CH641157A5 - Procede de preparation de l'hexamethylene-bis-dicyanodiamide. - Google Patents
Procede de preparation de l'hexamethylene-bis-dicyanodiamide. Download PDFInfo
- Publication number
- CH641157A5 CH641157A5 CH779379A CH779379A CH641157A5 CH 641157 A5 CH641157 A5 CH 641157A5 CH 779379 A CH779379 A CH 779379A CH 779379 A CH779379 A CH 779379A CH 641157 A5 CH641157 A5 CH 641157A5
- Authority
- CH
- Switzerland
- Prior art keywords
- reaction
- compound
- yield
- cyano
- crystals
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 25
- 238000002360 preparation method Methods 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 27
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 21
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 claims description 10
- 239000001099 ammonium carbonate Substances 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 229910021529 ammonia Inorganic materials 0.000 claims description 7
- 229910000013 Ammonium bicarbonate Inorganic materials 0.000 claims description 5
- 235000012538 ammonium bicarbonate Nutrition 0.000 claims description 5
- 235000012501 ammonium carbonate Nutrition 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 229910052717 sulfur Chemical group 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 description 25
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 18
- 239000013078 crystal Substances 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000007858 starting material Substances 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- JKZWPSHYNAEPAA-UHFFFAOYSA-N cyanocarbamic acid Chemical compound OC(=O)NC#N JKZWPSHYNAEPAA-UHFFFAOYSA-N 0.000 description 8
- QWJNFFYFEKXZBF-UHFFFAOYSA-N cyanocyanamide Chemical compound N#CNC#N QWJNFFYFEKXZBF-UHFFFAOYSA-N 0.000 description 8
- 159000000011 group IA salts Chemical class 0.000 description 8
- WJLVQTJZDCGNJN-UHFFFAOYSA-N Chlorhexidine hydrochloride Chemical compound Cl.Cl.C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 WJLVQTJZDCGNJN-UHFFFAOYSA-N 0.000 description 7
- 239000004202 carbamide Substances 0.000 description 7
- 229960004504 chlorhexidine hydrochloride Drugs 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 235000011114 ammonium hydroxide Nutrition 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- GHXZTYHSJHQHIJ-UHFFFAOYSA-N Chlorhexidine Chemical compound C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 GHXZTYHSJHQHIJ-UHFFFAOYSA-N 0.000 description 5
- 229960003260 chlorhexidine Drugs 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000002329 infrared spectrum Methods 0.000 description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000011707 mineral Substances 0.000 description 5
- 239000013074 reference sample Substances 0.000 description 5
- -1 sodium cyanamide Chemical compound 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 4
- OASACOUTJYOHCV-UHFFFAOYSA-N CCN(C(O)=N)OC#N Chemical compound CCN(C(O)=N)OC#N OASACOUTJYOHCV-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- ISJBQSJDQZLCSF-UHFFFAOYSA-N (4-chlorophenyl)azanium;chloride Chemical compound [Cl-].[NH3+]C1=CC=C(Cl)C=C1 ISJBQSJDQZLCSF-UHFFFAOYSA-N 0.000 description 2
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical class NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 2
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000003708 ampul Substances 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000004599 antimicrobial Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- PHKAAMFBQKLUDI-UHFFFAOYSA-N carbonodithioic S,S-acid cyanamide Chemical compound NC#N.SC(S)=O PHKAAMFBQKLUDI-UHFFFAOYSA-N 0.000 description 1
- JWEKFMCYIRVOQZ-UHFFFAOYSA-N cyanamide;sodium Chemical compound [Na].NC#N JWEKFMCYIRVOQZ-UHFFFAOYSA-N 0.000 description 1
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 1
- LIFQNDHZCABWSO-UHFFFAOYSA-N cyanomethanedithioic acid Chemical compound SC(=S)C#N LIFQNDHZCABWSO-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- RRLWYLINGKISHN-UHFFFAOYSA-N ethoxymethanol Chemical compound CCOCO RRLWYLINGKISHN-UHFFFAOYSA-N 0.000 description 1
- WXWBWFZUYBCWOR-UHFFFAOYSA-N ethyl n'-cyanocarbamimidothioate Chemical compound CCSC(=N)NC#N WXWBWFZUYBCWOR-UHFFFAOYSA-N 0.000 description 1
- JIAFGCKUXLMTJH-UHFFFAOYSA-N hexane-1,6-diamine;hydrate Chemical compound O.NCCCCCCN JIAFGCKUXLMTJH-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- XTLAGIJVEHOCLK-UHFFFAOYSA-N methyl n'-cyanocarbamimidothioate Chemical compound CSC(N)=NC#N XTLAGIJVEHOCLK-UHFFFAOYSA-N 0.000 description 1
- RARSHUDCJQSEFJ-UHFFFAOYSA-N p-Hydroxypropiophenone Chemical compound CCC(=O)C1=CC=C(O)C=C1 RARSHUDCJQSEFJ-UHFFFAOYSA-N 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 239000012991 xanthate Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/28—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to cyano groups, e.g. cyanoguanidines, dicyandiamides
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 |
|---|---|---|---|
| JP10549078A JPS5533416A (en) | 1978-08-31 | 1978-08-31 | Production of hexamethyene bis-dicyandiamide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH641157A5 true CH641157A5 (fr) | 1984-02-15 |
Family
ID=14409028
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH779379A CH641157A5 (fr) | 1978-08-31 | 1979-08-28 | Procede de preparation de l'hexamethylene-bis-dicyanodiamide. |
Country Status (6)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3729530A1 (de) * | 1987-09-04 | 1989-03-16 | Degussa | Verfahren zur herstellung von 1,6-di(n(pfeil hoch)3(pfeil hoch)-cyano-n(pfeil hoch)1(pfeil hoch)-guanidino)hexan |
| EP2895457B1 (en) | 2012-09-17 | 2020-05-20 | Nektar Therapeutics | Oligomer-containing benzamide-based compounds |
| CN111302976A (zh) * | 2020-04-14 | 2020-06-19 | 苏州敬业医药化工有限公司 | 一种洗必泰碱的制备方法 |
| CN118126450B (zh) * | 2024-03-18 | 2024-09-17 | 威海喜盈门乳品有限公司 | 一种食品用改性聚丙烯复合包装材料的制备方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB702268A (en) * | 1949-08-22 | 1954-01-13 | Francis Leslie Rose | Polymeric diguanides |
| US2697727A (en) * | 1953-04-28 | 1954-12-21 | American Cyanamid Co | Method of preparing s-alkyl cyanopseudothioureas |
| DE1568581C3 (de) * | 1966-09-08 | 1974-08-15 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung substituierter Cyano-Guanidine |
| US3597466A (en) * | 1968-11-21 | 1971-08-03 | Olin Mathieson | Preparation of aromatic isocyanates |
| US4158013A (en) * | 1977-06-03 | 1979-06-12 | Bristol-Myers Company | N-Cyano-N'-alkynyl-N"-2-mercaptoethylguanidines |
| US4163056A (en) * | 1977-09-29 | 1979-07-31 | Ciba-Geigy Corporation | Pesticidal triazapentadienes |
| US4157340A (en) * | 1978-06-27 | 1979-06-05 | Bristol-Meyers Company | N,N'-[Bis(N-cyanoguanyl)]cystamine derivatives |
-
1978
- 1978-08-31 JP JP10549078A patent/JPS5533416A/ja active Granted
-
1979
- 1979-08-07 US US06/065,144 patent/US4250109A/en not_active Expired - Lifetime
- 1979-08-13 GB GB7928127A patent/GB2028815B/en not_active Expired
- 1979-08-14 DE DE19792932951 patent/DE2932951A1/de not_active Withdrawn
- 1979-08-28 CH CH779379A patent/CH641157A5/fr not_active IP Right Cessation
- 1979-08-30 FR FR7921749A patent/FR2434801A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| GB2028815B (en) | 1983-04-27 |
| JPS6125026B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1986-06-13 |
| US4250109A (en) | 1981-02-10 |
| FR2434801A1 (fr) | 1980-03-28 |
| FR2434801B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-07-20 |
| DE2932951A1 (de) | 1980-03-20 |
| JPS5533416A (en) | 1980-03-08 |
| GB2028815A (en) | 1980-03-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| BE1006426A6 (fr) | Procede de preparation de la n-methyl-3-phenyl-3-[4-(trifluoromethyl)-phenoxy]-propylamine et de ses sels d'addition d'acide. | |
| FR2567124A1 (fr) | Nouvelle forme d cristalline, stable, anhydre du chlorhydrate de prazosine et nouveau procede pour la preparation de cette forme d cristalline | |
| FR2509724A1 (fr) | Nouvelles guanidines a fort encombrement sterique et procedes pour leur preparation | |
| EP0110781A1 (fr) | (Amino-2 éthyl)-6 benzoxazolinones substituées, leur préparation et une composition pharmaceutique les contenant | |
| JP2992389B2 (ja) | 光学活性１−アリール−アルキルアミン類のラセミ化方法 | |
| CH479552A (fr) | Procédé pour la préparation de cétimines | |
| CH641157A5 (fr) | Procede de preparation de l'hexamethylene-bis-dicyanodiamide. | |
| CH639944A5 (fr) | 2-(4-chlorophenyl)isovalerate d'alpha-cyano-3-phenoxybenzyle, procede pour sa preparation, et composition insecticide et acaricide le contenant. | |
| KR101126948B1 (ko) | 비칼루타미드의 제조 방법 및 그 중간체의 정제 방법 | |
| FR2601005A1 (fr) | Procede de preparation d'esters alkyliques de l'acide cyano-2 tetrachlorobenzoique | |
| FR2793490A1 (fr) | Procede de preparation du (1r,2s,4r)-(-)-2-[(2'-{n,n- dimethylamino}-ethoxy)]-2-[phenyl]-1,7,7-tri-[methyl]- bicyclo[2.2.1]-heptane et ses sels d'addition d'acide pharmaceutiquement acceptables | |
| EP0153261B1 (fr) | Esters de la famille de la N-phosphonométhylglycine et leur utilisation pour la préparation d'herbicides connus | |
| FR2510991A1 (fr) | Procede pour la preparation de methacrylamides et d'acrylamides n-substitues | |
| FR2499986A1 (fr) | Procede de production du peroxyde de dicumyle | |
| EP0158556A1 (fr) | Procédé de préparation d'acides hydroxyalkylaminoacétiques | |
| EP0221815B1 (fr) | Procédé pour la fabrication d'acides alkanoiques | |
| FR2551747A1 (fr) | Procede de production d'aminobenzylamines | |
| JPS63290838A (ja) | ベンジルオキシフェノン類の製造法 | |
| JPH09143128A (ja) | 光学活性１−フェニルエチルアミンの製造法 | |
| FR2632303A1 (fr) | Procede de preparation du 3-aminocrotonate de methyle | |
| BE897708A (fr) | Procede de preparation de 2-benzothiazole-sulfenamides a empechement sterique | |
| EP0627402B1 (fr) | Procédé d'obtention d'acides hydroxyphénylacétiques | |
| CH487178A (fr) | Procédé de préparation de dérivés de la phénothiazine | |
| FR2652082A1 (fr) | Procede de preparation de l'acide-1 cyclopropanecarboxylique ou d'un de ses sels, produits de depart et leurs procedes de preparation. | |
| FR2725201A1 (fr) | Procede de preparation de derives du nitrobenzene |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |