US2449152A - Separation of monoethanol amine from admixtures by azeotropic distillation with chlorobenzene - Google Patents

Separation of monoethanol amine from admixtures by azeotropic distillation with chlorobenzene Download PDF

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Publication number
US2449152A
US2449152A US657329A US65732946A US2449152A US 2449152 A US2449152 A US 2449152A US 657329 A US657329 A US 657329A US 65732946 A US65732946 A US 65732946A US 2449152 A US2449152 A US 2449152A
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United States
Prior art keywords
separation
chlorobenzene
admixture
dea
admixtures
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US657329A
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Jr John C Speck
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US Department of Navy
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US Department of Navy
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    • 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
    • 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
    • C07C213/10—Separation; Purification; Stabilisation; Use of additives
    • 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

Definitions

  • This invention relates to a method for separating one component from a mixture with one or more other components by the principle of azeotropism; in particular, it relates to a method of separating 'monoethanolamine (MEA) from admixture with diethanolamine (DEA) and thiethanolamine (TEA) by the addition to the admixture of a component which forms an azeotrope with the monoethanolamine.
  • MEA 'monoethanolamine
  • DEA diethanolamine
  • TEA thiethanolamine
  • this inventor has provided a method for the separation of MEA y from DEA and TEA which is based upon the fact that monochlorobenzene forms an azeotrope with MEA but not with DEA or TEA.
  • This azeotrope distills from admixture with the other components at a boiling point of 124 C. This is a lower boiling point than that of any of the components.
  • the method of separating monoethanolamine from admixture with diethanolamine and triethanolamine comprising the addition to the admixture of monochlorobenzene which is characterized by the ability to form an azeotrope with monoethanolamine' and distilling the azeotrope out from the admixture.
  • the method of separating monoethanolamine from admixture with diethanolamine and triethanolamine comprising the addition to the admixture of monochlorobenzene which is characterized by the ability to form an aaeotrope with monoethanolamine, heating the admixture to a temperature of approximately 124 0. whereby the azeotrope distills out from the admixture and the residual components are rendered substantially pure.

Description

Patented Sept. 14, 1948 SEPARATION OF MONOETHANOL AMINE FROM ADM'IXTURES BY AZEOTROPIC DISTILLATION WITH CHLOROBENZENE .lohn C. Speck, J r., Bloomington, Ind., assignor to the United States of America as represented by the Secretary of the Navy No Drawing. Application March 26, 1946, Serial No. 657,329
3 Claims. (01.202-42) This invention relates to a method for separating one component from a mixture with one or more other components by the principle of azeotropism; in particular, it relates to a method of separating 'monoethanolamine (MEA) from admixture with diethanolamine (DEA) and thiethanolamine (TEA) by the addition to the admixture of a component which forms an azeotrope with the monoethanolamine.
It is therefore an object of this invention to provide a method for the separation of MEA from admixture with DEA and TEA, and
It is also an object of this invention to provide a method for the separation of MEA from admixture with DEA and TEA which is based upon the principle of azeotroplsm, and
It is a further object of this invention to provide a method for the separation of MEAstrom admixture with DEA and TEA which is based upon the principle of azeotropism in which the azeotrope 'distills out of the admixture at a boiling point lower than that of any of the components.
with these objectives in view, this inventor has provided a method for the separation of MEA y from DEA and TEA which is based upon the fact that monochlorobenzene forms an azeotrope with MEA but not with DEA or TEA. This azeotrope distills from admixture with the other components at a boiling point of 124 C. This is a lower boiling point than that of any of the components.
The ,boiling points of the azeotrope components at 760 mm. Hg pressure are:
'' C. MEA 1'12 Monochlorobenzene 132 Azeotrope 124 The boiling point at 760 mm. pressure of DEA is 268 centigrade while that of TEA is 278 centigrade at 150 mm. Kg pressure.
The following test runs were made in veriilcation of'the method herein described and claimed.
A 5 to 6 gm. sample oi the DEA and MEA was Per cent MEA Known Mixture as determined (MEA and DEA) by Titration of Per cent MEA Areotropic Distillate Further test runs were made using pure DEA with chlorobenzene which resulted only in chlorobenzene being found in the distillate. The same was true of the test runs on pure TEA and also in a mixture of equal parts of DEA and TEA. In
all three cases only chlorobenzene was found in the distillate. The procedure was also found to be satisfactory when applied to the analysis of commercial samples of DEA which contained MEA as an impurity.
I claim:
1. The method of separating monoethanolamine from admixture with diethanolamine and triethanolamine comprising the addition to the admixture of monochlorobenzene which is characterized by the ability to form an azeotrope with monoethanolamine' and distilling the azeotrope out from the admixture.
2. The method of separating monoethanolamine from admixture with diethanolamine and triethanolaminecomprising the addition to the admixture of monochlorobenzene which is characterized by the ability to form an aaeotrope with monoethanolamine, heating the admixture to a temperature of approximately 124 0. whereby the azeotrope distills out from the admixture and the residual components are rendered substantially pure. a
3. The method of separating monoethanolamine from a mixture containing diethanolamine. consisting in adding monochlorobenzene to ilorm an'azeotrope with the monoethanolamine, and
then distilling out the azeotrope.
I JOHN c. sracx. Ja. REFERENCES crran The following references are of record in the file of this patent:
UNITED STATES PATENTS Number Name Date 2,091,636 Herold et al Aug. 81,198? .60 Andrews et a1. Aug. 9, i988
US657329A 1946-03-26 1946-03-26 Separation of monoethanol amine from admixtures by azeotropic distillation with chlorobenzene Expired - Lifetime US2449152A (en)

Priority Applications (1)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2940973A (en) * 1953-12-02 1960-06-14 Wyandotte Chemicals Corp Separation of isopropanolamine from mixtures thereof with 2, 5-dimethyl-piperazine by azeotropic distillation

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2091636A (en) * 1933-03-08 1937-08-31 Ig Farbenindustrie Ag Production of trimethylamine
US2126600A (en) * 1936-04-18 1938-08-09 Rohm & Haas Separation of methylamines

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2091636A (en) * 1933-03-08 1937-08-31 Ig Farbenindustrie Ag Production of trimethylamine
US2126600A (en) * 1936-04-18 1938-08-09 Rohm & Haas Separation of methylamines

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2940973A (en) * 1953-12-02 1960-06-14 Wyandotte Chemicals Corp Separation of isopropanolamine from mixtures thereof with 2, 5-dimethyl-piperazine by azeotropic distillation

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