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WO1996014299A1 - Procede de production des acyle lactames - Google Patents

Procede de production des acyle lactames Download PDF

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Publication number
WO1996014299A1
WO1996014299A1 PCT/US1995/013818 US9513818W WO9614299A1 WO 1996014299 A1 WO1996014299 A1 WO 1996014299A1 US 9513818 W US9513818 W US 9513818W WO 9614299 A1 WO9614299 A1 WO 9614299A1
Authority
WO
WIPO (PCT)
Prior art keywords
process according
acyl
lactam
inorganic base
halide
Prior art date
Application number
PCT/US1995/013818
Other languages
English (en)
Inventor
Nour-Eddine Guedira
Gunter Gerd Ulrich Bellmann
Original Assignee
The Procter & Gamble Company
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by The Procter & Gamble Company filed Critical The Procter & Gamble Company
Priority to EP95937637A priority Critical patent/EP0789689A4/fr
Priority to BR9509585A priority patent/BR9509585A/pt
Priority to MX9703305A priority patent/MX9703305A/es
Priority to CA 2204014 priority patent/CA2204014A1/fr
Publication of WO1996014299A1 publication Critical patent/WO1996014299A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/39—Organic or inorganic per-compounds
    • C11D3/3902—Organic or inorganic per-compounds combined with specific additives
    • C11D3/3905—Bleach activators or bleach catalysts
    • C11D3/3907—Organic compounds
    • C11D3/3917—Nitrogen-containing compounds
    • C11D3/392—Heterocyclic compounds, e.g. cyclic imides or lactames
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
    • C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D223/08—Oxygen atoms
    • C07D223/10—Oxygen atoms attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/26—Organic compounds containing nitrogen
    • C11D3/28—Heterocyclic compounds containing nitrogen in the ring
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
    • D06L4/00—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
    • D06L4/10—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs using agents which develop oxygen
    • D06L4/12—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs using agents which develop oxygen combined with specific additives

Definitions

  • the present invention relates to a process for the production of acyl lactams. Such products are useful as bleach activators in detergent compositions.
  • the present invention relates to a process for making an acyl lactam and comprises reacting an acyl halide with a lactam in a substantially non-aqueous, substantially solvent-free, mixture containing an inorganic base.
  • the acyl lactam is made by heating a reaction mixture consisting essentially of the acyl halide, the lactam and the inorganic base.
  • the reaction mixture is substantially non-aqueous and substantially free of organic solvent and generally contains no significant volumes of other materials that would need to be separated from the end products.
  • the reaction mixture consists solely of the acyl halide, the lactam and the inorganic base or it consists of this mixture together with a minor amount of a quaternary ammonium compound.
  • the acyl halide is usually an acyl chloride, but any other suitable halide that will react satisfactorily in the reaction could be used.
  • the acyl group generally has the formula RCO- where R is generally an aryl group or a C ⁇ -20 linear or branched, saturated or unsaturated, fatty aliphatic group.
  • R is generally an aryl group or a C ⁇ -20 linear or branched, saturated or unsaturated, fatty aliphatic group.
  • the aryl group is preferably phenyl while the aliphatic group is preferably selected from C7-12 alkyl or alkenyl groups. Any of these groups may be optionally substituted with non-interfering substituents.
  • the preferred acyl halide is benzoyl chloride.
  • the lactam usually is a compound of the formula
  • the lactam can be substituted by one or more non-interfering substituents.
  • the inorganic base can be any inorganic base that will act as an acid halide acceptor in the process. It is generally a compound of a metal of groups 1 or 2 of the periodic table. In particular it is preferably a compound of an alkali metal or a metal of groups 2a or 2b of the periodic table. Preferred metals are potassium, magnesium, calcium and zinc. The compound is preferably capable of being introduced as a finely divided paniculate solid. Preferred compounds are oxides and carbonates, for instance potassium carbonate, magnesium oxide or carbonate, calcium oxide or carbonate or zinc oxide or carbonate. Zinc oxide is particularly preferred.
  • the amount of caprolactam or other lactam in the mixture is usually at least about 1 mole but not more than about 4 moles per mole of benzoyl chloride or other acyl halide. Generally it is at least about 1.3 moles and preferably at least about 1.7 moles. Generally the amount is not more than about 3 moles and preferably it is not more than about 2.3 moles. An amount of about 2 moles caprolactam per mole benzoyl chloride is generally preferred.
  • the amounts of inorganic base usually at least about 80% but usually not more than about 150% of the stoichiometric amount required for neutralising all the hydrogen halide formed by reaction from the acyl halide. Generally the amount is at least 100% of the stoichiometric amount. Generally it is not more than about 110 or 120% of the stoichiometric amount.
  • the base can neutralise two equivalents of the hydrogen halide. Accordingly the molar proportion of the base is usually at least about 0.5 moles, often 0.55 moles inorganic base per mole acyl halide. This applies to, for instance, inorganic bases such as ZnO, MgO, CaO, K2CO3 and CaCO ⁇ .
  • the amount of the inorganic base is preferably at least about 1.0, often about 1.1, moles per mole acyl halide. This applies to bases such an NaHC03, NaH and KOH.
  • a tertiary or quaternary ammonium compound is, per mole acid halide, generally below 0.1 moles, for instance in the range about 0.003 to about 0.05 moles, typically about 0.01 moles.
  • the purpose of including the tertiary or quaternary ammonium compound is to activate the acyl halide.
  • the ammonium compound appears to act as a catalyst.
  • Suitable compounds that can be incorporated for this purpose include tetra alkyl ammonium halides wherein the alkyl group can contain from 1 to 12 carbon atoms.
  • a suitable compound is tetra ethyl ammonium bromide.
  • ammonium compounds that can be used include pyridine, triethylamine, and N,N-dimethylaniline and other tertiary amines that may form a quaternary ammonium or acid addition salt in the reaction mixture.
  • Other components that can be included in the reaction mixture include water absorbing material in amounts of not more than necessary to react with traces of water introduced initially into the reaction mixture or formed during the neutralisation of the acid formed during the reaction.
  • reaction mixture may include other components that do not interfere undesirably with the process or with the recovery of the reaction products, it is generally preferred that the reaction mixture should contain only the materials named above, namely the acyl halide, the lactam, the inorganic base, the optionally catalytical and ammonium compound and the optional water absorbent compound.
  • the reaction is best conducted at a temperature of at least about 75° C and more usually at least about 85°C.
  • the reaction temperature can be as high as, for instance, 130°C but preferably it is not more than about 110°C for most or all of the reaction. Best results are generally obtained when the reaction temperature is in the range about 85 to 100°C, most preferably around 90 to 95°C.
  • the reaction mixture can be formed by forming a mixture of paniculate inorganic base with a melt or other fluid mixture of heated acyl halide and lactam.
  • lactam is introduced into the reaction vessel first and is heated to a temperature at which it is fluid or molten.
  • the acyl halide and the paniculate inorganic compound can then be added in either order but it is usually preferred to add the inorganic compound before the acyl halide.
  • the inorganic compound can be introduced into the reaction vessel before the lactam or can be present during the melting of the lactam.
  • the reaction is usually conducted for at least about one hour and it can be for as long as about 3 or 4 hours, but often the reaction time is around 1.5 to 2 hours.
  • the reaction vessel is preferably stirred throughout the reaction and may be fitted with a condenser open to the atmosphere.
  • the mixture may be cooled to near ambient temperature and the desired acyl lactam recovered by conventional techniques.
  • the recovery is performed by a method comprising the addition of an aqueous base, generally aqueous sodium bicarbonate.
  • an aqueous base generally aqueous sodium bicarbonate. This may be conducted by first diluting the mixture with a large excess of distilled water (for instance 3 to 10 parts by weight water per part by weight mixture) and sufficient sodium bicarbonate to make the mixture slightly alkaline, for instance about pH 8.
  • the resultant precipitate contains the desired end product and zinc hydroxide or other insoluble material derived from the inorganic compound.
  • Separation of the reaction product from the zinc hydroxide or other inorganic compound can be conducted by solvent extraction (for instance using acetone or methylene chloride) or by treatment with a mineral acid such as HC1 in order to solubilise the inorganic compound as, for instance, zinc chloride.
  • the recovery may be performed by treating the initial reaction product with aqueous hydrogen chloride or other mineral acid in order to solubilise inorganic compound present in the reaction mixture (for instance zinc oxide and zinc chloride).
  • aqueous hydrogen chloride or other mineral acid in order to solubilise inorganic compound present in the reaction mixture (for instance zinc oxide and zinc chloride).
  • the aqueous acid phase will then be separated from the water insoluble organic phase or water insoluble precipitate.
  • the water insoluble phase or precipitate will be rendered alkaline by the addition of base (for instance, aqueous sodium hydroxide) in order to precipitate the desired reaction product.
  • Example 1 The following are examples of the invention. Example 1
  • caprolactam 226g (2 moles) caprolactam is melted at 90 to 100°C in a 1.5 litre reaction vessel.
  • 45g zinc oxide (0.55 moles) and 2.1g tetra ethyl ammonium bromide (0.01 moles) in paniculate form are mixed into the melt to form a low to medium viscous dispersion.
  • 141g benzoyl chloride (1 mole) is added to the mixture over a period of about half an hour while maintaining the temperature in the range 90 to 103°C.
  • the reaction mixture is then held at 90°C for 1.5 hours to allow the reaction to proceed.
  • Example 3 The process of Example 1 is repeated but without the tetra ethyl ammonium bromide and with the addition of benzoyl chloride being conducted over a period of 0.75 hours and the reaction being continued for 2.75 hours. A yield of 62.1 % is obtained of a benzoyl caprolactam product having a melting point 53.1 to 59.7°C.
  • Example 3
  • Example 4 The process of Example 1 is repeated but without the tetra ethyl ammonium bromide and the zinc oxide is replaced by 76g (0.55 moles) anhydrous potassium carbonate. The addition of the benzoyl chloride is conducted over one hour at 90 to 140°C and then the reaction is performed for 2 hours at 90 to 130°C. Although the yield is only 33.2% , the obtained product is extremely pure benzoyl caprolactam and has melting point 69 to 69.9°C.
  • Example 4 Example 4
  • Example 5 The process of Example 1 is repeated using 0.5 moles magnesium oxide in place of the zinc oxide and tetra ethyl ammonium bromide. The addition of the benzoyl chloride is conducted over quarter of an hour at 80 °C and the reaction is conducted for 3 hours at 95 °C. A yield is obtained of about 38.6% of a product containing about 96.5% benzoyl caprolactam and having a melting point of 58.6 to 62.9°C.
  • Example 5 Example 5
  • Example 1 is repeated except that 0.6 moles calcium oxide is used in place of the zinc oxide and tetra ethyl ammonium bromide.
  • the benzoyl halide is added over a period of 0.5 hours at 90°C and the reaction is conducted at 90°C for 2 hours.
  • a yield is obtained of 60%, based on benzoyl chloride, of a product having a melting point of 44.6 to 52.8°C and which contains 93.6% benzoyl caprolactam.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Textile Engineering (AREA)
  • Inorganic Chemistry (AREA)
  • Hydrogenated Pyridines (AREA)
  • Cephalosporin Compounds (AREA)

Abstract

On prépare un acyle lactame en faisant réagir un halogénure d'acyle avec un lactame dans un mélange réactionnel sensiblement non aqueux, sensiblement exempt de solvant et contenant une base minérale.
PCT/US1995/013818 1994-11-03 1995-10-26 Procede de production des acyle lactames WO1996014299A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP95937637A EP0789689A4 (fr) 1994-11-03 1995-10-26 Procede de production des acyle lactames
BR9509585A BR9509585A (pt) 1994-11-03 1995-10-26 Processo para a produção de acil lactams
MX9703305A MX9703305A (es) 1994-11-03 1995-10-26 Procedimiento para la produccion de acilo lactamas.
CA 2204014 CA2204014A1 (fr) 1994-11-03 1995-10-26 Procede de production des acyle lactames

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9422153.8 1994-11-03
GB9422153A GB9422153D0 (en) 1994-11-03 1994-11-03 Process for the production of acyl lactams

Publications (1)

Publication Number Publication Date
WO1996014299A1 true WO1996014299A1 (fr) 1996-05-17

Family

ID=10763810

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1995/013818 WO1996014299A1 (fr) 1994-11-03 1995-10-26 Procede de production des acyle lactames

Country Status (6)

Country Link
EP (1) EP0789689A4 (fr)
AR (1) AR000070A1 (fr)
BR (1) BR9509585A (fr)
GB (1) GB9422153D0 (fr)
MX (1) MX9703305A (fr)
WO (1) WO1996014299A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0822184A1 (fr) * 1996-07-31 1998-02-04 Societe Nationale Des Poudres Et Explosifs Procédé de préparation de lactames N-substitués

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2877220A (en) * 1959-03-10 Method of preparing lysine
US3332939A (en) * 1967-07-25 Acylated lactams
WO1995000625A1 (fr) * 1993-06-25 1995-01-05 The Procter & Gamble Company Compositions detergentes granulaires pour la lessive, contenant une lipase et un sulfonate de nonanoyloxybenzene de sodium
US5405413A (en) * 1993-06-24 1995-04-11 The Procter & Gamble Co. Bleaching compounds comprising acyl valerolactam bleach activators
US5405412A (en) * 1994-04-13 1995-04-11 The Procter & Gamble Company Bleaching compounds comprising N-acyl caprolactam and alkanoyloxybenzene sulfonate bleach activators

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1445515A1 (de) * 1963-12-13 1969-02-13 Basf Ag Verfahren zur Herstellung von substituierten Lactamen
GB1343426A (en) * 1971-05-07 1974-01-10 Dow Corning Tld Acylated lactams
CH573404A5 (fr) * 1972-07-28 1976-03-15 Inventa Ag
DD299058A5 (de) * 1990-01-31 1992-03-26 Arzneimittelwerk Dresden Gmbh,De Verfahren zur herstellung von n-acyl-4-phenyl-pyrrolidin-2-onen mit cerebroprotektiver wirkung

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2877220A (en) * 1959-03-10 Method of preparing lysine
US3332939A (en) * 1967-07-25 Acylated lactams
US5405413A (en) * 1993-06-24 1995-04-11 The Procter & Gamble Co. Bleaching compounds comprising acyl valerolactam bleach activators
WO1995000625A1 (fr) * 1993-06-25 1995-01-05 The Procter & Gamble Company Compositions detergentes granulaires pour la lessive, contenant une lipase et un sulfonate de nonanoyloxybenzene de sodium
US5405412A (en) * 1994-04-13 1995-04-11 The Procter & Gamble Company Bleaching compounds comprising N-acyl caprolactam and alkanoyloxybenzene sulfonate bleach activators

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP0789689A4 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0822184A1 (fr) * 1996-07-31 1998-02-04 Societe Nationale Des Poudres Et Explosifs Procédé de préparation de lactames N-substitués
FR2751963A1 (fr) * 1996-07-31 1998-02-06 Poudres & Explosifs Ste Nale Procede de preparation de lactames n-substitues
US5986092A (en) * 1996-07-31 1999-11-16 Snpe Process for the preparation of N-substituted lactams

Also Published As

Publication number Publication date
BR9509585A (pt) 1997-12-23
EP0789689A1 (fr) 1997-08-20
GB9422153D0 (en) 1994-12-21
MX9703305A (es) 1997-08-30
EP0789689A4 (fr) 1998-02-25
AR000070A1 (es) 1997-05-21

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