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'the formula United States Patent Ofilice 3,015,680 Patented Jan. 2, 1962 3,015,680 PROCESS FOR THE MANUFACTURE OF CAROTENE. COMPOUNDS Otto Isler, Marc Montavou, and Rudolf Riiegg, Basel, and Paul Zeller, Neuallschwil, near Basel, Switzerland, assignors to Hoflfmann-La Roche Inc., Nutley, N.J., a corporation of New Jersey No Drawing. Filed June 21, 1956, Ser. No. 592,758
Claims priority, application Switzerland June 27, 1955 4 Claims. (Cl. 260-666) The present invention relates to a novel process for the manufacture of carotene compounds, more particularly to the manufacture of 15,l5'-dehydro-fi-carotene and El-carotene.
The hitherto known syntheses of fi-carotene invariably start from ,B-ionone. In a first synthesis according to Inhoifen this starting compound was used for synthesizing first a C -aldehyde which was added to acetylene dimagnesium bromide at both ends thereof A further synthesis according to Inholfen is based on the building scheme C +C +C =C in which two molecules of B-C -ketone are linked together by diacetylene. The other syntheses start from (E -acetylene compounds and octen-(4)-dione-(2,7). In all these syntheses C -acetylene diols or tetrols are formed as intermediates which must be dehydrated by cumbersome methods often resulting in very poor yields.
It has now been discovered that it is advantageous to build up the carbon skeleton of carotene by the new building scheme C +C +C =C without formation of hydroxylated intermediates.
The present invention thus relates to a new process for the manufacture of carotene compounds which comprises condensing l-bromomethyl-2,6,6-trimethyl l-cyclohexene (e.g. fi-cyclogeranyl bromide) with triaryl-phosphine in which the aryl groups may carry alkyl or alkoxy radicals, thereby producing a phosphonium bromide of reacting the latter with phenyllithium, thereby producing fit-cyclegeranylidene-triaryl-phosphine; a'nd condensing the latter with a dialdehyde selected from the group consisting of 2,6,11,15 -tetramethyl-2,4,6,l0,12,14-hexadeca- 8,10,12,l4-hexadecaheptaene-1,16-dia1.
In the first stage of the comprehensive process l-bromomethyl-2,6,6-trimethyl-l-cyclohexene is condensed with a triaryl-phosphine, preferably triphenylphosphine. The condensation is advantageously effected by mixing the reactants in an inert organic medium, such as benzene, until the condensation has been completed; usually after a somewhat extended reaction period of the order of two days. Preferably, the triarylphosphine is employed in slight molar excess, in relation to the bromo reactant. phosphonium bromide product, i.e. triaryl-[(2,6,6-trimethyl-l-cyclohexen-l-yl)methyl] phosphonium bromide, is filtered OE, washed and dried.
In the next'stage of the comprehensive process referred to, the phosphonium bromide intermediate is treated in order to split out hydrogen bromide therefrom. This reaction is advantageously effected by suspending the phosphonium bromide in an anhydrous ether, e.g. absolute diethyl ether, mixing the suspension with the 'stoichiometric quantity of an ethereal solution of phenyl- At the end of the condensation reaction, the
lithium or butyllithium, and heating the suspension. Upon heating, the suspended phosphonium salt goes into solution and there results a deep redto brown-colored solution of the triaryl-cyclogeranylidene phosphine, which solution can be used directly for the next stage of the process.
In said next stage, the solution of the triaryl-[(2,6,6- trimethyl-l-cyclohexen-l-yl)methylidene] phosphine is condensed with a C dialdehyde; and the resulting 'adduct or condensation product is decomposed by splitting out two molar proportions of triarylphosphine oxide therefrom. An advantageous mode of effecting this stage of the process comprises mixing the dialdehyde reactant with about two molar proportions (or preferably a slight excess thereover) of the triaryl-cyclogeranylidene-phosphine intermediate, in an inert organic liquid, such as diethyl ether, petroleum ether, benzene, dioxan, tetrahydrofuran and the like. Advantageously, the triaryl-cyclogeranylidene-phosphine and the C -dialdehyde reactant are mixed at room temperature or at moderately elevated temperature, taking precautions to exclude oxygen, for
example by displacing the oxygen with an inert gas such as nitrogen. The condensation reaction is-an exothermic reaction, which takes place practically instantaneously upon addition of a solution of the dialdehyde reactant to a solution of the phosphine reactant. Depending upon the specific identity and quantity of the solvent media, the adduct or condensation product remains in solution or precipitates; in the latter case the color of the solution becomes lighter. In a preferred mode of execution, the dialdehyde reactant, in solution in methylene chloride, is added to a suspension or solution of the phosphine reactant; in such manner that at least the the dialdehyde reactant and the resulting adduct are both in dissolved state. The adduct decomposes, gradually if allowed to stand in solution, and more quickly if its solution is heated, resulting in the formation of the C carotenoid and of triarylphosphine oxide as a byproduct. The decomposition can be effected very easily, preferably by heating the adduct, in solution in methylene chloride, for
several hours at a moderately elevated temperature, e.g.
40 50 C. At the end of the decomposition reaction, the C carotenoid formed can be obtained by shaking the organic phase with water and filtering off the triarylphosphine oxide, the C carotenoid being obtained by crystallization from the filtrate, after drying and concentrating the latter. If desired, the carotenoid product can be freed of any contaminating organic phosphorus compounds by recrystallization, partition between solvents, or chromatography. An advantageous method of purifying the C carotenoid comprises mixing the filtrate, above referred to, with a large quantity of ethanol or methanol, whereupon the carotenoid precipitates in crystalline form, while the byproducts remain in solution. If the carotenoid product contains a triple bond at the 15,15 position, the latter can be partially hydrogenated and the hydrogenation product can be isomerized to the trans form by methods known per se. For example, 15,l5-dehydro-;8-carotene can be catalytically hydrogenated, in an inert solvent such as ethyl acetate, toluene or petroleum ether, in the presence of a selective hydrogenation catalyst, e.g., a palladium-lead catalyst in the presence of quinoline, of the type disclosed in the publication Helvetica Chimica Acta, 35, 446 (1952). The l5,15'-cis compound formed by the hydrogenation operation can be isomerized to the corresponding trans compound by any of the known methods for effecting this type of isomerization, preferably by heating a solution of the l5,15-cis compound.
In one of its embodiments, the invention provides a process for the preparation of ,B-carotene which comprises condensing 1-bromomethyl-2,6,6-trimethyl-cyclohexene with triphenylphosphine, thereby producing triphenyl [(2,6,6 trimethyl 1 cyclohexen 1 yl)- methyl1-phosphonium bromide; reacting the latter with phenyllithium, thereby producing triphenyl-[(2,6,6-trimethyll-cyclohexenl-yl) -methylidene -pl1osphine; condensing the latter with 2,6,11,l-tetramethyl-2,4,6,10,12, 14-hexadecahexaen-8-yne-1-,16-dial and decomposing the resulting adduct, thereby producing 15,15-dehydro-pcarotene; hydrogenating the latter, thereby producing 15, 15'-cis-,8-carotene; and isomerizing the 15,15-cis linkage of the latter to a trans linkage.
In another of its embodiments, the invention provides a process which comprises partially hydrogenating 2,6,11, 15 tetramethyl 2,4,6,10,12,14 hexadecahexaen 8- yne-1-,16-dial, thereby producing 2,6,11,15-tetramethyl- 2,4,6,8,10,12,14 hexadecaheptaene 1,16 dial; and condensing the latter with triphenyl-[ (2,6,6-trimethyl-l-cyclohexen-1-yl)methylidene]-phosphine and decomposing the resulting adduct, thereby producing all-trans-fi-carotene.
The invention is further illustrated by the following examples, which are illustrative but not limitative thereof. Temperatures are stated in degrees centigrade, uncorrected.
Example .1
Over a period of one hour, 5.2 g. of l-bromomethyl- 2,6,6-trimethyl-l-cyclohexene (B-cyclogeranyl bromide) was added, with stirring, to a solution of 7 g. of triphenylphosphine in 40 ml. of benzene, at room temperature. The reaction mixture was stirred for 48 hours after all the bromo reactant had been added. The solid material formed was filtered ofif, washed with benzene and petroleum ether in turn, then was dried at 40 under a water pump vacuum. 7.5 g. of the triphenyl-[(2,6,6- trimethyl-l-cyclohexen-l-yl)methyl] phosphoniurn bromide so obtained (M.P. 90-93) was suspended in 80 ml. of absolute diethyl ether and reacted with a solution of 1.2 of phenyllithium in 15 ml. of absolute diethyl ether, by heating and stirring. The suspended material lost hydrogen bromide and dissolved to form a deep red solution of triphenyl-[(2,6,6-trimethyl 1 cyclohexen 1- yl)methylidene]-phosphine, which was diluted by addition of a further quantity of absolute diethyl ether to a total volume of 100 ml. and used directly for the procedure described in the next paragraph.
To the deep red solution of triphenyl-[(2,6,6-trimethyll-cyclohexen-l-yl)methylidene]-phosphine in 100 ml. of absolute diethyl ether, obtained as described above, was added dropwise, while stirring and in a nitrogen atmosphere, a solution of 2 g. of 2,6,11,15-tetramethyl-2,4,6, 10,12,l4-hexadecahexaen-8-yne-1,16-dial in 200 ml. of dry benzene. From asolution, which at first was dark brown, there precipitated a red-brown material, which upon heating at 60 for about six hours was partially redissolved. The warm solution was filtered and washed with benzene until the eluate was only weakly colored. The filtrate was washed neutral with water, dried over sodium sulfate and concentrated in vacuo. The residue was mixed with ethanol, thereby precipitating 15,15-dehydro-B-carotene in fine leaflets. The material was recrystallized from methylene chloride, resulting in a purifiedproduct of M.P. 156, U.V. maxima at 432 m and 456 my,
E} 2015 and 16.65
(in petroleum ether). The 15,15'-dehydro-;8-carotene was converted to 15,l5'-mono-cis- 3-carotene by catalytic hydrogenation in petroleum ether in the presence of a palladium catalyst partially inactivated with quinoline and lead (as specifically disclosed in Helvetica Chimica Acta, 35 (1952), at page 450). The hydrogenation ceased upon uptake of one molar proportion ,of hydrogen. The reaction mixture was filtered, and the filter cake was dissolved in methylene chloride. The catalyst, which remained insoluble in methylene chloride, was filtered ofl,
and the filtrate was concentrated, thereby precipitating 15,l5-mono-cis-fi-carotene, M.P. 150151. The latter was isomerized, by heating at in petroleum ether, to all-trans-B-carotene, M.P. 180, U.V. maxima at 453 my. and 48 0 III/L,
El 2560 and 2230 (in petroleum ether).
The C dialdehyde, 2,6,11,15tetramethyl-2,4,6,10,12, 14-hexadecahexaen-8-yne-1,16-dial, used as a reactant in this example, was prepared as follows:
10 g. of 2,7-dimethyl-2,6-octadien-4-yne-1,8-diol was dissolved in 1500 ml. of dry acetone; g. of manganese dioxide (prepared according to J. Chem. Soc., 1952, 1094) was added and the mixture was shaken mechanically for 2 hours. The manganese dioxide was sucked otf, washed with acetone until the filtrate ran off nearly colorless, and then the yellow acetone solution wos concentrated in vacuo. Approximately 9.7 g. of a solid, yellow residue was obtained, which was recrystallized from ether/ petroleum ether. The 2,7-dimethyl-2,6-octadien-4- yne-1,8-dial had M.P. 68; ultra-violet maxima in ethanol at 314 m, (e=29,000) and 330 m (e=26,200).
To a hot solution of 40 g. of 2,7-dimethyl-2,6-octadien- 4-yne-1,8-dial in 120 g. of ethyl orthoformate was added a hot solution of 4 g. of ammonium nitrate in 50 ml. of absolute ethanol, and the mixture was allowed to stand for 48 hours, the mixture thus gradually reaching room temperature. Then the reaction mixture was taken up in diethyl ether, washed with dilute aqueous sodium bicarbonate solution and dried over potassium carbonate. After concentration of the ether solution, the excess of ethyl orthoformate as well as ethyl formate produced by reaction was removed from the condensation product in vacuo. By distillation in a high vacuum there was obtained pure 2,7-dimethyl-2,6-octadien-4-yne-1,8-tetraethyldiacetal, B.P. 122 to 127 at 0.03 mm.; 71 1.4892; ultraviolet maxima: 273 m e=27,200, and 288 my, e=22,600 (in come. ethanol).
To a mixture of 102 g. of 2,7-dimethyl-2,6-oetadien- 4-yne-1,8-tetraethyldiacetal and 0.5 ml. of boron trifluoride etherate was gradually added 47 g. of ethyl vinyl ether, while stirring. The rate of addition was so adjusted that the reaction temperature was maintained between 30 and 35. The mixture was stirred for a further period of 3 hours at 35, and was then taken up in diethyl ether, washed with dilute aqueous sodium hydroxide solution and dried over potassium carbonate. After concentration of the ether solution, 137 g. of crude 3,10 diethoxy 4,9 dimethyl 4,8 dodecadien 6 yne- 1,12-tetraethyldiacetal was obtained. The compound, after purification by distillation in a high vacuum, had B.P. -161 at 0.03 mm.; n 1.4778; ultraviolet maxima: 274 m z, e=26,200, and 290m e=2 3,400 (in cone. ethanol).
In order to hydrolyze the above diacetal, the 137 g. of crude 3,.10- diethoxy-4,9-dimethyl-4,8-dodecadien-6- yne-l,12-tetraethyldiacetal was dissolved in a mixture of 800 ml. of dioxan, 200 ml. of water and 35 ml. of syrupy phosphoric acid (containing 87% by weight H PO and a trace of hydroquinone was added thereto. The mixture was boiled for 7 hours under a nitrogen atmosphere, during which period a mixture of dioxan, ethanol and water was slowly distilled off through a column packed with'Raschig rings. The reaction volume was maintained constant by dropwise addition of a mixture of dioxan and water. The .hot reaction mixture was then poured, with stirring, into 2000 ml. of ice water. Immediately 4,9- dimethyl 2,4,8,10 dodecatetraen-6-yne-1,12-dial precipitated in crystalline form.- The precipitate was sucked OE and washed well with water. After recrystallization from ethyl alcohol and drying in vacuo, 45 g. of th pure compound, M.P.. C., was obtained.
To a warm solution of 30 g. of 4,9- dimethy1.- 2,4,8,10- dodecatetraen-6-yne-1,12-dial in 100 g. of ethyl orthoformate was added a Warm solution of ,2 g. of ammonium nitrate in 100 ml. of absolute ethanol, and the mixture was heated until, on dilution, crystals of starting material no longer separated. The reaction mixture was then taken up in diethyl ether, and the solution was washed with dilute aqueous sodium bicarbonate solution and dried over potassium carbonate. After concentration of the ether'solution, the excess ethyl orthoformate as well as ethyl formate formed by reaction, were separated from the reaction mixture in vacuo. The residue was distilled in a high vacuum, yielding 4, 9-dimethyl- 2,4,8,l dodecatetraen-6-yne 1,12 tetraethyldiacetal, M.P. 181/0.04 mm.; 11 1.57; ultraviolet maxima: 330,, e=46400, and 350 :48300 (in ethanol).
To 45 g. of 4,9-dimethyl-2,4,8,10-dodecatetraen-6-yne- 1,12-tetraethyldiacetal and 0.5 g. of boron trifluoride etherate was added gradually, with stirring, 80 g. of ethyl propenyl ether. The rate of addition was so adjusted that the reaction temperature was maintained between 30 and 35 Stirring was continued for 3 hours at 35. Then the reaction mixture was taken up in diethyl ether, and the solution was washed with dilute aqueous sodium hydroxide solution and dried over potassium carbonate. Concentration of the ethereal solution yielded crude 3,14 diethoxy 2,6,11,15 tetramethyl- 4,6,10,12 hexadecatetraen-8-yne-l,16-tetraethyldiacetal, which had two absorption maxima in the ultraviolet spectrum, at 330, and 350,41. (in ethanol).
In other to effect hydrolysis, the crude 3,14-diethoxy- 2,6,11,15 tetramethyl 4,6,10,1Z-heXadecatetraen-S-yne- 1,16-tetraethyldiacetal was dissolved in a mixture of 300 ml. of dioxan, 60 ml. of water and 10 ml. of syrupy (87%) phosphoric acid, and a small amount of hydroquinone was added. The mixture was boiled under nitrogen for 7 hours; a mixture of dioxan, alcohol and water being thus distilled ofi from the reaction mixture through a column packed with Raschig rings. The volume of the reaction mixture was maintained constant by dropping a mixture of dioxan and water into the reaction mixture. The hot reaction mixture was then poured into ice water, with stirr ng, the 2,6,11,15-tetramethyl 2,4,6,10,l2,14 hexadecahexaen-S-yne-1,16-dial thus precipitating immediately in crystalline form. The precipitate was filtered with suction and thoroughly washed with water. The pure dialdehyde, having a melting point of 190 to 192", was obtained by recrystallization from a mixture of benzene and petroleum ether.
Example 2 50 g. of 2,6,11,15-tetramethyl-2,4,6,10,12,14-hexadecahexaen-8-yne-1,l6-dial was suspended in 600 ml. of toluene. 10 g. of a Pd-Pb--CaCO catalyst (as specifically disclosed in Helvetica Chimica Acta, 35, 446 (1952), at page 450) and 5 ml. of quinoline were added. The solution was reacted with elemental hydrogen, at room temperature and a very slight hydrogen overpressure, until the uptake of hydrogen ceased. The hydrogenation mixture was filtered, and the filter cake (containing catalyst and hydrogenation product) was washed with acetone in order to extract the hydrogenation product. The acetone solution yielded approximately 40 g. of 2,6,11,15-tetramethyl 2,4,6,8,10,12,14-hexadecaheptaene 1,16 dial, M.P. 190191, ultraviolet maxima at 408, 430 and 458 E} 2930, 5240 and 5820 (in petroleum ether).
To a deep red solution of triphenyl-[(2,6,6-trimethyl-1- cyclohexen-l-yl)methylidene]-phosphine in 100 ml. of absolute diethyl ether (obtained precisely as described in Example 1 above) was added dropwise, over a period of five minutes, while stirring and in a nitrogen atmosphere, a solution of 2 g. of 2,6,11,15-tetramethyl-2,4,6,- 8,10,12,14-hexadecaheptaen-1,16-dial in 50 ml. of methylene chloride. The reaction mixture was stirred for an additional period of 15 minutes at 30 and then was refluxcd for five hours. At the end of this time 60 ml. of
methanol was added to the warm reaction mixture and the whole was cooled to 10 while stirring. The crystal slurry was filtered in a carbon dioxide atmosphere and the filter cake of crude p-carotene was washed with 20 ml. of methanol. The crude ,B-carotene was dissolved in 30 ml. of methylene chloride, taking care that the temperature did not exceed 40, and then was precipitated from the warm methylene chloride solution by adding thereto 50 m1. of methanol and cooling for two hours with ice water. The slurry was filtered in a carbon dioxide atmosphere, the filter cake was washed with methanol and was then dried at 40 in vacuo. There was obtained all-trans-fi-carotene, identical with that obtained in Example 1 above.
We claim:
1. A process which comprises condensing l-bromomethyl-2,6,6-trimethyl-l-cyclohexene with triarylphosphine, thereby producing a triaryl-[(2,6,6-trimethyl-1- cyclohexen-l-yl)methyl]-phosphonium bromide; reacting the latter with phenyllithium, thereby producing a triaryl- [(2,6,6-trimethyl-1-cyclohexen-1-yl)-methylidene] phosphine; and condensing the latter with a dialdehyde selected from the group consisting of 2,6,11,15-tetramethyl- 2,4,6,10,12,14-hexadecahexaen-8-yne-1,16-dial and 2,6,11, 15-tetramethyl-2,4,6,8,10,12,14 hexadecaheptaene 1,16- dial.
2. A process for the preparation of B-carotene which comprises condensing 1-bromomethyl-2,6,6-trimethyl-1- cyclohexene with triphenylphosphine, thereby producing triphenyl [(2,6,6-trimethyl-l-cyclohexen-l-yl)methyl]- phosphonium bromide; reacting the latter with phenyllithium thereby producing triphenyl-[(2,6,6-trimethyl-1-cycloheXen-l-yl)methylidene1-phosphine; condensing the latter with 2,6,11,l5-tetramethyl-2,4,6,10,12,14-hexadecahexaen- 8-yne-1,16-dial and decomposing the resulting adduct, thereby producing 15,l5'-dehydro-fi-carotene; partially hydrogenating the latter, thereby producing 15, 15-cis-;8- carotene; and isomerizing the 15,15'-cis linkage of the latter to a trans linkage.
3. A process which comprises partially hydrogenating 2,6,1l,l5-tetramethyl-2,4,6,10,12,14 hexadecahexaen 8- yne-1,l6-dial, thereby producing 2,6,11,15-tetramethyl- 2,4,6,8,l0,12,14-hexadecaheptaene-1,16-dial; and condensing the latter with triphenyl-[(2,6,6-trimethyl-l-cyclohexen-1-yl-)methy1idene]-phosphine and decomposing the resulting adduct, thereby producing all-trans Si-carotene.
4. A process for the production of beta-carotene which comprises condensing beta-cyclogeranyl bromide with triphenylphosphine, thereby producing beta-cyclogeranyltriphenylphosphonium bromide; reacting the latter with phenyl-lithium to produce triphenyl-(2,6,6-trimethyl-l-cyclohexen-l-yl)-methylidene phosphine; and condensing the latter with 2,6,11,1S-tetramethylhexadecaheptaene-(2,4,6, 8,10,12,14)-dial-(1,16) and removing the triphenyl phosphine oxide from the reaction mixture.
References Cited in the file of this patent UNITED STATES PATENTS 2,437,797 Walling Mar. 16, 1948 2,584,112 Brown Feb. 5, 1952 2,609,396 ,Inhofien et al. Sept. 2, 1952 2,671,112 Inhoifen et al. Mar. 2, 1954 7. 7 Oppegard Aug. 24, 1954 2,745,877 Bindler et al. May 15, 1956 2,775,626 Schaaf et al. Dec. 25, 1956 OTHER REFERENCES Gridgeman: Chemistry and Industry (British), vol. 37, Sept. 13, 1947, pp. 555-58.
Kosolapoff: Organo-phosphorus Compounds (1950), I. Wiley & Sons, New York, N.Y., pp. 28, 78, 84 and 85 only.
Wittig et al.: Liebigs Annalen der Chemie, vol. 580, January 1953, p. 48.
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WAC Lighting QP-501-CH Quick Connect Socket Set, Chrome w/ 6" Cable
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The WAC Lighting QP-501-CH Socket Set in chrome with a 6" cable is used to hang G500 series glass pendants on multiple applications; accenting a variety of tabletops, counters, and dining room tables, in both residential and commercial applications. The socket set is compatible with these W.A.C. systems; Monorail, Flexrail, Track, Linear, Monopoint and Multipoint canopies and glass shade options (sold separately).
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{via but does it float}
reflections in the rain about a dream
{via but does it float}
At first i thought it was Richter!! Never heard of Stricher before i must say. But certainly someone to follow up.
If you click the link on the picture, you'll end up at the artist's Flickr site.
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Kukla's Korner Hockey
Category: NHL-Talk
BOG Meets Tomorrow
by Paul on 09/15/08 at 07:03 PM ET
Comments (0)
from Pierre LeBrun of ESPN,
The NHL's board of governors convenes tomorrow here in Toronto. I'll have the privilege of standing outside the meeting and trying to run after owners or team executives for a comment afterwards. Most of them will try to avoid us. It's always a mad scramble.
We were able to get our hands on some details from tomorrow's agenda:
1. There will obviously be an update on the ownership situation in Nashville, the league still reeling from the bank fraud charges laid on part-owner William "Boots" Del Biaggio III.
read on plus some Robert Lang talk…
Filed in: NHL Talk, | KK Hockey | Permalink
Kelly Leading The Pension Plan Fight
by Paul on 09/14/08 at 11:00 PM ET
Comments (0)
from David Shoalts of the Globe and Mail,
The latest pension court battle between the NHL and its players may look minor compared with the previous one, when the owners were caught with their hands in the till, but it will be a watershed moment for union boss Paul Kelly.
It is not important that he wins the fight, only that he is willing to wage it. By doing so, he should satisfy a small but influential group of his members who remain suspicious of anything that smacks of a cozy relationship with the NHL.
Filed in: NHL Talk, NHLPA, | KK Hockey | Permalink
Tags: paul+kelly
Seven Guys to Watch
by Alanah McGinley on 09/13/08 at 08:32 PM ET
Comments (0)
From Jason Kay at The Hockey News,
There are a handful of players – guys between the ages of 23 and 25 who've been in the league a few years and have had the opportunity to make a big splash – who have fallen short of expectations. It's their time to show whether they're going to enter an upper stratosphere or remain in the OK-range.
Here, in alphabetical order, are seven guys I'd like to see more from:
Kari Lehtonen, Atlanta, 24 (drafted second overall, 2002).
The Thrashers goalie was a two-time THN minor pro prospect of the year. His career goals-against average is a middling 2.82 and he has yet to win a playoff game.
Filed in: NHL Talk, | KK Hockey | Permalink
Finding A Way To Play
by Paul on 09/13/08 at 09:35 AM ET
Comments (0)
from Mark Zwolinski of the Toronto Star,
Former hockey enforcer Brandon Sugden will take his fight on the road – if he has to – to get a retirement rule altered so he can return to the league.
"I've got a call in to (NHL deputy commissioner) Bill Daly and I hope to talk to him, but if I can't I'm going to drive to New York and talk to him in person," Sugden said yesterday.
Sugden says he will hop into his truck Monday morning and head to New York if his reinstatement bid continues to stall through the weekend.
I heard the NHLPA's Glenn Healy on Toronto radio yesterday and he was asked what the NHLPA can do about this, Healy responded basically nothing. the five teams preventing him from attending the NYI camp would have to change their minds.
Filed in: NHL Talk, | KK Hockey | Permalink
Tags: brandon+sugden
Lindros Gives Back
by Paul on 09/12/08 at 10:02 PM ET
Comments (0)
from CBC,
Retired hockey player Eric Lindros is among the world's top 10 most generous celebrities.
Lindros made No. 9 on the list, which is compiled annually by The Giving Back Fund, after contributing $5 million to the London Health Sciences Centre, a London, Ont.-based hospital where he was treated.
Filed in: NHL Talk, | KK Hockey | Permalink
Tags: eric+lindros
Worry About North America First
by Paul on 09/12/08 at 06:27 PM ET
Comments (0)
from Ray Slover of the Sporting News,
Let's admit this much: An NHL presence in Europe makes sense, if only to fend off the Continental Hockey League (KHL). We don't need to see KHL czar Alexander Medvedev pounding a shoe at an IIHF conference to know there's a cold war on between the old boys of the western world and the mother Russians.
But the last thing the NHL needs to do is pull its attention away from its own nest. At the risk of sounding protectionist and isolationist—but yes, I am a bit ist about this—Gary Bettman's crew must take care of its own before it goes off on some overseas adventure.
Filed in: NHL Talk, | KK Hockey | Permalink
Afternoon Line
by Alanah McGinley on 09/12/08 at 05:39 PM ET
Comments (0)
"I think all your viewers know that hockey is the greatest game in the whole wide world. It's actually not a game. It's a religion. So I think you can understand it's a religious obligation to be involved in the game. It's fun, it's a passion. I play it regularly. I played it Friday night, and I'll play a couple of times this week. It's passion."
—Jim Balsillie speaking to Tech Check at CNBC this week, when asked about his continuing aspirations to own a NHL team
Filed in: NHL Talk, | KK Hockey | Permalink
Tags: jim+balsillie, rim
"Scampy" to the Hall of Fame
by Alanah McGinley on 09/12/08 at 03:21 PM ET
Comments (0)
From Evan Weiner at NHL.com:
Scapinello will be inducted into the Hockey Hall of Fame on Nov. 10 for his body of work, which included 2,500 regular-season games and 426 playoff games, all consecutive, as he never missed a game between 1971 and 2004. He was called the best linesman in the game in 20 of his 33 seasons; he worked 20 Stanley Cup Finals and three All-Star Games. He also worked the 1998 Winter Olympics. But according to Morel, Scapinello was one of those guys who made training camp fun.
"He juggled, he was pretty good," said Morel. "He was pretty agile. He was good on a one-wheeled bike. Sometimes he brought that to training camp and show us what he did during that summer to practice that balance and it was OK."
Of Note: Scapinello published a book last year titled, Between the Lines: Not-So-Tall Tales From Ray "Scampy" Scapinello's Four Decades in the NHL
Filed in: NHL Talk, NHL Officiating, | KK Hockey | Permalink
Tags: referees
Europe On The NHL Radar
by Paul on 09/12/08 at 10:58 AM ET
Comments (0)
from William Houston/David Shoalts of the Globe and Mail,
The NHL is aiming to have teams based in Europe within the next 10 years, the league's deputy commissioner said yesterday.
"As time goes on, you'll see us making increasing movement into Europe," Bill Daly said in an interview. "Certainly, it's a possibility that within 10 years time we will be playing games there."
Asked whether he viewed European expansion within 10 years as a good possibility, he said: "I hope so. But again, I think it's a long way between here and there. And I think all the pieces have to continue to line up in order for that to happen.
"So, certainly, we would hope that would be the case. But I can't say with any degree of certainty at this point."
Update 11:09am ET (alanah): From Pierre LeBrun at ESPN—
There remain hurdles, to be sure, serious ones. For starters, there's the issue of travel. That's obvious. But I believe the one issue that worries the NHL even more is European sports fans generally aren't used to paying the same kind of money for tickets as North Americans. Getting fans in Sweden, Finland, Switzerland, Russia, Germany, the Czech Republic, etc., to pay out bigger amounts for NHL games will be the real test if and when this ever comes to fruition.
Filed in: NHL Talk, | KK Hockey | Permalink
NHLPA Taking NHL to Court Regarding Pension Plan
by Alanah McGinley on 09/11/08 at 10:29 PM ET
Comments (0)
From TSN:
The NHL Players' Association hopes to see a pension dispute with the league solved in court.
The NHLPA announced Thursday that it had filed an application in the Ontario Superior Court of Justice regarding an interpretation of the league's pension plan.
The issue relates to the calculation of the death benefit for players with NHL service prior to July 1, 1986. The NHLPA believes widows and other beneficiaries of players who passed away before taking their pension were paid less than is required by law.
The NHL disagrees.
Filed in: NHL Talk, | KK Hockey | Permalink
Tags: nhlpa, pension+plan
« Previous ‹ First < 459 460 461 462 463 > Last › Next »
About Kukla's Korner Hockey
Paul Kukla founded Kukla's Korner in 2005 and the site has since become the must-read site on the 'net for all the latest happenings around the NHL.
From breaking news to in-depth stories around the league, KK Hockey is updated with fresh stories all day long and will bring you the latest news as quickly as possible.
Email Paul anytime at email@example.com
Most Recent Blog Posts
KK- How To Help Kukla's Korner
The Slumping Chicago Blackhawks Are Now A Wildcard Team
Vincent Lecavalier Just Wants To Play
The Minnesota Wild's Run To The Playoffs


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Ibis Styles Dahab Lagoon
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when twice, and wana go again
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Travel Blogs from Dahab
Egypt part 7: dahab part 2
... freediving and I figured it would be a waste if I didn't try it, so I took 2 freediving classes here from an instructor I met by chance over dinner and beers. I discovered freediving is completely unlike any other sport I've done. Its closest counterpart is meditation. The key is holding your breath by slowing down your heart rate. Before you dive, you calm yourself for a few minutes and clear you mind (matrix reference) to the point you feel sleepy. With some training, ...
Egypt part 6: dahab
... famous for being a backpacker's mecca decades ago. It's sharm el shiekh's less commercial, more chilled out, more pleasant, albeit likely stoned brother. No one's tried to sell me anything so far and the people have been genuinely pleasant. I initially planned to stay just 2 nights here, but extended my stay to 5 nights after realizing how cheap and pleasant the place is. I don't know where else in the world you can pay us$4 for a beachfront hut. ...
Special Addition: Ode to the Beard
... border: 0px; font-family: inherit; font-size: 15.555556297302246px; font-style: inherit; margin: 0px; outline: 0px; padding: 0px; vertical-align: baseline;">Honey is impossible to eat because ...
Mosquito in the room!
... them. The woman had a huge expensive camera in an even bigger and more expensive waterproof case. It was like an Asian but underwater. She took photos of everything, her fins nearly knocking off pieces of coral time and time again. It was quite sad really. Me and will got back to dahab and went for dinner at meya meya again, and he agreed we should make it a regular haunt! Now watching a film then a much needed sleep. Less than 7 weeks till I'm back and less than 1 until Sam is ...
Wilderness Wanderings
... and it wasn't too long before we were beside it. Before the all important float in the salty sea we stopped off at En Gedi, David's place of refuge. It's a lovely oasis in the middle of dry and dusty desert. We could imagine David and his men hiding out here and wondered if they enjoyed splashing in the waterfalls! It was INCREDIBLY hot here, as it has been over the last few days in Israel. We walked to the first waterfall and Sim and the kids had fun cooling ...


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Book your room at Blandford Hotel
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3-star London bed & breakfast in Marylebone, walk to Madame Tussaud's Wax Museum
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- Fee for wireless Internet in public areas: GBP 7.5 (for 24 hours, rates may vary)
We should mention
Children 1 years old and younger stay free when occupying the parent or guardian's room, using existing bedding.


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29 of 92 Items
Atlas 134. Vol. 2, 1915.
Cities & towns -- New York (State) -- Maps
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Image ID: 1954639
Queens V. 2, Plate No. 26 [Map bounded by 13th Ave., Graham Ave., 8th Ave., Broadway]
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Native Plants
Q. Who is Mr. Smarty Plants?
A: There are those who suspect Wildflower Center volunteers are the culpable and capable culprits. Yet, others think staff members play some, albeit small, role. You can torture us with your plant questions, but we will never reveal the Green Guru's secret identity.
Did you know you can access the Native Plant Information Network with your web-enabled smartphone?
Ask Mr. Smarty Plants is a free service provided by the staff and volunteers at the Lady Bird Johnson Wildflower Center.
Need help with plant identification, visit the plant identification page.
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Tuesday - May 21, 2013
From: Waterford, CA
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Topic: Poisonous Plants
Title: Beneficial characteristics of Phytolacca americana (Pokeweed)
Answered by: Nan Hampton
QUESTION:I have a surprise Polk weed plant growing in my back yard, does it have any beneficial uses,and if not, how best to eradicate it. Thank you.
Phytolacca americana (American pokeweed) is a very interesting plant and about this time each year we get inquiries from people about this large plant with white flowers and/or purple berries growing on their property. Native Americans used various parts of the plant to treat numerous ailments. Although the plants are considered poisonous, their various parts (leaves, shoots, berries) are also edible if collected and prepared properly. Here is more information from Ohio State University Extension.
There are several plants growing in my yard here in Texas. I like them! The birds love the berries; but, given the toxic nature of the plant—especially if you have children that come into your yard and would be attracted to the red berries—you might want to remove your plant. They aren't an endangered species. You want to do this before the plant is well-established. Since you have only one plant, it shouldn't be too difficult to achieve. If possible, dig up the entire plant with as much of the root as possible. If you can't get the entire root out of the ground, you could paint the cut surface of the root with an herbicide (such as RoundUp) using a small foam brush. You will want to paint the cut surface quickly after you cut down the plant because most plant cells can quickly seal themselves (a defense mechanism) and, thus, won't absorb as much herbicide. Seal the plant in a plastic bag and dispose of it in the garbage. Read and follow the health safety directions on the herbicide container and be careful not to get the herbicide on any plant you're interested in keeping. More plants may show up. Birds eat and deposit seeds.
Here's an interesting article: Pokeweed, American (Phytolacca americana): The Jekyll and Hyde Plant.
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My 'Kitchen Shelf and Roses' Roseart
ron_and_susan(z8 GA)December 1, 2011
This Roseart makes #310 I have done so far. I added the roses on the two cups in this work for effect. The roses I used are Cocktail, Sweet Vivienne, Surrey, Charisma, Judy Fisher, Margo Koster, Pink Miediland, Raubritter, Jane Bullock, Nearly Wild, Clytemnestta, Eddies Crimson, Moody Dream(Top Cup), Butterflies(Hanging Cup), Gardenia and last Moody Blues(Bud). --Enjoy--Ron


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- Bletonism
letterpressed print
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Bletonism: the supposed faculty of perceiving subterraneous springs and currents by sensation


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8241 131st Street West
Apple Valley, Minnesota, 55124
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8241 131st Street West has a Walk Score of 1 out of 100. This location is a Car-Dependent neighborhood so almost all errands require a car.
This location is in Apple Valley. Nearby parks include Terrace Oaks Park and Chateaulin Park.
Nearby schools include Greenleaf Elementary School and Apple Valley Senior High School.
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Wearing a headset, S. Priyadarshini a Class XII student, strains her ears to recognise the word she hears, and asks for its meaning. "An official policy of racial segregation formerly practised in the Republic of South Africa," says the tutor, and Priyadarshini responds 'a-p-a-r-t-h-e-i-d' immediately.
"I initially thought I heard 'a party' and not apartheid. Sometimes the British accent is difficult to decipher," says Priyadarshini who was among the participants at the State-level finals of the MaRRS International Spelling Bee 2010-11. Students from Class I to XII were divided into six categories for the competition.
Every student had a different technique to remember spellings, but what connects them all is their love for words. Class II student Sneha Hariharan has a personal-dictionary in which she jots down any new word she comes across. "Yesterday I heard my grandfather mention 'famine' to someone that I have it written down," she says. And Mithali Chordia from Chettinad Vidyashram, who came second in the International level last year, uses a mobile-application which keeps her updated with "weird new words".
Students went through rounds of oral and written tests. The oral rounds were held in the State-level and the preliminary written tests for short-listing students for the national-levels were also conducted.
In 'spell-it' one of the oral rounds, students were tested on spellings following which they were presented with words in the phonetic form. They had to identify, give the meaning and spell of the words.
The written round had questions on jumbled letters, word application and picture crosswords.
"We give students and their parents an orientation to the various techniques to remember spellings. Using flash cards, visual thinking methods and mnemonics are interesting ways to remember words. These can be applied not just to learn spellings but other subjects too," says D. Manivannan, Proprietor, Septcon Ventures that organised the event on behalf of MaRRS Intellectual Services.
Keywords: MaRRS International Spelling Bee, Spelling Bee