DE591269C - Verfahren zur Darstellung cyclischer ª‡-Cyanketimide und cyclischer ª‡-Cyanketone - Google Patents
Verfahren zur Darstellung cyclischer ª‡-Cyanketimide und cyclischer ª‡-CyanketoneInfo
- Publication number
- DE591269C DE591269C DESCH98619D DESC098619D DE591269C DE 591269 C DE591269 C DE 591269C DE SCH98619 D DESCH98619 D DE SCH98619D DE SC098619 D DESC098619 D DE SC098619D DE 591269 C DE591269 C DE 591269C
- Authority
- DE
- Germany
- Prior art keywords
- cyclic
- cyanketimides
- acid
- solution
- preparation
- 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
- 125000004122 cyclic group Chemical group 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 150000002825 nitriles Chemical class 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 238000010790 dilution Methods 0.000 claims description 3
- 239000012895 dilution Substances 0.000 claims description 3
- 229910052749 magnesium Inorganic materials 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 17
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 238000009835 boiling Methods 0.000 description 6
- BDJRBEYXGGNYIS-UHFFFAOYSA-N Nonanedioid acid Natural products OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 4
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- -1 cyclic keto acid esters Chemical class 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- GKVBRMPYYMAKAR-UHFFFAOYSA-N 2-oxocyclopentadecane-1-carbonitrile Chemical compound O=C1CCCCCCCCCCCCCC1C#N GKVBRMPYYMAKAR-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- OSOIQJGOYGSIMF-UHFFFAOYSA-N cyclopentadecanone Chemical compound O=C1CCCCCCCCCCCCCC1 OSOIQJGOYGSIMF-UHFFFAOYSA-N 0.000 description 2
- HSUGRBWQSSZJOP-RTWAWAEBSA-N diltiazem Chemical compound C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CCN(C)C)C2=CC=CC=C2S1 HSUGRBWQSSZJOP-RTWAWAEBSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- BTNXBLUGMAMSSH-UHFFFAOYSA-N octanedinitrile Chemical compound N#CCCCCCCC#N BTNXBLUGMAMSSH-UHFFFAOYSA-N 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- UDNSORQCHREQLL-UHFFFAOYSA-N 2,9-dioxocyclohexadecane-1,8-dicarbonitrile Chemical compound C(#N)C1C(CCCCCCCC(C(CCCCC1)=O)C#N)=O UDNSORQCHREQLL-UHFFFAOYSA-N 0.000 description 1
- HHLZCLDCRQPOCR-UHFFFAOYSA-N 2-oxocyclooctane-1-carbonitrile Chemical compound O=C1CCCCCCC1C#N HHLZCLDCRQPOCR-UHFFFAOYSA-N 0.000 description 1
- QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- WMNJKOBFFGOKQD-UHFFFAOYSA-N cyclohexadecane-1,2-dione Chemical compound O=C1CCCCCCCCCCCCCCC1=O WMNJKOBFFGOKQD-UHFFFAOYSA-N 0.000 description 1
- IIRFCWANHMSDCG-UHFFFAOYSA-N cyclooctanone Chemical compound O=C1CCCCCCC1 IIRFCWANHMSDCG-UHFFFAOYSA-N 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- UZBQIPPOMKBLAS-UHFFFAOYSA-N diethylazanide Chemical compound CC[N-]CC UZBQIPPOMKBLAS-UHFFFAOYSA-N 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- AHNJTQYTRPXLLG-UHFFFAOYSA-N lithium;diethylazanide Chemical compound [Li+].CC[N-]CC AHNJTQYTRPXLLG-UHFFFAOYSA-N 0.000 description 1
- 229910001623 magnesium bromide Inorganic materials 0.000 description 1
- HEVSIKNIWJEAAA-UHFFFAOYSA-M magnesium;diethylazanide;bromide Chemical compound [Br-].CCN([Mg+])CC HEVSIKNIWJEAAA-UHFFFAOYSA-M 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- MHODTZQUOCJRAM-UHFFFAOYSA-N n-ethylaniline;lithium Chemical group [Li].CCNC1=CC=CC=C1 MHODTZQUOCJRAM-UHFFFAOYSA-N 0.000 description 1
- XPVYVHOOOGLRDU-UHFFFAOYSA-N n-methylaniline;sodium Chemical compound [Na].CNC1=CC=CC=C1 XPVYVHOOOGLRDU-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 150000007659 semicarbazones Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/42—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrolysis
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DESCH98619D DE591269C (de) | 1932-08-16 | 1932-08-16 | Verfahren zur Darstellung cyclischer ª‡-Cyanketimide und cyclischer ª‡-Cyanketone |
| NL66043A NL35493C (enrdf_load_stackoverflow) | 1932-08-16 | 1933-07-18 | |
| GB21991/33A GB415259A (en) | 1932-08-16 | 1933-08-04 | Process for the manufacture of cyclic ª‡-cyanketimides and cyclic ª‡-cyanketones |
| FR759436D FR759436A (fr) | 1932-08-16 | 1933-08-10 | Procédé de préparation d'alpha-cyanocétimides cycliques et d'alpha-cyanocétonescycliques |
| DESCH102689D DE620904C (de) | 1932-08-16 | 1933-11-19 | Verfahren zur Darstellung cyclischer ª‡-Cyanketimide und cyclischer ª‡-Cyanketone |
| NL71461A NL39070C (enrdf_load_stackoverflow) | 1932-08-16 | 1934-11-19 | |
| FR46401D FR46401E (fr) | 1932-08-16 | 1934-11-19 | Procédé de préparation d'alpha-cyanocétimides cycliques et d'alpha-cyanocétonescycliques |
| GB33271/34A GB438291A (en) | 1932-08-16 | 1934-11-19 | Process for the manufacture of cyclic ª‡-cyanketimides and cyclic cyanketones |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DESCH98619D DE591269C (de) | 1932-08-16 | 1932-08-16 | Verfahren zur Darstellung cyclischer ª‡-Cyanketimide und cyclischer ª‡-Cyanketone |
| DESCH102689D DE620904C (de) | 1932-08-16 | 1933-11-19 | Verfahren zur Darstellung cyclischer ª‡-Cyanketimide und cyclischer ª‡-Cyanketone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE591269C true DE591269C (de) | 1934-01-19 |
Family
ID=25932790
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DESCH98619D Expired DE591269C (de) | 1932-08-16 | 1932-08-16 | Verfahren zur Darstellung cyclischer ª‡-Cyanketimide und cyclischer ª‡-Cyanketone |
| DESCH102689D Expired DE620904C (de) | 1932-08-16 | 1933-11-19 | Verfahren zur Darstellung cyclischer ª‡-Cyanketimide und cyclischer ª‡-Cyanketone |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DESCH102689D Expired DE620904C (de) | 1932-08-16 | 1933-11-19 | Verfahren zur Darstellung cyclischer ª‡-Cyanketimide und cyclischer ª‡-Cyanketone |
Country Status (4)
| Country | Link |
|---|---|
| DE (2) | DE591269C (enrdf_load_stackoverflow) |
| FR (2) | FR759436A (enrdf_load_stackoverflow) |
| GB (2) | GB415259A (enrdf_load_stackoverflow) |
| NL (2) | NL35493C (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0632004A1 (de) * | 1993-06-30 | 1995-01-04 | BASF Aktiengesellschaft | Verfahren zur Herstellung von cyclischen Ketonen |
| CN109071421A (zh) * | 2016-05-02 | 2018-12-21 | 英威达纺织（英国）有限公司 | 减少二腈流中的cpi的方法 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115650880B (zh) * | 2022-11-03 | 2024-08-20 | 万华化学（宁波）有限公司 | 一种过保质期mdi的回收处理方法及由其制备碳化二亚胺改性异氰酸酯的方法和产品 |
-
1932
- 1932-08-16 DE DESCH98619D patent/DE591269C/de not_active Expired
-
1933
- 1933-07-18 NL NL66043A patent/NL35493C/xx active
- 1933-08-04 GB GB21991/33A patent/GB415259A/en not_active Expired
- 1933-08-10 FR FR759436D patent/FR759436A/fr not_active Expired
- 1933-11-19 DE DESCH102689D patent/DE620904C/de not_active Expired
-
1934
- 1934-11-19 NL NL71461A patent/NL39070C/xx active
- 1934-11-19 GB GB33271/34A patent/GB438291A/en not_active Expired
- 1934-11-19 FR FR46401D patent/FR46401E/fr not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0632004A1 (de) * | 1993-06-30 | 1995-01-04 | BASF Aktiengesellschaft | Verfahren zur Herstellung von cyclischen Ketonen |
| CN109071421A (zh) * | 2016-05-02 | 2018-12-21 | 英威达纺织（英国）有限公司 | 减少二腈流中的cpi的方法 |
| US11028045B2 (en) | 2016-05-02 | 2021-06-08 | Inv Nylon Chemicals Americas, Llc | Process for reducing CPI in a dinitrile stream |
Also Published As
| Publication number | Publication date |
|---|---|
| GB415259A (en) | 1934-08-23 |
| DE620904C (de) | 1935-10-30 |
| FR759436A (fr) | 1934-02-01 |
| NL39070C (enrdf_load_stackoverflow) | 1936-09-15 |
| FR46401E (fr) | 1936-06-03 |
| NL35493C (enrdf_load_stackoverflow) | 1935-05-15 |
| GB438291A (en) | 1935-11-14 |
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