US991721A - Process of producing beta-methyltetramethylene-diamin. - Google Patents
Process of producing beta-methyltetramethylene-diamin. Download PDFInfo
- Publication number
- US991721A US991721A US52954609A US1909529546A US991721A US 991721 A US991721 A US 991721A US 52954609 A US52954609 A US 52954609A US 1909529546 A US1909529546 A US 1909529546A US 991721 A US991721 A US 991721A
- Authority
- US
- United States
- Prior art keywords
- diamin
- methyltetramethylene
- producing beta
- beta
- germany
- 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 - Lifetime
Links
- 238000000034 method Methods 0.000 title description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- SYEOWUNSTUDKGM-YFKPBYRVSA-N 3-methyladipic acid Chemical compound OC(=O)C[C@@H](C)CCC(O)=O SYEOWUNSTUDKGM-YFKPBYRVSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- SYEOWUNSTUDKGM-UHFFFAOYSA-N beta-methyladipic acid Natural products OC(=O)CC(C)CCC(O)=O SYEOWUNSTUDKGM-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 239000003513 alkali Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- SURLGNKAQXKNSP-DBLYXWCISA-N chlorin Chemical compound C\1=C/2\N/C(=C\C3=N/C(=C\C=4NC(/C=C\5/C=CC/1=N/5)=CC=4)/C=C3)/CC\2 SURLGNKAQXKNSP-DBLYXWCISA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- -1 halogen salt Chemical class 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000000243 solution Substances 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
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/44—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers
- C07C209/50—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers by reduction of carboxylic acid amides
Definitions
- Our invention relates to a new and valuable process for producing beta-methyltetramethylene-dlamin.
- the new process consists in treating the diamid of beta-methyladipic acid in 10 parts of hot water is added. After heating for a short time to 70-80" C. the product of the reaction is neutralized with BrH and then concentrated by evaporation. Sodium bromid separates which is filtered Application filed November 28, 1909. Serial No. 529,546.
- the filtrate contains part of the BrX a and the bromohydrate of the base (NHi. GH -CH-CHz-CHFN H2) from which the latter base is set freeby treating the solution with caustic soda.
- the free base is isolated in the form of an oil, it is dried and finally purified by distillation.
- the process for producing beta-methyl tetramethylene-diamin which process con- .sists in treating the diamid of beta-methyladipic acid with an aqueous solution at halogen in caustic alkaline 'lyes and isolating .the free base by treating the halogen salt with alkali, substantially as described.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
- Adornments (AREA)
- Materials For Medical Uses (AREA)
Description
UNITED STATES PATENT OFFICE.
FRITZ HOEMANN AND CARL FARBENFABRIKEN VORM. CORPORATION OF GERMANY.
COUTELLE,
FRIEDR. BAYER & C
013 ELBERFELD, GERMANY, ASSIGNORS TO 0., OF ELBERIEELD, GERMANY, A
PROCESS OF PRODUCING BETA-METHYLTETRAMETHYLENE-DIAMIN.
No Drawing,
Specification of Letters Patent.
Patented May 9, 1 911.
. To all whom it may camera:
Be it known that-we, FRITZ HOFMANN and CARL ComELLE, doctors of philosophy, chemists, citizens of the German Empire, residing at Elberfeld, Germany, have invented new and useful Improvements in Processes for Producing Beta-h/Iethyltetramethylene-Diamin, of which the following is a specification.
Our invention relates to a new and valuable process for producing beta-methyltetramethylene-dlamin.
which is a valuable intermediate compound for the production of pharmaceutical compounds, dyestufl's, etc.
The new process consists in treating the diamid of beta-methyladipic acid in 10 parts of hot water is added. After heating for a short time to 70-80" C. the product of the reaction is neutralized with BrH and then concentrated by evaporation. Sodium bromid separates which is filtered Application filed November 28, 1909. Serial No. 529,546.
oil. The filtrate contains part of the BrX a and the bromohydrate of the base (NHi. GH -CH-CHz-CHFN H2) from which the latter base is set freeby treating the solution with caustic soda. The free base is isolated in the form of an oil, it is dried and finally purified by distillation.
The "formation ofthe product takes probably place accordingto the following formula:
The process is carried out in an analogous manner on using instead of bronnn the equivalent amount of chlorin. In this case the product of'the reaction is neutralized with hydrochloric acid.
The process for producing beta-methyl tetramethylene-diamin, which process con- .sists in treating the diamid of beta-methyladipic acid with an aqueous solution at halogen in caustic alkaline 'lyes and isolating .the free base by treating the halogen salt with alkali, substantially as described.
set our hand in the presence of two subscribmg Witnesses.
FRITZ HOFMANN. 1 5. CARL COUTELLE. a 3.
Witnesses -O'r'ro Keno,
CHAS. J. WRIGHT.
In testimony whereof we have hereunto- (so I
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US52954609A US991721A (en) | 1909-11-23 | 1909-11-23 | Process of producing beta-methyltetramethylene-diamin. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US52954609A US991721A (en) | 1909-11-23 | 1909-11-23 | Process of producing beta-methyltetramethylene-diamin. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US991721A true US991721A (en) | 1911-05-09 |
Family
ID=3060056
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US52954609A Expired - Lifetime US991721A (en) | 1909-11-23 | 1909-11-23 | Process of producing beta-methyltetramethylene-diamin. |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US991721A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4198348A (en) * | 1977-06-14 | 1980-04-15 | Snia Viscosa Societa Nazionale Industria Applicazioni Viscosa S.P.A. | Process for the preparation of amines |
| US5410082A (en) * | 1993-05-11 | 1995-04-25 | Pfirmann; Ralf | Process for preparing amines |
-
1909
- 1909-11-23 US US52954609A patent/US991721A/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4198348A (en) * | 1977-06-14 | 1980-04-15 | Snia Viscosa Societa Nazionale Industria Applicazioni Viscosa S.P.A. | Process for the preparation of amines |
| US5410082A (en) * | 1993-05-11 | 1995-04-25 | Pfirmann; Ralf | Process for preparing amines |
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