NO764110L - - Google Patents
Info
- Publication number
- NO764110L NO764110L NO764110A NO764110A NO764110L NO 764110 L NO764110 L NO 764110L NO 764110 A NO764110 A NO 764110A NO 764110 A NO764110 A NO 764110A NO 764110 L NO764110 L NO 764110L
- Authority
- NO
- Norway
- Prior art keywords
- aromatic
- stated
- reaction
- carried out
- amine
- Prior art date
Links
- -1 aromatic urethanes Chemical class 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- PBBJBFOOHLPWOV-UHFFFAOYSA-N 1,1'-biphenyl;carbonic acid Chemical compound OC(O)=O.C1=CC=CC=C1C1=CC=CC=C1 PBBJBFOOHLPWOV-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- TXSLQCZKCZCCAS-UHFFFAOYSA-N ethyl n-(4-chlorophenyl)-n-methylcarbamate Chemical compound CCOC(=O)N(C)C1=CC=C(Cl)C=C1 TXSLQCZKCZCCAS-UHFFFAOYSA-N 0.000 description 1
- ZHMIEJHAMNTUBZ-UHFFFAOYSA-N ethyl n-phenyl-n-propylcarbamate Chemical compound CCOC(=O)N(CCC)C1=CC=CC=C1 ZHMIEJHAMNTUBZ-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/40—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings
- C07C271/42—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/44—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Foreliggende oppfinnelse vedrører en fremgangsmåte for fremstilling av aromatiske uretaner med den generelle formel
hvori Ar er et radikal inneholdende minst en aromatisk gruppe av typen fenyl, naftyl, eventuelt substituert med alkyl,. alkoksy,
aryl, aryloksy, halogener eller dialkylamino, og R og R' er like eller forskjellige og er alkylradikaler eller hydrogenatomer.
Det er kjent å syntetisere angjeldende forbindelser ved å gå ut
fra deres respektive fenoler og alkylisocyanater, eller også fra arylklorformater og aminer, som kjent fra f.eks. italiensk patent-skrift 965.506-
Disse tidligere metoder medfører-i tillegg til at de er meget omstendelige betraktelige usikkerhetsmomenter med hensyn til giftigheten av de2eaksjonskomponenter som anvendes.
Det er likeledes kjent at de angjeldende produkter finner hyppig anvendelse innenfor industrien som insektisider, hvorav noen er spesielt interessante på grunn av deres lave giftighetsindeks.
Det er nå funnet at det er mulig å oppnå slike forbindelser ved
å omsette aromatiske karbonater med alifatiske aminer, eventuelt i nærvær av organiske løsningsmidler. Reaksjonen finner sted spontant og hurtig, endog under meget milde betingelser inntil karbonatet er blitt fullstendig omdannet, ved anvendelse av støkiometrisd mengder av aminet.
Et overskudd av aminet, eller en for høy temperatur (over 100°C) kan føre til dannelse av en viss mengde urea som biprodukt.
De følgende eksempler skal illustrere oppfinnelsen.
EKSEMPEL 1
107 g bifenylkarbonat og 150 ml benzen ble innført i en 500 ml kolbe. 30 g rent propylamin ble gradvis innført i blandingen idet temperaturen ble holdt i området rundt 40°C.
Det ble oppnådd 86g fenyl-propyluretan med et utbytte på omtrent 95% av det teoretiske.
EKSEMPEL 2
160 g binaftylkarbonat og 150 ml dioksan ble innført i en 500 ml kolbe.
16 g rent gassformet metylamin ble boblet gjennom blandingen i
1 time idet temperaturen ble holdt ved 20°C.
Det ble oppnådd 93 g alfa-naftyl-alfametyl uretan.
EKSEMPEL 3
140 g 4,4'-dikloro-bifenyl-karbonat og 150 ml CC14ble innført i en 50 0 ml kolbe. 16 g rent metylamin ble tilsatt mens temperaturen ble holdt ved 30°C.
Det ble oppnådd 85 g 4-kloro-fenyl-N-metyl uretan.
Claims (3)
1. Fremgangsmåte for fremstilling av aromatiske uretaner med den generelle formel
hvori Ar er et radikal inneholdende minst en aromatisk gruppe,
R og R' er . like eller forskjellige og er hydrogenatomer eller alkylradikaler, karakterisert ved at aromatiske karbonater omsettes med alifatiske aminer.
r
2. Fremgangsmåte som angitt i krav 1, karakterisert ved at reaksjonen gjennomføres ved en temperatur under.100°C.
3. Fremgangsmåte som angitt i krav 1 og/eller 2, karakterisert ved at reaksjonen gjennomføres ved å gå ut fra en støkiometrisk mengde av aminet.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT29960/75A IT1051034B (it) | 1975-12-03 | 1975-12-03 | Procedimento per la preparazione di uretani aromatici |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO764110L true NO764110L (no) | 1977-06-06 |
Family
ID=11228760
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO764110A NO764110L (no) | 1975-12-03 | 1976-12-01 |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4097676A (no) |
| JP (1) | JPS5271443A (no) |
| AU (1) | AU509444B2 (no) |
| BE (1) | BE849070A (no) |
| BR (1) | BR7608198A (no) |
| CA (1) | CA1088093A (no) |
| DD (1) | DD127477A5 (no) |
| DE (1) | DE2654939A1 (no) |
| DK (1) | DK538676A (no) |
| FR (1) | FR2333779A1 (no) |
| GB (1) | GB1532028A (no) |
| IE (1) | IE44472B1 (no) |
| IT (1) | IT1051034B (no) |
| LU (1) | LU76300A1 (no) |
| MW (1) | MW4776A1 (no) |
| NL (1) | NL7613526A (no) |
| NO (1) | NO764110L (no) |
| PT (1) | PT65921B (no) |
| SE (1) | SE433610B (no) |
| YU (1) | YU290376A (no) |
| ZA (1) | ZA766992B (no) |
| ZM (1) | ZM13976A1 (no) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4258200A (en) * | 1980-03-11 | 1981-03-24 | Air Products And Chemicals, Inc. | Production of carboxylic acid amides and carbamates using cobalt catalysts |
| JPS60215660A (ja) * | 1984-04-11 | 1985-10-29 | Nippon Tokushu Noyaku Seizo Kk | ビフエニリルスルホニルウレア誘導体の製法、その中間体及び該中間体の製法 |
| JPS61134367A (ja) * | 1984-12-06 | 1986-06-21 | Nippon Tokushu Noyaku Seizo Kk | フエニルｎ−（２−ビフエニリルスルホニル）カ−バメ−トの改良製造方法 |
| IT1183332B (it) * | 1985-02-08 | 1987-10-22 | Enichem Sintesi | Procedimento per la produzione di n-metilcarbammati |
| JP2007211029A (ja) * | 1997-02-14 | 2007-08-23 | Ube Ind Ltd | カルバメートの製法 |
| US6143917A (en) * | 1997-02-14 | 2000-11-07 | Ube Industries, Ltd. | Process for producing aryl carbamates |
| JP4859255B2 (ja) * | 2006-11-17 | 2012-01-25 | 旭化成ケミカルズ株式会社 | イソシアネートの製造方法 |
| TW200844080A (en) * | 2007-01-11 | 2008-11-16 | Asahi Kasei Chemicals Corp | Process for producing isocyanate |
| JP2007224046A (ja) * | 2007-05-23 | 2007-09-06 | Ube Ind Ltd | カルバメートの製造法 |
| US7977504B2 (en) | 2007-11-19 | 2011-07-12 | Asahi Kasei Chemicals Corporation | Process for producing isocyanates and aromatic hydroxy compounds |
| CN102026964B (zh) * | 2008-05-15 | 2013-12-25 | 旭化成化学株式会社 | 使用碳酸二芳基酯的异氰酸酯的制造方法 |
| BRPI0822694B1 (pt) * | 2008-05-15 | 2018-11-27 | Asahi Kasei Chemicals Corp | processo para produzir um isocianato |
| JP5067906B2 (ja) | 2009-08-21 | 2012-11-07 | 旭化成ケミカルズ株式会社 | Ｎ−置換カルバミン酸エステルの製造方法および該ｎ−置換カルバミン酸エステルを使用するイソシアネートの製造方法 |
| US8957241B2 (en) | 2011-02-21 | 2015-02-17 | Asahi Kasei Chemicals Corporation | Method for producing carbonyl compound |
| CN106349110A (zh) * | 2015-07-17 | 2017-01-25 | 大东树脂化学股份有限公司 | 制备脂肪族二异氰酸酯的二步法及一锅化合成法 |
| WO2018212206A1 (ja) | 2017-05-15 | 2018-11-22 | 旭化成株式会社 | イソシアネートの製造方法 |
| EP4431490A1 (en) | 2021-11-08 | 2024-09-18 | Asahi Kasei Kabushiki Kaisha | Method for producing isocyanate compounds, method for producing carbamate compounds, method for recovering amine compounds, and isocyanate composition |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR82018E (no) * | 1960-07-20 | 1964-03-16 | ||
| IL32061A (en) * | 1968-05-25 | 1972-08-30 | Bayer Ag | Indanyl-n-methylcarbamic acid esters,their preparation and use for pest control |
-
1975
- 1975-12-03 IT IT29960/75A patent/IT1051034B/it active
-
1976
- 1976-11-19 AU AU19801/76A patent/AU509444B2/en not_active Expired
- 1976-11-22 US US05/744,109 patent/US4097676A/en not_active Expired - Lifetime
- 1976-11-23 ZA ZA766992A patent/ZA766992B/xx unknown
- 1976-11-24 CA CA266,423A patent/CA1088093A/en not_active Expired
- 1976-11-26 YU YU02903/76A patent/YU290376A/xx unknown
- 1976-11-29 GB GB49727/76A patent/GB1532028A/en not_active Expired
- 1976-11-29 MW MW47/76A patent/MW4776A1/xx unknown
- 1976-11-30 DK DK538676A patent/DK538676A/da not_active Application Discontinuation
- 1976-12-01 LU LU76300A patent/LU76300A1/xx unknown
- 1976-12-01 NO NO764110A patent/NO764110L/no unknown
- 1976-12-01 DD DD196062A patent/DD127477A5/xx unknown
- 1976-12-02 FR FR7636338A patent/FR2333779A1/fr active Granted
- 1976-12-02 BR BR7608198A patent/BR7608198A/pt unknown
- 1976-12-02 PT PT65921A patent/PT65921B/pt unknown
- 1976-12-03 DE DE19762654939 patent/DE2654939A1/de active Pending
- 1976-12-03 BE BE172977A patent/BE849070A/xx not_active IP Right Cessation
- 1976-12-03 IE IE2666/76A patent/IE44472B1/en unknown
- 1976-12-03 NL NL7613526A patent/NL7613526A/xx not_active Application Discontinuation
- 1976-12-03 SE SE7613628A patent/SE433610B/xx unknown
- 1976-12-03 ZM ZM139/76A patent/ZM13976A1/xx unknown
- 1976-12-03 JP JP51144819A patent/JPS5271443A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| MW4776A1 (en) | 1978-02-08 |
| AU509444B2 (en) | 1980-05-15 |
| ZM13976A1 (en) | 1977-09-21 |
| NL7613526A (nl) | 1977-06-07 |
| SE433610B (sv) | 1984-06-04 |
| BR7608198A (pt) | 1977-11-22 |
| DK538676A (da) | 1977-06-04 |
| DE2654939A1 (de) | 1977-06-16 |
| PT65921B (en) | 1978-06-13 |
| SE7613628L (sv) | 1977-06-04 |
| GB1532028A (en) | 1978-11-15 |
| YU290376A (en) | 1982-05-31 |
| JPS5271443A (en) | 1977-06-14 |
| IE44472B1 (en) | 1981-12-16 |
| US4097676A (en) | 1978-06-27 |
| LU76300A1 (no) | 1977-06-09 |
| CA1088093A (en) | 1980-10-21 |
| FR2333779A1 (fr) | 1977-07-01 |
| AU1980176A (en) | 1978-05-25 |
| BE849070A (fr) | 1977-06-03 |
| PT65921A (en) | 1977-01-01 |
| IE44472L (en) | 1977-06-03 |
| FR2333779B1 (no) | 1980-06-20 |
| DD127477A5 (no) | 1977-09-28 |
| IT1051034B (it) | 1981-04-21 |
| ZA766992B (en) | 1977-10-26 |
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