AU619523B2 - Process for the diacylation of compounds containing two aromatic rings - Google Patents

Process for the diacylation of compounds containing two aromatic rings Download PDF

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Publication number
AU619523B2
AU619523B2 AU30066/89A AU3006689A AU619523B2 AU 619523 B2 AU619523 B2 AU 619523B2 AU 30066/89 A AU30066/89 A AU 30066/89A AU 3006689 A AU3006689 A AU 3006689A AU 619523 B2 AU619523 B2 AU 619523B2
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AU
Australia
Prior art keywords
general formula
compound
process according
moles
acylating agent
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Ceased
Application number
AU30066/89A
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AU3006689A (en
Inventor
Michel Devic
Jacques Kervennal
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Arkema France SA
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Atochem SA
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/29—Saturated compounds containing keto groups bound to rings
    • C07C49/35—Saturated compounds containing keto groups bound to rings containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/782—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/12—Polycyclic non-condensed hydrocarbons
    • C07C15/14—Polycyclic non-condensed hydrocarbons all phenyl groups being directly linked
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/12—Polycyclic non-condensed hydrocarbons
    • C07C15/16—Polycyclic non-condensed hydrocarbons containing at least two phenyl groups linked by one single acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
    • C07C321/12—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to acyclic carbon atoms
    • C07C321/20—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/46—Friedel-Crafts reactions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Television Signal Processing For Recording (AREA)
  • Networks Using Active Elements (AREA)
  • Electrotherapy Devices (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

Abstract

Diacylation of compounds of general formula <IMAGE> with X : O, S, <IMAGE> or -CH2- R1, R2, R3 and R4, which are identical or different: H or an alkyl radical containing from 1 to 4 carbon atoms, by bringing the compound (I) into contact with HF, BF3 and at least 2 moles of an acylating agent per mole of (I) at a temperature of between -40 DEG C and 0 DEG C.

Description

619523 COMMONWEALTH OF AUSTRALIA PATENTS ACT 1952 COMPLETE SPECIFICATION NAME ADDRESS OF APPLICANT: Atochem La Defense 4 8 Cours Michelet Puteaux 92800 France NAME(S) OF INVENTOR(S): Michel DEVIC Jacques KERVENNAL ADDRESS FOR SERVICE: C t DAVIES COLLISON Patent Attorneys 1 Little Collins Street, Melbourne, 3000.
COMPLETE SPECIFICATION FOR THE INVENTION ENTITLED: Process for the diacylation of compounds containing two aromatic rings The following statement is a full description of this invention, including the best method of performing it known to me/us:ir' A ii i 2 The present invention relates to a process for the diacylation of compounds having two aromatic rings in their molecule, of general formula: wherein X denotes an oxygen or sulphur atom, or a or -CH 2 group,
R
1
R
2 R3, R 4 are identical or different and represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
Diacylation is to be understood to mean the conversion of a compound of general formula to a compound of general formula:
C-R
O (II) wherein X, R1' R2, R 3
R
4 have the same definition as in i I, i i Sf r 3 R is as defined for R 1
R
2
R
3
R
4 by means of an acylating agent of general formula: R -C Y (III) o wherein Y is a halogen atom, an -OH or -OR group or ctr rO
C
CI-
I R R being as defined above.
Examples of acylating agents thus defined are given, for example, in EP-A-069597.
The compounds of formula (II) are used in industry as intermediates, for example to produce polyester-type polymers. This is particularly so in the case of those in which R is in positions 4 and such as 4,4'-diacetyldiphenyl ether: CH 0 0-0 C-CH 0 0 The acylation of diphenyl ether to form, for example, 4 -phenoxyacetone: S4 CH3-C 0
O
as described for example in the abovementioned European Patent Application, is known.
This same Application teaches that acylation in the presence of hydrofluoric acid HF practically excludes Et diacylation, which however does occur in the presence of aluminium chloride A1C1.
tin" The drawbacks attending the latter's use are known to limit its industrial interest to a large extent.
The present invention enables such a choice to be avoided and can lead to highly pure products of formula in a very high chemical yield, or yield in terms of the diacylation of the compound of general formula SThe present invention provides a process for the diacylation of compounds of general formula to compounds of general formula by bringing a compound of general formula into contact with an acylating agent of general formula (III) in anhydrous medium, characterized in that this bringing into contact is effected at a temperature 0 0 between -40 C and 0°C in the presence of hydrofluoric acid HF, boron fluoride BF 3 and at least 2 moles of acylating agent of general formula (III) per mole of compound of general formula The aim of the invention, diacylation of a compound
Y
I I 5 of general formula is most generally achieved when 1 to moles of HF and 5 to 20 moles of BF 3 are present per mole of the said compound.
The BF3/HF molar ratio which is often most preferable is from 10/1 to 0.5/1.
The molar ratio of acylating agent to compound of formula is usually limited to a value not exceeding 5/1.
The most commonly used acylating agents are acid Schlorides and acid anhydrides, in particular acetyl chloride 10 and acetic anhydride.
The presence of a.solvent in the acylation medium may be useful, in particular for facilitating solubilization of the compound of general formula and contact between the components of this medium.
J 15 The solvent may be one of those that are known to be suitable for Friedel-Crafts reactions such as dichloromethane, nitromethane or carbon disulphide.
The process of the invention can be carried out in S any equipment that will resist pressure, and HF, BF 3 under the conditions defined above, such as a stainless steel autoclave.
The operation according to the invention is usually fast. Its duration is, for example, of the order of 1 hour, and even less.
The following Examples further illustrate the invention.
6 In all these Examples, the compound of general formula the acylating agent, HF, BF 3 and, where present, the methylene chloride used as solvent, are brought into contact in a stirred stainless steel autoclave for 1 hour, purity is understood to mean the purity, expressed as by weight, of the compound of general formula (II) obtained by addition of water and sodium hydroxide once autoclaving is over, followed by filtration and washing with 1, 0 water, and drying under vacuum at 80 C, S. chemical yield is understood to mean the number of moles, expressed as of compound of general formula (I) converted to compound of general formula (II), the analytical methods are liquid phase chromatography and nuclear magnetic resonance (NMR).
Example 1: Diphenyl ether: is brought into contact at -40 0 C with (per mole of diphenyl ether) 2.2 moles of acetic anhydride, 10 moles of HF and moles of BF 3 The purity of the 4,4'-diacetyldiphenyl ether obtained and the chemical yield are above 98 i 7 Example 2: Diphenyl sulphide:
SQ
is brought into contact at 0 C with (per mole of diphenyl sulphide) 3 moles of acetyl chloride, 10 moles of HF, moles of BF 3 and 200 g of methylene chloride.
0o0 The purity of the resulting 4,4'-diacetyldiphenyl o.O sulphide obtained is equal to 96 and the chemical yield is So"Q' equal to 90 00 10 Example 3: p-Diphenylbenzene: coeo .e is brought into contact at 0°C with (per mole of p-diphenyl- 92 20 Example 4: CH 2 benzene) 3 moles of acetyl chloride, 20 moles of HF, moles of BF 3 and 400 g of methylene chloride.
The purity of the 4,4'-diacetyldiphenylbenzene obtained is above 98 and the chemical yield is equal to 92 Example 4: Diphenylmethane: OCH2 o 0 8 is brought into contact at -20 0 C with (per mole of diphenylmethane) 2.2 moles of acetic anhydride, 2.5 moles of HF, moles of BF 3 and 200 g of methylene chloride.
The purity of the 4,4'-diacetyldiphenylmethane obtained is equal to 90% and the chemical yield is equal to Example m-Benzyltoluene: #tti C H 3
CH
2
Q
*e is brought into contact at 0° C with (per mole of m-benzyltoluene) 3 moles of acetyl chloride, 2.5 moles of HF and moles of BF 3 J The chemical yield is 80 and the product obtained has a purity of 90 with respect to diacetyl compounds, in particular those acylated at positions 4 and 4'.
*Se e.

Claims (8)

1. Process for the diacylation of a compound of general formula: RI R 3 O x Q(I) R R wherein X denotes an oxygen or sulphur atom, or a or -CH 2 group, I R 1 R2' R, R 4 are identical or different and represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, to a compound of general formula: R R 3 C-R O x (II) R-C O R 2 R 4 wherein X, RI, R 2 R 3 R 4 are defined above and R is as defined for RI, R 2 R 3 R 4 by means of an acylating agent of general formula: R C Y(III) 0 (III) 10 wherein Y is a halogen atom, an -OH or -OR group or 0 V -0-C C R R being as defined above which comprises bringing the compound of general formula into contact with at least 2 moles, per mole of compound of general formula of the acylating agent of general formula (III) in an anhydrous medium at a temperature from -40 0 C to 0°C in the presence of hydrofluoric acid HF and boron trifluoride BF 3
2. Process according to Claim 1, in which 1 to moles of HF and 5 to 20 moles of BF 3 are present per mole v of compound of general formula
3. Process according Claim 1 or 2, in which the BF 3 /HF molar ratio is from 10/1 to 0.5/1.
4. Process according to any one of Claims 1 to 3, in which the molar ratio of acylating agent to compound of formula does not exceed 5/1. Process according to any one of Claims 1 to 4, in which the acylating agent is acetyl chloride.
6. Process according to any one of Claims 1 to 4, in which the acylating agent is acetic anhydride.
7. Process according to any one of Claims 1 to 11 6, in which the anhydrous medium includes a solvent.
8. Process according to Claim 7, in which the solvent is methylene chloride.
9. Process according to Claim 1 substantially as described in any one of the Examples. A compound of general formula (II) as defined in Claim 1 whenever obtained by a process as claimed in any one of the preceding Claims. 4.)r +t 4 1 4 4r 4t) 12 I I Ina~ ~r~mr~~i r~r~ Ldisclosed herein or referred to or i e in the specification and/or c of this application, individuall o lectively, and any and all combinations +f -n n rtpp AV r ±nnfp- 4- K J ,tt~ I I. I t t~ ~I C I I It 41 1 II *4 I IL I I I LI I I I j I DATED this SEVENTEENTH day of FEBRUARY 1989 Atochem by DAVIES COLLISON Patent Attorneys for the applicant(s) ro L
AU30066/89A 1988-02-18 1989-02-17 Process for the diacylation of compounds containing two aromatic rings Ceased AU619523B2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR8802192A FR2627486B1 (en) 1988-02-18 1988-02-18 PROCESS FOR THE DIACYLATION OF COMPOUNDS COMPRISING TWO AROMATIC CORES
FR8802192 1988-02-18

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AU3006689A AU3006689A (en) 1989-08-24
AU619523B2 true AU619523B2 (en) 1992-01-30

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EP (1) EP0340117B1 (en)
JP (1) JPH023619A (en)
KR (1) KR950008286B1 (en)
CN (1) CN1020718C (en)
AT (1) ATE78019T1 (en)
AU (1) AU619523B2 (en)
DE (1) DE68902005T2 (en)
DK (1) DK73389A (en)
ES (1) ES2043072T3 (en)
FI (1) FI890798A (en)
FR (1) FR2627486B1 (en)
GR (1) GR3005886T3 (en)
IE (1) IE890498L (en)
IL (1) IL89128A0 (en)
NO (1) NO169066C (en)
PT (1) PT89752B (en)
ZA (1) ZA891212B (en)

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DE3927772A1 (en) * 1989-08-23 1991-02-28 Bayer Ag METHOD FOR PRODUCING AROMATIC DICARBONIC ACIDS AND NEW AROMATIC DICARBONIC ACIDS
US7314888B1 (en) * 1998-11-05 2008-01-01 Toyama Chemical Co., Ltd. Compounds and medicinal use thereof
DK1140761T3 (en) 1999-01-12 2004-01-26 Clariant Finance Bvi Ltd Benzophenones and their use as photoinitiators
EP1211235A3 (en) * 2000-11-30 2004-01-02 JFE Chemical Corporation Preparation process of 4,4'-Dicarboxydiphenyl ethers or derivatives thereof
CN1297530C (en) * 2004-05-17 2007-01-31 河南大学 Process for preparing n-hexylic acid by oxidation of sec- octyl alcohol with nitric acid and its special device
CN1332923C (en) * 2005-11-16 2007-08-22 陕西师范大学 2-(9-anthryl)-2-carbonylethyl acetate solid phase synthesis method

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0199661A1 (en) * 1985-04-16 1986-10-29 Rhone-Poulenc Chimie Process for the preparation of acylbiphenyl derivatives

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JPS5929178B2 (en) * 1978-04-08 1984-07-18 丸善石油化学株式会社 Process for producing 2-alkyl-6-acylnaphthalene
BE893790A (en) * 1981-07-08 1983-01-07 Raychem Corp PREPARATION OF AROMATIC KETONES
FR2519974A1 (en) * 1982-01-21 1983-07-22 Rhone Poulenc Spec Chim PROCESS FOR THE ACYLATION OF HALOGENO OR TRIHALOGENOMETHYLBENZENES
ES8700647A1 (en) * 1984-10-11 1986-11-16 Raychem Corp Preparation of aromatic carbonyl compounds.
EP0189266A3 (en) * 1985-01-18 1986-10-08 The Dow Chemical Company Purification of haloacetyl derivatives of aromatic hydrocarbons
FR2577220B1 (en) * 1985-02-08 1987-05-29 Rhone Poulenc Spec Chim PROCESS FOR ACETOACETYLATION OF AROMATIC COMPOUNDS

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0199661A1 (en) * 1985-04-16 1986-10-29 Rhone-Poulenc Chimie Process for the preparation of acylbiphenyl derivatives

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Publication number Publication date
EP0340117A1 (en) 1989-11-02
KR950008286B1 (en) 1995-07-27
FI890798A (en) 1989-08-19
NO169066C (en) 1992-05-06
IL89128A0 (en) 1989-08-15
DK73389A (en) 1989-08-19
NO890658D0 (en) 1989-02-16
CN1020718C (en) 1993-05-19
ATE78019T1 (en) 1992-07-15
PT89752A (en) 1989-10-04
EP0340117B1 (en) 1992-07-08
FR2627486B1 (en) 1991-03-22
FI890798A0 (en) 1989-02-17
ZA891212B (en) 1989-11-29
DK73389D0 (en) 1989-02-17
IE890498L (en) 1989-08-18
PT89752B (en) 1994-03-31
NO169066B (en) 1992-01-27
CN1035105A (en) 1989-08-30
ES2043072T3 (en) 1993-12-16
AU3006689A (en) 1989-08-24
FR2627486A1 (en) 1989-08-25
JPH023619A (en) 1990-01-09
DE68902005T2 (en) 1993-01-14
NO890658L (en) 1989-08-21
DE68902005D1 (en) 1992-08-13
KR890012929A (en) 1989-09-20
GR3005886T3 (en) 1993-06-07

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