Process for the preparation of acylphosphines, acyl oxides and acyl sulfides
원문보기
IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
C07F-009/02
C07F-009/00
출원번호
US-0847095
(2004-05-17)
우선권정보
CH-2376/98(1998-11-30); CH-2434/98(1998-12-08)
발명자
/ 주소
Leppard,David George
Eichenberger,Eugen
Kaeser,Ren챕쨈
Hug,Gebhard
Schwendimann,Urs
출원인 / 주소
Ciba Specialty Chemicals Corporation
인용정보
피인용 횟수 :
0인용 특허 :
14
초록▼
A description is given of processes for the preparation of mono-and bisacylphosphines and of mono-and bisacylphosphine oxides and mono-and bisacylphosphine sulfides, which comprises first reacting organic P-monohalogenophosphines or P,P-dihalogenophosphines, or mixtures thereof, with an alkali metal
A description is given of processes for the preparation of mono-and bisacylphosphines and of mono-and bisacylphosphine oxides and mono-and bisacylphosphine sulfides, which comprises first reacting organic P-monohalogenophosphines or P,P-dihalogenophosphines, or mixtures thereof, with an alkali metal or magnesium in combination with lithium, where appropriate in the presence of a catalyst, and then carrying out the reaction with acid halides and, in the case of the process for the preparation of oxides, carrying out an oxidation step and, in the case of the preparation of sulfides, reacting the phosphines so obtained with sulfur. It is characteristic, inter alia, that the processes are carried out without isolation of the intermediates.
대표청구항▼
What is claimed is: 1. A process for the preparation of acylphosphine oxides and acylphosphine sulfides of formula IV wherein n is 1 or 2; when n is 1, m is 1; when n is 2, m is 1 or 2; R1, when n=1, is C1-C18alkyl, C2-C18alkyl which is interrupted by one or several non-successive O atoms; pheny
What is claimed is: 1. A process for the preparation of acylphosphine oxides and acylphosphine sulfides of formula IV wherein n is 1 or 2; when n is 1, m is 1; when n is 2, m is 1 or 2; R1, when n=1, is C1-C18alkyl, C2-C18alkyl which is interrupted by one or several non-successive O atoms; phenyl-substituted C1-C4alkyl, C2-C8alkenyl, phenyl, naphthyl, biphenyl, C5-C12cycloalkyl or a 5-or 6-membered O-, S-or N-containing heterocyclic ring, the radicals phenyl, naphthyl, biphenyl, C5-C12cycloalkyl or the 5-or 6-membered O-, S-or N-containing heterocyclic ring being unsubstituted or substituted by one to five halogen, C1-C6alkyl, C 1-C8alkylthio and/or C1-C8alkoxy; R1, when n=2, is C1-C18alkylene, C2-C18 alkylene which is interrupted by one or several non-successive O atoms; or R1 is C1-C6alkylene which is substituted by C1-C4alkoxy, phenyl, C1-C 4alkylphenyl, phenyl-C1-C4alkyl or C1-C4alkoxyphenyl; or R1 is phenylene or xylylene, which radicals are unsubstituted or substituted by one to three C1-C4alkyl and/or C1-C4alkoxy, or R1 is a--CH2CH═CHCH2--, R2 is C1-C18alkyl, C3-C12cycloalkyl, C2-C18alkenyl, phenyl, naphthyl, biphenyl or a 5-or 6-membered O-, S-or N-containing heterocyclic ring, the radicals phenyl, naphthyl, biphenyl or 5-or 6-membered O-, S-or N-containing heterocyclic ring being unsubstituted or substituted by one to four C1-C8alkyl, C1-C8alkoxy, C 1-C8alkylthio and/or halogen; R3 is C1-C18alkyl, C2-C18alkyl which is interrupted by one or several non-successive O atoms; phenyl-substituted C1-C4alkyl, C2-C8alkenyl, phenyl, naphthyl, biphenyl, C5-C12 cycloalkyl or a 5-or 6-membered O-, S-or N-containing heterocyclic ring, the radicals phenyl, naphthyl, biphenyl, C5-C12 cycloalkyl or the 5-or 6-membered O-, S-or N-containing heterocyclic ring being unsubstituted or substituted by one to five halogen, C 1-C8alkyl, C1-C8alkylthio and/or C 1-C8alkoxy; Q is a single bond, CR6R7,--O--or--S--; R4 and R5 are each independently of the other hydrogen, C1-C4alkyl or C1-C4 alkoxy; R6 and R7 are each independently of the other hydrogen or C1-C4alkyl; and Z is O or S, by (1) reacting organic phosphorus halides of formula II wherein Y is Br or Cl and R1, R3, n and m have the meaning cited above, with an alkali metal or with magnesium in combination with lithium, or with mixtures thereof, optionally in the presence of a catalyst, and (2) subsequent reaction with m equivalents of acid halides of formula III wherein R2, m and Y have the meaning above, and (3) oxidation or reaction with sulfur of the acylphosphine of formula I which is obtained by reaction (2), wherein R1, R2, R3, m and n have the meaning cited above, which process is carried out without isolation of the intermediates. 2. A process according to claim 1, wherein R1, if n=1, is C1-C12alkyl, cyclohexyl, phenyl or biphenyl, the groups phenyl and biphenyl being unsubstituted or substituted by one to four C1-C8alkyl and/or C1-C8alkoxy; R1, if n=2, is C6-C10alkylene, or R3 is C1-C12alkyl, cyclohexyl, phenyl or biphenyl, the groups phenyl and biphenyl being unsubstituted or substituted by one to four C1-C8alkyl and/or C1-C8alkoxy; Q is a single bond or--O--, and R4 and R5 are hydrogen. 3. A process according to claim 1, wherein R2 is phenyl which is substituted in 2,6-or 2,4,6-position by C1-C4alkyl and/or C1-C4 alkoxy. 4. A process according to claim 1, wherein n is 1. 5. A process according to claim 1, wherein Y in formula II is chloro. 6. A process according to claim 1, wherein the reaction (1) is carried out using lithium, sodium or potassium. 7. A process according to claim 6, wherein from 4 to 6 atom equivalents of the alkali metal are used for the preparation of compounds of formula I, wherein m is 2. 8. A process according to claim 1, wherein Y in the compounds of formula III is chloro. 9. A process according to claim 1, which comprises carrying out the reaction (1) in the presence of a catalyst. 10. A process according to claim 1, which comprises carrying out the reaction (1) of the organic phosphorus halides (II) with an alkali metal in the temperature range from-20째 to +120째 C. 11. A process according to claim 1, which comprises carrying out the reaction (1) of the organic phosphorus halides (II) with magnesium in combination with an alkali metal in the temperature range from 80째 to 120째 C. 12. A process according to claim 1, wherein the reaction (2) of the metallized phosphine with the acid chloride (III) is carried out at-20째 to +80째 C. 13. A process according to claim 1, wherein the reaction steps (1) and (2) are carried out in the same solvent. 14. A process according to claim 1, wherein, in formula I, n is 1, m is 1, R1 is phenyl which is unsubstituted or substituted by C1-C4alkyl or C1-C8alkoxy, or R 1 is C1-C12alkyl; R2 is phenyl which is substituted by halogen, C1-C4alkoxy or C1-C 4alkyl; and R3 is unsubstituted or C1-C4 alkyl-substituted phenyl. 15. A process according to claim 6, wherein 2 to 3 atom equivalents of the alkali metal are used for the preparation of compounds of formula I wherein m is 1.
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이 특허에 인용된 특허 (14)
Lechtken Peter (Frankenthal DEX) Buethe Ingolf (Ludwigshafen DEX) Jacobi Manfred (Frankenthal DEX) Trimborn Werner (Limburgerhof DEX), Acylphosphine oxide compounds their preparation and use.
Leppard, David George; Eichenberger, Eugen; Kaeser, Ren?; Hug, Gebhard; Schwendimann, Urs, Process for the preparation of acylphosphines, acyl oxides and acyl sulfides.
Husler Rinaldo (Wunnewil CHX) Orban Ivan (Basel CHX) Holer Martin (Magden CHX), Process for the preparation of alkylated aromatic carboxylic acids and acyl halides.
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