CN106831451A - A kind of synthetic method of 2 aminoisobutanol - Google Patents
A kind of synthetic method of 2 aminoisobutanol Download PDFInfo
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- CN106831451A CN106831451A CN201710062949.8A CN201710062949A CN106831451A CN 106831451 A CN106831451 A CN 106831451A CN 201710062949 A CN201710062949 A CN 201710062949A CN 106831451 A CN106831451 A CN 106831451A
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- aminoisobutanol
- caustic soda
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- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 title claims abstract description 27
- 238000010189 synthetic method Methods 0.000 title claims abstract description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 39
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000007788 liquid Substances 0.000 claims abstract description 15
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 14
- 235000011121 sodium hydroxide Nutrition 0.000 claims abstract description 13
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000012044 organic layer Substances 0.000 claims abstract description 10
- 239000005457 ice water Substances 0.000 claims abstract description 5
- 239000010410 layer Substances 0.000 claims abstract description 5
- 238000010992 reflux Methods 0.000 claims abstract description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 238000004508 fractional distillation Methods 0.000 claims description 6
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 3
- 238000005194 fractionation Methods 0.000 claims 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 abstract description 10
- 238000000034 method Methods 0.000 abstract description 6
- 239000002994 raw material Substances 0.000 abstract description 6
- JCBPETKZIGVZRE-UHFFFAOYSA-N 2-aminobutan-1-ol Chemical compound CCC(N)CO JCBPETKZIGVZRE-UHFFFAOYSA-N 0.000 abstract description 3
- 150000003839 salts Chemical class 0.000 abstract description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 1
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical group N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 6
- 239000003513 alkali Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- FGLBSLMDCBOPQK-UHFFFAOYSA-N 2-nitropropane Chemical compound CC(C)[N+]([O-])=O FGLBSLMDCBOPQK-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- TZODSDSWNKTCFL-UHFFFAOYSA-N acetyl 2-methylprop-2-enoate Chemical compound CC(=O)OC(=O)C(C)=C TZODSDSWNKTCFL-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000003518 caustics Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000013517 stratification Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 description 1
- BYDRTKVGBRTTIT-UHFFFAOYSA-N 2-methylprop-2-en-1-ol Chemical compound CC(=C)CO BYDRTKVGBRTTIT-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000006177 biological buffer Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000002173 cutting fluid Substances 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- DYVUNUQDYHPXSU-UHFFFAOYSA-N n,n-dimethylcyclopropanamine Chemical compound CN(C)C1CC1 DYVUNUQDYHPXSU-UHFFFAOYSA-N 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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
-
- 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
一种2‑氨基异丁醇的合成方法，包括以下步骤：将乙腈加入到5‑15℃的硫酸中混合均匀，再加入甲基丙烯氯，反应2.5‑3.5小时后倒入冰水中分层，在分出的有机层中加质量浓度10‑50％的过量液碱,回流水解分层,分馏有机层得2‑氨基异丁醇。优点是：本发明采用异丁烯为原料生产2‑氨基丁醇成本较低，但由于要用到氯气、硫酸、液碱，必定会产生盐，不是一条清洁工艺，但它会打破垄断，给用户提供更廉价的2‑氨基异丁醇。A kind of synthetic method of 2-aminoisobutanol, comprises the following steps: acetonitrile is added in the sulfuric acid of 5-15 ℃ and mixes homogeneously, then adds methacrylic chloride, reacts for 2.5-3.5 hours and pours into ice water layering, Add excess liquid caustic soda with a mass concentration of 10-50% to the separated organic layer, reflux and hydrolyze the layers, and fractionally distill the organic layer to obtain 2-aminoisobutanol. The advantage is: the present invention adopts isobutene as raw material to produce 2-aminobutanol, and the cost is relatively low, but because chlorine gas, sulfuric acid, and liquid caustic soda are used, salt must be produced. It is not a clean process, but it will break the monopoly and provide users with Cheaper 2‑aminoisobutanol.
Description
技术领域technical field
本发明涉及有机化学合成技术领域，具体涉及一种2-氨基异丁醇的合成方法。The invention relates to the technical field of organic chemical synthesis, in particular to a method for synthesizing 2-aminoisobutanol.
背景技术Background technique
2-氨基异丁醇是一种表面活性剂，性能稳定，可用于水性涂料PH稳定剂，也可作金属切削液使用，起到润滑清洁切面的作用，还可与各种酸形成生物缓冲剂，用途广泛，全球用量达数万吨。2-Aminoisobutanol is a surfactant with stable performance. It can be used as a pH stabilizer for water-based coatings, and can also be used as a metal cutting fluid to lubricate and clean cut surfaces. It can also form biological buffers with various acids , has a wide range of uses, and the global consumption reaches tens of thousands of tons.
2-氨基异丁醇合成方法的报导最早见于1948年US 2413153 ，US 2587572 采用2-硝基丙烷为原料与甲醛缩合然后加氢还原制得。至今看来这条路线仍是最简单最环保的路线，后来一直围绕这条路线在进行修饰（见 US 2485982 ，US 2673880 ，US 3564057 ，US20160052868 ）。由于2-硝基丙烷的生产原料仅掌握在极少数大公司手中，因此2-氨基异丁醇成为一个垄断产品，多年来未有突破。后来虽有人尝试别的方法，均不具工业价值，见 CN1810767 ，US 2006004045 ，CN 103130656 等，分别以异丙醇、丙酮氰醇、甲基丙烯醇为原料合成2-氨基异丙醇，未能规模生产。主要是成本上不及2-硝基丙烷低，工艺过于复杂，并有“三废”产生。The report on the synthesis method of 2-aminoisobutanol was first seen in US 2413153 in 1948, and US 2587572 was prepared by condensing 2-nitropropane with formaldehyde and then hydrogenating and reducing it as a raw material. So far it seems that this route is still the simplest and most environmentally friendly route, and has been modified around this route (see US 2485982, US 2673880, US 3564057, US20160052868). Since the raw materials for the production of 2-nitropropane are only in the hands of a very small number of large companies, 2-aminoisobutanol has become a monopoly product, and there has been no breakthrough for many years. Although some people tried other methods afterwards, they all had no industrial value. See CN1810767, US 2006004045, CN 103130656, etc., respectively using isopropanol, acetone cyanohydrin, and methacryl alcohol as raw materials to synthesize 2-aminoisopropanol. Production. The main reason is that the cost is not as low as that of 2-nitropropane, the process is too complicated, and "three wastes" are produced.
近年来由于异丁烷脱氢制异丁烯技术有突破，使得异丁烯成本降至4000元/吨，从而为以异丁烯为原料合成2-氨基异丁醇找到了新的途径。In recent years, due to breakthroughs in isobutane dehydrogenation to isobutene technology, the cost of isobutene has dropped to 4,000 yuan/ton, thus finding a new way for the synthesis of 2-aminoisobutanol using isobutene as raw material.
发明内容Contents of the invention
本发明的目的主要是为了解决上述技术问题，而提供2-氨基异丁醇的合成方法。The purpose of the present invention is mainly in order to solve the problems of the technologies described above, and the synthetic method of 2-aminoisobutanol is provided.
本发明包括以下步骤：一种2-氨基异丁醇的合成方法，包括以下步骤：The present invention comprises the following steps: a kind of synthetic method of 2-aminoisobutanol comprises the following steps:
将1摩尔乙腈加入到5-15℃的1摩尔硫酸中混合均匀，再加入1摩尔甲基丙烯氯，反应2.5-3.5小时后倒入冰水中分层，在分出的有机层中加质量浓度10-50％的过量液碱,回流水解分层,分馏有机层得0.8摩尔的2-氨基异丁醇。Add 1 mole of acetonitrile to 1 mole of sulfuric acid at 5-15°C and mix evenly, then add 1 mole of methacrylic chloride, react for 2.5-3.5 hours, pour into ice water to separate layers, and add mass concentration to the separated organic layer 10-50% excess liquid caustic soda, reflux, hydrolysis and stratification, and fractional distillation of the organic layer to obtain 0.8 mole of 2-aminoisobutanol.
减压分馏收集, 在10mmHg压力下, 沸点为65-67℃馏份为2-氨基异丁醇，含量99.5% ，收率80%。Collected by fractional distillation under reduced pressure, under 10mmHg pressure , the fraction with a boiling point of 65-67°C is 2-aminoisobutanol with a content of 99.5% and a yield of 80%.
加入1摩尔甲基丙烯氯反应时，控制反应温度30℃以下。When adding 1 mole of methacrylic chloride for reaction, control the reaction temperature below 30°C.
液碱是氢氧化钠液碱、氢氧化钾液碱。Liquid caustic soda is sodium hydroxide liquid caustic, potassium hydroxide liquid caustic.
本发明优点是：本发明提供一种2-氨基异丁醇的合成方法成方法，采用异丁烯为原料生产2-氨基丁醇成本较低，但由于要用到氯气、硫酸、液碱，必定会产生盐，不是一条清洁工艺，但它会打破垄断，给用户提供更廉价的2-氨基异丁醇。The advantage of the present invention is: the present invention provides a kind of synthetic method of 2-aminobutanol, adopts isobutene as raw material production 2-aminobutanol cost is lower, but because will use chlorine, sulfuric acid, liquid caustic soda, must Salt production is not a clean process, but it will break the monopoly and provide users with cheaper 2-aminoisobutanol.
具体实施方式detailed description
本发明包括以下步骤：The present invention comprises the following steps:
将1摩尔乙腈加入到5-15℃的1摩尔硫酸中混合均匀，再加入1摩尔甲基丙烯氯，反应2.5-3.5小时后倒入冰水中分层，在分出的有机层中加质量浓度10-50％的过量液碱,回流水解分层,分馏有机层得0.8摩尔的2-氨基异丁醇。Add 1 mole of acetonitrile to 1 mole of sulfuric acid at 5-15°C and mix evenly, then add 1 mole of methacrylic chloride, react for 2.5-3.5 hours, pour into ice water to separate layers, and add mass concentration to the separated organic layer 10-50% excess liquid caustic soda, reflux, hydrolysis and stratification, and fractional distillation of the organic layer to obtain 0.8 mole of 2-aminoisobutanol.
减压分馏收集, 在10mmHg压力下, 沸点为65-67℃馏份为2-氨基异丁醇，含量99.5% ，收率80%。Collected by fractional distillation under reduced pressure, under 10mmHg pressure , the fraction with a boiling point of 65-67°C is 2-aminoisobutanol with a content of 99.5% and a yield of 80%.
加入1摩尔甲基丙烯氯反应时，控制反应温度30℃以下。When adding 1 mole of methacrylic chloride for reaction, control the reaction temperature below 30°C.
液碱是氢氧化钠液碱、氢氧化钾液碱Liquid alkali is sodium hydroxide liquid alkali, potassium hydroxide liquid alkali
实例1Example 1
1摩尔硫酸降温到10℃加入1摩尔乙腈混合均匀，控温30℃以下，加入1摩尔甲基丙烯氯（反应放热），反应3小时后倒入冰水中分层，有机层加碱回流水解分层，分馏有机层得0.8摩尔2-氨基异丁醇（含量85% ）、二甲基环丙氮（含量13% ）、甲基丙烯氯（含量2% ），减压分馏收集b10 65～67℃得2-氨基异丁醇，含量99.5% ，收率80%（以消耗甲基丙烯氯计）。Cool down the temperature of 1 mole of sulfuric acid to 10°C, add 1 mole of acetonitrile and mix well, control the temperature below 30°C, add 1 mole of methacrylic chloride (reaction exotherm), react for 3 hours, pour into ice water to separate layers, add alkali to the organic layer and reflux for hydrolysis Layered, fractionated organic layer to get 0.8 moles of 2-aminoisobutanol (content 85%), dimethylcyclopropyl nitrogen (content 13%), methacrylic chloride (content 2%), collected by fractional distillation under reduced pressure b 10 65 2-Aminoisobutanol was obtained at ~67°C with a content of 99.5% and a yield of 80% (based on the consumption of methacrylic chloride).
实例2Example 2
按实例1，将甲基丙烯氯换成甲基丙烯醇醋酸酯按实例1实施，得2-氨基异丁醇0.84摩尔，含量99.7% ，收率84%（以消耗甲基丙烯醇醋酸酯计）。According to example 1, methacryl chloride is changed into methacryl acetate and implemented according to example 1, and 0.84 moles of 2-aminoisobutanol are obtained, with a content of 99.7%, and a yield of 84% (based on consumption of methacryl acetate) ).
实例3Example 3
将例1中乙腈换成氢氰酸，按例1实施，得2-氨基异丁醇0.85摩尔，含量99.2%，收率85%。In Example 1, acetonitrile was replaced with hydrocyanic acid, and implemented according to Example 1 to obtain 0.85 moles of 2-aminoisobutanol, with a content of 99.2%, and a yield of 85%.
实例4Example 4
将例1中甲基丙烯氯换成甲基丙烯醇醋酸酯，乙腈换成氢氰酸，按例1实施，得2-氨基异丁醇0.89摩尔，含量99.6% ，收率89% 。In Example 1, methacrylic chloride was replaced with methacryl acetate, and acetonitrile was replaced with hydrocyanic acid, and implemented according to Example 1, to obtain 0.89 moles of 2-aminoisobutanol, with a content of 99.6%, and a yield of 89%.
其反应化学方程式为：Its reaction chemical equation is:
R′通常为H或者CH3 ，即选用氢氰酸或乙腈。R' is usually H or CH 3 , that is, hydrocyanic acid or acetonitrile is selected.
R″通常为H或者CH3 ，即选用甲酸或醋酸。R" is usually H or CH 3 , that is, formic acid or acetic acid is selected.
Claims (4)
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| US3944617A (en) * | 1976-02-20 | 1976-03-16 | American Cyanamid Company | Synthesis of dl-2-amino-1-butanol |
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| US20060004045A1 (en) * | 2004-07-01 | 2006-01-05 | Li Chen | Thiazolinone unsubstituted quinolines |
| 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 |
-
2017
- 2017-02-03 CN CN201710062949.8A patent/CN106831451B/en active Active
Patent Citations (8)
| 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 |
| US20060004045A1 (en) * | 2004-07-01 | 2006-01-05 | Li Chen | Thiazolinone unsubstituted quinolines |
| 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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