GB734050A - Process for the production of amino alcohols - Google Patents
Process for the production of amino alcoholsInfo
- Publication number
- GB734050A GB734050A GB8848/53A GB884853A GB734050A GB 734050 A GB734050 A GB 734050A GB 8848/53 A GB8848/53 A GB 8848/53A GB 884853 A GB884853 A GB 884853A GB 734050 A GB734050 A GB 734050A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amino
- water
- residue
- chlorinated
- hydrolysed
- 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
Links
- 150000001414 amino alcohols Chemical class 0.000 title abstract 4
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 5
- 239000000047 product Substances 0.000 abstract 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- 238000004821 distillation Methods 0.000 abstract 3
- LQGKDMHENBFVRC-UHFFFAOYSA-N 5-aminopentan-1-ol Chemical compound NCCCCCO LQGKDMHENBFVRC-UHFFFAOYSA-N 0.000 abstract 2
- -1 alkyl amine hydrochloride Chemical class 0.000 abstract 2
- 239000002585 base Substances 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 abstract 2
- 235000011121 sodium hydroxide Nutrition 0.000 abstract 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract 2
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 abstract 1
- BLFRQYKZFKYQLO-UHFFFAOYSA-N 4-aminobutan-1-ol Chemical compound NCCCCO BLFRQYKZFKYQLO-UHFFFAOYSA-N 0.000 abstract 1
- MXMGNWPTOBCQIL-UHFFFAOYSA-N 5-chloropentan-1-amine;hydrochloride Chemical compound Cl.NCCCCCCl MXMGNWPTOBCQIL-UHFFFAOYSA-N 0.000 abstract 1
- SUTWPJHCRAITLU-UHFFFAOYSA-N 6-aminohexan-1-ol Chemical compound NCCCCCCO SUTWPJHCRAITLU-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 229920000180 alkyd Polymers 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 abstract 1
- 239000012458 free base Substances 0.000 abstract 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000000468 ketone group Chemical group 0.000 abstract 1
- 238000006386 neutralization reaction Methods 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- 235000011118 potassium hydroxide Nutrition 0.000 abstract 1
- 230000035484 reaction time Effects 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Amino alcohols are prepared by hydrolysing a chlorinated alkyl amine hydrochloride by heating in water whilst maintaining an acid reaction. The hydrolysis may be effected by heating under reflux or under pressure with 5 to 100 times the quantity of water. Reaction temperature may lie between 50 DEG and 200 DEG C. and reaction times of 1 to 20 hours are required. The free amino alcohols are recovered by addition of a strong base such as caustic soda, caustic potash or lime water followed by distillation which may be carried out under vacuum, or the hydrochloric acid formed may be distilled off before adding the strong base. Small amounts of alkenyl amines and amines containing two hydroxyl groups or a keto group, are formed as by-products. The amino alcohols may be used for the production of alkyd resins or other polymerization products. In examples: (1) n-butylamine was neutralized with hydrochloric acid and chlorinated whilst being irradiated with ultra-violet light. The hydrochloric acid formed was distilled off and the residue hydrolysed with water at 150 DEG C. The free base was obtained by addition of caustic soda and 4-amino-butanol was recovered by distillation; (2) n-pentylamine in carbon tetrachloride solution was neutralized with hydrogen chloride, then chlorinated while using actinic light. The solvent was distilled off and the residue hydrolysed and worked up as in (1). The product was 5-amino-pentanol; (3) n-hexylamine was converted to hydrochloride and chlorinated as in (2) and the residue refluxed with water. The product after neutralization and distillation was 6-amino-hexanol; (4) 5-chlor - 1 - amino - pentane hydrochloride was hydrolysed with water at 150 DEG C. The residue was worked up as in (1) and the product was 5-amino-pentanol.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE313769X | 1952-04-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB734050A true GB734050A (en) | 1955-07-20 |
Family
ID=6142330
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8848/53A Expired GB734050A (en) | 1952-04-04 | 1953-03-31 | Process for the production of amino alcohols |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH313769A (en) |
| FR (1) | FR1074250A (en) |
| GB (1) | GB734050A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1183909B (en) * | 1962-02-03 | 1964-12-23 | Basf Ag | Process for the preparation of 1,6-hexanolamine |
-
1953
- 1953-03-31 GB GB8848/53A patent/GB734050A/en not_active Expired
- 1953-04-01 CH CH313769D patent/CH313769A/en unknown
- 1953-04-02 FR FR1074250D patent/FR1074250A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1183909B (en) * | 1962-02-03 | 1964-12-23 | Basf Ag | Process for the preparation of 1,6-hexanolamine |
Also Published As
| Publication number | Publication date |
|---|---|
| CH313769A (en) | 1956-05-15 |
| FR1074250A (en) | 1954-10-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3340299A (en) | Tetrasubstituted ethylene diamines | |
| SE7903907L (en) | PROCEDURE FOR PREPARING ALFA, BETA-PMETTADE, N-SUBSTITUTED CARBOXYLIC ACID AMIDES | |
| GB734050A (en) | Process for the production of amino alcohols | |
| US2765320A (en) | Preparation of 2, 3-dimethylindole | |
| US2203009A (en) | Manufacture of nu-tertiary amino acyclic carboxylic acids and their salts | |
| US2541747A (en) | Production of hydroxyl compounds by hydrolysis of tetrahydropyryl ethers | |
| US2773097A (en) | Alkali splitting of secondary and tertiary formamides | |
| GB675665A (en) | Improvements in and relating to the production of polymeric compounds | |
| GB655864A (en) | Improvements in and relating to the condensation of alcohols | |
| US2457226A (en) | Preparation of choline chloride | |
| US2413968A (en) | Process for manufacture of nu-alkyl glycines | |
| GB727031A (en) | Process for the production of dibutolactam | |
| GB723481A (en) | Improvements in polyvinyl resins | |
| GB821388A (en) | Method of preparing alkali metal hypophosphites | |
| US3652684A (en) | Preparation of alcohols | |
| GB802079A (en) | Benzthiazyl sulphenamides and their use as vulcanization accelerators | |
| JPS54122695A (en) | Recovering method for unreacted raw materials from reaction mother liquor of anhydrous hydrosulfite | |
| US3163678A (en) | Process for the production of monochloracetaldehyde | |
| GB753489A (en) | Process for the preparation of tetraethylenepentamine | |
| GB746413A (en) | Method of recovering para-nitrochlorobenzene | |
| US3042704A (en) | Methyl borate process | |
| GB601816A (en) | Process for making an alkali metal salt of an amino carboxylic acid | |
| DE953170C (en) | Process for the degradation of quaternary aromatic ammonium compounds to tertiary aromatic amines | |
| GB367797A (en) | Process for the manufacture of 1-phenyl-2, 3-dimethyl-5-pyrazolone | |
| GB977044A (en) | New compounds and process for preparing them |