GB1208569A - Process for the production of pyridines - Google Patents

Process for the production of pyridines

Info

Publication number
GB1208569A
GB1208569A GB57567A GB57567A GB1208569A GB 1208569 A GB1208569 A GB 1208569A GB 57567 A GB57567 A GB 57567A GB 57567 A GB57567 A GB 57567A GB 1208569 A GB1208569 A GB 1208569A
Authority
GB
United Kingdom
Prior art keywords
pyridines
pyridine
alkyl
cycloalkyl
aldehyde
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
GB57567A
Inventor
Hugh Bernard Charman
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB57567A priority Critical patent/GB1208569A/en
Priority to DE19681695296 priority patent/DE1695296A1/en
Publication of GB1208569A publication Critical patent/GB1208569A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/08—Preparation by ring-closure
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/08—Preparation by ring-closure
    • C07D213/09—Preparation by ring-closure involving the use of ammonia, amines, amine salts, or nitriles
    • C07D213/10—Preparation by ring-closure involving the use of ammonia, amines, amine salts, or nitriles from acetaldehyde or cyclic polymers thereof

Abstract

1,208,569. Pyridines. IMPERIAL CHEMICAL INDUSTRIES Ltd. 18 Dec., 1967 [4 Jan., 1967], No. 575/67. Heading C2C. Pyridine or an alkyl-, cycloalkyl- or hydropyridine is prepared by contacting an aldehyde RCH 2 .CHO, where R is hydrogen or a C 1-8 alkyl or cycloalkyl group, with an ammonium salt in a solution comprising a free acid R<SP>1</SP>COOH, where R<SP>1</SP> is a C 1-8 alkyl, cycloalkyl, or aryl group. A dialkyl or dicycloalkyl C 3-8 ketone or a second aldehyde of the formula R<SP>11</SP>CHO, where R<SP>11</SP> is hydrogen or a C 1-8 alkyl, cycloalkyl or aryl group, may also be present. The preferred ammonium salts are those derived from the acid R<SP>1</SP>COOH. To increase the yield of pyridines and alkyl pyridines, rather than hydrogenated pyridines, molecular oxygen may be present. It is preferred to operate in the presence of a catalyst which is a salt of a metal of variable valency, e.g. Mn, Cu, and Co. An additional solvent, e.g. ethyl acetate, dioxane, may be used. It is preferred to operate at 10- 200‹ C. Products obtained in the examples include 3,5-diethyl-2-propyl-pyridine, α-picoline, 2,3 - dihydro - 3,5 - diethyl - 2 - propyl - pyridine (which may disproportionate to 1,2,3,6-tetrahydro-pyridine), pyridine and vinyl pyridines. Some 2-ethyl-hexenal is obtained when the aldehyde is n-butyraldehyde.
GB57567A 1967-01-04 1967-01-04 Process for the production of pyridines Expired GB1208569A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB57567A GB1208569A (en) 1967-01-04 1967-01-04 Process for the production of pyridines
DE19681695296 DE1695296A1 (en) 1967-01-04 1968-01-03 Process for the preparation of pyridines

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB57567A GB1208569A (en) 1967-01-04 1967-01-04 Process for the production of pyridines

Publications (1)

Publication Number Publication Date
GB1208569A true GB1208569A (en) 1970-10-14

Family

ID=9706805

Family Applications (1)

Application Number Title Priority Date Filing Date
GB57567A Expired GB1208569A (en) 1967-01-04 1967-01-04 Process for the production of pyridines

Country Status (2)

Country Link
DE (1) DE1695296A1 (en)
GB (1) GB1208569A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0040698A1 (en) * 1980-05-23 1981-12-02 Lonza Ag Process for the preparation of 3-picoline
EP0056496A1 (en) * 1981-01-09 1982-07-28 Lonza Ag Method for the manufacture of 3-picoline
CN115286567A (en) * 2022-08-12 2022-11-04 镇江中智化学科技有限公司 One-pot synthesis of 3-bromopyridine

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FI77025C (en) * 1981-03-18 1989-01-10 Lonza Ag FOERFARANDE FOER FRAMSTAELLNING AV 3-PIKOLIN.
CH656879A5 (en) * 1981-07-09 1986-07-31 Lonza Ag METHOD FOR PRODUCING 3,5-DIALKYLPYRIDINE.
CH660733A5 (en) * 1981-09-29 1987-06-15 Lonza Ag METHOD FOR PRODUCING 3-PICOLIN.

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0040698A1 (en) * 1980-05-23 1981-12-02 Lonza Ag Process for the preparation of 3-picoline
US4337342A (en) * 1980-05-23 1982-06-29 Lonza Ltd. Process for the preparation of 3-picoline
EP0056496A1 (en) * 1981-01-09 1982-07-28 Lonza Ag Method for the manufacture of 3-picoline
CN115286567A (en) * 2022-08-12 2022-11-04 镇江中智化学科技有限公司 One-pot synthesis of 3-bromopyridine
CN115286567B (en) * 2022-08-12 2024-04-19 镇江中智化学科技有限公司 One-pot synthesis of 3-bromopyridine

Also Published As

Publication number Publication date
DE1695296A1 (en) 1972-02-24

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Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees