GB969993A - Process for the purification of lactams - Google Patents

Process for the purification of lactams

Info

Publication number
GB969993A
GB969993A GB36490/62A GB3649062A GB969993A GB 969993 A GB969993 A GB 969993A GB 36490/62 A GB36490/62 A GB 36490/62A GB 3649062 A GB3649062 A GB 3649062A GB 969993 A GB969993 A GB 969993A
Authority
GB
United Kingdom
Prior art keywords
hydrogen
lactam
treatment
purified
lactams
Prior art date
Legal status (The legal status 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 status listed.)
Expired
Application number
GB36490/62A
Inventor
Dieter Weiser
Horst Metzger
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Badische Anilin and Sodafabrik AG
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 BASF SE, Badische Anilin and Sodafabrik AG filed Critical BASF SE
Publication of GB969993A publication Critical patent/GB969993A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D201/00—Preparation, separation, purification or stabilisation of unsubstituted lactams
    • C07D201/02—Preparation of lactams
    • C07D201/08—Preparation of lactams from carboxylic acids or derivatives thereof, e.g. hydroxy carboxylic acids, lactones or nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D201/00—Preparation, separation, purification or stabilisation of unsubstituted lactams
    • C07D201/16—Separation or purification
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
    • C07D207/267—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atom

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Polyamides (AREA)
  • Pyrrole Compounds (AREA)

Abstract

Lactams containing 4-12 carbon atoms are purified by treatment with activated hydrogen in the presence of acids at a pH of 3 to 0.5, the lactam being in the liquid phase, preferably dissolved in water or in an inert solvent. The acids may be mineral or organic acids having a pH of 4.9 or less, e.g., sulphuric, hydrochloric, formic or acetic, and are used in amounts of 0.01-10.0%, preferably 0.1-10.0%, by weight of lactam. The activated hydrogen may be in the form of nascent hydrogen or catalytically activated hydrogen. In the former instance, nascent hydrogen is generated in the reaction mixture by a process which takes place in an acid medium but under conditions which leave the lactams unattacked, e.g. sodium borohydride and zinc dust and acids, preferably in the presence of an hydrogenation catalyst. Sufficient reagent to provide 0.001-0.5, particularly 0.001-0.2, moles of hydrogen per mole of lactam is employed. The treatment may be carried out in 20-80% by weight solutions in the temperature range -15-250 DEG C., preferably 50-100 DEG C. and at pressures ranging from normal to 10 atmospheres for times of up to 5 hours. When catalytically activated hydrogen is employed the catalyst, generally 0.1-5% by weight of lactam, may be, e.g. palladium, platinum, nickel or noble metal oxides and may be supported on a carrier. Pressures of 1-300 atmospheres may be used at temperatures in the range -15-250 DEG C., particularly 0-120 DEG C., and treatment continued until hydrogen uptake ceases or falls off. Where necessary the lactam is isolated by neutralization and/or filtration and distillation or sublimation. Lactams purified by the present process give polymers of improved colour rating, permanganate number and volatile base number (see Division C3). Examples (1)-(12) describe the treatment of caprolactam with catalytically activated hydrogen and nascent hydrogen. In Example (B) pyrrolidone is treated with catalytically activated hydrogen. Specification 904,302 is referred to.ALSO:Polyamides are made from lactams containing 4-12 carbon atoms which have been purified by treatment in the liquid-phase, preferably dissolved in water or in an inert solvent, and in an acid medium at pH 3-0.5 with activated hydrogen. The hydrogen can be in the nascent state or catalytically activated using the usual hydrogenation catalysts. In examples caprolactam and pyrrolidene are purified and polymerized by heating with 3% hexamethylene-diammonium adipate under an atmosphere of N2 for 6 hours at 260-270 DEG C. The polymers have colour ratings on the Hagen scale of 40-80. Specification 904,302 is referred to.
GB36490/62A 1961-09-28 1962-09-26 Process for the purification of lactams Expired GB969993A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEB64170A DE1253716B (en) 1961-09-28 1961-09-28 Process for purifying lactams

Publications (1)

Publication Number Publication Date
GB969993A true GB969993A (en) 1964-09-16

Family

ID=6974280

Family Applications (1)

Application Number Title Priority Date Filing Date
GB36490/62A Expired GB969993A (en) 1961-09-28 1962-09-26 Process for the purification of lactams

Country Status (2)

Country Link
DE (1) DE1253716B (en)
GB (1) GB969993A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5032684A (en) * 1989-08-02 1991-07-16 Basf Aktiengesellschaft Continuous purification of caprolactam
US5952493A (en) * 1996-06-13 1999-09-14 Basf Aktiengesellschaft Method of purifying ε-caprolactam
US6677449B2 (en) 2000-05-03 2004-01-13 Basf Aktiengesellschaft Preparation of caprolactam
US6683179B2 (en) 2000-05-03 2004-01-27 Basf Aktiengesellschaft Preparation of caprolactam
US6878798B2 (en) 2000-05-03 2005-04-12 Basf Aktiengesellschaft Method for producing a polymer, using caprolactam
US8816069B2 (en) 2010-03-15 2014-08-26 Ube Industries, Ltd. Method for producing amide compound

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SG50773A1 (en) * 1993-06-04 1998-07-20 Dsm Nv Reclaiming e-caprolactam from carpet waste
TW268941B (en) * 1993-08-20 1996-01-21 Sumitomo Chemical Co
FR2786180B1 (en) 1998-11-19 2001-11-23 Rhone Poulenc Fibres LACTAM TREATMENT METHOD AND LACTAM PURIFICATION METHOD
DE10253094A1 (en) 2002-11-13 2004-05-27 Basf Ag Purification of crude caprolactam comprises a three stage distillation process with feeding of the crude caprolactam and an inorganic acid having a b. pt. above the b. pt. of the caprolactam to a first distillation column
DE10253095A1 (en) 2002-11-13 2004-06-17 Basf Ag Process for the purification of caprolactam

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE739953C (en) * 1940-12-03 1943-10-26 Ig Farbenindustrie Ag Process for purifying lactams
DE745224C (en) * 1941-06-28 1944-03-01 Ig Farbenindustrie Ag Process for purifying lactams

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5032684A (en) * 1989-08-02 1991-07-16 Basf Aktiengesellschaft Continuous purification of caprolactam
US5952493A (en) * 1996-06-13 1999-09-14 Basf Aktiengesellschaft Method of purifying ε-caprolactam
US6677449B2 (en) 2000-05-03 2004-01-13 Basf Aktiengesellschaft Preparation of caprolactam
US6683179B2 (en) 2000-05-03 2004-01-27 Basf Aktiengesellschaft Preparation of caprolactam
US6878798B2 (en) 2000-05-03 2005-04-12 Basf Aktiengesellschaft Method for producing a polymer, using caprolactam
US8816069B2 (en) 2010-03-15 2014-08-26 Ube Industries, Ltd. Method for producing amide compound
US8962826B2 (en) 2010-03-15 2015-02-24 Ube Industries, Ltd. Method for producing amide compound
US9242931B2 (en) 2010-03-15 2016-01-26 Ube Industries, Ltd. Method for producing amide compound

Also Published As

Publication number Publication date
DE1253716B (en) 1967-11-09

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