CA2504418A1 - Process for preparing palladium(0) compounds - Google Patents
Process for preparing palladium(0) compounds Download PDFInfo
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- CA2504418A1 CA2504418A1 CA002504418A CA2504418A CA2504418A1 CA 2504418 A1 CA2504418 A1 CA 2504418A1 CA 002504418 A CA002504418 A CA 002504418A CA 2504418 A CA2504418 A CA 2504418A CA 2504418 A1 CA2504418 A1 CA 2504418A1
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- Prior art keywords
- alkyl
- unsubstituted
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Classifications
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- 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
- C07F15/006—Palladium compounds
-
- 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
Abstract
The invention relates to a method for the production of a compound containin g palladium (0), which consists in reacting a palladium compound with one or several compounds of general (I), (II), (III). The compounds containing palladium (0) are suitable for use as homogeneous catalysts, as precursors i n the in situ production of homogeneous catalysts or as precursors in the production of heterogeneous catalysts.
Claims (23)
1. Process for preparing a Palladium(0) compound, comprising reaction of a palladium compound with one or more compounds of the general formula I in the presence of a base:
in which:
each A is independently a CR7R8-radical where one of the A radicals may be oxygen, sulphur, an NR9 group or an SiR10R11 group, or where the A radicals may be a constituent of a 5- to 20-membered ring system, x is an integer from 2 to 4, and each R1 to R11 is independently selected from R, OR, halogen, CN, NO2, NR2, C (O) R, C (O) OR, OC (O) R, CONR2, NHCO2R, NHCOR, CH=CH-CO2R, Si (R) 3, Si (OR) 3, SiR (OR) 2, SiR2 (OR), SO3R, SO2R, SOR, SR, PR2, POR2, PO3H, PO(OR)2, in which R is a hydrogen atom, a substituted or unsubstituted C1-10-alkyl radical, a substituted or unsubstituted, mono- or polyunsaturated C1-10-alkenyl radical, or a substituted or unsubstituted, optionally heteroatom-containing C5-10-aryl radical, and the substituents on the alkyl radical or the alkenyl radical are selected from halogen, O-C1-10-alkyl, phenyl, O-phenyl, OH, NH2 and halogenated C1-10-alkyl, and the substituents on the aryl radical are selected from halogen, C1-10-alkyl, O-C1-10-alkyl, phenyl, O-phenyl, OH, NH2 and halogenated C1-10-alkyl, where R2 and R3 and/or R5 and R6 together with the carbon atoms bonded thereto may be a constituent of a 5- to 7-membered, optionally heteroatom-containing ring.
in which:
each A is independently a CR7R8-radical where one of the A radicals may be oxygen, sulphur, an NR9 group or an SiR10R11 group, or where the A radicals may be a constituent of a 5- to 20-membered ring system, x is an integer from 2 to 4, and each R1 to R11 is independently selected from R, OR, halogen, CN, NO2, NR2, C (O) R, C (O) OR, OC (O) R, CONR2, NHCO2R, NHCOR, CH=CH-CO2R, Si (R) 3, Si (OR) 3, SiR (OR) 2, SiR2 (OR), SO3R, SO2R, SOR, SR, PR2, POR2, PO3H, PO(OR)2, in which R is a hydrogen atom, a substituted or unsubstituted C1-10-alkyl radical, a substituted or unsubstituted, mono- or polyunsaturated C1-10-alkenyl radical, or a substituted or unsubstituted, optionally heteroatom-containing C5-10-aryl radical, and the substituents on the alkyl radical or the alkenyl radical are selected from halogen, O-C1-10-alkyl, phenyl, O-phenyl, OH, NH2 and halogenated C1-10-alkyl, and the substituents on the aryl radical are selected from halogen, C1-10-alkyl, O-C1-10-alkyl, phenyl, O-phenyl, OH, NH2 and halogenated C1-10-alkyl, where R2 and R3 and/or R5 and R6 together with the carbon atoms bonded thereto may be a constituent of a 5- to 7-membered, optionally heteroatom-containing ring.
2. Process according to Claim 1, wherein x is 3.
3. Process according to either of the preceding claims, wherein R1 to R6 are each hydrogen atoms.
4. Process according to any of the preceding claims, wherein -(A)x- is a group of the formula -CH2-X-CH2- and -X- is selected from -O-, -S-, -SiR2-, -NR- and -NC(O)R, and R is hydrogen, a C1-4 -alkyl radical or a halogenated C1-4-alkyl.
5. Process according to Claim 1, wherein the compound of the general formula I is selected from 1,5-hexadiene, 1,6-heptadiene and 1,7-octadiene.
6. Process according to Claim 1, wherein the compound of the general formula I is selected from diallyl ether, diallylamine, diallylmethylamine, diallylethylamine, N-acetyldiallylamine, diallyl sulphide, diallylsilane, diallyldimethylsilane, difurfuryl ether, difurfurylamine, bis(thiophen-2-ylmethyl)amine, difurfuryl sulphide and 1,3-divinylbenzene.
7. Process for preparing a Palladium(0) compound, comprising reaction of a palladium compound with one or more compounds of the general formula II in the presence of a base:
in which:
n is an integer from 3 to 20, each R13 to R15 is independently selected from R, OR, halogen, CN, NO2, NR2, C(O)R, C(O)OR, OC(O)R, CON R2, NHCO2R, NHCOR, CH=CH-CO2R, Si(R)3, Si(OR)3, SiR(OR)2, SiR2(OR), SO3R, SO2R, SOR, SR, PR2, POR2, PO3H, PO(OR)2, in which R is hydrogen, a substituted or unsubstituted C1-10-alkyl radical, a substituted or unsubstituted, mono- or polyunsaturated C1-10-alkenyl radical, or a substituted or unsubstituted, optionally heteroatom-containing C5-10-aryl radical, and the substituents on the alkyl radical or the alkenyl radical are selected from halogen, O-C1-10-alkyl, phenyl, O-phenyl, OH, NH2 and halogenated C1-10-alkyl, and the substituents on the aryl radical are selected from halogen, C1-10-alkyl, O-C1-10-alkyl, phenyl, O-phenyl, OH, NH2 and halogenated C1-10-alkyl, where R13 and R14 together with the carbon atoms bonded thereto may be a constituent of a 5- to 7-membered, optionally heteroatom-containing ring, and each R12 is independently selected from hydrogen, a hydroxyl group, a substituted or unsubstituted C1-10-alkyl radical, an -O-C1-10-alkyl radical (where the alkyl radical may be substituted or unsubstituted), a substituted or unsubstituted, mono- or polyunsaturated C1-10-alkenyl radical or a substituted or unsubstituted, optionally heteroatom-containing C5-10-aryl radical, where the substituents are as defined for R13 and R15.
in which:
n is an integer from 3 to 20, each R13 to R15 is independently selected from R, OR, halogen, CN, NO2, NR2, C(O)R, C(O)OR, OC(O)R, CON R2, NHCO2R, NHCOR, CH=CH-CO2R, Si(R)3, Si(OR)3, SiR(OR)2, SiR2(OR), SO3R, SO2R, SOR, SR, PR2, POR2, PO3H, PO(OR)2, in which R is hydrogen, a substituted or unsubstituted C1-10-alkyl radical, a substituted or unsubstituted, mono- or polyunsaturated C1-10-alkenyl radical, or a substituted or unsubstituted, optionally heteroatom-containing C5-10-aryl radical, and the substituents on the alkyl radical or the alkenyl radical are selected from halogen, O-C1-10-alkyl, phenyl, O-phenyl, OH, NH2 and halogenated C1-10-alkyl, and the substituents on the aryl radical are selected from halogen, C1-10-alkyl, O-C1-10-alkyl, phenyl, O-phenyl, OH, NH2 and halogenated C1-10-alkyl, where R13 and R14 together with the carbon atoms bonded thereto may be a constituent of a 5- to 7-membered, optionally heteroatom-containing ring, and each R12 is independently selected from hydrogen, a hydroxyl group, a substituted or unsubstituted C1-10-alkyl radical, an -O-C1-10-alkyl radical (where the alkyl radical may be substituted or unsubstituted), a substituted or unsubstituted, mono- or polyunsaturated C1-10-alkenyl radical or a substituted or unsubstituted, optionally heteroatom-containing C5-10-aryl radical, where the substituents are as defined for R13 and R15.
8. Process according to Claim 7, wherein n is an integer from 3 to 6 and each R12 is independently a C1-4-alkyl radical or a halogenated C1-4-alkyl radical.
9. Process for preparing a Palladium(0) compound, comprising reaction of a palladium compound with one or more compounds of the general formula III
in the presence of a base:
Term-O-{[Si(R16)(CR19CR17R18)O]v[Si(R20)2O]w}-Term (III) in which v and w are each independently 0 or an integer of from 1 to 1000 and v+w is from 0 to 1000, each R16 is independently selected from hydrogen, a hydroxyl group, a substituted or unsubstituted C1-10-alkyl radical, an -O-C1-10-alkyl radical (where the alkyl radical may be substituted or unsubstituted), a substituted or unsubstituted, mono- or polyunsaturated C1-10-alkenyl radical or a substituted or unsubstituted, optionally heteroatom-containing C5-10-aryl radical, where the substituents are as defined for R17 and R19, each R17 to R19 is independently selected from R, OR, halogen, CN, NO2, NR2, C(O)R, C(O)OR, OC(O)R, CONR2, NHCO2R, NHCOR, CH=CH-CO2R, Si(R)3, Si(OR)3, SiR(OR)2, SiR2(OR), SO3R, SO2R, SOR, SR, PR2, POR2, PO3H, PO(OR)2, in which R is a hydrogen atom, a substituted or unsubstituted C1-10-alkyl radical, a substituted or unsubstituted, mono- or polyunsaturated C1-10-alkenyl radical, or a substituted or unsubstituted, optionally heteroatom-containing C5-10-aryl radical, and the substituents on the alkyl radical or the alkenyl radical are selected from halogen, O-C1-10-alkyl, phenyl, O-phenyl, OH, NH2 and halogenated C1-10-alkyl, and the substituents on the aryl radical are selected from halogen, C1-10-alkyl, O-C1-10-alkyl, phenyl, O-phenyl, OH, NH2 and halogenated C1-10-alkyl, where R17 and R19 together with the carbon atoms bonded thereto may be a constituent of a 5- to 7-membered, optionally heteroatom-containing ring, each R20 is independently selected from hydrogen, a hydroxyl group, a substituted or unsubstituted C1-10-alkyl radical, an -O-C1-10-alkyl radical (where the alkyl radical may be substituted or unsubstituted), a substituted or unsubstituted, mono- or polyunsaturated C1-10-alkenyl radical, or a substituted or unsubstituted, optionally heteroatom-containing C5-10-aryl radical, where the substituents are as defined for R17 and R19, and each Term is independently (R16) 2 (CR17R18CR19) Si- or (R16)3Si-.
in the presence of a base:
Term-O-{[Si(R16)(CR19CR17R18)O]v[Si(R20)2O]w}-Term (III) in which v and w are each independently 0 or an integer of from 1 to 1000 and v+w is from 0 to 1000, each R16 is independently selected from hydrogen, a hydroxyl group, a substituted or unsubstituted C1-10-alkyl radical, an -O-C1-10-alkyl radical (where the alkyl radical may be substituted or unsubstituted), a substituted or unsubstituted, mono- or polyunsaturated C1-10-alkenyl radical or a substituted or unsubstituted, optionally heteroatom-containing C5-10-aryl radical, where the substituents are as defined for R17 and R19, each R17 to R19 is independently selected from R, OR, halogen, CN, NO2, NR2, C(O)R, C(O)OR, OC(O)R, CONR2, NHCO2R, NHCOR, CH=CH-CO2R, Si(R)3, Si(OR)3, SiR(OR)2, SiR2(OR), SO3R, SO2R, SOR, SR, PR2, POR2, PO3H, PO(OR)2, in which R is a hydrogen atom, a substituted or unsubstituted C1-10-alkyl radical, a substituted or unsubstituted, mono- or polyunsaturated C1-10-alkenyl radical, or a substituted or unsubstituted, optionally heteroatom-containing C5-10-aryl radical, and the substituents on the alkyl radical or the alkenyl radical are selected from halogen, O-C1-10-alkyl, phenyl, O-phenyl, OH, NH2 and halogenated C1-10-alkyl, and the substituents on the aryl radical are selected from halogen, C1-10-alkyl, O-C1-10-alkyl, phenyl, O-phenyl, OH, NH2 and halogenated C1-10-alkyl, where R17 and R19 together with the carbon atoms bonded thereto may be a constituent of a 5- to 7-membered, optionally heteroatom-containing ring, each R20 is independently selected from hydrogen, a hydroxyl group, a substituted or unsubstituted C1-10-alkyl radical, an -O-C1-10-alkyl radical (where the alkyl radical may be substituted or unsubstituted), a substituted or unsubstituted, mono- or polyunsaturated C1-10-alkenyl radical, or a substituted or unsubstituted, optionally heteroatom-containing C5-10-aryl radical, where the substituents are as defined for R17 and R19, and each Term is independently (R16) 2 (CR17R18CR19) Si- or (R16)3Si-.
10. Process according to Claim 9, wherein the compound of the general formula (III) has the general formula:
Term-O- [Si (R16) (CR19CR17R18)O]v -Term where R16 to R19, Term and v are each as defined in Claim 9.
Term-O- [Si (R16) (CR19CR17R18)O]v -Term where R16 to R19, Term and v are each as defined in Claim 9.
11. Process according to any of Claims 7 to 10, wherein the compound of the general formula II or III is selected from divinyldisiloxane, 1,1,3,3-tetramethyl-1,3-divinyldisiloxane, 1,1,3,3-tetra-methyl-1,3-dithien-2-yldisiloxane, 1,1,3,3-tetra-methoxy-1,3-divinyldisiloxane, 1,3-dimethyl-1,3-divinyldisiloxanediol, 1,3,5,7-tetravinyl-1,3,5,7-tetramethylcyclotetrasiloxane and 1,3,5-trimethyl-1,3,5-trivinylcyclotrisiloxane.
12. Process according to any of Claims 7 to 10, wherein the compound of the general formula II or III is selected from 1,1,3,3-tetramethyl-1,3-divinyldisiloxane, 1,3,5,7-tetravinyl-1,3,5,7-tetramethylcyclotetrasiloxane and 1,3,5-trimethyl-1,3,5-trivinylcyclotrisiloxane.
13. Process according to any of the preceding claims, wherein the palladium compound is selected from PdX2, PdX4, M2PdX4, M2PdX6, (NH3)2PdX2 and [Pd(NH3)4]X2, where M is a hydrogen atom, an alkali metal or NR*4+ (R* = hydrogen, C1-4-alkyl) and X is a halogen or NO3-.
14. Process according to Claim 13, wherein X is chlorine.
15. Process according to any of the preceding claims, wherein the reaction is effected in the presence of a solvent or solvent mixture.
16. Process according to Claim 15, wherein the solvent is selected from water, C1-6-alcohols and C2-6-ethers and mixtures thereof.
17. Process according to any of the preceding claims, wherein the base is selected from alkali metal salts, alkaline earth metal salts and ammonium salts (ammonium as NR9+ where R = H or C1-9-alkyl) of carbonates, hydrogencarbonates and hydroxides.
18. Process according to any of the preceding claims, also comprising a purification step.
19. Process according to any of the preceding claims, also comprising a concentration step.
20. Process according to any of the preceding claims, wherein the reaction of the palladium compound with one or more compounds of the general formula I, II or III is carried out in the presence of one or more ligands other than the compound of the general formula I, II or III.
21. Process according to any of the preceding claims, further comprising the reaction of the palladium compound with one or more ligands other than the compound of the general formula I, II or III.
22. Palladium(0) compound obtainable by a process according to Claim 1, wherein the compound of the general formula I is hexadiene or octadiene.
23. Palladium(0) compound obtainable by a process according to Claim 9, wherein the compound of the general formula III is 1,3,5,7-tetravinyl-1,3,5,7-tetramethylcyclotetrasiloxane.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10250901A DE10250901A1 (en) | 2002-10-31 | 2002-10-31 | Process for the preparation of palladium (0) -containing compounds |
| DE10250901.8 | 2002-10-31 | ||
| PCT/EP2003/012085 WO2004039819A2 (en) | 2002-10-31 | 2003-10-30 | Method for the production of compounds containing palladium (0) |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2504418A1 true CA2504418A1 (en) | 2004-05-13 |
| CA2504418C CA2504418C (en) | 2012-04-03 |
Family
ID=32115068
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2504418A Expired - Fee Related CA2504418C (en) | 2002-10-31 | 2003-10-30 | Process for preparing palladium(0) compounds |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US7615659B2 (en) |
| EP (1) | EP1558621B1 (en) |
| JP (1) | JP4914007B2 (en) |
| KR (1) | KR101046153B1 (en) |
| CN (1) | CN100500680C (en) |
| AT (1) | ATE384730T1 (en) |
| AU (1) | AU2003287975A1 (en) |
| CA (1) | CA2504418C (en) |
| DE (2) | DE10250901A1 (en) |
| IL (1) | IL168278A (en) |
| RU (1) | RU2334754C2 (en) |
| WO (1) | WO2004039819A2 (en) |
| ZA (1) | ZA200503426B (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2640038T3 (en) | 2009-05-06 | 2017-10-31 | Johnson Matthey Public Limited Company | Preparation of a metal complex |
| EP2743273A1 (en) | 2012-12-12 | 2014-06-18 | Umicore AG & Co. KG | Process for the preparation of aqueous preparations of complexes of platinum group metals |
| KR101747766B1 (en) * | 2013-03-14 | 2017-06-15 | 고쿠리츠켄큐카이하츠호진 상교기쥬츠 소고켄큐쇼 | Metal complex and supported metal complex having disiloxane as ligand, method for production thereof, and supported metal catalyst prepared by using the same |
| EP3478696B1 (en) * | 2016-07-04 | 2020-04-15 | Heraeus Deutschland GmbH & Co. KG | Method for the preparation of tetrakis (trihydrocarbylpho phine) palladium (0) |
| JP6786471B2 (en) * | 2017-12-15 | 2020-11-18 | キヤノン株式会社 | Reducing gas sensor |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1428552A (en) * | 1972-02-16 | 1976-03-17 | Gen Electric | Platinum complexes of unsaturated siloxanes and platinum containing organopolysiloxanes |
| JPS5186451A (en) * | 1974-12-09 | 1976-07-29 | Air Prod & Chem | Bisu * shisu shisuushikurookuta 1 55 jen * hatsukin mataha parajiumunoseizoho |
| US4093837A (en) * | 1975-07-31 | 1978-06-06 | Westinghouse Electric Corp. | Oil circuit-breaker pump-assembly with improved shunting contact structure |
| JPS5921880B2 (en) * | 1977-04-26 | 1984-05-22 | 三菱化学株式会社 | New palladium complex compound and its production method |
| US4347232A (en) * | 1981-06-17 | 1982-08-31 | Fmc Corporation | Preparation of hydrogen peroxide from its elements |
| DE4020689A1 (en) * | 1990-06-29 | 1992-01-02 | Bayer Ag | PALLADIUM-CONTAINING CARALYST PREPARATION |
| DE59202001D1 (en) | 1991-04-10 | 1995-06-01 | Bayer Ag | Process for the arylation of olefins. |
| US6316380B1 (en) | 1998-09-10 | 2001-11-13 | University Of New Orleans Research & Technology Foundation | Catalyst system comprising transition metal and imidazoline-2-ylidene or imidazolidine-2-ylidene |
| US6455720B1 (en) * | 2000-06-28 | 2002-09-24 | Takasago International Corporation | 2,2(diarlyl)vinylphosphine compound, palladium catalyst thereof, and process for producing arylamine, diaryl, or arylalkyne with the catalyst |
| DE10051316A1 (en) * | 2000-10-17 | 2002-04-25 | Omg Ag & Co Kg | Process for the production of mono-, bi- or polyfunctional biarylene |
| DE10062577B4 (en) * | 2000-12-15 | 2006-06-29 | Umicore Ag & Co. Kg | Carbene-diene complexes of nickel, palladium and platinum |
-
2002
- 2002-10-31 DE DE10250901A patent/DE10250901A1/en not_active Ceased
-
2003
- 2003-10-30 CA CA2504418A patent/CA2504418C/en not_active Expired - Fee Related
- 2003-10-30 AU AU2003287975A patent/AU2003287975A1/en not_active Abandoned
- 2003-10-30 RU RU2005116671/04A patent/RU2334754C2/en not_active IP Right Cessation
- 2003-10-30 DE DE50309092T patent/DE50309092D1/en not_active Expired - Lifetime
- 2003-10-30 CN CNB2003801046322A patent/CN100500680C/en not_active Expired - Lifetime
- 2003-10-30 KR KR1020057007550A patent/KR101046153B1/en not_active IP Right Cessation
- 2003-10-30 WO PCT/EP2003/012085 patent/WO2004039819A2/en active IP Right Grant
- 2003-10-30 AT AT03779823T patent/ATE384730T1/en not_active IP Right Cessation
- 2003-10-30 US US10/533,492 patent/US7615659B2/en active Active
- 2003-10-30 JP JP2004547623A patent/JP4914007B2/en not_active Expired - Lifetime
- 2003-10-30 EP EP03779823A patent/EP1558621B1/en not_active Expired - Lifetime
-
2005
- 2005-04-28 IL IL168278A patent/IL168278A/en not_active IP Right Cessation
- 2005-04-28 ZA ZA200503426A patent/ZA200503426B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR20050083870A (en) | 2005-08-26 |
| RU2005116671A (en) | 2006-05-10 |
| JP4914007B2 (en) | 2012-04-11 |
| CA2504418C (en) | 2012-04-03 |
| DE10250901A1 (en) | 2004-05-19 |
| DE50309092D1 (en) | 2008-03-13 |
| ZA200503426B (en) | 2006-09-27 |
| US7615659B2 (en) | 2009-11-10 |
| JP2006504765A (en) | 2006-02-09 |
| EP1558621A2 (en) | 2005-08-03 |
| WO2004039819A3 (en) | 2004-10-21 |
| CN100500680C (en) | 2009-06-17 |
| AU2003287975A1 (en) | 2004-05-25 |
| KR101046153B1 (en) | 2011-07-04 |
| RU2334754C2 (en) | 2008-09-27 |
| US20060106239A1 (en) | 2006-05-18 |
| WO2004039819A2 (en) | 2004-05-13 |
| CN1720253A (en) | 2006-01-11 |
| ATE384730T1 (en) | 2008-02-15 |
| IL168278A (en) | 2012-06-28 |
| EP1558621B1 (en) | 2008-01-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20161031 |