Patent number: 8772519
Abstract: The invention relates to a process for preparing mono-allyl-functionalized dialkylphosphinic acids, esters and salts with allylic compounds, characterized in that a) a phosphinic acid source (I) is reacted with olefins (IV) in the presence of a catalyst A to give an alkylphosphonous acid, or salt or ester thereof (II), b) the alkylphosphonous acid, or salt or ester thereof (II) thus formed is reacted with allylic compounds of the formula (V) in the presence of a catalyst B and of a base to give a mono-allyl-functionalized dialkylphosphinic acid derivative (III), where R1, R2, R3, R4, R5, R6, R7, R8, R9 are the same or different and are each independently, inter alia, H, C1-C18-alkyl, C6-C18-aryl, C6-C18-aralkyl, C6-C18-alkylaryl, and X is H, C1-C18-alkyl, C6-C18-aryl, C6-C18-aralkyl, C6-C18-alkylaryl, Mg, Ca, Al, Sb, Sn, Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Cu, Ni, Li, Na, K and/or a protonated nitrogen base, and the catalysts A and B are transition metals and/or transition metal compounds and/or catalyst syst
Type:
Grant
Filed:
October 6, 2009
Date of Patent:
July 8, 2014
Assignee:
Clariant Finance (BVI) Limited
Inventors:
Michael Hill, Werner Krause, Martin Sicken
Patent number: 8614267
Abstract: The invention relates to a method for producing mono-hydroxyfunctionalized dialkylphosphinic acids and esters and salts thereof by means of allyl alcohols, characterized in that a) a phosphinic acid source (I) is reacted with olefins (IV) to yield an alkylphosphonic acid, salt or ester (II) thereof in the presence of a catalyst A, b) the thus obtained alkylphosphonic acid, salt or ester (II) thereof is reacted with compounds of formula (V) to yield a mono-hydroxyfunctionalized dialkylphosphinic acid derivative (III) in the presence of a catalyst B, wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, are the same or different and stand independently of each other, among other things, for H, C1-C18 alkyl, C6-C18 aryl, C6-C18 aralkyl, C6-C18 alkylaryl, and X stands for H, C1-C18 alkyl, C6-C18 aryl, C6-C18 aralkyl, C6-C18 alkylaryl, Mg, Ca, Al, Sb, Sn, Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Cu, Ni, Li, Na, K and/or a protonized nitrogen base, and the catalyst A is formed by transition metals and/or transition metal compound
Type:
Grant
Filed:
October 6, 2009
Date of Patent:
December 24, 2013
Assignee:
Clariant Finance (BVI) Limited
Inventors:
Michael Hill, Werner Krause, Martin Sicken
Publication number: 20120330048
Abstract: The invention relates to a novel important lycopene intermediate 3,7, 11-trimethyl-1,3,6,10-tetraene-dodecyl diethyl phosphonate. A current lycopene intermediate 2,4,6,10-tetra-double bond pentadec-carbon phosphonate is difficult to synthesize. The invention provides a novel intermediate, which has the following synthesis steps of: preparing 2,6,10-trimethyl-3,5,9-undecane triene-1-aldehyde from pseudoionone; preparing 2,6,10-trimethyl-2,5,9-undecane triene-1-aldehyde from the 2,6,10-trimethyl-3, 5,9-undecane triene-1-aldehyde; and subjecting the 2,6,10-trimethyl-2,5,9-undecane triene-1-aldehyde and tetraethyl methylenediphosphonate to condensation reaction to obtain target product. The invention can generate novel intermediate from raw material pseudoionone only by four reactions, thus the reactions are easy to control and great industrial value are achieved.
Type:
Application
Filed:
March 9, 2011
Publication date:
December 27, 2012
Applicants:
UNIVERSITY OF SHAOXING, ZHEJIANG MEDICINE CO., LTD. XINCHANG PHARMACEUTICAL FACTORY
Inventors:
Xuejun Lao, Runpu Shen, Weidong Ye, Xiaohua Song, Luo Liu, Chunlei Wu, Yibin Wu, Liujiang Hu
Publication number: 20110224340
Abstract: The invention relates to a method for producing mono-vinylfunctionalized dialkylphosphinic acids, esters, and salts, characterized in that a) a phosphinic acid source (I) is converted with olefins (IV) to an alkylphosphonic acid, salt, or ester (II) in the presence of a catalyst A, b) the alkylphosphonic acid, salt, or ester (II) thus created is converted with acetylenic compounds of formula (V) into a mono-vinylfunctionalized dialkylphosphinic acid derivative (III) in the presence of a catalyst B, where R1, R2, R3, R4, R5, R6 are the same or different and are independent of each other, among other things, H, C1-C18 alkyl, C6-C18 aryl, C6-C18 aralkyl, C6-C18 alkylaryl, and X stands for H, C1-C18 alkyl, C6-C18 aryl, C6-C18 aralkyl, C6-C18 alkylaryl, Mg, Ca, Al, Sb, Sn, Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Cu, Ni, Li, Na, K and/or a protonized nitrogen base, and the catalysts A and B are transition metals and/or transition metal compounds and/or catalyst systems comprised of a transition metal and/or a transitio
Type:
Application
Filed:
October 6, 2009
Publication date:
September 15, 2011
Applicant:
CLARIANT FINANCE (BVI) LIMITED
Inventors:
Michael Hill, Werner Krause, Martin Sicken
Publication number: 20110213052
Abstract: The invention relates to a method for producing mono-carboxyfunctionalized dialkylphosphinic acids and esters and salts thereof, characterized in that a) a phosphinic acid source (I) is reacted with olefins (IV) to yield an alkylphosphonic acid, salt or ester (II) thereof in the presence of a catalyst A, b) the alkylphosphonic acid thus obtained, salt or ester (II) thereof is reacted with an ?,?-unsaturated carboxylic acid derivative (V) to yield a mono-carboxyfunctionalized dialkylphosphinic acid derivative (III) in the presence of a catalyst B, wherein R1, R2, R3, R4, R5, R6, R7 are the same or different and stand independently of each other, among other things, for H, C1-C18 alkyl, C6-C18 aryl, C6-C18 aralkyl, C6-C18 alkylaryl, and X and Y are the same or different and stand independently of each other for H, C1-C18 alkyl, C6-C18 aryl, C6-C18 aralkyl, C6-C18 alkylaryl, Mg, Ca, Al, Sb, Sn, Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Cu, Ni, Li, Na, K and/or a protonized nitrogen base, and the catalyst A is formed b
Type:
Application
Filed:
October 6, 2009
Publication date:
September 1, 2011
Applicant:
CLARIANT FINANCE (BVI) LIMITED
Inventors:
Michael Hill, Harald Bauer, Werner Krause, Martin Sicken
Publication number: 20110213080
Abstract: The invention relates to a process for preparing mono-allyl-functionalized dialkylphosphinic acids, esters and salts with allylic compounds, characterized in that a) a phosphinic acid source (I) is reacted with olefins (IV) in the presence of a catalyst A to give an alkylphosphonous acid, or salt or ester thereof (II), b) the alkylphosphonous acid, or salt or ester thereof (II) thus formed is reacted with allylic compounds of the formula (V) in the presence of a catalyst B and of a base to give a mono-allyl-functionalized dialkylphosphinic acid derivative (III), where R1, R2, R3, R4, R5, R6, R7, R8, R9 are the same or different and are each independently, inter alia, H, C1-C18-alkyl, C6-C18-aryl, C6-C18-aralkyl, C6-C18-alkylaryl, and X is H, C1-C18-alkyl, C6-C18-aryl, C6-C18-aralkyl, C6-C18-alkylaryl, Mg, Ca, Al, Sb, Sn, Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Cu, Ni, Li, Na, K and/or a protonated nitrogen base, and the catalysts A and B are transition metals and/or transition metal compounds and/or catalyst syst
Type:
Application
Filed:
October 6, 2009
Publication date:
September 1, 2011
Applicant:
CLARIANT FINANCE (BVI) LIMITED
Inventors:
Michael Hill, Werner Krause, Martin Sicken
Publication number: 20110201733
Abstract: The invention relates to a method for producing mono-hydroxyfunctionalized dialkylphosphinic acids and esters and salts thereof by means of allyl alcohols, characterized in that a) a phosphinic acid source (I) is reacted with olefins (IV) to yield an alkylphosphonic acid, salt or ester (II) thereof in the presence of a catalyst A, b) the thus obtained alkylphosphonic acid, salt or ester (II) thereof is reacted with compounds of formula (V) to yield a mono-hydroxyfunctionalized dialkylphosphinic acid derivative (III) in the presence of a catalyst B, wherein R1, R2, R3,R4, R5, R6, R7, R8, R9, are the same or different and stand independently of each other, among other things, for H, C1-C18 alkyl, C6-C18 aryl, C6-C18 aralkyl, C6-C18 alkylaryl, and X stands for H, C1-C18 alkyl, C6-C18 aryl, C6-C18 aralkyl, C6-C18 alkylaryl, Mg, Ca, Al, Sb, Sn, Ge, Ti, Fe, Zr, Zn, Ce, Bi, Sr, Mn, Cu, Ni, Li, Na, K and/or a protonized nitrogen base, and the catalyst A is formed by transition metals and/or transition metal compounds
Type:
Application
Filed:
October 6, 2009
Publication date:
August 18, 2011
Applicant:
CLARIANT FINANCE (BVI) LIMITED
Inventors:
Michael Hill, Werner Krause, Martin Sicken