NL8105278A - Werkwijze voor de bereiding van een lactam. - Google Patents

Werkwijze voor de bereiding van een lactam. Download PDF

Info

Publication number: NL8105278A
Authority: NL; Netherlands
Prior art keywords: process according; alkali metal; ester; reductive amination; catalyst
Prior art date: 1981-11-21

Application number

NL8105278A

Other languages

English (en)

Dutch (nl)

Original Assignee

Stamicarbon

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.)

1981-11-21

Filing date

1981-11-21

Publication date

1983-06-16

1981-11-21 Application filed by Stamicarbon filed Critical Stamicarbon

1981-11-21 Priority to NL8105278A priority Critical patent/NL8105278A/nl

1982-11-19 Priority to EP82201472A priority patent/EP0080240B1/de

1982-11-19 Priority to JP57203529A priority patent/JPS5892657A/ja

1982-11-19 Priority to AT82201472T priority patent/ATE18206T1/de

1982-11-19 Priority to DE8282201472T priority patent/DE3269484D1/de

1983-06-16 Publication of NL8105278A publication Critical patent/NL8105278A/nl

1984-08-31 Priority to US06/646,049 priority patent/US4560760A/en

Links

150000003951 lactams Chemical class 0.000 title claims abstract description 10
238000000034 method Methods 0.000 title claims description 20
238000002360 preparation method Methods 0.000 title claims description 6
239000003054 catalyst Substances 0.000 claims abstract description 26
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 22
229910052783 alkali metal Inorganic materials 0.000 claims abstract description 13
150000001340 alkali metals Chemical class 0.000 claims abstract description 12
229910021529 ammonia Inorganic materials 0.000 claims abstract description 11
238000005984 hydrogenation reaction Methods 0.000 claims abstract description 11
125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims abstract description 11
238000006268 reductive amination reaction Methods 0.000 claims abstract description 11
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
239000001257 hydrogen Substances 0.000 claims abstract description 9
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims abstract description 5
239000007789 gas Substances 0.000 claims abstract description 5
229910052708 sodium Inorganic materials 0.000 claims abstract description 5
239000011734 sodium Substances 0.000 claims abstract description 5
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
150000002148 esters Chemical class 0.000 claims description 11
239000002253 acid Substances 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 7
239000007858 starting material Substances 0.000 claims description 7
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
150000001721 carbon Chemical group 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
229910052763 palladium Inorganic materials 0.000 claims description 4
-1 isopropyl ester Chemical class 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
229910052759 nickel Inorganic materials 0.000 claims description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
238000006243 chemical reaction Methods 0.000 abstract description 7
125000000217 alkyl group Chemical group 0.000 abstract description 3
125000005907 alkyl ester group Chemical group 0.000 abstract 1
150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
238000004519 manufacturing process Methods 0.000 abstract 1
239000000376 reactant Substances 0.000 abstract 1
AVVPOKSKJSJVIX-UHFFFAOYSA-N methyl 5-oxohexanoate Chemical compound COC(=O)CCCC(C)=O AVVPOKSKJSJVIX-UHFFFAOYSA-N 0.000 description 6
150000007513 acids Chemical class 0.000 description 5
239000000463 material Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 3
239000000203 mixture Substances 0.000 description 3
JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
125000004185 ester group Chemical group 0.000 description 2
238000010574 gas phase reaction Methods 0.000 description 2
239000008246 gaseous mixture Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
238000006722 reduction reaction Methods 0.000 description 2
IEHMHYAHHVRZIF-UHFFFAOYSA-N 4-methyl-5-oxohexanoic acid Chemical compound CC(=O)C(C)CCC(O)=O IEHMHYAHHVRZIF-UHFFFAOYSA-N 0.000 description 1
MGTZCLMLSSAXLD-UHFFFAOYSA-N 5-oxohexanoic acid Chemical compound CC(=O)CCCC(O)=O MGTZCLMLSSAXLD-UHFFFAOYSA-N 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
150000001339 alkali metal compounds Chemical class 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000000428 dust Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012530 fluid Substances 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
229910002804 graphite Inorganic materials 0.000 description 1
239000010439 graphite Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229940040102 levulinic acid Drugs 0.000 description 1
238000002156 mixing Methods 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004033 plastic Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
229910052814 silicon oxide Inorganic materials 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
230000004580 weight loss Effects 0.000 description 1

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
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Hydrogenated Pyridines (AREA)
Cephalosporin Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

NL8105278A 1981-11-21 1981-11-21 Werkwijze voor de bereiding van een lactam. NL8105278A (nl)

Priority Applications (6)

Application Number	Priority Date	Filing Date	Title
NL8105278A NL8105278A (nl)	1981-11-21	1981-11-21	Werkwijze voor de bereiding van een lactam.
EP82201472A EP0080240B1 (de)	1981-11-21	1982-11-19	Verfahren zur Herstellung eines Laktams
JP57203529A JPS5892657A (ja)	1981-11-21	1982-11-19	ラクタムの製造方法
AT82201472T ATE18206T1 (de)	1981-11-21	1982-11-19	Verfahren zur herstellung eines laktams.
DE8282201472T DE3269484D1 (en)	1981-11-21	1982-11-19	Process for the preparation of a lactam
US06/646,049 US4560760A (en)	1981-11-21	1984-08-31	Process for the preparation of a lactam

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
NL8105278A NL8105278A (nl)	1981-11-21	1981-11-21	Werkwijze voor de bereiding van een lactam.
NL8105278		1981-11-21

Publications (1)

Publication Number	Publication Date
NL8105278A true NL8105278A (nl)	1983-06-16

Family

ID=19838427

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8105278A NL8105278A (nl)	1981-11-21	1981-11-21	Werkwijze voor de bereiding van een lactam.

Country Status (6)

Country	Link
US (1)	US4560760A (de)
EP (1)	EP0080240B1 (de)
JP (1)	JPS5892657A (de)
AT (1)	ATE18206T1 (de)
DE (1)	DE3269484D1 (de)
NL (1)	NL8105278A (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6828277B2 (en) *	2003-03-24	2004-12-07	E. I. Du Pont De Nemours And Company	Production of N-aryl-2-lactam and N-alkyl-2-lactam by reductive amination of lactones with aryl and alkyl nitro compounds
US6855731B2 (en) *	2003-03-24	2005-02-15	E. I. Du Pont De Nemours And Company	Production of 5-methyl-N-aryl-2-pyrrolidone and 5-methyl-N-alkyl-2-pyrrolidone by reductive amination of levulinic acid esters with nitro compounds
US6818593B2 (en) *	2003-03-24	2004-11-16	E. I. Du Pont De Nemours And Company	Production of 5-Methyl-N-aryl-2-pyrrolidone and 5-methyl-N-alkyl-2-pyrrolidone by reductive amination of levulinic acid with nitro compounds

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3235562A (en) *	1962-01-29	1966-02-15	Crown Zellerbach Corp	Making lactams by the vapor phase reductive amination of oxo carboxylic acid compounds
LU53600A1 (de) *	1966-05-10	1967-07-05
US4200553A (en) *	1977-08-23	1980-04-29	Allied Chemical Corporation	Process for producing cyclohexanone
US4162267A (en) *	1978-06-22	1979-07-24	Allied Chemical Corporation	Production of cyclohexanone
NL7902537A (nl) *	1979-04-01	1980-10-03	Stamicarbon	Werkwijze voor de bereiding van een eventueel c-gesubstitueerd 2-pyrrolidon en daarbij te gebruiken katalysator.

1981
- 1981-11-21 NL NL8105278A patent/NL8105278A/nl not_active Application Discontinuation
1982
- 1982-11-19 JP JP57203529A patent/JPS5892657A/ja active Pending
- 1982-11-19 AT AT82201472T patent/ATE18206T1/de not_active IP Right Cessation
- 1982-11-19 DE DE8282201472T patent/DE3269484D1/de not_active Expired
- 1982-11-19 EP EP82201472A patent/EP0080240B1/de not_active Expired
1984
- 1984-08-31 US US06/646,049 patent/US4560760A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
EP0080240A1 (de)	1983-06-01
US4560760A (en)	1985-12-24
ATE18206T1 (de)	1986-03-15
JPS5892657A (ja)	1983-06-02
DE3269484D1 (en)	1986-04-03
EP0080240B1 (de)	1986-02-26

Legal Events

Date	Code	Title
1983-06-16	A1B	A search report has been drawn up
1985-01-01	A85	Still pending on 85-01-01
1986-07-01	BV	The patent application has lapsed

Publication	Publication Date	Title
US4420622A (en)	1983-12-13	Process for the preparation of a 5-alkyl-butyrolactone
EP1419139A1 (de)	2004-05-19	Synthese ungesättigter nitrile aus lactonen
US3442910A (en)	1969-05-06	Preparation of hydrocoumarin,coumarin and alkyl substituted derivatives
JPWO1993002046A1 (ja)	1993-08-05	ニトリルの製造方法
US3235562A (en)	1966-02-15	Making lactams by the vapor phase reductive amination of oxo carboxylic acid compounds
US2532277A (en)	1950-12-05	1, 6 hexanediamine derivatives
US3515740A (en)	1970-06-02	Cyano cyclohexenyl compounds
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WO2004007421A1 (en)	2004-01-22	Synthesis of alkenoate esters from lactones and alcohols
US4560760A (en)	1985-12-24	Process for the preparation of a lactam
US6166207A (en)	2000-12-26	Preparation of bicyclic amidines and diazacycloalkenes
US5103055A (en)	1992-04-07	Water-promoted synthesis of amides from nitriles and alcohols
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US4599421A (en)	1986-07-08	Process for the preparation of a pyridone-2
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JPH0678304B2 (ja)	1994-10-05	Ｎ−アルキル置換ラクタムの製造方法
US4132711A (en)	1979-01-02	Process for preparing nitriles
US6384263B1 (en)	2002-05-07	Process for making 3-hydroxyalkanelnitriles and conversion of the 3-hydroxyalkanelnitrile to an hydroxyaminoalkane
US4419297A (en)	1983-12-06	Preparation of nitriles from formamides
JPH0753493A (ja)	1995-02-28	酸化又はアンモ酸化の供給原料としての粗アセトニトリルの安定化方法
JPS63243064A (ja)	1988-10-07	ベンゾニトリル類の製法
US5099066A (en)	1992-03-24	Synthesis of N-substituted amides by condensation of nitriles with certain organic hydroxyl compounds