Sciences, Inc. | Methods of refining and producing dibasic esters and acids from natural oil feedstocks |
WO2011059803A2 (en) * | 2009-10-29 | 2011-05-19 | Board Of Regents, The University Of Texas System | Ruthenium-alkylidenes containing acyclic diaminocarbenes for obtaining low e/z ratios in cross metathesis |
US9403781B2 (en) | 2010-04-27 | 2016-08-02 | The Regents Of The University Of California | Crystalline 1H-1,2,3-triazol-5-ylidenes |
SG188274A1 (en) | 2010-08-23 | 2013-04-30 | Materia Inc | Vartm flow modifications for low viscosity resin systems |
EP2428269A1 (de) | 2010-09-08 | 2012-03-14 | Bergen Teknologioverføring AS | Neue Olefin-Metathesen-Katalysatoren |
US8871617B2 (en) | 2011-04-22 | 2014-10-28 | Asm Ip Holding B.V. | Deposition and reduction of mixed metal oxide thin films |
US8524930B2 (en) | 2011-05-31 | 2013-09-03 | Exxonmobil Chemical Patents Inc. | Class of olefin metathesis catalysts, methods of preparation, and processes for the use thereof |
EP2714272A4 (de) * | 2011-05-31 | 2015-03-04 | Exxonmobil Chem Patents Inc | Neue klasse von olefin-metathese-katalysatoren, herstellungsverfahren dafür und verfahren zu ihrer verwendung |
CA2839757C (en) | 2011-06-17 | 2021-01-19 | Materia, Inc. | Adhesion promoters and gel-modifiers for olefin metathesis compositions |
US8993819B2 (en) | 2011-07-12 | 2015-03-31 | Basf Se | Process for preparing cycloheptene |
JP5916855B2 (ja) | 2011-07-12 | 2016-05-11 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | シクロヘプテンの製造法 |
US9181360B2 (en) | 2011-08-12 | 2015-11-10 | Exxonmobil Chemical Patents Inc. | Polymers prepared by ring opening / cross metathesis |
GB201116719D0 (en) * | 2011-09-28 | 2011-11-09 | Univ St Andrews | Ruthenium polymerisation catalysts |
FR2983475B1 (fr) * | 2011-12-02 | 2014-01-17 | IFP Energies Nouvelles | Procede de metathese d'olefines lineaires alpha utilisant un complexe du ruthenium comportant un carbene n-heterocyclique dissymetrique |
US9169174B2 (en) | 2011-12-22 | 2015-10-27 | Elevance Renewable Sciences, Inc. | Methods for suppressing isomerization of olefin metathesis products |
US9139493B2 (en) | 2011-12-22 | 2015-09-22 | Elevance Renewable Sciences, Inc. | Methods for suppressing isomerization of olefin metathesis products |
US9133416B2 (en) | 2011-12-22 | 2015-09-15 | Elevance Renewable Sciences, Inc. | Methods for suppressing isomerization of olefin metathesis products |
KR20140145960A (ko) | 2012-03-13 | 2014-12-24 | 인비스타 테크놀러지스 에스.에이 알.엘. | 나일론 중합체 및 방법 |
EP2841468B1 (de) | 2012-04-24 | 2020-08-26 | Stepan Company | Ungesättigte fettalkoholalkoxylate aus einer metathese von natürlichem öl |
IN2014DN08906A (de) | 2012-04-24 | 2015-05-22 | Elevance Renewable Sciences | |
MY174521A (en) | 2012-04-24 | 2020-04-23 | Stepan Co | Unsaturated fatty alcohol derivatives from natural oil metathesis |
WO2013192384A1 (en) | 2012-06-20 | 2013-12-27 | Elevance Renewable Sciences, Inc. | Natural oil metathesis compositions |
WO2014022482A1 (en) | 2012-08-01 | 2014-02-06 | California Institute Of Technology | Solvent-free enyne metathesis polymerization |
US9234985B2 (en) | 2012-08-01 | 2016-01-12 | California Institute Of Technology | Birefringent polymer brush structures formed by surface initiated ring-opening metathesis polymerization |
WO2014055720A1 (en) * | 2012-10-05 | 2014-04-10 | California Institute Of Technology | Photoinitiated olefin metathesis polymerization |
US9388098B2 (en) | 2012-10-09 | 2016-07-12 | Elevance Renewable Sciences, Inc. | Methods of making high-weight esters, acids, and derivatives thereof |
FR2999185B1 (fr) * | 2012-12-12 | 2015-01-02 | Ecole Nationale Superieure De Chimie De Rennes | Procede de metathese d'olefines lineaires alpha utilisant un complexe du ruthenium comportant un diaminocarbene n-heterocyclique dissymetrique insature |
US9527982B2 (en) | 2012-12-19 | 2016-12-27 | Materia, Inc. | Storage stable adhesion promoter compositions for cyclic olefin resin compositions |
FR3002161B1 (fr) * | 2013-02-21 | 2015-12-18 | IFP Energies Nouvelles | Procede de metathese d'olefines issues de coupes fischer-tropsch utilisant un complexe du ruthenium comportant un diaminocarbene n-heterocyclique symetrique |
US20140357820A1 (en) | 2013-02-27 | 2014-12-04 | Materia, Inc. | Olefin metathesis catalyst compositions comprising at least two metal carbene olefin metathesis catalysts |
US9598531B2 (en) | 2013-02-27 | 2017-03-21 | Materia, Inc. | Olefin metathesis catalyst compositions comprising at least two metal carbene olefin metathesis catalysts |
EP2778154A1 (de) * | 2013-03-13 | 2014-09-17 | Evonik Industries AG | In situ Generierung von Ruthenium-Katalysatoren zur Olefin-Metathese |
CN105189525A (zh) | 2013-03-14 | 2015-12-23 | 埃莱万斯可再生能源科学股份有限公司 | 烯基糖苷及其制备 |
WO2014144634A1 (en) | 2013-03-15 | 2014-09-18 | Materia, Inc. | In-mold coating of romp polymers |
WO2014153406A1 (en) | 2013-03-20 | 2014-09-25 | Elevance Renewable Sciences, Inc. | Acid catalyzed oligomerization of alkyl esters and carboxylic acids |
WO2014169055A1 (en) | 2013-04-09 | 2014-10-16 | Materia, Inc. | Cross metathesis of poly-branched poly-olefins |
EP3004123B1 (de) * | 2013-05-24 | 2018-03-28 | ARLANXEO Deutschland GmbH | Rutheniumbasierter komplexe, ihre herstellung und verwendung als katalysatoren |
WO2014198022A1 (en) | 2013-06-09 | 2014-12-18 | Lanxess Deutschland Gmbh | Ruthenium- or osmium-based complex catalysts |
AU2014302626B2 (en) | 2013-06-24 | 2017-09-28 | Materia, Inc. | Thermal insulation |
CN105492489B (zh) | 2013-07-03 | 2017-06-13 | 马特里亚公司 | 液体模制组合物 |
EP3041812B1 (de) | 2013-09-04 | 2022-08-10 | California Institute of Technology | Funktionalisierte lineare und cyclische polyolefine |
JP6273749B2 (ja) * | 2013-10-04 | 2018-02-07 | 国立大学法人山口大学 | ネットワークポリマー及びポリマーゲル電解質 |
EP3063592B1 (de) | 2013-10-30 | 2021-04-07 | California Institute of Technology | Direkte fotostrukturierung von robusten und unterschiedlichen materialien |
US10633484B2 (en) | 2014-01-10 | 2020-04-28 | Materia, Inc. | Method and composition for improving adhesion of metathesis compositions to substrates |
EP3110862A4 (de) | 2014-02-27 | 2017-11-01 | Materia, Inc. | Haftvermittlerzusammensetzungen für cyclische olefinharzzusammensetzungen |
CA2981087A1 (en) | 2014-03-27 | 2015-10-01 | Trent University | Certain metathesized natural oil triacylglycerol polyols for use in polyurethane applications and their related physical properties |
US10000601B2 (en) | 2014-03-27 | 2018-06-19 | Trent University | Metathesized triacylglycerol polyols for use in polyurethane applications and their related properties |
CA2981082A1 (en) | 2014-03-27 | 2015-10-01 | Trent University | Metathesized triacylglycerol green polyols from palm oil for use in polyurethane applications and their related physical properties |
US9328206B2 (en) | 2014-05-30 | 2016-05-03 | Pall Corporation | Self-assembling polymers—III |
US9593217B2 (en) | 2014-05-30 | 2017-03-14 | Pall Corporation | Self-assembled structure and membrane comprising block copolymer and process for producing the same by spin coating (Va) |
US9592476B2 (en) | 2014-05-30 | 2017-03-14 | Pall Corporation | Membrane comprising self-assembled block copolymer and process for producing the same by hybrid casting (IIb) |
US9604181B2 (en) | 2014-05-30 | 2017-03-28 | Pall Corporation | Membrane comprising self-assembled block copolymer and process for producing the same by spray coating (IIc) |
US9592477B2 (en) | 2014-05-30 | 2017-03-14 | Pall Corporation | Membrane comprising self-assembled block copolymer and process for producing the same by hybrid casting (Ib) |
US9162189B1 (en) | 2014-05-30 | 2015-10-20 | Pall Corporation | Membrane comprising self-assembled block copolymer and process for producing the same by spin coating (Ia) |
US9169361B1 (en) | 2014-05-30 | 2015-10-27 | Pall Corporation | Self-assembling polymers—VI |
US9163122B1 (en) | 2014-05-30 | 2015-10-20 | Pall Corporation | Self-assembling polymers—II |
US9593219B2 (en) | 2014-05-30 | 2017-03-14 | Pall Corporation | Membrane comprising self-assembled block copolymer and process for producing the same by spin coating (IIa) |
US9598543B2 (en) | 2014-05-30 | 2017-03-21 | Pall Corporation | Self-assembled structure and membrane comprising block copolymer and process for producing the same by spin coating (VIa) |
US9193835B1 (en) | 2014-05-30 | 2015-11-24 | Pall Corporation | Self-assembling polymers—IV |
US9593218B2 (en) | 2014-05-30 | 2017-03-14 | Pall Corporation | Self-assembled structure and membrane comprising block copolymer and process for producing the same by spin coating (IIIa) |
US9469733B2 (en) | 2014-05-30 | 2016-10-18 | Pall Corporation | Self-assembled structure and membrane comprising block copolymer and process for producing the same by spin coating (IVa) |
US9441078B2 (en) | 2014-05-30 | 2016-09-13 | Pall Corporation | Self-assembling polymers—I |
US9765171B2 (en) | 2014-05-30 | 2017-09-19 | Pall Corporation | Self-assembling polymers—V |
US9616395B2 (en) | 2014-05-30 | 2017-04-11 | Pall Corportaion | Membrane comprising self-assembled block copolymer and process for producing the same by spray coating (Ic) |
US9260569B2 (en) | 2014-06-30 | 2016-02-16 | Pall Corporation | Hydrophilic block copolymers and method of preparation thereof (III) |
US9394407B2 (en) | 2014-06-30 | 2016-07-19 | Pall Corporation | Hydrophilic block copolymers and membranes prepared therefrom (I) |
US9303133B2 (en) | 2014-06-30 | 2016-04-05 | Pall Corporation | Hydrophilic membranes and method of preparation thereof (IV) |
US9718924B2 (en) | 2014-06-30 | 2017-08-01 | Pall Corporation | Hydrophilic block copolymers and membranes prepared therefrom (II) |
US9962662B2 (en) | 2014-06-30 | 2018-05-08 | Pall Corporation | Fluorinated polymer and use thereof in the preparation of hydrophilic membranes (vi) |
US9309367B2 (en) | 2014-06-30 | 2016-04-12 | Pall Corporation | Membranes comprising cellulosic material and hydrophilic block copolymer (V) |
US9254466B2 (en) | 2014-06-30 | 2016-02-09 | Pall Corporation | Crosslinked cellulosic membranes |
US9777245B2 (en) | 2015-01-30 | 2017-10-03 | Trent University | Methods of fractionating metathesized triacylglycerol polyols and uses thereof |
CN116120715A (zh) | 2015-02-12 | 2023-05-16 | 马特里亚公司 | 包含官能弹性体的环烯烃树脂组合物 |
WO2016130742A1 (en) | 2015-02-14 | 2016-08-18 | Materia, Inc. | Romp polymers having improved resistance to hydrocarbon fluids |
EP3115368A1 (de) | 2015-07-10 | 2017-01-11 | Bergen Teknologioverforing AS | Verbesserte olefinmetathesekatalysatoren |
EP3124579A1 (de) | 2015-07-31 | 2017-02-01 | Total Marketing Services | Schmiermittelzusammensetzung mit verzweigten diestern und viskositätsindexverbesserer |
EP3124580A1 (de) | 2015-07-31 | 2017-02-01 | Total Marketing Services | Verzweigte diester zur verwendung bei der senkung des kraftstoffverbrauchs eines motors |
JP7013370B2 (ja) | 2015-09-24 | 2022-01-31 | ユミコア・アクチエンゲゼルシャフト・ウント・コムパニー・コマンディットゲゼルシャフト | 金属カルベンオレフィンメタセシス触媒 |
US9607842B1 (en) | 2015-10-02 | 2017-03-28 | Asm Ip Holding B.V. | Methods of forming metal silicides |
US9776179B2 (en) | 2015-11-18 | 2017-10-03 | Provivi, Inc. | Production of fatty olefin derivatives via olefin metathesis |
HUE053613T2 (hu) | 2015-11-18 | 2021-07-28 | Provivi Inc | Mikroorganizmusok rovarferomonok és kapcsolódó vegyületek elõállítására |
AR110606A1 (es) | 2016-06-06 | 2019-04-17 | Provivi Inc | Producción semi-biosintética de alcoholes grasos y aldehídos grasos |
PL3496855T3 (pl) | 2016-08-15 | 2023-03-20 | Umicore Ag & Co. Kg | Katalizatory metatezy |
EP3500557A4 (de) * | 2016-08-19 | 2020-03-18 | Umicore Ag & Co. Kg | Olefinmetathesekatalysatoren |
EP4194092A1 (de) | 2016-08-24 | 2023-06-14 | Umicore AG & Co. KG | Synthese und charakterisierung von metathesekatalysatoren |
EP3515885B1 (de) | 2016-09-23 | 2023-12-13 | Umicore Ag & Co. Kg | Herstellung von aminosäuren und aminosäurederivaten |
EP3635124A4 (de) | 2017-05-17 | 2021-03-31 | Provivi, Inc. | Mikroorganismen zur herstellung von insektenpheromonen und verwandten verbindungen |
US11471867B2 (en) * | 2017-06-23 | 2022-10-18 | Gwangju Institute Of Science And Technology | Ligand for forming ruthenium complex, ruthenium complex catalyst, production method therefor and use thereof |
FR3075802B1 (fr) | 2017-12-22 | 2020-11-20 | Demeta | Procede de polymerisation de cycloolefines par metathese avec ouverture de cycle |
EP3546495A1 (de) | 2018-03-29 | 2019-10-02 | Evonik Degussa GmbH | Verfahren zur herstellung von temperaturstabilen polyalkenameren |
US10995049B2 (en) | 2019-07-19 | 2021-05-04 | California Institute Of Technology | Total synthesis of prostaglandin J natural products and their intermediates |
US20240124809A1 (en) | 2022-10-03 | 2024-04-18 | The Goodyear Tire & Rubber Company | Reactor cleaning process and composition |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0721953A1 (de) * | 1994-12-29 | 1996-07-17 | Hoechst Aktiengesellschaft | Heterocyclische Carbene enthaltende Metallkomplexverbindungen |
WO1997006185A1 (en) * | 1995-08-03 | 1997-02-20 | California Institute Of Technology | High metathesis activity ruthenium and osmium metal carbene complexes |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5312940A (en) * | 1992-04-03 | 1994-05-17 | California Institute Of Technology | Ruthenium and osmium metal carbene complexes for olefin metathesis polymerization |
JP3067031B2 (ja) | 1992-04-03 | 2000-07-17 | カリフォルニア インスティチュート オブ テクノロジー | オレフィンメタセシス重合方法 |
DE19610908A1 (de) * | 1996-03-20 | 1997-09-25 | Hoechst Ag | Verfahren zur Herstellung heterocyclischer Carbene |
DE19815275B4 (de) | 1998-04-06 | 2009-06-25 | Evonik Degussa Gmbh | Alkylidenkomplexe des Rutheniums mit N-heterozyklischen Carbenliganden und deren Verwendung als hochaktive, selektive Katalysatoren für die Olefin-Metathese |
DE19902439A1 (de) * | 1999-01-22 | 2000-08-03 | Aventis Res & Tech Gmbh & Co | Homo- und heterobimetallische Alkylidenkomplexe des Rutheniums mit N-heterocyclischen Carbenliganden und deren Anwendung als hochaktive, selektive Katalysatoren für die Olefin-Metathese |
EP1180107B1 (de) * | 1999-03-31 | 2008-06-11 | California Institute Of Technology | Mit triazolydin-liganden koordinierte rutheniummetall-alkyliden-komplexe die hohe olefin-metathese-aktivität aufweisen |
US7329758B1 (en) * | 1999-05-24 | 2008-02-12 | California Institute Of Technology | Imidazolidine-based metal carbene metathesis catalysts |
US6794534B2 (en) * | 2000-06-23 | 2004-09-21 | California Institute Of Technology | Synthesis of functionalized and unfunctionalized olefins via cross and ring-closing metathesis |
US7241898B2 (en) * | 2003-08-02 | 2007-07-10 | Boehringer Ingelheim International Gmbh | Metathesis catalysts |
US20060293526A1 (en) * | 2003-08-11 | 2006-12-28 | Merk Patent Gmbh | Immobilised imidazoles and ruthenium catalysts |
JP2007501814A (ja) * | 2003-08-11 | 2007-02-01 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフトング | N−ヘテロ環カルベン配位子を有する固定化可能ルテニウム触媒 |
EP1735352B1 (de) * | 2004-03-29 | 2019-08-21 | California Institute Of Technology | Einen n-heterocyclischen carbenliganden enthaltende latente katalysatoren mit hoher aktivität für die olefinmetathese |
EP1765839B1 (de) * | 2004-06-09 | 2017-01-25 | UTI Limited Partnership | Einen kationischen substituenten enthaltende übergangsmetallcarbenkomplexe als katalysatoren von olefin-metathesereaktionen |
-
1998
- 1998-04-06 DE DE19815275A patent/DE19815275B4/de not_active Expired - Lifetime
-
1999
- 1999-03-18 US US09/647,742 patent/US6635768B1/en not_active Expired - Lifetime
- 1999-03-18 IL IL13859599A patent/IL138595A/en not_active IP Right Cessation
- 1999-03-18 DE DE59912097T patent/DE59912097D1/de not_active Expired - Lifetime
- 1999-03-18 WO PCT/EP1999/001785 patent/WO1999051344A1/de active IP Right Grant
- 1999-03-18 JP JP2000542103A patent/JP4531253B2/ja not_active Expired - Lifetime
- 1999-03-18 EP EP99910357A patent/EP1087838B1/de not_active Revoked
-
2003
- 2003-07-29 US US10/630,552 patent/US7294717B2/en not_active Expired - Lifetime
-
2004
- 2004-12-23 US US11/021,967 patent/US7652145B2/en not_active Expired - Lifetime
-
2007
- 2007-07-26 US US11/828,828 patent/US7378528B2/en not_active Expired - Fee Related
-
2008
- 2008-05-05 US US12/115,139 patent/US20080207911A1/en not_active Abandoned
-
2011
- 2011-04-20 US US13/090,688 patent/US8153810B2/en not_active Expired - Fee Related
-
2014
- 2014-02-28 US US14/193,785 patent/US20150038723A1/en not_active Abandoned
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0721953A1 (de) * | 1994-12-29 | 1996-07-17 | Hoechst Aktiengesellschaft | Heterocyclische Carbene enthaltende Metallkomplexverbindungen |
WO1997006185A1 (en) * | 1995-08-03 | 1997-02-20 | California Institute Of Technology | High metathesis activity ruthenium and osmium metal carbene complexes |
Non-Patent Citations (1)
Title |
---|
T. WESKAMP ET AL.: "A Novel Class of Ruthenium Catalysts for Olefin metathesis", ANGEW. CHEM. INT. ED., vol. 37, no. 18, 1998, pages 2490 - 2493, XP002103755 * |
Cited By (90)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7285593B1 (en) | 1998-05-19 | 2007-10-23 | Advanced Polymer Technologies, Inc. | Polyolefin compositions optionally having variable toughness and/or hardness |
US7507854B2 (en) | 1998-09-01 | 2009-03-24 | Materia, Inc. | Impurity reduction in Olefin metathesis reactions |
US6696597B2 (en) | 1998-09-01 | 2004-02-24 | Tilliechem, Inc. | Metathesis syntheses of pheromones or their components |
US6900347B2 (en) | 1998-09-01 | 2005-05-31 | Tilliechem, Inc. | Impurity inhibition in olefin metathesis reactions |
US7902389B2 (en) | 1998-09-10 | 2011-03-08 | Nolan Steven P | Catalyst complex with carbene ligand |
EP1115491A4 (de) * | 1998-09-10 | 2002-11-20 | Univ New Orleans Foundation | Katalysatorkomplex mit carben-ligand |
US8859779B2 (en) | 1998-09-10 | 2014-10-14 | Materia, Inc. | Catalyst complex with carbene ligand |
US9233365B2 (en) | 1998-09-10 | 2016-01-12 | Materia, Inc. | Catalyst complex with carbene ligand |
US9339805B2 (en) | 1998-09-10 | 2016-05-17 | Materia, Inc. | Catalyst complex with carbene ligand |
EP2116302A1 (de) * | 1998-09-10 | 2009-11-11 | University Of New Orleans Foundation | Katalysatorkomplex mit einem heterozyklischen Carbenliganden |
US7622590B1 (en) | 1998-09-10 | 2009-11-24 | University Of New Orleans Foundation | Catalyst complex with carbene ligand |
US9796889B2 (en) | 1999-02-05 | 2017-10-24 | Materia, Inc. | Metathesis-active adhesion agents and methods for enhancing polymer adhesion to surfaces |
US6525125B1 (en) | 1999-02-05 | 2003-02-25 | Materia, Inc. | Polyolefin compositions having variable density and methods for their production and use |
US6409875B1 (en) | 1999-02-05 | 2002-06-25 | Materia, Inc. | Metathesis-active adhesion agents and methods for enhancing polymer adhesion to surfaces |
US6583236B1 (en) | 1999-02-05 | 2003-06-24 | Cymetech, Llc | Polyolefin compositions having enhanced ultraviolet and oxidative resistance and methods for their production and use |
US7339006B2 (en) | 1999-02-05 | 2008-03-04 | Cymetech, L.L.C. | Metathesis-active adhesion agents and methods for enhancing polymer adhesion to surfaces |
US8597794B2 (en) | 1999-02-05 | 2013-12-03 | Materia, Inc. | Metathesis-active adhesion agents and methods for enhancing polymer adhesion to surfaces |
US6624265B2 (en) | 1999-03-31 | 2003-09-23 | California Institute Of Technology | Ruthenium metal alkylidene complexes coordinated with triazolylidene ligands that exhibit high olefin metathesis activity |
WO2000058322A1 (en) * | 1999-03-31 | 2000-10-05 | California Institute Of Technology | Novel ruthenium metal alkylidene complexes coordinated with triazolylidene ligands that exhibit high olefin metathesis activity |
US6426419B1 (en) | 1999-03-31 | 2002-07-30 | California Institute Of Technology | Ruthenium metal alkylidene complexes coordinated with triazolylidene ligands that exhibit high olefin metathesis activity |
US8846939B2 (en) | 1999-05-24 | 2014-09-30 | California Institute Of Technology | Imidazolidine-based metal carbene metathesis catalysts |
US7329758B1 (en) | 1999-05-24 | 2008-02-12 | California Institute Of Technology | Imidazolidine-based metal carbene metathesis catalysts |
EP2270063A3 (de) * | 1999-05-31 | 2013-10-30 | Zeon Corporation | Verfahren zur Herstellung von Hydrogenierter, durch Ringöffnung erhaltenes, Cycloolefinpolymer |
JP4943612B2 (ja) * | 1999-11-18 | 2012-05-30 | エル ペダーソン リチャード | フェロモン又はその成分のメタセシス合成方法 |
JP2011178789A (ja) * | 1999-11-18 | 2011-09-15 | Richard L Pederson | フェロモン又はその成分のメタセシス合成方法 |
JP2003531818A (ja) * | 1999-11-18 | 2003-10-28 | エル ペダーソン リチャード | フェロモン又はその成分のメタセシス合成方法 |
JP2012111968A (ja) * | 1999-12-07 | 2012-06-14 | Nippon Zeon Co Ltd | 開環共重合体水素化物 |
EP1275675A1 (de) * | 1999-12-07 | 2003-01-15 | Zeon Corporation | Durch ringöffnende polymerisation hergestellte copolymere, hydrierungsprodukt durch ringöffnende polyerisation hergestellter copolymere und verfahren zur herstellung derselben |
EP1275675A4 (de) * | 1999-12-07 | 2004-11-17 | Zeon Corp | Durch ringöffnende polymerisation hergestellte copolymere, hydrierungsprodukt durch ringöffnende polyerisation hergestellter copolymere und verfahren zur herstellung derselben |
JP4556373B2 (ja) * | 1999-12-07 | 2010-10-06 | 日本ゼオン株式会社 | 開環共重合体水素化物の製造方法 |
JP2009287041A (ja) * | 1999-12-07 | 2009-12-10 | Nippon Zeon Co Ltd | 開環共重合体水素化物 |
JP2003527445A (ja) * | 2000-03-23 | 2003-09-16 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフトング | 不飽和有機化合物のメタセシス反応を実施するための方法 |
WO2001070387A1 (de) * | 2000-03-23 | 2001-09-27 | Merck Patent Gmbh | Verfahren zur metathesereaktion ungesättigter organischer verbindungen |
US6852900B2 (en) | 2000-03-23 | 2005-02-08 | Merck Patent Gmbh | Method for carrying out a metathesis reaction of unsaturated organic compounds |
JP2012229232A (ja) * | 2000-06-23 | 2012-11-22 | California Inst Of Technology | クロスメタセシスおよび閉環メタセシスによる、官能性および非官能性オレフィンの合成 |
JP2002020395A (ja) * | 2000-07-04 | 2002-01-23 | Sekisui Chem Co Ltd | 新規な高メタセシス活性の有機金属錯体化合物、これを含有してなるメタセシス反応触媒、この触媒を用いた重合方法、並びにこの重合方法により得られた樹脂組成物 |
US6838489B2 (en) | 2001-03-23 | 2005-01-04 | Cymetech, Llc | High activity metal carbene metathesis catalysts generated using a thermally activated N-heterocyclic carbene precursor |
EP1373170A1 (de) * | 2001-03-30 | 2004-01-02 | California Institute Of Technology | Kreuz-metathese von funktionalisierten und substituierten olefinen unter einsatz von gruppe 8 übergangsmetall-carben-komplexe als methatese-katalysatoren |
EP1373170A4 (de) * | 2001-03-30 | 2007-03-21 | California Inst Of Techn | Kreuz-metathese von funktionalisierten und substituierten olefinen unter einsatz von gruppe 8 übergangsmetall-carben-komplexe als methatese-katalysatoren |
US9403854B2 (en) | 2001-03-30 | 2016-08-02 | California Institute Of Technology | Cross-metathesis reaction of functionalized and substituted olefins using group 8 transition metal carbene complexes as metathesis catalysts |
WO2003011875A1 (de) | 2001-07-31 | 2003-02-13 | Bayer Chemicals Ag | Neue übergangsmetall-komplexe und deren einsatz in übergangsmetall-katalysierten reaktionen |
WO2003011455A1 (en) | 2001-08-01 | 2003-02-13 | California Institute Of Technology | Hexacoordinated ruthenium or osmium metal carbene metathesis catalysts |
WO2003027079A1 (fr) * | 2001-09-20 | 2003-04-03 | Zeon Corporation | Complexes de ruthenium, leur procede de preparation, et procedes de production de polymeres a anneau ouvert de cycloolefines et de produits d'hydrogenation associes, au moyen desdits complexes en tant que catalyseurs |
US7084222B2 (en) | 2001-09-20 | 2006-08-01 | Zeon Corporation | Ruthenium complexes, process for preparation thereof, and processes for producing open-ring polymer of cycloolefins and hydrogenation products thereof by using the complex as catalyst |
US6620955B1 (en) | 2001-11-15 | 2003-09-16 | Richard L. Pederson | Chelating carbene ligand precursors and their use in the synthesis of metathesis catalysts |
US9504997B2 (en) | 2001-11-15 | 2016-11-29 | Materia, Inc. | Chelating carbene ligand precursors and their use in the synthesis of metathesis catalysts |
US7820843B2 (en) | 2001-11-15 | 2010-10-26 | Materia, Inc. | Chelating carbene ligand precursors and their use in the synthesis of metathesis catalysts |
US7199252B2 (en) | 2002-08-19 | 2007-04-03 | Eastman Chemical Company | Process for α,β-dihydroxyalkenes and derivatives |
US7002049B2 (en) | 2002-08-19 | 2006-02-21 | Eastman Chemical Company | Process for α,β-dihydroxyalkenes and derivatives |
US9238709B2 (en) | 2004-03-29 | 2016-01-19 | Materia, Inc. | Latent, high-activity olefin metathesis catalysts containing an N-heterocyclic carbene ligand |
WO2005094345A2 (en) | 2004-03-29 | 2005-10-13 | California Institute Of Technology | Latent, high-activity olefin metathesis catalysts containing an n-heterocyclic carbene ligand |
US8871879B2 (en) | 2004-03-29 | 2014-10-28 | Materia, Inc. | Latent, high-activity olefin metathesis catalysts containing an N-heterocyclic carbene ligand |
WO2005121158A1 (en) | 2004-06-09 | 2005-12-22 | University Technologies International Inc. | Transition metal carbene complexes containing a cationic substituent as catalysts of olefin metathesis reactions |
US7365140B2 (en) | 2004-06-09 | 2008-04-29 | Uti Limited Partnership | Transition metal carbene complexes containing a cationic substituent as catalysts of olefin metathesis reactions |
EP1698686A1 (de) | 2004-11-23 | 2006-09-06 | Institut Français du Pétrole | Gleichzeitige Herstellung von Olefinen und Estern durch Ethenolyse von ungesättigten Fetten in nicht-wässrigen ionischen Flüssigkeiten. |
US8008224B2 (en) | 2005-12-16 | 2011-08-30 | Materia, Inc. | Organometallic ruthenium complexes and related methods for the preparation of tetra-substituted and other hindered olefins |
US7754904B2 (en) | 2006-01-24 | 2010-07-13 | Institut Francais Du Petrole | Process for co-producing olefins and diesters or diacids by homomethathesis of unsaturated fats in non-aqueous ionic liquids |
FR2896500A1 (fr) * | 2006-01-24 | 2007-07-27 | Inst Francais Du Petrole | Procede de co-production d'olefines et de diesters ou de diacides par homometathese de corps gras insatures dans des liquides ioniques non-aqueux. |
EP1810961A1 (de) * | 2006-01-24 | 2007-07-25 | Institut Français du Pétrole | Verfahren zur gleichzeitigen Produktion von Olefinen und Diestern oder Disäuren mittels Homometathese von ungesättigten Fettkörpern in nichtwässrigen, ionischen Flüssigkeiten |
NO338391B1 (no) * | 2006-01-24 | 2016-08-15 | Inst Francais Du Petrole | Fremgangsmåte for ko-produsering av olefiner og diestere eller disyrer ved homometatese av umettet fett i ikke-vandige ioniske væsker |
US8552191B2 (en) | 2007-03-22 | 2013-10-08 | Opko Health, Inc. | Process and intermediates for the synthesis of 8-[{1-(3,5-bis-(trifluoromethyl)phenyl)-ethoxy}-methyl]-8-phenyl-1,7-diaza-spiro[4.5]decan-2-one compounds |
US9260428B2 (en) | 2007-03-22 | 2016-02-16 | Opko Health, Inc. | Process and intermediates for the synthesis of 8-[{1-(3,5-bis-(trifluoromethyl)phenyl)-ethoxy}-methyl]-8-phenyl-1,7-diaza-spiro[4.5]decan-2-one compounds |
US10000493B2 (en) | 2007-03-22 | 2018-06-19 | Opko Health, Inc. | Process and intermediates for the synthesis of 8-[{1-(3,5-bis-(trifluoromethyl)phenyl)-ethoxy}-methyl]-8-phenyl-1,7-diaza-spiro[4.5]decan-2-one compounds |
EP1990348A2 (de) | 2007-05-03 | 2008-11-12 | Evonik Degussa GmbH | Schwefelhaltige Metathesekatalysatoren |
DE102007020694A1 (de) | 2007-05-03 | 2008-11-06 | Evonik Degussa Gmbh | Schwefelhaltige Metathesekatalysatoren |
US8183382B2 (en) | 2007-05-03 | 2012-05-22 | Evonik Degussa Gmbh | Sulphur-containing metathesis catalysts |
US8241575B2 (en) | 2008-01-28 | 2012-08-14 | The Johns Hopkins University | Molecularly imprinted polymer sensor device |
US9249144B2 (en) | 2008-09-05 | 2016-02-02 | Opko Health, Inc. | Process and intermediates for the synthesis of 8-[{1-(3,5-bis-(trifluoromethyl)phenyl)-ethoxy}-methyl]-8-phenyl-1,7-diaza-spiro[4.5]decan-2-one compounds |
US9822116B2 (en) | 2008-09-05 | 2017-11-21 | Opko Health, Inc. | Process and intermediates for the synthesis of 8-[{1-(3,5-bis-(trifluoromethyl)phenyl)-ethoxy}-methyl]-8-phenyl-1,7-diaza-spiro[4.5]decan-2-one compounds |
EP3034493A1 (de) | 2008-09-05 | 2016-06-22 | OPKO Health, Inc. | Synthese von 8-[{1-(3,5-bis-(trifluormethyl)phenyl)-ethoxy}-methyl]-8-phenyl-1,7-diaza-spiro[4.5]decan-2-on-verbindungen |
WO2010066959A1 (fr) | 2008-12-10 | 2010-06-17 | Ifp | Composition catalytique et procede de metathese de corps gras insature. |
EP2210870A1 (de) | 2009-01-23 | 2010-07-28 | Evonik Degussa GmbH | Hydroxy- und aldehydfunktionale Verbindungen |
WO2010084053A1 (de) | 2009-01-23 | 2010-07-29 | Evonik Degussa Gmbh | Verfahren zur herstellung von aldehydfuntionale verbindungen |
WO2010083934A1 (de) | 2009-01-23 | 2010-07-29 | Evonik Degussa Gmbh | Hydroxy- und aldehydfunktionale verbindungen |
DE102009005951A1 (de) | 2009-01-23 | 2010-07-29 | Evonik Degussa Gmbh | Aldehydfunktionale Verbindungen |
US9233994B2 (en) | 2010-03-22 | 2016-01-12 | University Court Of The University Of St. Andrews | Ruthenium complexes for use in olefin metathesis |
WO2013186238A1 (de) | 2012-06-13 | 2013-12-19 | Basf Se | Verfahren zur herstellung makrocyclischer ketone |
US8940940B2 (en) | 2012-06-13 | 2015-01-27 | Basf Se | Process for preparing macrocyclic ketones |
US10589511B2 (en) | 2014-10-21 | 2020-03-17 | Stratasys Ltd. | Three-dimensional inkjet printing using ring-opening metathesis polymerization |
WO2016063282A1 (en) | 2014-10-21 | 2016-04-28 | Stratasys Ltd. | Three-dimensional inkjet printing using ring-opening metathesis polymerization |
US10259210B2 (en) | 2014-10-21 | 2019-04-16 | Statasys Ltd. | Three-dimensional inkjet printing using ring-opening metathesis polymerization |
US11097529B2 (en) | 2014-10-21 | 2021-08-24 | Stratasys Ltd. | Three-dimensional inkjet printing using ring-opening metathesis polymerization |
WO2017134674A1 (en) | 2016-02-05 | 2017-08-10 | Stratasys Ltd. | Three-dimensional inkjet printing using ring-opening metathesis polymerization |
US11001725B2 (en) | 2016-02-05 | 2021-05-11 | Stratasys Ltd. | Three-dimensional inkjet printing using ring-opening metathesis polymerization |
US11173653B2 (en) | 2016-02-05 | 2021-11-16 | Stratasys Ltd. | Three-dimensional inkjet printing using polyamide-forming materials |
US11655386B2 (en) | 2016-02-05 | 2023-05-23 | Stratasys Ltd. | Three-dimensional inkjet printing using ring-opening metathesis polymerization |
WO2017134673A1 (en) | 2016-02-07 | 2017-08-10 | Stratasys Ltd. | Three-dimensional printing combining ring-opening metathesis polymerization and free radical polymerization |
US11179879B2 (en) | 2016-02-07 | 2021-11-23 | Stratasys Ltd. | Three-dimensional printing combining ring-opening metathesis polymerization and free radical polymerization |
WO2017187434A1 (en) | 2016-04-26 | 2017-11-02 | Stratasys Ltd. | Three-dimensional inkjet printing using ring-opening metathesis polymerization |
US11118004B2 (en) | 2016-04-26 | 2021-09-14 | Stratasys Ltd. | Three-dimensional inkjet printing using ring-opening metathesis polymerization |
Also Published As
Publication number | Publication date |
---|---|
DE19815275B4 (de) | 2009-06-25 |
EP1087838A1 (de) | 2001-04-04 |
JP2002510658A (ja) | 2002-04-09 |
IL138595A0 (en) | 2001-10-31 |
US7652145B2 (en) | 2010-01-26 |
US20150038723A1 (en) | 2015-02-05 |
EP1087838B1 (de) | 2005-05-25 |
US20050013150A2 (en) | 2005-01-20 |
US6635768B1 (en) | 2003-10-21 |
DE59912097D1 (de) | 2005-06-30 |
US8153810B2 (en) | 2012-04-10 |
US20110282068A1 (en) | 2011-11-17 |
IL138595A (en) | 2004-08-31 |
US20080009598A1 (en) | 2008-01-10 |
US7294717B2 (en) | 2007-11-13 |
US20050107626A1 (en) | 2005-05-19 |
JP4531253B2 (ja) | 2010-08-25 |
DE19815275A1 (de) | 1999-10-07 |
US7378528B2 (en) | 2008-05-27 |
US20040095792A1 (en) | 2004-05-20 |
US20080207911A1 (en) | 2008-08-28 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
WO1999051344A1 (de) | Alkylidenkomplexe des rutheniums mit n-heterozyklischen carbenliganden; verwendung als hochaktive, selektive katalysatoren für die olefin-metathese | |
EP1022282B1 (de) | Homo- und heterobimetallische Alkylidenkomplexe des Rutheniums mit N-heterocyclischen Carbenliganden und deren Anwendung als hochaktive, selektive Katalysatoren für die Olefin-Metathese | |
DE69631769T2 (de) | Ruthenium und osmium metallcarben-komplexe mit hoher metathese-aktivitat | |
DE69733830T2 (de) | Synthese von ruthenium- oder osmium-metathesekatalysatoren | |
Suzuki et al. | Selective carbon-carbon bond cleavage of cyclopentadiene on a trinuclear ruthenium pentahydride complex | |
EP2260047B2 (de) | Verfahren zur herstellung von ruthenium-carben-komplexen | |
CA2312755A1 (en) | Highly active cationic ruthenium and osmium complexes for olefin metathesis reactions | |
CN101205242A (zh) | 含有n-杂环卡宾配体的钌的亚烷基络合物及其在烯烃复分解反应中作为高活性高选择性催化剂的用途 | |
Pombeiro et al. | Reactions of 1-alkynes with trans-[ReCl (N 2)(Ph 2 PCH 2 CH 2 PPh 2) 2]: preparation of the vinylidene compounds trans-[ReCl ([double bond, length half m-dash] C [double bond, length half m-dash] CHR)(Ph 2 PCH 2 CH 2 PPh 2) 2](R= alkyl or aryl) and X-ray structure of trans-[ReCl ([double bond, length half m-dash] C [double bond, length half m-dash] CHPh)(Ph 2 PCH 2 CH 2 PPh 2) 2] | |
EP1005476B1 (de) | Verfahren zur herstellung von rutheniumkomplexen | |
WO2011026809A1 (de) | Chirale metallkomplexe und deren verwendung als katalysator in der synthese organischer verbindungen | |
DE10039389A1 (de) | Carbenoide enthaltende Rutheniumkomplexe | |
DE60206262T2 (de) | Neues verfahren zur herstellung von metall-carben-komplexen | |
DE10010046A1 (de) | Verfahren zur Herstellung von Aminen und neue Amine | |
Arena et al. | Half-sandwich ruthenium (II) and rhodium (III) complexes bearing chiral amino-phosphoramidite ligands: Synthesis, characterization and application in asymmetric transfer hydrogenation of acetophenone | |
Werner et al. | Vinylidene transition-metal complexes: I. Novel rhodium (I) and rhodium (III) complexes containing alkynes, alkynyls, and vinylidenes as ligands. Crystal structure of IC5H5Rh ( C CHPh)(PPri3) |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AK | Designated states |
Kind code of ref document: A1 Designated state(s): IL JP US |
|
AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
DFPE | Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101) | ||
WWE | Wipo information: entry into national phase |
Ref document number: 1999910357 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 138595 Country of ref document: IL |
|
WWE | Wipo information: entry into national phase |
Ref document number: 09647742 Country of ref document: US |
|
WWP | Wipo information: published in national office |
Ref document number: 1999910357 Country of ref document: EP |
|
WWG | Wipo information: grant in national office |
Ref document number: 1999910357 Country of ref document: EP |