GB688109A - Process for the manufacture of amino diols - Google Patents
Process for the manufacture of amino diolsInfo
- Publication number
- GB688109A GB688109A GB2666/52A GB266652A GB688109A GB 688109 A GB688109 A GB 688109A GB 2666/52 A GB2666/52 A GB 2666/52A GB 266652 A GB266652 A GB 266652A GB 688109 A GB688109 A GB 688109A
- Authority
- GB
- United Kingdom
- Prior art keywords
- diol
- nitro
- hydroxypropiophenone
- gives
- adjustment
- 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
- -1 amino diols Chemical class 0.000 title abstract 7
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 6
- 230000007062 hydrolysis Effects 0.000 abstract 6
- 238000006460 hydrolysis reaction Methods 0.000 abstract 6
- 238000010979 pH adjustment Methods 0.000 abstract 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 4
- 229910052782 aluminium Inorganic materials 0.000 abstract 4
- 239000004411 aluminium Substances 0.000 abstract 4
- 229910052757 nitrogen Inorganic materials 0.000 abstract 4
- 150000004703 alkoxides Chemical class 0.000 abstract 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 3
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 abstract 3
- 150000002009 diols Chemical class 0.000 abstract 3
- 239000012458 free base Substances 0.000 abstract 3
- 238000002955 isolation Methods 0.000 abstract 3
- 238000001953 recrystallisation Methods 0.000 abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 3
- KJJPLEZQSCZCKE-UHFFFAOYSA-N 2-aminopropane-1,3-diol Chemical compound OCC(N)CO KJJPLEZQSCZCKE-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 abstract 2
- 238000001640 fractional crystallisation Methods 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 abstract 1
- 238000005903 acid hydrolysis reaction Methods 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 229940088710 antibiotic agent Drugs 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- PIVQDUYOEIAFDM-UHFFFAOYSA-N n-[1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide Chemical class CC(=O)NC(CO)C(O)C1=CC=C([N+]([O-])=O)C=C1 PIVQDUYOEIAFDM-UHFFFAOYSA-N 0.000 abstract 1
- 238000006386 neutralization reaction Methods 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 150000003333 secondary alcohols Chemical class 0.000 abstract 1
- 230000007928 solubilization Effects 0.000 abstract 1
- 238000005063 solubilization Methods 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 150000003509 tertiary alcohols Chemical class 0.000 abstract 1
- WOZZOSDBXABUFO-UHFFFAOYSA-N tri(butan-2-yloxy)alumane Chemical compound [Al+3].CCC(C)[O-].CCC(C)[O-].CCC(C)[O-] WOZZOSDBXABUFO-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US271929XA | 1948-08-24 | 1948-08-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB688109A true GB688109A (en) | 1953-02-25 |
Family
ID=21836248
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2665/52A Expired GB688108A (en) | 1948-08-24 | 1949-02-15 | Process for the manufacture of ª‡-acylamido-ª‰-acyloxypropiophenones |
| GB4142/49A Expired GB688023A (en) | 1948-08-24 | 1949-02-15 | Improvements in and relating to the production of ketonic amino alcohol compounds |
| GB2666/52A Expired GB688109A (en) | 1948-08-24 | 1949-02-15 | Process for the manufacture of amino diols |
| GB26696/51A Expired GB688107A (en) | 1948-08-24 | 1949-02-15 | Improvement in methods for obtaining p-nitro-ª‡-amino-ª‰-hydroxypropiophenones |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2665/52A Expired GB688108A (en) | 1948-08-24 | 1949-02-15 | Process for the manufacture of ª‡-acylamido-ª‰-acyloxypropiophenones |
| GB4142/49A Expired GB688023A (en) | 1948-08-24 | 1949-02-15 | Improvements in and relating to the production of ketonic amino alcohol compounds |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB26696/51A Expired GB688107A (en) | 1948-08-24 | 1949-02-15 | Improvement in methods for obtaining p-nitro-ª‡-amino-ª‰-hydroxypropiophenones |
Country Status (6)
| Country | Link |
|---|---|
| CH (13) | CH285356A (cs) |
| CY (1) | CY104A (cs) |
| DE (4) | DE860067C (cs) |
| FR (1) | FR980961A (cs) |
| GB (4) | GB688108A (cs) |
| NL (2) | NL144893B (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2681364A (en) * | 1951-10-27 | 1954-06-15 | Parke Davis & Co | Process for the production of 1-p-nitrophenyl-2-acylamidopropane-1,3-diols |
-
0
- NL NL67749D patent/NL67749C/xx active
- NL NL666608250A patent/NL144893B/xx unknown
-
1949
- 1949-02-15 FR FR980961D patent/FR980961A/fr not_active Expired
- 1949-02-15 GB GB2665/52A patent/GB688108A/en not_active Expired
- 1949-02-15 GB GB4142/49A patent/GB688023A/en not_active Expired
- 1949-02-15 GB GB2666/52A patent/GB688109A/en not_active Expired
- 1949-02-15 GB GB26696/51A patent/GB688107A/en not_active Expired
- 1949-03-14 CH CH285356D patent/CH285356A/fr unknown
- 1949-03-14 CH CH282086D patent/CH282086A/fr unknown
- 1949-03-14 CH CH285357D patent/CH285357A/fr unknown
- 1949-03-14 CH CH285137D patent/CH285137A/fr unknown
- 1949-03-14 CH CH285361D patent/CH285361A/fr unknown
- 1949-03-14 CH CH285359D patent/CH285359A/fr unknown
- 1949-03-14 CH CH282087D patent/CH282087A/fr unknown
- 1949-03-14 CH CH285364D patent/CH285364A/fr unknown
- 1949-03-14 CH CH285358D patent/CH285358A/fr unknown
- 1949-03-14 CH CH285363D patent/CH285363A/fr unknown
- 1949-03-14 CH CH285360D patent/CH285360A/fr unknown
- 1949-03-14 CH CH271929D patent/CH271929A/fr unknown
- 1949-03-14 CH CH285362D patent/CH285362A/fr unknown
- 1949-10-25 DE DEP5178A patent/DE860067C/de not_active Expired
- 1949-10-25 DE DEP98A patent/DE855264C/de not_active Expired
- 1949-10-25 DE DE1949P0005179 patent/DE860068C/de not_active Expired
- 1949-10-25 DE DEP5177D patent/DE860066C/de not_active Expired
-
1953
- 1953-11-26 CY CY10556A patent/CY104A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE855264C (de) | 1952-11-10 |
| CY104A (en) | 1953-11-26 |
| CH271929A (fr) | 1950-11-30 |
| CH282087A (fr) | 1952-04-15 |
| CH285363A (fr) | 1952-08-31 |
| CH285361A (fr) | 1952-08-31 |
| CH285364A (fr) | 1952-08-31 |
| DE860068C (de) | 1952-12-18 |
| FR980961A (fr) | 1951-05-21 |
| CH285357A (fr) | 1952-08-31 |
| GB688023A (en) | 1953-02-25 |
| CH285358A (fr) | 1952-08-31 |
| CH285356A (fr) | 1952-08-31 |
| CH285137A (fr) | 1952-08-31 |
| CH285362A (fr) | 1952-08-31 |
| DE860066C (de) | 1952-12-18 |
| CH285360A (fr) | 1952-08-31 |
| NL144893B (nl) | |
| DE860067C (de) | 1952-12-18 |
| GB688107A (en) | 1953-02-25 |
| CH282086A (fr) | 1952-04-15 |
| CH285359A (fr) | 1952-08-31 |
| GB688108A (en) | 1953-02-25 |
| NL67749C (cs) |
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