CN106831451B - A kind of synthetic method of 2- aminoisobutanols - Google Patents

A kind of synthetic method of 2- aminoisobutanols Download PDF

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CN106831451B
CN106831451B CN201710062949.8A CN201710062949A CN106831451B CN 106831451 B CN106831451 B CN 106831451B CN 201710062949 A CN201710062949 A CN 201710062949A CN 106831451 B CN106831451 B CN 106831451B
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aminoisobutanols
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organic layer
caustic soda
layered
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CN106831451A (en
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胡莉萍
胡冠丰
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Shandong Youying New Materials Co.,Ltd.
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Jingchu University of Technology
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    • 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
    • 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
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/06—Preparation of carboxylic acid amides from nitriles by transformation of cyano groups into carboxamide groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

A kind of synthetic method of 2 aminoisobutanol, includes the following steps：Acetonitrile is added in 5 15 DEG C of sulfuric acid and is uniformly mixed, metering system chlorine is added, reaction is poured into ice water after 2.5 3.5 hours and is layered, and the excessive liquid caustic soda of mass concentration 10 50% is added in the organic layer separated, back hydrolysis is layered, and fractionation organic layer obtains 2 aminoisobutanols.Advantage is：The present invention uses isobutene relatively low for 2 amino butanol costs of raw material production, but due to chlorine to be used, sulfuric acid, liquid caustic soda, must will produce salt, is not a cleaning procedure, but it can break up monopoly, provides the user with 2 more cheap aminoisobutanols.

Description

A kind of synthetic method of 2- aminoisobutanols
Technical field
The present invention relates to organic chemical synthesis technical fields, and in particular to a kind of synthetic method of 2- aminoisobutanols.
Background technology
2- aminoisobutanols are a kind of surfactants, and performance is stablized, can be used for water paint PH stabilizer, can also make gold Belong to cutting fluid to use, play the role of lubrication cleaning section, can also form biological buffer with various acid, widely used, the whole world Dosage reaches tens thousand of tons.
The report of 2- aminoisobutanol synthetic methods sees US 2413153 in 1948 earliest, and US 2587572 uses 2- Nitropropane is that then hydrogenating reduction is made raw material with formaldehyde condensation.So far apparently this route is still most simple most environmentally friendly road Line was being modified all around this route later（See US 2485982, US 2673880, US 3564057, US 20160052868 ）.Since the raw materials for production of 2- nitropropanes only rest in only a few major company hand, 2- aminoisobutyrics Alcohol becomes a monopolization product, does not there is breakthrough for many years.Though having tried to method for distinguishing later, does not have industrial value, see CN 1810767, US 2006004045, CN 103130656 etc. is respectively original with isopropanol, acetone cyanohydrin, methylallyl alcohol Material synthesis 2- aminoisopropanols, fail large-scale production.Low not as good as 2- nitropropanes mainly in cost, technique is excessively complicated, and There is " three wastes " generation.
In recent years since preparing isobutene through dehydrogenation of iso-butane technology has breakthrough so that isobutene cost is down to 4000 yuan/ton, from And it is to have found new approach by Material synthesis 2- aminoisobutanols of isobutene.
Invention content
The purpose of the present invention is primarily to solve above-mentioned technical problem, and provide the synthetic method of 2- aminoisobutanols.
The present invention includes the following steps：A kind of synthetic method of 2- aminoisobutanols, includes the following steps：
1 mole of acetonitrile is added in 5-15 DEG C of 1 mol sulfuric acid and is uniformly mixed, adds 1 moles propylene chlorine, instead It pours into ice water and is layered after answering 2.5-3.5 hours, the excessive liquid caustic soda of mass concentration 10-50% is added in the organic layer separated, return Flowing water solution is layered, and fractionation organic layer obtains 0.8 mole of 2- aminoisobutanols.
Vacuum fractionation is collected, under 10mmHg pressure,Boiling point is that 65-67 DEG C of fraction is 2- aminoisobutanols, content 99.5%, yield 80%.
When the reaction of 1 moles propylene chlorine is added, 30 DEG C of controlling reaction temperature or less.
Liquid caustic soda is sodium hydroxide liquid caustic soda, potassium hydroxide liquid caustic soda.
The method have the advantages that：The present invention provides a kind of synthetic method of 2- aminoisobutanols into method, use isobutene for Raw material production 2- amino butanol costs are relatively low, but due to chlorine to be used, sulfuric acid, liquid caustic soda, must will produce salt, are not one clear Clean technique, but it can break up monopoly, and provide the user with more cheap 2- aminoisobutanols.
Specific implementation mode
The present invention includes the following steps：
1 mole of acetonitrile is added in 5-15 DEG C of 1 mol sulfuric acid and is uniformly mixed, adds 1 moles propylene chlorine, instead It pours into ice water and is layered after answering 2.5-3.5 hours, the excessive liquid caustic soda of mass concentration 10-50% is added in the organic layer separated, return Flowing water solution is layered, and fractionation organic layer obtains 0.8 mole of 2- aminoisobutanols.
Vacuum fractionation is collected, under 10mmHg pressure,Boiling point is that 65-67 DEG C of fraction is 2- aminoisobutanols, content 99.5%, yield 80%.
When the reaction of 1 moles propylene chlorine is added, 30 DEG C of controlling reaction temperature or less.
Liquid caustic soda is sodium hydroxide liquid caustic soda, potassium hydroxide liquid caustic soda
Example 1
1 mol sulfuric acid cools to 10 DEG C of additions, 1 mole of acetonitrile and is uniformly mixed, and 30 DEG C of temperature control is hereinafter, be added 1 moles third Alkene chlorine（Exothermic heat of reaction）, pour into ice water and be layered after reacting 3 hours, organic layer adds alkali back hydrolysis to be layered, and fractionation organic layer obtains 0.8 mole of 2- aminoisobutanol（Content 85%）, the third nitrogen of diformazan basic ring（Content 13%）, metering system chlorine（Content 2%）, decompression B is collected in fractionation1065~67 DEG C obtain 2- aminoisobutanols, content 99.5%, yield 80%（To consume in terms of metering system chlorine）.
Example 2
By example 1, changes metering system chlorine into metering system alcohol acetate and implement by example 1, obtain 2- aminoisobutanols 0.84 mole, content 99.7%, yield 84%（To consume in terms of metering system alcohol acetate）.
Example 3
It changes acetonitrile in example 1 into hydrogen cyanide, implements by example 1, obtain 0.85 mole of 2- aminoisobutanols, content 99.2% is received Rate 85%.
Example 4
Change metering system chlorine in example 1 into metering system alcohol acetate, acetonitrile changes hydrogen cyanide into, implements by example 1, obtains 2- ammonia 0.89 mole of base isobutanol, content 99.6%, yield 89%.
Its reactive chemistry equation is：
R ' is usually H or CH3, that is, select hydrogen cyanide or acetonitrile.
R " is usually H or CH3, i.e. formic acid or acetic acid.

Claims (1)

1. a kind of synthetic method of 2- aminoisobutanols, it is characterised in that it includes the following steps：
Acetonitrile is added in 5-15 DEG C of sulfuric acid and is uniformly mixed, add metering system chlorine, reaction is poured into after 2.5-3.5 hours It is layered in ice water, in the organic layer separated plus the excessive liquid caustic soda of mass concentration 10-50%, back hydrolysis layering, fractionation are organic Layer obtains 2- aminoisobutanols；Vacuum fractionation is collected, under 10mmHg pressure,Boiling point is that 65-67 DEG C of fraction is 2- aminoisobutyrics Alcohol.
CN201710062949.8A 2017-02-03 2017-02-03 A kind of synthetic method of 2- aminoisobutanols Active CN106831451B (en)

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Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3944617A (en) * 1976-02-20 1976-03-16 American Cyanamid Company Synthesis of dl-2-amino-1-butanol
CN1357534A (en) * 2001-07-20 2002-07-10 昆山双鹤药业有限责任公司 Prepn. of L-2-amino propanol
CN1810767A (en) * 2006-02-15 2006-08-02 符爱清 Production process of 2-amino-methyl-1-propanol
CN103130656A (en) * 2013-01-19 2013-06-05 烟台万华聚氨酯股份有限公司 Prepared method of 2-amino-2-methyl-1-propyl alcohol
CN103232351A (en) * 2013-04-27 2013-08-07 烟台万华聚氨酯股份有限公司 Preparation method of 2-amino-2-methyl-1-propyl alcohol
CN105001098A (en) * 2015-07-26 2015-10-28 嵊州市油脂化工有限公司 Method for preparing 3(R)/(S)-amidogen-1-butanol
CN105481703A (en) * 2016-01-13 2016-04-13 江西仙康药业有限公司 Method for synthesizing (S)-2-aminobutanol

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1984909A (en) * 2004-07-01 2007-06-20 霍夫曼-拉罗奇有限公司 Thiazolinone unsubstituted quinolines

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3944617A (en) * 1976-02-20 1976-03-16 American Cyanamid Company Synthesis of dl-2-amino-1-butanol
CN1357534A (en) * 2001-07-20 2002-07-10 昆山双鹤药业有限责任公司 Prepn. of L-2-amino propanol
CN1810767A (en) * 2006-02-15 2006-08-02 符爱清 Production process of 2-amino-methyl-1-propanol
CN103130656A (en) * 2013-01-19 2013-06-05 烟台万华聚氨酯股份有限公司 Prepared method of 2-amino-2-methyl-1-propyl alcohol
CN103232351A (en) * 2013-04-27 2013-08-07 烟台万华聚氨酯股份有限公司 Preparation method of 2-amino-2-methyl-1-propyl alcohol
CN105001098A (en) * 2015-07-26 2015-10-28 嵊州市油脂化工有限公司 Method for preparing 3(R)/(S)-amidogen-1-butanol
CN105481703A (en) * 2016-01-13 2016-04-13 江西仙康药业有限公司 Method for synthesizing (S)-2-aminobutanol

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