GB710861A - Process for the manufacture of alkanolamines - Google Patents

Process for the manufacture of alkanolamines

Info

Publication number
GB710861A
GB710861A GB3101850A GB3101850A GB710861A GB 710861 A GB710861 A GB 710861A GB 3101850 A GB3101850 A GB 3101850A GB 3101850 A GB3101850 A GB 3101850A GB 710861 A GB710861 A GB 710861A
Authority
GB
United Kingdom
Prior art keywords
epoxybutane
ammonia
heated
butanolamine
cis
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
GB3101850A
Inventor
Archibald Robert Graham
Alfred Frank Millidge
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.)
Distillers Co Yeast Ltd
Distillers Co Ltd
Original Assignee
Distillers Co Yeast Ltd
Distillers Co 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
Priority to BE507746D priority Critical patent/BE507746A/xx
Priority to NL81742D priority patent/NL81742C/xx
Application filed by Distillers Co Yeast Ltd, Distillers Co Ltd filed Critical Distillers Co Yeast Ltd
Priority to GB3101850A priority patent/GB710861A/en
Priority to FR1056133D priority patent/FR1056133A/en
Priority to DED11133A priority patent/DE908972C/en
Publication of GB710861A publication Critical patent/GB710861A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/04—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reaction of ammonia or amines with olefin oxides or halohydrins
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
    • C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
    • C07C215/08—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic with only one hydroxy group and one amino group bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
    • C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
    • C07C215/12—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic the nitrogen atom of the amino group being further bound to hydrocarbon groups substituted by hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Mono- and di-2 : 3-butanolamines, substantially free from tributanolamines, are manufactured by reacting 2 : 3-epoxybutane with ammonia, advantageously at 70-180 DEG C. (preferably 90-120 DEG C.). The starting material should be practically free from 1 : 2-epoxybutane, i.e. the proportion of the latter should be less than 30 per cent, preferably less than 5 per cent, a suitable starting material being the product obtained by liquid phase oxidation with molecular oxygen of a butene-2 containing not more than 10 per cent of butene-1. The molar ratio of ammonia to 2 : 3-epoxybutane is advantageously less than 10 : 1, preferably less than 5 : 1. If it is 1 : 2, the product is substantially pure di-2 : 3-butanolamine. With excess of aqueous ammonia, mono-2 : 3-butanolamine is mainly formed, pure trans- and cis-2 : 3-epoxybutane yielding respectively the erythro- and threo-forms thereof, which are characterized by their normal (erythro only) and acid oxalates, N-benzoyl, N-p-nitrobenzoyl and N-p-toluenesulphonyl derivatives and phenylthioureides. In examples: (1) pure trans-2 : 3-epoxybutane is heated with 3 molecular proportions of aqueous ammonia to produce a mixture of mono- and di-2 : 3-butanolamines from which the former (erythro-form) crystallizes on standing; (2) the molar ratio of ammonia to epoxybutane in (1) is reduced to 1 : 2, the product being mainly di-2 : 3-butanolamine; (3) cis-2 : 3-epoxybutane is treated as in (1), but using 4.5 molecular proportions of ammonia, yielding threo-3-aminobutan-2-ol and some di-2 : 3-butanolamine; (4) cis-2 : 3-epoxybutane is treated as in (2); (5) a mixture of cis- and trans-compounds is heated with 5 molecular proportions of aqueous ammonia; (6) a mixture somewhat richer in cis-compound is heated with 0.34, 0.55, 1.0, 1.25, 2.5 or 5.0 molecular proportions of aqueous ammonia; (7) the starting material of (5) is heated with 5.5 molecular proportions of aqueous ammonia in a continuous process; (8) similar starting materials are similarly heated with 5.3 or 5.1 molecular proportions of ammonia. Experiments are also described in which (a) di-2 : 3-butanolamine is heated with 1 : 2-epoxybutane in the presence of water, forming a mixed tributanolamine, and (b) a 1 : 2-mixture of 1 : 2-and trans-2 : 3-epoxybutanes is heated with aqueous ammonia, the molar ratio of ammonia to total epoxides being 1 : 2, whereby a mixed dibutanolamine is formed together with a mixed tributanolamine. Specification 708,913 is referred to. 2 : 3 : 5 : 6-Tetramethylmorpholine is obtainable by dehydration of di-2 : 3-butanolamine, e.g. with concentrated sulphuric acid. Specifications 448,373 and 497,093 also are referred to.
GB3101850A 1950-12-20 1950-12-20 Process for the manufacture of alkanolamines Expired GB710861A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
BE507746D BE507746A (en) 1950-12-20
NL81742D NL81742C (en) 1950-12-20
GB3101850A GB710861A (en) 1950-12-20 1950-12-20 Process for the manufacture of alkanolamines
FR1056133D FR1056133A (en) 1950-12-20 1951-12-13 Improvements in alkanolamine preparation processes
DED11133A DE908972C (en) 1950-12-20 1951-12-16 Process for the preparation of alkanolamines

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3101850A GB710861A (en) 1950-12-20 1950-12-20 Process for the manufacture of alkanolamines

Publications (1)

Publication Number Publication Date
GB710861A true GB710861A (en) 1954-06-23

Family

ID=10316686

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3101850A Expired GB710861A (en) 1950-12-20 1950-12-20 Process for the manufacture of alkanolamines

Country Status (5)

Country Link
BE (1) BE507746A (en)
DE (1) DE908972C (en)
FR (1) FR1056133A (en)
GB (1) GB710861A (en)
NL (1) NL81742C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3544632A (en) * 1967-04-13 1970-12-01 Basf Ag Production of alkanolamines-(1,2) or cycloalkanolamines-(1,2)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3544632A (en) * 1967-04-13 1970-12-01 Basf Ag Production of alkanolamines-(1,2) or cycloalkanolamines-(1,2)

Also Published As

Publication number Publication date
FR1056133A (en) 1954-02-24
NL81742C (en)
BE507746A (en)
DE908972C (en) 1954-04-12

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